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Citations (814)
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References A
B
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A: 6.5% B: 10.2%
With C11H14FeN3O11S*3H2O; dihydrogen peroxide; nitric acid in water; acetonitrile
T=25°C; P=760.051 Torr; 6 h; Reagent/catalyst; Overall yield = 16.7 percent;
Kopylovich, Maximilian N.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; Haukka, Matti; Amanullayeva, Gunel I.
Journal of Inorganic Biochemistry, 2012 , vol. 115, p. 72 - 77,6 Title/Abstract Full Text Show Details
With air
T=140°C; P=20594.2 Torr;
Phillips Petr. Co.
Patent: US2452741 , 1947 ; Full Text Show Details
A: 91 % Chromat. B: 1 % Chromat.
With sodium periodate; lt;RuO2(bipy)lt;IO3(OH)3gt;gt;*1.5H2O in dichloromethane; water
T=80°C; 15 h; Title compound not separated from byproducts;
Bailey, Alan J.; Griffith, William P.; Savage, Paul D.
Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995 , # 21 p. 3537 - 3542 Title/Abstract Full Text View citing articles Show Details
A: 13 % Chromat. B: 14 % Chromat.
With 1-diazo-2,3,4,5-tetrachlorocyclopenta-2,4-diene; oxygen
Oxidation; Photolysis;
Dunkin, Ian R.; McCluskey, Adam
Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 6 p. 1397 - 1400 Title/Abstract Full Text View citing articles Show Details
A: 2 % Chromat. B: 5 % Chromat.
With lt;Fe(μ-O2)(μ-PXDK)(O2CPhCy)2(Bu-Im)2gt;
T=-80 - 20°C; 0.0833333 h; other temperatures, reaction times, effects of O2 and additives; Product distribution;
LeCloux, Daniel D.; Barrios, Amy M.; Lippard, Stephen J.
Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 5 p. 763 - 772 Title/Abstract Full Text View citing articles Show Details
A: 4 % Chromat. B: 66 % Chromat.
With tetra-n-butylammonium nitridoosmate(VIII); iron(III) chloride in dichloromethane; acetic acid
T=23°C; 0.00833333 h; Product distribution;
Yiu, Shek-Man; Wu, Zhi-Biao; Mak, Chi-Keung; Lau, Tai-Chu
Journal of the American Chemical Society, 2004 , vol. 126, # 45 p. 14921 - 14929 Title/Abstract Full Text View citing articles Show Details
A: 11 % Chromat. B: 39 % Chromat.
With potassium permanganate; boron trifluoride acetonitrile complex in acetonitrile
T=24.85°C; Kinetics;
Lam, William W. Y.; Yiu, Shek-Man; Lee, Joyce M. N.; Yau, Sammi K. Y.; Kwong, Hoi-Ki; Lau, Tai-Chu; Liu, Dan; Lin, Zhenyang
Journal of the American Chemical Society, 2006 , vol. 128, # 9 p. 2851 - 2858 Title/Abstract Full Text View citing articles Show Details
With [Cu3(.mu.3-OH)(pyrazolate)3(acetate)2(pyrazole)]; dihydrogen peroxide; nitric acid in water; acetonitrile
T=25°C; P=760.051 Torr; 6 h;
Di Nicola, Corrado; Garau, Federica; Karabach, Yauhen Y.; Martins, Luisa M. D. R. S.; Monari, Magda; Pandolfo, Luciano; Pettinari, Claudio; Pombeiro, Armando J. L.
European Journal of Inorganic Chemistry, 2009 , # 5 p. 666 - 676 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in water; acetonitrile
T=50°C; P=760.051 Torr; 5 h;
Kirillova, Marina V.; Kirillov, Alexander M.; Guedes Da Silva, M. Fatima C.; Pombeiro, Armando J. L.
European Journal of Inorganic Chemistry, 2008 , # 22 p. 3423 - 3427 Title/Abstract Full Text View citing articles Show Details
With Cr2O4(2-)*Cu(2+); dihydrogen peroxide in acetonitrile T=50°C; 10 h;
Acharyya, Shankha S.; Ghosh, Shilpi; Adak, Shubhadeep; Tripathi, Deependra; Bal, Rajaram
Catalysis Communications, 2015 , vol. 59, p. 145 - 150 Title/Abstract Full Text View citing articles Show Details
With [Cu3(μ3-5-(4-pyridyl)tetrazolate)4(μ2-N3)2(DMF)2]n·(DMF)2n; dihydrogen peroxide in neat (no solvent) T=20°C; P=760.051 Torr; 10 h; Green chemistry; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure
Martins, Luísa; Nasani, Rajendar; Saha, Manideepa; Mobin, Shaikh; Mukhopadhyay, Suman; Pombeiro, Armando
Molecules, 2015 , vol. 20, # 10 p. 19203 - 19220 Title/Abstract Full Text View citing articles Show Details
A: 9.1 %Chromat. B: 0.8 %Chromat.
3.3. Typical Procedures for the Catalytic Oxidation of Cycloalkanes and Product Analysis
General procedure: The peroxidative oxidation reactions were typically carried out as follows: 0.1–20 μmol of the catalystwas added to 5.00 mmol of the cycloalkane, whereafter 10.00 mmol of 30percent H2O2 (1.02 mL) or of 70percentTBHP (688 μL) were added and the reaction solution was stirred for 10 h at r.t. and normal pressure.In the experiments with radical traps, CBrCl3 (5.00 mmol) or NHPh2 (5.00 mmol) was added to thereaction mixture. With [{Cu2(μ2-Hedea)2}2(μ4-pma)]n·4nH2O; dihydrogen peroxide; trifluoroacetic acid in water; acetonitrile
T=50°C; 5 h; Catalytic behavior; Reagent/catalyst; Overall yield = 35.5 percent;
Fernandes, Tiago A.; Santos, Carla I. M.; André, Vânia; Kłak, Julia; Kirillova, Marina V.; Kirillov, Alexander M.
Inorganic Chemistry, 2016 , vol. 55, # 1 p. 125 - 135 Title/Abstract Full Text View citing articles Show Details
With tert.-butylhydroperoxide in water
T=20°C; 24 h; Green chemistry;
Denicourt-Nowicki, Audrey; Lebedeva, Anastasia; Bellini, Clément; Roucoux, Alain
ChemCatChem, 2016 , vol. 8, # 2 p. 357 - 362 Title/Abstract Full Text View citing articles Show Details
With C40H32CoN8; oxygen
T=165°C; P=19502 Torr; 1.3 h; Reagent/catalystTemperaturePressure; Hide Experimental Procedure
Quzhou Qunying Chemical Industry Co., Ltd.; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong
Patent: CN105237355 A, 2016 ; Location in patent: Paragraph 0056; 0057 ; Title/Abstract Full Text Show Details
5:Example 5
The catalyst dissolved in the fresh cyclopentane added to the system is metal phthalocyanine (R1 = H, R2 = CH3CH2, M = Co) having the general formula (IV)And cobalt naphthenate,The total concentration was 45 ppm.When the device is in steady state,The flow rate of fresh cyclopentane fed to the oxidation reactor was 11.1 mL / h,The average residence time of the oxidation reactor in liquid phase was 1.3 h,The pressurized pure oxygen was continuousInto the oxidation reactor,Maintaining the system reaction temperature of 165 ,The reaction pressure was 2.6 MPa.After sampling analysis,The conversion of cyclopentane in the system was 99.4percentThe total selectivity of cyclopentanol and cyclopentanone was 95.1percentThe selectivity of cyclopentanol was 32.1percentThe selectivity to cyclopentanone was 63.0percent. With bis(acetylacetonato)manganese(II); oxygen
T=165°C; P=19502 Torr; 1.3 h; Reagent/catalystTemperaturePressure; Hide Experimental Procedure
Quzhou Qunying Chemical Industry Co., Ltd.; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong
Patent: CN105237355 A, 2016 ; Location in patent: Paragraph 0096; 0097 ; Title/Abstract Full Text Show Details
25:Example 25
The catalyst dissolved in fresh cyclopentane was added to the systemManganese acetylacetonate withN, N'-dihydroxyphthalimide,The total concentration was 120 ppm.When the device is in steady state,The flow rate of fresh cyclopentane in the oxidation reactor was 3.4 mL / h,In this case, the average residence time of the oxidation reactor in liquid phase was 2.3 h,The pressurized pure oxygen is continuously fed into the oxidation reactor,The reaction temperature was maintained at 152 ,The reaction pressure was 2.8 MPa.After sampling analysis,The conversion of cyclopentane in the system was 99.3percentThe total selectivity of cyclopentanol and cyclopentanone was 98.6percentThe selectivity of cyclopentanol was 64.3percentThe selectivity to cyclopentanone was 34.3percent. With C36H50Cu2N4O4(2+)*2NO3(1-); dihydrogen peroxide; trifluoroacetic acid in water; acetonitrile T=50°C; 3 h; Reagent/catalyst; Overall yield = 9 percent; Hide Experimental Procedure
Fernandes, Tiago A.; André, Vânia; Kirillov, Alexander M.; Kirillova, Marina V.
Journal of Molecular Catalysis A: Chemical, 2017 , vol. 426, p. 357 - 367 Title/Abstract Full Text View citing articles Show Details
Alkane oxidation reactions
General procedure: The alkane oxidation reactions were performed in air atmosphere in thermostated glass reactors equipped with a condenserunder vigorous stirring at 50°C and using MeCN as solvent (upto 5 mL total volume). In a typical experiment, catalyst 1 or 2(10 mol) and gas chromatography (GC) internal standard (MeNO2,50 L) were introduced into the MeCN solution, followed by the addition of an acid promoter (typically 0.1 mmol, optional) used asa stock solution in MeCN. An alkane or alcohol substrate (2 mmol) was then introduced, and the reaction started upon addition of hydrogen peroxide (50percent in H2O, 10 mmol) in one portion. The oxidation reactions were monitored by withdrawing small aliquots after different periods of time, which were treated with PPh3(following the Shul’pin’s method [24]) for the reduction of remaining H2O2 and alkyl hydroperoxides that are typically formed as primary products in alkane oxidations. The samples were analyzedby GC using nitromethane as an internal standard. Attribution ofpeaks was made by comparison with chromatograms of authentic samples. For comparative purposes, the oxidation of cyclohexanol to cyclohexanone was also investigated, following the abovementioned experimental procedure. Blank tests confirmed that alkane oxidations do not proceed in the absence of copper catalyst.
2
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Rx-ID: 276670 Find similar reactions
100%
With water; nickel dibromide; dibenzoyl peroxide in N,N-dimethyl acetamide
T=60°C; 3 h;
Youm, Jennessa Ji Youn; Schlaf, Marcel; Bierenstiel, Matthias
Tetrahedron Letters, 2008 , vol. 49, # 20 p. 3199 - 3203 Title/Abstract Full Text View citing articles Show Details
100%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane
20 h; Reflux; Solvent; Hide Experimental Procedure
KANTO CHEM CO INC; YAMAGUCHI, RYOHEI; FUJITA, KENICHI
Patent: JP2015/83544 A, 2015 ; Location in patent: Paragraph 0095; 0096 ; Title/Abstract Full Text Show Details
12:
General procedure: synthesis of ketones by dehydrogenation oxidation reaction of alcohol>the complex 1 used in the catalyst, the dehydrogenation oxidation of a variety of secondary alcohols with the reaction conditions as shown in Table 3 Reaction was carried out.After completion of the reaction, the reaction solution was analyzed by GC, and it was confirmed that the corresponding ketone was formed with high conversion and high yield in all cases 99%
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene
T=100°C; 13 h;
Minami, Ichiro; Shimizu, Isao; Tsuji, Jiro
Journal of Organometallic Chemistry, 1985 , vol. 296, p. 269 - 280 Title/Abstract Full Text View citing articles Show Details
99%
With air; potassium carbonate
T=100°C; 7 h;
Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara
Advanced Synthesis and Catalysis, 2009 , vol. 351, # 16 p. 2633 - 2637 Title/Abstract Full Text View citing articles Show Details
99%
With dihydrogen peroxide in water
T=89.84°C; 8 h;
Ding, Yong; Zhao, Wei; Ma, Bao-Chun; Qiu, Wen-Yuan
Canadian Journal of Chemistry, 2011 , vol. 89, # 1 p. 13 - 18 Title/Abstract Full Text View citing articles Show Details
99%
With dihydrogen peroxide
T=80°C; 3 h; Autoclaveneat (no solvent);
Wang, Xiaoli; Wu, Gongde; Wei, Wei; Sun, Yuhan
Transition Metal Chemistry, 2010 , vol. 35, # 2 p. 213 - 220 Title/Abstract Full Text View citing articles Show Details
98%
With dihydrogen peroxide in water
T=20°C; 2.5 h;
Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Eshghi, Hossein
Asian Journal of Chemistry, 2013 , vol. 25, # 6 p. 3307 - 3312 Title/Abstract Full Text View citing articles Show Details
98%
With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)]; potassium tertbutylate; acetone in methanol
T=56°C; Oppenauer Oxidation; P=750.075 Torr; 0.166667 h; Inert atmosphere; Catalytic behavior; Hide Experimental Procedure
Wang, Qingfu; Du, Wangming; Liu, Tingting; Chai, Huining; Yu, Zhengkun
Tetrahedron Letters, 2014 , vol. 55, # 9 p. 1585 - 1588 Title/Abstract Full Text View citing articles Show Details
A typical procedure for the catalytic oxidation of alcohols
General procedure: The catalyst solutionwas prepared by dissolving complex 3(36.1 mg,0.05mmol) in methanol (5.0 mL).Under a nitrogen atmosphere, the mixture of an alcohol substrate (2.0 mmol) and1.0 mL of the catalyst solution (0.01mmol) in 20mL acetone was stirred at 56 Cfor 10 minutes. tBuOK(22.4mg, 0.2 mmol)was then added to initiate the reaction.At the stated time, 0.1 mL of the reaction mixture was sampled and immediately diluted with 0.5 mL acetone pre-cooled-to-0 C for GC or NMR analysis. After the reaction was complete, the reaction mixture was condensed under reduced pressure and subject to purification by flash silica gel column chromatography to afford the corresponding ketone product, which was identified by comparison with the authentic sample through NMR and GC analysis. 97%
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 in acetonitrile
Oxidation; 0.666667 h; Heating;
Minghu, Wu; Guichun, Yang; Zuxing, Chen
Synthetic Communications, 2000 , vol. 30, # 17 p. 3127 - 3131 Title/Abstract Full Text View citing articles Show Details
97.1%
With oxygen in water
T=80°C; P=760.051 Torr; 24 h;
Wang, Tao; Shou, Heng; Kou, Yuan; Liu, Haichao
Green Chemistry, 2009 , vol. 11, # 4 p. 562 - 568 Title/Abstract Full Text View citing articles Show Details
97%
With dihydrogen peroxide in water; tert-butyl alcohol
T=80°C; 24 h;
Yamada, Yoichi M.A.; Jin, Chung Keun; Uozumi, Yasuhiro
Organic Letters, 2010 , vol. 12, # 20 p. 4540 - 4543 Title/Abstract Full Text View citing articles Show Details
96%
With Oxonereg; in water
T=70°C; 21 h; chemoselective reaction;
Wu, Shang; Ma, Hengchang; Lei, Ziqiang
Synlett, 2010 , # 18 p. 2818 - 2822 Title/Abstract Full Text View citing articles Show Details
96.1%
With tert.-butylhydroperoxide; C48H45Cu4N16O14; potassium carbonate in water
T=80°C; 4 h; Microwave irradiation; Reagent/catalyst;
Kopylovich, Maximilian N.; Mizar, Archana; Guedes Da Silva, M. Fatima C.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.
Chemistry - A European Journal, 2013 , vol. 19, # 2 p. 588 - 600 Title/Abstract Full Text View citing articles Show Details
96%
With dihydrogen peroxide in water
T=80°C; 12 h; Green chemistry; TimeTemperature;
Rajabi, Fatemeh; Pineda, Antonio; Naserian, Sareh; Balu, Alina Mariana; Luque, Rafael; Romero, Antonio A.
Green Chemistry, 2013 , vol. 15, # 5 p. 1232 - 1237 Title/Abstract Full Text View citing articles Show Details
96%
With [Fe(1,1′-methylene-3,3′-di-benzylimidazole-2-ylidene)(bipy)I2] in neat (no solvent) T=80°C; 8 h; Inert atmosphereSchlenk technique; Catalytic behavior;
Pinto, Mara F.; Cardoso, Bernardo De P.; Barroso, Sónia; Martins, Ana M.; Royo, Beatriz
Dalton Transactions, 2016 , vol. 45, # 34 p. 13541 - 13546 Title/Abstract Full Text View citing articles Show Details
95%
With [Cp*Ru(μ-Cl)3RuCl(PPh3)2]; potassium carbonate in dichloromethane; butanone
Heating;
Da Silva, Ana C.; Piotrowski, Holger; Mayer, Peter; Polborn, Kurt; Severin, Kay
European Journal of Inorganic Chemistry, 2001 , # 3 p. 685 - 691 Title/Abstract Full Text View citing articles Show Details
95%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; tert.-butylnitrite; oxygen in 1,2-dichloro-ethane
P=1500.15 Torr; 12 h; AutoclaveHeating;
He, Xijun; Shen, Zhenlu; Mo, Weimin; Sun, Nan; Hu, Baoxiang; Hu, Xinquan
Advanced Synthesis and Catalysis, 2009 , vol. 351, # 1-2 p. 89 - 92 Title/Abstract Full Text View citing articles Show Details
95%
With tert.-butylhydroperoxide in decane; acetonitrile
T=65°C; 2.5 h;
Verma, Sanny; Nandi, Mahasweta; Modak, Arindam; Jain, Suman L.; Bhaumik, Asim
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 11-12 p. 1897 - 1902 Title/Abstract Full Text View citing articles Show Details
94%
With N-methylpyrrolidine-2-one hydrotribromide; dihydrogen peroxide in acetonitrile
0.42 h; Heating;
Joseph, Jomy K.; Jain, Suman L.; Sain, Bir
European Journal of Organic Chemistry, 2006 , # 3 p. 590 - 594 Title/Abstract Full Text View citing articles Show Details
94%
With tert.-butylhydroperoxide in decane; acetonitrile
T=65°C; 0.333333 h;
Mungse, Harshal P.; Verma, Sanny; Kumar, Neeraj; Sain, Bir; Khatri, Om P.
Journal of Materials Chemistry, 2012 , vol. 22, # 12 p. 5427 - 5433 Title/Abstract Full Text View citing articles Show Details
93%
With sodium bromate; hydrogen bromide in acetic acid
T=40°C; 3 h;
Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo
Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 747 - 750 Title/Abstract Full Text Show Details
93%
With tert.-butylhydroperoxide in water; acetonitrile
T=80°C;
Dhanalaxmi, Karnekanti; Singuru, Ramana; Kundu, Sudipta K.; Reddy, Benjaram Mahipal; Bhaumik, Asim; Mondal, John
RSC Advances, 2016 , vol. 6, # 43 p. 36728 - 36735 Title/Abstract Full Text View citing articles Show Details
92%
With potassium carbonate
T=100°C; 5 h; Neat (no solvent);
Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 4 p. 606 - 616 Title/Abstract Full Text View citing articles Show Details
92%
With nickel(II) nitrate hexahydrate; iodine in water
T=25°C; 0.0333333 h; Sonication; Hide Experimental Procedure
Pasha, Mohamed Afzal; Nagashree, Shrivatsa
Ultrasonics Sonochemistry, 2013 , vol. 20, # 3 p. 810 - 814 Title/Abstract Full Text View citing articles Show Details
2.2. Oxidation of alcohols under ultrasonic condition: a general procedure
General procedure: A mixture of alcohol (10 mmol), Ni(NO3)2*6H2O (2.908 g, 10 mmol), I2 (1.3 g, 10 mmol) and water (2 mL) were sonicated in a sonic bath working at 35 kHz (constant frequency) maintained at 25 °C by circulating water. After completion of the reaction (Table 5, monitored on TLC), the product was taken into diethyl ether (10 mL), the organic matter was washed with sat. NaHCO3 (2.5 mL), water (5 mL) and then dried over anhydrous Na2SO4. The organic layer was evaporated in a fume hood to get almost pure aldehyde. The crude was then subjected to silica gel column chromatography to get the pure product. All the products were characterized by IR, GC–mass spectral analysis; and the physical properties were compared with the properties of authentic samples. 92%
With aluminum oxide in N,N-dimethyl-formamide
T=120°C; 10 h; Inert atmosphere;
Damodara, Dandu; Arundhathi, Racha; Likhar, Pravin R.
Advanced Synthesis and Catalysis, 2014 , vol. 356, # 1 p. 189 - 198 Title/Abstract Full Text View citing articles Show Details
92%
With [(η5-Cp*)Ir(1-benzyl-3-phenylselenomethyl-1,3-dihydrobenzoimidazole-2-selenone)Cl] [PF6]; potassium tert-butylate; acetone
T=80°C; 3 h; Reagent/catalyst;
Sharma, Alpesh K.; Joshi, Hemant; Bhaskar, Renu; Singh, Ajai K.
Dalton Transactions, 2017 , vol. 46, # 7 p. 2228 - 2237 Title/Abstract Full Text View citing articles Show Details
91%
With chromium(VI) oxide; aluminum oxide in hexane
T=39.9°C; 15 h;
Hirano, Masao; Nagasawa, Sonoko; Morimoto, Takashi
Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 9 p. 2857 - 2859 Title/Abstract Full Text Show Details
91%
With dihydrogen peroxide; bromine in dichloromethane; water
T=20°C; 2 h;
Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene
Organic Process Research and Development, 1998 , vol. 2, # 4 p. 261 - 269 Title/Abstract Full Text View citing articles Show Details
90%
With pyridine; tert-butylhypochlorite in dichloromethane
1 h;
Milovanovic, Jovan N.; Vasojevic, Miorad; Gojkovic, Svetislav
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988 , p. 533 - 536 Title/Abstract Full Text Show Details
90%
With aluminum (III) chloride; Oxonereg; in water
T=20°C; 4 h;
Wu, Shang; Ma, Hengchang; Lei, Ziqiang
Tetrahedron, 2010 , vol. 66, # 45 p. 8641 - 8647 Title/Abstract Full Text View citing articles Show Details
90%
With dihydrogen peroxide in water; acetonitrile
T=25°C; 3.75 h;
Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Takjoo, Reza; Eshghi, Hossein
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013 , vol. 43, # 3 p. 264 - 272 Title/Abstract Full Text View citing articles Show Details
90%
With tert.-butylhydroperoxide; thiourea S,S-dioxide in dodecane; acetonitrile
T=65°C; 4 h;
Verma, Sanny; Singh, Raghuvir; Tripathi, Deependra; Gupta, Piyush; Bahuguna, Gajendra Mohan; Jain, Suman L.
RSC Advances, 2013 , vol. 3, # 13 p. 4184 - 4188 Title/Abstract Full Text View citing articles Show Details
90%
With tert.-butylhydroperoxide in dodecane; acetonitrile
T=65°C; 1 h; Hide Experimental Procedure
Verma, Sanny; Le Bras, Jean; Jain, Suman L.; Muzart, Jacques
Applied Catalysis A: General, 2013 , vol. 468, p. 334 - 340 Title/Abstract Full Text View citing articles Show Details
Oxidation of alcohols 10 to carbonyl compounds 11
General procedure: A 25 mL round bottom flask was charged with alcohol (1.0 mmol), catalyst (0.02 equiv.), MeCN (5 mL), TBHP (1.5 M solution in dodecane; 1.5 equiv.) and then stirred at 65 °C for 1 h. According to Table 2, all reactions require 1 h. At the end of the reaction, the catalyst was filtered at room temperature over membrane filter paper and reused for subsequent runs. The filtrate so obtained was concentrated under reduced pressure and the residue was dissolved in dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL 3×). The organic layer was dried over anhydrous MgSO4 and then, concentrated under reduced pressure. Product was purified by column chromatography over silica gel. The isolated yield of the obtained product was found to be 94percent and the conversion was determined by the GC–MS analysis. The purity of the products was determined by comparing the 1H NMR spectra of the products with those of authentic samples. 90%
With tert.-butylhydroperoxide in water
T=60°C; 3 h;
Patnam, Padma L.; Bhatt, Mukesh; Singh, Raghuvir; Saran, Sandeep; Jain, Suman L.
RSC Advances, 2016 , vol. 6, # 65 p. 60888 - 60895 Title/Abstract Full Text View citing articles Show Details
89.9%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water; potassium carbonate; ruthenium trichloride in ethyl acetate
Nagase & Co., Ltd.; Nagase Chemtex Corporation
Patent: JP2005/75784 A, 2005 ;
T=20 - 45°C; 1 - 3 h; Product distribution / selectivity;
Location in patent: Page/Page column 20-21; 23-24 ;
89%
With morpholinium fluorochromate(VI) absorbed on wet silica gel in hexane
T=20°C; 0.35 h;
Sayyed-Alangi, S. Zahra; Sajjadi-Ghotbabadi; Baei, Mohammed T.; Naderi, Sahar
E-Journal of Chemistry, 2011 , vol. 8, # 2 p. 815 - 818 Title/Abstract Full Text View citing articles Show Details
88%
With air; bis(salicylideniminato-3-propyl)methylamino-cobalt(III); 2,6-dimethoxy-pquinone; [C5Ph4O(Ru(CO)2)]2H2 in toluene
T=100°C; 1 h;
Csjernyik, Gabor; Ell, Alida H.; Fadini, Luca; Pugin, Benoit; Baeckvall, Jan-E.
Journal of Organic Chemistry, 2002 , vol. 67, # 5 p. 1657 - 1662 Title/Abstract Full Text View citing articles Show Details
88%
With dihydrogen peroxide; benzyltrimethylammonium bromide dibromide in water; acetonitrile
T=60°C; 3 h; Green chemistry;
Dey, Madhudeepa; Dhar, Siddhartha Sankar; Kalita, Mukul
Synthetic Communications, 2013 , vol. 43, # 12 p. 1734 - 1742 Title/Abstract Full Text View citing articles Show Details
88%
With DHPDMDO in acetonitrile
T=20°C; 0.583333 h;
Azarifar, Davood; Najminejad, Zohreh; Khosravi, Kaveh
Journal of the Iranian Chemical Society, 2013 , vol. 10, # 5 p. 979 - 983 Title/Abstract Full Text View citing articles Show Details
88%
With oxygen in water
T=100°C; P=37503.8 Torr; 1 h; Flow reactorGreen chemistry;
Osako, Takao; Torii, Kaoru; Uozumi, Yasuhiro
RSC Advances, 2015 , vol. 5, # 4 p. 2647 - 2654 Title/Abstract Full Text View citing articles Show Details
87%
With ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate
2 h; Ambient temperature;
Green, Graham; Griffith, William P.; Hollinshead, David M.; Ley, Steven V.; Schroeder, Martin
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 4 p. 681 - 686 Title/Abstract Full Text View citing articles Show Details
87%
With ferric(III) bromide; dihydrogen peroxide
T=20°C; 24 h;
Martin, Sandra E.; Garrone, Analia
Tetrahedron Letters, 2003 , vol. 44, # 3 p. 549 - 552 Title/Abstract Full Text View citing articles Show Details
87%
With oxygen in toluene
T=80°C; 1 h;
Kantam, M. Lakshmi; Pal, Ujjwal; Sreedhar; Bhargava, Suresh; Iwasawa, Yasuhiro; Tada, Mizuki; Choudary
Advanced Synthesis and Catalysis, 2008 , vol. 350, # 9 p. 1225 - 1229 Title/Abstract Full Text View citing articles Show Details
87.2%
With C31H29ClN4OPRuS(1+)*F6P(1-); 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux; Catalytic behavior; Reagent/catalyst;
Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan
Applied Organometallic Chemistry, 2014 , vol. 28, # 8 p. 641 - 651 Title/Abstract Full Text View citing articles Show Details
87%
With O40SiW12(4-)*4C17H38NO3S(1+); dihydrogen peroxide
T=70°C; 4 h; Green chemistry; Reagent/catalyst; Hide Experimental Procedure
Li, Xinzhong; Cao, Rong; Lin, Qi
Catalysis Communications, 2015 , vol. 69, p. 5 - 10 Title/Abstract Full Text View citing articles Show Details
Title/Abstract Full Text Show Details
2.3. General procedure for oxidation of alcohols
General procedure: A mixture of S4SiIL or S3PIL (0.05mmol) and alcohol (30mmol) in a 25 mL flask fitted with a reflux condenser was heated to the reactiontemperature, then the required amount of aqueous H2O2 was addeddropwise under stirring. The progress of the reaction was monitored by TLC (GF254 silica gel coloration in phosphomolybdic acid/ethanol for aromatic alcohol, in KMnO4 solution for aliphatic alcohol). After the completion, the reaction mixture was extracted with diethyl ether(3 × 20 mL), solvent was evaporated in a vacuum. The residual was analyzedby gas chromatography (HP 6890) equippedwith a flame ionizationdetector and an SE-54 column. The aqueous phase was subjected torotary evaporation, and then was dried at 85 °C under a vacuum for 8 hto give regenerated ionic liquids. Pure oxidation products were obtainedby column chromatography (petroleum ether-ethyl acetate 9:1 (V/V))and identified by the comparison of their IR and 1H NMR spectra withthose of authentic samples. 86%
With aluminum oxide; ammonium chlorochromate in cyclohexane
T=60°C; 3 h;
Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun
Synthetic Communications, 1997 , vol. 27, # 6 p. 953 - 956 Title/Abstract Full Text View citing articles Show Details
86%
With C23H23ClN3RuSe2(1+)*F6P(1-); 4-methylmorpholine N-oxide in dichloromethane
Reflux;
Das, Dipanwita; Singh, Pradhumn; Prakash, Om; Singh, Ajai K.
Inorganic Chemistry Communications, 2010 , vol. 13, # 11 p. 1370 - 1373 Title/Abstract Full Text View citing articles Show Details
85%
With 1-oxo-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride in dichloromethane
1 h; Ambient temperature;
Yamaguchi; Takata; Endo
Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 3 p. 947 - 949 Title/Abstract Full Text View citing articles Show Details
85%
With ammonium chlorochromate; silica gel in cyclohexane
Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun
T=60°C; 3 h;
Synthetic Communications, 1997 , vol. 27, # 21 p. 3691 - 3696 Title/Abstract Full Text View citing articles Show Details
85%
With iron(II) perchlorate monohydrate; ozone; acetonitrile
Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja
ACS Catalysis, 2015 , vol. 5, # 3 p. 1629 - 1637 Title/Abstract Full Text View citing articles Show Details
85%
With titanium(IV) oxide; oxygen
T=29.84°C; P=760.051 Torr; 24 h; Sealed tubeIrradiation;
Vadakkekara, Raji; Biswas, Abul Kalam; Sahoo, Tapan; Pal, Provas; Ganguly, Bishwajit; Ghosh, Subhash Chandra; Panda, Asit Baran
Chemistry - An Asian Journal, 2016 , vol. 11, # 21 p. 3084 - 3089 Title/Abstract Full Text View citing articles Show Details
84%
With sodium bromite in acetic acid
5 h; Ambient temperature;
Kageyama, Toshifumi; Ueno, Yoshio; Okawara, Makoto
Synthesis, 1983 , # 10 p. 815 - 816 Title/Abstract Full Text Show Details
84%
With aluminum oxide; quinolinium monofluorochromate(VI) in hexane
4.5 h; Ambient temperature;
Rajkumar, G. Abraham; Arabindoo, Banumathi; Murugesan
Synthetic Communications, 1999 , vol. 29, # 12 p. 2105 - 2114 Title/Abstract Full Text View citing articles Show Details
84%
With manganese(III) acetylacetonate; acetonitrile in tetrachloromethane
T=200°C; 3 h;
Khusnutdinov; Schadneva; Baiguzina; Dzhemilev
Russian Chemical Bulletin, 2002 , vol. 51, # 6 p. 1065 - 1067 Title/Abstract Full Text View citing articles Show Details
84%
With C77H60Cl2N4O4PRu2; 4-methylmorpholine N-oxide in dichloromethane
8 h; Reflux;
Venkatachalam; Raja; Pandiarajan; Ramesh
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2008 , vol. 71, # 3 p. 884 - 891 Title/Abstract Full Text View citing articles Show Details
84%
With C17H16Cl2N3O2RuS; 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux; Catalytic behavior; Reagent/catalyst;
Pramanik, Ajoy Kumar; Mondal, Tapan Kumar
Inorganica Chimica Acta, 2014 , vol. 411, p. 106 - 112 Title/Abstract Full Text View citing articles Show Details
84%
With oxygen; isovaleraldehyde in acetonitrile
T=65°C; 3.5 h; Catalytic behavior; Hide Experimental Procedure
Panwar, Vineeta; Kumar, Pawan; Ray, Siddharth S.; Jain, Suman L.
Tetrahedron Letters, 2015 , vol. 56, # 25 p. 3948 - 3953 Title/Abstract Full Text View citing articles Show Details
General procedure for the oxidation
General procedure: A mixture of benzhydrol (1 mmol, 0.184 g), isobutyraldehyde (1.5 mmol, 0.108 g), and catalyst (1 mol percent 0.01 mmol) in acetonitrile (15 mL) was heated at 60 °C under stirring by using an oxygen balloon. The progress of the reaction was monitored by thin layer chromatography on silica gel. On completion, the reaction mixture was cooled to room temperature and centrifuged to separate the catalyst. The product was identified with GCMS. The solvent was removed under reduced pressure and the product was obtained by passing it through a short column of silica gel using EtOAc–hexane (1:9) as eluent. The identity of the product was confirmed by comparing the physical and spectral data (1H and 13C NMR) with the reported compound. The recovered catalyst was dried at 50 °C for 2 h and can be reused for recycling experiments. 83%
With potassium hexafluorophosphate; tert.-butylnitrite; 9-azabicyclo[3.3.1]nonane-Noxyl; oxygen in water
T=60°C; P=3750.38 Torr; 3.5 h; AutoclaveGreen chemistry;
Ma, Jiaqi; Hong, Chao; Wan, Yan; Li, Meichao; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Jin, Liqun; Shen, Zhenlu
Tetrahedron Letters, 2017 , vol. 58, # 7 p. 652 - 657 Title/Abstract Full Text View citing articles Show Details
81%
With isocyanate de chlorosulfonyle; dimethyl sulfoxide; triethylamine in dichloromethane
1.) -78 deg C, 1.5 h, 2.) room temperature, 0.5 h;
Olah, George A.; Vankar, Yashwant D.; Arvanaghi, Massoud
Synthesis, 1980 , # 2 p. 141 - 142 Title/Abstract Full Text Show Details
81%
With (tetrabutylammonium)4[Al4(H2O)10(β-SbW9O33H)2]*4H2O; dihydrogen peroxide in water; acetonitrile
T=70°C; 1 h; Catalytic behavior; Reagent/catalyst;
Carraro, Mauro; Bassil, Bassem S.; Soraru, Antonio; Berardi, Serena; Suchopar, Andreas; Kortz, Ulrich; Bonchio, Marcella
Chemical Communications, 2013 , vol. 49, # 72 p. 7914 - 7916 Title/Abstract Full Text View citing articles Show Details
80%
With sodium bromate; sodium dihydrogenphosphate; iron(III) chloride in water; acetonitrile
T=25°C; 4 h;
Shaabani; Ajabi
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 2 p. 148 - 151 Title/Abstract Full Text View citing articles Show Details
80%
With oxygen in water
T=60°C; P=760.051 Torr; 12 h;
Yamada, Yoichi M.A.; Arakawa, Takayasu; Hocke, Heiko; Uozumi, Yasuhiro
Chemistry - An Asian Journal, 2009 , vol. 4, # 7 p. 1092 - 1098 Title/Abstract Full Text View citing articles Show Details
78%
With dihydrogen peroxide in water; acetone
T=56°C; 19 h; chemoselective reaction;
Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka
Angewandte Chemie - International Edition, 2010 , vol. 49, # 35 p. 6096 - 6100
Title/Abstract Full Text View citing articles Show Details
77%
With air; ferric(III) bromide; ferric nitrate in acetonitrile
T=20°C; 24 h;
Martin, Sandra E; Suarez, Dario F
Tetrahedron Letters, 2002 , vol. 43, # 25 p. 4475 - 4479 Title/Abstract Full Text View citing articles Show Details
75%
With Amberlite IRA-120; urea-hydrogen peroxide; 1-n-butyl-3-methylimidazolim bromide
T=70°C; 4 h;
Bhati, Nishi; Sarma, Kuladip; Goswami, Amrit
Chemistry Letters, 2008 , vol. 37, # 5 p. 496 - 497 Title/Abstract Full Text View citing articles Show Details
74%
With oxygen
16 h; electrolysis: Hg cathode, plazinum foil anode, n-Bu4N(1+)*ClO4(1-) / DMF, -1.0 V vs SCE;
Singh, Manorama; Misra, Ram A.
