Cyclohexanone by Asch

Reaxys

PubChem

eMolecules

Reactions (1470)

Yield

Substances (2)

Citations (3478)

Conditions

References A

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397 Synthesize Find similar

With [HDIm]2[W2O11]; dihydrogen peroxide in methanol; water

T=59.84°C; 4 h;

Rx-ID: 29371919 Find similar reactions

Qiao, Yunxiang; Hou, Zhenshan; Li, Huan; Hu, Yu; Feng, Bo; Wang, Xiangrui; Hua, Li; Huang, Qingfa

Green Chemistry, 2009 , vol. 11, # 12 p. 1955 - 1960 Title/Abstract Full Text View citing articles Show Details

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398 Synthesize Find similar

With dichloro(.eta.3:.eta.2:.eta.3-dodeca-2,6,10-triene1,12-diyl)ruthenium(IV); caesium carbonate; isopropyl alcohol

T=82°C; 3 h; Inert atmosphere; Kinetics; Time;

Rx-ID: 29409866 Find similar reactions

Cadierno, Victorio; Crochet, Pascale; Francos, Javier; Garcia-Garrido, Sergio E.; Gimeno, Jose; Nebra, Noel

Green Chemistry, 2009 , vol. 11, # 12 p. 1992 - 2000 Title/Abstract Full Text View citing articles Show Details

399 Synthesize Find similar A: 78 %Chromat. B: 22 %Chromat.

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With water; hydrogen

T=20°C; P=750.075 Torr;

Rx-ID: 29418189 Find similar reactions

Hubert, Claudie; Denicourt-Nowicki, Audrey; Guegan, Jean-Paul; Roucoux, Alain

Dalton Transactions, 2009 , # 36 p. 7356 - 7358 Title/Abstract Full Text View citing articles Show Details

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400 Synthesize Find similar Rx-ID: 30098005 Find similar reactions

With CotA-laccase from the bacterium Bacillus subtilis T=37°C; pH=8; 0.5 h; aq. phosphate bufferEnzymatic reaction; MechanismKinetics; Reagent/catalystTimepHvaluePressure;

Pereira, Luciana; Coelho, Ana V.; Viegas, Cristina A.; Ganachaud, Christelle; Iacazio, Gilles; Tron, Thierry; Robalo, M. Paula; Martins, Ligia O.

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 11-12 p. 1857 - 1865 Title/Abstract Full Text View citing articles Show Details

401 Synthesize Find similar

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Rx-ID: 2008037 Find similar reactions

95%

With oxalyl dichloride; dimethyl sulfoxide in dichloromethane

T=-70°C; 0.666667 h; under argon;

Tolstikov, G. A.; Miftakhov, M. S.; Vostrikov, N. S.; Komissarova, N. G.; Adler, M. E.; Kuznetsov, O. M.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 1 p. 202 - 203 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 1 p. 224 - 225 Title/Abstract Full Text Show Details

92%

With aluminium trichloride; silver(I) bromate in acetonitrile

0.5 h; Heating;

Firouzabadi; Mohammadpoor-Baltork

Synthetic Communications, 1994 , vol. 24, # 8 p. 1065 - 1077 Title/Abstract Full Text View citing articles Show Details

90%

With chromium(VI) oxide; aluminum oxide

0.0166667 h;

Heravi, Majid M.; Ajami, Dariush; Ghassemzadeh, Mitra

Synthetic Communications, 1999 , vol. 29, # 5 p. 781 - 784 Title/Abstract Full Text View citing articles Show Details

Hide Details 90%

With chromium(VI) oxide; aluminum oxide; water

0.0166667 h;

Heravi, Majiid M.; Ajami, Dariush; Ghassemzadeh, Mitra

Synthesis, 1999 , # 3 p. 393 - 394 Title/Abstract Full Text View citing articles Show Details

89%

With zeofen

0.0333333 h; Irradiation;

Heravi; Ajami; Ghassemzadeh; Tabar-Hydar

Synthetic Communications, 2001 , vol. 31, # 14 p. 2097 - 2100 Title/Abstract Full Text View citing articles Show Details

85%

With Montmorillonite K10; iron nitrate (III)

Oxidation; deprotection; Irradiation;

Mojtahedi, Mohammad M.; Saidi, Mohammad R.; Bolourtchian, Mohammad; Heravi, Majid M.

