Ethyl 2-hydroxypropanoate by Asch

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Reactions (91)

Yield

Substances (3)

Citations (128)

Conditions

References

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100%

With hydrogen

T=20°C; P=15001.5 Torr; Reagent/catalyst;

Noel, Sebastien; Leger, Bastien; Ponchel, Anne; Philippot, Karine; Denicourt-Nowicki, Audrey; Roucoux, Alain; Monflier, Eric

Catalysis Today, 2014 , vol. 235, p. 20 - 32 Title/Abstract Full Text View citing articles Show Details

80%

With t-BuOSmI2; isopropyl alcohol in tetrahydrofuran

T=65°C; 24 h; Product distribution;

Namy, J. L.; Souppe, J.; Collin, J.; Kagan, H. B.

Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2045 - 2049 Title/Abstract Full Text View citing articles Show Details

78%

With formic acid; dichlorotris(triphenylphosphine)ruthenium(II)

T=125°C; 3 h;

Watanabe, Yoshihisha; Ota, Tetsuo; Tsuji, Yasushi

Chemistry Letters, 1980 , p. 1585 - 1586 Title/Abstract Full Text Show Details

Hide Details 68%

With hydrogen; palladium on activated charcoal in ethanol

P=2585.7 Torr; 16 h;

Prasad, J. Siva; Okuniewicz, Frank J.; Delaney, Edward J.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 12 p. 3329 - 3332 Title/Abstract Full Text View citing articles Show Details

61%

98 % Chromat.

97 % Chromat.

With lithium aluminium tetrahydride; silica gel in diethyl ether

1.) room temp., 3 h 2.) reflux, 15 min;

Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Inoue, Tatsuro; Izumi, Tatsuo

Tetrahedron Letters, 1982 , vol. 23, # 44 p. 4585 - 4588 Title/Abstract Full Text View citing articles Show Details

With hydrogen; L-Tartaric acid; nickel; sodium bromide in acetic acid

T=100°C; enantioselctivity; other catalysts; Product distribution;

Brunner, H.; Amberger, K.; Wischert, T.; Wiehl, J.

Bulletin des Societes Chimiques Belges, 1991 , vol. 100, # 8 p. 585 - 595 Title/Abstract Full Text Show Details

With hydrogen; palladium/alumina; palladium in butanone

T=25°C; P=52504.2 Torr; 1 h;

Collier, Paul J.; Hall, Tracey J.; Iggo, Jonathan A.; Johnston, Peter; Slipszenko, J. Anton; Wells, Peter B.; Whyman, Robin

Chemical Communications, 1998 , # 14 p. 1451 - 1452 Title/Abstract Full Text View citing articles Show Details

With propan-1-ol; hydrogen; Cinchonidin; Pt/Al2O3

T=9.85°C; equilibrium of hemiketal-formation/hydrogenation;

Bohnen, Frank M.; Gamez, Agnes; Blackmond, Donna G.

Journal of Catalysis, 1998 , vol. 179, # 2 art. no. CA982247, p. 335 - 338 Title/Abstract Full Text View citing articles Show Details

With hydrogen; iridium

T=75°C; P=3040 Torr; 2.5 h;

Fonseca, Gledison S.; Scholten, Jackson D.; Dupont, Jairton

Synlett, 2004 , # 9 p. 1525 - 1528 Title/Abstract Full Text View citing articles Show Details

With polymethylhydrosiloxane; N,N'Dibenzylethylenediamine; diethylzinc in ethanol; toluene

T=20°C;

Bette, Virginie; Mortreux, Andre; Lehmann, Christian W.; Carpentier, Jean-Francois

Chemical Communications, 2003 , # 3 p. 332 - 333 Title/Abstract Full Text View citing articles Show Details

With hydrogen; Pt/Al2O3 in various solvent(s) T=40°C; P=71257.1 Torr; Product distribution; Further Variations:TemperaturesPressures;

Grunwaldt, Jan-Dierk; Baiker, Alfons

Physical Chemistry Chemical Physics, 2005 , vol. 7, # 20 p. 3526 - 3539 Title/Abstract Full Text View citing articles Show Details

With trimethylphosphane in tetrahydrofuran

T=20°C; 2 h;

Zhang, Wen; Shi, Min

Chemical Communications, 2006 , # 11 p. 1218 - 1220 Title/Abstract Full Text View citing articles Show Details

With O,O,O',O'-tetramethyl O,O'-thiodi-p-phenylene phosphorothioate; hydrogen; platinum in tetrahydrofuran

T=22°C; P=7500.75 Torr;

Kraynov, Alexander; Richards, Ryan

Physical Chemistry Chemical Physics, 2007 , vol. 9, # 7 p. 884 - 890 Title/Abstract Full Text View citing articles Show Details

With hydrogen; 5 alumina-supported platinum catalyst; cinchonidine in ethane; toluene

T=36°C; P=45004.5 Torr; Product distribution / selectivity; Hide Experimental Procedure

Roche Vitamins Inc.

Patent: US6646135 B1, 2003 ; Location in patent: Page/Page column 4-5 ; Title/Abstract Full Text Show Details

Examples 1-4 [00041] The process of the present invention as set forth in FIG. 1 is typically initiated by dissolving the alpha ketocarbonyl compound and the modifier in vessel (1). The resulting solution contains from about 0.1 wt percent to about 100 wt percent of the alpha ketocarbonyl compound and from about 1.x.10-5 wt percent to about 0.5 wt percent of modifier. [00042] The mass flow is started at the reaction temperature, for example, at 17° C. or 20° C. (Examples 1 and 2, respectively). The above solution containing an alpha ketocarbonyl compound and a modifier is pumped into the fixed bed reactor (2) and contacted with hydrogen to start the hydrogenation reaction. Before catalytic runs, the reactor is flushed with nitrogen. [00043] Subsequently, the content of vessel (1) is continuously pumped into the fixed bed reactor. The solution flow rate is preferably from about 0.1 to about 50 ml/minute, the preferred flow of the alpha ketocarbonyl compound is 2.x.10-5-2.x.10-2 mol/gcat/minute. More preferably, the solution flow rate is preferably from about 2.5 to about 10 ml/minute, and the flow of the alpha ketocarbonyl compound is from about 2.x.10-4-3.x.10-3 mol/gcat/minute. [00044] The modifier flow rate is preferably from about 2.x.10-9 to about 2.x.10-4 mol/gcat/minute, such as, for example, from about 2.x.10-8 to about 7.x.10-6 mol/gcat/minute. [00045] Hydrogen is continuously fed into the fixed bed reactor via flow line (3) containing a compressor (4) and a pressure control system (5). The inert gas, e.g. nitrogen, is fed into the reactor (2) via line (7). [00046] The hydrogen flow rate into the reactor is metered and monitored by a rotameter. Suitable hydrogen flow rates are from about 0.0001 mol/minute (2.4 ml/minute) to about 1 mol/minute (24000 ml/minute), for example, from about 5.x.10-6 to about 10 mol/gcat/minute. [00047] The hydrogenation reaction can be carried out at a relatively low temperature ranging between

about -20° C. and about 100° C., the preferred temperature range is from about -10° C. to about 50° C., such as for example from about 0° C. to about 20° C. [00048] The pressure in the reactor is suitably adjusted to between about 2 bar and about 150 bar, preferably from about 40 bar to about 100 bar. [00049] The effluent from the hydrogenation reaction zone is fed over a two-step expansion module (6) to a separator where the alpha hydroxy carbonyl compound is recovered. [00050] The process set forth in FIG. 2 is initiated by dissolving the alpha ketocarbonyl compound and the modifier in vessel (1) or by adding a solution containing the modifier to a liquid alpha ketocarbonyl compound. The resulting solution has the following concentration: [00051] about 0.1 wt percent to about 100 wt percent of alpha ketocarbonyl compound; and [00052] about 1.x.10-6 wt percent to about 0.5 wt percent of modifier. [00053] The reactor vessel (2) is charged with a supercritical solvent via flow line (3) containing a compressor (4) and a pressure control system (5). [00054] The organic flow is started at a reaction temperature of, for example, about 50° C. (Example 3) or 36° C. (Example 4). The solution set forth above is pumped into the fixed bed reactor (2) and contacted with hydrogen to start the hydrogenation reaction. [00055] Subsequently, the content of vessel (1) is continuously pumped into the fixed bed reactor with the same solution flow rate as in the process according to FIG. 1. [00056] The flow rate of the supercritical co-solvent is preferably from about 50 ml/minute to about 5000 ml/minute. [00057] When using a liquid alpha ketocarbonyl compound, the supercritical co-solvent is used with a flow rate of about 50 ml/minute to about 5000 ml/minute. [00058] The modifier flow rate is preferably from about 2.x.10-11 to about 2.x.10-4 mol/gcat/min. [00059] Hydrogen is continuously fed into the fixed bed reactor via flow line (7) containing a pressure control system (5). The hydrogen flow rate into the reactor was metered and monitored by a rotameter. [00060] Suitable hydrogen flow rates are from about 0.0001 mol/minute (2.4 ml/minute) to about 1 mol/minute (24000 ml/minute) such as for example from 5.x.10-6 to about 10 mol/gcat/minute. [00061] The hydrogenation reaction can be carried out at a relatively low temperature ranging between about 20° C. to about 100° C., preferably from about 30° C. to about 60° C., such as for example from about 35° C. to about 50° C. The pressure is suitably adjusted to between about 2 bar to about 150 bar, preferably about 40

bar to about 100 bar. 99 % Chromat.

With hydrogen; rhodium in aluminum oxyhydroxide in hexane

T=20°C; 1 h;

Park, In Soo; Kwon, Min Serk; Kang, Kyung Yeon; Lee, Jae Sung; Park, Jaiwook

Advanced Synthesis and Catalysis, 2007 , vol. 349, # 11-12 p. 2039 - 2047 Title/Abstract Full Text View citing articles Show Details

With Pt/SiO2; hydrogen; acetic acid

T=17.84°C; P=750.075 Torr; 4 h; Inert atmosphere; Kinetics;

Schmidt, Erik; Vargas, Angelo; Mallat, Tamas; Baiker, Alfons

Journal of the American Chemical Society, 2009 , vol. 131, # 34 p. 12358 - 12367 Title/Abstract Full Text View citing articles Show Details

100 %Chromat.

With hydrogen in ethanol

T=50°C; P=30003 Torr; 2.5 h; chemoselective reaction;

Jahjah, Mohamad; Kihn, Yolande; Teuma, Emmanuelle; Gomez, Montserrat

Journal of Molecular Catalysis A: Chemical, 2010 , vol. 332, # 1-2 p. 106 - 112 Title/Abstract Full Text View citing articles Show Details

With hydrogen; CND in ethanol

T=20°C; P=30003 Torr; 1 h;

Favier, Isabelle; Picurelli, David; Pradel, Christian; Durand, Jerome; Milani, Barbara; Gomez, Montserrat

Inorganic Chemistry Communications, 2010 , vol. 13, # 6 p. 766 - 768 Title/Abstract Full Text View citing articles Show Details

With Pt/alumina; hydrogen in toluene

T=20°C; P=37503.8 Torr; 0.5 h; Kinetics;

Talas, Emilia; Margitfalvi, Jozsef L.; Egyed, Orsolya

Journal of Catalysis, 2009 , vol. 266, # 2 p. 191 - 198 Title/Abstract Full Text View citing articles Show Details

With hydrogen in acetic acid

T=19.84°C; P=37503.8 - 45004.5 Torr;

Chen, Zhijian; Guan, Zaihong; Li, Mingrun; Yang, Qihua; Li, Can

Angewandte Chemie - International Edition, 2011 , vol. 50, # 21 p. 4913 - 4917 Title/Abstract Full Text View citing articles Show Details

With LACTIC ACID in water

T=40°C; pH=6.5; 6 h; Irradiation;

Li, Jun; Yang, Jinhui; Wen, Fuyu; Li, Can

Chemical Communications, 2011 , vol. 47, # 25 p. 7080 - 7082 Title/Abstract Full Text View citing articles Show Details

With hydrogen in water

T=20°C; P=15001.5 Torr; 6 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure

Chau, Nguyet Trang Thanh; Guegan, Jean-Paul; Menuel, Stephane; Guerrero, Miguel; Hapiot, Frederic; Monflier, Eric; Philippot, Karine; Denicourt-Nowicki, Audrey; Roucoux, Alain

Applied Catalysis A: General, 2013 , vol. 467, p. 497 - 503 Title/Abstract Full Text View citing articles Show Details

General procedure for high pressure hydrogenation reactions

General procedure: The stainless steel autoclave was charged with the aqueous colloidal ruthenium suspension (10 mL, 1.44 × 10−2 mmol or 1.00 × 10−2 mmol for the catalyst prepared by one-pot or cascade methods, respectively) and appropriate substrate ([substrate]/[Ru0] ratio = 100/1). The autoclave was degassed three times and hydrogen gas was admitted to the system at a constant pressure (20 bars). The mixture was stirred vigorously at room temperature for time (h). Samples were removed from time to time to monitor the reaction by gas chromatography in previously mentioned conditions.