Synthesis, 1989 , # 5 p. 403 - 404 Title/Abstract Full Text Show Details
71%
With 3-chloro-benzenecarboperoxoic acid; (5,10,15,20tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride in dichloromethane; acetonitrile
T=20°C; 0.166667 h;
Han, Jung Hee; Yoo, Sang-Kun; Seo, Jin Soo; Hong, Sung Jin; Kim, Seok Kyu; Kim, Cheal
Dalton Transactions, 2005 , # 2 p. 402 - 406 Title/Abstract Full Text View citing articles Show Details
70%
With dihydrogen peroxide; [Me(n-C8H17)3N]HSO4; sodium tungstate in water
T=90°C; Oxidation; 16 h;
Sato, Kazuhiko; Aoki, Masao; Takagi, Junko; Zimmermann, Klaus; Noyori, Ryoji
Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 10 p. 2287 - 2306 Title/Abstract Full Text View citing articles Show Details
70%
With potassium hydroxide; cobalt(II) phthalocyanine; oxygen in xylene
15 h; Heating;
Sharma, Vishal B.; Jain, Suman L.; Sain, Bir
Tetrahedron Letters, 2003 , vol. 44, # 2 p. 383 - 386 Title/Abstract Full Text View citing articles Show Details
70%
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide in various solvent(s) T=20°C; 6 h;
Jain, Suman L.; Sharma, Vishal B.; Sain, Bir
Bulletin of the Chemical Society of Japan, 2006 , vol. 79, # 10 p. 1601 - 1603 Title/Abstract Full Text View citing articles Show Details
68%
With C16H12Cl2N2O3RuS; 4-methylmorpholine N-oxide in dichloromethane
T=4°C; 1 h; Molecular sieveReflux; Hide Experimental Procedure
Roy, Puspendu; Mondal, Apurba Sau; Pramanik, Ajoy Kumar; Mondal, Tapan Kumar
Journal of Organometallic Chemistry, 2017 , vol. 828, p. 1 - 9 Title/Abstract Full Text View citing articles Show Details
General procedure: A solution of complex 1 (0.01mmol) in CH2Cl2 (25mL) was added to the mixture containing PhCH2OH (1mmol), NMO (3mmol) and molecular sieves. The reaction mixture was refluxed and conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to ≈1mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP–5 column of 30m length, 0.53mm diameter and 5.00μm film thickness. The column, injector and detector temperatures were 200, 250 and 250°C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30mL/min. The injection volume of sample was 2μL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50min. All other alcohols were oxidized by refluxing the reaction mixture for 1h and conversions were monitored following the identical protocol.
67%
Stage #1: With potassium permanganate in acetone
Reflux; Stage #2: With hydrogenchloride in water
Zheng, Min-Yan; Wei, Yong-Sheng; Fan, Guang; Huang, Yi
Asian Journal of Chemistry, 2012 , vol. 24, # 1 p. 161 - 164 Title/Abstract Full Text View citing articles Show Details
65%
With aluminum oxide; dimethylammonium chlorochromate in cyclohexane
T=55 - 60°C; 3 h;
Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun
Organic Preparations and Procedures International, 1998 , vol. 30, # 2 p. 215 - 218 Title/Abstract Full Text View citing articles Show Details
65%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water
T=25°C; 24 h; Micellar solution; Hide Experimental Procedure
Xie, Aming; Zhou, Xiangxiang; Feng, Liandong; Hu, Xinyu; Dong, Wei
Tetrahedron, 2014 , vol. 70, # 21 p. 3514 - 3519 Title/Abstract Full Text View citing articles Show Details
General procedure for the oxidation of alcohols
General procedure: A vial was charged with alcohol (1 mmol), IBX (1.2 mmol, 1.2 equiv) and 2 wt percent GMPGS-2000/H2O solution (5 mL). The mixture was stirred for 24 h at 25 °C and filtered. The solid was washed with CH2Cl2 and the filtrate was extracted with CH2Cl2 (3×10 mL). Then, the organic phase was combined and dried with anhydrous Na2SO4, evaporated to dryness. The crude product was purified was purified by column chromatography on silica gel eluted with (petroleum ether/EtOAc) to afford the desired product. 64%
With 30percent peracetic acid; resin-PPh2-Ru(PPh3)2Cl2 in ethyl acetate; 1,2-dichloro-ethane
2 h; Heating;
Leadbeater
Journal of Organic Chemistry, 2001 , vol. 66, # 6 p. 2168 - 2170 Title/Abstract Full Text View citing articles Show Details
64%
With [MnIII(2-((2-(2-(2-(2hydroxybenzylideneamino)phenylamino)propylamino)phenylimino)methyl)phenolato)]Cl; dihydrogen peroxide in acetonitrile
3.3 h; Reflux;
Azadbakht, Reza; Amini Manesh, Abbas; Malayeri, Mahdieh; Dehghani, Behzad
New Journal of Chemistry, 2015 , vol. 39, # 8 p. 6459 - 6464 Title/Abstract Full Text View citing articles Show Details
54%
With pyridine; C22H16CoN2O8; oxygen in water
T=80°C; pH=11.5; 7 h;
Seyedi, Seyed Mohammad; Sandaroos, Reza; Zohuri, Gholam Hossein
Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1303 - 1306 Title/Abstract Full Text View citing articles Show Details
54%
With pyridine-2-carbaldehyde; 2-(Aminomethyl)pyridine; iron(II) trifluoromethanesulfonate acetonitrile disolvate; dihydrogen peroxide in acetonitrile
T=25°C; 1.5 h;
Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; Di Stefano, Stefano
Organic and Biomolecular Chemistry, 2016 , vol. 14, # 45 p. 10630 - 10635 Title/Abstract Full Text View citing articles Show Details
51%
With dihydrogen peroxide; ortho-tungstic acid; 1-octyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amide in water
T=90°C; 1 h; Green chemistry; Hide Experimental Procedure
Chatel, Gregory; Monnier, Camille; Kardos, Nathalie; Voiron, Celine; Andrioletti, Bruno; Draye, Micheline
Applied Catalysis A: General, 2014 , vol. 478, p. 157 - 164 Title/Abstract Full Text View citing articles Show Details
Optimized cyclohexanol oxidation with Aliquat 336
General procedure: Cyclohexanol (1.04 mL, 10 mmol, 1 equiv.), tungstic acid(58.9 mg, 0.24 mmol, 2.4 molpercent), Aliquat 336 (275 mg, 0.68 mmol,6.8 molpercent) and 30percent hydrogen peroxide (2.04 mL, 20 mmol, 2 equiv.)were introduced into a glass tube. The mixture was stirred at90 C for 30 min. Then, the organic phase was extracted withethyl acetate (3×2 mL) and cyclohexane (2×2 mL). The combinedorganic phases were dried with MgSO4 and analysed bygas chromatography (GC). The same procedure was used from theother substrates: cyclopentanol (0.91 mL, 10 mmol, 1 equiv.), cycloheptanol(1.20 mL, 10 mmol, 1 equiv.) and cyclooctanol (1.32 mL,10 mmol, 1 equiv.). 50.2%
With copper oxide-silica catalyst (copper oxide 49 mass percent, 47 mass percent of silica, 1 mass percent of alumina, 2 mass percent of sodium oxide and 1 mass percent of other metal oxides) T=190°C; Reagent/catalyst; Hide Experimental Procedure
ZEON CORPORATION; NAKANO, YASUSHI
Patent: JP5790103 B2, 2015 ; Location in patent: Paragraph 0049 ; Title/Abstract Full Text Show Details
2:
(Silicon oxide)-based catalyst (copper oxide 67 mass percent, silicon 27 mass percent, sodium oxide 2 mass percent, and other metal oxides) were added to a stainless steel reaction tube (inner diameter 9.3 mm, length 100 mm) and E35S, manufactured by NittoKasei Chemical Industry Co., Ltd.), and the mixture was heated in an oven to 190 °C. Next, the reduction catalyst was subjected to reduction treatment in the reaction tube First, the vaporized cyclopentanol (purity of 99.2percent) was supplied from the inlet of the reaction tube at a rate of LHSV = 3.3 hr -1, and the reaction tube While the outlet pressure was maintained at atmospheric pressure, continuous reaction was carried out at 190 °C. In this case, since the reaction product flows out from the outlet of the reaction tube as a gas, it was cooled and collected to obtain a condensate (crude product). The condensate collected during 50 to 51 hours after the start of the continuous reaction was analyzed by gas chromatograph and the conversion rate of cyclopentanol, the selectivity of cyclopentanone, the yield of cyclopentanone. 48%
With C16H13MnNO3*3H2O; dihydrogen peroxide in water
T=20°C; 1 h; Ionic liquid;
Rong, Meizhu; Wang, Juan; Shen, Yanping; Han, Jinyu
Catalysis Communications, 2012 , vol. 20, p. 51 - 53 Title/Abstract Full Text View citing articles Show Details
47%
With dihydrogen peroxide in water; acetonitrile
T=80°C; 4 h; chemoselective reaction;
Stolle, Achim; Ondruschka, Bernd; Morgenthal, Ingrid; Andersen, Olaf; Bonrath, Werner
Journal of Molecular Catalysis A: Chemical, 2011 , vol. 335, # 1-2 p. 228 - 235 Title/Abstract Full Text View citing articles Show Details
45%
With oxygen; benzaldehyde in 1,2-dichloro-ethane
T=80°C; 36 h;
Choudary, Boyapati M.; Sudha, Yepuri
Synthetic Communications, 1996 , vol. 26, # 9 p. 1651 - 1655 Title/Abstract Full Text View citing articles Show Details
43%
With dihydrogen peroxide in acetone
T=24.84°C; 20 h; Inert atmosphereSchlenk technique;
Xiang, Jing; Li, Hao; Wu, Jia-Shou
Zeitschrift fur Anorganische und Allgemeine Chemie, 2014 , vol. 640, # 8-9 p. 1670 - 1674 Title/Abstract Full Text View citing articles Show Details
39.5%
With C56H45N4O3OsP2(1+)*ClO4(1-); 4-methylmorpholine N-oxide in dichloromethane
4 h; RefluxMolecular sieve; Catalytic behavior; Reagent/catalyst;
Datta, Papia; Sardar, Dibakar; Panda, Uttam; Halder, Ajanta; Manik, Nabin Baran; Chen, Chun-Jung; Sinha, Chittaranjan
Applied Organometallic Chemistry, 2016 , vol. 30, # 5 p. 323 - 334 Title/Abstract Full Text View citing articles Show Details
37%
With tetrahexylammonium chloride; dihydrogen peroxide; lt;NBu4gt;lt;(Ph2PO2)(WO(O2)2)2gt; in benzene
T=75°C; 3 h; other new heteropolyperoxometalate catalysts and oxidation of various primary and secondary alcohols investigated;
Gresley, N. Melanie; Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.
Journal of the Chemical Society - Dalton Transactions, 1996 , # 10 p. 2039 - 2045 Title/Abstract Full Text View citing articles Show Details
32.1%
With sodium ferrate(VI) in water
3 h;
Tandon, Praveen K.; Singh, Santosh B.; Singh, Satpal; Kesarwani, Bhawana
Journal of the Indian Chemical Society, 2012 , vol. 89, # 10 p. 1363 - 1367 Title/Abstract Full Text View citing articles Show Details
31%
With dihydrogen peroxide; lt;NMe4gt;3lt; (MePO3)lt;MePO2(OH)gt;W6O13(O2)4(OH)2(OH2)gt;*4H2O
T=70°C; 3 h;
Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.
Journal of the Chemical Society, Chemical Communications, 1995 , # 21 p. 2183 - 2184 Title/Abstract Full Text View citing articles Show Details
26%
With boron trifluoride diethyl etherate; pyCo(TPP)NO2
1 h;
Tovrog,Benjamin S.; Diamond, Steven E.; Mares, Frank; Szalkiewicz, Andrew
Journal of the American Chemical Society, 1981 , vol. 103, # 12 p. 3522 - 3526
Title/Abstract Full Text View citing articles Show Details
15%
With Bis(7-methyl-10-(n-octyl)pyridodipyrimidin-3-yl)decane
T=115°C; 25 h;
Yoneda, Fumio; Tanaka, Kiyoshi; Yamato, Hirotake; Moriyama, Kenji; Nagamatsu, Tomohisa
Journal of the American Chemical Society, 1989 , vol. 111, # 20 p. 9199 - 9202 Title/Abstract Full Text View citing articles Show Details
10.5%
With oxygen; 3,7-dimethyl-10-n-propylpyrimidolt;5,4-ggt;pteridine-2,4,6,8(3H,7H,9H,10H)-tetrone
Nagamatsu, Tomohisa; Matsumoto, Etsuko; Yoneda, Fumio
Chemistry Letters, 1982 , p. 1127 - 1130 Title/Abstract Full Text Show Details
10.5%
With oxygen; 3,7-dimethyl-10-n-propylpyrimidolt;5,4-ggt;pteridine-2,4,6,8(3H,7H,9H,10H)-tetrone
T=120°C; 25 h;
T=120°C; 25 h; further 10-substituted pyrimido<5,4-g>pteridinetetrones as oxidation catalysts; Product distribution;
9.4%
With C42H60N6O4 (1c)
T=80°C; 25 h; Irradiationdifferent 1,3,8,10,11,14-hexapentaphene-2,4,7,9(14H,3H,8H,11H)tetraones and photosenzitizers; Product distribution;
Yoneda, Fumio; Koga, Masakazu; Ibuka, Toshiro; Yano, Yumihiko
Chemical & Pharmaceutical Bulletin, 1986 , vol. 34, # 6 p. 2653 - 2655 Title/Abstract Full Text Show Details
2.5%
With different mixed flavins
T=80°C; 25 h; sunlight; Product distribution;
Yoneda; Koga
Journal of Heterocyclic Chemistry, 1988 , vol. 25, # 2 p. 549 - 553 Title/Abstract Full Text View citing articles Show Details
With chromium(VI) oxide; sulfuric acid
Demjanow
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1910 , vol. 42, p. 840 Chem. Zentralbl., 1910 , vol. 81, # II p. 1749 Full Text View citing articles Show Details
Nagamatsu, Tomohisa; Matsumoto, Etsuko; Yoneda, Fumio
Chemistry Letters, 1982 , p. 1127 - 1130 Title/Abstract Full Text Show Details
50 % Chromat.
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium in benzene
T=80°C; 6 h;
Kaneda, Kiyotomi; Kawanishi, Yasuyuki; Jitsukawa, Koichiro; Teranishi, Shiichiro
Tetrahedron Letters, 1983 , vol. 24, # 45 p. 5009 - 5010 Title/Abstract Full Text View citing articles Show Details
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene
Heating; Yield given;
Minami, Ichiro; Yamada, Mitsuru; Tsuji, Jiro
Tetrahedron Letters, 1986 , vol. 27, # 16 p. 1805 - 1808 Title/Abstract Full Text View citing articles Show Details
96 % Chromat.
With lt;MoO(O2)2C5H4N(O)COOgt;Bu4N in 1,2-dichloro-ethane
T=50°C; 9 h;
Bortolini, O.; Campestrini, S.; Furia, F. Di; Modena, G.; Valle, G.
Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5467 - 5469 Title/Abstract Full Text View citing articles Show Details
With oxygen; dihydrogen hexachloroplatinate; copper dichloride
18.5 h; Ambient temperatureIrradiation; Yield given;
Cameron, Randy E.; Bocarsly, Andrew B.
Journal of the American Chemical Society, 1985 , vol. 107, # 21 p. 6116 - 6117 Title/Abstract Full Text View citing articles Show Details
94.3 % Chromat.
With tris(triphenylphosphine)ruthenium(II) chloride; potassium carbonate; acetophenone; acetone
Wang, G-Z.; Baeckvall, Jan-E.
Journal of the Chemical Society, Chemical Communications, 1992 , # 4 p. 337 - 339 Title/Abstract Full Text View citing articles Show Details
T=56°C; 1 h;
97 % Chromat.
With bis(quinuclidine)bromine(I) bromide; pyridinium trifluroacetate in dichloromethane; water
3 h; Ambient temperature;
Blair, Larry K.; Hobbs, Steven; Bagnoli, Nicholas; Husband, Leslie; Badika, Ndofunsu
Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1600 - 1603 Title/Abstract Full Text View citing articles Show Details
70 % Chromat.
With manganese(IV) oxide; potassium carbonate; [(η6-p-MeC6H4Pri)2Ru2Cl2(μ-Cl)2]; 2,6-Di-tertbutyl-1,4-benzoquinone in tetrahydrofuran
T=65°C; 20 h;
Karlsson, Ulrika; Wang, Guo-Zhi; Baeckvall, Jan-E.
Journal of Organic Chemistry, 1994 , vol. 59, # 5 p. 1196 - 1198 Title/Abstract Full Text View citing articles Show Details
in water
T=30°C; 120 h; culture medium containing Corynebacterium equi IFO 3730; Yield given;
Ohta, Hiromichi; Fujiwara, Hidenori; Tsuchihashi, Gen-ichi
Agricultural and Biological Chemistry, 1984 , vol. 48, # 2 p. 317 - 322 Title/Abstract Full Text Show Details
93 % Chromat.
With silver tetrafluoroborate; bis(quinuclidine)bromine(I) tetrafluoroborate in dichloromethane
0.166667 h;
Blair, Larry K.; Parris, Kevin D.; Lee, On Fai Daniel; Jenkins, Karen F.; Feese, Robin Chaney; et al.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5454 - 5456 Title/Abstract Full Text View citing articles Show Details
68 % Chromat.
With tert.-butylhydroperoxide; cetyltrimethylammonium chlorochromate in benzene
T=80°C; 2 h;
Agarwal, D. D.; Kaul, Anju; Raina, Daisy
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 158 - 160 Title/Abstract Full Text Show Details
With tert.-butylhydroperoxide; 3 A molecular sieve; Zr(OR)x; silica gel in tetrachloromethane; dichloromethane
T=80°C; 5 h; other catalyst: Zr(O-n-Pr)4;
Krohn, Karsten; Vinke, Ingeborg; Adam, Horst
Journal of Organic Chemistry, 1996 , vol. 61, # 4 p. 1467 - 1472 Title/Abstract Full Text View citing articles Show Details
72 % Chromat.
With dihydrogen peroxide; (cetylpyridinium)8CeW10O36 in chloroform
T=61°C; 16 h;
Shiozaki; Kominami; Kera
Synthetic Communications, 1996 , vol. 26, # 9 p. 1663 - 1668 Title/Abstract Full Text View citing articles Show Details
81 % Turnov.
With fluorine in acetonitrile
Chambers, Richard D.; Hutchinson, John; Sandford, Graham; Shah, Aneela; Vaughan, Julian F. S.
Tetrahedron, 1997 , vol. 53, # 46 p. 15833 - 15842 Title/Abstract Full Text View citing articles Show Details
T=50°C; secondary alcohol dehydrogenase (SADH) from Thermoanaerobacter ethanolicus, NADP, Tris*HCl buffer; Rate constant;
Pham; Phillips
Journal of the American Chemical Society, 1990 , vol. 112, # 9 p. 3629 - 3632 Title/Abstract Full Text View citing articles Show Details
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium(II)
effect of other catalysts and reagents were examined.; Product distributionMechanism;
Minami, Ichiro; Yamada, Mitsuru; Tsuji, Jiro
Tetrahedron Letters, 1986 , vol. 27, # 16 p. 1805 - 1808 Title/Abstract Full Text View citing articles Show Details
With 3,10-dimethyl-8-dimethylaminopyrimidolt;4,5-bgt;quinoline-2(3H),4(10H)-dione
T=120°C; 25 h; other 5-deazaflavins; Product distribution;
Yoneda, Fumio; Mori, Kenya; Sakuma, Yoshiharu; Koshiro, Akira
Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 945 - 947 Title/Abstract Full Text Show Details
With enzyme of Nicotiana tabacum in water
T=25°C; 2 h; correlation of the reaction rate with 13C NMR; Rate constantEquilibrium constant;
Suga, Takayuki; Izumi, Shunsuke; Hirata, Toshifumi
Chemistry Letters, 1986 , p. 2053 - 2056 Title/Abstract Full Text Show Details
With nicotinamide adenine dinucleotide; horse liver alcohol dehydrogenase in various solvent(s) T=25°C; pH 9; Rate constant;
Jones, J. Bryan; Schwartz, Harold M.
Canadian Journal of Chemistry, 1981 , vol. 59, p. 1574 - 1579 Title/Abstract Full Text Show Details
With ditellurato cuprate(III); ruthenium trichloride
T=31.9°C; in alkaline medium; KineticsRate constant;
Bal Reddy, K.; Sethuram, B.; Navaneeth Rao, T.
Bulletin des Societes Chimiques Belges, 1981 , vol. 90, # 10 p. 1017 - 1022 Title/Abstract Full Text Show Details
With perchloric acid; oxochromium(IV); lithium perchlorate in water
T=25°C; Rate constant;
Scott, Susannah L.; Bakac, Andreja; Espenson, James H.
Journal of the American Chemical Society, 1992 , vol. 114, # 11 p. 4205 - 4213 Title/Abstract Full Text View citing articles Show Details
With oxygen; dihydrogen hexachloroplatinate; copper dichloride
18.5 h; Ambient temperatureIrradiationvarious alcohols, various times; MechanismQuantum yield;
Cameron, Randy E.; Bocarsly, Andrew B.
Journal of the American Chemical Society, 1985 , vol. 107, # 21 p. 6116 - 6117 Title/Abstract Full Text View citing articles Show Details
With barium permanganate; hydroxide in water
T=34.9°C; various temperatures, different reagent concentrations; Ea, ΔH(excit.), ΔS(excit.); KineticsThermodynamic dataMechanism;
Pati, Subas C.; Dev, B. R.
Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1982 , vol. 21, # 2 p. 165 - 167 Title/Abstract Full Text Show Details
With lt;Ag(OH)2(H4TeO6)2gt;(3-); hydroxide
T=26.9°C; ΔE(excit.), ΔG(excit.), ΔH(excit.), ΔS(excit.); Thermodynamic dataMechanismKinetics;
Ravi Prasad, T.; Sethuram, B.; Navaneeth Rao, T.
Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1982 , vol. 21, # 2 p. 170 - 171 Title/Abstract Full Text Show Details
With potassium hydroxide; Cu(OH)2(H4TeO6); tellurate
T=9.4°C; other temperatures and concentrations, catalysis by OsO4; KineticsMechanism;
Reddy, K. Bal; Murthy, C. P.; Sethuram, B.; Navaneeth Rao, T.
Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981 , vol. 20, # 3 p. 272 - 275 Title/Abstract Full Text Show Details
With ruthenium trichloride; perchloric acid; mercury(II) diacetate; bromate in water
T=60°C; other temperatures and solvent; ΔE, ΔH and ΔS(excit.); KineticsMechanismThermodynamic data;
Radhakrishnamurti, P. S.; Sarangi, L. D.
Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981 , vol. 20, # 3 p. 301 - 303 Title/Abstract Full Text Show Details
With sulfuric acid; mercury(II) diacetate; saccharin in water; acetic acid
T=45°C; var. concn. of substrate, saccharin, sulphuric acid; MechanismThermodynamic dataRate constant;
Mohan, K. Vijaya; Rao, P. Raghunath; Sundaram, E. V.
Journal of the Indian Chemical Society, 1984 , vol. 61, # 10 p. 876 - 879 Title/Abstract Full Text Show Details
With N-chlorosaccharin; sulfuric acid in water; acetic acid
T=44.9°C; effect of N-chlorosaccharin concentration; effect of cycloalkanol concentration; effect of acid concentration; effect of solvent composition; ΔE, ΔH(act.), ΔS(act.), ΔG(act.); KineticsThermodynamic dataEquilibrium constant;
Mohan, K. Vijaya; Rao, P. Raghunatha; Sundaram, E. V.
Journal of the Indian Chemical Society, 1986 , vol. 63, p. 698 - 700 Title/Abstract Full Text Show Details
With bromamine T in perchloric acid
T=35°C; mechanism; effect of concentrations, ionic strength and solvent composition; solvent isotope effect; Rate constantKineticsThermodynamic data;
Singh, Bharat; Singh, A. K.
Journal of the Indian Chemical Society, 1985 , vol. 62, # 7 p. 523 - 525 Title/Abstract Full Text Show Details
With lt;MoO(O2)2(C5H4NOCOO)gt;-Bu4N+ in 1,2-dichloro-ethane
T=50°C; Rate constant;
Campestrini, Sandro; Di Furia, Fulvio
Tetrahedron, 1994 , vol. 50, # 17 p. 5119 - 5130 Title/Abstract Full Text View citing articles Show Details
With 12-butyl-3-methyl-14-octyl-9-phenyl-3,9-dihydro-1,3,9,11,12,14-hexazapentacene-2,4,8,10tetraone
T=10 - 15°C; 24 h; Irradiationvar. of reagent, temp.; Product distribution;
Yoneda, Fumio; Kuroda, Kazunori; Koga, Masakazu; Ibuka, Toshiro
Journal of the Chemical Society, Chemical Communications, 1984 , # 13 p. 872 - 873 Title/Abstract Full Text View citing articles Show Details
With sodium hydroxide; NAD; glycine
T=25°C; 2 h; Equilibrium constantRate constant;
Izumi, Shunsuke; Suga, Takayuki
Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 5 p. 1715 - 1720 Title/Abstract Full Text Show Details
With dipotassium peroxodisulfate; silver nitrate in water
T=35°C; further temperatures; also K2SO4; Ea, ΔG(excit.), ΔH(excit.), ΔS(excit.), various concentrations of cyclopentanol and reagent; Rate constantThermodynamic dataMechanism;
Srivastava, S. P.; Gupta, V. K.; Sharma, R. G.; Singh, B. P.
Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981 , vol. 20, # 12 p. 1221 - 1223 Title/Abstract Full Text Show Details
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; hypochlorite; sodium bromide in water
T=1.5°C; pH 10; with/without TEMPO; Rate constant;
De Nooy; De Nooy, Arjan E. J.; Besemer; Besemer, Arie C.; Van Bekkum; Van Bekkum, Herman
Tetrahedron, 1995 , vol. 51, # 29 p. 8023 - 8032 Title/Abstract Full Text View citing articles Show Details
With tert.-butylhydroperoxide; 3 A molecular sieve; zircornium(IV) n-propoxide in tetrachloromethane
T=20°C; 3.5 h; initial reaction rate, 50percent conversion reaction time, other primary and secondary alcohols, other catalysts, other solvents, other reaction temperatures and times; Mechanism;
Krohn, Karsten; Vinke, Ingeborg; Adam, Horst
Journal of Organic Chemistry, 1996 , vol. 61, # 4 p. 1467 - 1472 Title/Abstract Full Text View citing articles Show Details
With sulfuric acid; quinolinium dichromate(VI) in N,N-dimethyl-formamide
T=49.9°C; var. temp, var. catalyst; ΔH(excit.), ΔS(excit.), ΔG(excit.); Rate constantThermodynamic data;
Nongkynrih, Irona; Mahanti, Mahendra K.
Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 5 p. 1403 - 1407 Title/Abstract Full Text View citing articles Show Details
With chromium(VI) oxide; sodium dodecyl-sulfate in water
T=35°C; ΔH(excit.), -ΔS(excit.); var. temperature; Rate constantThermodynamic data;
Sahu; Panigrahi
Journal of the Indian Chemical Society, 1996 , vol. 73, # 11 p. 576 - 579 Title/Abstract Full Text View citing articles Show Details
90 % Chromat.
With air; cryptomelan H-K-OMS-2 in toluene
T=110°C; 4 h;
Son, Young-Chan; Makwana, Vinit D.; Howell, Amy R.; Suib, Steven L.
Angewandte Chemie - International Edition, 2001 , vol. 40, # 22 p. 4280 - 4283 Title/Abstract Full Text View citing articles Show Details
With cis-[Os(VIII)O4(OH)2](2-); [Fe(CN)6](3-); acetonitrile
Griffith; Suriaatmaja
T=20°C; 2 h;
Canadian Journal of Chemistry, 2001 , vol. 79, # 5-6 p. 598 - 606 Title/Abstract Full Text View citing articles Show Details
100 % Spectr.
With pentamethylcyclopentadienyliridium dichloride; potassium carbonate in acetone
T=20°C; 6 h;
Fujita, Ken-Ichi; Furukawa, Shigetoyo; Yamaguchi, Ryohei
Journal of Organometalic Chemistry, 2002 , vol. 649, # 2 p. 289 - 292 Title/Abstract Full Text View citing articles Show Details
With cyclic alcohol dehydrogenase from Gluconobacter frateurii
T=25°C; pH=5.0; Enzyme kinetics;
Moonmangmee; Fujii; Toyama; Theeragool; Lotong; Matsushita; Adachi
Bioscience, biotechnology, and biochemistry, 2001 , vol. 65, # 12 p. 2763 - 2772 Title/Abstract Full Text View citing articles Show Details
99 % Chromat.
With mukaiyama’s reagent; 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane
T=20°C; 0.5 h;
Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki
Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 2 p. 223 - 234 Title/Abstract Full Text View citing articles Show Details
With whole cells of Rhodococcus ruber DSM 44541; acetone in phosphate buffer
T=24°C; Oppenauer oxidation; pH=8.0;
Stampfer, Wolfgang; Kosjek, Birgit; Moitzi, Christian; Kroutil, Wolfgang; Faber, Kurt
Angewandte Chemie (International ed. in English), 2002 , vol. 41, # 6 p. 1014 - 1017 Title/Abstract Full Text View citing articles Show Details
96 % Chromat.
With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide; TEMPO-linked 5,10,15,20-tetraphenyl-Mn-porphyrin in dichloromethane
T=0°C; pH=8.6; 0.5 h;
Huang, Jian-Ying; Li, Shi-Jun; Wang, Yan-Guang
Tetrahedron Letters, 2006 , vol. 47, # 32 p. 5637 - 5640 Title/Abstract Full Text View citing articles Show Details
With potassium bromate; perchloric acid; mercury(II) diacetate; iridium(III) chloride
T=34.85°C; Kinetics; Further Variations:Temperatures;
Srivastava, Sheila; Sharma, Rajendra Kumar; Singh, Sarika
Journal of the Indian Chemical Society, 2006 , vol. 83, # 3 p. 282 - 287 Title/Abstract Full Text View citing articles Show Details
With perchloric acid; mercury(II) diacetate; N-bromoacetamide; ruthenium trichloride in water
T=35°C; 48 h; Kinetics; Further Variations:TemperaturesReagents;
Srivastava, Sheila; Awasthi, Ajaya; Singh, Kulina
International Journal of Chemical Kinetics, 2005 , vol. 37, # 5 p. 275 - 281 Title/Abstract Full Text View citing articles Show Details
With 2,6-dichloropyridine N-oxide; EDMA; Ru(II)(CO)(meso-(4-vinylC6H4)4porphyrinate); hydrogen bromide in benzene
T=55°C; 3 h; Product distribution; Further Variations:Reagents;
Nestler, Oliver; Severin, Kay
Organic Letters, 2001 , vol. 3, # 24 p. 3907 - 3909 Title/Abstract Full Text View citing articles Show Details
With oxygen; aluminum oxide; ruthenium in various solvent(s) T=82.84°C; 8 h;
Yamaguchi, Kazuya; Mizuno, Noritaka
Chemistry - A European Journal, 2003 , vol. 9, # 18 p. 4353 - 4361 Title/Abstract Full Text View citing articles Show Details
84 % Chromat.
With oxygen; hydroxyapatite-bound Pd in various solvent(s) T=90°C; 24 h;
Mori, Kohsuke; Yamaguchi, Kazuya; Hara, Takayoshi; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi
Journal of the American Chemical Society, 2002 , vol. 124, # 39 p. 11572 - 11573 Title/Abstract Full Text View citing articles Show Details
92 % Chromat.
With dihydrogen peroxide; [MoO(O2)2(TEDA)2] in water
T=80°C; 8 h;
Luan, Yi; Wang, Ge; Luck, Rudy L.; Yang, Mu; Han, Xiao
Chemistry Letters, 2007 , vol. 36, # 10 p. 1236 - 1237 Title/Abstract Full Text View citing articles Show Details
With oxygen in 2,3,4-trifluorotoluene
T=20 - 83°C; 8 h; Conversion of starting material; Hide Experimental Procedure
Mizuno, Noritaka; Yamaguchi, Kazuya; Ishida, Hajime
Patent: US2004/204597 A1, 2004 ; Location in patent: Page 5 ; Title/Abstract Full Text Show Details
20:Example 20
The same procedures as in Example 17 were repeated except that cyclopentanol was used as a substrate in place of cyclohexanol. The conversion of cyclopentanol was 92percent, and the selectivity to cyclopentanone was more than 99percent. 97.1 % Chromat.
With oxygen; Pt-GLY in water
T=80°C; P=760.051 Torr; 24 h;
Wang, Tao; Xiao, Chao-Xian; Yan, Liang; Xu, Lin; Luo, Jie; Shou, Heng; Kou, Yuan; Liu, Haichao
Chemical Communications, 2007 , # 42 p. 4375 - 4377 Title/Abstract Full Text View citing articles Show Details
With oxygen in toluene
Wang, Feng; Ueda, Wataru
T=79.84°C; P=760.051 Torr; 24 h;
Chemistry Letters, 2008 , vol. 37, # 2 p. 184 - 185 Title/Abstract Full Text View citing articles Show Details
90 %Chromat.
With α,α,α-trifluorotoluene; oxygen in water
T=20°C; 115 h;
Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu
Chemical Communications, 2008 , # 17 p. 2031 - 2033 Title/Abstract Full Text View citing articles Show Details
57 %Chromat.
With α,α,α-trifluorotoluene; water; oxygen; potassium carbonate
T=30°C; P=760.051 Torr; 48 h; Kinetics; Time;
Lucchesi, Celine; Inasaki, Takeshi; Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu
Advanced Synthesis and Catalysis, 2008 , vol. 350, # 13 p. 1996 - 2000 Title/Abstract Full Text View citing articles Show Details
With 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux;
Singh, Pradhumn; Singh, Monika; Singh, Ajai K.
Journal of Organometallic Chemistry, 2009 , vol. 694, # 24 p. 3872 - 3880 Title/Abstract Full Text View citing articles Show Details
95 %Chromat.
With NaAuCl4; oxygen; caesium carbonate in toluene
T=30°C; P=760.051 Torr; 30 h;
Karimi, Babak; Kabiri Esfahani, Farhad
Chemical Communications, 2009 , # 37 p. 5555 - 5557 Title/Abstract Full Text View citing articles Show Details
With Oxonereg;; tetrabutylammomium bromide in water
T=20°C; 1 h; Irradiation;
Wu, Shang; Ma, Hengchang; Yan, Penghua; Wang, Jianqiang; Ding, Juanjuan; Lei, Ziqiang
Letters in Organic Chemistry, 2009 , vol. 6, # 5 p. 424 - 427 Title/Abstract Full Text View citing articles Show Details
With potassium bromate; rhodium(III) chloride; potassium chloride; mercury(II) diacetate; sodium hydroxide in water
T=35°C; Kinetics; Temperature;
Srivastava, Sheila; Srivastava, Parul; Chaudhary, Lakshmi; Kumar, Ashish; Singh, Shalini
Journal of the Indian Chemical Society, 2009 , vol. 86, # 1 p. 58 - 62 Title/Abstract Full Text View citing articles Show Details
70 %Chromat.
With Ag/HT in toluene
T=110°C; 24 h; Inert atmosphere; Hide Experimental Procedure
Kaneda, Kiyotomi; Yamasaki, Noritsugu
Patent: US2010/130758 A1, 2010 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details
2-1:
Example 2-1 A mixture of 1 mmol of cyclopentanol, 5 mL of toluene, and 0.1 g of the catalyst prepared from Example 2-0 and including Ag particles immobilized on a hydrotalcite surface was stirred at 110° C. in an argon atmosphere for 24 hours and thereby yielded a corresponding carbonyl compound (cyclopentanone) in a yield equivalent to a gas chromatographic (GC) yield of 70percent, with a selectivity for chclopentanone of 99percent or more.
With [ruthenium(II)chloride(.eta.6-p-cymene)(1-(4-methoxyphenyltelluromethyl)-1Hbenzotriazole)](hexaflourophosphate); 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux;
Das, Dipanwita; Singh, Pradhumn; Singh, Ajai K.
Journal of Organometallic Chemistry, 2010 , vol. 695, # 7 p. 955 - 962 Title/Abstract Full Text View citing articles Show Details
85 %Chromat.
With NiZn-Pd(0.02) nanocomposite catalyst in α,α,α-trifluorotoluene
T=99.84°C; P=760.051 Torr; 12 h;
Hara, Takayoshi; Ishikawa, Masakazu; Sawada, Junya; Ichikuni, Nobuyuki; Shimazu, Shogo
Green Chemistry, 2009 , vol. 11, # 12 p. 2034 - 2040 Title/Abstract Full Text View citing articles Show Details
With oxygen in water
T=85°C; P=750.075 Torr; 3 h;
Yang, Xiaomin; Wang, Xiuna; Qiu, Jieshan
Applied Catalysis A: General, 2010 , vol. 382, # 1 p. 131 - 137 Title/Abstract Full Text View citing articles Show Details
100 %Chromat.
With dihydrogen peroxide in water
T=89.84°C; 8 h;
Ma, Baochun; Zhang, Yingshuai; Ding, Yong; Zhao, Wei
Catalysis Communications, 2010 , vol. 11, # 9 p. 853 - 857 Title/Abstract Full Text View citing articles Show Details
With (TSPP)Rh(III)(H2O)2; oxygen; sodium hydroxide in water
T=80°C; P=760.051 Torr;
Liu, Lianghui; Yu, Mengmeng; Wayland, Bradford B.; Fu, Xuefeng
Chemical Communications, 2010 , vol. 46, # 34 p. 6353 - 6355 Title/Abstract Full Text View citing articles Show Details
With C22H23NRuSSe(2+)*2F6P(1-); 4-methylmorpholine N-oxide in dichloromethane
2 h; Reflux;
Singh, Pradhumn; Das, Dipanwita; Singh, Monika; Singh, Ajai K.