Synthetic Communications, 1999 , vol. 29, # 19 p. 3283 - 3287 Title/Abstract Full Text View citing articles Show Details

80%

With chromium(VI) oxide; sulfuric acid in water; acetone

0.5 h;

Baker, R.; Rao, V. Bhaskar; Ravenscroft, P.D.; Swain, C.J.

Synthesis, 1983 , # 7 p. 572 - 574 Title/Abstract Full Text Show Details

80%

With Sodium bromate; ammonium chloride in water; acetonitrile

T=80°C; 0.75 h;

Shaabani; Karimi

Synthetic Communications, 2001 , vol. 31, # 5 p. 759 - 765 Title/Abstract Full Text View citing articles Show Details

77%

With aluminum oxide; [bis(acetoxy)iodo]benzene in acetonitrile

Oxidation; 1 h; Heating;

Heravi, Majid M.; Tajbakhsh, Mahmood; Ghassemzadeh, Mitra

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999 , vol. 54, # 3 p. 394 - 396 Title/Abstract Full Text View citing articles Show Details

75%

With (CTA)2S2O8 in acetonitrile

1 h; Reflux;

Tajbakhsh, Mahmoud; Alinezhad, Heshmatollah; Urimi, Azade Geran

Phosphorus, Sulfur and Silicon and the Related Elements, 2008 , vol. 183, # 6 p. 1447 - 1454 Title/Abstract Full Text View citing articles Show Details

60%

With γ-picolinium chlorochromate in dichloromethane

T=20°C; 15 h;

Salehi; Khodaei; Goodarzi

Russian Journal of Organic Chemistry, 2002 , vol. 38, # 11 p. 1671 - 1673 Title/Abstract Full Text View citing articles Show Details

With chromium(VI) oxide; aluminum oxide; water in dichloromethane

0.333333 h; Ambient temperature; Yield given;

Heravi, Majid M.; Ajami, Dariush; Tabar-Heydar, Kourosh

Monatshefte fur Chemie, 1999 , vol. 130, # 2 p. 337 - 339 Title/Abstract Full Text View citing articles Show Details

402 Synthesize Find similar

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Rx-ID: 3878266 Find similar reactions

97%

With baker's yeast; phosphate buffer in ethanol

T=37°C; 11 h;

Kamal, Ahmed; Rao, Maddamsetty V.; Meshram, Harshadas M.

Tetrahedron Letters, 1991 , vol. 32, # 23 p. 2657 - 2658 Title/Abstract Full Text View citing articles Show Details

94%

With peroxymonosulfuric acid; silica gel

Oxidation; 0.05 h; Irradiation;

Bose, D. Subhas; Venkat Narsaiah; Lakshminarayana

Synthetic Communications, 2000 , vol. 30, # 17 p. 3121 - 3125 Title/Abstract Full Text View citing articles Show Details

90%

With iron(II) sulfate in chloroform

T=20°C; Hydrolysis; 0.75 h;

Nasreen, Aayesha; Adapa, Srinivas R.