91 %Spectr.

With di-μ-chloro-bis(η4-1,5cyclooctadiene)diiridium; hydrogen; CND in methanol

T=25°C; P=7500.75 Torr; 2 h; AutoclaveSealed tube; Solvent;

Du, You; Li, Chun; Tan, Xiaoyun; Fu, Haiyan; Zheng, Xueli; Li, Ruixiang; Chen, Hua

Asian Journal of Chemistry, 2014 , vol. 26, # 2 p. 319 - 322 Title/Abstract Full Text View citing articles Show Details

With formic acid; 4-methoxy-N-(1-(naphthalen-2yl)ethylidene)aniline; sodium formate in water

T=80°C; pH=4.5; 14 h; Inert atmosphere; chemoselective reaction;

Talwar, Dinesh; Wu, Xiaofeng; Saidi, Ourida; Salguero, Noem Poyatos; Xiao, Jianliang

Chemistry - A European Journal, 2014 , vol. 20, # 40 p. 12835 - 12842 Title/Abstract Full Text View citing articles Show Details

With hydrogen

T=100°C; P=525.053 Torr; KineticsCatalytic behaviorThermodynamic data; PressureTemperature; chemoselective reaction;

Gmeiner, Julia; Behrens, Silke; Spliethoff, Bernd; Trapp, Oliver

ChemCatChem, 2016 , vol. 8, # 3 p. 571 - 576 Title/Abstract Full Text View citing articles Show Details

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A: 84 % Chromat.

With tin(IV) chloride

T=90°C; 1 h;

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Hayashi, Yukiko; Sasaki, Yoshiyuki

Chemical Communications, 2005 , # 21 p. 2716 - 2718 Title/Abstract Full Text View citing articles Show Details

A: 91 %Chromat. B: 9 %Chromat.

With Zeolite NH4-Y 450 T=89.84°C; 6 h;

Pescarmona, Paolo P.; Janssen, Kris P. F.; Delaet, Chloe; Stroobants, Christophe; Houthoofd, Kristof; Philippaerts, An; De Jonghe, Chantal; Paul, Johan S.; Jacobs, Pierre A.; Sels, Bert F.

Green Chemistry, 2010 , vol. 12, # 6 p. 1083 - 1089 Title/Abstract Full Text View citing articles Show Details

With Zeolite USY CBV 600 T=119.84°C; 3 h; Autoclave;

Pescarmona, Paolo P.; Janssen, Kris P. F.; Delaet, Chloe; Stroobants, Christophe; Houthoofd, Kristof; Philippaerts, An; De Jonghe, Chantal; Paul, Johan S.; Jacobs, Pierre A.; Sels, Bert F.

Green Chemistry, 2010 , vol. 12, # 6 p. 1083 - 1089 Title/Abstract Full Text View citing articles Show Details

Hide Details A: 61.2 %Chromat. B: 21.2 %Chromat.

Pighin; Dez; Di Cosimo

Applied Catalysis A: General, 2016 , vol. 517, p. 151 - 160 Title/Abstract Full Text View citing articles Show Details

T=99.84°C; P=1875.19 Torr; 7 h; Inert atmosphere; Reagent/catalyst; Hide Experimental Procedure

2.3. Catalytic testing

The liquid-phase reaction of dihydroxyacetone, DHA (Aldrich,97percent) with ethanol (Merck, 99.8percent) was carried out at 353 K and atan autogenous pressure of 250 kPa in a batch PARR reactor. In a typi-cal experiment, a solution of DHA in ethanol with ethanol/DHA = 43(molar ratio) was loaded in the reactor and a catalyst/DHA weightratio of 43percent was used. Catalysts were thermally treated ex-situ inair flow at the corresponding calcination temperature to removeadsorbed water. After introducing the reactant mixture the reactorwas sealed and flushed with N2and then the mixture was heatedup to the reaction temperature under stirring (400 rpm). Then, thecatalyst as ground powder was added to the reaction mixture tostart the reaction. Inter- and intra-particle diffusional limitationswere verified to be negligible. Quantification of reaction productswas carried out after proper product identification using a ThermoScientific Trace 1300 gas chromatograph (GC) with a Thermo Scien-tific TR-5MS capillary column coupled to a Thermo Scientific ISQ QDMS unit. Main reaction products were glyceraldehyde (GLA), pyru-vic aldehyde (PA), ethyl lactate (EL), pyruvic aldehyde hemiacetal(PAHA) and pyruvic aldehyde diethyl acetal (PADA). Minor prod-ucts include glyceraldehyde diethyl acetal. Solutions containingweighted amounts of the different reactants and products and thestandard (n-octanol, BDH, 99percent) were injected in the GC; the com-pound concentration was varied in each solution. Molar responsefactors relative to the standard were calculated using the GC peakarea of each compound and the corresponding molecular weight.All reagents were analytical grade

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With molybdenum(VI) oxide

T=100°C; Molecular sieve; Catalytic behavior; TemperatureReagent/catalyst;

Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

With mesoporous Zr-SBA-15 silicate in water

T=260°C; P=20686.5 Torr; 2 h; Inert atmosphere;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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With mesoporous Zr-SBA-15 silicate in water

T=260°C; P=20686.5 Torr; 2 h; Inert atmosphere; Temperature;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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With mesoporous Zr-SBA-15 silicate in water

T=220°C; P=20686.5 Torr; 2 h; Inert atmosphere; Temperature;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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With mesoporous Zr-SBA-15 silicate in water

T=160°C; P=20686.5 Torr; 2 h; Inert atmosphere;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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With mesoporous Zr-SBA-15 silicate in water

T=240°C; P=20686.5 Torr; 2 h; Inert atmosphere; Temperature;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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With mesoporous Zr-SBA-15 silicate in water

T=180°C; P=20686.5 Torr; 2 h; Inert atmosphere;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

With mesoporous Zr-SBA-15 silicate in water

T=160°C; P=20686.5 Torr; 2 h; Inert atmosphere;

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8.2%

With zirconium oxide in water

T=260°C; P=20686.5 Torr; 6 h; Inert atmosphere; Temperature;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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A: 30.1% B: 13.5%

With mesoporous Zr-SBA-15 silicate in water

T=260°C; P=20686.5 Torr; 6 h; Inert atmosphere; Temperature;

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

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A: 5.7% B: 5.1%

Yang, Lisha; Yang, Xiaokun; Tian, Elli; Lin, Hongfei

ChemSusChem, 2016 , vol. 9, # 1 p. 36 - 41 Title/Abstract Full Text View citing articles Show Details

With SBA-15 silica in water

T=260°C; P=20686.5 Torr; 6 h; Inert atmosphere;

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A: 77.6 %Chromat. B: 5.4 %Chromat.

With tin(ll) chloride

T=79.84°C; P=1875.19 Torr; 7 h; Inert atmosphere; Hide Experimental Procedure

Pighin; Dez; Di Cosimo

Applied Catalysis A: General, 2016 , vol. 517, p. 151 - 160 Title/Abstract Full Text View citing articles Show Details

2.3. Catalytic testing

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A: 40.6 %Chromat. B: 20.1 %Chromat. C: 22.5 %Chromat.

Pighin; Dez; Di Cosimo

Applied Catalysis A: General, 2016 , vol. 517, p. 151 - 160 Title/Abstract Full Text View citing articles Show Details

T=79.84°C; P=1875.19 Torr; 7 h; Inert atmosphere; Reagent/catalyst; Hide Experimental Procedure

2.3. Catalytic testing

Pighin; Dez; Di Cosimo

Applied Catalysis A: General, 2016 , vol. 517, p. 151 - 160 Title/Abstract Full Text View citing articles Show Details

T=79.84°C; P=1875.19 Torr; 7 h; Inert atmosphere; Reagent/catalyst; Hide Experimental Procedure

2.3. Catalytic testing

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Stage #1: With hafnium-containing BEA zeolites in toluene

T=120°C; Aldol Condensation; 1 h; Stage #2: T=550°C; 5 h; Calcination; Catalytic behavior; Reagent/catalyst;

Wang, Yuran; Lewis, Jennifer D.; Román-Leshkov, Yuriy

ACS Catalysis, 2016 , vol. 6, # 5 p. 2739 - 2744 Title/Abstract Full Text View citing articles Show Details

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95%

With Novozym 435 24 h; Ionic liquidEnzymatic reaction;

Major, Brigitta; Nemeth, Gergely; Belafi-Bako, Katalin; Gubicza, Laszlo

Chemical Papers, 2010 , vol. 64, # 2 p. 261 - 264 Title/Abstract Full Text View citing articles Show Details

83%

With sulfuric acid in ethanol

4 h; Reflux;

Watanabe, Kohtaro; Andou, Yoshito; Shirai, Yosihito; Nishida, Haruo

Chemistry Letters, 2010 , vol. 39, # 7 p. 698 - 699 Title/Abstract Full Text View citing articles Show Details

82%

T=25 - 82°C; Product distribution / selectivity; Hide Experimental Procedure

Board of Trustees of Michigan State University

Patent: US2006/14977 A1, 2006 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details

1; 2; 3; 4; 5; 6; 7; 8:

EXAMPLES 1 TO 8; Bench-scale ethyl lactate formation. The following experiments in Examples 1 to 8, involve lactic acid and alcohols, using the bench-scale reactive distillation process for producing organic acid esters of the present invention. Ethyl Lactate Formation: In the reactive distillation process for ethyl lactate formation, absolute ethanol or azeotropic ethanol was fed near the bottom of the column and lactic acid solution in water was fed near the top of the column. Ethyl lactate was generated in the reactive zone of the distillation column and exited at the bottom of the column. Depending on the feed compositions, ethyl lactate sometimes contained a small quantity of ethanol and water that was easily separated by simple distillation and recycled. Water and excess ethanol exited at the top of the column. If the reactive distillation process was integrated into an existing ethanol production facility, the ethanol/water top product can be recycled back into the process to recover the unused ethanol in absolute form. Alternatively, both recycled azeotropic and absolute ethanol can be fed into the column either at the same or at different locations of the reactive distillation column to produce ethyl lactate. Experiments performed for ethyl lactate formation are given in Table 1; a schematic of the reactant and product flow for a typical experiment (Example 5) is given in FIG. 1. Absolute ethanol was fed at the bottom of the reactive distillation column reactive zone and lactic acid solution at the top of the reactive zone. Ethanol and water were collected at the top of the column and ethyl lactate with unreacted lactic acid were collected from the column reboiler. A small quantity of ethyl lactate was observed in the distillate stream for some experiments, but that loss was overcome by optimizing column operation. The highest lactic acid conversion observed was 83percent (Example 5); this number is significant for a relatively short distillation column and is much higher than the equilibrium lactic acid conversion (-55percent) at the same temperature. This conversion was achieved without reflux and with lactic acid fed very near the top of the column; thus the column was operated essentially as a reactive stripping column. Reasonable purity of ethyl lactate (80 mol percent) was observed from the small column with the majority of impurity being unreacted lactic acid and small quantities of ethanol and water. A taller column, where additional conversion of lactic acid and better stripping of ethanol and water can be achieved, provides a bottoms product of essentially pure ester. It should be noted that Examples 5-8 in Table 1 were conducted by preheating the ethanol feed to an elevated temperature (82° C.) where it is vaporized. This results not only in reduced reboiler duty but in a lower water content in the bottom product. Ethanol preheating has a beneficial effect in column operation. Hide Details 78.34%

With sulfuric acid

T=80°C; P=760.051 Torr; 6 h; Large scale; Reagent/catalyst; Hide Experimental Procedure

CARGILL, INCORPORATED; ABRAHAM, Timothy Walter; GOKARN, Ravi R.