Inorganic Chemistry Communications, 2010 , vol. 13, # 2 p. 223 - 226 Title/Abstract Full Text View citing articles Show Details
With oxygen in water
Ma, Zhancheng; Yang, Hengquan; Qin, Yong; Hao, Yajuan; Li, Guang
T=60°C; 12 h;
Journal of Molecular Catalysis A: Chemical, 2010 , vol. 331, # 1-2 p. 78 - 85 Title/Abstract Full Text View citing articles Show Details
With C52H43N3O4P2RuS; 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux;
Ulaganatha Raja; Gowri; Ramesh
Polyhedron, 2010 , vol. 29, # 3 p. 1175 - 1181 Title/Abstract Full Text View citing articles Show Details
100 %Chromat.
With oxygen in α,α,α-trifluorotoluene; water
T=20°C; P=760.051 Torr; 24 h;
Kaizuka, Kosuke; Miyamura, Hiroyuki; Kobayashi, Shu
Journal of the American Chemical Society, 2010 , vol. 132, # 43 p. 15096 - 15098 Title/Abstract Full Text View citing articles Show Details
93 %Chromat.
With hydrotalcite-supported gold nanoparticles (Au/HT); air in toluene
T=40°C; P=760.051 Torr; 36 h;
Mitsudome, Takato; Noujima, Akifumi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi
Advanced Synthesis and Catalysis, 2009 , vol. 351, # 11-12 p. 1890 - 1896 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide; acetic acid; sodium bromide in water
T=60°C; 4 h;
Qi, Xingyi; Wang, Jing; Zheng, Liwei; Qi, Lin
Synlett, 2011 , # 4 art. no. W17410ST, p. 555 - 558 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in 1,4-dioxane; water
T=85°C; 7 h;
Ding, Yong; Zhao, Wei
Journal of Molecular Catalysis A: Chemical, 2011 , vol. 337, # 1-2 p. 45 - 51 Title/Abstract Full Text View citing articles Show Details
With [ruthenium(II)chloride(.eta.6-benzene)(N-[2-(phenylseleno)ethyl]morpholine)] (hexafluorophosphate); 4-methylmorpholine N-oxide in dichloromethane
3 h; Reflux;
Singh, Pradhumn; Singh, Ajai K.
European Journal of Inorganic Chemistry, 2010 , # 26 p. 4187 - 4195 Title/Abstract Full Text View citing articles Show Details
With oxygen in toluene
T=80°C; P=760.051 Torr; 3 h;
Yamaguchi, Kazuya; Kim, Jung Won; He, Jinling; Mizuno, Noritaka
Journal of Catalysis, 2009 , vol. 268, # 2 p. 343 - 349 Title/Abstract Full Text View citing articles Show Details
Stage #1: With potassium hydride in acetonitrile
Zhu, Xiao-Qing; Chen, Xi; Mei, Lian-Rui
Organic Letters, 2011 , vol. 13, # 9 p. 2456 - 2459 Title/Abstract Full Text View citing articles Show Details
Stage #2: With 4-acetylamino-2,2,6,6-tetramethyl-piperidine-1-oxoam-monium perchlorate in acetonitrile
T=20°C; 3 h;
With dihydrogen peroxide in water
0.833333 h; Microwave irradiation;
Carraro, Mauro; Nsouli, Nadeen; Oelrich, Holger; Sartorel, Andrea; Soraru, Antonio; Mal, Sib Sankar; Scorrano, Gianfranco; Walder, Lorenz; Kortz, Ulrich; Bonchio, Marcella
Chemistry - A European Journal, 2011 , vol. 17, # 30 p. 8371 - 8378 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in water
T=90°C; 1 h;
Xie, Ting; Lu, Min; Zhang, Wenwen; Li, Jun
Journal of Chemical Research, 2011 , vol. 35, # 7 p. 397 - 399 Title/Abstract Full Text View citing articles Show Details
35 %Chromat.
With periodic acid in water
T=27°C; 24 h; chemoselective reaction;
Babu, S. Ganesh; Priyadarsini, P. Aruna; Karvembu
Applied Catalysis A: General, 2011 , vol. 392, # 1-2 p. 218 - 224 Title/Abstract Full Text View citing articles Show Details
With tert.-butylhydroperoxide in acetonitrile
T=89.84°C; 24 h;
Gao, Yongjun; Ma, Ding; Hu, Gang; Zhai, Peng; Bao, Xinhe; Zhu, Bo; Zhang, Bingsen; Su, Dang Sheng
Angewandte Chemie - International Edition, 2011 , vol. 50, # 43 p. 10236 - 10240 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in water
T=84.84°C; 8 h;
Zhao, Wei; Ding, Yong; Ma, Baochun; Qiu, Wenyuan
Synthetic Communications, 2012 , vol. 42, # 4 p. 554 - 562 Title/Abstract Full Text View citing articles Show Details
87 %Chromat.
With oxygen; potassium carbonate in α,α,α-trifluorotoluene
T=95°C; 10 h;
Karimi, Babak; Elhamifar, Dawood; Clark, James H.; Hunt, Andrew J.
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 21 p. 7420 - 7426 Title/Abstract Full Text View citing articles Show Details
93 %Chromat.
With C51H51ClN2O2P2RuS; 4-methylmorpholine N-oxide in acetonitrile
T=27°C; 12 h;
Gunasekaran; Remya; Radhakrishnan; Karvembu
Journal of Coordination Chemistry, 2011 , vol. 64, # 3 p. 491 - 501 Title/Abstract Full Text View citing articles Show Details
With 2C2H6O*C38H26CoN6S2(2+)*H2O*2NO3(1-); dihydrogen peroxide in water
T=20°C; 8 h; chemoselective reaction;
Nemati Kharat, Ali; Bakhoda, Abolghasem; Tamaddoni Jahromi, Bahareh
Polyhedron, 2011 , vol. 30, # 17 p. 2768 - 2775 Title/Abstract Full Text View citing articles Show Details
86 %Spectr.
With potassium carbonate in acetone
T=65°C; 8 h; Kinetics; Reagent/catalyst;
Terashima, Takaya; Ouchi, Makoto; Ando, Tsuyoshi; Sawamoto, Mitsuo
Journal of Polymer Science, Part A: Polymer Chemistry, 2011 , vol. 49, # 5 p. 1061 - 1069 Title/Abstract Full Text View citing articles Show Details
90 %Chromat.
With tert.-butylhydroperoxide; [Co(III)(N-(dibenzylcarbamothioyl)benzamide(-H))3] in acetonitrile
T=80°C; 30 h;
Gunasekaran; Jerome; Ng, Seik Weng; Tiekink, Edward R.T.; Karvembu
Journal of Molecular Catalysis A: Chemical, 2012 , vol. 353-354, p. 156 - 162 Title/Abstract Full Text View citing articles Show Details
With sodium chlorite; cis-[Ru(2,9-dimethyl-1,10-phenanthroline)2(OH2)2]2+
T=22.84°C; pH=6.8; aq. phosphate buffer;
Hu, Zongmin; Du, Hongxia; Man, Wai-Lun; Leung, Chi-Fai; Liang, Haojun; Lau, Tai-Chu
Chemical Communications, 2012 , vol. 48, # 8 p. 1102 - 1104 Title/Abstract Full Text View citing articles Show Details
With Ru[(.eta.6-p-cumene)(AsPh3)(C5H4NC(S)NC6H2(CH3)3)]BPh4; 4-methylmorpholine Noxide in dichloromethane
T=40°C; 10 h; Hide Experimental Procedure
Raja, M. Ulaganatha; Ramesh
Journal of Organometallic Chemistry, 2012 , vol. 699, p. 5 - 11 Title/Abstract Full Text View citing articles Show Details
2.6. Catalytic oxidation
General procedure: Catalytic oxidation of primary alcohols to the corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) carbonyl complexes was studied in the presence of NMO as co-oxidant. A typical reaction using the complex [Ru(η6-p-cymene)(AsPh3)(L4)] (4) as a catalyst and primary or secondary alcohol as substrates at a 1:100 M ratio is described as follows. A solution of ruthenium complex (4) (0.01 mmol) in 20 cm3 CH2Cl2 was added to the solution of substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 3-10 h and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with diethyl ether (20 cm3) and was analyzed by GC and 1H NMR. The oxidized products were determined by GC and 1H NMR by comparison with authentic samples and no internal standards were used. 88 %Chromat.
With [Ru(S(C6H4)NCH(C6H4)O(Br))(CO)(PPh3)2]; 4-methylmorpholine N-oxide in dichloromethane
T=27°C; 12 h; Hide Experimental Procedure
Muthu Tamizh; Mereiter; Kirchner; Karvembu
Journal of Organometallic Chemistry, 2012 , vol. 700, p. 194 - 201 Title/Abstract Full Text View citing articles Show Details
2.5. Catalytic oxidation of alcohols
General procedure: To a solution of alcohol (1 mmol) in dichloromethane (20 mL),ruthenium(II) complex (1 molpercent) and NMO (351 mg; 3 mmol) were added. The mixture was stirred at 27 °C for 12 h. Then the solution was concentrated and the alcohol and aldehyde/ketone were obtained by passing the solution through a short silica gel column (hexane/ethyl acetate). The extract was then analyzed by GC. 86 %Chromat.
With [Cp*Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)](OTf)2 in water; tert-butyl alcohol
20 h; Inert atmosphereReflux;
Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei
Journal of the American Chemical Society, 2012 , vol. 134, # 8 p. 3643 - 3646 Title/Abstract Full Text View citing articles Show Details
With oxygen; benzaldehyde
T=110°C; 16 h; Neat (no solvent);
Kuang, Yongbo; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki
Applied Catalysis A: General, 2012 , vol. 423-424, p. 52 - 58 Title/Abstract Full Text View citing articles Show Details
95 %Chromat.
With oxygen; caesium carbonate in toluene
T=20°C; 24 h;
Karimi, Babak; Esfahani, Farhad Kabiri
Advanced Synthesis and Catalysis, 2012 , vol. 354, # 7 p. 1319 - 1326 Title/Abstract Full Text View citing articles Show Details
76 %Chromat.
With 3-(3-(1,2-dicarboxyethylamino)-3-oxopropyl)-1-methyl-1H-imidazol-3-ium bromide; dihydrogen peroxide
T=25°C; 1.33333 h; Neat (no solvent);
Karthikeyan, Parasuraman; Arunrao, Aswar Sachin; Narayan, Muskawar Prashant; Kumar, Sythana Suresh; Kumar, S. Senthil; Bhagat, Pundlik Rambhau
Journal of Molecular Liquids, 2012 , vol. 173, p. 180 - 183 Title/Abstract Full Text View citing articles Show Details
86 %Chromat.
With C17H14Cl2N4O2Ru; 4-methylmorpholine N-oxide in dichloromethane
1 h; Molecular sieveReflux; Hide Experimental Procedure
Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan
Journal of Organometallic Chemistry, 2012 , vol. 716, p. 129 - 137 Title/Abstract Full Text View citing articles Show Details
3.4 Procedure for catalytic oxidation of alcohols
General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO, H2O2 or ButOOH as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2Cl2(α-NaiEt)] (1b) (0.01 mmol) in CH2Cl2 (20 ml) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 1 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 ml), concentrated to ≈1 ml and was analyzed by GC. The oxidation products were identified by GC co-injection with authentic samples. All other alcohols were oxidized following identical reaction protocol.
With H4N(1+)*Zn2Sb2; dihydrogen peroxide in water
Ni, Lubin; Patzke, Greta R.; Patscheider, Joerg; Baldridge, Kim K.
T=85°C; 7 h;
Chemistry--A European Journal, 2012 , vol. 18, # 42 p. 13293 - 13298,6 Title/Abstract Full Text Show Details
Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.
Chemistry - A European Journal, 2012 , vol. 18, # 42 p. 13293 - 13298 Title/Abstract Full Text View citing articles Show Details
98 %Chromat.
With [bis(acetoxy)iodo]benzene; [Al(OH)(bpydc)·0.07RuCl3(DMSO)·0.5H2O] in dichloromethane
T=40°C; 3.5 h; Sealed tube; Catalytic behavior;
Carson, Fabian; Agrawal, Santosh; Gustafsson, Mikaela; Bartoszewicz, Agnieszka; Moraga, Francisca; Zou, Xiaodong; Martin-Matute, Belen
Chemistry - A European Journal, 2012 , vol. 18, # 48 p. 15337 - 15344 Title/Abstract Full Text View citing articles Show Details
With 2O34W9Zn(12-)*24H2O*10H4N(1+)*4Zn(2+)*2Sb(3+); dihydrogen peroxide in water
T=85°C; 7 h; Reagent/catalyst;
Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.
Chemistry - A European Journal, 2012 , vol. 18, # 42 p. 13293 - 13298 Title/Abstract Full Text View citing articles Show Details
With O32W10(4-)*4C9H14N(1+); dihydrogen peroxide in water
T=80°C; 8 h;
Liu, Dan; Gui, Jianzhou; Lu, Feng; Sun, Zhaolin; Park, Yong-Ki
Catalysis Letters, 2012 , vol. 142, # 11 p. 1330 - 1335 Title/Abstract Full Text View citing articles Show Details
100 %Chromat.
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane
T=120°C; 20 h; Solvent;
Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei
Angewandte Chemie - International Edition, 2012 , vol. 51, # 51 p. 12790 - 12794 Angew. Chem., 2012 , p. 12962 - 12966 Title/Abstract Full Text View citing articles Show Details
Stage #1: in dichloromethane
T=10°C; 0.05 h; Sonication; Stage #2: With sodium hypochlorite; sodium bromide in dichloromethane; water
T=10°C; pH=9.1; 0.116667 h;
Zheng, Zhi; Wang, Jianli; Zhang, Miao; Xu, Lixin; Ji, Jianbing
ChemCatChem, 2013 , vol. 5, # 1 p. 307 - 312 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in water
T=90°C; 7 h; Reflux;
Zhang, Zhenxin; Zhu, Qianqian; Ding, Yong
Synthetic Communications, 2013 , vol. 43, # 9 p. 1211 - 1218 Title/Abstract Full Text View citing articles Show Details
With C11H7I2N3O2RuS; 4-methylmorpholine N-oxide in dichloromethane
T=400°C; 2 h; Molecular sieve; Reagent/catalyst; Hide Experimental Procedure
Kundu, Subhankar; Sarkar, Deblina; Jana, Mahendra Sekhar; Pramanik, Ajoy Kumar; Jana, Subrata; Mondal, Tapan Kumar
Journal of Molecular Structure, 2013 , vol. 1035, p. 277 - 284 Title/Abstract Full Text View citing articles Show Details
4.7 Procedure for catalytic oxidation of alcohols
General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO as cooxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2(L)Cl2] (1) (0.01 mmol) in CH2Cl2 (25 mL) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 2 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 mL), concentrated to ≈1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 μm film thickness. The column, injector and detector temperatures were 200, 250 and 250 °C, respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 mL. The oxidation products were identified by GC co injection with authentic samples. All other alcohols were oxidized following identical reaction protocol. 94 %Chromat.
With trans-(Cl)-[Ru(CO)2Cl2(1-ethyl-2-(phenylazo)imidazole)]; 4-methylmorpholine N-oxide in dichloromethane
2 h; RefluxMolecular sieve; Reagent/catalyst; Hide Experimental Procedure
Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan
Polyhedron, 2013 , vol. 50, # 1 p. 246 - 254 Title/Abstract Full Text View citing articles Show Details
3.4. Procedure for catalytic oxidation
General procedure: Catalytic oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones respectively by ruthenium(II) and osmium(II) carbonyl iodide complexes were studied in the presence of NMO as a co-oxidant and the byproduct, water, was removed by using about 0.5 g of molecular sieves. Typical reactions were carried out using the ruthenium and osmium complexes as the catalyst and benzyl alcohol, 2-butanol, cyclopentanol and cyclohexanol as substrates in a 1:100 molar ratio. Solutions of the ruthenium and osmium complexes (0.01 mmol) in 20 cm3 CH2Cl2 were added to a solution of the substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 2 h and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with petroleum ether (20 cm3) and was analyzed by GC using an Agilent 7890 series Gas chromatography instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 lm film thickness. The ether extracts were evaporated to give the corresponding aldehydes/ketones, which were then isolated and quantified as their 2,4-dinitrophenylhydrazone derivatives. 99 %Chromat.
With sodium bromate; cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 in water
T=23°C; 10 h;
Hu, Zongmin; Ma, Li; Xie, Jianhui; Du, Hongxia; Lam, William W. Y.; Lau, Tai-Chu
New Journal of Chemistry, 2013 , vol. 37, # 6 p. 1707 - 1710 Title/Abstract Full Text View citing articles Show Details
94.4 %Chromat.
With tert.-butylhydroperoxide; Cu(9-(2'-hydroxy-3'-phenylthio-5'-tert-butylphenyl)-6-methylthio-3acetyl-5,7,8-triazanona-3,6,8-trien-2-one(2-)) in water
T=80°C; 4 h; Microwave irradiation; Reagent/catalyst;
Arion, Vladimir B.; Platzer, Sonja; Rapta, Peter; Machata, Peter; Breza, Martin; Vegh, Daniel; Dunsch, Lothar; Telser, Joshua; Shova, Sergiu; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.
Inorganic Chemistry, 2013 , vol. 52, # 13 p. 7524 - 7540 Title/Abstract Full Text View citing articles Show Details
91 %Chromat.
With oxygen in toluene
T=79.84°C; P=760.051 Torr; 3 h; Hide Experimental Procedure
Yoshida, Akihiro; Mori, Yoshinori; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi
Catalysis Today, 2013 , vol. 203, p. 153 - 157 Title/Abstract Full Text View citing articles Show Details
Procedures for catalytic oxidation
General procedure: The oxidation reaction was done in the following procedure:187 mg of the reduced 2 wtpercent Ir/TiO2 (Ir: 20 mol, 1.25 molpercent tosubstrates), the solvent (toluene or mesitylene, 1.5 mL), and thesubstrate (1.5 mmol) were charged into a glass vial (17 mL). Thereaction was started by stirring the reaction mixture at 353 K inalcohol oxidation or 423 K in xanthene oxidation under molecularoxygen at atmospheric pressure. The products were identified by comparison of the mass and NMR spectra with those of authenticsamples. The yields of the products were determined using GCanalyses with an internal standard technique.
With [ruthenium(II)(η6-benzene)(chloride)(NC5H4CH2SC6H5)](hexafluorophosphate); 4methylmorpholine N-oxide in dichloromethane
3 h; Reflux; Reagent/catalystTime;
Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham Lal; Singh, Ajai K.
Dalton Transactions, 2013 , vol. 42, # 24 p. 8736 - 8747 Title/Abstract Full Text View citing articles Show Details
With Pt#Bi2O3; oxygen in water
T=90°C; P=750.075 Torr; 5 h; Autoclave;
Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Ma, Hong; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 8 p. 2215 - 2221 Title/Abstract Full Text View citing articles Show Details
89.9 %Chromat.
With ruthenium(III) chloride trihydrate; trichloroisocyanuric acid; tetrabutylammomium bromide; potassium carbonate in water; ethyl acetate
T=25 - 45°C; 3 h; Green chemistry;
Yamaoka, Hidenori; Moriya, Narimasa; Ikunaka, Masaya
Organic Process Research and Development, 2004 , vol. 8, # 6 p. 931 - 938 Title/Abstract Full Text View citing articles Show Details
80 %Chromat.
With tert.-butylhydroperoxide in acetonitrile
T=75°C; Hide Experimental Procedure
Yadav, Ganapati D.; Yadav, Akhilesh R.
Journal of Molecular Catalysis A: Chemical, 2013 , vol. 380, p. 70 - 77 Title/Abstract Full Text View citing articles Show Details
General procedure: All experiments were conducted in 50 cm3 glass reactor. A fourbladed–pitched turbine impeller was used for reaction. The temperature was maintained at the selected value. Weighed quantitiesof reactants and catalyst were charged to the reactor and then the temperature raised to the desired value. Thereafter the agitation was commenced. An initial sample was taken and further sampling was done periodically up to 4 h. A standard experiment was performed with 0.01 mol 1-phenylethanol, 0.03 mol TBHP and catalyst quantity of 0.012 g/cm3. The temperature was normally maintainedat 75°C at 900 rpm as speed of agitation. The total volume of liquidphase was 15.0 cm3in which 0.2 cm3 n-decane was used as internal standard. At the end of experiment, the catalyst was filtered and the organic layer was concentrated and purified by columnchromatography.
Hide Details
With C14H14I2N2O4RuS; 4-methylmorpholine N-oxide in dichloromethane
T=40°C; 1 h; Molecular sieve; Reagent/catalyst; Hide Experimental Procedure
Jana, Subrata; Jana, Mahendra Sekhar; Sarkar, Deblina; Paira, Mrinal Kanti; Mondal, Tapan Kumar
Journal of Molecular Structure, 2013 , vol. 1054-1055, p. 83 - 88 Title/Abstract Full Text View citing articles Show Details
Procedure for catalytic oxidation of alcohols
General procedure: Catalytic oxidation of primary alcohols to corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) complexes were studied in the presence of NMO as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 M ratio was described as follows. A solution of complex 1 (0.01 mmol) in CH2Cl2 (25 mL) wasadded to the mixture containing PhCH2OH (1 mmol), NMO(3 mmol) and molecular sieves. The reaction mixture was refluxedand conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10 min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to 1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 mlength, 0.53 mm diameter and 5.00 lm film thickness. The column,injector and detector temperatures were 200, 250 and 250 C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 lL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50 min. Allother alcohols were oxidized by refluxing the reaction mixture for 1 h and conversions were monitored following the identical protocol. 80 %Chromat.
With periodic acid in water
T=45°C; 12 h;
Ganesamoorthy; Muthu Tamizh; Shanmugasundaram; Karvembu
Tetrahedron Letters, 2013 , vol. 54, # 51 p. 7035 - 7039 Title/Abstract Full Text View citing articles Show Details
With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 in aq. buffer T=30°C; pH=7.5; 24 h; Resolution of racemateEnzymatic reaction;
Paul, Caroline E.; Lavandera, Ivan; Gotor-Fernandez, Vicente; Kroutil, Wolfgang; Gotor, Vicente
ChemCatChem, 2013 , vol. 5, # 12 p. 3875 - 3881 Title/Abstract Full Text View citing articles Show Details
With tert.-butylhydroperoxide; oxygen in neat (no solvent) T=90°C; 24 h; Catalytic behavior;
Narkhede, Nilesh; Patel, Anjali; Singh, Sukriti
Dalton Transactions, 2014 , vol. 43, # 6 p. 2512 - 2520 Title/Abstract Full Text View citing articles Show Details
77 %Chromat.
With C49H43IrN2P2; potassium carbonate in acetone
Oppenauer Oxidation; 4 h; Reagent/catalyst; Hide Experimental Procedure
Paul, Piyali; Richmond, Michael G.; Bhattacharya, Samaresh
Journal of Organometallic Chemistry, 2014 , vol. 751, p. 760 - 768 Title/Abstract Full Text View citing articles Show Details
4.6 General procedure for Oppenauer oxidation
General procedure: In a typical run, an oven-dried round bottom flask was charged with a known mole percent of catalyst, K2CO3 (1.7mmol), primary or secondary alcohol (1.0mmol) in acetone medium (8mL). The mixture was stirred at 40°C. After the specified time the reaction mixture was extracted with ether (4×10mL). The combined organic layer was washed with water (3×10mL), and dried over anhydrous Na2SO4. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC–MS.
With tert.-butylhydroperoxide; Cs5[PCo(H2O)Mo11O39]*6H2O; oxygen
T=90°C; 24 h; Reagent/catalyst; chemoselective reaction;
Pathan, Soyeb; Patel, Anjali
Catalysis Science and Technology, 2014 , vol. 4, # 3 p. 648 - 656 Title/Abstract Full Text View citing articles Show Details
With tert.-butylhydroperoxide in neat (no solvent) T=89.84°C; P=760.051 Torr; 7 h; Green chemistry; Hide Experimental Procedure
Li, Kun; Zhou, Dan; Deng, Jiejie; Lu, Xinhuan; Xia, Qinghua
Journal of Molecular Catalysis A: Chemical, 2014 , vol. 387, p. 31 - 37 Title/Abstract Full Text View citing articles Show Details
Oxidation of other alcohols over Cr-13X
General procedure: The catalytic oxidation of cyclohexanol (Scheme 1) was carriedout in a 25-mL single-necked round-bottom glass flask equipped with a cryogenic-liquid condenser under atmospheric pressure. In a typical run, 40.0 mmol of cyclohexanol, 10.0 mmol of TBHP,and 100 mg of the catalyst were added to the reactor, and the mixture was stirred vigorously by a magnetic stirrer and heated in a preheated water bath. After the completion of the reaction, the liquid products were separated by centrifugation and analyzed by a gas chromatograph equipped with a capillary column (SE-30, 30 m × 0.25 mm × 0.25 m) and an FID detector, in which chlorobenzene was used as an internal standard to quantify all the components, and the solid catalyst was separated by filtration and washed thoroughly with acetone and ethanol, and dried at 373 K overnight for the next use. The cyclohexanol conversion, cyclo-hexanone selectivity, TBHP conversion and TBHP efficiency werecalculated by using Eqs. (1)-(4).
With C24H29ClRhSe2(1+)*F6P(1-); potassium carbonate; acetone in water
T=80°C; Oppenauer Oxidation; 5 h; Catalytic behavior; Reagent/catalyst;
Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham L.; Singh, Ajai K.
Organometallics, 2014 , vol. 33, # 4 p. 983 - 993 Title/Abstract Full Text View citing articles Show Details
With [Ru(CO)(1-methyl-2-{(o-thiomethyl)phenylazo}imidazole)I2]; 4-methylmorpholine Noxide in dichloromethane
T=40°C; Molecular sieveReflux; Reagent/catalyst;
Jana, Subrata; Jana, Mahendra Sekhar; Biswas, Sujan; Sinha, Chittaranjan; Mondal, Tapan Kumar
Journal of Molecular Structure, 2014 , vol. 1065-1066, # 1 p. 52 - 60 Title/Abstract Full Text View citing articles Show Details
83 %Chromat.
With dihydrogen peroxide in water
T=80°C; 12 h;
Shokouhimehr, Mohammadreza; Shin, Keun-Young; Lee, James S.; Hackett, Michael J.; Jun, Samuel Woojoo; Oh, Myoung Hwan; Jang, Jyongsik; Hyeon, Taeghwan
Journal of Materials Chemistry A, 2014 , vol. 2, # 20 p. 7593 - 7599 Title/Abstract Full Text View citing articles Show Details
in toluene
T=110°C; 18 h; Catalytic behavior;
Ganesh Babu; Krishnamoorthi; Thiruneelakandan; Karvembu
Catalysis Letters, 2014 , vol. 144, # 7 p. 1245 - 1252 Title/Abstract Full Text View citing articles Show Details
Stage #1: in dichloromethane
0.00833333 h; SonicationMicellar solution; Stage #2: With sodium hypochlorite; sodium bromide in dichloromethane
T=10°C; pH=Ca. 9.1; 0.1 h; Micellar solution;
Zheng, Zhi; Wang, Jianli; Chen, Hualiang; Feng, Linbin; Jing, Ren; Lu, Meizhen; Hu, Bao; Ji, Jianbing
ChemCatChem, 2014 , vol. 6, # 6 p. 1626 - 1634 Title/Abstract Full Text View citing articles Show Details
70 %Chromat.
With air; multiwall carbon nanotube supported on r-ruthenium dioxide nanoparticle in toluene
T=110°C; 20 h; Hide Experimental Procedure
Gopiraman; Babu, S. Ganesh; Karvembu; Kim
Applied Catalysis A: General, 2014 , vol. 484, p. 84 - 96 Title/Abstract Full Text View citing articles Show Details
2.4. Aerial oxidation of alcohols
General procedure: Five milligram of r-RuO2/MWCNT (0.68 molpercent) was stirred with3 mL of toluene taken in a round-bottomed flask equipped with a condenser and a magnetic stirrer. The substrate (1 mmol) was added to the stirring solution and then the mixture was refluxed at 110°C under atmospheric pressure of air. The completion of the reaction was checked by GC. After the reaction, the r-RuO2/MWCNTwas separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was also calculated.
With 2O39PW11(7-)*11K(1+)*Pr(3+)*22H2O; dihydrogen peroxide in water
T=90°C; 3 h; Green chemistry;
Saini, Mukesh Kumar; Gupta, Rakesh; Parbhakar, Swati; Singh, Surendra; Hussain, Firasat
RSC Advances, 2014 , vol. 4, # 72 p. 38446 - 38449 Title/Abstract Full Text View citing articles Show Details
93 %Chromat.
With Co0.44Pd0.56; oxygen; potassium carbonate in ethanol; water
T=60°C; P=760.051 Torr; Hide Experimental Procedure
Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro
Tetrahedron, 2014 , # 36 p. 6146 - 6149 Title/Abstract Full Text Show Details
4.3. General procedure for catalytic aerobic oxidation of primaryalcohols in water
General procedure: A mixture of magnetic nanoparticles 1a-e (suspension in ethanol; 0.16 M CoePd), primary alcohol (0.2 mmol), and potassium carbonate (0.2 mmol) in water (2 mL) was stirred at 60 C under oxygen gas at atmospheric pressure. After being cooled, the mixture was washed with ether, and acidified with 5percent hydrochloric acid. The mixture was extracted with ethyl acetate (51 mL). The extract was dried over magnesium sulfate. The resulting solution was analyzed by GC and GC-MS (with Mass Spectral Reference Database). The yield of the product was determined by GC with aninternal standard (o-xylene). > 99 %Chromat.
With dihydrogen peroxide in water; acetonitrile
T=90°C; 19 h; Green chemistry; Hide Experimental Procedure
Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah
Tetrahedron, 2014 , # 36 p. 6114 - 6119 Title/Abstract Full Text Show Details
General procedure for oxidation of alcohols to the correspondingcarbonyl compound with 30percent H2O2
General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5 mmol) were added to an equal mixture of water and acetonitrile (1.5 ml). Then, WO4PMO-IL (0.23 g, ~1.5 mol percent) was added to the above solution and the resulting mixture was stirred at 90 °C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (310 ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. 77 %Chromat.
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate in water; acetic acid; toluene
T=100°C; 24 h;
Gunay, Ahmet; Mantell, Mark A.; Field, Kathleen D.; Wu, Wenbo; Chin, Michael; Emmert, Marion H.
Catalysis Science and Technology, 2015 , vol. 5, # 2 p. 1198 - 1205 Title/Abstract Full Text View citing articles Show Details
With oxygen in toluene
T=60°C; P=760.051 Torr; 20 h; Catalytic behavior;
Zhang, Pengfei; Qiao, Zhen-An; Jiang, Xueguang; Veith, Gabriel M.; Dai, Sheng
Nano Letters, 2015 , vol. 15, # 2 p. 823 - 828 Title/Abstract Full Text View citing articles Show Details
>99 %Chromat.
With dihydrogen peroxide in water; acetonitrile
T=90°C; 19 h; Green chemistry; chemoselective reaction; Hide Experimental Procedure
Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah
Tetrahedron, 2014 , vol. 70, # 36 p. 6114 - 6119 Title/Abstract Full Text View citing articles Show Details
4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent H2O2
General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4=PMO-IL (0.23g, ∼1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. 100 %Chromat.
With dihydrogen peroxide in water
T=45°C; 2.16667 h; Green chemistry;
Nikbakht, Elham; Yadollahi, Bahram; Farsani, Mostafa Riahi
Inorganic Chemistry Communications, 2015 , vol. 55, p. 135 - 138 Title/Abstract Full Text View citing articles Show Details
93 %Chromat.
With oxygen in water
T=60°C; P=760.051 Torr; 24 h; Hide Experimental Procedure
Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro
Tetrahedron, 2014 , vol. 70, # 36 p. 6146 - 6149 Title/Abstract Full Text View citing articles Show Details
4.4. General procedure for catalytic aerobic oxidation of secondary alcohols in water
General procedure: A mixture of magnetic nanoparticles 1a (suspension in ethanol) and secondary alcohol (0.2 mmol) in water (2 mL) was stirred at 60°C under oxygen gas at atmospheric pressure. After it was cooled, the mixture was extracted with ethyl acetate (51 mL). The extract was analyzed by GC and GC-MS (with Mass Spectral Reference Database). The yield of the product was determined by GC with an internal standard (o-xylene or mesitylene).
With tert.-butylhydroperoxide; oxygen in water
T=90°C; 24 h; Catalytic behavior;
Singh, Sukriti; Narkhede, Nilesh; Patel, Anjali
RSC Advances, 2015 , vol. 5, # 46 p. 36270 - 36278 Title/Abstract Full Text View citing articles Show Details
81 %Chromat.
With potassium carbonate in water
T=80°C; 5 h;
Rostamnia, Sadegh; Doustkhah, Esmail; Karimi, Ziba; Amini, Soraya; Luque, Rafael
ChemCatChem, 2015 , vol. 7, # 11 p. 1678 - 1683 Title/Abstract Full Text View citing articles Show Details
With methoxybenzene in toluene
T=100°C; 24 h;
Poreddy, Raju; Engelbrekt, Christian; Riisager, Anders
Catalysis Science and Technology, 2015 , vol. 5, # 4 p. 2467 - 2477 Title/Abstract Full Text View citing articles Show Details
80 %Chromat.
With 10Na(1+)*4Co(2+)*2O34PW9(9-); dihydrogen peroxide in water
4 h; RefluxGreen chemistry; Hide Experimental Procedure
Farsani, Mostafa Riahi; Assady, Elham; Jalilian, Fariba; Yadollahi, Bahram; Rudbari, Hadi Amiri
Journal of the Iranian Chemical Society, 2015 , vol. 12, # 7 art. no. 583, p. 1207 - 1212 Title/Abstract Full Text View citing articles Show Details
Typical procedure for catalytic oxidation of alcohols
General procedure: The catalytic reactions were carried out in a 10-mL roundbottomflask equipped with a magnetic stirring bar and areflux condenser. The Co-STPOM catalyst (0.001 mmol),water (3 mL), alcohol (1 mmol), and H2O2 (9.8 mmol)were charged in the reaction vessel. The reaction was carriedout at reflux and progress of the reaction was detectedby TLC and GC. After completion of the reaction, organicproduct was isolated by ethyl acetate (3 × 2 mL) and theorganic layer was analyzed by gas chromatography or 1HNMR. Products were assigned by comparing experimentaldata with authentic samples. 99 %Chromat.
With sodium periodate; C14H30Cl2FeN4(1+)*F6P(1-) in water
T=23°C; 22 h;
Tan, Peng; Kwong, Hoi-Ki; Lau, Tai-Chu
Chemical Communications, 2015 , vol. 51, # 61 p. 12189 - 12192 Title/Abstract Full Text View citing articles Show Details
in N,N-dimethyl-formamide
T=120°C; 10 h; Inert atmosphere;
Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming
Applied Organometallic Chemistry, 2015 , vol. 29, # 3 p. 152 - 156 Title/Abstract Full Text View citing articles Show Details
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct in acetonitrile
T=70°C; 12 h;
Amanchi, Srinivasa Rao; Khenkin, Alexander M.; Diskin-Posner, Yael; Neumann, Ronny
ACS Catalysis, 2015 , vol. 5, # 6 p. 3336 - 3341 Title/Abstract Full Text View citing articles Show Details
With styrene; 1,3,5-trimethyl-benzene
T=130°C; 24 h; Inert atmosphere;
Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Chen, Chen; Xu, Jie
Chinese Journal of Catalysis, 2014 , vol. 35, # 12 p. 1911 - 1916 Title/Abstract Full Text Show Details
With C31H27Cl2N2PRhS(1+)*F6P(1-); potassium carbonate; 4-methylmorpholine N-oxide in dichloromethane
3 h; Molecular sieveReflux; Hide Experimental Procedure
Biswas, Sujan; Sarkar, Deblina; Kundu, Subhankar; Roy, Puspendu; Mondal, Tapan Kumar
Journal of Molecular Structure, 2015 , vol. 1099, p. 297 - 303 Title/Abstract Full Text View citing articles Show Details
2.5. Procedure for catalytic oxidation of alcohols with NMO
General procedure: A solution of complex (0.01 mmol) in CH2Cl2 (25 mL) was addedto the mixture containing alcohol substrate (1 mmol), K2CO3(1.3 mmol), solid NMO (3 mmol) and molecular sieves. The reactionmixture was refluxed for 3 h, and the solvent was then evaporatedunder reduced pressure. The residue was then extracted withdiethyl ether (20 mL), concentrated to z 1 mL. The oxidizedproduct present in diethyl ether extract was analyzed by GC. 12 %Chromat.
With dihydrogen peroxide in water
T=27°C; 24 h; Hide Experimental Procedure
Emayavaramban; Ganesh Babu; Karvembu; Kadirvelu; Dharmaraj
Journal of Nanoscience and Nanotechnology, 2016 , vol. 16, # 3 p. 2517 - 2526 Title/Abstract Full Text View citing articles Show Details
2.4. Procedure for Alcohol Oxidation
General procedure: A typical reaction scheme for the alcohol oxidation isgiven in Scheme 1. Au–MgO nanorods (30 mg) and H2O2(945 L, 15 equivalence) were stirred in 20 mL of waterand the substrate alcohol (1 mM) was slowly added to thereaction mixture and continuously stirred at room temperature.After the requisite time, the catalyst was separatedby centrifugation. The centrifugate was extracted usingdiethyl ether. The ether extract was dried over anhydroussodium sulphate and evaporated. Then the product was dissolvedin ethyl acetate and then analysed by GC. Authenticsamples of reactants and respective products were used toverify the retention time and to confirm the product formation.The used catalyst was washed with ethyl acetate and dried under vacuum. The dried catalyst was calcinedat 500 C before reuse.