Organic Preparations and Procedures International, 1999 , vol. 31, # 5 p. 573 - 575 Title/Abstract Full Text View citing articles Show Details

Hide Details

87%

With K-10 clay-supported Fe(NO3)3 ("clayfen" reagent) in dichloromethane

5 h; Heating;

Laszlo, Pierre; Polla, Eugenio

Synthesis, 1985 , # 4 p. 439 - 440 Title/Abstract Full Text Show Details

85%

With CPCC in acetonitrile

1.5 h; Heating;

Baltork; Pouranshirvani

Synthetic Communications, 1996 , vol. 26, # 1 p. 1 - 7 Title/Abstract Full Text View citing articles Show Details

85%

With NTPPPODS in water; acetonitrile

0.5 h; Reflux;

Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad

Phosphorus, Sulfur and Silicon and the Related Elements, 2008 , vol. 183, # 6 p. 1388 - 1395 Title/Abstract Full Text View citing articles Show Details

81%

With polumer-supported phenyliodine bis(trifluoroacetate); water in tetrahydrofuran

0.75 h;

Chen; Cheng

Synthetic Communications, 2001 , vol. 31, # 24 p. 3847 - 3850 Title/Abstract Full Text View citing articles Show Details

79%

With NaBiO3; silica gel

0.05 h; microwave irradiation;

Mitra, Alok Kumar; De, Aparna; Karchaudhuri, Nilay

Journal of the Indian Chemical Society, 2001 , vol. 78, # 10-12 p. 721 - 722 Title/Abstract Full Text View citing articles Show Details

403 Synthesize Find similar

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Rx-ID: 5084975 Find similar reactions

92%

With trislt;trinitratocerium(IV)gt; paraperiodate; montmorillonite K-10 in dichloromethane

Oxidation; deprotection; 1.2 h; Heating;

Heravi, Majid M.; Oskooie, Hossein A.; Ghassemzadeh, Mitra; Zameni, Fatemeh F.

Monatshefte fur Chemie, 1999 , vol. 130, # 10 p. 1253 - 1256 Title/Abstract Full Text View citing articles Show Details

90%

With NTPPPODS in acetonitrile

0.416667 h; Reflux;

Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad

Phosphorus, Sulfur and Silicon and the Related Elements, 2008 , vol. 183, # 6 p. 1388 - 1395 Title/Abstract Full Text View citing articles Show Details

89%

With Montmorillonite K-10 supported ammonium chlorochromate

0.0333333 h; microwave irradiation;

Heravi, Majid M.; Hekmatshoar, Rahim; Beheshtiha, Yahya S.; Ghassemzadeh, Mitra

Monatshefte fur Chemie, 2001 , vol. 132, # 5 p. 651 - 654 Title/Abstract Full Text View citing articles Show Details

Hide Details

88%

With chromium(VI) oxide; aluminum oxide

0.05 h;

Heravi, Majid M.; Ajami, Dariush; Ghassemzadeh, Mitra

Synthetic Communications, 1999 , vol. 29, # 5 p. 781 - 784 Title/Abstract Full Text View citing articles Show Details

88%

With chromium(VI) oxide; aluminum oxide; water

0.05 h;

Heravi, Majiid M.; Ajami, Dariush; Ghassemzadeh, Mitra

Synthesis, 1999 , # 3 p. 393 - 394 Title/Abstract Full Text View citing articles Show Details

88%

With bis(trimethylsilyl) chromate on montmorillonite K-10

0.0277778 h; microwave irradiation;

Heravi, Majid M.; Ajami, Dariush

Monatshefte fur Chemie, 1999 , vol. 130, # 5 p. 709 - 712 Title/Abstract Full Text View citing articles Show Details

70%

With aluminum oxide; [bis(acetoxy)iodo]benzene in acetonitrile

Oxidation; 1 h; Heating;

Heravi, Majid M.; Tajbakhsh, Mahmood; Ghassemzadeh, Mitra

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999 , vol. 54, # 3 p. 394 - 396 Title/Abstract Full Text View citing articles Show Details

65%

With β-cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole1,3-dione in water; acetone

T=20°C; 1 h;

Narender; Reddy, M. Somi; Kumar, V. Pavan; Nageswar; Rao, K. Rama

Tetrahedron Letters, 2005 , vol. 46, # 12 p. 1971 - 1973 Title/Abstract Full Text View citing articles Show Details