Patent: WO2015/58116 A1, 2015 ; Location in patent: Paragraph 00073 ; Title/Abstract Full Text Show Details

Experiments may be carried out using a SOL jacketed reactor. First, 17.7 kilograms ethanol is added to the reactor and heated to 50 °C by passing hot water through the reactor jacket. The hot wa ter is circulated using a hot water bath. 17.7 kilograms of recovery bottom sample from a lactic acid process, the composition of which is specified in Table 3, is preheated to 78-80 °C and added to the reactor. To this first mixture, 2percent by weight relative to the recovery bottom of 98percent sulfuric acid is added as the catalyst. The reaction is carried out for 6 hours at 78-80°C and at atmospheric pressure to form the reaction product. A sample of the reaction mixture is taken from the reactor and ethyl lactate concentration is determined using the UPLC method. The reaction mixture has 12.94 kilograms of ethyl lactate which equates to a percent yield of 78.34percent, The synthesized ethyl lactate is subsequently neutralized using sodium ethoxide and the neutralized reaction mixture is used as a feed for the distillation. With tetrachloromethane

unter Abdestillieren des entstehenden Wassers;

D'Ianni; Adkins

Journal of the American Chemical Society, 1939 , vol. 61, p. 1675,1676 Full Text Show Details

With benzenesulfonic Acid; benzene

Ciocca; Semproni

Ann.Chim.applic., 1935 , vol. 25, p. 319,320 Chem. Zentralbl., 1935 , vol. 106, # II p. 3084 Full Text Show Details

With sulfuric acid

T=100°C; bei pH 1 bis 1.4;

Smith; Claborn

Industrial and Engineering Chemistry, 1940 , vol. 32, p. 693 Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2434300 , 1945 ; Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2465772 , 1945 ; Full Text Show Details

Sealtest Inc.

Patent: US2390140 , 1944 ; Full Text Show Details

Sealtest Inc.

Patent: US2406648 , 1942 ; Full Text Show Details

With chlorosulfonic acid

Gonzalez R.

CienciaChem.Abstr., 1947 , vol. 8, p. 175 CienciaChem.Abstr., 1949 , p. 127 Full Text Show Details

With toluene-4-sulfonic acid

durch Destillation;

Wuyts; Bailleux

Bulletin des Societes Chimiques Belges, 1920 , vol. 29, p. 61,66 Chem. Zentralbl., 1920 , vol. 91, # I p. 817 Full Text Show Details

T=170 - 180°C;

Wislicenus

Justus Liebigs Annalen der Chemie, 1863 , vol. 125, p. 62,66 Full Text Show Details

With anhydrous copper sulphate; copper(II) sulfate

Clemmensen; Heitman

American Chemical Journal, 1909 , vol. 42, p. 335 Full Text Show Details

T=170 - 180°C; im Rohr;

Schreiner

Justus Liebigs Annalen der Chemie, 1879 , vol. 197, p. 13 Full Text Show Details

von der Brueggen

Justus Liebigs Annalen der Chemie, 1868 , vol. 148, p. 227 Full Text Show Details

Friedel; Wurtz

Annales de Chimie (Cachan, France), 1861 , vol. <3>63, p. 102 Full Text Show Details

T=105°C; 5.73333 h; Heating / reflux; Equilibrium constant; Hide Experimental Procedure

A. E. Staley Manufacturing Co.

Patent: US6664413 B1, 2003 ; Location in patent: Page column 11 ; Title/Abstract Full Text Show Details

1:EXAMPLE 1; Vapor-Liquid Equilibrium in Vessel 2

A glass vessel was charged with a mixture of lactic acid, water, ethyl-lactate, and ethanol as shown in Table 1. It was heated to boiling point and stirred. Overhead vapors were drawn off via an overhead vapor line to a condenser. A mixture of ethanol, ethyl lactate, and water as shown in Table 1 was fed continuously over a period of 5 hours and 44 minutes via a subsurface liquid addition line. The vessel heat input rate was adjusted to obtain a constant level in the vessel. The temperature of the liquid in the pot was about 105° C. and the vapor 101-103° C. [00095] Three samples of overhead vapor taken during the run were analyzed and showed similar concentrations. The composition of the second such sample is shown in Table 1. The final pot liquor is shown in Table 1 also. [00096] Note that in this experiment the subsurface feed did not contain lactic acid. This test was to examine vapor-liquid equilibrium conditions and determine if an overhead vapor rich in ethyl lactate could be removed from a slowly reacting or non-reacting broth. [00097] The molar ratio of total ethyl groups to total lactyl groups in the overhead vapor is seen in this case to be about 6:1. The liquor is in reaction equilibrium with a K-value of 2.80, where K is the molar concentration ratio K=[ethyl-lactate]* [water]/([ethanol]*[lactic acid]). Here [ ] means mole/liter. This represents the limit of technology previously reported, wherein a relatively high ratio of ethanol to lactic acid must be used if the vapor-liquid equilibrium and the reaction equilibrium occur in the same vessel. To obtain more efficient usage of ethanol and lower steam and energy costs, a more effective method is necessary for conducting the reaction and vapor-liquid equilibration process. [00098] Note that neither this example and nor Example 2 represent a process that would likely be used commercially. This is because the feed in both examples is a mixture that contains only ethyl lactate, ethanol, and water. This stream is fed to the vessel as part of the study of the vapor-liquid equilibrium conditions. Results from these studies are then used in calculational models of the process combining the reaction equilibrium in vessel 1 and the vapor liquid equilibrium in vessel 2. in water

Industry scale; Equilibrium constant; Hide Experimental Procedure

A. E. Staley Manufacturing Co.

Patent: US6664413 B1, 2003 ; Location in patent: Page column 12-13; 14-15 ; Title/Abstract Full Text Show Details

3; 4; 6:EXAMPLE 3 Simulated Process with Recycle and Two Vessels

Vapor-liquid equilibrium data were used to create a simulation model of two vessels connected with recycle. The first vessel was operated in the simulation at sufficient temperature, pressure, holdup time, and catalyst level such that the liquid effluent is substantially at reaction equilibrium. The second vessel was operated at lower levels of one or more of temperature, holdup time, or catalyst level than the first vessel, such that the liquid effluent from vessel 2 did not approach reaction equilibrium. [00105] A feed of 68,229 lb/hr of a wet ethanol stream containing 90percent ethanol and 10percent water was fed to vessel 1, together with 28,120 lb/hr of a solution that was nominally 80percent lactic acid and 20percent water. Either or both streams may contain substantial impurities, although they are not modeled with such in this example. Additionally to vessel 1 was fed a recycle stream from vessel 2. This stream may be at any of a range of floarates as shown in the next example. For this example, the flowrate was selected to be 59,500 lb/hr. The three feed streams were combined. The molar reaction K-ratio for the combined feed stream was 1.96. This was less than the equilibrium value of 2.85 and thus reaction could proceed for the formation of ethyl lactate in the first vessel. [00106] Vessel 1 acted as a plug flow reactor and reached reaction equilibrium. The ethanol, ethyl lactate, lactic acid, and water were in reaction equilibrium. The equilibrium constant depends on the level of ethanol, the temperature, and the level of water. Under these conditions, for purposes of illustration, a value of 2.85 for the molar reaction equilibrium constant was chosen. The liquid effluent from vessel 1 comprised. approximately, the following: ethanol 52,908 lb/hr; water 18,446 lb/hr; ethyl-lactate 69,494 lb/hr, and lactic acid 15,000 lb/hr. This illustrative example does not consider dimers or oligomers of lactic acid or of ethyl lactate. However, in later examples

we shall see that this does not materially affect the general nature of the result. [00107] This example used calculated estimations of the vapor-liquid equilibrium. The effluent from vessel 1 was fed to vessel 2. Sufficient heat and/or vacuum is applied to vessel 2 to remove an overhead vapor of the following composition: ethanol 49,900 lb/hr; water 16,900 lb/hr; ethyl lactate 29,500 lb/hr, and a small quantity of lactic acid. The liquid residue in vessel 2 comprised the balance of the material: ethanol 3,000 lb/hr; water 1,500 lb/hr; ethyl lactate 40,000 lb/hr, and lactic acid 15,000 lb/hr. This liquid residue formed the 59,500 lb/hr that is recycled to the first vessel. The molar reaction K-ratio for this stream was 59.37. This was far above the equilibrium value of 2.85 and shows that vessel 2 was not near reaction equilibrium. [00108] The vapor liquid equilibrium process occurring in vessel 2 was modeled approximately here, and thus this example was a close but not exact representation of real behaviour. The molar vapor-liquid equilibrium K-values in the model were as follows: ethyl-lactate 0.5, water 1.0, and ethanol 3.8. Under similar conditions in Example 1 above, real experimental K-values were observed of ethyl-lactate 0.49, water 1.05, and ethanol 3.80.; An example similar to Example 3 was modeled with the recycle rate being varied. The ethanol feed was 15 ton/hour of 90percent ethanol 10percent water. The lactic acid feed was 5.6 ton/hour of 80percent nominal lactic acid with 20percent nominal water, on a weight basis. The recycle stream from vessel 2 to vessel 1 was varied from 5 ton/hour to as much as 1,000 ton/hour. [00110] It is found that with a recycle rate of less than 11 tons/hour, there was insufficient lactic acid in vessel 1 for forward reaction to occur. Thus if the recycle is insufficient, then the reaction cannot proceed. At a recycle rate of 10 ton/hour, the reaction equilibrium constant in vessel 1 would need to be 3.091 for reaction to proceed at all. This is higher than the true value of 2.56 to 2.85 for this system. As the recycle rate was increased to 80 ton/hour, the reaction K-ratio of the reagents feeding vessel 1 dropped to 2.061. At this ratio, the average rate of reaction in vessel 1 will be greatest. [00111] It was found that with recycle rates above 80 tons/hour the K-ratio started to increase again. Thus in terms of average reaction rate, the recycle rate of 80 tons/hour represented an optimum. Note however that increasing the recycle ratio tends to increases the mass flowrate through the reactor. The optimum reactor size is determined by a combination of the effect of recycle ratio on rate and the effect of recycle ratio on mass rate. The optimum for this set of conditions will be between 20 and 50 tons/hour. This represents a recycle rate equal to 0.97 to 2.43 pounds per hour of recycle for each pound per hour of total feed streams.; An experiment similar to that of the previous example was undertaken, but the bottoms were successively recycled four times, identified here as Runs 1, 2, 3, and 4, from vessel 2, the vapor-liquid separation device or wiped film evaporator, to vessel 1, the reaction equilibrium vessel. Upon each recycle, fresh ethanol and 88percent lactic acid was added to the bottoms prior to heating and reacting in vessel 1. Catalyst was added for the first cycle but not for subsequent cycles. The total mass of material processed in the vessel 1 reactor in each cycle was, for runs 1 through 4 respectively, 3386 grams, 3083 grams, 2987 grams, and 2830 grams. This material was then fed to vessel 2. The quantity of overhead vapor collected in each case was 1524, 1445, 1357, and 1349 grams. This represented in total about 20 hours of operation for the four recycle tests. Once again we can calculate the K value for the liquid from the final vessel 2 sample and will find that it is far from reaction equilibrium. The overhead vapors in each case are rich in ethyl-lactate, the desired product. With sulfuric acid in water