With air; hydrogen reduced 10 wtpercent alumina supported silver in para-xylene
T=120°C; 3 h;
Liu, Huihui; Tan, Hui-Ru; Tok, Eng Soon; Jaenicke, Stephan; Chuah, Gaik-Khuan
ChemCatChem, 2016 , vol. 8, # 5 p. 968 - 975 Title/Abstract Full Text View citing articles Show Details
With dihydrogen peroxide in water
T=90°C; 6 h; Hide Experimental Procedure
Wang, Hefang; Fang, Luping; Yang, Yongfang; Hu, Rongbin; Wang, Yanji
Applied Catalysis A: General, 2016 , vol. 520, p. 35 - 43 Title/Abstract Full Text View citing articles Show Details
2.3. General procedure of catalytic oxidation reaction
General procedure: Oxidation of alcohol was carried out in a 100 mL three-neckedflask equipped with a reflux condenser, a magnetic stirrer anda thermometer. typically, the reactor was loaded with alcohol(5 mmol), H2O (10 mL) and catalyst. then, 30percent aqueous hydro-gen peroxide (10 mmol) was added dropwise to the reactorunder the setting temperature under vigorous stirring for 300 min.after the finish of reaction, the products were extracted withdichloromethane from aqueous phase and were identified by aSP-3420A GC equipped with a KB-Wax column (30 m, 0.32 mm id,0.25 m film thickness) with toluene as internal standardAlcoholconversion(percent)=[(molesofalcoholadded−molesofunconvertedalcohol)/molealcoholadded]×100Productselectivity(percent)=[molesoftheproduct/(molesofalcoholadded−molesofunconvertedalcohol)]×100TOF : mmolketone/(mmolheteropolyanionincatalyst×reactiontime).
With tert.-butylhydroperoxide; [Fe(2,2'-bipyridine)3](OTf)2
T=25°C; 24 h; Green chemistry; Hide Experimental Procedure
Chàvez, Jennifer E.; Crotti, Corrado; Zangrando, Ennio; Farnetti, Erica
Journal of Molecular Catalysis A: Chemical, 2016 , vol. 421, p. 189 - 195 Title/Abstract Full Text View citing articles Show Details
Oxidation of alcohols catalyzed by [Fe(N-N)3](OTf)2In
General procedure: In a round-bottomed flask the solvent (3.0 mL) and the cat-alyst precursor [Fe(N-N)3](OTf)2(0.050 mmol) were introduced, followed by the substrate (2.5 mmol). For reactions performed at temperatures higher than r.t., the resulting solution was heated ina thermostatted bath to the desired temperature. Slow addition of the oxidant was then carried out under stirring. After the desired time the reaction mixture was cooled at −18 °C and subsequently analized by GC and/or NMR. 70.5 %Chromat.
With 1H-imidazole; tert.-butylhydroperoxide; N -hydroxyphthalimide; [Fe(bpc)Cl2][Et4N] in acetonitrile
T=50°C; 7 h; Reagent/catalyst; Hide Experimental Procedure
Bae, Jeong Mi; Lee, Myoung Mi; Lee, Seul Ah; Lee, Sun Young; Bok, Kwon Hee; Kim, Jinheung; Kim, Cheal
Inorganica Chimica Acta, 2016 , vol. 451, p. 8 - 15 Title/Abstract Full Text View citing articles Show Details
catalytic alcohol oxidations by t-BuOOH in the presence of iron complexes
General procedure: t-BuOOH (0.075 mmol) was added to a mixture of substrate(0.05 mmol), iron complex (1.0 103 mmol), imidazole (0.01 mmol), NHPI (0.02 mmol), and solvent (CH3CN; 1 mL). The mixture was stirred for the given time at 50 °C. Each reaction was monitored by GC/MS analysis of 20 lL aliquots withdrawn periodically from the reaction mixture. Dodecane was used as an internal standard to quantify the yields of products and conversions of substrates. All reactions were run at least in triplicate, and the average conversions and product yields have been presented. Conversions and product yields were calculated with respect to substrates. 47 %Spectr.
With oxone in [(2)H6]acetone
15 h; Inert atmosphere; Hide Experimental Procedure
Yale University; Bloomfield, Aaron J.; Sheehan, Stafford W.; Collom, Samuel L.; Crabtree, Robert H.; Anastas, Paul T.
Patent: US2016/152648 A1, 2016 ; Location in patent: Paragraph 0209 ; Title/Abstract Full Text Show Details
7:
A stock solution of KHSO5 was prepared in degassed D20 under N2. Catalyst (e.g., Co-dppe) was added to each reaction tube. The tubes were then evacuated under vacuum and refilled with N2 several times. 400 jtL of d5-ac- etone was added to each tube followed by the appropriate substrate. Reactions were initiated by the addition of 100 pL of KHSO5 stock solution. Reactions were monitored for 3 or 15 hrs depending on the substrate. The reactions were quenched by addition of a stock solution of d4-sodium trimethylsilyl propionate (NMR internal standard) and d5-dim- ethylsulfoxide (oxidant quench). The reactions stirred another 15 mm and then were filtered into NMR tubes. The reactions were quantified by NMR. (Control reactions were performed without catalyst and in each case the substrate conversion is >5percent)10209] For most of the substrates selective oxidation to a single product was observed. The catalyst system was able to oxidize unactivated alkanes to a single product but in low yield. Oxidation of 1 -butanol illustrates the difference the catalyst and simple cobalt salts. The catalyst selectively oxidizes butanol to butyric acid whereas the CoOl) salts tested were highly unselective, affording several different products.
With oxygen in hexane
T=19.84°C; P=760.051 Torr; 6 h; Green chemistry;
Lee, Deok Rok; Kim, Jeong Won
Patent: KR2016/9439 A, 2016 ; Location in patent: Paragraph 0021; 0022 ; Title/Abstract Full Text Show Details
Stage #1: With nickel(II) chloride hexahydrate; cadmium sulphide in acetonitrile
0.00277778 h; Schlenk techniqueSonicationInert atmosphere; Stage #2: in acetonitrile
T=20°C; 20 h; IrradiationInert atmosphereSchlenk technique;
Chai, Zhigang; Zeng, Ting-Ting; Li, Qi; Lu, Liang-Qiu; Xiao, Wen-Jing; Xu, Dongsheng
Journal of the American Chemical Society, 2016 , vol. 138, # 32 p. 10128 - 10131 Title/Abstract Full Text View citing articles Show Details
95 %Chromat.
With C29H35Cl2IrN2O2; sodium acetate in 2,2,2-trifluoroethanol
20 h; Inert atmosphereRefluxSchlenk technique;
Gülcemal, Süleyman; Gülcemal, Derya; Whitehead, George F. S.; Xiao, Jianliang
Chemistry - A European Journal, 2016 , vol. 22, # 30 p. 10513 - 10522 Title/Abstract Full Text View citing articles Show Details
78 %Chromat.
With tert.-butylhydroperoxide; C9H11CuN7O7S*H2O in water
T=80°C; 0.25 h; Microwave irradiation; Catalytic behavior; Reagent/catalyst;
Frija, Luís M.T.; Alegria, Elisabete C.B.A.; Sutradhar, Manas; Cristiano, M. Lurdes S.; Ismael, Amin; Kopylovich, Maximilian N.; Pombeiro, Armando J.L.
Journal of Molecular Catalysis A: Chemical, 2016 , vol. 425, p. 283 - 290 Title/Abstract Full Text View citing articles Show Details
99 %Chromat.
With potassium carbonate in water
T=80°C; Catalytic behavior;
Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan
RSC Advances, 2016 , vol. 6, # 108 p. 106769 - 106777 Title/Abstract Full Text View citing articles Show Details
With 1-methyl-2-azaadamantane-N-oxyl; oxovanadium(IV) sulfate; oxygen in acetonitrile
T=80°C; P=3750.38 Torr; 3 h; Hide Experimental Procedure
Dalian University of Technology; Du, zhongtian; Tang, yangyang; Sun, xiaowan
Patent: CN105541526 A, 2016 ; Location in patent: Paragraph 0027; 0028 ; Title/Abstract Full Text Show Details
8:Embodiment 8
The 0.86g Cyclopentaol, 2mol percent (relative to the Cyclopentaol) aza jin'gang alkane nitroxyl radical (II), 2mol percent (relative to the Cyclopentaol) vanadyl sulfate, 5 ml acetonitrile is added to the reactor, filled with oxygen pressure is 0.5 MPa, in the 80 °C running 3h after cooling to room temperature. Sampling by the use of gas chromatography analysis, Cyclopentaol conversion 99.8percent, dumasin selectivity of 97.4percent.
With Ni-Cu/Al 2O3-SiO 2
T=135°C; P=150.015 Torr; Flow reactor; TemperaturePressure; Hide Experimental Procedure
Shanghai Pearlk Chemicals Co., Ltd; Shi, Kangming
Patent: CN105461526 A, 2016 ; Location in patent: Paragraph 0015-0018 ; Title/Abstract Full Text Show Details
7:
General procedure: The dehydrogenation reactor is a stainless steel tubular reactor of size Φ25ππΧ 1000mm. The reaction tube is filled with 100ml catalyst. The catalyst is composed of Ni and Cu as the active components, A mixture of Al230 and Si02 is a carrier having a Ni content of 30 to 50 wtpercent, a Cu content of 1 to 5 wtpercent The The bottom of the reactor is filled with inert porcelain balls. The dehydrogenated feedstock is preheated and passed through the distributor at a rate set at the top through the distributor into the reactor for dehydrogenation. The dehydrogenation material enters the gas stream from the bottom of the dehydrogenation reactor Separator, liquid phase material into the product tank. The system pressure is controlled by the gas regulator valve separated by the gas-liquid separator. The specific reaction conditions, the dehydrogenation reaction of cyclopentanol conversion and cyclopentanone selectivity are shown in Table 1.
100 %Chromat.
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane
20 h; RefluxInert atmosphere; SolventTemperature; Hide Experimental Procedure
Kanto Kagaku Kabushiki Kaisha; Yamaguchi, Ryohei; Fujita, Ken-ichi
Patent: US2016/297844 A1, 2016 ; Location in patent: Paragraph 0143; 0154 ; Title/Abstract Full Text Show Details
12:Synthesis of ketone by dehydrogenative oxidation reaction of secondary alcohol
Dehydrogenative oxidation reactions of various secondary alcohols were carried out using complex 1 as a catalyst under the reaction conditions shown in Table 3. After the reactions were completed, when the reaction solutions were analyzed by GC it was confirmed that ketones were formed with a high conversion factor and a high yield in all cases.
3
With nickel dichloride in water
T=20°C; pH=9; 24 h; Inert atmosphereIrradiation;
Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing; Ye, Chen; Li, Xu-Bing; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu
Angewandte Chemie - International Edition, 2017 , vol. 56, # 11 p. 3020 - 3024 Angew. Chem., 2017 , vol. 129, # 11 p. 3066 - 3070,5 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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A: 5% B: 8% C: 21% D: 36%
With hydrogen in water
T=150°C; P=15001.5 Torr; 4 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure
Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao
Chinese Chemical Letters, 2017 , vol. 28, # 6 p. 1153 - 1158 Title/Abstract Full Text View citing articles Show Details
Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products.
A: 16.49% B: 12.12% C: 16.42% D: 7.63%
With hydrogen in water
T=175°C; P=60006 Torr; 0.5 h;
Hronec, Milan; Fulajtarova, Katarina
Catalysis Communications, 2012 , vol. 24, p. 100 - 104 Title/Abstract Full Text View citing articles Show Details
A
4
B
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A: 68% B: 14%
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With hydrogen in water
T=160°C; P=15001.5 Torr; 4 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure
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Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao
Chinese Chemical Letters, 2017 , vol. 28, # 6 p. 1153 - 1158 Title/Abstract Full Text View citing articles Show Details
Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products.
A: 7.91% B: 55.74%
With 5 platinum on carbon; hydrogen in water
T=160°C; P=60006 Torr; 2.5 h;
Hronec, Milan; Fulajtarova, Katarina
Catalysis Communications, 2012 , vol. 24, p. 100 - 104 Title/Abstract Full Text View citing articles Show Details
With water; hydrogen
T=160°C; P=30003 Torr; 4 h; Autoclave; Overall yield = 65 percent;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Hide Details
5
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 4 h / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water; pentanal / 4 h / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: water / 4 h / 160 °C / 750.08 Torr / |Inert atmosphere; |Autoclave 2: hydrogen; water / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 8 h / 160 °C / |Inert atmosphere; |Autoclave 3: hydrogen; water / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With 30 Cu/Co3O4; hydrogen in water
T=149.84°C; P=30003 Torr; 6 h; Autoclave; Reagent/catalyst; chemoselective reaction;
Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao
Green Chemistry, 2015 , vol. 17, # 2 p. 1038 - 1046 Title/Abstract Full Text View citing articles Show Details
With hydrogen; cobalt in water
T=169.84°C; P=15001.5 Torr; 1 h; Autoclave; Reagent/catalyst; chemoselective reaction;
Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao
Green Chemistry, 2015 , vol. 17, # 2 p. 1038 - 1046 Title/Abstract Full Text View citing articles Show Details
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98%
With hydrogen in water
T=160°C; P=30003 Torr; 7 h; Automated synthesizer;
Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong
Green Chemistry, 2016 , vol. 18, # 7 p. 2155 - 2164 Title/Abstract Full Text View citing articles Show Details
96%
With hydrogen in water
T=160°C; P=30003 Torr; 2.5 h; Autoclave; Reagent/catalystTemperaturePressure;
Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei
Green Chemistry, 2015 , vol. 17, # 8 p. 4183 - 4188 Title/Abstract Full Text View citing articles Show Details
76.5%
With 5 platinum on carbon; hydrogen in water
T=160°C; P=60006 Torr; 0.5 h; chemoselective reaction;
Hronec, Milan; Fulajtarova, Katarina
Catalysis Communications, 2012 , vol. 24, p. 100 - 104 Title/Abstract Full Text View citing articles Show Details
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6
With water; hydrogen
T=160°C; P=15001.5 Torr; 4 h; Autoclave; Reagent/catalyst;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With hydrogen; 18O-labeled water
T=160°C; 4 h;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: 5-hydroxymethyl-2-furfuraldehyde; hydrogen; water / 4 h / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With hydrogen in water
T=150°C; P=10501.1 - 30003 Torr; 6 h; Reagent/catalyst;
Bui, Tuong V.; Sooknoi, Tawan; Resasco, Daniel E.
ChemSusChem, 2017 , vol. 10, # 7 p. 1631 - 1639 Title/Abstract Full Text View citing articles Show Details
Rx-ID: 40786159 Find similar reactions
B
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A
B: 73%
With hydrogen in water
T=160°C; P=30003 Torr; 2.5 h; Autoclave; Reagent/catalyst;
Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei
Green Chemistry, 2015 , vol. 17, # 8 p. 4183 - 4188 Title/Abstract Full Text View citing articles Show Details
A: 14% B: 56%
With hydrogen in water
T=160°C; P=15001.5 Torr; 1 h; Autoclave; Hide Experimental Procedure
Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao
Chinese Chemical Letters, 2017 , vol. 28, # 6 p. 1153 - 1158 Title/Abstract Full Text View citing articles Show Details
Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products.
B: 29%
With Ru/C; hydrogen in water
T=160°C; P=30003 Torr; 2.5 h; Autoclave; Reagent/catalyst;
Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei
Green Chemistry, 2015 , vol. 17, # 8 p. 4183 - 4188 Title/Abstract Full Text View citing articles Show Details
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With hydrogen
T=160°C; P=67506.8 Torr; 1.5 h; Hide Experimental Procedure
Nippon Shokubai Co., Ltd.; Kirishiki, Ken; Maeda, Ryohei
Patent: JP2016/108282 A, 2016 ; Location in patent: Paragraph 0041; 0043; 0044 ; Title/Abstract Full Text Show Details
2:
An irrigation packed bed reactor made of SUS 316 having an outer diameter of 10 mmφ, an inner diameter of 8 mmφ, and a length of 400 mm Was charged with 0.5 g of the catalyst obtained above and the upper and lower sides of the catalyst were fixed with quartz wool. On the reactor , A 1 wtpercent furfural aqueous solution was fed at a rate of 0.20 g / min and hydrogen was supplied at a rate of 50 m L / min. At that time, the catalyst part temperature of the reactor was 160 ° C., the reaction pressure was 0. It was 9 MPa. Table 1 shows the furfural conversion rate and the yield of the main products at 1.5 hours after the start of the reaction. The conversion of furfural and the yield of each product are values calculated by the following formula is there The same as in Example 1 except that in Example 1, the catalyst charged in the reactor was changed to 1.0 g .
7
A
B
C
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A: 75.3 %Chromat. B: 11.6 %Chromat. C: 13.1 %Chromat.
Stage #1: With C19H42N(1+)*2H(1+)*O40PW12(3-); water; dihydrogen peroxide
T=80°C; 6 h; Stage #2: With hydroxyammonium sulfate
T=100°C; Beckmann Rearrangement; 5 h; Catalytic behavior; Overall yield = 82.8 percentChromat.; chemoselective reaction; Hide Experimental Procedure
Wang, Hefang; Hu, Rongbin; Yang, Yongfang; Gao, Meidan; Wang, Yanji
Catalysis Communications, 2015 , vol. 70, p. 6 - 11 Title/Abstract Full Text View citing articles Show Details
2.5. Catalytic test.
General procedure: In a typical experiment, the catalyst (0.25 mmol) was mixed with cyclohexanol (50 mmol) in a 100 mL three-necked flask equipped with a reflux condenser, a magnetic stirrer and a thermometer. When the required temperature reached, 30percent aqueous hydrogen peroxide (75 mmol) was then added dropwise to the reaction mixture, with vigorous stirring for 300 min. Hydroxylamine sulfate (25 mmol) was added to the flask with vigorous stirring for a certain time. After the completionof reaction, the reaction mixture was divided into two phases. Water phase was extracted with dichloromethane and the product swere identified by a Thermo Trace DSQ gas chromatograph–mass spectrometer. The products were analyzed by a SP-3420A gas chromatograph equipped with a KB-Wax column (30 m, 0.32 mm id, 0.25 μm film thickness) with toluene as internal standard.
Stage #1: With [TMBSA][HSO4]; 6Na(1+)*O4W(2-)*2H2O; dihydrogen peroxide
T=80°C; Green chemistry; Stage #2: With hydroxyammonium sulfate
T=80°C; 5 h; Green chemistry; Hide Experimental Procedure
Wang, Hefang; Jia, Liyuan; Hu, Rongbin; Gao, Meidan; Wang, Yanji
Chinese Journal of Catalysis, 2017 , vol. 38, # 1 p. 58 - 64 Title/Abstract Full Text Show Details
2.2. Catalytic testing
General procedure: In a typical procedure, Na2WO4 (2.75 mmol) and an ionicliquid were mixed with cyclohexanol (50 mmol) in a 100 mLthree necked flask equipped with a reflux condenser, magneticstirrer and a thermometer. The resulting mixture was thenheated to the required temperature, and treated with 30percentH2O2 (75 mmol), which was added in a dropwise manner to thereaction mixture with vigorous stirring over 5 h. Hydroxylaminesulfate (25 mmol) was then added to the flask with vigorousstirring over a certain period of time. Upon completion ofthe reaction, the mixture was allowed to settle to give twophases. The aqueous phase was collected and extracted withdichloromethane, and the extracted products were identifiedby gas chromatography mass spectrometry using a ThermoTrace DSQ gas chromatograph mass spectrometer (ThermoElectron, Massachusetts, America). The products were analyzedon an SP 3420A gas chromatograph equipped with a KB Waxcolumn (30 m × 0.32 mm × 0.25 μm). A
8
B
C
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With methane; platinum on carbon
T=300°C; P=760.051 Torr; Catalytic behavior; Reagent/catalystTemperature; Hide Experimental Procedure
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PURDUE RESEARCH FOUNDATION; Varma, Arvind; Xiao, Yang
Patent: US2017/29712 A1, 2017 ; Location in patent: Paragraph 0012-0025 ; Title/Abstract Full Text Show Details
For the purposes of promoting an understanding of the principles of the present disclosure, reference will now be made to the embodiments illustrated in the drawings, and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of this disclosure is thereby intended. (0013) Hydrodeoxygenation (HDO) is a promising strategy to overcome problems associated with biomass to biofuel conversion. Since bio-oil is a complex mixture, of generally more than 400 chemical species, a model compound is typically used to obtain insight into the HDO process. Guaiacol is one such representative compound owing to its two common oxygenated groups: hydroxyl and methoxyl. Extensive research has been conducted in this field. It should therefore be appreciated that while guaiacol is the model compound used to demonstrate the methods disclosed herein, such use is not intended to be limiting and rather, other biomass compounds can be used. In general, Group VIII metals (Pt, Pd, Ni, Rh, Ru, and so on) are used to activate guaiacol and to facilitate hydrogen donation, while Al2O3, ZrO2, SiO2 and activated carbon are considered to be effective supports. (0014) Although the use of hydrogen for deoxygenation of guaiacol is advantageous because it generates clean products (mainly water), it often carries high economic penalties arising from its production and transportation. In this context, methane, as the main component in natural gas (CH4>95percent) and major component of shale gas (typically CH4>70percent), is attractive as an alternative to H2 since it can serve as a hydrogen donor by releasing hydrogen at high temperature on noble metal surfaces, which makes it a potential promising reductant. (0015) To facilitate understanding of the methods disclosed herein, with Pt/C as catalyst, a guaiacol deoxygenation process using H2 is presented herein. Based on kinetics and catalyst characterization, deactivation mechanism and reaction pathways are also proposed. To overcome the high cost of H2, methane is used in the present disclosure to deoxygenate guaiacol. (0016) Results and Discussion: (0017) In preliminary work with Pt/C catalyst, the use of CH4 was shown to be successful for guaiacol deoxygenation, but significant catalyst deactivation was observed. This observation is similar to other works for CH4 reactions and is related to coking/carbon deposition. The deactivation issue has been addressed for other reactions by use of bimetallic catalysts, containing a primary metal and a promoter. Thus, in the present disclosure, a guaiacol deoxygenation process using methane is developed via Pt—Bi catalyst. (0018) Four cases (PtH2, PtCH4, PtBiH2 and PtBiCH4), derived from two catalysts (Pt/C, Pt—Bi/C) using either H2 or CH4 as reductant, were tested for deoxygenation of guaiacol under standard operating conditions: 300° C., 1 atm, 0.50 g catalyst, total gas (reductant gas, H2 or CH4:N2=1:1) flow rate 100 mL/min, and guaiacol feed rate 0.025 mL/min (liquid, at room temperature), corresponding to contact time 0.3 g catalyst·hr/g guaiacol. A Van Krevelen diagram (FIG. 1a) is used to evaluate the deoxygenation levels by analyzing O/C and H/C molar ratios in the liquid products, which compares hydrogenation vs. deoxygenation performance. Owing to catalyst deactivation, data taken at 60 min time on stream (TOS) is reported in FIG. 1a. It shows that guaiacol has H/C of 1.14 and O/C of 0.28, implying a high O content. The H/C ratios increase to 1.18-1.20 and O/C ratios decrease to 0.21-0.22 for all the four cases after deoxygenation, indicating that both hydrogenation and deoxygenation occur. It clearly shows that all four cases behave similarly in the early stages of TOS, although the initial conversions of guaiacol vary from 79percent-90percent (FIG. 1b). The high yield and good stability of PtH2 case have been reported. Since CH4 decomposes on Pt surface donating hydrogen, the PtCH4 case has a high initial guaiacol conversion. In fact, H2 is detected in the gaseous products. As shown in FIG. 1b, with increasing TOS, however, the PtCH4 case exhibits sharp deactivation, while the other three cases maintain good stability. As noted above, a possible reason for rapid deactivation in the PtCH4 case is carbon deposit and/or coking, resulting from CH4 decomposition. (0019) In the PtBiH2 case of FIG. 1b, good stability is obtained although the conversion is decreased by 10percent, as compared to the PtH2 case. Remarkably, PtBiCH4 also shows good catalyst stability, although the conversion is decreased further. For a C8 hydrocarbon reforming process using catalyst containing a Group VIII metal and low amounts of bismuth, a patent disclosed that addition of bismuth extended catalyst lifetime. In fact, this is the only prior work demonstrating catalyst stability using Bi as a promotor for gas-phase reactions at high temperature (>300° C.). Although the mechanism is unclear, our experiments also show that Bi promotor extends catalyst lifetime. It should also be noted that in a patent application, Fernando et al. describe the use of methane with an oxygenate to dehydrate and produce deoxygenated hydrocarbons, but no bimetallic catalysts or data for catalyst stability were reported. (0020) FIGS. 2a-2d show distribution of major components in both gaseous and liquid products at 60 min TOS under standard conditions (FIG. 2a corresponds to PtH2, FIG. 2b corresponds to PtCH4, FIG. 2c corresponds to PtBiH2, and FIG. 2d corresponds to PtBiCH4). Note that components less than 2 wt percent are neglected and all compositions are normalized with respect to the remaining components. Only three main products (phenol, catechol and cyclopentanone, total content >95 wt percent for all four cases) in the liquid are shown. For liquid products, all four cases have similar distributions and compositions. For gaseous products, the PtH2 and PtBiH2 cases generated CO and CH4, while PtCH4 and PtBiCH4 produced CO and C2H6 instead. Since our work using Pt and H2 suggested that CO and CH4 are generated along with cyclopentanone, we can conclude that C2H6 is generated by the use of CH4. Thus, a conceptual scheme is presented for comparison of H2 and CH4 deoxygenation processes. <in-line-formulae>For hydrogen deoxygenation: R2O+2H2→2RH+H2O</in-line-formulae> <in-line-formulae>For methane deoxygenation: R2O+4CH4→2RH+2C2H6+H2O</in-line-formulae> (0021) It is disclosed that CH4 decomposes on Pt surface and contributes one H atom for guaiacol deoxygenation and water formation, similar to the H2 process, while the residual methyl combines with another methyl to form ethane. This assumption is supported by the low reaction barrier of CH4 decomposition at elevated temperature, along with detected H2 and C2H6 molecules in our experiments. (0022) To further understand Pt—Bi performance for guaiacol deoxygenation using CH4 as reductant, different temperatures (300-450° C.) were investigated for guaiacol conversion and carbon recovery in liquid and gaseous products, as shown in FIGS. 3a-3b. FIG. 3a shows increase of guaiacol conversion with temperature, where conversions >90percent are reached for 400-450° C. Remarkably, as shown in FIGS. 1a and 1b, such conversion is obtained at 300° C. when Pt and H2 are used. Therefore, reaction rate is decreased by either using CH4 as reductant or Pt—Bi as catalyst. Besides guaiacol conversion, carbon recovery in the liquid phase is another important factor to assess the catalyst performance, as shown in FIG. 3b. Two major factors are considered to affect carbon recovery in the liquid phase: guaiacol conversion (to the three main liquid products) and other reactions that decompose guaiacol to produce gaseous products, which occur on carbon-supported noble metal catalysts. Along with temperature increase, carbon recovery in liquid product first increased and then decreased after 400° C., while carbon recovery in gaseous products shows the opposite trend. From the present work, 400° C. can be considered as the optimal temperature accounting for trade-off between guaiacol conversion and carbon recovery in liquid products. (0023) The kinetic behavior of Pt—Bi catalyst at 400° C. was studied by varying feed rates of guaiacol and CH4 under otherwise standard conditions. The data for each contact time, taken at 60 min TOS, is shown in FIG. 4. It illustrates that phenol, as the main product, rises with contact time increase, while the other two products remain essentially unchanged. As compared to the PtH2 case (FIGS. 1a and 1b; 300° C., 0.3 g catalyst·hr/g guaiacol), the results of FIGS. 3a, 3b and 4 demonstrate that equivalent guaiacol conversion can be achieved for the case of Pt—Bi catalyst with methane by compensating with either higher temperature or longer contact time (>0.5 g catalyst·hr/g guaiacol). (0024) In the present work, CH4 is used as novel reductant to deoxygenate guaiacol, a model compound of pyrolysis bio-oils. With the Pt/C catalyst, CH4 exhibits as good deoxygenation performance as H2 with respect to guaiacol conversion and product distribution. The lifetime of Pt/C catalyst, however, was low (<3 hrs). With addition of bismuth as promoter, the lifetime of Pt—Bi/C is extended (no significant deactivation in 5 hrs), although catalyst performance decreases somewhat, which could be compensated by either higher reaction temperature or longer contact time. The current work provides a new approach for bio-oil upgrading using methane as reductant instead of hydrogen. (0025) Those skilled in the art will recognize that numerous modifications can be made to the specific implementations described above. The implementations should not be limited to the particular limitations described. Other implementations may be possible.
9
A
B
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10
in aq. phosphate buffer; [D3]acetonitrile; water-d2
T=20°C; pH=5; Kinetics;
Liu, Bin; Thayumanavan
Journal of the American Chemical Society, 2017 , vol. 139, # 6 p. 2306 - 2317 Title/Abstract Full Text View citing articles Show Details
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With deutero-chloric acid; water-d2
Reagent/catalyst;
Rx-ID: 45089515 Find similar reactions
Gong, Wanjun; Ma, Jun; Zhao, Zhiyong; Gao, Fang; Liang, Feng; Zhang, Haijun; Liu, Simin
Journal of Organic Chemistry, 2017 , vol. 82, # 6 p. 3298 - 3301 Title/Abstract Full Text View citing articles Show Details
11
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With calcium hypochlorite; acetic acid in water; acetonitrile
T=20°C; 1.5 h; regioselective reaction;
Rx-ID: 45753755 Find similar reactions
Gilissen, Pieter J.; Blanco-Ania, Daniel; Rutjes, Floris P. J. T.
Journal of Organic Chemistry, 2017 , vol. 82, # 13 p. 6671 - 6679 Title/Abstract Full Text Show Details
A
B
C
D
E
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12
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A: 10% B: 48% C: 11% D: 7% E: 7%
With nickel supported catalyst in methanol; water
T=260°C; P=7500.75 Torr; 4 h; Inert atmosphereAutoclave; Reagent/catalyst; Hide Experimental Procedure
Chinese Academy Of Sciences Process Engineering Institute; Wang Ze; Fu Chaolin; Song Wenli; Lin Weigang; Li Songgeng
Patent: CN106496165 A, 2017 ; Location in patent: Paragraph 0045-0046 ; Title/Abstract Full Text Show Details
2:
2 g of furfural,10g water,36 g of methanol and 0.5 g of catalyst into a 100 mL autoclave,To the reactor charge and discharge N2 three times,To purge the air in the reactor,And then continue to fill N2 to make the initial pressure within the kettle to 1MPa.The autoclave was heated to 260 ° C at a heating rate of 3 ° C / min,And stay at this temperature for 4h,After the reaction, the reaction vessel was transferred to cold water and cooled to room temperature (cooling rate of about 10 ° C / min)The gas and liquid products in the autoclave were quantitatively analyzed when the temperature of the reactor was stable.The results showed that the conversion rate of furfural was 95percent under the catalyst and reaction conditions,Furan yield reached 52percentMethyl furan yield of 29percentThe yield of cyclopentanone was 4percentButanol yield of 7percentThe yield of tetrahydrofuran was 1percentThe other components were yielded at 2percent. A
13
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C
D
E
F
G
H
I
J
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With hydrogen in water
T=199.84°C; P=60006 Torr; 3 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure
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Mironenko; Belskaya; Lavrenov; Likholobov
Russian Chemical Bulletin, 2017 , vol. 66, # 4 p. 673 - 676 Izv. Akad. Nauk, Ser. Khim., 2017 , # 4 p. 673 - 676,4 Title/Abstract Full Text Show Details
Hydrogenation of furfural (99percent, Sigma—Aldrich) in aqueous solution (3.5 wt.percent, 100 mL) in the presence of PdRu/CNTs (300 mg) was carried out in a periodic mode in a Limbo Liautoclave (Büchi AG) at a temperature of 473 K and overallpressure of 8 MPa with continuous stirring of the reaction mixture (1500 min–1). The duration of any experiment was 3 h.
14
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Rx-ID: 276442 Find similar reactions
48%
With dihydrogen peroxide; vanadium phosphorus oxide in acetonitrile
T=50°C; 20 h;
Pillai, Unnikrishnan R.; Sahle-Demessie, Endalkachew
New Journal of Chemistry, 2003 , vol. 27, # 3 p. 525 - 528 Title/Abstract Full Text View citing articles Show Details
12.15%
Stage #1: With 3C46H56N2O4(4-)*7Cu(2+)*2HO(1-)*2C3H7NO*2H2O in acetonitrile
T=55°C; Stage #2: With dihydrogen peroxide in water; acetonitrile
T=55°C; 6 h;
Fang, Yu; Gong, Wei; Liu, Lujia; Liu, Yan; Cui, Yong
Inorganic Chemistry, 2016 , vol. 55, # 20 p. 10102 - 10105 Title/Abstract Full Text View citing articles Show Details
With ethyl bromide; hydrogen bromide; oxygen
T=185°C;
Shell Devel. Co.
Patent: US2391740 , 1944 ; Full Text Show Details
Hide Details
in pyridine
GoAggIII (acetic acid, FeCl3*6 H2O, Zn, picolinic acid), other Gif systems, relative reactivity with
Barton, Derek H. R.; Doller, Dario; Geletii, Yurii V.
Tetrahedron Letters, 1991 , vol. 32, # 31 p. 3811 - 3814 Title/Abstract Full Text View citing articles Show Details
46 % Chromat.
With cis-lt;RuVI(6,6'-Cl2bpy)2O2gt;lt;ClO4gt; in acetonitrile
T=20°C; Oxidation; 0.5 h;
Che; Cheng; Chan; Lau; Mak
Journal of Organic Chemistry, 2000 , vol. 65, # 23 p. 7996 - 8000 Title/Abstract Full Text View citing articles Show Details
With oxygen
T=19.84°C; Neat (no solvent)UV-irradiation;
Tada, Mizuki; Akatsuka, Yusaku; Yang, Yong; Sasaki, Takehiko; Kinoshita, Mutsuo; Motokura, Ken; Iwasawa, Yasuhiro
Angewandte Chemie - International Edition, 2008 , vol. 47, # 48 p. 9252 - 9255 Title/Abstract Full Text View citing articles Show Details
With iron(III) chloride; thymidyl acetic acid; dihydrogen peroxide in water; acetonitrile
T=60°C; 10 h;
Al-Hunaiti, Afnan; Räisänen, Minnä; Repo, Timo
Chemical Communications, 2016 , vol. 52, # 10 p. 2043 - 2046 Title/Abstract Full Text View citing articles Show Details
cyclohexane; KineticsMechanism;
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15
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Rx-ID: 747217 Find similar reactions
100%
With oxygen; palladium(II) sulfate; PdSO4-H3PMo6W6O40 in cyclohexane; water
T=30°C; 6 h;
Ogawa, Haruo; Fujinami, Hideharu; Taya, Kazuo; Teratani, Shousuke
Journal of the Chemical Society, Chemical Communications, 1981 , # 24 p. 1274 - 1275 Title/Abstract Full Text View citing articles Show Details
100%
With oxygen; H3PMo6W6O40 in cyclohexane; water
T=29.9°C; P=760 Torr; 6 h;
Ogawa; Fujinami; Taya; Teratani
Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1908 - 1913 Title/Abstract Full Text View citing articles Show Details
100%
With palladium(II) sulfate; oxygen; H3PMo6W6O40 in cyclohexane; water
T=29.9°C; P=760 Torr; 6 h; other time, other Pd(II) salt, other concentration of catalyst; Product distributionRate constant;
Ogawa; Fujinami; Taya; Teratani
Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1908 - 1913 Title/Abstract Full Text View citing articles Show Details
Hide Details
80.2%
72.2%
With oxygen; palladium diacetate; scandium tris(trifluoromethanesulfonate) in water; acetonitrile T=80°C; Wacker Oxidation; P=15201 Torr; 24 h; Autoclave; Reagent/catalyst; With bis(benzonitrile)palladium(II) dichloride; oxygen in water; tert-butyl alcohol
T=60°C; P=3750.38 Torr; 5 h; Autoclave; Reagent/catalystSolventTemperaturePressure; Hide Experimental Procedure
NipponZeonCo., Ltd.; University of Tokyo; Sugawara, Takashi; Nakano, Keita; Kobayashi, Shu
Patent: JP2016/88903 A, 2016 ; Location in patent: Paragraph 0034; 0039 ; Title/Abstract Full Text Show Details
5:
To the autoclave made from 40-mL stainless steel, dichlorobis (benzonitrile) palladium 38.4 mg (0.10mmol), After preparing 5.0 mL of methanol, and 0.5 mL of water as 272.5 mg (4.0mmol) and a solvent and sealing cyclopentene, oxygen gas was introduced and 0.5MPa (G) was pressurized. After having heated the whole picture, stirring at 60 degrees C for 5 hours and oxidizing cyclopentene, the whole picture was cooled, and at 0 degree C, it agitated for 1 hour, it ranked next, and returned the pressure in autoclave to ordinary pressure.THF was added to reaction mixture and dilution liquid was obtained. Gas chromatographic assay was conducted about the filtrate obtained by carrying out filtration removal of the solid in this dilution liquid using a 0.5-micrometer filter.As a result, the yield of cyclopentanone was 66.3percent to raw material cyclopentene. The survival rate of cyclopentene was 0percent. In the working example 1, the solvent was changed into 1-butanol and oxidation reaction of cyclopentene, filtration treatment of reaction mixture, and analysis of filtrate were conducted like the working example 1 except not having added water further.As a result, the yield of cyclopentanone was 72.2percent to raw material cyclopentene. The survival rate of cyclopentene was 0percent. 50%
With oxygen; copper(I)ketenide
T=20°C; P=1360 Torr; 10 h;
'Femi-Onadeko, Bankole
Acta Chimica Hungarica, 1986 , vol. 122, # 2 p. 175 - 180 Title/Abstract Full Text Show Details
44%
With N,N,N,N,N,N-hexamethylphosphoric triamide; dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride in 1,2-dichloro-ethane
T=50°C; 19 h;
Hosokawa; Aoki; Takano; Nakahira; Yoshida; Murahashi
Journal of the Chemical Society - Series Chemical Communications, 1991 , # 21 p. 1559 - 1560 Title/Abstract Full Text View citing articles Show Details
With oxygen; palladium dichloride
Smidt et al.