With chromium(VI) oxide; aluminum oxide; water in dichloromethane

0.416667 h; Ambient temperature; Yield given;

Heravi, Majid M.; Ajami, Dariush; Tabar-Heydar, Kourosh

Monatshefte fur Chemie, 1999 , vol. 130, # 2 p. 337 - 339 Title/Abstract Full Text View citing articles Show Details

With aluminium trichloride; silver(I) bromate in acetonitrile

1.5 h; Heating; Yield given;

Mohammadpoor-Baltork, Iraj; Nourozi, Ali Reza

Synthesis, 1999 , # 3 p. 487 - 490 Title/Abstract Full Text View citing articles Show Details

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404 Synthesize Find similar

A: 32.4 % Chromat.

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With carbon dioxide; oxygen; palladium dichloride

T=50°C; P=105011 Torr; 15 h;

Rx-ID: 11269054 Find similar reactions

Jiang, Huan-Feng; Shen, Yan-Xia; Wang, Zhao-Yang

Tetrahedron, 2008 , vol. 64, # 3 p. 508 - 514 Title/Abstract Full Text View citing articles Show Details

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405 Synthesize Find similar

Rx-ID: 27864505 Find similar reactions

Ube Industries, Ltd.

Patent: EP1975155 A1, 2008 ; Location in patent: Page/Page column 4 ;

in toluene

T=270°C; 0.00166667 h; Hide Experimental Procedure

Title/Abstract Full Text Show Details

[Referential example 2: Production of Decane-1,10-dicarbonimide]; 54g of the resultant PXA was dissolved in 560 ml of toluene and the liquid was sent to a tube-type reactor having an inside diameter of 0.5 mm heated at 270 °C to thermally decompose PXA. The reaction pressure at this time is 10 MPa-G and the average residence time of the reaction liquid in the reactor was 6 seconds. As a result of a gas chromatography analysis, the PXA conversion was 100 percent, and products of decane-1,10-dicarbonimide and cylcohexanone were confirmed. After distillation removal of toluene and cylcohexanone, recrystallization (with a solvent: acetonitrile) was performed to obtain 26.5g of decane-1,10dicarbonimide. A

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406 Synthesize Find similar Rx-ID: 27886157 Find similar reactions

A: 1% D: 0% E: 1% F: 17% J: 6%

With hydrogen; ruthenium

T=150 - 300°C; 4 h; Product distribution / selectivity; Hide Experimental Procedure

Battelle Memorial Institute

Patent: US7425657 B1, 2008 ; Location in patent: Page/Page column 7 ; Title/Abstract Full Text Show Details

As described in the examples, three chemical models were reacted at 150, 200, 250, and 300° C. using either the palladium or the ruthenium catalyst. The products varied with temperature and the catalyst metal. The experimental product from the catalyzed tests contained about 30 components of sufficient concentration to be identified and quantified. This level of complexity can be compared to whole hydrogenated bio-oil, which typically contains hundreds of components. The components were separated into four groups to represent the products from acetic acid, guaiacol and two collections of products from furfural.Ruthenium Catalyzed Hydrogenations. For guaiacol hydrogenation in the presence of ruthenium catalyst the products were similar to those identified earlier in our laboratory. At 150° C., 30percent of the guaiacol had already been converted by the time the reactor reached temperature, time zero in FIG. 1. The primary product was that resulting from saturation of the phenolic ring, 2-methoxycyclohexanol (60percent yield (at) 4 h). Cyclohexanediol was the secondary product (11percent), although cyclohexanol was also significant (6percent). The methanol byproduct was found (1percent). There was little phenol formed at this temperature. At 200° C. the initial conversion of guaiacol during heatup was 44percent. As shown in FIG. 2 the methoxycyclohexanols were still the main product (54percent yield (at) 4 h), but cyclohexanediol became less important (4percent) while more cyclohexanol was formed (12percent). More methanol was present (2percent), as was more phenol. At 250° C., 60percent of the guaiacol was converted by the time the reactor reached temperature. As shown in FIG. 3 cyclohexanol almost surpassed methoxycyclohexanols as the main product. Methoxycyclohexanol yield peaked at 17percent in the 1 to 2 h range before reacting on to secondary products. The maximum cyclohexanol yield was 13percent. Cyclohexanediol was only a minor product (1percent). More phenol was evident and cyclohexane became a significant product (2percent); however, the hexane recovery is likely limited by its low solubility in the water. More cyclohexane may have been actually produced and remained in the reactor as a separate light phase, which could not be sampled by our method. Over the period of the test, the amount of aqueous phase products is reduced. A large methane gas product was produced in this test, as has been reported for processing at these conditions of temperature and catalyst wherein phenol was extensively gasified at as low as 250° C.xi At 300° C., phenol is the primary product that was recoverable. Cyclohexanol and methoxycyclohexanol are early products which are reduced to low levels within the first hour at temperature. All three