T=100°C; P=1125.11 Torr; 30 h; Heating / reflux; Product distribution / selectivity; Hide Experimental Procedure

Martino-Gauchi, Georges; Teissier, Remy

Patent: US2006/14976 A1, 2006 ; Location in patent: Page/Page column 3-4 ; Title/Abstract Full Text Show Details

EXAMPLE Preparation of Ethyl Lactate A test is carried out in a device as represented in FIG. 1. The reactor (1) has a capacity of 2 1. The PSA system (7) is composed of 2 identical columns (A and B) filled with molecular sieves, Siliporite NK30, 3 . The distillation column is filled with a Sulzer Ex packing with a diameter equal to 20 mm. It has 10 theoretical plates. The course of the test was as follows: In a first step, a lactic acid composition is esterified with ethanol under batchwise conditions in the reactor (1). The esterification is carried out at a pressure greater than atmospheric pressure and at a temperature in the region of 100° C. Then, in a second step, when the degree of conversion of the lactic acid has reached approximately 95percent, the esterification reaction is continued continuously in accordance with the present invention according to operating conditions described below. Batchwise Esterification (Start-Up) The following are introduced into the reactor (1): 391 g of an 87percent lactic acid composition, i.e. 342 g of 100percent lactic acid (3.8 mol), 667.4 g of absolute ethanol, i.e. 14.5 mol, which corresponds to an ethanol/lactic acid initial molar ratio equal to 3.81, 3.3 g of 98percent H2SO4 (0.033 mol), i.e. 0.86 mol percent with respect to the lactic acid employed. The reactor is placed under a pressure of 1.5 bar and then the reaction medium is stirred and brought to reflux, which corresponds to a temperature substantially equal to 100° C. In order to bring the batch to complete conversion (greater than 95percent), a gas mixture comprising water and ethanol is continuously extracted from the reaction medium using the distillation column (5), at a column bottom temperature in the region of 100° C. and an absolute pressure equal to 1.5 bar, and then this mixture is dehydrated by conveying it into the PSA system (7) which operates under an absolute pressure of 1.5 bar, from which pure ethanol exits at (9), which ethanol continuously feeds the esterification reaction medium present in the reactor, and from which a water/ethanol mixture exits at (10) during the desorption stage, which water/ethanol mixture is distilled in the distillation column (11), from which a water/ethanol azeotrope exits at (13), which water/ethanol azeotrope is directed to the top of the distillation column (5), thus making it possible to provide reflux at the top of said distillation column. The water exits at (12). The progress of the reaction is monitored by determining the degree of conversion of the lactic acid, measured by GC. When the degree of conversion of the lactic acid has reached approximately 95percent, which is achieved approximately at the end of 6 hours, the esterification is continued continuously. The PSA operates in an identical fashion throughout the manufacturing operation. Continuous Esterification Then, simultaneously, the esterification reaction medium is fed continuously with: 87percent lactic acid composition, fresh ethanol plus ethanol recycled via (9), while maintaining the fresh ethanol/lactic acid molar ratio in the region of 4, 98percent sulfuric acid and heavy products originating from the purification region (15) via (18). Simultaneously, a mixture comprising ethyl lactate, ethanol, H2SO4 and traces of water exits via the pipe (14), said crude ethyl lactate being purified by distillation under reduced pressure in the purification region (15). When the system is operating under stationary conditions, on the one hand the esterification is monitored by analyzing the degree of conversion and the yield of the esterification (by GC) and, on the other hand, the distillation is monitored by analyzing the binary mixture collected as top product from the column (5), which operates with a reflux ratio in the region of 0.27. The residence time is 6 hours. After the reactor has been replenished 4 times, i.e. operating for 30 hours (including the reaction time under batchwise conditions), a gas mixture having the following composition by weight (mean): 3.9percent of water, 96.1percent of ethanol, is present at the outlet of the column (5) and a mixture having the following composition by weight (mean): 2.2percent of water, 66.3percent of ethanol, 27.6percent of ethyl lactate, 1.3percent of dimer of ethyl lactate, is present at the outlet of the reactor (14). With sulfuric acid in water

T=80°C; Hide Experimental Procedure

Arkema,

Patent: US2006/41165 A1, 2006 ; Location in patent: Page/Page column 1-3 ; Title/Abstract Full Text Show Details

A lactic acid composition comprising 87percent by weight of lactic acid is esterified with the device as represented diagrammatically in FIG. 1. The distillation column (7) has a diameter of 70 cm and is filled with a Sulzer B.x.70 packing. It has 35 theoretical plates. Carrying Out the Test The following are introduced into the reactor (1): an 87percent lactic acid composition, absolute ethanol, 98percent sulfuric acid. The ethanol/lactic acid molar ratio is equal to 2.5. Esterification is carried out at 80° C. at atmospheric pressure. The progress of the reaction is monitored by quantitative determination of the lactic acid by GC. When the conversion of said lactic acid has reached 70percent, a mixture comprising: ethyl lactate, ethanol, lactic acid and water, is continuously extracted from the reactor (1). This mixture is subjected to flash separation in the column (5) at 85° C. under a pressure of 50 mbar. The top stream comprising: ethyl lactate, ethanol, lactic acid and water. This mixture is subjected to flash separation in the column (5). The top stream, comprising 44percent of ethanol, 42percent of ethyl lactate and 14percent of water, is subjected to fractional distillation in the column (7), which is fed with said top stream at the 13th theoretical plate. The fractional distillation is carried out at a column bottom temperature of 155° C. The top temperature is 77.2° C. The reflux ratio is set at 1.3. A mixture comprising (by weight) 76percent of ethanol, 24percent of water and traces of ethyl lactate (<0.3percent) is obtained as top product. Ethyl lactate exits as bottom product with a purity of greater than 94.6percent and comprising less than 1percent of water and less than 1percent of ethanol. This crude ethyl lactate is subjected to purification by fractional distillation under reduced pressure. With Nafion NR50

T=69.84°C; Kinetics; Further Variations:Catalysts;

Tagusagawa, Caio; Takagaki, Atsushi; Hayashi, Shigenobu; Domen, Kazunari

Journal of the American Chemical Society, 2008 , vol. 130, # 23 p. 7230 - 7231 Title/Abstract Full Text View citing articles Show Details

With mesoporous Nb3W7 oxide T=69.84°C; 2 h;

Tagusagawa, Caio; Takagaki, Atsushi; Iguchi, Ai; Takanabe, Kazuhiro; Kondo, Junko N.; Ebitani, Kohki; Hayashi, Shigenobu; Tatsumi, Takashi; Domen, Kazunari

Angewandte Chemie - International Edition, 2010 , vol. 49, # 6 p. 1128 - 1132 Title/Abstract Full Text View citing articles Show Details

With [TDTHP][Phosph]

T=40°C; Microwave irradiationEnzymatic reaction;

Major, Brigitta; Kelemen-Horvath, Ilona; Csanadi, Zsofia; Belafi-Bako, Katalin; Gubicza, Laszlo

Green Chemistry, 2009 , vol. 11, # 5 p. 614 - 616 Title/Abstract Full Text View citing articles Show Details

T=40°C; Fischer-Speier esterification method; 4 h; SonicationIonic liquid;

Li, Xinzhong; Lin, Qi; Ma, Liang

Ultrasonics Sonochemistry, 2010 , vol. 17, # 5 p. 752 - 755 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride

Reflux;

Rioz-Martinez, Ana; Cuetos, Anibal; Rodriguez, Cristina; De Gonzalo, Gonzalo; Lavandera, Ivan; Fraaije, Marco W.; Gotor, Vicente

Angewandte Chemie - International Edition, 2011 , vol. 50, # 36 p. 8387 - 8390 Title/Abstract Full Text View citing articles Show Details

With silica-supported sulfate T=100°C; 5 h;

Yang, Zhi-Wang; Niu, Leng-Yuan; Jia, Xiao-Jie; Kang, Qiao-Xiang; Ma, Zhen-Hong; Lei, Zi-Qiang

Catalysis Communications, 2011 , vol. 12, # 9 p. 798 - 802 Title/Abstract Full Text View citing articles Show Details

With 2.5K(1+)*0.5H(1+)*PW12O40(3-)=K2.5H0.5PW12O40 T=80°C; Inert atmosphere; SolventReagent/catalyst;

Vu, Thu Ha Thi; Au, Hang Thi; Nguyen, Thuy Ha Thi; Nguyen, Thu Trang Thi; Do, Manh Hung; Bui, Ngoc Quynh; Essayem, Nadine

Catalysis Letters, 2013 , vol. 143, # 9 p. 950 - 956 Title/Abstract Full Text View citing articles Show Details

With cation exchange resin 3 h; Reflux;

Zhang, Jie; Yang, Changchun; Tang, Ying; Xu, Lianghong; Wang, Xiaoting

Asian Journal of Chemistry, 2014 , vol. 26, # 15 p. 4827 - 4829 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 193795 Find similar reactions

46.5%

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With carbon dioxide

T=180°C; Sealed tubeGreen chemistry; Temperature;

Ren, Shoujie; Ye, X. Philip; Ayers, Paul D.

RSC Advances, 2015 , vol. 5, # 66 p. 53230 - 53239 Title/Abstract Full Text View citing articles Show Details

With sulfuric acid

T=100°C; bei pH 1 bis 1.4;

Smith; Claborn

Industrial and Engineering Chemistry, 1940 , vol. 32, p. 693 Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2434300 , 1945 ; Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2465772 , 1945 ; Full Text Show Details

Sealtest Inc.

Patent: US2390140 , 1944 ; Full Text Show Details

Sealtest Inc.

Patent: US2406648 , 1942 ; Full Text Show Details

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Rx-ID: 6395916 Find similar reactions

Losse,G.; Raue,H.

Chemische Berichte, 1965 , vol. 98, p. 1522 - 1530 Full Text View citing articles Show Details

Kabbe,H.-J.

Chemische Berichte, 1969 , vol. 102, p. 1404 - 1409 Full Text View citing articles Show Details

Achiwa

Tetrahedron Letters, 1977 , p. 3735 Full Text View citing articles Show Details

Verbiscar

Patent: US3742022 , 1971 ; Chem.Abstr., vol. 79, # 78433 Full Text Show Details

Bhattacharyya et al.

Journal of Applied Chemistry and Biotechnology, 1970 , vol. 20, p. 7 Full Text Show Details

Ito

Nippon Kagaku Zasshi, 1962 , vol. 83, p. 195 Chem.Abstr., 1963 , vol. 58, # 11264 Full Text Show Details

Hide Experimental Procedure

Monsanto Company

Patent: US4388102 A1, 1983 ; Title/Abstract Full Text Show Details

4:EXAMPLE 4

EXAMPLE 4 A reaction composition comprising 15.0 g (0.039 mole) tri-(1-ethoxycarbonylethyl)phosphite, 0.71 g (0.039 mole) water and 4.525 g (0.0131 mole) 1,3,5-tri-(ethoxycarbonylmethyl)hexahydro-1,3,5-triazine was heated to about 100°-110° C. for three hours with agitation. An alcohol co-product ethyl α-hydroxypropionate was removed by bulb to bulb distillation of the reaction mixture at 25° C. and 0.1 mmHg. The distillation residue was chromatographed on microcrystalline cellulose with an eluent of ethyl acetate.