Angewandte Chemie, 1959 , vol. 71, p. 176,180,182 Angewandte Chemie, 1962 , vol. 74, p. 93 Full Text View citing articles Show Details
Qin, Shuhao; Dong, Lei; Chen, Zhuqi; Zhang, Sicheng; Yin, Guochuan
Dalton Transactions, 2015 , vol. 44, # 40 p. 17508 - 17515 Title/Abstract Full Text View citing articles Show Details
75 % Chromat.
With palladium diacetate; p-benozquinone in water; acetonitrile
Ambient temperatureelectrolysis was used for the oxidation;
Tsuji, Jiro; Minato, Makoto
Tetrahedron Letters, 1987 , vol. 28, # 32 p. 3683 - 3686 Title/Abstract Full Text View citing articles Show Details
With lithium borohydride; sodium dichromate; sulfuric acid; boron trifluoride diethyl etherate
1.) ethyl ether, 25-30 deg C, 2 h; 2.) water, ethyl ether, reflux, 2 h; Yield given. Multistep reaction;
Brown, Herbert C.; Garg, Chandra P.
Tetrahedron, 1986 , vol. 42, # 20 p. 5511 - 5514 Title/Abstract Full Text View citing articles Show Details
With oxygen; PdCl2(DEAc)2( in ethanol
T=30°C; P=860 Torr; 8 h; oxidation with other palladium-complex; Product distribution;
Takehira, Katsuomi; Hayakawa, Takashi; Orita, Hideo
Chemistry Letters, 1985 , p. 1835 - 1838 Title/Abstract Full Text Show Details
99 % Chromat.
With dihydrogen peroxide; tetraphenylphosphonium; sodium hydrogencarbonate; WO(O2) (QO)4 in acetonitrile
T=25°C; 0.25 h;
Maiti, Swarup K.; Dinda, Subhajit; Gharah, Narottam; Bhattacharyya, Ramgopal
New Journal of Chemistry, 2006 , vol. 30, # 3 p. 479 - 489 Title/Abstract Full Text View citing articles Show Details
With dinitrogen monoxide
T=200°C; 20 h; pressure;
Starokon; Dubkov; Babushkin; Parmon; Panov
Advanced Synthesis and Catalysis, 2004 , vol. 346, # 2-3 p. 268 - 274 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: KMnO4 / H2O / -5 °C 2: pyridine / 2.5 h / 3 °C 3: acetic acid / rate constant: 171.4E5
View Scheme
Wistuba, Eckehardt; Ruechardt, Christoph
Tetrahedron Letters, 1981 , vol. 22, # 41 p. 4069 - 4072 Title/Abstract Full Text View citing articles Show Details
With dinitrogen monoxide
T=150 - 225°C; P=3800.26 - 19001.3 Torr; 3 - 12 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 2-3 ; Title/Abstract Full Text Show Details
1; 2; 3; 4; 5; 6; 7; 8:
33 cm3 of cyclopentene (Aldrich, 99percent) are poured into a 100 cm3 reactor made from stainless steel and provided with a stirrer (Parr Co.). The reactor is purged with nitrous oxide, and then the pressure of nitrous oxide is brought to 10 atm. The reactor is heated to 197° C. and maintained at this temperature during 5 hrs. On completion of the reaction, the reactor is cooled down to room temperature, the pressure is measured, and the final composition of the gaseous and liquid phases is analyzed by gas chromatography and chromatography-mass spectrometry techniques. From the obtained data the conversion of cyclopentene and the selectivity of the reaction for cyclopentanone are calculated; where CCyEN0 is the initial cyclopentene concentration; CCyON is the cyclopentene concentration in reaction products; ΣCside is the total concentration of by-products. In the case of large conversions, the value X can be calculated also from the difference between the initial and final concentrations of cyclopentene: Example 2 is similar to Example 1, the difference being in that the reaction is carried out at 195° C. during 12 hours. Example 3 is similar to Example 2, the difference being in that the reaction is carried out at a temperature of 150° C. Example 4 is similar to Example 3, the difference being in that the reaction is carried out at 175° C. during 10 hours. Example 5 is similar to Example 4, the difference being in that the reaction is carried out at 225° C. during 3 hours. TABLE 1 Example T (° C.) Time (hrs) X (percent) S (percent) 1 197 5 7.7 98 2 195 12 15.6 97 3 150 12 3.5 97.5 4 175 10 8.5 98 5 225 3 13 99 Example 6 This Example is a comparative one. The experiment is carried out as in Example 1, the difference being in that the reactor is charged with 5 ml of cyclopentene. With such charging under the reaction conditions the whole of the cyclopentene is in the gaseous phase. As a result of the experiment, the conversion of cyclopentene was approximately 0.5percent. This result indicates that under the abovesaid conditions the reaction in the gas phase practically does not go. EXAMPLES 7-8 These Examples, as compared with Example 1, demonstrate the influence of the nitrous oxide concentration on the process characteristics (Table 2). The nitrous oxide concentration in the reaction mixture is preset by the value of its initial pressure at room temperature, PN2O0. Example 7 is similar to Example 1, the difference being in that the initial pressure of nitrous oxide at room temperature in this experiment is set to be equal to 25 atm. Example 8 is similar to Example 1, the difference being in that the initial pressure of nitrous oxide in this experiment is set to be equal to 5 atm. TABLE 2 ExamplePN2O 0 (atm) T ° C.) X (percent) S (percent) 1 10 197 7.7 98 7 25 197 20.5 99 8 5 197 4.0 98
With dinitrogen monoxide; 1 wt silver/SiO2
T=197°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
10:
Examples 9-10 (Table 3) demonstrate the possibility of carrying out the process in the presence of a catalyst. Example 9 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.15 g of Fe2O3/SiO2 (2.8 wt. percent of Fe2O3). The catalyst is prepared by impregnating SiO2 with a solution of FeCl3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. Example 10 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.5 g of Ag/SiO2 (1 wt. percent of Ag). The catalyst is prepared by impregnating SiO2 with a solution of AgNO3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. TABLE 3 Example Catalyst T (° C.) X (percent) S (percent) 9Fe2O3/SiO2 197 7.5 97.5 10Ag/SiO2 197 8 97
With dinitrogen monoxide
T=197°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
9:
Examples 9-10 (Table 3) demonstrate the possibility of carrying out the process in the presence of a catalyst. Example 9 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.15 g of Fe2O3/SiO2 (2.8 wt. percent of Fe2O3). The catalyst is prepared by impregnating SiO2 with a solution of FeCl3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. Example 10 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.5 g of Ag/SiO2 (1 wt. percent of Ag). The catalyst is prepared by impregnating SiO2 with a solution of AgNO3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. TABLE 3 Example Catalyst T (° C.) X (percent) S (percent) 9Fe2O3/SiO2 197 7.5 97.5 10Ag/SiO2 197 8 97
With dinitrogen monoxide in n-heptane
T=220°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
14:
Example 14 is similar to Example 13, the difference being in that instead of acetonitrile use is made of heptane and the reaction is carried out at 220° C. for 5 hrs.
12:
With dinitrogen monoxide in cyclohexane
T=195°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
Example 12 is similar to Example 1, the difference being in that 10 ml of cyclopentene and 50 ml of cyclohexane are poured into the reactor.
With dinitrogen monoxide in acetonitrile
T=150°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
13:
Example 13 is similar to Example 3, the difference being in that 10 ml of cyclopentene and 50 ml of acetonitrile are poured into the reactor.
With dinitrogen monoxide in 2-methyl-propan-1-ol
T=195°C; P=7600.51 Torr; 5 h; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
11:
These Examples demonstrate the possibility of cyclopentene oxidation in the presence of a solvent (Table 4). Example 11 is similar to Example 1, the difference being in that 10 ml of cyclopentene and 75 ml of isobutanol are poured into the reactor.
With dinitrogen monoxide
T=195°C; P=32682.2 Torr; 12 h; Mixed with argon; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
19:
Example 19 is similar to Example 17, the difference being in that instead of nitrogen argon is used, in which the concentration of nitrous oxide is 40percent. The initial pressure of the mixture of N2O and Ar is set to be 43 atm.
With dinitrogen monoxide
T=195°C; P=32682.2 Torr; 12 h; Mixed with carbon dioxide; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
20:
Example 20 is similar to Example 19, the difference being in that carbon dioxide gas is used instead of argon.
With dinitrogen monoxide
T=195 - 225°C; P=24321.6 - 74485 Torr; 3 - 12 h; Mixed with nitrogen; Product distribution / selectivity; Hide Experimental Procedure
Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna
Patent: US2006/106258 A1, 2006 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details
15; 16; 17; 18:
Examples 15-20 (Table 5) demonstrate the possibility of carrying out the reaction with diluted mixtures of nitrous oxide. Example 15 is similar to Example 7, the difference being in that instead of pure nitrous oxide its mixture with an inert gas-nitrogen is fed to the reactor, in which mixture the concentration of N2O is 70percent The initial pressure of the mixture in the reactor (P0) is set to be 49 atm. Example 16 is similar to Example 15, the difference being in that the concentration of N2O in the mixture with nitrogen is 20percent. Example 17 is similar to Example 16, the difference being in that the initial pressure in the reactor is set to be 98 atm. The reaction is carried out at 195° C. for 12 hours. Example 18 is similar to Example 15, the difference being in that the concentration of nitrous oxide is 50percent, and the initial pressure of the mixture of N2O and N2 is set to be 32 atm. The reaction is carried out at 225° C. for 3 hours.
With dinitrogen monoxide
T=280°C; P=225023 Torr;
BASF AKTIENGESELLSCHAFT
Patent: WO2006/32532 A1, 2006 ; Location in patent: Page/Page column 23-24 ; Title/Abstract Full Text Show Details
With dinitrogen monoxide
T=280°C; P=825.083 - 8250.83 Torr; Gas phase; Product distribution / selectivity; Hide Experimental Procedure
BASF SE Patents, Trademarks and Licences
Patent: US2010/179352 A1, 2010 ; Location in patent: Page/Page column 7-8 ; Title/Abstract Full Text Show Details
1:
Example 1 was carried out in a reactor with downstream flash and distillation stage.The reactor consists of a series of 16 single tubes (outer diameter=10 mm, wall thickness=2 mm, inner diameter=6mm, length=5.3 m) that were spirally coiled (radius r=125 mm, pitch P=30 mm). The reaction volume inclusive the connecting parts is 2510 ml in total.The tube is equipped with a double jacket (outer tube: outer diameter=20 mm, wall thickness=2 mm, annular gap width=3 mm) through which a cooling liquid is pumped in direct flow to remove the reaction heat (Marlotherm SH of the firm Sasol). The temperature of the entering cooling agent is adjusted by means of an external thermostat at 280+/-2° C. Directly at the exit of the reactor is a pressure maintenance that keeps the pressure in the reactor constantly at 280 bar.The fresh cyclopentene is metered into the reactor with 172.5 g/h. Cyclopentene is obtained from the distillation of a C5-cut of a steam cracker and has the following composition (percent by weight): cyclopentene (ca. 93.2percent), cyclopentane (ca. 5.7percent), 2-methyl-2-butene (ca. 1.1percent), 2,2-dimethylbutane (ca. 0.17percent).By mixing of this stream with a cyclopentene feedback stream a stream of the following composition is generated: cyclopentene (ca. 48.8percent), cyclopentane (ca. 46.2percent), 2-methyl-2-butane (ca. 3.1percent), acetone (ca. 2.0percent), 2,2-dimethylbutane (ca. 0.96percent). This stream is then metered to the reactor by means of a metering pump (rate of flow: 1632 g/h).As further stream liquid N2O (content of N2O>99.5percent by volume, firm Messer Griesheim) is metered to the reactor with ca. 99.2 g/h. The molar ratio of cyclopentene to N2O in the reactor feed is 0.192 mol/mol.The cyclopentene conversion in a straight passage is 19.6percent and the N2O conversion is ca. 99.6percent. After pressure maintenance the reaction discharge is expanded in two stages with two flash vessels being operated at 11 bara and 1.1 bara to a pressure of 1.1 bara and cooled down. The gaseous components are separated and in a secondary cooler (operated at +5° C.) the hydrocarbons contained therein are condensed out as completely as possible. The gas phase (ca. 64.5 g/h) has the following composition: N2 (96.4percent by volume), N2O (0.41percent by volume), ethylene (0.28percent by volume), cyclopentene (0.37percent by volume), cyclopentane (0.33percent by volume), further C5-components (545 vppm).The obtained liquid phase is separated in a distillation column (bubble cap column with 5 column units 106 cm*50 mm, each 10 plates). 187.7 g/h of a stream having the following composition (percent by weight) are obtained as bottom product: cyclopentanone (ca. 96.8percent), cyclopentane (ca. 1.3percent), 4-pentenal (ca. 1.3percent), isopropylmethylketone (ca. 0.8percent), cyclopentenoxid (ca. 0.5percent), cyclopentene-dimers (ca. 0.5percent), cyclopentene (ca. 0.03percent).Of the top product containing 43.4percent cyclopentene but no cyclopentanone about 14.9 g/h are discarded in order to avoid the increase of by-components, in particular of acetone and 2-methyl-2-butene. The residual (ca. 1460 g/h) is feeded back as cyclopentene-feedback stream to the mixing tap together with fresh-C5.According to this operation mode the space-time yield is ca. 72.4 g cyclopentanone/liter/reaction volume/hour. Per kg of cyclopentanone produced ca. 8.2 kg cyclopentene/cyclopentane mixture have to be separated off and for the most part are feeded back. The required energy for the distillation is 0.73 kWh/kg cyclopentanone.
With dinitrogen monoxide
T=239.5°C; Industry scale; Product distribution / selectivity; Hide Experimental Procedure
BASF SE
Patent: US2011/152576 A1, 2011 ; Location in patent: Page/Page column 9-10 ;
Title/Abstract Full Text Show Details
1:
Example 1 The pilot plant according to FIG. 1 is used.Through stream 2, the fresh cyclopentene feed is metered in at 116.4 g/h. This originates from the distillation of a C5 cut of a steamcracker and has the following composition (percent by weight): cyclopentene (approx. 95.1percent), cyclopentane (approx. 3.4percent), 2-methyl-2-butene (approx. 1.2percent).This stream 2 is first mixed with stream 3 (return cyclopentene) in order to obtain a stream which has the following composition: cyclopentene (approx. 46.3percent), cyclopentane (approx. 51.9percent), 2-methyl-2-butene (approx. 0.9percent), 2,2-dimethylbutane (approx. 0.81percent).This stream is then metered into the reactor with a metering pump (flow rate: approx. 2076 g/h). Through stream 1, liquid dinitrogen monoxide (dinitrogen monoxide content >99.8percent by volume, from Messer Griesheim) is metered into the reactor at approx. 74 g/h. The molar cyclopentene:dinitrogen monoxide ratio in the reactor feed is 0.11 mol/mol. The reactor consists of a tube (external diameter=60.3 mm, wall thickness=2.4 mm, length=3500 mm) filled with thin-wall stainless steel Raschig rings (6.x.6.x.0.3 mm). To determine the longitudinal temperature profile, a thermowell of external diameter 16 mm was installed along the reactor axis and provided with a 15-point thermocouple. The reaction volume is (minus random packings and thermowell), including connecting pieces, approx. 7 l in total. The pressure in the reactor is adjusted to 100 bar with a suitable pressure-retaining device at the reactor outlet.The tube is provided with an insulating jacket composed of a nanoporous inorganic foam from Microtherm (two layers of thickness in each case 50 mm). In order to reduce the heat losses even further, a three-part trace-heating system is also installed on the outside of the insulating jacket, and is adjusted to (v.u.) 256, 275 317° C. (preliminary tests without addition of dinitrogen monoxide ensured that the heat losses are only very low. When the reactor inlet temperature is approx. 260° C., the remaining heat losses lead to a cooling by merely 3° C. up to the reactor outlet). The residence time distribution of the reactor was determined in a preliminary test with a radioactive marker. The Bodenstein number determined has the value of 117, which corresponds to an equivalent stirred tank cascade with 58 stirred tanks.The feed stream is fed into the reactor from the bottom via a heated inlet nozzle, in which the feed stream is also heated. At a reactor inlet temperature of 239.5° C. (measured at the lowermost thermocouple in the thermowell), the cyclopentene conversion in straight pass is 11percent and the dinitrogen monoxide conversion approx. 96percent. The selectivity for cyclopentanone based on cyclopentene is 96.8percent. The reactor output has a temperature of 295° C. The adiabatic temperature increase is thus 55.5° C. The reactor output is decompressed to 1 bar in a two-stage decompression and cooled. The gaseous components are removed and, in an aftercooler (which is operated at +5° C.), the hydrocarbons present therein are very substantially condensed out.The liquid phase, which of the liquid reactor output and of the condensate, is separated in a distillation column (bubble-cap tray column with 20 trays and liquid side draw). The bottom product obtained is 138.7 g/h of a stream with the following composition (percent by weight): cyclopentanone (approx. 95.3percent), cyclopentane (approx. 0.8percent), 4-pentenal (approx. 1.3percent), cyclopentene oxide (approx. 0.37percent), cyclopentene dimers (approx. 0.53percent), cyclopentene (approx. 0.08percent). The side draw product which comprises 45.6percent cyclopentene is recycled as stream 3 to the reactor.The combined gas phases (from decompression & top of the recycle column, approx. 47.7 l/h) have the following composition: N&2 (81.1percent by volume), dinitrogen monoxide (2.46percent by volume), cyclopentene (0.96percent by volume), cyclopentane (0.48percent by volume).
With Pd-Cu(5:1)/γ-Al2O3; oxygen in ethanol
T=100°C; P=7500.75 Torr; 7 h; Autoclave; Catalytic behavior; Reagent/catalystSolventTemperaturePressure; chemoselective reaction; Hide Experimental Procedure
Liu, Wei-Wei; Feng, Yi-Si; Wang, Guang-Yu; Jiang, Wei-Wei; Xu, Hua-Jian
Chinese Chemical Letters, 2016 , vol. 27, # 6 p. 905 - 909 Title/Abstract Full Text View citing articles Show Details
Catalytic reaction:
In a typical procedure, 15 mL cyclopentene (0.17 mol), 60 mL ethyl alcohol (1.03 mol) and Pd–Cu (5:1)/γ-Al2O3 catalyst (0.24 g, 2.0 wtpercent of cyclopentene) were added into 0.1 L closed autoclave. The mixture was stirred (400 rpm/min) under 1.0 MPa oxygen pressure at 100 °C for 7 h. Specific parameters are provided in Supporting information.
16
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Rx-ID: 1792690 Find similar reactions
100%
With p-mentha-1,8-diene; palladium on activated charcoal
0.5 h; Heating;
Holleben, Maria Luiza A. von; Zucolotto, Monica; Zini, Claudia A.; Oliveira, Eduardo R.
Tetrahedron, 1994 , vol. 50, # 4 p. 973 - 978 Title/Abstract Full Text View citing articles Show Details
100%
With hydrogen; SC-1 Ni2B in methanol
T=25°C; P=760 Torr; 24 h;
Belisle, Christopher M.; Young, Yvette M.; Singaram, Bakthan
Tetrahedron Letters, 1994 , vol. 35, # 31 p. 5594 - 5598 Title/Abstract Full Text Show Details
99%
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) in chloroform
0.5 h; Ambient temperature;
Keinan, Ehud; Greenspoon, Noam
Journal of the American Chemical Society, 1986 , vol. 108, # 23 p. 7314 - 7325 Title/Abstract Full Text View citing articles Show Details
Hide Details
80%
74%
With diisobutyl-aluminum-ethylate in diethyl ether
T=25°C; 24 h;
Hide Experimental Procedure
Cha, Jin Soon; Kwon, Oh Oun; Kwon, Sang Yong
Organic Preparations and Procedures International, 1996 , vol. 28, # 3 p. 355 - 360 Title/Abstract Full Text View citing articles Show Details
University of Massachusetts
Patent: US5917074 A1, 1999 ; Title/Abstract Full Text Show Details
7:Olefination of Cyclopentanone with TIPS-propargyl fluorophosphonate
Example 7 Olefination of Cyclopentanone with TIPS-propargyl fluorophosphonate The reaction was carried out as in Example 2, using cyclopentenone as the carbonyl compound. Obtained in 74percent yield: 1 H NMR (CDCl3) δ 1.10 (apparent s, 21H), 1.68-1.73 (m, 4H), 2.38-2.45 (m, 4H); 19 F NMR δ -114 (s); IR (film, NaCl) v 2960, 2865, 2145, 1675, 1460, 1245, 1155 and 885 cm-1. 51%
With formic acid; 3,7-dimethyl10-p-tolyl-5-deazaflavins
T=120°C; 25 h;
Yoneda, Fumio; Kuroda, Kazunori; Tanaka, Kiyoshi
Journal of the Chemical Society, Chemical Communications, 1984 , # 17 p. 1194 - 1195 Title/Abstract Full Text View citing articles Show Details
100 % Chromat.
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silica gel in benzene
T=80°C; 17 h;
Nakamura, Kaoru; Fujii, Masayuki; Ohno, Atsuyoshi; Oka, Shinzaburo
Tetrahedron Letters, 1984 , vol. 25, # 36 p. 3983 - 3986 Title/Abstract Full Text View citing articles Show Details
60.3 % Chromat.
With KHBPh3 in tetrahydrofuran
T=-78°C; 2 h;
Kim, Kwan Eung; Park, Soo Bong; Yoon, Nung Min
Synthetic Communications, 1988 , vol. 18, # 1 p. 89 - 96 Title/Abstract Full Text Show Details
51 % Chromat.
With formic acid; 3,7-dimethyl10-p-tolyl-5-deazaflavins
T=120°C; 25 h;
Nagamatsu, Tomohisa; Kuroda, Kazunori; Mimura, Norio; Yanada, Reiko; Yoneda, Fumio
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 9 p. 1125 - 1128 Title/Abstract Full Text View citing articles Show Details
13 % Chromat.
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid in toluene
T=100°C; 15 h;
Inoue, Yoshio; Imaizumi, Shin; Itoh, Hiromitsu; Shinya, Takao; Hashimoto, Harukichi; Miyano, Sotaro
Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 3020 - 3022 Title/Abstract Full Text Show Details
With hydrogen; silica gel; copper in toluene
T=90°C; P=760 Torr; 24 h; Yield given;
Ravasio, Nicoletta; Antenori, Marisa; Gargano, Michele; Mastrorilli, Piero
Tetrahedron Letters, 1996 , vol. 37, # 20 p. 3529 - 3532 Title/Abstract Full Text View citing articles Show Details
With hydrogen in propan-1-ol
T=25°C; enthalpy of hydrogenation; Thermodynamic data;
Rogers, Donald W.; Zhao, Yeping; Traetteberg, Marit; Hulce, Martin; Liebman, Joel
Journal of Chemical Thermodynamics, 1998 , vol. 30, # 11 p. 1393 - 1400 Title/Abstract Full Text View citing articles Show Details
87 % Chromat.
With dicobalt octacarbonyl; water in DME
2 h; Heating;
Lee, Hee-Yoon; An, Mihyun
Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2775 - 2778 Title/Abstract Full Text View citing articles Show Details
With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; isopropyl alcohol; bis(1,5cyclooctadiene)diiridium(I) dichloride in toluene
T=80°C; 4 h;
Sakaguchi; Yamaga; Ishii
Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4710 - 4712 Title/Abstract Full Text View citing articles Show Details
With hydrogen; palladium nanoparticles embedded in polysiloxane matrix T=120°C; P=600.06 Torr; Kinetics;
Trapp, Oliver; Weber, Sven K.; Bauch, Sabrina; Hofstadt, Werner
Angewandte Chemie - International Edition, 2007 , vol. 46, # 38 p. 7307 - 7310 Title/Abstract Full Text View citing articles Show Details
> 99 %Chromat.
With formic acid; C15H16IrN2O3(1+)*O4S(2-) in water
T=40°C; pH=7.3; 2 h; Inert atmosphere; chemoselective reaction;
Himeda, Yuichiro; Onozawa-Komatsuzaki, Nobuko; Miyazawa, Satoru; Sugihara, Hideki; Hirose, Takuji; Kasuga, Kazuyuki
Chemistry - A European Journal, 2008 , vol. 14, # 35 p. 11076 - 11081 Title/Abstract Full Text View citing articles Show Details
With old yellow enzyme from Geobacillus kaustophilus; NADPH
Enzymatic reaction;
Schittmayer, Matthias; Glieder, Anton; Uhl, Michael K.; Winkler, Andreas; Zach, Simone; Schrittwieser, Joerg H.; Kroutil, Wolfgang; MacHeroux, Peter; Gruber, Karl; Kambourakis, Spiros; Rozzell, J. David; Winkler, Margit
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 2-3 p. 268 - 274 Title/Abstract Full Text View citing articles Show Details
With ene-reductase from Deinococcus radiodurans; NADH; sodium chloride in aq. buffer T=30°C; pH=7.4; 5 h; Enzymatic reaction; Reagent/catalyst; Hide Experimental Procedure
Litthauer; Gargiulo; Van Heerden; Hollmann; Opperman
Journal of Molecular Catalysis B: Enzymatic, 2014 , vol. 99, p. 89 - 95 Title/Abstract Full Text View citing articles Show Details
2.4. Enzyme assays
General procedure: Biotransformation for substrate scope and selectivity analysis were performed in 1 mL reaction volumes consisting of 2 mM NADH and 1 mM substrate, purified enzyme (20 μg) in 20 mM MOPS-NaOH (pH 7.4) with 0.1 M NaCl buffer at 30 °C. Conversions were determined after 5 h of incubation. For GC–MS analysis, reaction mixtures were extracted using an equal volume of ethyl acetate and samples separated on a FactorFour VF-5 ms column (30 m×0.25 mm×0.25 μm, Varian). Chiral separation of the reduction products of R- and S-carvone, 2-methylcyclopentenone and ketoisophorone were performed on a Astec Chiraldex G-TA column (30 m×0.25 mm×0.25 μm, Sigma–Aldrich) and compared to reference activities [37] or the MS fragmentation of diastereomers [38]. For HPLC analysis, reactions were stopped by the addition of 10 μL of concentrated HCl and samples separated on a Jupiter 5 μm C18 300 column (250 mm×4.6 mm, Phenomenex).
With Wilkinson's catalyst; hydrogen in toluene
T=120°C; P=1500.15 Torr;
Haywood, Tom; Miller, Philip W.
ChemCatChem, 2014 , vol. 6, # 5 p. 1199 - 1203 Title/Abstract Full Text View citing articles Show Details
With xenobiotic reductase A from Pseudomonas putida; NADPH in aq. phosphate buffer; N,Ndimethyl-formamide
T=30°C; pH=7.5; 1 h; Enzymatic reaction; Reagent/catalyst;
Peters, Christin; Koelzsch, Regina; Kadow, Maria; Skalden, Lilly; Rudroff, Florian; Mihovilovic, Marko D.; Bornscheuer, Uwe T.
ChemCatChem, 2014 , vol. 6, # 4 p. 1021 - 1027 Title/Abstract Full Text View citing articles Show Details
96 %Chromat.
With hydrogen in n-heptane
T=20°C; P=2068.65 Torr; 2 h; Autoclave; chemoselective reaction;
Natour, Suzana; Abu-Reziq, Raed
RSC Advances, 2014 , vol. 4, # 89 p. 48299 - 48309 Title/Abstract Full Text View citing articles Show Details
97 %Chromat.
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium carbonate; isopropyl alcohol
T=85°C; 5 h; Inert atmosphereSchlenk technique; chemoselective reaction;
Chen, Shu-Jie; Lu, Guo-Ping; Cai, Chun
RSC Advances, 2015 , vol. 5, # 17 p. 13208 - 13211 Title/Abstract Full Text View citing articles Show Details
With Chr-OYE1 (old yellow enzyme from chryseobacterium sp. CA49); β-nicotinamide adenine dinucleotide, oxidized form in aq. phosphate buffer
T=30°C; pH=7.0; 0.0333333 h; Enzymatic reaction; Hide Experimental Procedure
Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu
Journal of Molecular Catalysis B: Enzymatic, 2016 , vol. 123, p. 91 - 99 Title/Abstract Full Text View citing articles Show Details
2.5 Bioreduction of activated alkenes and product analysis
General procedure: The bioreduction of various substrates was performed in 1-ml reaction system containing 100mM potassium phosphate buffer (pH 7.0), 10mM NADH, 5mM substrate, and 50μg purified Chr-OYE1 or 500μg purified Chr-OYE2. After 2-min or 16-h incubation at 30°C for Chr-OYE1 and Chr-OYE2, respectively, the reactions were terminated by extraction with ethyl acetate. The organic phase was analyzed using GC or HPLC. (0013) Preparative-scale biotransformation was performed in 30-ml reaction system for substrates 4a, 6a, and 12a–17a catalyzed with Chr-OYE1. The incubation was continued for 12h. The extracted organic phase was combined and concentrated under reduced pressure. The final product was purified with column chromatography and subjected to GC or HPLC analysis, as well as NMR analysis to confirm the structure and purity.
With enoate reductase YqjM from Bacillus subtilis in ethanol
P=760.051 Torr; IrradiationEnzymatic reaction;
Köninger, Katharina; Gómez Baraibar, Álvaro; Mügge, Carolin; Paul, Caroline E.; Hollmann, Frank; Nowaczyk, Marc M.; Kourist, Robert
Angewandte Chemie - International Edition, 2016 , vol. 55, # 18 p. 5582 - 5585 Angew. Chem., 2016 , vol. 55, # 128 p. 5672 - 5675,4 Title/Abstract Full Text View citing articles Show Details
With old yellow enzyme from Saccharomyces cerevisiae; NADH in aq. buffer T=30°C; pH=7.5; Enzymatic reaction;
Turrini, Nikolaus G.; Eger, Elisabeth; Reiter, Tamara C.; Faber, Kurt; Hall, Mélanie
ChemSusChem, 2016 , vol. 9, # 24 p. 3393 - 3396 Title/Abstract Full Text View citing articles Show Details
17
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Rx-ID: 1980284 Find similar reactions
100%
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 in acetonitrile
Oxidation; 0.0583333 h; Heating;
Minghu, Wu; Guichun, Yang; Zuxing, Chen
Synthetic Communications, 2000 , vol. 30, # 17 p. 3127 - 3131 Title/Abstract Full Text View citing articles Show Details
96%
With potassium permanganate in water; acetonitrile
T=25°C; 1 h;
Wali, Anil; Ganeshpure, Pralhad A.; Satish, Sheo
Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 6 p. 1847 - 1848 Title/Abstract Full Text Show Details
96%
With dihydrogen peroxide; PFC in acetone
T=0 - 10°C; 2.5 h;
Ganguly; Sukai; De
Synthetic Communications, 2001 , vol. 31, # 10 p. 1607 - 1612 Title/Abstract Full Text View citing articles Show Details
Hide Details
95%
With 1-benzyl-1-aza-4-azoniabicyclolt;2.2.2gt;octane periodate in acetonitrile
0.25 h; Heatingcleavage of oxime double bond under anhydrous conditions; other oximes;
Hajipour, Abdol Reza; Mahboubghah, Nasrien
Journal of Chemical Research - Part S, 1998 , # 3 p. 122 - 123 Title/Abstract Full Text View citing articles Show Details
95%
With 1-benzyl-4-aza-1-azoniabiyclolt;2.2.2gt;octane peroxodisulfate in acetonitrile
Oxidation; 0.25 h; Heating;
Hajipour; Mohammadpoor-Baltork; Kianfar
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 2 p. 221 - 224 Title/Abstract Full Text View citing articles Show Details
95%
With benzyltriphenylphosphonium dichromate in acetonitrile
Oxidation; 0.25 h; Heating;
Hajipour, Abdol Reza; Mohammadpoor-Baltork, Iraj; Niknam, Kurosh
Organic Preparations and Procedures International, 1999 , vol. 31, # 3 p. 335 - 341 Title/Abstract Full Text View citing articles Show Details
95%
With Cu(NO3)2-SiO2
oxime cleavage; 0.0166667 h; microwave irradiation;
Ghiaci; Asghari
Synthetic Communications, 2000 , vol. 30, # 21 p. 3865 - 3872 Title/Abstract Full Text View citing articles Show Details
94%
With (cetyl)Me3N(1+)MnO4(1-) in dichloromethane
T=25°C; 1 h;
Vankar, Padma; Rathore, Rajendra; Chandrasekaran, Srinivasan
Journal of Organic Chemistry, 1986 , vol. 51, # 15 p. 3063 - 3065 Title/Abstract Full Text View citing articles Show Details
93%
With hydrogenchloride; sodium chlorite in water
T=20°C; 0.0833333 h; Hide Experimental Procedure
Yao, Yuan-Yuan; Zhao, Xian-Liang
Letters in Organic Chemistry, 2015 , vol. 12, # 1 p. 73 - 76 Title/Abstract Full Text View citing articles Show Details
Typical Experimental Procedure
General procedure: NaClO2 (0.21g, 85percent, 2.0 mmol) was added to a solutionof oxime 1a (0.27g, 2.0 mmol), concentrated HCl (36percent, 2.0mL) in H2O (2.0 mL) in test tube, and the reaction mixturewas stirred at room temperature for 5 min (monitoring with thin-layer chromatography, TLC). The reaction was extractedwith ethyl acetate (10 mL). The combined organicextract was washed with water (5 mL) and dried with anhydrousMgSO4. Then it was directly filtered through a shortsilica gel column (200–300 mesh) to afford the product 2a(0.22 g, 92percent). The carbonyl compounds formed were characterizedby their physical data, which were in accordancewith values reported in the literature, and GC-MS analysis. 92%
With benzyltriphenylphosphonium dichromate; silica gel
0.0833333 h;
Hajipour; Mallakpour
Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001 , vol. 356, p. 371 - 387 Title/Abstract Full Text View citing articles Show Details
90%
With zeolyte H-Y supported KMnO4 in 1,2-dichloro-ethane
0.5 h; Ambient temperature;
Jadhav; Wadgaonkar; Joshi; Salunkhe
Synthetic Communications, 1999 , vol. 29, # 11 p. 1989 - 1995 Title/Abstract Full Text View citing articles Show Details
90%
With water in acetone
0.0333333 h; microwave irradiation;
Khazaei, Ardeshir; Sadri, Minoo; Hosseini, Hassan
Journal of the Chinese Chemical Society, 2007 , vol. 54, # 4 p. 1011 - 1015 Title/Abstract Full Text View citing articles Show Details
90%
With N-iodo-succinimide; water in acetone
0.05 h; Microwave irradiation;
Manesh, Abbas Amini; Khazaei, Ardeshir
Asian Journal of Chemistry, 2011 , vol. 23, # 2 p. 762 - 764 Title/Abstract Full Text View citing articles Show Details
89%
With sodium perborate in acetic acid
T=90 - 95°C; 8 h;
Bandgar; Shaikh; Iyei, Suresh
Synthetic Communications, 1996 , vol. 26, # 6 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
88%
With ruthenium trichloride; toluene-4-sulfonic acid in N,N-dimethyl acetamide; water
T=120°C; P=760.051 Torr; 8 h; Inert atmosphereGreen chemistry;
Liu, Yuxiao; Yang, Na; Chu, Changhu; Liu, Renhua
Chinese Journal of Chemistry, 2015 , vol. 33, # 9 p. 1011 - 1014 Title/Abstract Full Text View citing articles Show Details
87%
With KMnO4/alumina
T=50°C; 0.25 h;
Imanzadeh; Hajipour; Mallakpour
Synthetic Communications, 2003 , vol. 33, # 5 p. 735 - 740 Title/Abstract Full Text View citing articles Show Details
87%
With chromium trioxide-kieselghur reagent in dichloromethane
2.5 h; Reflux;
Lou, Ji-Dong; Lu, Xiu Lian; Huang, Li-Hong; Zhang, Changhe; Wang, Qiang; Zou, Xiao-Nan
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011 , vol. 41, # 10 p. 1278 - 1281 Title/Abstract Full Text View citing articles Show Details
86%
With water; NBBTA in acetone
0.05 h; Microwave irradiation;
Manesh, Abbas Amini; Khazaei, Ardeshir
Asian Journal of Chemistry, 2011 , vol. 23, # 2 p. 624 - 626 Title/Abstract Full Text View citing articles Show Details
86%
With potassium permanganate supported on kieselguhr reagent in dichloromethane
T=20°C; 0.333333 h; Green chemistry;
Lou, Ji-Dong; Lin, Fang; Huang, Lihong; Zou, Xiao-Nan
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2012 , vol. 42, # 7 p. 1027 - 1029 Title/Abstract Full Text View citing articles Show Details
86%
in dichloromethane
Lin, Fang; Lin, Jianan; Zheng, Wenjin; Lu, Xiu Lian; Lou, Ji-Dong
T=20°C; 4.5 h;
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013 , vol. 43, # 10 p. 1518 - 1520 Title/Abstract Full Text View citing articles Show Details
86%
With manganese(IV) oxide in neat (no solvent) T=20°C; 0.0333333 h;
Zheng, Wenjin; Huang, Chen; Zhang, Changhe; Zhou, Yi-Feng; Lou, Ji-Dong
Research on Chemical Intermediates, 2013 , vol. 39, # 2 p. 499 - 504 Title/Abstract Full Text View citing articles Show Details
85%
With hydrogenchloride in water; acetonitrile
0.0333333 h; microwaver irradiation;
Anniyappan, Marimuthu; Muralidharan; Perumal, Paramasivan T.
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002 , vol. 41, # 11 p. 2419 - 2420 Title/Abstract Full Text View citing articles Show Details
85%
With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen; benzaldehyde in toluene
T=50°C; 8 h;
Zhou, Xian-Tai; Yuan, Qiu-Lan; Ji, Hong-Bing
Tetrahedron Letters, 2010 , vol. 51, # 4 p. 613 - 617 Title/Abstract Full Text View citing articles Show Details
85%
With Jones reagent supported on Kieselguhr in dichloromethane
T=20°C; 1.5 h;
Lou, Ji-Dong; Lin, Fang; Lu, Xiu Lian; Wang, Qiang; Zou, Xiao-Nan
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2012 , vol. 42, # 2 p. 282 - 284 Title/Abstract Full Text View citing articles Show Details
85%
With toluene-4-sulfonic acid
T=20°C; 0.0166667 h; neat (no solvent);
Dewan, Anindita; Utpal Bora; Dilip K. Kakati
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 7 p. 2482 - 2484 Title/Abstract Full Text View citing articles Show Details
82%
With vanadium(III) chloride in tetrahydrofuran
8 h; Ambient temperature;
Olah, George A.; Arvanaghi, Massoud; Prakash, G.K. Surya
Synthesis, 1980 , # 3 p. 220 Title/Abstract Full Text Show Details
82%
With antimonypentachloride in dichloromethane
T=20°C; 2.3 h;
Narsaiah, A. Venkat; Nagaiah
Synthesis, 2003 , # 12 p. 1881 - 1882 Title/Abstract Full Text View citing articles Show Details
82%
With potassium permanganate in neat (no solvent) T=20°C; 0.166667 h; Milling;
Zhu, Li-Yun; Lou, Zhiyuan; Lin, Jianan; Zheng, Wenjin; Zhang, Changhe; Lou, Ji-Dong
Research on Chemical Intermediates, 2013 , vol. 39, # 9 p. 4315 - 4320 Title/Abstract Full Text View citing articles Show Details
81%
With potassium sulfate; potassium hydrogensulfate; oxone; acetic acid in water
T=40 - 45°C; 2 h;
Bose, D. Subhas; Srinivas
Synthetic Communications, 1997 , vol. 27, # 22 p. 3835 - 3838 Title/Abstract Full Text View citing articles Show Details
81%
With hexamethylenetetramine; hydrobromide
T=20°C; Hydrolysis; 0.0333333 h;
Bandgar; Makone
Organic Preparations and Procedures International, 2000 , vol. 32, # 4 p. 391 - 394 Title/Abstract Full Text View citing articles Show Details
79%
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate
T=20°C; 0.00833333 h;
Hajipour; Mallakpour; Mohammadpoor-Baltork; Khoee
Synthetic Communications, 2001 , vol. 31, # 8 p. 1187 - 1194 Title/Abstract Full Text View citing articles Show Details
79%
With oxygen; sodium nitrite in dichloromethane; water
T=25°C; P=760.051 Torr; 7 h; Sealed system;
Zhang, Guofu; Wen, Xin; Wang, Yong; Mo, Weimin; Ding, Chengrong
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4665 - 4668 Title/Abstract Full Text View citing articles Show Details
78%
With TMGFC in dichloromethane
0.00277778 h; Microwave irradiation; Reagent/catalyst; Hide Experimental Procedure
Şendil, Kivilcim; Özgün, H. Beytiye; Üstün, Ebru
Journal of Chemistry, 2016 , vol. 2016, art. no. 3518102 Title/Abstract Full Text View citing articles Show Details
2.4. General Procedure for the Oxidation under Microwave Irradiation
General procedure: The substrate (1mmol) and 1.5–2 mmol oxidant were mixed. To this mixture 0.5 mL CH2Cl2 was added. The mixture was subjected to microwave irradiation (1000 W). Upon completion of the reaction, extraction with ether (3 × 25mL) and evaporation of the solvent gave the corresponding carbonyl compounds. The products formed were analyzed by their 2,4-dinitrophenylhydrazone derivatives.The precipitated 2,4-DNP was filtered off, weighed, and recrystallized from ethanol. 75%
With sodium hydroxide; dihydrogen peroxide in methanol
Heating;
Ho, Tse-Lok
Synthetic Communications, 1980 , vol. 10, # 6 p. 465 - 468 Title/Abstract Full Text Show Details
67%
With N-Bromosuccinimide in water; acetone
T=25°C; 2.5 h;
Bandgar, Babasaheb P.; Kale, Ramesh R.; Kunde, Lalita B.
Monatshefte fur Chemie, 1998 , vol. 129, # 10 p. 1057 - 1060 Title/Abstract Full Text View citing articles Show Details
42%
With ziconium(IV) oxychloride octahydrate in water; acetone
7 h; Reflux;
Saikia, Lakhinath; Das, Subrata; Thakur, Ashim Jyoti
Synthetic Communications, 2011 , vol. 41, # 7 p. 1071 - 1076 Title/Abstract Full Text View citing articles Show Details
41%
With cerium(IV) sulphate in chloroform
T=20°C; 2.33333 h; Hide Experimental Procedure
Asutay, Oktay; Hamarat, Nilüfer; Uludag, Nesimi; Coşkun, Necdet
Tetrahedron Letters, 2015 , vol. 56, # 25 p. 3902 - 3904 Title/Abstract Full Text View citing articles Show Details
oxidative deoximation of oximes
General procedure: To a solution of p-chlorobenzaldoxime (3 mmol, 0.468 g) in chloroform (9 mL),dehydrated Ce(SO4)2 (9 mmol, 2.998 g) was added and the reaction mixturestirred at room temperature for 15 min. The mixture was filtered through asintered glass funnel and the organic solvent evaporated. Besides pchlorobenzaldehyde(19percent), 3,5-bis(4-chlorophenyl)-1,2,4-oxadiazole and 1-chloro-4-(dinitromethyl)benzene were also isolated in 3percent and 7percent yields,respectively after column chromatography.
With bis(trimethylsilyl)chromate in dichloromethane
18 h; Ambient temperatureother oximes, var. time; Product distribution;
Lee; Kwak; Hwang
Synthetic Communications, 1992 , vol. 22, # 16 p. 2425 - 2429 Title/Abstract Full Text View citing articles Show Details
With aluminum oxide; Me3NHCrO3Cl in dichloromethane
T=38°C; 7 h; Yield given;
Zhang, Gui-Sheng; Yang, De-Hong; Chen, Mi-Feng
Organic Preparations and Procedures International, 1998 , vol. 30, # 6 p. 713 - 716 Title/Abstract Full Text View citing articles Show Details
With dimethylammonium chlorochromate; silica gel in diethyl ether; dichloromethane
T=38 - 40°C; 5.5 h;
Zhang, Gui-Sheng; Chai, Bing
Synthetic Communications, 2000 , vol. 30, # 10 p. 1849 - 1855 Title/Abstract Full Text View citing articles Show Details
40 % Chromat.
With chloranil in acetonitrile
8 h; Irradiation;
De Lijser, H. J. Peter; Fardoun, Fadia H.; Sawyer, Jody R.; Quant, Michelle
Organic Letters, 2002 , vol. 4, # 14 p. 2325 - 2328 Title/Abstract Full Text View citing articles Show Details
87 %Chromat.
With MnTEPyP; dihydrogen peroxide in water; acetone
T=60°C; 2.5 h;
Ren, Qing-Gang; Zhou, Xian-Tai; Ji, Hong-Bing
Journal of Porphyrins and Phthalocyanines, 2011 , vol. 15, # 3 p. 211 - 216 Title/Abstract Full Text View citing articles Show Details
With 3,5-dimethylpyrazolium chlorochromate
T=20°C; 0.0166667 h; Neat (no solvent);
Canbulat, Melek; Oezguen, Beytiye
Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2012 , vol. 42, # 5 p. 634 - 637 Title/Abstract Full Text View citing articles Show Details
18
Synthesize Find similar
Synthesize Find similar
Rx-ID: 3778419 Find similar reactions
82%
With lithium perchlorate in water; acetonitrile
T=25°C; electrolysis;
Lin, En-Chu; Mark, Michael R. Van De
Journal of the Chemical Society, Chemical Communications, 1982 , # 20 p. 1176 - 1178 Title/Abstract Full Text View citing articles Show Details
81%
With bismuth (III) oxychloride in water; acetonitrile
1.25 h; Reflux;
Manesh, Abbas Amini; Azarin, Khadijeh
Journal of the Serbian Chemical Society, 2016 , vol. 81, # 2 p. 125 - 131
Hide Experimental Procedure
Title/Abstract Full Text View citing articles Show Details
General procedure for the cleavage of hydrazones by bismuth oxychloride:
General procedure: A solution of the hydrazone (1 mmol) in acetonitrile (10 mL) was refluxed for 10 min.Then BiOCl (1 mmol) was added to the solution and the mixture was refluxed for theappropriate time, as indicated in Table I. After completion of the reaction (TLC monitored),the reaction mixture was cooled to room temperature and H2O (1 mmol) was added and themixture stirred for 10 min. Then the solvent was evaporated and CHCl3 or THF was added.After stirring the mixture for 10 min, the solid residue was filtered off and washed with CHCl3or THF (10 mL). Evaporation of the solvent gave the pure carbonyl products in excellentyields.
19
Synthesize Find similar
72.6%
Rx-ID: 5929728 Find similar reactions
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Nippon Zeon Co., Ltd.
Patent: US5118862 A1, 1992 ; Title/Abstract Full Text Show Details
C.2:Comparative Example 2
Comparative Example 2 Example 1 was repeated except that the catalyst used was prepared in the same manner as in Reference Example 1 except that the reduction with hydrogen gas was not conducted. Yield of 2-cyclopentenone in the reaction mixture was 2.2percent and selectivity was 2.9percent. Principal product was cyclopentanone (yield 72.6percent).
69%
With dipotassium peroxodisulfate; tris(2,2'-bipyridyl)ruthenium dichloride in water; acetonitrile
T=20°C; 12 h; Irradiation; Hide Experimental Procedure
Chung-Ang University Academic Cooperation; Jo, Uhn Jin; Nadim, Iqbal
Patent: KR101609985 B1, 2016 ; Location in patent: Paragraph 0093; 0094; 0095; 0096 ; Title/Abstract Full Text Show Details
Example 16:Examples 3 to 16
General procedure: Photocatalyst (Ru (bpy) 3Cl2) was prepared in the amine-based compound, a 1 molpercentconcentration of the oxidizing agent (K2S2O8) and solvent (0.1 M, CH3CN / H2O (1/1))under the condition, the blue light-emitting diode in the power consumption 7W was a12-hour reaction at room temperature using. With the selected amine compound wasanalyzed and the manufactured product are shown in Table 2 below Yield of the product was measured by gas chromatography using a dodecane (dodecane)as an internal standard method
57%
JX Nippon Oil and Energy Corporation
Patent: EP2364965 A1, 2011 ; Location in patent: Page/Page column 12-13 ; Title/Abstract Full Text Show Details
Hide Details
57%
JX NIPPON OIL and ENERGY CORPORATION
Patent: US2011/288340 A1, 2011 ; Location in patent: Page/Page column 8 ; Title/Abstract Full Text Show Details
Herstellung von <1-14C>Cyclopentanon;
Brooks
Journal of the Chemical Society, 1958 , p. 3693,3695 Full Text View citing articles Show Details
Herstellung von <1,2-14C2>Cyclopentanon;
Loftfield
Org. Synth. Isotopes, 1958 , p. 654 Full Text Show Details
Wiloth,F.; Schindler,E.
Chemische Berichte, 1967 , vol. 100, p. 2373 - 2376
Full Text View citing articles Show Details
Bestmann,H.J.; Kranz,E.
Chemische Berichte, 1969 , vol. 102, p. 1802 - 1815 Full Text View citing articles Show Details
Mihailovic,M.L. et al.
Tetrahedron, 1968 , vol. 24, p. 4947 - 4961 Full Text View citing articles Show Details
Omura,K.; Swern,D.
Tetrahedron, 1978 , vol. 34, p. 1651 - 1660 Full Text View citing articles Show Details
Singh,R.P. et al.
Tetrahedron, 1979 , vol. 35, p. 1789 - 1793 Full Text View citing articles Show Details
Rabiller,C. et al.
Bulletin de la Societe Chimique de France, 1974 , p. 3055 - 3058 Full Text View citing articles Show Details
Yamamoto,Y.; Brown,H.C.
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Greene,F.D. et al.
Journal of Organic Chemistry, 1963 , vol. 28, p. 55 - 64 Full Text View citing articles Show Details
Hermes,M.E.; Marsh,F.D.
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Tetrahedron Letters, 1974 , p. 3329 - 3332 Full Text View citing articles Show Details
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Ogibin; Troyanskii; Nikishin
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1977 , vol. 26, # 4 p. 767 - 771 Title/Abstract Full Text View citing articles Show Details
Delmond, Bernard; Pommier, Jean-Claude; Valade, Jacques
Journal of Organometallic Chemistry, 1972 , vol. 35, # 1 p. 91 - 104 Title/Abstract Full Text View citing articles Show Details
Foerster,C. et al.
Journal fuer Praktische Chemie (Leipzig), 1969 , vol. 311, p. 370 - 378 Full Text View citing articles Show Details
House; Babad
Journal of Organic Chemistry, 1963 , vol. 28, p. 90 Full Text View citing articles Show Details
Marsh; Hermes
Journal of the American Chemical Society, 1964 , vol. 86, p. 4506 Full Text View citing articles Show Details
Jaz; Davreux
Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 370 Full Text View citing articles Show Details
Flatt et al.
Synthesis, 1979 , p. 815 Full Text View citing articles Show Details
Bestmann; Kranz
Angewandte Chemie, 1967 , vol. 79, p. 95 Full Text Show Details
Nelson et al.
Journal of the Chemical Society [Section] D: Chemical Communications, 1971 , p. 1580 Full Text View citing articles Show Details
Huet et al.
Synthesis, 1978 , p. 63 Full Text Show Details
Giannotti
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964 , vol. 258, p. 5225 Full Text Show Details
Holum
Journal of Organic Chemistry, 1961 , vol. 26, p. 4814,4815 Full Text Show Details
Pratt; van de Castle
Journal of Organic Chemistry, 1961 , vol. 26, p. 2973 Full Text View citing articles Show Details
Maloney; Lyle; Saavedra
Synthesis, 1978 , vol. No. 3, p. 212 - 213 Title/Abstract Full Text View citing articles Show Details
Cella et al.
Journal of Organic Chemistry, 1975 , vol. 40, p. 1860 Full Text View citing articles Show Details
Kuehne; Hall
Journal of Organic Chemistry, 1976 , vol. 41, p. 2742 Full Text View citing articles Show Details
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Azerbaidzhanskii Khimicheskii Zhurnal, 1969 , vol. 6, p. 86,88 Chem.Abstr., 1971 , vol. 74, # 53112 Full Text Show Details
Huang et al.
Synthesis, 1978 , p. 297 Full Text Show Details
Franzen; Otto
Chemische Berichte, 1961 , vol. 94, p. 1360,1363 Full Text Show Details
Heyns; Blazejewicz
Tetrahedron, 1960 , vol. 9, p. 67,73 Full Text Show Details
Allen et al.
Journal of the Chemical Society, 1960 , p. 1909,1911 Full Text Show Details
Maynez et al.
Journal of Organic Chemistry, 1975 , vol. 40, p. 3302 Full Text View citing articles Show Details
Olah; Ho
Synthesis, 1976 , p. 610 Full Text Show Details
Turowa-Poljak et al.
Neftekhimiya, 1964 , vol. 4, p. 603 engl. Ausg., p. 240 Full Text Show Details
Boldrini et al.
Synthesis, 1976 , p. 596 Full Text Show Details
Hintz; Johnson
Journal of Organic Chemistry, 1967 , vol. 32, p. 556,558 Full Text Show Details
Sacks; Fuchs
Synthesis, 1976 , p. 456 Full Text Show Details
Boontanonda; Grigg
Journal of the Chemical Society, Chemical Communications, 1977 , p. 583 Full Text View citing articles Show Details
Jung et al.
Tetrahedron Letters, 1977 , p. 4175,4177 Full Text Show Details
Townsend; Spencer
Tetrahedron Letters, 1971 , p. 137,138 Full Text Show Details
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Tetrahedron Letters, 1971 , p. 105,106 Full Text Show Details
Cella et al.
Tetrahedron Letters, 1975 , p. 4115 Full Text View citing articles Show Details
Tufariello; Kissel
Tetrahedron Letters, 1966 , p. 6145,6147 Full Text Show Details
Liu; Lai
Tetrahedron Letters, 1979 , p. 1193,1195 Full Text Show Details
Abley et al.
Journal of the American Chemical Society, 1976 , vol. 32, p. 2591,2592-2594 Full Text Show Details
Greene et al.
Tetrahedron Letters, 1976 , p. 2707 Full Text View citing articles Show Details
Deutsche Advance Prod.
Patent: BE615018DE , 1962 ; Chem.Abstr., 1962 , vol. 57, # 14941 Full Text Show Details
Fujihara et al.
Yukagaku, 1975 , vol. 24, p. 654,657 Chem.Abstr., vol. 84, # 59755n Full Text Show Details
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Synthesis, 1979 , p. 274 Full Text Show Details
Blackburn; Schwartz
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Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1971 , vol. 20, p. 1809,1811 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971 , vol. 20, p. 1917 Full Text Show Details
Collman
Accounts of Chemical Research, 1975 , vol. 8, p. 342,343, 344 Full Text View citing articles Show Details
Cortese; Heck
Journal of Organic Chemistry, 1978 , vol. 43, p. 3985,3987 Full Text Show Details
Sheikh; Eadon
Tetrahedron Letters, 1972 , p. 257,258,259 Full Text View citing articles Show Details
Leriverend; Leriverend
Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1975 , vol. 280, p. 791 Full Text Show Details
Price; Iwasa
Bulletin of the Chemical Society of Japan, 1976 , vol. 49, p. 214,215, 216 Full Text Show Details
Olah et al.
Synthesis, 1979 , p. 113 Full Text Show Details
Schroeder; Griffith
Journal of the Chemical Society, Chemical Communications, 1979 , p. 58 Full Text Show Details
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Bulletin of the Chemical Society of Japan, 1964 , vol. 37, p. 1704 Full Text Show Details
Minatschew et al.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1964 , p. 10 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964 , p. 13 Full Text Show Details
Jaworski; Kwiatkowski
Roczniki Chemii, 1974 , vol. 48, p. 263,268 Full Text Show Details
Liberman et al.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1971 , vol. 20, p. 1423,1427 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971 , vol. 20, p. 1527 Full Text Show Details
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Chemical Communications (London), 1966 , p. 744 Full Text View citing articles Show Details
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Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1972 , vol. 21, p. 1942 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1972 , vol. 21, p. 2001 Full Text View citing articles Show Details
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Journal of the American Chemical Society, 1978 , vol. 100, p. 6425 Full Text View citing articles Show Details
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Bulletin of the Chemical Society of Japan, 1969 , vol. 42, p. 2917,2918 Full Text Show Details
Hofmann
Angewandte Chemie, 1965 , vol. 77, p. 346 Full Text Show Details
Liberman; Vasina
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1968 , p. 609,610,611 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1968 , p. 632 Full Text Show Details
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J. Gen. Chem. USSR (Engl. Transl.), 1960 , vol. 30, p. 359,383 Chem.Abstr., 1960 , vol. 54, # 24457 Full Text Show Details
Ho
Synthetic Communications, 1979 , vol. 9, p. 237 Full Text Show Details
Rajan et al.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1979 , vol. 17, p. 80 Full Text Show Details
Tsuji; Ohno
Journal of the American Chemical Society, 1968 , vol. 90, p. 94 Full Text View citing articles Show Details
Moon; Waxman
Journal of Organic Chemistry, 1969 , vol. 34, p. 1157 Full Text View citing articles Show Details
Crouzet et al.
Bulletin de la Societe Chimique de France, 1967 , p. 4047 Full Text Show Details
Delmond; Pommier
Tetrahedron Letters, 1968 , p. 6147 Full Text View citing articles Show Details
Bird; Diaper
Canadian Journal of Chemistry, 1969 , vol. 47, p. 145 Full Text Show Details
Corey; Achiwa
Journal of the American Chemical Society, 1969 , vol. 91, p. 1429 Full Text View citing articles Show Details
Brown; Ritchie
Journal of the Chemical Society [Section] C: Organic, 1968 , p. 2007 Full Text View citing articles Show Details
Pearson; Moss
Tetrahedron Letters, 1967 , p. 3791 Full Text View citing articles Show Details
Brown; Hess
Journal of Organic Chemistry, 1969 , vol. 34, p. 2206 Full Text View citing articles Show Details
Richer; Nguyen Thi Thanh Hoa
Canadian Journal of Chemistry, 1969 , vol. 47, p. 2479 Full Text Show Details
Wahlroos; Enkvist
Acta Chemica Scandinavica (1947-1973), 1968 , vol. 22, p. 3202,3206 Full Text Show Details
Schwall et al.
Chemische Berichte, 1969 , vol. 102, p. 1731 Full Text Show Details
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Blakemore, David Clive; Bryans, Justin Stephen
Patent: US2003/187296 A1, 2003 ; Title/Abstract Full Text Show Details
7:The Cyclopentanone 20
The Cyclopentanone 20 Methylmagnesium chloride (22.5 ml of a 3M solution in ether, 67.5 mmol) was added slowly to a stirred solution of dimethylzinc (16.9 ml of a 2M solution in toluene, 33.8 mmol) in THF (100 ml) under argon at 0° C. After 30 minutes the mixture was cooled to -78 ° C. and 19 (3.37 g, 30.6 mmol) in THF (45 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 20 minutes and then quenched by the addition of saturated ammonium chloride solution (25 ml). The reaction mixture was allowed to warm to room temperature, diluted with 1N hydrochloric acid (100 ml) and extracted with ether (3*100 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and the solvent was removed under reduced pressure to yield 20 as a solution in toluene which was purified by column chromatography (SiO2, pentane-ether, 95:5) to give the cyclopentanone 20 (2.4 g, 62percent). δH(400 MHz; CDCl3) 2.50-2.40 (2H, m), 1.92-1.60 (6H, m), 1.12 (3H, d, J 6.1, Me), 0.93 (3H, t, J 6.5, Me).
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Rhone-Poulenc Chimie
Patent: US4983767 A1, 1991 ; Title/Abstract Full Text Show Details
Exemplary of such ketones, the following are representative: Cyclopentanone; 2-Methylcyclohexanone; 2-Methylcyclopentanone; 2,5-Dimethylcyclopentanone; 2,6-Dimethylcyclohexanone; and 2-Phenylcyclohexanone.
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Standard Oil Company
Patent: US4271091 A1, 1981 ; Title/Abstract Full Text Show Details
Suitable charge stock compounds include the following without being limited, thereto, cyclohexanol, cyclohexanone, cyclohexanol, cyclohexanone, ... 1,4-cyclohexanedione, 4-methylcyclohexanone, 3,5-dimethylcyclohexanone, 4-phenylcyclohexanone, cyclopentanone, 3-methylcyclopentanol, 2-ketotetralin, 2-(1-cyclohexenyl)cyclohexanone,
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methyl ethyl ketone ... amyl acetate neopentyl acetate propyl propionate t-butyl propionate cyclopentanone
Eli Lilly and Company
Patent: US4303591 A1, 1981 ; Title/Abstract Full Text Show Details
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The Standard Oil Co.
Patent: US4379925 A1, 1983 ; Title/Abstract Full Text Show Details
Suitable charge stock compounds include the following without being limited, thereto, cyclohexanol, cyclohexanone, cyclohexanol, cyclohexanone, ... 4-methylcyclohexanone, 3,5-dimethylcyclohexanone, 4-phenylcyclohexanone, cyclopentanol, cyclopentanone, 3-methylcyclopentanol, 2-(1-cyclohexenyl)cyclohexanone,
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Eli Lilly and Company
Patent: US4501608 A1, 1985 ; Title/Abstract Full Text Show Details
Representative aldehydes and ketones include: formaldehyde ... methyl propyl ketone methyl butyl ketone methyl isobutyl ketone methyl tert-butyl ketone cyclopentanone cyclooctanone
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Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
57:EXAMPLE 57
EXAMPLE 57 Experiment was carried out in the same manner as in Example 54 except that the reaction temperature was raised from 50° C. up to 80° C., to obtain 3.2 g of cyclopentanone at a reaction time of 15 minutes.
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Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
58:EXAMPLE 58
EXAMPLE 58 Experiment was carried out in the same manner as in Example 54 except that the concentration of Cu(1)Cl was raised from 0.2 M up to 0.5 M, to obtain 3.0 g of cyclopentanone at a reaction time of 20 minutes.
Hide Experimental Procedure
Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
60:EXAMPLE 60
EXAMPLE 60 Experiment was carried out in the same manner as in Example 55 except that Cu(1)Cl (0.2 M) was replaced by Ti(3)CH3 (0.2 M) to obtain 0.61 g of cyclopentanone in 30 minutes.
Hide Experimental Procedure
61:EXAMPLE 61
EXAMPLE 61
Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
Experiment was carried out in the same manner as in Example 55 except that Cu(1)Cl (0.2 M) was replaced by V(3)Cl3 (0.2 M) to obtain 0.72 g of cyclopentanone in 30 minutes.
Hide Experimental Procedure
Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
62:EXAMPLE 62
EXAMPLE 62 Experiment was carried out in the same manner as in Example 54 except that CH3 CN was replaced by PhCN to obtain 0.95 g of cyclopentanone at a reaction time of one hour.
Hide Experimental Procedure
Babcock-Hitachi Kabushiki Kaisha
Patent: US4806692 A1, 1989 ; Title/Abstract Full Text Show Details
63:EXAMPLE 63
EXAMPLE 63 Experiment was carried out in the same manner as in Example 62 except that the concentration of Cu(1)Cl was raised from 0.2 M up to 0.6 M to obtain 1.2 g of cyclopentanone in 30 minutes.
Hide Experimental Procedure
American Cyanamid Company
Patent: US4061672 A1, 1977 ; Title/Abstract Full Text Show Details
8:Preparation of 2-carboxyhexyl)cyclopentan-1-one
EXAMPLE 8 Preparation of 2-carboxyhexyl)cyclopentan-1-one In the manner described in Example 2, ethyl and methyl 2-(6-carbethoxyhexyl)-1-cyclopentanone-2-carboxylate (Example 7) is hydrolyzed to furnish the subject product, b.p. 143° C. (0.05 mm).
Hide Experimental Procedure
American Cyanamid Company
Patent: US4110368 A1, 1978 ; Title/Abstract Full Text Show Details
6:Preparation of 2-(3-carbethoxyropyl)cyclopentan-1-one
EXAMPLE 6 Preparation of 2-(3-carbethoxyropyl)cyclopentan-1-one In the manner described in Example 3, treatment of 2-(3-carboxypropyl)cyclopentan-1-one (Example 5) with p-toluene-sulfonic acid monohydrate in ethanol gives a colorless oil, b.p. 93° C. (0.10 mm).
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BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ; Title/Abstract Full Text Show Details
57:Example 57
Example 57 Experiment was carried out in the same manner as in Example 54 except that the reaction temperature was raised from 50°C up to 80°C, to obtain 3.2 g of cyclopentanone at a reaction time of 15 minutes.
Hide Experimental Procedure
BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ; Title/Abstract Full Text Show Details
58:Example 58
Example 58 Experiment was carried out in the same manner as in Example 54 except that the concentration of Cu(1)C was raised from 0.2 M up to 0.5 M, to obtain 3.0 g of cyclopentanone at a reaction time of 20 minutes.
Hide Experimental Procedure
BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ; Title/Abstract Full Text Show Details
60:Example 60
Example 60 Experiment was carried out in the same manner as in Example 55 except that Cu(1)C (0.2 M) was replaced by Ti(3)C3 (0.2 M) to obtain 0.61 g of cyclopentanone in 30 minutes.
BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
61:Example 61
Example 61 Experiment was carried out in the same manner as in Example 55 except that Cu(1)C (0.2 M) was replaced by V(3)C3 (0.2 M) to obtain 0.72 g of cyclopentanone in 30 minutes.
BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
62:Example 62
Example 62 Experiment was carried out in the same manner as in Example 54 except that CH3CN was replaced by PhCN to obtain 0.95 g of cyclopentanone at a reaction time of one hour.
BABCOCK-HITACHI KABUSHIKI KAISHA
Patent: EP189312 B1, 1991 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
63:Example 63
Example 63 Experiment was carried out in the same manner as in Example 62 except that the concentration of Cu(1)C was raised from 0.2 M up to 0.6 M to obtain 1.2 g of cyclopentanone in 30 minutes.
Taber, Douglass F.; Farach-Carson, Mary C.; Malcolm, Scott C.; Xu, Yihuan
Patent: US2004/242677 A1, 2004 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
1:Synthesis of Astrogorgiadiol
This substance was not stable to analysis by mass spectrometry. Methyl 5-Dimethylhexenyl-2-oxocyclopentanecarboxylate (2) via Rh2Oct4 Catalysis: The CH2Cl2 used in the following reaction was distilled from CaH2 and passed through a column (20*150 mm) of anhydrous K2CO3 prior to use. The α-diazo-β-ketoester 1 (25.5 g, 101 mmol) was dissolved in 1 L CH2Cl2. A solution of rhodium octanoate (400 mg, 0.56 mol percent) in 5 mL dry CH2Cl2 was added in one portion. The solution was allowed to stir for 12 hours before being evaporated. The green residue was chromatographed to provide cyclopentanone 2 (17.0 g, 74percent) as a light-green oil. Bulb-to-bulb distillation (170° C. at 0.4 mm Hg) yielded a clear oil which formed moist crystals on standing. These did not show a sharp melting point. TLC Rf(10percent MTBE/petroleum ether)=0.28. 1H NMR (CDCl3) (δ): 5.06 (m, 1H), 3.75 (s, 3H), 2.97 (d, J=11.6 Hz, 0.43H), 2.95 (d, J=11.3 Hz, 0.57H), 2.55 (m, 1H), 2.5-2.3 (m, 2H), 2.3-1.9 (m, 3H), 1.69 (s, 3H), 1.61 (s, 3H), 1.6-1.3 (m, 3H), 1.17 (m, 1h), 0.93 (d, J=6.83 Hz, 1.3H), 0.91 (d, J=6.85 Hz, 1.7H); 13C NMR (CDCl3) (δ): (Major) u: 212.4, 170.7, 131.7, 38.7, 33.8, 25.3, 25.1; d: 124.2, 59.6, 52.4, 46.7, 36.8, 25.7, 17.6, 16.9; 13C NMR (CDCl3) (δ): (Minor) u: 212.2, 170.3, 131.6, 38.5, 33.8, 25.3, 25.1; d: 124.1, 59.7, 52.4, 46.3, 35.7, 25.7, 15.5, 16.9; IR (cm-1): 3447 (br), 2966, 1757, 1726. A
B
C
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20
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1:
With 1-hydroxy-pyrrolidine-2,5-dione; oxygen in water
T=25 - 150°C; P=22502.3 Torr; autoclave; Product distribution / selectivity; Hide Experimental Procedure
DAICEL CHEMICAL INDUSTRIES, LTD.
Patent: EP2096097 A1, 2009 ; Location in patent: Page/Page column 12; 14 ; Title/Abstract Full Text Show Details
In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 80 g (1.14 mol) of cyclopentane and 2 g of a 5 percent by weight N-hydroxysuccinimide aqueous solution which contained 100 mg of N-hydroxysuccinimide dissolved therein, at room temperature (25°C). The autoclave was hermetically sealed, pressurized to 3 MPa (gauge pressure) with a gaseous mixture of 50 percent by volume oxygen and 50 percent by volume nitrogen, and the aqueous solution therein was stirred at 150°C for 1 hour. As a result, 39 mmol of cyclopentane reacted (with a conversion of 3.4percent) and thereby yielded 9.4 mmol of cyclopentanone (with a selectivity of 24.1percent), 4.8 mmol of cyclopentanol (with a selectivity of 12.3percent), and 12.5 mmol of cyclopentyl hydroperoxide (with a selectivity of 32.1percent). The total yield of cyclopentanone, cyclopentanol, and cyclopentyl hydroperoxide was 2.3percent.
A: 32 %Chromat. B: 28 %Chromat. C: 7 %Chromat.
Stage #1: With [CuI(tris(2-pyridylmethyl)amine)(CH3CN)](PF6); dihydrogen peroxide in water; acetonitrile
T=20°C; 6 h; Stage #2: With triphenylphosphine
0.333333 h; Cooling with ice; Reagent/catalyst;
Garcia-Bosch, Isaac; Siegler, Maxime A.
Angewandte Chemie - International Edition, 2016 , vol. 55, # 41 p. 12873 - 12876 Angew. Chem., 2016 , vol. 128, # 41 p. 13065 - 13068,4 Title/Abstract Full Text View citing articles Show Details
A
B
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21
Synthesize Find similar Rx-ID: 36338213 Find similar reactions
With water; hydrogen
T=160°C; P=30003 Torr; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With palladium on activated charcoal; hydrogen in water
T=159.84°C; P=37503.8 Torr; 1 h; Reagent/catalyst;
Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao
Green Chemistry, 2016 , vol. 18, # 12 p. 3607 - 3613 Title/Abstract Full Text View citing articles Show Details
A
B
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A: 31% B: 69%
With hydrogen in water
T=160°C; P=30003 Torr; 1.2 h; Autoclave;
Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong
Green Chemistry, 2016 , vol. 18, # 7 p. 2155 - 2164 Title/Abstract Full Text View citing articles Show Details
With water; hydrogen
T=160°C;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 160 °C / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Hide Details
With hydrogen in water
T=149.84°C; P=30003 Torr; 6 h; Autoclave; Reagent/catalyst; chemoselective reaction;
Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao
Green Chemistry, 2015 , vol. 17, # 2 p. 1038 - 1046 Title/Abstract Full Text View citing articles Show Details
With hydrogen in water
T=169.84°C; P=15001.5 Torr; 1 h; Autoclave; Reagent/catalystTemperature; chemoselective reaction;
Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao
Green Chemistry, 2015 , vol. 17, # 2 p. 1038 - 1046 Title/Abstract Full Text View citing articles Show Details
A
B
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23
Synthesize Find similar Rx-ID: 36338235 Find similar reactions
A: 66.1% B: 9.4%
With water; zinc
T=250°C; 2.33333 h; Autoclave;
Ren, Dezhang; Song, Zhiyuan; Li, Lu; Liu, Yunjie; Jin, Fangming; Huo, Zhibao
Green Chemistry, 2016 , vol. 18, # 10 p. 3075 - 3081 Title/Abstract Full Text View citing articles Show Details
With water; hydrogen
T=160°C; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
A
B
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24
Synthesize Find similar Rx-ID: 36338236 Find similar reactions
With pentanal; water; hydrogen
T=160°C; P=30003 Torr; 4 h; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With water; hydrogen; benzaldehyde
T=160°C; P=30003 Torr; 4 h; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogen; water / 8 h / 160 °C / |Inert atmosphere; |Autoclave 2: hydrogen; water / 160 °C / 30003 Torr / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Hide Details
With platinum on carbon; hydrogen in water
T=175°C; P=60006 Torr; 0.5 h; Hide Experimental Procedure
Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej
Applied Catalysis A: General, 2013 , vol. 468, p. 426 - 431 Title/Abstract Full Text View citing articles Show Details
General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds.