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FUJIFILM Corporation

Patent: EP2141206 A1, 2010 ; Title/Abstract Full Text Show Details

Composition of Resist Liquid

Composition of Resist Liquid Propylene glycol monomethyl ether acetate (PGMEA): 19.20 parts by mass Ethyl lactate: 36.67 parts by mass Resin: 30.51 parts by mass Hide Details

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FUJIFILM Corporation; Iwato, Kaoru

Patent: US8956802 B2, 2015 ; Title/Abstract Full Text Show Details

Group a SL-1: Propylene glycol monomethyl ether acetate (PGMEA) SL-2: Propylene glycol monomethyl ether propionate SL-3: 2-Heptanone SL-4: Ethyl lactate SL-5: Propylene glycol monomethyl ether (PGME)

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FUJIFILM Corporation; Iwato, Kaoru; Takahashi, Hidenori; Shirakawa, Michihiro

Patent: US9140981 B2, 2015 ; Title/Abstract Full Text Show Details

The followings were prepared as the solvent. (Group a) SL-1: propylene glycol monomethyl ether acetate (PGMEA) SL-2: propylene glycol monomethyl ether propionate SL-3: 2-heptanone SL-4: ethyl lactate SL-5: propylene glycol monomethyl ether (PGME)

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Rx-ID: 33200664 Find similar reactions

47.5%

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With titanosilicate beads with hierarchical porosity (TiSil-HPB-60) T=105°C; 6 h;

Lin, Kaifeng; Li, Li; Sels, Bert F.; Jacobs, Pierre A.; Pescarmona, Paolo P.

Catalysis Today, 2011 , vol. 173, # 1 p. 89 - 94 Title/Abstract Full Text View citing articles Show Details

With 10 wtpercent Sn/deAl-β T=90°C; P=15001.5 Torr; AutoclaveInert atmosphere;

Hammond, Ceri; Conrad, Sabrina; Hermans, Ive

Angewandte Chemie - International Edition, 2012 , vol. 51, # 47 p. 11736 - 11739 Angew. Chem., 2012 , vol. 124, # 47 p. 11906 - 11909,4 Title/Abstract Full Text View citing articles Show Details

With Hf-TUD-1 mesoporous silicates T=90°C; 12 h; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

Li, Li; Cani, Damiano; Pescarmona, Paolo P.

Inorganica Chimica Acta, 2015 , vol. 431, p. 289 - 296 Title/Abstract Full Text View citing articles Show Details

2.3. Catalytic tests

Catalytic tests were carried out in a multiple-well parallel reactionblock [41]. In a typical test for the conversion of dihydroxyacetone(DHA) to ethyl lactate, a mixture of 1,3-dihydroxyacetonedimer (0.180 g, 2.00 103 mol) and decane (0.0215 g, 1.50 104mol, as GC internal standard) in 5 ml ethanol (3.92 g, as solventand reactant) was pre-heated at 45 C for 30 min to fully dissolvethe dimer and convert it into DHA. The selected amount of catalyst(50, 100 or 200 mg) was introduced into the pre-heated solution,the glass vial containing the reaction mixture was capped and thenstirred vigorously at 90 C for the selected reaction time. At the endof the test, the catalyst was separated by centrifugation and thereaction solution was analysed by gas chromatography (GC) on aTrace GC Ultra from Interscience (RTX-5 column, 5 m, 0.25 mm)[20]. The recyclability of the catalysts was evaluated by separatingthe solid from the reaction mixture by centrifugation at the end ofthe test. Next, the solid catalyst was washed five times with ethanoland dried overnight in an oven at 100 C. In an alternative recyclingapproach, after the five washings with ethanol the materialwas thermally treated in an oven at 300 C for 5 h in air (heatingrate: 1 C min1). The catalyst was then reused in a new test followingthe procedure described before. Leaching tests were performedby removing the catalyst (100 mg) after 30 min ofreaction: the sample was first centrifuged and then filteredthrough a 0.2 lm filter while at the reaction temperature. The filtratewas allowed to react for further 5 h 30 min. The conversionand product yields after 30 min and at the end of the hot filtrationtest were determined by GC analysis (vide supra) and compared.The catalytic tests for the synthesis of solketal were performedin tightly closed glass vials loaded with 25 mg of catalyst and asolution containing 0.921 g of highly purified glycerol (1.00 102mol) or 1.15 g of a mixture of 80 wt.percent glycerol and 20 wt.percent water(aqueous glycerol) (1.00 102 mol of glycerol), 0.581 or 1.162 gof acetone (1.00 102 or 2.00 102 mol), 0.132 g of 1,4 dioxane(1.50 103 mol, as internal standard) and 1.48 g of tert-butanol(2.00 102 mol, as solvent) [36]. The tests were carried out at80 C for 6 h with continuous and vigorous stirring. At the end ofthe test, the sample was centrifuged to separate the catalyst fromthe reaction solution, which was analysed on a Trace GC Ultra fromInterscience (PH POR-Q column, FT-3, 10 m, 0.25 mm).The acetalisation reaction of vanillin with propylene glycol wasperformed under vigorous stirring in a round bottom flaskequipped with a Dean–Stark apparatus to remove the waterformed during the reaction. Vanillin (250 mg, 1.64 103 mol)and propylene glycol (250 mg, 3.28 103 mol) were added to8 ml of toluene together with 19 mg of Sn-TUD-1 (7.5 wt.percent relativeto vanillin) and heated to 115 C [32]. After the desired reactiontime, the sample was allowed to cool down and centrifuged to separatethe catalyst from the reaction solution, which was analysedon a Trace GC Ultra (RTX-5 column, 5 m, 0.25 mm) with 1,4-dioxaneas internal standard added after the catalytic test.In all the studied reactions, he identity of the products was confirmedby gas chromatography-mass spectrometry (GC–MS) performedon an Agilent 6890 N gas chromatograph (WCOT fusedsilica column, 30 m, 0.25 mm) coupled with an Agilent 5973 MSDmass spectrometer. Hide Details With Snβ zeolite T=89.84°C; Hide Experimental Procedure

Dijkmans, Jan; Demol, Jan; Houthoofd, Kristof; Huang, Shuigen; Pontikes, Yiannis; Sels, Bert

Journal of Catalysis, 2015 , vol. 330, p. 545 - 557 Title/Abstract Full Text View citing articles Show Details

2.2. Catalytic tests

General procedure: For each reaction, aliquots of the sample were takenat regular time intervals through a rubber septum and werequantitatively analyzed with an Agilent 6850 GC, equipped witha HP-1 column and FID detector. For non-volatile products, anAgilent 1200 series HPLC equipped with Metacarb 67C columnand RI detector was used. Identification of the products was basedon retention time analysis and confirmed by GC–MS (Agilent 6890GC with HP5-MS column and Agilent 5973 Mass SelectiveDetector). TOFs were calculated as moleproduct moleSn1 h1, whileSTY was determined as gproduct gcatalyst1 h1. Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

T=100°C; Molecular sieve;

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Rx-ID: 41586833 Find similar reactions

With molybdenum(VI) oxide

T=100°C; Molecular sieve;

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Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41586834 Find similar reactions

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With molybdenum(VI) oxide

T=100°C; Molecular sieve;

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Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41586835 Find similar reactions

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With molybdenum(VI) oxide

T=100°C; Molecular sieve;

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Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41586836 Find similar reactions

With molybdenum(VI) oxide

T=100°C; Molecular sieve;

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Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41586838 Find similar reactions

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With molybdenum(VI) oxide

T=100°C; Molecular sieve;

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Orazov, Marat; Davis, Mark E.

Proceedings of the National Academy of Sciences of the United States of America, 2015 , vol. 112, # 38 p. 11777 - 11782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31531303 Find similar reactions

26%

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Li, Li; Collard, Xavier; Bertrand, Arnaud; Sels, Bert F.; Pescarmona, Paolo P.; Aprile, Carmela

Journal of Catalysis, 2014 , vol. 314, p. 56 - 65 Title/Abstract Full Text View citing articles Show Details

Stage #1: T=45°C; 0.5 h; Stage #2: With silylated extra-small mesoporous Sn-silicate MCM41-A nanoparticles T=20 - 90°C; Hide Experimental Procedure

2.4 Catalytic tests

General procedure: The catalytic reactions were carried out in a multiple-well parallel reaction block [14]. In a typical experiment for the conversion of dihydroxyacetone (DHA) to ethyl lactate, 0.180 g of DHA (2.00 × 10−3 mol, in the form of 1,3-dihydroxyacetone dimer) and 0.0215 g of decane (1.50 × 10−4 mol, as GC internal standard) were dissolved in 3.92 g ethanol (as solvent and reactant) at 45 °C for 30 min. Then, the selected amount of catalyst (50, 100 or 200 mg) was added to the solution at room temperature. This reaction mixture was heated at 90 °C under vigorous stirring (1200 rpm) for the selected reaction time. At the end of the test, the catalyst was separated by centrifugation and the solution was analyzed by gas chromatography (GC) on a Trace GC Ultra from Interscience; more details about the GC analyses can be found in previous reports [14]. Recyclability tests were performed by separating the catalyst from the reaction mixture by centrifugation followed by washing with ethanol. The washing procedure was repeated five times. Finally, the catalyst was dried overnight at 100 °C. Alternative approaches involved a calcination step for 2 h (either at 300 °C or at 500 °C, with a heating rate of 2 °C min−1) after the washing step. 21.8%

T=80°C; 8 h;

Zhang, Zehui; Zhao, Zongbao

Chinese Journal of Catalysis, 2011 , vol. 32, # 1 p. 70 - 73 Title/Abstract Full Text Show Details

12 %Spectr.

With gallosilicate mesoporous materials-41, Ga-MCM-41 T=20 - 90°C; 6 h; Green chemistry; Catalytic behavior; Hide Experimental Procedure

Collard, Xavier; Li, Li; Lueangchaichaweng, Warunee; Bertrand, Arnaud; Aprile, Carmela; Pescarmona, Paolo P.

Catalysis Today, 2014 , vol. 235, p. 184 - 192 Title/Abstract Full Text View citing articles Show Details

2.4. Catalytic tests

For the conversion of dihydroxyacetone (DHA) to ethyl lac-tate, 0.180 g of DHA (2 mmol, in the form of 1,3-dihydroxyacetonedimer) and 0.0215 g of decane (0.15 mmol, as GC internal standard)were dissolved in 3.92 g of ethanol (as solvent and reactant) at 45Cfor 30 min. Next, 50 mg of catalyst were added to the solution atroom temperature. The reaction mixture was heated to 90C for6 h under vigorous stirring (1200 rpm). The tests were carried outin the same 50-well reaction block used for the reaction of glycerolwith acetone. At the end of the test, the catalyst was separated bycentrifugation and the reaction solution was analyzed by gas chromatography (GC) on a Trace GC Ultra from Interscience equippedwith an RTX-5 fused silica column (5 m; 0.1 mm). Recyclabilitytests were performed by separating the catalyst from the reactionmixture by centrifugation followed by washing with ethanol (fivetimes). Next, the catalyst was dried overnight at 100C and reusedin a new catalytic run. Before the last reuse, the catalysts were cal-cined at 500C for 2 h (heating rate of 2C min−1). The leaching tests were carried out with the same protocol employed for the reactionof glycerol with acetone (vide supra). A

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With TiO2-doped zirconia in ethanol

T=140°C; P=7500.75 Torr; Inert atmosphereFlow reactor; Reagent/catalystTemperatureTime; Hide Experimental Procedure

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Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

General procedure: The process was also studied in a flow regime using a fixed bed reactor. As rule, 2 cm3 of a granulated (0.5–1 mm) catalyst was placed into a steel reactor (d=8 mm). The catalyst was trained at 120 °C for 1h in Ar flow. Feed rate was varied in 2–10 mmol C3H6O3/gcat/h interval (LHSV=2.2–0.9 h−1) using a Waters-590 pump. The experiments were performed in Ar flow (15 cm3/min) at 1.0 MPa preventing liquid to gaseous phase transfer. A

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With zirconia doped with silica in ethanol

T=130°C; P=7500.75 Torr; 2 h; Autoclave; Reagent/catalystTime; Hide Experimental Procedure

Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

2.2 Catalytic experiments

General procedure: 8 wt.percent solution of dihydroxyacetone (>98percent, Merk) in anhydrous ethanol was used as a reaction mixture. The experiments were carried out in a rotated autoclave (60 rpm) at 100–160 °C for 2 h. Usually, 0.5 g of dihydroxyacetone, 5.6 g of ethanol and 0.3 g (5 wt.percent) of a catalyst were placed into a 25 ml teflon can. A

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Rx-ID: 37314688 Find similar reactions

With TiO2-doped zirconia in ethanol

T=150°C; P=7500.75 Torr; 2 h; Autoclave; Reagent/catalystTime; Hide Experimental Procedure

Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

2.2 Catalytic experiments

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Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

With zirconia doped with silica in ethanol

T=140°C; P=7500.75 Torr; Inert atmosphereFlow reactor; Hide Experimental Procedure

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Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

With zirconia doped with silica in ethanol

T=140°C; P=7500.75 Torr; 2 h; Autoclave; Hide Experimental Procedure

2.2 Catalytic experiments

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Rx-ID: 37314691 Find similar reactions

With TiO2-doped zirconia in ethanol

T=140°C; P=7500.75 Torr; 2 h; Autoclave; Hide Experimental Procedure

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Mylin, Artur M.; Levytska, Svitlana. I.; Sharanda, Mykhailo E.; Brei, Volodymyr V.