Multi-step reaction with 2 steps 1: water / 239.84 °C / |Autoclave; |Inert atmosphere 2: hydrogen; palladium on activated charcoal / water / 1 h / 159.84 °C / 37503.8 Torr View Scheme
Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao
Green Chemistry, 2016 , vol. 18, # 12 p. 3607 - 3613 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: MgAl-HT catalyst / water / 0.03 h / 229.84 °C / |Autoclave; |Inert atmosphere; |Green chemistry 2: hydrogen; palladium on activated charcoal / water / 1 h / 159.84 °C / 37503.8 Torr View Scheme
Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao
Green Chemistry, 2016 , vol. 18, # 12 p. 3607 - 3613 Title/Abstract Full Text View citing articles Show Details
A
B
C
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25
Synthesize Find similar Rx-ID: 36689291 Find similar reactions
C: 79%
With hydrogen in water
T=160°C; P=30003 Torr; 2.5 h; Autoclave; Reagent/catalyst;
Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei
Green Chemistry, 2015 , vol. 17, # 8 p. 4183 - 4188 Title/Abstract Full Text View citing articles Show Details
A: 9.7 mol
With hydrogen in water
T=175°C; P=60006 Torr; 0.5 h; Hide Experimental Procedure
Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej
Applied Catalysis A: General, 2013 , vol. 468, p. 426 - 431 Title/Abstract Full Text View citing articles Show Details
General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds.
With 20 Ni/Co3O4; hydrogen in water
T=149.84°C; P=30003 Torr; 6 h; Autoclave; Reagent/catalyst; chemoselective reaction;
Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao
Green Chemistry, 2015 , vol. 17, # 2 p. 1038 - 1046 Title/Abstract Full Text View citing articles Show Details
Hide Details
With hydrogen in water
T=140°C; P=30003 Torr; 4 h; Autoclave;
Yang, Yanliang; Ma, Jiping; Jia, Xiuquan; Du, Zhongtian; Duan, Ying; Xu, Jie
RSC Advances, 2016 , vol. 6, # 56 p. 51221 - 51228 Title/Abstract Full Text View citing articles Show Details
A
B
C
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A: 11% C: 59%
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With Au/ZrO2; hydrogen in water
T=160°C; P=30003 Torr; 1.2 h; Autoclave; Reagent/catalystTime;
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Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong
Green Chemistry, 2016 , vol. 18, # 7 p. 2155 - 2164 Title/Abstract Full Text View citing articles Show Details
A
B
C
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27
Synthesize Find similar Rx-ID: 42219298 Find similar reactions
A: 11% B: 42% C: 41%
With Au on mesoporous silica nanoparticles; hydrogen in water
T=160°C; P=30003 Torr; 1.2 h; Autoclave;
Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong
Green Chemistry, 2016 , vol. 18, # 7 p. 2155 - 2164 Title/Abstract Full Text View citing articles Show Details
28
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97 %Spectr.
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With dimethylsulfoxide-d6; MoO2Cl2(dimethylsulfoxide)2
T=130°C; 0.666667 h; Sealed tubeMicrowave irradiationMolecular sieveGreen chemistry; chemoselective reaction; A
Rx-ID: 42526322 Find similar reactions
García, Nuria; Rubio-Presa, Rubén; García-García, Patricia; Fernández-Rodríguez, Manuel A.; Pedrosa, María R.; Arnáiz, Francisco J.; Sanz, Roberto
Green Chemistry, 2016 , vol. 18, # 8 p. 2335 - 2340 Title/Abstract Full Text View citing articles Show Details
B
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D
E
29
Synthesize Find similar Rx-ID: 43840628 Find similar reactions
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With hydrogen in water
T=159.84°C; P=11251.1 Torr; 5.5 h; Hide Experimental Procedure
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Jackson, Michael A.; Blackburn, Judith A.; Price, Neil P.J.; Vermillion, Karl E.; Peterson, Steven C.; Ferrence, Gregory M.
Carbohydrate Research, 2016 , vol. 432, p. 9 - 16 Title/Abstract Full Text View citing articles Show Details
Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane from xylose
Reactions were performed in a Parr Instruments (Parr Instruments,Moline, IL, USA) stirred reactor with a 300 ml glass liner.Typically, xylose and catalyst were loaded into the reactor with50 ml water, the systemwas charged with hydrogen and evacuatedfive times before being brought up to 15 bar hydrogen. The reactorwas then heated to 433 K and pressurized to the final hydrogenpressure and the reactor was stirred at 250 rpm until the reactionwas complete. Progress of the reaction was monitored by withdrawingsamples via a sampling tube and analyzing by HPLC forunreacted xylose. Upon completion of the reaction, typically after5 h, the catalyst was removed by filtration. The filtrate wasextracted with diethyl ether to remove HPO, CPO, and some of theTHFA. The aqueous portionwas then reduced in volume at reducedpressure to give a heavy residue. This residue was then extractedwith 90:10 hexane:ethyl acetate. Removal of this solvent mix atreduced pressure gave solid 1. 13C NMR (D2O, 125 MHz) d22.8, 33.1 64.6, 68.4,103.1. 1H NMR (D2O, 500 MHz): d1.74 (complex multiplet,2H), 1.84 (complex multiplet, 2H), 1.9 (complex multiplet, 2H), 1.97(complex multiplet, 2H), 3.48 (d, J 12.5, 2H), 3.95 (t, J 7, 2H, 4.05(d, J 12.5, 2H)). EIMS m/z, (relative intensity) 84, (100); 42 (21); 56(16); 43 (11).Isolation of the ringeclosed monomer (2) was accomplishedusing flash chromatography (CombiFlash Rf 200i, Teledyne Isco,Lincoln, NE, USA). Separations were performed using two stackedRedi-Sep Gold Silica columns (12 g each). The mobile phase was ahexane/ethyl acetate gradient flowing at 25 ml/min. The gradientused was a 1e10 column volume (CV) gradient to 10percent EtOAC, holdat 10percent EtOAc for 30 CV, then up to 100percent EtOAc in 10 CV, hold for10 CV, then 0percent EtOAc for 5 CV. Detectionwas accomplished using anelectrospray detector held at 313 K.2-hydroxy-2-hydroxymethyltetrahydrofuran, 2. 13C NMR(acetone-d6, 125 MHz): d 23.2, 33.6, 64.7, 67.1, 102.4. 1H NMR(acetone-d6, 500 MHz): d1.61 (complex multiplet, 2H), 1.78 (complexmultiplet, 2H), 1.85 (complex multiplet, 2H), 1.97 (complexmultiplet, 2H), 2.77 (t, J 0.8, 1H), 2.81 (s, 1H), 3.36 (d, J H), 3.88(m, J 6.0, 2H), 4.01(d, J 11.5, 2H). EIMS m/z, (relative intensity)101, (100); 59, (88); 43, (28); 41, (28). A
B
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30
Synthesize Find similar Rx-ID: 43840629 Find similar reactions
With hydrogen in water
T=159.84°C; P=11251.1 Torr; 5.5 h; Hide Experimental Procedure
Jackson, Michael A.; Blackburn, Judith A.; Price, Neil P.J.; Vermillion, Karl E.; Peterson, Steven C.; Ferrence, Gregory M.
Carbohydrate Research, 2016 , vol. 432, p. 9 - 16 Title/Abstract Full Text View citing articles Show Details
Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane from xylose
Reactions were performed in a Parr Instruments (Parr Instruments,Moline, IL, USA) stirred reactor with a 300 ml glass liner.Typically, xylose and catalyst were loaded into the reactor with50 ml water, the systemwas charged with hydrogen and evacuatedfive times before being brought up to 15 bar hydrogen. The reactorwas then heated to 433 K and pressurized to the final hydrogenpressure and the reactor was stirred at 250 rpm until the reactionwas complete. Progress of the reaction was monitored by withdrawingsamples via a sampling tube and analyzing by HPLC forunreacted xylose. Upon completion of the reaction, typically after5 h, the catalyst was removed by filtration. The filtrate wasextracted with diethyl ether to remove HPO, CPO, and some of theTHFA. The aqueous portionwas then reduced in volume at reducedpressure to give a heavy residue. This residue was then extractedwith 90:10 hexane:ethyl acetate. Removal of this solvent mix atreduced pressure gave solid 1. 13C NMR (D2O, 125 MHz) d22.8, 33.1 64.6, 68.4,103.1. 1H NMR (D2O, 500 MHz): d1.74 (complex multiplet,2H), 1.84 (complex multiplet, 2H), 1.9 (complex multiplet, 2H), 1.97(complex multiplet, 2H), 3.48 (d, J 12.5, 2H), 3.95 (t, J 7, 2H, 4.05(d, J 12.5, 2H)). EIMS m/z, (relative intensity) 84, (100); 42 (21); 56(16); 43 (11).Isolation of the ringeclosed monomer (2) was accomplishedusing flash chromatography (CombiFlash Rf 200i, Teledyne Isco,Lincoln, NE, USA). Separations were performed using two stackedRedi-Sep Gold Silica columns (12 g each). The mobile phase was ahexane/ethyl acetate gradient flowing at 25 ml/min. The gradientused was a 1e10 column volume (CV) gradient to 10percent EtOAC, holdat 10percent EtOAc for 30 CV, then up to 100percent EtOAc in 10 CV, hold for10 CV, then 0percent EtOAc for 5 CV. Detectionwas accomplished using anelectrospray detector held at 313 K.2-hydroxy-2-hydroxymethyltetrahydrofuran, 2. 13C NMR(acetone-d6, 125 MHz): d 23.2, 33.6, 64.7, 67.1, 102.4. 1H NMR(acetone-d6, 500 MHz): d1.61 (complex multiplet, 2H), 1.78 (complexmultiplet, 2H), 1.85 (complex multiplet, 2H), 1.97 (complexmultiplet, 2H), 2.77 (t, J 0.8, 1H), 2.81 (s, 1H), 3.36 (d, J H), 3.88(m, J 6.0, 2H), 4.01(d, J 11.5, 2H). EIMS m/z, (relative intensity)101, (100); 59, (88); 43, (28); 41, (28). A
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With hydrogen in water
T=159.84°C; P=11251.1 Torr; 5.5 h; Hide Experimental Procedure
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Jackson, Michael A.; Blackburn, Judith A.; Price, Neil P.J.; Vermillion, Karl E.; Peterson, Steven C.; Ferrence, Gregory M.
Carbohydrate Research, 2016 , vol. 432, p. 9 - 16 Title/Abstract Full Text View citing articles Show Details
Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane from xylose
Reactions were performed in a Parr Instruments (Parr Instruments,Moline, IL, USA) stirred reactor with a 300 ml glass liner.Typically, xylose and catalyst were loaded into the reactor with50 ml water, the systemwas charged with hydrogen and evacuatedfive times before being brought up to 15 bar hydrogen. The reactorwas then heated to 433 K and pressurized to the final hydrogenpressure and the reactor was stirred at 250 rpm until the reactionwas complete. Progress of the reaction was monitored by withdrawingsamples via a sampling tube and analyzing by HPLC forunreacted xylose. Upon completion of the reaction, typically after5 h, the catalyst was removed by filtration. The filtrate wasextracted with diethyl ether to remove HPO, CPO, and some of theTHFA. The aqueous portionwas then reduced in volume at reducedpressure to give a heavy residue. This residue was then extractedwith 90:10 hexane:ethyl acetate. Removal of this solvent mix atreduced pressure gave solid 1. 13C NMR (D2O, 125 MHz) d22.8, 33.1 64.6, 68.4,103.1. 1H NMR (D2O, 500 MHz): d1.74 (complex multiplet,2H), 1.84 (complex multiplet, 2H), 1.9 (complex multiplet, 2H), 1.97(complex multiplet, 2H), 3.48 (d, J 12.5, 2H), 3.95 (t, J 7, 2H, 4.05(d, J 12.5, 2H)). EIMS m/z, (relative intensity) 84, (100); 42 (21); 56(16); 43 (11).Isolation of the ringeclosed monomer (2) was accomplishedusing flash chromatography (CombiFlash Rf 200i, Teledyne Isco,Lincoln, NE, USA). Separations were performed using two stackedRedi-Sep Gold Silica columns (12 g each). The mobile phase was ahexane/ethyl acetate gradient flowing at 25 ml/min. The gradientused was a 1e10 column volume (CV) gradient to 10percent EtOAC, holdat 10percent EtOAc for 30 CV, then up to 100percent EtOAc in 10 CV, hold for10 CV, then 0percent EtOAc for 5 CV. Detectionwas accomplished using anelectrospray detector held at 313 K.2-hydroxy-2-hydroxymethyltetrahydrofuran, 2. 13C NMR(acetone-d6, 125 MHz): d 23.2, 33.6, 64.7, 67.1, 102.4. 1H NMR(acetone-d6, 500 MHz): d1.61 (complex multiplet, 2H), 1.78 (complexmultiplet, 2H), 1.85 (complex multiplet, 2H), 1.97 (complexmultiplet, 2H), 2.77 (t, J 0.8, 1H), 2.81 (s, 1H), 3.36 (d, J H), 3.88(m, J 6.0, 2H), 4.01(d, J 11.5, 2H). EIMS m/z, (relative intensity)101, (100); 59, (88); 43, (28); 41, (28). A
B
C
D
E
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32
Synthesize Find similar Rx-ID: 44156040 Find similar reactions
A: 27 %Chromat. B: 33.8 %Chromat.
With copper-nickel on zirconium oxide bimetallic catalysts in isopropyl alcohol
T=220°C; 4 h; Inert atmosphereSealed tube;
Chang, Xin; Liu, An-Feng; Cai, Bo; Luo, Jin-Yue; Pan, Hui; Huang, Yao-Bing
ChemSusChem, 2016 , vol. 9, # 23 p. 3330 - 3337 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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33
Synthesize Find similar Rx-ID: 44156041 Find similar reactions
A: 33.5 %Chromat.
34
With palladium on zirconium oxide bimetallic catalysts in isopropyl alcohol
T=220°C; 4 h; Inert atmosphereSealed tube;
Chang, Xin; Liu, An-Feng; Cai, Bo; Luo, Jin-Yue; Pan, Hui; Huang, Yao-Bing
ChemSusChem, 2016 , vol. 9, # 23 p. 3330 - 3337 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 747130 Find similar reactions
75%
With oxygen; potassium iodide; sodium nitrite in water; acetonitrile
8 h; Reflux;
Chaudhari, Hemchandra K.; Telvekar, Vikas N.
Synthetic Communications, 2013 , vol. 43, # 8 p. 1155 - 1160 Title/Abstract Full Text View citing articles Show Details
18%
With potassium hydroxide in ethyl acetate
T=-78°C; Product distribution;
Hoffman, Robert V.; Kumar, Anil
Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 4011 - 4014 Title/Abstract Full Text View citing articles Show Details
With water; oxygen; copper
Reagens 4: OsO4;
Demjanow; Schuikina
Zhurnal Obshchei Khimii, 1936 , vol. 6, p. 350 Chem. Zentralbl., 1936 , vol. 107, # II p. 1905 Full Text View citing articles Show Details
Hide Details
With pyridine-4-carbaldehyde; hydrogenchloride; sodium hydroxide
1.) CH3OH, reflux, 7 h; Yield given. Multistep reaction;
Ohta, Shunsaku; Okamoto, Masao
Synthesis, 1982 , # 9 p. 756 - 758 Title/Abstract Full Text Show Details
42 % Chromat.
With 2,6-dimethylpyridine; TEMPOL; water; lithium perchlorate in acetonitrile
T=23°C; electrolysis, a platinum gauze electrode, +0.33 V (vs. Ag/Ag(1+));
Semmelhack, M. F.; Schmid, Christopher R.
Journal of the American Chemical Society, 1983 , vol. 105, # 22 p. 6732 - 6734 Title/Abstract Full Text View citing articles Show Details
With water in dimethyl sulfoxide
T=30°C; pH=7; 18 h; aq. phosphate bufferEnzymatic reaction;
Leisch, Hannes; Grosse, Stephan; Iwaki, Hiroaki; Hasegawa, Yoshie; Lau, Peter C.K.
Canadian Journal of Chemistry, 2012 , vol. 90, # 1 p. 39 - 45 Title/Abstract Full Text View citing articles Show Details
With dipotassium peroxodisulfate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; water in acetonitrile
T=20°C; 12 h; Sealed tubeIrradiationGreen chemistry;
Iqbal, Naeem; Cho, Eun Jin
Advanced Synthesis and Catalysis, 2015 , vol. 357, # 10 p. 2187 - 2192 Title/Abstract Full Text View citing articles Show Details
A
B
C
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35
Synthesize Find similar Rx-ID: 1792691 Find similar reactions
With diisobutylaluminium hydride in tetrahydrofuran; hexane
T=-78°C; 3 h; Yield given. Yields of byproduct given;
Kim, Sunggak; Ahn, Kyo Han
Journal of Organic Chemistry, 1984 , vol. 49, # 10 p. 1717 - 1724 Title/Abstract Full Text View citing articles Show Details
A: 63 % Chromat. B: 34 % Chromat. C: 2 % Chromat.
With lithium aluminium tetrahydride; cerium(III) chloride in tetrahydrofuran
0.166667 h; Ambient temperature;
Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Yamauchi, Shoji; Sakai, Shizuyoshi
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1929 - 1932 Title/Abstract Full Text View citing articles Show Details
A: 63 % Chromat. B: 34 % Chromat. C: 2 % Chromat.
With lithium aluminium tetrahydride; cerium(III) chloride
0.166667 h; Ambient temperatureWithout catalyst; Product distribution;
Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Yamauchi, Shoji; Sakai, Shizuyoshi
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1929 - 1932 Title/Abstract Full Text View citing articles Show Details
Hide Details
A: 6 % Chromat. B: 88 % Chromat. C: 4 % Chromat.
With sodium tetrahydroborate; copper(l) chloride in methanol
0.0833333 h; other metallic salts; Product distribution;
Gemal, Andre L.; Luche, Jean-Louis
Journal of the American Chemical Society, 1981 , vol. 103, # 18 p. 5454 - 5459 Title/Abstract Full Text View citing articles Show Details
With hydrogen; Ru(CO)2(OAc)2(PnBu3)(PPh3) in toluene
T=60°C; P=18751.9 Torr; 3 h;
Micoli, Francesca; Oberhauser, Werner; Salvini, Antonella; Bianchini, Claudio
Journal of Organometallic Chemistry, 2007 , vol. 692, # 11 p. 2334 - 2341 Title/Abstract Full Text View citing articles Show Details
C: 6 %Chromat.
With sodium tetrahydroborate; cerium(III) chloride heptahydrate in 2-methyltetrahydrofuran
0.0333333 h; SolventReagent/catalyst; Overall yield = 100 percentChromat.;
Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio
Tetrahedron, 2015 , vol. 71, # 7 p. 1132 - 1135 Title/Abstract Full Text View citing articles Show Details
C: 20 %Chromat.
With sodium tetrahydroborate; cerium triflate in ethanol
0.0333333 h; SolventReagent/catalyst; Overall yield = 100 percentChromat.;
Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio
Tetrahedron, 2015 , vol. 71, # 7 p. 1132 - 1135 Title/Abstract Full Text View citing articles Show Details
36
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31%
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With ammonium hydroxide; C18H12N5(1-)*Fe(3+)*2Cl(1-); dihydrogen peroxide in water; N,Ndimethyl-formamide
T=35°C; 0.75 h; Inert atmosphereSchlenk technique; Catalytic behaviorKinetics; Time; Hide Experimental Procedure
Rx-ID: 35626972 Find similar reactions
Lakk-Bogth, Dra; Harasztia, Mikls; Csonka, Rbert; Speier, Gbor; Kaizer, Jzsef
Polyhedron, 2015 , vol. 89, p. 91 - 95 Title/Abstract Full Text View citing articles Show Details
2.2 Determination of products
General procedure: Reactivity assays were performed as follows: the respective amino acid (ACCH, ACBH, ACPH, ACHH, AIBH) was dissolved in 10mL of DMF/H2O mixture (3/1 V/V) in a 20 mL sealable tube. With MeCN (10μL) as inner standard, NH4OH and the catalyst were then added to the mixture. Hydrogen peroxide was added through the septum with a syringe and the evolved ethylene, cyclobutanone, cyclopentanone, cyclohexanone or acetone was measured by removing 0.25 mL from the headspace with a gastight syringe and the sample was injected into a gas chromatograph. The concentration of the corresponding product in the headspace is linearly proportional to the concentration of the product in the reaction mixture. GC analyses were performed on a Hewlett Packard 5890 gas chromatograph equipped with a flame ionization detector and a 30m Supelcowax column.
22%
With ammonium hydroxide; [CuII(2,2'-bipyridine)(1-aminocyclopentane-1-carboxylic acid(H-
Pap, József S.; El Bakkali-Tahéri, Nadia; Fadel, Antoine; Góger, Szabina; Bogáth, Dóra; Molnár, Milán; Giorgi, Michel; Speier, Gábor; Simaan, A. Jalila; Kaizer, József
))]ClO4*H2O; dihydrogen peroxide in water; N,N-dimethyl-formamide
T=35°C; Kinetics;
European Journal of Inorganic Chemistry, 2014 , vol. 2014, # 17 p. 2829 - 2838 Title/Abstract Full Text Show Details
With [1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene]iron(III) chloride; dihydrogen peroxide in water; N,N-dimethyl-formamide
T=35°C; Catalytic behaviorKinetics;
Goger, Szabina; Bogath, Dora; Barath, Gabor; Simaan, A. Jalila; Speier, Gabor; Kaizer, Jozsef
Journal of Inorganic Biochemistry, 2013 , vol. 123, p. 46 - 52 Title/Abstract Full Text View citing articles Show Details
Hide Details
With ammonium hydroxide; dihydrogen peroxide; copper dichloride in water; N,N-dimethylformamide
T=35°C; KineticsCatalytic behavior; Reagent/catalyst; Hide Experimental Procedure
Goger, Szabina; Pap, Jozsef S.; Bogath, Dora; Simaan, A. Jalila; Speier, Gabor; Giorgi, Michel; Kaizer, Jozsef
Polyhedron, 2014 , vol. 73, p. 37 - 44 Title/Abstract Full Text View citing articles Show Details
2.8 Determination of products and kinetic measurements
General procedure: Kinetic studies on the catalytic oxidation of amino acids by CuCl2 or Cu(AA)2 complexes were performed in a 3:1 DMF–water mixture at 35°C. Assays were performed as follows: respective amino acid (3.6×10−4mol) was dissolved in 10mL of the solvent mixture in a sealable tube of 20mL. To the mixture were then added MeCN (10μL) as internal standard, the catalyst (7.2×10−8mol) and NH4OH (3.6×10−4mol). Hydrogen peroxide (32μL, 3.6×10−4mol) was then added through the septum with a syringe and the evolved product(s) were measured by removing 250μL of the headspace by GC analysis. The concentration of products in the head space are linearly proportional to the concentration of those in the reaction mixture. A
B
C
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37
Synthesize Find similar Rx-ID: 36338234 Find similar reactions
With water; hydrogen
T=160°C; P=30003 Torr; 4 h; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With methanol; acetic acid in water
T=180°C; P=7500.75 Torr; 4 h; Inert atmosphere;
Xu, Ying; Qiu, Songbai; Long, Jinxing; Wang, Chenguang; Chang, Jiamin; Tan, Jin; Liu, Qiying; Ma, Longlong; Wang, Tiejun; Zhang, Qi
RSC Advances, 2015 , vol. 5, # 111 p. 91190 - 91195 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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38
Synthesize Find similar Rx-ID: 40391967 Find similar reactions
With palladium on activated charcoal; hydrogen in water
T=275°C; P=48004.8 Torr; 2 h;
Shafaghat, Hoda; Sirous Rezaei, Pouya; Daud, Wan Mohd Ashri Wan
RSC Advances, 2015 , vol. 5, # 43 p. 33990 - 33998 Title/Abstract Full Text View citing articles Show Details
A
B
C
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39
Synthesize Find similar Rx-ID: 40391968 Find similar reactions
With hydrogen in water
T=275°C; P=48004.8 Torr; 2 h;
Shafaghat, Hoda; Sirous Rezaei, Pouya; Daud, Wan Mohd Ashri Wan
RSC Advances, 2015 , vol. 5, # 43 p. 33990 - 33998 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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40
Synthesize Find similar Rx-ID: 40657700 Find similar reactions
With 5-palladium/activated carbon; hydrogen in water
T=40 - 130°C; P=6000.6 Torr; 1.66667 h; Reagent/catalyst; Hide Experimental Procedure
Fulajtárova, Katarína; Soták, Tomáš; Hronec, Milan; Vávra, Ivo; Dobročka, Edmund; Omastová, Mária
Applied Catalysis A: General, 2015 , vol. 502, p. 78 - 85 Title/Abstract Full Text View citing articles Show Details
Experimental set up and reaction procedure
General procedure: Furfural hydrogenation reactions were performed in a 50 ml stainless steel reactor connected with a flexible metal capillary toa hydrogen supply system recording at constant pressure the con-sumption of hydrogen in defined reaction times. The reactor wasloaded with the liquid reaction mixture (usually 5 ml) and the cat-alyst. The air was purged out from the reactor by flushing withnitrogen and then four times with hydrogen. The reactor pres-surized to the desired pressure with hydrogen was placed intothermostatic oil bath, and after 5–7 min of heating, the reactantswere mixed by shaking the reactor using a vibrator. This momentwas the start of reaction. A constant hydrogen pressure was main-tained throughout the reaction. The vigorous agitation ensured thatthe measured rate of hydrogen consumption was not influencedby mass-transfer effects. Hydrogenation was stopped when during3–5 min hydrogen consumption was practically zero. The samples were analyzed using a gas chromatography (Shimadzu GC-17A)equipped with flame ionization detector by the formerly describedCuOprocedure [2]. The qualitative determination of products was doneby the external standard method using aqueous solutions of eachproduct with known concentration and response factors. Perfor-mance of catalysts was evaluated in terms of (percent) conversion offurfural and (percent) selectivity to furfuryl alcohol calculated on theamount of converted furfural A
B
C
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41
Synthesize Find similar Rx-ID: 40922082
Find similar reactions
With methanol; water in aq. phosphate buffer
T=28°C; Michael Addition; pH=6.2; Enzymatic reaction; enantioselective reaction;
Chen, Bi-Shuang; Resch, Verena; Otten, Linda G.; Hanefeld, Ulf
Chemistry - A European Journal, 2015 , vol. 21, # 7 p. 3020 - 3030 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
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42
Synthesize Find similar Rx-ID: 41216262 Find similar reactions
With methanol; acetic acid in water
T=180°C; P=7500.75 Torr; 4 h; Inert atmosphereAutoclave; Catalytic behavior; Reagent/catalyst;
Xu, Ying; Qiu, Songbai; Long, Jinxing; Wang, Chenguang; Chang, Jiamin; Tan, Jin; Liu, Qiying; Ma, Longlong; Wang, Tiejun; Zhang, Qi
RSC Advances, 2015 , vol. 5, # 111 p. 91190 - 91195 Title/Abstract Full Text View citing articles Show Details
A
B
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43
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Rx-ID: 41674726 Find similar reactions
Castro-Alvarez, Alejandro; Carneros, Héctor; Sánchez, Dani; Vilarrasa, Jaume
Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 11977 - 11985 Title/Abstract Full Text View citing articles Show Details
in benzene-d6
Equilibrium constant; Solvent;
44
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Rx-ID: 1515146 Find similar reactions
90%
With formaldehyd; silica gel; iron(III) chloride
T=20°C; 0.0833333 h;
Fadel, Antoine; Yefsah, Ramdane; Salauen, Jacques
Synthesis, 1987 , # 1 p. 37 - 40 Title/Abstract Full Text Show Details
83%
With chloral hydrate in hexane
T=25°C; 0.5 h; Inert atmosphere; SolventTemperature; Hide Experimental Procedure
Chandrasekhar, Sosale; Shrinidhi, Annadka
Synthetic Communications, 2014 , vol. 44, # 13 p. 1904 - 1913 Title/Abstract Full Text View citing articles Show Details
3
General procedure: A stirred solution of the acetal (2, 3.5 mmol) in dry hexane (5 ml), under dry nitrogen at 25 C, was treated with 1 (1.7 g, 10.6 mmol). The mixture was stirred for 2 h, treated with water, and extracted with dichloromethane (10 ml). The extracts were washed with brine solution, dried (Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography on neutral alumina(50–325 mesh, eluent: 2.5:97.5 ethyl acetate–hexane), to obtain the corresponding carbonyl compound (3). The purity was estimated to be >98percent by 1H and 13C NMRspectroscopic analysis. In the case of solid acetals, 0.5 ml of dichloromethane along with hexane was added for added solubility; in the case of thioacetals, 21.2 mmol of 1 was used fo reffective deprotection
82%
With boron trifluoride diethyl etherate; sodium iodide in acetonitrile
2 h; Heating;
Mandal, Arun K.; Shrotri, P. Y.; Ghogare, A. D.
Synthesis, 1986 , # 3 p. 221 - 222 Title/Abstract Full Text Show Details
Hide Details
98 % Chromat.
With water; β-cyclodextrin
T=20°C; 16 h;
Ji, Hong-Bing
European Journal of Organic Chemistry, 2003 , # 18 p. 3659 - 3662 Title/Abstract Full Text View citing articles Show Details
A
B
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45
Synthesize Find similar Rx-ID: 4516363 Find similar reactions
A: 50% B: 8%
With ozone in neat (no solvent) T=20°C; 10 h; UV-irradiation;
Hwang, Kuo Chu; Sagadevan, Arunachalam
Science, 2014 , vol. 346, # 6216 p. 1495 - 1498 Title/Abstract Full Text View citing articles Show Details
With 2-hydroxy-1,3-isoindolinedione; sulfuric acid; oxygen; cobalt(II) 2,4-pentanedionate
1.) CH3COOH, 100 deg C, 6 h, 2.) CH3OH, 65 deg C, 15 h; Yield given. Multistep reaction. Yields of byproduct given;
Ishii, Yasutaka; Iwahama, Takahiro; Sakaguchi, Satoshi; Nakayama, Kouichi; Nishiyama, Yutaka
Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4520 - 4526 Title/Abstract Full Text View citing articles Show Details
A
B
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46
Synthesize Find similar Rx-ID: 37304918
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With pyridoxal 5'-phosphate; recombinant ω-transaminase from Burkholderia vietnamiensis G4 in aq. phosphate buffer
T=37°C; pH=7.4; 0.0833333 h; Enzymatic reaction; enantioselective reaction; Hide Experimental Procedure
Jiang, Jinju; Chen, Xi; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming
Journal of Molecular Catalysis B: Enzymatic, 2014 , vol. 100, p. 32 - 39 Title/Abstract Full Text View citing articles Show Details
2.7. Substrate specificity and enantioselectivity
General procedure: Amino donor specificity was assayed by following the similar procedure of Section 2.5. The amino donor substrates (10 mM) listed in Table 1 reacted with pyruvate (10 mM) as amino acceptor. For racemic amino donor, the concentration was 20 mM. After the reaction, residual pyruvate was analyzed by HPLC according to Section 2.10. Amino acceptor specificity was assayed by following the similar procedure of Section 2.5. The amino acceptor substrates (10 mM) listed in Table 2 reacted with (S)-α-MBA (10 mM) as amino donor. After the reaction, the amount of produced acetophenone was analyzed and the ee values of the produced amines were determined according to Section 2.10. A
B
C
D
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47
Synthesize Find similar Rx-ID: 37472277 Find similar reactions
With tert.-butylhydroperoxide in neat (no solvent) T=26°C; 24 h;
Alshammari, Hamed; Miedziak, Peter J.; Davies, Thomas E.; Willock, David J.; Knight, David W.; Hutchings, Graham J.
Catalysis Science and Technology, 2014 , vol. 4, # 4 p. 908 - 911 Title/Abstract Full Text View citing articles Show Details
48
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With ammonium hydroxide; dihydrogen peroxide in water; N,N-dimethyl-formamide
T=35°C; Kinetics; Solvent;
A
49
Rx-ID: 38157687 Find similar reactions
Pap, Jõzsef S.; El Bakkali-Tahéri, Nadia; Fadel, Antoine; Gõger, Szabina; Bogáth, Dõra; Molnár, Milán; Giorgi, Michel; Speier, Gábor; Simaan, A. Jalila; Kaizer, Jõzsef
European Journal of Inorganic Chemistry, 2014 , # 17 p. 2829 - 2838 Title/Abstract Full Text View citing articles Show Details
B
Synthesize Find similar Rx-ID: 35100302 Find similar reactions
A: 10 %Chromat. B: 85 %Chromat.
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With (S)-α-alanine; pyridoxal 5'-phosphate; NAD; ammonium formate; alcohol dehydrogenase; lactate dehydrogenase in aq. phosphate buffer
T=30°C; pH=7.5; 24 h; Enzymatic reaction; Reagent/catalyst;
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Tauber, Katharina; Fuchs, Michael; Sattler, Johann H.; Pitzer, Julia; Pressnitz, Desiree; Koszelewski, Dominik; Faber, Kurt; Pfeffer, Jan; Haas, Thomas; Kroutil, Wolfgang
Chemistry - A European Journal, 2013 , vol. 19, # 12 p. 4030 - 4035 Title/Abstract Full Text View citing articles Show Details
A
B
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50
Synthesize Find similar Rx-ID: 35599735 Find similar reactions
A: 92 %Spectr. B: 75 %Spectr.
Sugiura, Ryo; Kozaki, Rikio; Kitani, Satoru; Gosho, Yoshinori; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Morimoto, Tsumoru; Kakiuchi, Kiyomi
Tetrahedron, 2013 , vol. 69, # 19 p. 3984 - 3990 Title/Abstract Full Text View citing articles Show Details
in acetonitrile-D3; water-d2
T=20°C; 2.66667 h; Irradiation; Hide Experimental Procedure
4.4 General procedure for photodeprotection reaction
General procedure: Irradiation reactions were carried out using an ultra-high pressure mercury lamp (SX–UI–500H, USHIO) as a light source. A CH3CN (1.0 vol percent H2O, 1.0×10−2 M) solution of acetal 7 in an NMR tube was irradiated through Pyrex filter until 7 was totally consumed. The field was determined by 1H NMR spectroscopy using 1,3,5-trioxane as an internal standard. A
B
C
D
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51
Synthesize Find similar Rx-ID: 35599736 Find similar reactions
Sugiura, Ryo; Kozaki, Rikio; Kitani, Satoru; Gosho, Yoshinori; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Morimoto, Tsumoru; Kakiuchi, Kiyomi
Tetrahedron, 2013 , vol. 69, # 19 p. 3984 - 3990 Title/Abstract Full Text View citing articles Show Details
With H218O in acetonitrile
T=20°C; Irradiation; Hide Experimental Procedure
4.5 18O labeling experiment
General procedure: As a control, a 1.0×10−2 M solution of 7d or 7j in CH3CN/H2O (99/1 v/v) was irradiated at >280 nm from an ultra-high pressure mercury lamp until 7d or 7j was totally consumed. For experiment of 7d, the reaction solution was directly analyzed by MS (CI). For experiment of 7j, aldehyde 6j, and PLPG 1d were isolated from the reaction solution and then analyzed by MS (CI), respectively. Next, a 1.0×10−2 M solution of 7d or 7j in CH3CN/H218O (99/1 v/v) was irradiated. Analysis of each resulting reaction solution was done as above. The values of label incorporation into the products were calculated from the comparison of the height of [M+H]+ peak and [M+2+H]+ peak of each labeled and unlabeled products. A
B
52
Synthesize Find similar Rx-ID: 35675784 Find similar reactions
A: 55% B: 45%
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With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II); water in 1,4-dioxane
T=135°C; 48 h; Schlenk techniqueInert atmosphere; Pressure;
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Khusnutdinova, Julia R.; Ben-David, Yehoshoa; Milstein, David
Angewandte Chemie - International Edition, 2013 , vol. 52, # 24 p. 6269 - 6272 Angew. Chem., 2013 , vol. 125, # 24 p. 6389 - 6392,4 Title/Abstract Full Text View citing articles Show Details
A
B
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53
Synthesize Find similar Rx-ID: 35936659 Find similar reactions
Huff, Chelsea A.; Kampf, Jeff W.; Sanford, Melanie S.
Chemical Communications, 2013 , vol. 49, # 64 p. 7147 - 7149 Title/Abstract Full Text View citing articles Show Details
in benzene-d6
T=25°C; 2 h; Inert atmosphereGlovebox;
A
B
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54
Synthesize Find similar Rx-ID: 36338226 Find similar reactions
With water; hydrogen
T=160°C; P=30003 Torr; 4 h; Autoclave;
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 4 h / 160 °C / 30003 Torr / pH 7 / |Autoclave View Scheme
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
With 5 palladium on charcoal; hydrogen in water
T=160°C; P=22502.3 Torr; 1 h; Hide Experimental Procedure
Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej
Applied Catalysis A: General, 2013 , vol. 468, p. 426 - 431 Title/Abstract Full Text View citing articles Show Details
General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds.
55
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With 5-hydroxymethylfuran-2-carboxaldehyde; water; hydrogen
T=160°C; P=30003 Torr; 4 h; Autoclave;
Rx-ID: 36338231 Find similar reactions
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
A
B
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56
Synthesize Find similar Rx-ID: 36338237 Find similar reactions
With water; hydrogen
T=160°C; P=30003 Torr; pH=7; 4 h; Autoclave; Reagent/catalystpH-value;
A
57
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940 Title/Abstract Full Text View citing articles Show Details
B
Synthesize Find similar Rx-ID: 36457377 Find similar reactions
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With 1,4-dioxane
T=140°C; Sealed tubeHigh pressure; KineticsMechanism; Temperature;
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Nesprias, Rosa; Eyler, Gladys; Canizo, Adriana
Australian Journal of Chemistry, 2013 , vol. 66, # 9 p. 1080 - 1087 Title/Abstract Full Text View citing articles Show Details
58
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With 1,4-dioxane
T=140°C; Sealed tubeHigh pressure; KineticsMechanism; Temperature;
Rx-ID: 36457379 Find similar reactions
Nesprias, Rosa; Eyler, Gladys; Canizo, Adriana
Australian Journal of Chemistry, 2013 , vol. 66, # 9 p. 1080 - 1087 Title/Abstract Full Text View citing articles Show Details
A
B
C
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59
Synthesize Find similar Rx-ID: 36689292 Find similar reactions
With platinum on carbon; hydrogen in water
T=175°C; P=60006 Torr; 0.5 h; Hide Experimental Procedure
Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej
Applied Catalysis A: General, 2013 , vol. 468, p. 426 - 431 Title/Abstract Full Text View citing articles Show Details
General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds.