Catalysis Communications, 2014 , vol. 47, p. 36 - 39 Title/Abstract Full Text View citing articles Show Details

2.2 Catalytic experiments

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Rx-ID: 38198767 Find similar reactions

A: 34% B: 16%

Stage #1: T=45°C; 0.5 h; Stage #2: With extra-small mesoporous Sn-silicate MCM-41-F nanoparticles T=20 - 90°C; Catalytic behavior; Reagent/catalystTime; Hide Experimental Procedure

Li, Li; Collard, Xavier; Bertrand, Arnaud; Sels, Bert F.; Pescarmona, Paolo P.; Aprile, Carmela

Journal of Catalysis, 2014 , vol. 314, p. 56 - 65 Title/Abstract Full Text View citing articles Show Details

2.4 Catalytic tests

Stage #1: T=45°C; 0.5 h; Stage #2: With extra-small mesoporous Sn-silicate MCM-41-E nanoparticles T=20 - 90°C; Catalytic behavior; Hide Experimental Procedure

Li, Li; Collard, Xavier; Bertrand, Arnaud; Sels, Bert F.; Pescarmona, Paolo P.; Aprile, Carmela

Journal of Catalysis, 2014 , vol. 314, p. 56 - 65 Title/Abstract Full Text View citing articles Show Details

2.4 Catalytic tests

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Rx-ID: 38198768 Find similar reactions

A: 44% B: 5% C: 15%

Stage #1: T=45°C; 0.5 h; Stage #2: With extra-small mesoporous Sn-silicate MCM-41-A nanoparticles T=20 - 90°C; Catalytic behavior; Reagent/catalystTime; Hide Experimental Procedure

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Li, Li; Collard, Xavier; Bertrand, Arnaud; Sels, Bert F.; Pescarmona, Paolo P.; Aprile, Carmela

Journal of Catalysis, 2014 , vol. 314, p. 56 - 65 Title/Abstract Full Text View citing articles Show Details

2.4 Catalytic tests

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Rx-ID: 35215181 Find similar reactions

90%

With magnesium oxide; sodium hydroxide

T=160°C; P=30402 Torr; 5 h; Inert atmosphere; Hide Experimental Procedure

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LG Chem, Ltd.; Yoon, Sung-Cheol; Park, Seung-Young; Lee, In-Su

Patent: US2013/79547 A1, 2013 ; Location in patent: Paragraph 0067; 0068 ; Title/Abstract Full Text Show Details

7:Preparation of Ethyl Lactate Using MgO

Example 7 Preparation of Ethyl Lactate Using MgO Glycerol (1 g), ethanol (5 g), and MgO (0.2 g) and NaOH (0.5 g) as catalyst were introduced into a 200 mL high pressure reactor under Ar atmosphere, and reacted 160° C. and 40 atm for 5 hours. And then, the reaction mixture was cooled to room temperature, and ethyl lactate was separated by fractional distillation and obtained with 90percent yield. 1H NMR (CDCl ): δ 4.3 (q), 4.19 (q), 2.89 (br s), 1.42 (d), 1.33 (t) 3 A

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Rx-ID: 36232480 Find similar reactions

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MYRIANT CORPORATION; OZMERAL, A., Cenan; GLAS, Joseph P.; DASARI, Rajesh; TANIELYAN, Setrak; BHAGAT, Ramesh Deoram; KASIREDDY, Mohan Reddy; SINGH, Ramnik; GNANADESIKAN, Vijay; AUGUSTINE, Robert L.; MORE, Santosh

Patent: WO2013/134385 A1, 2013 ; Location in patent: Paragraph 0152; 0153 ;

With Na3/K-L-type zeolite in water

T=340°C; 4 h; Hide Experimental Procedure

Title/Abstract Full Text Show Details

[0152]Dehydroxylation of Lactic Acid in a Solvent — Solvent Effect. A starting composition as listed in Table 12 was reacted in the vapor phase with a Na3/K-L-type zeolite, according to Reaction Protocol III above, for 4 hours at 340°C.[0153]As shown in Table 12, a Na3/K-L-type zeolite does catalyze esterificationreactions. Further, the addition of an alcohol in the starting composition appears to haveeffect on the conversion but does dramatically reduce the selectivity to acrylic acid.

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Rx-ID: 36430027 Find similar reactions

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With amberlyst wet 15 T=130°C;

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Van Wouwe, Pieter; Dusselier, Michiel; Basic, Aurelie; Sels, Bert F.

Green Chemistry, 2013 , vol. 15, # 10 p. 2817 - 2824 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 34373935 Find similar reactions

T=200°C; P=18389.3 - 58845.8 Torr; 8 h; Product distribution /

COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

Patent: US2012/296110 A1, 2012 ; Location in patent: Page/Page column 6 ;

selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

100 g calcium lactate (10 wt percent) solution (1) and ethanol (2) was charged in mild steel high pressure reactor vessel (4) having capacity of 5 L and continuously stirred at speed of agitation ranging from 300, 600 and 1000 RPM using agitator. Carbon dioxide gas from cylinder (3) was pressurized in reactor so as to get initial pressure 25 Kg/cm2. Reaction material was then allowed to heat till 200° C. and was maintained at this temperature for 8 hour. During operation pressure inside reactor goes up to 72-80 Kg/cm2. Reaction mass was then allowed to cool till 25° C. and the reaction mixture was filtered on the basket centrifuge (5) at 3000 RPM. The wet cake (6) obtained from centrifuge; containing calcium carbonate was allowed to dry in oven (7) at 110° C. and stored (8). The filtrate (9) collected from centrifuge was analyzed for ethyl ester, ethanol contents using Shimadzu made GC-MS Model-QP5000 where as the moisture was measured by Automatic Karl-Fischer, Lab India made instrument. The concentration profile of ethyl ester during the reaction was shown in Table 1. The average moisture content at the end of the reaction was found in the range of 7.5percent by wt.

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Rx-ID: 31063368 Find similar reactions

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GALACTIC SA

Patent: US2011/160480 A1, 2011 ; Location in patent: Page/Page column 3 ;

T=130°C; P=206.271 Torr; 8 h; Hide Experimental Procedure

Title/Abstract Full Text Show Details

A charge consisting of 500 kg of lactic acid with a 100percent concentration by weight is first introduced into the esterification reactor with a capacity of 9 m3. The product is agitated and heated at 100° C. under a reduced pressure of 27.5 kPa absolute.When the lactic acid is at the correct temperature, 165.5 kg/h of anhydrous ethanol and 100 kg/h of 100percent lactic acid is introduced continuously, equivalent to an ethanol/lactic acid mol ratio of 3.6:1. Esterification takes place at 130° C., at a reduced pressure of 27.5 kPa absolute.Part of the ethanol reacts with the lactic acid in order to produce ethyl lactate and water, and the other part is used as a stripping agent for promoting extraction of the volatiles from the reaction medium. This therefore means that the esterification reaction takes place in an excess of lactic acid in the reactor.The volatile phase comprising water, ethanol, ethyl lactate and traces of lactic acid is extracted continuously from the reaction medium. The temperature of these vapours is 120° C. This mixture has an acidity of less than or equal to 0.2percent (equivalent to 100percent ethyl lactate).This gaseous phase is injected continuously into a first distillation column, where it undergoes distillation under reduced pressure (27.5 kPa absolute). The column works at a reflux level of 2. A first fraction collected at the head, at a temperature of 70° C., is composed of:47percent ethanol,21percent water,32percent ethyl lactate.The fraction at the bottom of the column is collected at a temperature of 137° C. and consists of 10percent lactic acid and 90percent ethyl lactate. This mixture is recycled to the esterification reactor.The fraction collected at the top of the first column is then injected in liquid form into a second distillation column in order to purify the ester. This column works at a pressure of 10 kPa absolute and a reflux level of 0.2. The purified ester is collected at the bottom of the column at a temperature of 82° C. and is composed of ethyl lactate with a purity greater than 97percent. The ethanol/water mixture is recovered at the top of the column at a temperature of 30° C.The change in composition of the ethyl lactate collected in the boiler at the bottom of the second column is set out in the following table: Phase of starting columns and being brought up to full operation Ethyl Water Ethanol lactate content Acidity Colour content content Time (percent) (percent) (Hazen) (percent) (percent) 5 hours 0.12 0.04 5 0.2 99.64 8 hours 0.08 0.02 13 0.1 99.88 10 hours 0.06 0.05 9 0.5 99.39 24 hours 0.1 0.06 5 0.3 99.54 2 days 0.08 0.01 12 0.1 99.81 3 days (*) 0.05 0.07 9 0.4 99.48 3 days 0.05 0.09 18 0.4 99.46 4 days 0.11 0.05 11 0.2 99.64 (*) Sample taken off directly at the lining output rather than in the boiler. A

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With 5 platinum on alumina; hydrogen in toluene

T=20°C; P=750.075 Torr;

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Balazsik, Katalin; Szori, Kornel; Szollosi, Gyoergy; Bartok, Mihaly

Catalysis Communications, 2011 , vol. 12, # 15 p. 1410 - 1414 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33524920 Find similar reactions

With 5 platinum on alumina; hydrogen in toluene

T=20°C; P=750.075 Torr;

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Balazsik, Katalin; Szori, Kornel; Szollosi, Gyoergy; Bartok, Mihaly

Catalysis Communications, 2011 , vol. 12, # 15 p. 1410 - 1414 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33524923 Find similar reactions

With 5 platinum on alumina; hydrogen in toluene

T=20°C; P=750.075 Torr;

Balazsik, Katalin; Szori, Kornel; Szollosi, Gyoergy; Bartok, Mihaly

Catalysis Communications, 2011 , vol. 12, # 15 p. 1410 - 1414 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29363402 Find similar reactions

A: 39% B: 16%

With Sn-BEA T=160°C; 20 h; Inert atmosphereautoclave; Hide Experimental Procedure

Haldor Topsoe A/S

Patent: EP2184270 A1, 2010 ; Location in patent: Page/Page column 6 ; Title/Abstract Full Text Show Details

11:

An autoclave (50 cc microclave) is charged with 8.0 g of ethanol, 0.2252 g of sucrose (0.6578 mmol), 118.9 mg naphthalene (internal standard) and finally with 160.0 mg Sn-BEA (prepared according to US-pat 6.306.364). The autoclave is closed, charged with 20 bar of argon and heated to 160°C. After the temperature reaches 100°C, the mechanical stirrer is started (500 rpm) and the mixture is heated for 20 hours under these conditions. GC-analysis of the reaction mixture shows that 1.03 mmol of ethyl lactate is formed (39 percent) together with 0.316 mmol ethyl 2-hydroxy-3-butenoate (16 percent). A: 30% B: 16%

With Sn-BEA T=160°C; P=15001.5 Torr; Inert atmosphere of argon; Hide Experimental Procedure

Taarning, Esben; Shunmugavel, Saravanamurugan; Holm, Martin Spangsberg

Patent: US2010/121096 A1, 2010 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

11:

An autoclave (50 cc microclave) is charged with 8.0 g of ethanol, 0.2252 g of sucrose (0.6578 mmol), 118.9 mg naphthalene (internal standard) and finally with 160.0 mg Sn-BEA (prepared according to U.S. Pat. No. 6,306,364). The autoclave is closed, charged with 20 bar of argon and heated to 160° C. After the temperature reaches 100° C., the mechanical stirrer is started (500 rpm) and the mixture is heated for 20 hours under these conditions. GC-analysis of the reaction mixture shows that 1.03 mmol of ethyl lactate is formed (39percent) together with 0.316 mmol ethyl 2-hydroxy-3-butenoate (16percent).