A
B
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60
Synthesize Find similar Rx-ID: 36926888 Find similar reactions
With air T=25°C; 168 h; Overall yield = > 90 percent;
Kise, Naoki; Kawano, Yusuke; Sakurai, Toshihiko
Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12453 - 12459 Title/Abstract Full Text View citing articles Show Details
A
B
C
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61
Synthesize Find similar Rx-ID: 36977918 Find similar reactions
With tert.-butylhydroperoxide
T=26°C; P=760.051 Torr; 24 h; Reagent/catalyst;
Alshammari, Hamed; Miedziak, Peter J.; Knight, David W.; Willock, David J.; Hutchings, Graham J.
Catalysis Science and Technology, 2013 , vol. 3, # 12 p. 3372 - 3373 Title/Abstract Full Text View citing articles Show Details
62
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With hydrogen; dichlorobis(tricyclohexylphosphine)(benzylidene)rhodium in 1,2-dichloro-ethane
T=70°C; P=760.051 Torr;
Rx-ID: 9068748 Find similar reactions
Louie; Bielawski; Grubbs
Journal of the American Chemical Society, 2001 , vol. 123, # 45 p. 11312 - 11313 Title/Abstract Full Text View citing articles Show Details
With hydrogen
T=70°C; P=5171.62 Torr;
Trost, Barry M.; Thaisrivongs, David A.; Hansmann, Max M.
Angewandte Chemie - International Edition, 2012 , vol. 51, # 46 p. 11522 - 11526 Title/Abstract Full Text View citing articles Show Details
A
B
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63
Synthesize Find similar Rx-ID: 32605769 Find similar reactions
Sanchez, Dani; Bastida, David; Bures, Jordi; Isart, Carles; Pineda, Oriol; Vilarrasa, Jaume
Organic Letters, 2012 , vol. 14, # 2 p. 536 - 539 Title/Abstract Full Text View citing articles Show Details
in dimethylsulfoxide-d6
T=25°C; Equilibrium constant;
A
B
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64
Synthesize Find similar Rx-ID: 32769640 Find similar reactions
A: 39% B: 16%
With dihydrogen peroxide in acetonitrile
T=65 - 68°C; 9 h;
Sen, Rupam; Saha, Debraj; Koner, Subratanath
Catalysis Letters, 2012 , vol. 142, # 1 p. 124 - 130 Title/Abstract Full Text View citing articles Show Details
A: 5% B: 14%
With sodium hypochlorite in acetonitrile
T=65 - 68°C; 9 h;
Sen, Rupam; Saha, Debraj; Koner, Subratanath
Catalysis Letters, 2012 , vol. 142, # 1 p. 124 - 130 Title/Abstract Full Text View citing articles Show Details
A
65
B
C
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A: 10.31% B: 35.59% C: 38.89%
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With 5 Pd(II)/C(eggshell); hydrogen in water
T=175°C; P=60006 Torr; 0.5 h;
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Hronec, Milan; Fulajtarova, Katarina
Catalysis Communications, 2012 , vol. 24, p. 100 - 104 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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66
Synthesize Find similar Rx-ID: 33359682 Find similar reactions
A: 23.4% B: 6.55% C: 40.01% D: 17.46%
With hydrogen in water
T=160°C; P=60006 Torr; 0.5 h;
Hronec, Milan; Fulajtarova, Katarina
Catalysis Communications, 2012 , vol. 24, p. 100 - 104 Title/Abstract Full Text View citing articles Show Details
A
B
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67
Synthesize Find similar Rx-ID: 33564683 Find similar reactions
With hydrogen in 1,4-dioxane
T=265°C; P=18751.9 Torr; Product distribution / selectivity; Hide Experimental Procedure
Korea Research Institute Of Chemical Technology
Patent: EP2476674 A2, 2012 ; Location in patent: Page/Page column 8 ; Title/Abstract Full Text Show Details
9:
[Example 9] Production of ε-caprolactone from the adipic acid through the hydrogenation reaction [catalyst: CuO(80)SiO2 (20)]The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 265°C, the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 7. The present catalyst exhibited high selectivity of 86.5percent of ε-caprolactone. A
B
C
68
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With hydrogen in 1,4-dioxane
T=265°C; P=18751.9 Torr; 30 h; Hide Experimental Procedure
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Korea Research Institute Of Chemical Technology
Patent: EP2476674 A2, 2012 ; Location in patent: Page/Page column 8-9 ; Title/Abstract Full Text Show Details
12:
[Example 12] Production of ε-caprolactone from the adipic acid through the hydrogenation reaction [catalyst: CuO(80)SiO2(20)]The catalyst was produced by using the same method as Example 1. The adipic acid was used instead of the levulinic acid as the reactant, the temperature and the pressure of the reactor were fixed to 265°C and 25 bar, respectively, and the reaction was performed by using the same method as Example 1. The results are described in the following Table 11.As confirmed through Table 11, the conversion of adipic acid was 100percent, and the catalyst exhibited very high selectivity of 80percent or more to ε-caprolactone. A
B
C
D
E
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69
Synthesize Find similar Rx-ID: 33679462 Find similar reactions
With hydrogen; CuO(80)SiO2(20) in 1,4-dioxane
T=265°C; P=18751.9 Torr; 8 h; Inert atmosphere; Product distribution / selectivity; Hide Experimental Procedure
Korea Research Institute of Chemical Technology
Patent: US2012/197029 A1, 2012 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details
9:
The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 265° C., the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 7. The present catalyst exhibited high selectivity of 86.5percent of ε-caprolactone. A
70
B
C
D
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With hydrogen; CuO(80)SiO2(20) in 1,4-dioxane
T=265°C; P=18751.9 Torr; 30 h; Inert atmosphere; Product distribution / selectivity; Hide Experimental Procedure
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Korea Research Institute of Chemical Technology
Patent: US2012/197029 A1, 2012 ; Location in patent: Page/Page column 5-6 ; Title/Abstract Full Text Show Details
12:
The catalyst was produced by using the same method as Example 1. The adipic acid was used instead of the levulinic acid as the reactant, the temperature and the pressure of the reactor were fixed to 265° C. and 25 bar, respectively, and the reaction was performed by using the same method as Example 1. The results are described in the following Table 11.
71
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62%
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Rx-ID: 33995983 Find similar reactions
JSR Corporation
Patent: US2012/258402 A1, 2012 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
2:Synthesis of Compound (M-2)
22.0 g of the compound shown by the following formula (M-2) (compound (M-2)) was obtained in the same manner as in Example 1, except that 18.9 g (150 mmol) of cyclooctanone was used instead of 12.6 g of cyclopentanone (yield: 62percent). The 1H-NMR data for the compound (M-2) is shown below. 1H-NMR (CDCl ) δ: 1.38-2.03 (m, 23H, CH , CH ), 2.46 (br, 1H, OH), 3.38 (t, 2H, CH ), 5.36 (s, 1H, CH), 5.96 (s, 1H, CH). 3 2 3 2
60%
JSR Corporation
Patent: US2012/258402 A1, 2012 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
8:Example 8
Example 8 42.2 g of the compound shown by the following formula (M-8) (compound (M-8)) was obtained in the same manner as in Example 6, except that 24.6 g (195 mmol) of cyclooctanone was used instead of 16.4 g of cyclopentanone (yield: 60percent). The 1H-NMR data for the compound (M-8) is shown below. 1H-NMR (CDCl ) δ: 1.30-1.62 (m, 18H, CH ), 1.69 (s, 3H, CH ), 1.92-2.08 (m, 8H, CH ), 3.26-3.40 (m, 2H, CH ), 3.60-3.74 (m, 2H, CH ), 4.48 (s, 1H, CH), 5.36 (s, 1H, CH), 5.90 (s, 1H, CH). 3 2 3 2 2 2
72
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Rx-ID: 33995984 Find similar reactions
59%
JSR Corporation
Patent: US2012/258402 A1, 2012 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
3:Synthesis of Compound (M-3)
23.4 g of the compound shown by the following formula (M-3) (compound (M-3)) was obtained in the same manner as in Example 1, except that 22.5 g (150 mmol) of 2-adamantanone was used instead of 12.6 g of cyclopentanone (yield: 59percent). The 1H-NMR data for the compound (M-3) is shown below. 1H-NMR (CDCl ) δ: 1.25-2.24 (m, 23H, CH, CH , CH ), 2.54 (br, 1H, OH), 3.40 (t, 2H, CH ), 5.37 (s, 1H, CH), 5.89 (s, 1H, CH). 3 2 3 2
56%
JSR Corporation
Patent: US2012/258402 A1, 2012 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
9:Example 9
Example 9 41.1 g of the compound shown by the following formula (M-9) (compound (M-9)) was obtained in the same manner as in Example 6, except that 29.3 g (195 mmol) of 2-adamantanone was used instead of 16.4 g of cyclopentanone (yield: 56percent). The 1H-NMR data for the compound (M-9) is shown below. 1H-NMR (CDCl ) δ: 1.22-2.50 (m, 30H, CH , CH ), 3.60 (t, 2H, CH ), 3.73 (t, 2H, CH ), 5.37 (s, 1H, CH), 5.89 (s, 1H, CH). 3 2 3 2 2 A
B
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73
Synthesize Find similar Rx-ID: 34217802 Find similar reactions
Heating; Thermodynamic dataKinetics; PressureConcentrationTimeTemperature;
Rosas, Felix; Lezama, Jesus; Mora, Jose R.; Maldonado, Alexis; Chuchani, Gabriel; Cordova, Tania
Journal of Physical Chemistry A: Molecules, Spectroscopy, Kinetics, Environment, and General Theory, 2012 , vol. 116, # 37 p. 9228 - 9237,10 Title/Abstract Full Text Show Details
74
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Rx-ID: 30312920 Find similar reactions
With Nitrous oxide
T=256 - 317°C; Industry scale; Hide Experimental Procedure
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BASF SE
Patent: US2011/46413 A1, 2011 ; Location in patent: Page/Page column 14 ; Title/Abstract Full Text Show Details
1:
Example 1Reaction of Cyclopentene with Dinitrogen MonoxideThe experiment according to Example 1 was performed in a plant with a construction according to schematic FIG. 1.Through stream (2), the fresh cyclopentene feed was metered in at 116.4 g/h. This originated from the distillation of a C5 cut from a steamcracker and had the following composition (percent by weight): cyclopentene (approx. 95.1percent), cyclopentane (approx. 3.4percent), 2-methyl-2-butene (approx. 1.2percent).This stream was first mixed with stream (8) (return cyclopentene) in order to obtain a stream (3) which had the following composition: cyclopentene (approx. 46.3percent), cyclopentane (approx. 51.9percent), 2-methyl-2-butene (approx. 0.9percent), 2,2-dimethylbutane (approx. 0.81percent).This stream was then metered to the reactor (R) with a metering pump (flow rate: approx. 2076 g/h). Through stream (1), liquid N2O (N2O content >99.8percent by volume, from Messer Griesheim) was metered to the reactor at approx. 74 g/h. The molar cyclopentene:N2O ratio in the reactor feed was 0.11 mol/mol. The reactor consisted of a tube (external diameter=60.3 mm, wall thickness=2.4 mm, length=approx. 4 m). The reaction volume was (minus the volume of random packings), including connecting pieces, approx. 8 l in total.The tube was provided with an insulating jacket with an additional three-piece support heater which was set to (from the bottom) 256° C., 275° C. and 317° C. The cyclopentene conversion in straight pass was 11percent and the N2O conversion approx. 96percent. The reactor output (4) was, downstream of the pressure regulator, decompressed to 1 bar in two steps with two flash vessels (F) operated at 10 bar and 1 bar, and cooled. The gaseous components (stream (5)) were removed, and hydrocarbons present therein were very substantially condensed out in a downstream cooler (operated at +5° C., not shown in the diagram).The liquid phase (6) was separated in a distillation column (D) (bubble-cap tray column with 20 trays and liquid side draw). The bottom product (7) obtained was 138.7 g/h of a stream with the following composition: cyclopentanone (approx. 95.3percent by weight), cyclopentane (approx. 0.8percent by weight), 4-pentenal (approx. 1.3percent by weight), cyclopentene oxide (approx. 0.37percent by weight), cyclopentene dimers (approx. 0.53percent by weight), cyclopentene (approx. 0.08percent by weight).The side draw product, stream (8), which comprised 45.6percent cyclopentene, was recycled to the reactor via stream (3).At the top of the column, via the top stream (9), only very small amounts of low boilers (e.g. ethylene and acetaldehyde from the oxidation of 2-methyl-2-butene) were discharged. A
B
C
D
E
F
G
H
I
J
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75
Synthesize Find similar Rx-ID: 32318154 Find similar reactions
With zirconium(VI) oxide in ethanol
T=350°C; 5 h; Inert atmosphere;
Abe, Katsutoshi; Ohishi, Yusuke; Okada, Takuto; Yamada, Yasuhiro; Sato, Satoshi
Catalysis Today, 2011 , vol. 164, # 1 p. 419 - 424 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
F
G
H
I
J
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76
Synthesize Find similar Rx-ID: 32318157 Find similar reactions
With cerium(IV) oxide in ethanol
T=350°C; 5 h; Inert atmosphere;
Abe, Katsutoshi; Ohishi, Yusuke; Okada, Takuto; Yamada, Yasuhiro; Sato, Satoshi
Catalysis Today, 2011 , vol. 164, # 1 p. 419 - 424 Title/Abstract Full Text View citing articles Show Details
A
B
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77
Synthesize Find similar Rx-ID: 37065326 Find similar reactions
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Lu, Yun; Bradshaw, Joshua; Zhao, Yu; Kuester, William; Kabotso, Daniel
Journal of Physical Organic Chemistry, 2011 , vol. 24, # 12 p. 1172 - 1178 Title/Abstract Full Text View citing articles Show Details
in acetonitrile
T=60°C; Kinetics;
A
B
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78
Synthesize Find similar Rx-ID: 1792692 Find similar reactions
A: 13.2 % Chromat. B: 24 % Chromat.
With KHBPh3 in tetrahydrofuran
T=-78°C; 2 h;
Kim, Kwan Eung; Park, Soo Bong; Yoon, Nung Min
Synthetic Communications, 1988 , vol. 18, # 1 p. 89 - 96 Title/Abstract Full Text Show Details
With [(η5-C5Me5)2Rh2(μ-Cl)2Cl2]; sodium formate; N-(2-amino-ethyl)-4-methylbenzenesulphonamide in water
T=60°C; 1 h; Inert atmosphere; chemoselective reaction;
Li, Xuefeng; Li, Liangchun; Tang, Yuanfu; Zhong, Ling; Cun, Linfeng; Zhu, Jin; Liao, Jian; Deng, Jingen
Journal of Organic Chemistry, 2010 , vol. 75, # 9 p. 2981 - 2988 Title/Abstract Full Text View citing articles Show Details
79
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95%
With NaBO3
T=70°C; 3 h; Ionic liquid;
Bortolini, Olga; Nino, Antonio De; Garofalo, Angelo; Maiuolo, Loredana; Russo, Beatrice
Synthetic Communications, 2010 , vol. 40, # 16 p. 2483 - 2487 Title/Abstract Full Text View citing articles Show Details
65%
With bis-trimethylsilanyl peroxide; sodium hydride in tetrahydrofuran
T=20°C; Hydrolysis; 24 h;
Shahi, Shatrughan P.; Vankar, Yashwant D.
Synthetic Communications, 1999 , vol. 29, # 24 p. 4321 - 4325 Title/Abstract Full Text View citing articles Show Details
A
Rx-ID: 5311531 Find similar reactions
B
80
Synthesize Find similar Rx-ID: 29173431 Find similar reactions
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A: 64%
With bromo-dimethylsulfonium bromide
T=80°C; Beckmann rearrangement; 3 h; Ionic liquid;
Yadav, Lal Dhar S.; Garima; Srivastava, Vishnu P.
Tetrahedron Letters, 2010 , vol. 51, # 4 p. 739 - 743 Title/Abstract Full Text View citing articles Show Details
A: 64%
With bromo-dimethylsulfonium bromide; zinc(II) chloride in acetonitrile
Beckmann rearrangement; 3 h; Reflux;
Yadav, Lal Dhar S.; Patel, Rajesh; Srivastava, Vishnu P.
Synthesis, 2010 , # 11 art. no. Z04310SS, p. 1771 - 1776 Title/Abstract Full Text View citing articles Show Details
A
B
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81
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Rx-ID: 29525699 Find similar reactions
With toluene-4-sulfonic acid in benzene
Oliveira, Cristina; Morais, Goreti Ribeiro; Imai, Masao; Inohae, Eiko; Yamamoto, Chishou; Mataka, Shuntaro; Thiemann, Thies
Journal of Chemical Research, 2010 , # 3 p. 158 - 162 Title/Abstract Full Text View citing articles Show Details
A
B
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82
Synthesize Find similar Rx-ID: 29537756 Find similar reactions
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A: 92%
With Bu4N[Fe(CO)3(NO)] in hexane
T=20 - 80°C; Molecular sieveInert atmosphere;
Magens, Silja; Plietker, Bernd
Journal of Organic Chemistry, 2010 , vol. 75, # 11 p. 3715 - 3721 Title/Abstract Full Text View citing articles Show Details
83
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85%
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Rx-ID: 29565195 Find similar reactions
Kirihara, Masayuki; Yoshida, Katsumi; Noguchi, Takuya; Naito, Sayuri; Matsumoto, Nobuchika; Ema, Yukinori; Torii, Motoya; Ishizuka, Yuki; Souta, Ikuo
Tetrahedron Letters, 2010 , vol. 51, # 28 p. 3619 - 3622 Title/Abstract Full Text View citing articles Show Details
With oxygen; VOCl3 in ethyl acetate
T=20°C; 0.5 h;
A
B
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84
Synthesize Find similar Rx-ID: 4768856 Find similar reactions
With [iron(II)(H2O)6](perchlorate)2 in pyridine
T=25°C; KineticsProduct distribution;
Barton, Derek H. R.; Launay, Franck
Tetrahedron, 1997 , vol. 53, # 43 p. 14565 - 14578 Title/Abstract Full Text View citing articles Show Details
With Mn(CH3COO)2*4H2O; sodium carbonate in water
T=130°C; P=26252.6 Torr; pH=11.5; 1 h; autoclave; Product distribution / selectivity; Hide Experimental Procedure
DAICEL CHEMICAL INDUSTRIES, LTD.
Patent: EP2096097 A1, 2009 ; Location in patent: Page/Page column 13-14 ; Title/Abstract Full Text Show Details
3:
In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 70 g of the cyclopentyl hydroperoxide-containing liquid (with a cyclopentyl hydroperoxide concentration of 1.2 percent by weight) prepared in Referential Example 1, 10 g of a 20 percent by weight sodium carbonate aqueous solution (pH 11.5), and 0.035 mg of manganese acetate tetrahydrate (0.008 mg in terms of manganese (Mn)). The mixture in the autoclave was heated up to 130°C in a nitrogen atmosphere at 3.5 MPa (gauge pressure) and then, stirred for 1 hour. The resulting reaction mixture was analyzed and found to contain 1.03 g of cyclopentanone, 0.35 g of cyclopentanol, 0.06 g of cyclopentyl hydroperoxide, and 0.02 g of esters (0.01 g of cyclopentyl esters in terms of cyclopentanol). The conversion from cyclopentyl hydroperoxide was 92.7percent, the selectivity for cyclopentanone was 64.1percent and the selectivity of cyclopentanol was 10.3percent both on the basis of reacted cyclopentyl hydroperoxide. The production ratio (by mole) of cyclopentanone to cyclopentanol was 6.22.
With sodium hydroxide in water
T=130°C; P=26252.6 Torr; pH=14; 1 h; autoclave; Product distribution / selectivity; Hide Experimental Procedure
DAICEL CHEMICAL INDUSTRIES, LTD.
Patent: EP2096097 A1, 2009 ; Location in patent: Page/Page column 14-15 ; Title/Abstract Full Text Show Details
5:
In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 70 g of the cyclopentyl hydroperoxide-containing liquid (with a cyclopentyl hydroperoxide concentration of 1.2 percent by weight) prepared in Referential Example 1 and 10 g of a 20 percent by weight sodium hydroxide aqueous solution (pH 14). The mixture in the autoclave was heated up to 130°C in a nitrogen atmosphere at 3.5 MPa (gauge pressure) and then, stirred for 1 hour. The resulting reaction mixture was analyzed and found to contain 0.63 g of cyclopentanone, 0.69 g of cyclopentanol, and 0.13 g of cyclopentyl hydroperoxide (0 g of esters). The conversion from cyclopentyl hydroperoxide was 84.9percent, the selectivity for cyclopentanone was 2.5percent and the selectivity for cyclopentanol was 67.1percent both on the basis of reacted cyclopentyl hydroperoxide. The production ratio (by mole) of cyclopentanone to cyclopentanol was 0.037.
85
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Rx-ID: 8805861 Find similar reactions
94%
With formyl formic acid; Amberlyst 15
0.05 h; microwave irradiation;
Chavan; Soni; Kamat
Synlett, 2001 , # 8 p. 1251 - 1252 Title/Abstract Full Text View citing articles Show Details
88%
With potassium superoxide; tetraethylammonium bromide in N,N-dimethyl-formamide
T=20°C; 3 h;
Singh, Satish Kumar; Singh, Krishna Nand
Phosphorus, Sulfur and Silicon and the Related Elements, 2009 , vol. 184, # 9 p. 2339 - 2343 Title/Abstract Full Text View citing articles Show Details
86
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90 %Chromat.
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With 3-[{2-[4-(4-{2-[bis-(2-methoxycarbonyl-ethyl)-amino]-ethylcarbamoyl}-phenyldisulfanyl)benzoylamino]-ethyl}-(2-methoxycarbonyl-ethyl)-amino]-propionic acid methyl ester in benzene
T=20°C; 2.5 h; UV-irradiation;
Rx-ID: 28395201 Find similar reactions
Tsuboi, Takaaki; Takaguchi, Yutaka; Tsuboi, Sadao
Heteroatom Chemistry, 2009 , vol. 20, # 1 p. 1 - 11 Title/Abstract Full Text View citing articles Show Details
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87
Synthesize Find similar Rx-ID: 28722340 Find similar reactions
With sodium perchlorate; water
T=37°C; aq. buffer; Kinetics;
Vale, Nuno; Nogueira, Fatima; do Rosario, Virgilio E.; Gomes, Paula; Moreira, Rui
European Journal of Medicinal Chemistry, 2009 , vol. 44, # 6 p. 2506 - 2516 Title/Abstract Full Text View citing articles Show Details
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88
Synthesize Find similar Rx-ID: 28871530 Find similar reactions
With iron(II) sulfate in water; acetonitrile
Bernat, Virginie; Saffon, Nathalie; Maynadier, Marjorie; Vial, Henri; Andre-Barres, Christiane
Tetrahedron, 2009 , vol. 65, # 36 p. 7372 - 7379 Title/Abstract Full Text View citing articles Show Details
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C
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89
Synthesize Find similar Rx-ID: 29040619 Find similar reactions
With ethanol; water in 1,4-dioxane
T=50°C; Inert atmosphere; Kinetics; Temperature;
Miyamoto, Kazunori; Shiro, Motoo; Ochiai, Masahito
Angewandte Chemie - International Edition, 2009 , vol. 48, # 47 p. 8931 - 8934 Title/Abstract Full Text View citing articles Show Details
90
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68%
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With selenium(IV) oxide; dihydrogen peroxide in methanol; water
T=20°C; pH=7; aq. phosphate buffer;
Rx-ID: 29117275 Find similar reactions
Smith III, Amos B.; Liu, Zhuqing; Simov, Vladimir
Synlett, 2009 , # 19 p. 3131 - 3134 Title/Abstract Full Text View citing articles Show Details
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91
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Rx-ID: 29160077 Find similar reactions
A: 14.5 %Chromat. B: 7 %Chromat.
With dipotassium peroxodisulfate; 2BF4(1-)*C24H53B4Cu4N4O17(2+); water in acetonitrile
T=50°C; P=15201 Torr; 6 h; Autoclave;
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Kirillova, Marina V.; Kirillov, Alexander M.; Pombeiro, Armando J. L.
Advanced Synthesis and Catalysis, 2009 , vol. 351, # 17 p. 2936 - 2948 Title/Abstract Full Text View citing articles Show Details
92
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Rx-ID: 5144719 Find similar reactions
85%
With Zr(HSO4)4; silica gel in hexane
T=20°C; 0.42 h;
Shirini; Zolfigol; Safari; Mohammadpoor-Baltork; Mirjalili
Tetrahedron Letters, 2003 , vol. 44, # 40 p. 7463 - 7465 Title/Abstract Full Text View citing articles Show Details
85%
With (NH4)6[Mo7O24]*4H2O; dihydrogen peroxide in water; acetic acid
T=20°C; 4 h;
Ganguly, Nemai C.; Nayek, Subhasish; Barik, Sujoy Kumar; Dutta, Sanjoy
Journal of the Indian Chemical Society, 2008 , vol. 85, # 7 p. 711 - 716 Title/Abstract Full Text View citing articles Show Details
83%
With potassium peroxomonosulphate in water; acetic acid
T=40 - 45°C; Oxidation; 0.7 h;
Bose, D. Subhas; Vanajatha; Srinivas
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 7 p. 835 - 836 Title/Abstract Full Text View citing articles Show Details
Hide Details
72%
With ammonium chlorochromate on aluminum oxide in dichloromethane
6 h; Heatingvarious conditions;
Zhang, Gui-Sheng; Gong, Hui; Yang, De-Hong; Chen, Mi-Feng
Synthetic Communications, 1999 , vol. 29, # 7 p. 1165 - 1170 Title/Abstract Full Text View citing articles Show Details
With sodium perborate in acetic acid
T=40°C; Oxidation; 2.2 h;
Bandgar, B. P.; Zirange, Sangita M.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997 , vol. 36, # 8 p. 695 - 696 Title/Abstract Full Text Show Details
With dimethylammonium chlorochromate; silica gel in diethyl ether
1 h; Heating;
Zhang, Gui-Sheng; Chai, Bing
Synthetic Communications, 2000 , vol. 30, # 10 p. 1849 - 1855 Title/Abstract Full Text View citing articles Show Details
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D
E
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I
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93
Synthesize Find similar Rx-ID: 27886160 Find similar reactions
A: 12% B: 3% C: 4% E: 2% J: 12% K: 5%
With hydrogen; ruthenium
T=150 - 300°C; 0 - 4 h; Product distribution / selectivity; Hide Experimental Procedure
Battelle Memorial Institute
Patent: US7425657 B1, 2008 ; Location in patent: Page/Page column 8 ; Title/Abstract Full Text Show Details
Furfural reacted quickly over the temperature range from 150 to 250° C. At 150° C., 74percent of furfural was converted during heat-up to temperature. As shown in FIG. 7, the major product at 150° C. was tetrahydrofuran-methanol (THF-MeOH) at 10percent with a lesser amount of γ-valerolactone (GVL) at 5percent. 1,4-pentanediol (14PDO) was a lesser intermediate that was converted further to 2-methyl-tetrahydrofuranxiii (MTHF) with 2percent remaining. The demethylated versions, γ-butyrolactone (GBL) and tetrahydrofuran (THF), were also found, as was 1,2-pentanediol (12PDO). As seen in FIG. 8, there was also a reaction pathway involving cyclopentanone as an early product that was subsequently hydrogenated to cyclopentanol and 1-pentanol. At the higher temperature of 200° C. 67percent of the furfural was converted during the heat-up. As shown in FIG. 9, the THF-MeOH remained the major product (22percent) but the GVL (5percent), 14PDO (10percent) and MTHF (3percent) product slate became more prominent. The 12PDO was slightly more prominent but the GBL and THF were less so. As seen in FIG. 10, the cyclopentanone product was no longer present but cyclopentanol and 1-pentanol remained through the end of the test. At the higher temperature of 250° C. as seen in FIG. 11, 94percent of the furfural was converted during heat-up. As shown in FIG. 11, the MTHF product became dominant (30percent) along with its intermediates, GVL (14percent) and 14PDO. The THF-MeOH product was formed initially (50percent) but reacted further to a low of 4percent (at) 4 h, perhaps to the THF (12percent). GBL, which was present early on, was similarly reacted to THF. The cyclopentanone pathway products represented in FIG. 12 was still evident but all three products were reacted further and no longer present by the end of the test, having probably broken down to methane. At 300° C. no furfural survived the heat-up period. The THF-MeOH product (10percent yield at time 0) was reacted further and disappeared after the first sample. MTHF was the major product (38percent (at) 0.5 h) with THF as the important subsequent product. The reverse equilibrium product slate highlighted by GVL and levulinic acid13 were also significant. The cyclopentanone product was found (12percent) at time 0 but was reduced to trace quantities by 1.5 h. The subsequent alcohol products were not found. xiiiElliott, D. C., Fyre, J. G., Jr. (1999) Hydrogenated 5-Carbon Compound and Method of Making. U.S. Pat. No. 5,883,266.
With hydrogen; palladium
T=200 - 300°C; 4 h; Product distribution / selectivity; Hide Experimental Procedure
Battelle Memorial Institute
Patent: US7425657 B1, 2008 ; Location in patent: Page/Page column 9 ; Title/Abstract Full Text Show Details
The furfural conversion chemistry was also much different for the palladium catalyzed case. Furfural reacted quickly at these conditions. It was found only in the initial samples from 150 and 200° C. tests. At 150° C. the main product was cyclopentanone. MTHF was present at slightly higher concentration than THF-MeOH. GVL was a lesser but significant product. As shown in FIG. 19, the MTHF and THF-MeOH were recovered from the 200° C. test at about the same concentration as at 150° C., but GVL was increased to the second most prevalent product. At the higher temperature of 200° C. the cyclopentanone product was noticeably converted to cyclopentanol, as seen in FIG. 20. At 250° C. MTHF was the largest product, as seen in FIG. 21. GVL and THF-MeOH were present in nearly equal amounts. Levulinic acid showed up early but was converted (to GVL) until it was gone by the end of the test. In FIG. 22 the transition was obvious from the early production of cyclopentanone with its subsequent conversion to cyclopentanol and the final product, 1-pentanol. At 300° C. (see FIG. 23) the early production of levulinic acid led quickly to GVL and MTHF formation. Similarly GBL and THF formation were significant throughout, though the GBL was gone by the end of the test. As seen in FIG. 24, 1-pentanol was the major product present at the end of the test.
94
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Rx-ID: 28293944 Find similar reactions
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With sodium hydroxide; water
T=45 - 62.4°C; P=112.511 - 750.075 Torr; Product distribution / selectivity; Hide Experimental Procedure
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SOLVAY
Patent: WO2009/773 A1, 2008 ; Location in patent: Page/Page column 19-21 ; Title/Abstract Full Text Show Details
3; 4:
Example 3 A well stirred reactor has been fed continuously with dichloropropanol containing 0.223 g of 1,3-dichloropropane and 2.93 g of 3-chloro-l-propanol per kg of dichloropropanol at a rate of 5.07 kg/h/1 of reactor, with a sodium hydroxide solution containing 500 g of NaOH per kg at rate of 2.83 kg/h/1 of reactor and with recycled water at a rate of 6.23 kg/h/1 of reactor . The reactor has been operated at a temperature of 45 0C and at a pressure of 1 bar. The reactor was fitted with an overflow system for withdrawal of the liquid reaction medium. The liquid reaction medium was biphasic. The lighter phase which contained the salt and a small quantity of organics has been stripped with steam and the condensate has been recycled to the reactor. The heavier phase which contained the major part of the epichlorohydrin formed in the reactor has been submitted continuously to a first distillation operation under vacuum in a packed column to separate epichlorohydrin, water and the low boiling point byproducts at the top of the column and the excess of dichloropropanol and the heavy byproducts at the bottom of the column. The top fraction, collected at a temperature of 60.80C under a pressure of 150 mbar, has been submitted continuously to a second distillation in a packed column to eliminate water and the low boiling byproducts. The bottom product has been collected at normal pressure at a temperature of 115.20C; it contained 0.35 g of 1,3-dichloropropane per kg. This product has been purified by a third operation of distillation that has been realized in a batchwise manner in a glass plate distillation column under vacuum at a pressure of 790 mbar. The epichlorohydrin which has been recovered as the main distillation fraction collected between 107.4 - 107.60C contained 0.34 g of 1,3- dichloropropane per kg and is named ECH 2. Example 4 A well stirred reactor has been fed continuously with dichloropropanol containing 0.013 g of 1,3-dichloropropane and 0.0026 g of 3-chloro-l-propanol <n="21"/>per kg of dichloropropanol at a rate of 5.93 kg/h/1 of reactor, with a sodium hydroxide solution containing 500 g of NaOH per kg at rate of 2.67 kg/h/1 of reactor and with recycled water at a rate of 5.83 kg/h/1 of reactor. The reactor has been operated at a temperature of 45 0C and at a pressure of 1 bar. The reactor was fitted with an overflow system for withdrawal of the liquid reaction medium. The liquid reaction medium was biphasic. The lighter phase which contained the salt and a small quantity of organics has been stripped with steam and the condensate has been recycled to the reactor. The heavier phase which contained the major part of the epichlorohydrin formed in the reactor has been submitted continuously to a first distillation operation in a packed column to separate epichlorohydrin, water and the low boiling point byproducts at the top of the column and the excess of dichloropropanol and the heavy by-products at the bottom of the column. The top fraction, collected at a temperature of 62.40C under a pressure of 150 mbar, has been submitted continuously to a second distillation in a packed column to eliminate water and the low boiling by-products as the top product and some heavy impurities at the bottom of the column. The epichlorohydrin has been collected by condensation of a gas phase collected from the middle of the column at normal pressure and at a temperature of 116.4 0C ; it contained 0.03 g of 1,3-dichloropropane per kg and is named ECH 5. The complete composition of epichlorohydrins ECH 2 and ECH 5 and of three other epichlorohydrin samples (ECH 1, ECH 3 and ECH 4) are presented in Table 1.Their compositions obtained by gas chromatography analysis. Table 1 <n="22"/>n.d. : not detected, n.m. : not measured <n="23"/>*: l-chloro-2, 3-epoxypropane amount calculated on the basis of the total content of other organic components
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95
Synthesize Find similar Rx-ID: 28506721 Find similar reactions
With hydrotalcite supported Cu nanoparticles in para-xylene
T=130°C; 3 h; Inert atmosphere;
Mitsudome, Takato; Mikami, Yusuke; Ebata, Kaori; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi
Chemical Communications, 2008 , # 39 p. 4804 - 4806 Title/Abstract Full Text View citing articles Show Details
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96
Synthesize Find similar Rx-ID: 11162087 Find similar reactions
A: 87%
With water; oxygen; lithium bromide; copper(ll) bromide in tetrahydrofuran
T=25°C; P=760.051 Torr;
Qaseer
Polish Journal of Chemistry, 2007 , vol. 81, # 1 p. 31 - 38 Title/Abstract Full Text View citing articles Show Details
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97
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Rx-ID: 5110107 Find similar reactions
With potassium carbonate; tris(triphenylphosphine)ruthenium(II) chloride
T=56°C; other catalysts; Mechanism;
Aranyos, Attila; Csjernyik, Gabor; Szabo, Kalman J.; Baeckvall, Jan-E.
Chemical Communications, 1999 , # 4 p. 351 - 352 Title/Abstract Full Text View citing articles Show Details
With NADP embedded in ketoreductase preparation in phosphate buffer; hexane
T=24.99°C; P=750.075 Torr; pH=7.3; 4 h; Equilibrium constant; Further Variations:TemperaturesSolventsPressures;
Tewari, Yadu B.; Phinney, Karen W.; Liebman, Joel F.
Journal of Chemical Thermodynamics, 2006 , vol. 38, # 4 p. 388 - 395 Title/Abstract Full Text View citing articles Show Details
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98
Synthesize Find similar Rx-ID: 10144626 Find similar reactions
A: 51 % Chromat. B: 32 % Chromat.
With aluminium; platinum on activated charcoal in water
0.166667 h; microwave irradiation;
Miyazawa, Akira; Saitou, Kaori; Tanaka, Kan; Gaedda, Thomas M.; Tashiro, Masashi; Prakash, G. K. Surya; Olah, George A.
Tetrahedron Letters, 2006 , vol. 47, # 9 p. 1437 - 1439 Title/Abstract Full Text View citing articles Show Details
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99
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Rx-ID: 10535370 Find similar reactions
With para-methoxybenzophenone
3.5 h; Irradiation; Product distribution; Further Variations:Reagentstime;
Doohan, Roisin A.; Hannan, John J.; Geraghty, Niall W.A.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 5 p. 942 - 952 Title/Abstract Full Text View citing articles Show Details