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Rx-ID: 29590806 Find similar reactions

76 %Chromat.

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Pescarmona, Paolo P.; Janssen, Kris P. F.; Delaet, Chloe; Stroobants, Christophe; Houthoofd, Kristof; Philippaerts, An; De Jonghe, Chantal; Paul, Johan S.; Jacobs, Pierre A.; Sels, Bert F.

Green Chemistry, 2010 , vol. 12, # 6 p. 1083 - 1089 Title/Abstract Full Text View citing articles Show Details

With Zeolite USY CBV 600 T=109.84°C; 4 h; Autoclave;

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Rx-ID: 29590807 Find similar reactions

33 %Chromat.

With Zeolite USY CBV 600 in water

T=89.84°C; 1.5 h;

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Pescarmona, Paolo P.; Janssen, Kris P. F.; Delaet, Chloe; Stroobants, Christophe; Houthoofd, Kristof; Philippaerts, An; De Jonghe, Chantal; Paul, Johan S.; Jacobs, Pierre A.; Sels, Bert F.

Green Chemistry, 2010 , vol. 12, # 6 p. 1083 - 1089 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10327371 Find similar reactions

With sodium hydride

T=80°C;

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Guo, MaoJun; Varady, Laszlo; Fokas, Demosthenes; Baldino, Carmen; Yu, Libing

Tetrahedron Letters, 2006 , vol. 47, # 23 p. 3889 - 3892 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 23660368 Find similar reactions

44.14%

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Board of Trustees of Michigan State University

Patent: US2006/14977 A1, 2006 ; Location in patent: Page/Page column 6; 7; 8-10 ;

T=25 - 82°C; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

11; 12; 17; 18; 19; 20; 21; 22; 23; 24; 25; 26; 27; 28; 29; 30; 31; 32; 33; 34; 35; 36; 37; 38; 39; 40:

EXAMPLES 11 AND 12; Trans-esterification of methyl lactate to ethyl lactate: The ability to produce methyl lactate straightforwardly by reactive distillation opens an additional pathway to lactate ester formation-that of transesterification. The advantage of transesterification reactions is that there is no water produced or required in the system, thus hydrolysis of the esters is not a concern. To explore this route, several transesterification experiments were conducted in the lab scale reactive distillation column. In transesterification, methyl lactate was fed at the top of the column reactive zone and ethanol is fed at the bottom of the reactive zone. Ethanol moved up the distillation column and reacted with methyl lactate to give ethyl lactate and methanol. All methanol and excess ethanol exited at the top of the column, and ethyl lactate, unreacted methyl lactate, and a small quantity of ethanol were removed continuously from the reboiler. Results of the transesterification of methyl lactate to ethyl lactate are shown in Table 3 in Examples 11 and 12 (Example 12 is in FIG. 3). A methyl lactate conversion of 94percent was achieved with an ethyl lactate purity in the bottoms stream exceeding 90percent by weight. Thus it is clear that transesterification is a viable method for producing a family of organic acid esters from a single parent ester. In a larger column complete transesterification will take place with pure product formation.; EXAMPLES 17 AND 18; Pilot-Scale Experiments and Simulation Pilot-scale reactive distillation studies were conducted for the production of ethyl lactate. The column was configured such that the stripping zone constitutes the bottom 0.7 m of the column while the rectifying occupied the top 0.9 m below the condenser. The reactive zone thus made up the center 2.9 meters of the column. The column was assumed to contain a total of equilibrium 10 stages including reboiler and condenser. Lactic acid solution (58 wt percent monomer) was fed at the 2nd stage (0.3 m below condenser) and absolute ethanol was fed at the 9th stage (0.3 m above reboiler); both feeds were at room temperature (298° K). As with the bench-scale column, a reflux ratio of zero was found to give the best overall conversion of lactic acid to ethyl lactate. Following several shakedown runs, a set of conditions were identified that give 81percent lactic acid conversion to ethyl lactate. This value is similar to the conversion obtained after limited optimization in the bench-scale column. With further optimization of the pilot-scale column (see results of simulation below) conversions exceeding those in the bench-scale column can be achieved. The pilot-scale reactive distillation column was simulated at reaction conditions and using the experimental reaction equilibrium data obtained in the laboratory scale column. The equilibrium stage model with an HETP of 0.6 m was used for the simulation. A comparison of the experimental and simulated results is given in Table 6 (Examples 17 and 18) below; there is reasonably good agreement between the product stream compositions and overall lactic acid conversion. Temperatures and stage-by-stage compositions for both simulations and experiments are given in FIGS. 4 and 5, respectively.; EXAMPLES 19 TO 40; In the following Examples 19 to 40 the pilot-scale column was operated as shown in Table 7. The column configuration in Table 7 is compared to the bench scale apparatus. The results are shown in Tables 8, 9 and 10. A

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Rx-ID: 9892806 Find similar reactions

B: 79%

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Byung, Tae Cho; Sang, Kyu Kang

Tetrahedron, 2005 , vol. 61, # 24 p. 5725 - 5734 Title/Abstract Full Text View citing articles Show Details

Stage #1: T=25°C; 0.166667 h; Stage #2: With sodium tetrahydroborate; boric acid

T=25°C; 0.25 h;

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Rx-ID: 9896903 Find similar reactions

B: 71%

Byung, Tae Cho; Sang, Kyu Kang

Tetrahedron, 2005 , vol. 61, # 24 p. 5725 - 5734 Title/Abstract Full Text View citing articles Show Details

Stage #1: T=25°C; 0.166667 h; Stage #2: With sodium tetrahydroborate; boric acid

T=25°C; 0.5 h;

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Synthesize Find similar Rx-ID: 9934236 Find similar reactions

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A: 52% B: 38%

in tetrahydrofuran

T=-10°C; 1 h;

DiMauro, Erin F.; Kozlowski, Marisa C.

Journal of the American Chemical Society, 2002 , vol. 124, # 43 p. 12668 - 12669 Title/Abstract Full Text View citing articles Show Details

A: 52 % Spectr. B: 38 % Spectr.

in tetrahydrofuran

T=-10°C;

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.

Tetrahedron, 2005 , vol. 61, # 26 p. 6249 - 6265 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10226824 Find similar reactions

A: 88 % Chromat.

With tin(IV) chloride

T=90°C; 1 h;

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Hayashi, Yukiko; Sasaki, Yoshiyuki

Chemical Communications, 2005 , # 21 p. 2716 - 2718 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10235786 Find similar reactions

A: 74 % Chromat.

With tin(ll) chloride

T=90°C; 3 h;

Hayashi, Yukiko; Sasaki, Yoshiyuki

Chemical Communications, 2005 , # 21 p. 2716 - 2718 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 23489050 Find similar reactions

A: 87% B: 11%

With aluminium trifluoromethanesulphonate in iso-tridecanol; diisopropyl ether; water

T=62 - 90°C; P=150.015 - 7500.75 Torr; 10 - 12 h; Conversion of starting material; Hide Experimental Procedure

SASOL GERMANY GMBH

Patent: WO2005/49556 A2, 2005 ; Location in patent: Page/Page column 9-10 ; Title/Abstract Full Text Show Details

B1; B2:

563.0 g of lactic acid (80 percent by weight in water, i. e. based on lactic acid and used as an 80 percent by weight solution in water), 460.7 g of ethanol and 2.3 g Al (OTf) 3 (in 9 g of isotridecanol, based on Al (OTf) 3 and used as a 20 percent by weight solution in isotridecanol), were introduced into a reaction flask. The water separator was filled with diisopropyl ether which served as entrainer. A further 300 g of diisopropyl ether were introduced into the flask. The bottom was heated to 80 to90 C such that a good reflux was formed and forming water was removed azeotropically at a head temperature of62 C. The course of the reaction was monitored by way of the acid number. The esterification was carried out up to an acid number of < 2 mg KOH/g. This was reached after 12 h, whereby a conversion of more than 99 percent had been reached for the hydroxycarboxylic acid. The yield of ethyl lactate was more than 88 percent. The di-lactic acid ethyl ester was formed in a yield of 11 percent. The crude product was neutralised with Ca (OH) 2 to remove the residual acid and the catalyst and filtered. The entrainer and excess alcohol were removed by distillation from the filtrate and the crude product was subjected to fractional distillation at reduced pressure.; 563.0 g of lactic acid (80 percent by weight in water) were introduced into a reaction flask and part of the water was removed at reduced pressure at elevated temperature within 30 min such that the lactic acid was present as an approximately 95 percent solution. 460.7 g of ethanol and 2., 3 gof Al (OTf) 3 (in 9 g of isotridecanol) were added. The water separator was filled with diisopropyl ether which served as entrainer. A further 300 g of diisopropyl ether were introduced into the flask and the bottom was heated to 80 to90 C such that a good reflux was formed and the water generated was removed azeotropically at a head temperature of62 C. The course of the reaction was monitored by way of the acid number. The esterification was carried out up to an acid number of less than 2 mg KOH/g. This, including drying of the lactic acid, was achieved after 9.5 h. The conversion of lactic acid was more than 99 percent. The yield of ethyl lactate was more than 87 percent, the dilactic acid ethyl ester was formed in a 12 percent yield. The work-up of the crude product was carried our in a manner analogous to exampleB 1.

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With potassium hydrogensulfate in methanol

T=20°C; 3 h;

Rx-ID: 9793451 Find similar reactions

Arumugam, Pandurangan; Karthikeyan, Ganesan; Perumal, Paramasivan T.

Chemistry Letters, 2004 , vol. 33, # 9 p. 1146 - 1147 Title/Abstract Full Text View citing articles Show Details

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A: 86.6%

With ethanol; sulfuric acid

T=75°C; 1 h; Hide Experimental Procedure

ARCHER-DANIELS-MIDLAND COMPANY

Patent: EP1206435 B1, 2004 ; Location in patent: Page column 9 ; Title/Abstract Full Text Show Details

5:Example 5

17.5 g of the spray dried calcium lactate was slurried into 125 ml of anhydrous ethanol. 4.9 ml of concentrated sulfuric acid was added over 30 minutes. The slurry was allowed to heat to 75 C with stirring for one hour. The slurry was filtered and washed two times with 100 ml of ethanol. The filtrate of 200 ml contained 67.9 g/L ethyl lactate and 1.6 g/L lactic acid for a total yield of 86.6percent. A

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Rx-ID: 2511816 Find similar reactions

With tris(phenanthroline)iron(III) tris(hexafluorophosphate) in acetonitrile

T=24.9°C; Rate constant;

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Fukuzumi, Shonichi; Tokuda, Yoshihiro; Kitano, Toshiaki; Okamoto, Toshihiko; Otera, Junzo

Journal of the American Chemical Society, 1993 , vol. 115, # 20 p. 8960 - 8968 Title/Abstract Full Text View citing articles Show Details

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A: 62.3%

Hide Experimental Procedure

Rx-ID: 25414379 Find similar reactions

BP Chemicals Limited

Patent: EP460831 A2, 1991 ; Title/Abstract Full Text Show Details

5:Example 5

Example 5 A solution was made up containing 20ml ethanol, 4g dihydroxyacetone, 1.18g chromium trichloride hexahydrate and 5.84g of diethylene glycol dimethyl ether. Some warming was required in order to dissolve all of the dihydroxyacetone. The solution was heated to 115°C in a pressure vessel for 16.5 hours. After cooling to ambient temperature and pressure it was analyzed for ethyl lactate and lactic acid by HPLC. The yield of ethyl lactate was 62.3percent and the yield of lactic acid was 13.3percent.

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With sodium thiosulfate in methanol; water

1 h;

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Rx-ID: 2291159 Find similar reactions

Isayama, Shigeru

Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 5 p. 1305 - 1310 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 90 percent / 10percent hydrochloric acid, methanol / 0.5 h / Ambient temperature 2: 96 percent / Na2S2O3 / methanol; H2O / 1 h View Scheme

Rx-ID: 21868776 Find similar reactions

Isayama, Shigeru

Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 5 p. 1305 - 1310 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 2537585 Find similar reactions

A: 100%

With methylammmonium fluoride in methanol

T=20°C; 24 h; further solvents (CH3CN/THF, THF, dioxane), other temperature;

Solladie-Cavallo, A.; Khiar, N.

Synthetic Communications, 1989 , vol. 19, # 7,8 p. 1335 - 1340 Title/Abstract Full Text Show Details

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A: 90%

With methylammmonium fluoride in methanol

24 h; Heatingfurther solvents (CH3CN/THF, THF, dioxane), other temperature;

Solladie-Cavallo, A.; Khiar, N.

Synthetic Communications, 1989 , vol. 19, # 7,8 p. 1335 - 1340 Title/Abstract Full Text Show Details

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Rx-ID: 1548488 Find similar reactions

With anhydrous magnesium perchlorate in acetonitrile

T=39°C; 24 h; intermolecular hydride transfer, var. conc. of Mg(ClO4) and pyruvate; Rate constantProduct distribution;

Kirby, Anthony J.; Walwyn, David R.

Gazzetta Chimica Italiana, 1987 , vol. 117, # 11 p. 667 - 680 Title/Abstract Full Text Show Details

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Rx-ID: 25039122 Find similar reactions

B: 1.18 g (53%)

in N,N-dimethyl-formamide

Hide Experimental Procedure

The Regents of the University of California

Patent: US4675325 A1, 1987 ; Title/Abstract Full Text Show Details

III.b:Formation of Ethyl 2(R)-(t-butylidiphenylsilyloxy)propanoate (15) Filtration and concentration of the filtrate gave crude ethyl D-lactate, which was immediately silylated at 23° C. (6 h) in DMF (10 mL) with t-butyldiphenylsilyl chloride (1.8 mL, 7.0 mmol) and imidazole (950 mg, 14 mmol). Aqueous workup (ether, MgSO4) gave a viscous oil which was chromatographed (7:1 hexane-ethyl acetate) to give 1.18 g (53percent) of pure 15 as a colorless liquid: [a]D25 +46.0 (c 1.97, EtOH), IR (film) 1762, 1110, 1140 cm-1; 1 H NMR (250 MHz, CDCl3) 7.3-7.7 (m, Ph), 4.27 (q, J=6.7 Hz, OCH), 4.02 (q, J=7.1 Hz, OCH2), 1.37 (d, J=6.7 Hz, CHMe, 1.14 (t, J=7.1 Hz, CH2 Me), 1.10 (s, t-Bu); MS (EI) m/z 299.1104 (299.1103 calcd for C17 H19 SiO3, M-Bu, 72percent), 227 (70percent), 199 (100percent).

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With bromo-1,3,2-benzodioxaborole in dichloromethane

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Rx-ID: 2650812 Find similar reactions

Boeckman, Robert K.; Potenza, Joan C.

18 h; Ambient temperature;

Tetrahedron Letters, 1985 , vol. 26, # 11 p. 1411 - 1414 Title/Abstract Full Text Show Details

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A: 35% B: 15%

With oxygen in N,N-dimethyl-formamide

T=20°C; electrolysis;

Sugawara, M.; Baizer, M. M.; Monte, W. T.; Little, R. D.; Hess, U.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983 , vol. 37, # 6 p. 509 - 518 Title/Abstract Full Text Show Details

A: 35% B: 15%

With oxygen in N,N-dimethyl-formamide

T=20°C; electrolysis;

Sugawara, M.; Baizer, M. M.; Monte, W. T.; Little, R. D.; Hess, U.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983 , vol. 37, # 6 p. 509 - 518 Title/Abstract Full Text Show Details

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With titanium tetraethoxide in ethanol

T=78°C; 6 h;

Rx-ID: 2533339 Find similar reactions

Seebach, Dieter; Hungerbuehler, Ernst; Naef, Reto; Schnurrenberger, Peter; Weidmann, Beat; Zueger, Max

Synthesis, 1982 , # 2 p. 138 - 141 Title/Abstract Full Text Show Details

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B: 60%

Becker, Hans-Dieter; Ruge, Bernd

Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2189 - 2195 Title/Abstract Full Text View citing articles Show Details

in ethanol; chloroform

T=12 - 20°C; 1 h;

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Rx-ID: 6679977 Find similar reactions

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Troupe; Dimilla

Industrial and Engineering Chemistry, 1957 , vol. 49, p. 847 Full Text Show Details

T=25 - 100°C; Equilibrium constant;

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Rx-ID: 6679978 Find similar reactions

T=25 - 100°C; Equilibrium constant;

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Troupe; Dimilla

Industrial and Engineering Chemistry, 1957 , vol. 49, p. 847 Full Text Show Details

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Rx-ID: 793870 Find similar reactions

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T=150°C;

Chemische Berichte, 1954 , vol. 87, p. 531,534 Chemische Berichte, 1956 , vol. 89, p. 1532 Full Text Show Details

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Rx-ID: 636319 Find similar reactions

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With 1,4-dioxane; sodium hydroxide

anschliessend mit Aethanol unter Einleiten von Chlorwasserstoff;

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Henze; Leslie

Journal of Organic Chemistry, 1950 , vol. 15, p. 901,903 Full Text Show Details

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Rx-ID: 193783 Find similar reactions

With sulfuric acid

T=100°C; bei pH 1 bis 1.4;

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Smith; Claborn

Industrial and Engineering Chemistry, 1940 , vol. 32, p. 693 Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2434300 , 1945 ; Full Text Show Details

Nation.Dairy Research Labor.

Patent: US2465772 , 1945 ; Full Text Show Details

Sealtest Inc.

Patent: US2390140 , 1944 ; Full Text Show Details

Sealtest Inc.

Patent: US2406648 , 1942 ; Full Text Show Details

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With sulfuric acid

T=100°C; unter Abdestillieren des Aethyllactats mit Aethanol;

Rx-ID: 6395917 Find similar reactions

Comm.Solv.Corp.

Patent: US2029694 , 1934 ; Full Text Show Details

Higashi

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1937 , vol. 33, p. 96 Chem. Zentralbl., 1938 , vol. 109, # I p. 1682 Full Text Show Details

Filachione; Lengel; Fisher

Industrial and Engineering Chemistry, 1945 , vol. 37, p. 388,389 Full Text Show Details

With sulfuric acid

T=120 - 130°C; unter Abdestillieren des Aethyllactats mit Aethanol;

Comm.Solv.Corp.

Patent: US2029694 , 1934 ; Full Text Show Details

Higashi

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1937 , vol. 33, p. 96 Chem. Zentralbl., 1938 , vol. 109, # I p. 1682 Full Text Show Details

Filachione; Lengel; Fisher

Industrial and Engineering Chemistry, 1945 , vol. 37, p. 388,389 Full Text Show Details

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T=400°C;

Imp.Chem.Ind.

Patent: US2265814 , 1939 ; Full Text Show Details

Ritchie

Journal of the Chemical Society, 1935 , p. 1061 Full Text Show Details

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Rx-ID: 5804283 Find similar reactions

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Standard Alcohol Co.

Patent: US2176201 , 1937 ;

T=110 - 115°C;

Full Text Show Details

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Rx-ID: 6188338 Find similar reactions

Standard Alcohol Co.

Patent: US2176201 , 1937 ;

T=110 - 115°C;

Full Text Show Details

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With methanol; alkali formate

T=110 - 115°C; im Silber- oder Kupferautoklaven;

Rx-ID: 6673127 Find similar reactions

Standard Alcohol Co.

Patent: US2176201 , 1937 ; Full Text Show Details

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With ethanol; alkali formate

T=110 - 115°C; im Silber- oder Kupferautoklaven;

Rx-ID: 6684727 Find similar reactions

Standard Alcohol Co.

Patent: US2176201 , 1937 ; Full Text Show Details

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With sulfuric acid

T=120°C;

Rx-ID: 6395918 Find similar reactions

Kirchhof; Snajewa

Chim.farm.Promysl., 1933 , p. 280 Chem. Zentralbl., 1934 , vol. 105, # II p. 591 Full Text Show Details

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Rx-ID: 8289306 Find similar reactions

Criegee

Justus Liebigs Annalen der Chemie, 1930 , vol. 481, p. 263,286 Chemische Berichte, 1931 , vol. 64, p. 260,264 Full Text Show Details

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With sulfuric acid

Rx-ID: 6395922 Find similar reactions

Rona; Itelsohn-Schechter

Biochemische Zeitschrift, 1928 , vol. 203, p. 295 Full Text Show Details

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Rx-ID: 698812 Find similar reactions

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With hydrogenchloride

T=0 - 10°C; Versetzen des Reaktionsprodukts mit Wasser und Benzol oder Toluol;

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Am.Cyanamid Co.

Patent: US1790262 , 1926 ; Full Text Show Details

I.G.Farbenind. Patent: DE544499 , 1925 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 264 Full Text Show Details

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Rx-ID: 101688 Find similar reactions

Simon; Piaux

Bulletin de la Societe de Chimie Biologique, vol. 6, p. 414 Chem. Zentralbl., 1924 , vol. 95, # II p. 1457 Full Text Show Details

With air

T=170 - 180°C; Kochen des erhaltenen Reaktionsprodukts mit Alkohol in Gegenwart von HCl,H2SO4 oder FeCl3 oder mit Alkohol auf 120grad erhitzt;

Chem.Werke Byk

Patent: DE278487 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 85 Full Text Show Details

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Grandiere

Bulletin de la Societe Chimique de France, 1924 , vol. <4> 35, p. 191 Full Text Show Details

T=210°C;

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Rx-ID: 6395919 Find similar reactions

With water; sodium nitrite

Barker; Skinner

Journal of the American Chemical Society, 1924 , vol. 46, p. 412 Full Text Show Details

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Barker; Skinner

Journal of the American Chemical Society, 1924 , vol. 46, p. 412 Full Text Show Details

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Rx-ID: 188289 Find similar reactions

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Jungfleisch; Godchot

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1907 , vol. 144, p. 425 Full Text View citing articles Show Details

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Curtius; Mueller

Chemische Berichte, 1904 , vol. 37, p. 1265 Full Text Show Details

fraktionierte Destillation unter vermindertem Druck;

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Rx-ID: 188059 Find similar reactions

T=135 - 150°C;

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Aritow; Demjanow

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1887 , vol. 19, p. 262

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Chemische Berichte, 20 Ref. <1887>,697 Full Text Show Details

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Rx-ID: 588231 Find similar reactions

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Strecker

Justus Liebigs Annalen der Chemie, 1854 , vol. 91, p. 356 Full Text Show Details

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Rx-ID: 6395920 Find similar reactions

Chem.Fabr.Guestrow

Patent: DE171835 ; Full Text Show Details

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Rx-ID: 6395921 Find similar reactions

Schering-Kahlbaum A.G.

Patent: DE518388 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 263,264 Full Text Show Details

With sulfuric acid; magnesium sulfate

Schering-Kahlbaum A.G.

Patent: DE518388 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 263,264 Full Text Show Details

With sulfuric acid

Schering-Kahlbaum A.G.

Patent: DE518388 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 263,264 Full Text Show Details