isomers of methyl-phenol (cresols) are significant byproducts, as is benzene. Cyclohexane is present in the water product only at low concentration, but is likely present as a significant product in a separate phase. Because of the large amount of methane gas formation, this test was hydrogen limited with the reactor pressure surpassing the pressure set point after 1 h of operation and this factor is expected to have skewed the mechanism away from the high-use hydrogenation pathways, such as saturation of the aromatic ring. xiElliott, D. C.; Hart, T. R.; Neuenschwander, G. G. "Chemical Processing in High-Pressure Aqueous Environments. 8. Improved Catalysts for Hydrothermal Gasification." Ind Eng. Chem. Res. 45(11) 3776-81, 2006. A

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407 Synthesize Find similar Rx-ID: 27886158 Find similar reactions

With hydrogen; palladium

T=200 - 300°C; 3 - 4 h; Product distribution / selectivity; Hide Experimental Procedure

Battelle Memorial Institute

Patent: US7425657 B1, 2008 ; Location in patent: Page/Page column 8-9 ; Title/Abstract Full Text Show Details

Palladium Catalyzed Hydrogenations. In the case of palladium catalysis, the results were different. At 150° C., the primary product from guaiacol was 2-methoxy-cyclohexanone, resulting from a less complete saturation of the phenolic ring while a large portion of the guaiacol remained unreacted. Methoxycyclohexanol was found at only 1/10th the concentration of the cyclic ketone. Cyclohexanediol was a lesser product, and cyclohexanol and phenol were almost insignificant. The methanol byproduct was found. At 200° C., shown in FIG. 13 the methoxycyclohexanols were the main product, but some cyclohexanediol was present. Cyclohexanol was slightly more prominent. More methanol was present. As seen in FIG. 14, at 250° C. methoxycyclohexanols were the main product, but significant guaiacol remained at the end of the test. Cyclohexanediol was a minor product. Cyclohexane was a noticeable product and slightly surpassed in quantity both cyclohexanol and phenol. Unlike the case of ruthenium catalysis, over the period of the test, the total amount of aqueous phase products appeared to remain nearly constant. At 300° C. the reaction of guaiacol through methoxycyclohexanol to cyclohexane was evident, as seen in FIG. 15. Methanol was the other significant product and became the major aqueous phase product by the end of the test. Phenol also played a larger role in the conversion process at this higher temperature than at the lower temperatures. Guaiacol was converted to almost 98percent after the 4 hours at temperature. The total amount of aqueous phase products dropped by about 3/4ths by the end of the test, suggesting that the major products were the volatile cyclic hydrocarbons. A

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408 Synthesize Find similar

With acetic acid in chloroform-d1; water

T=20°C; 1 h;

Rx-ID: 27964045 Find similar reactions

Hetzer, Ralf Helmut; Gais, Hans-Joachim; Raabe, Gerhard

Synthesis, 2008 , # 7 p. 1126 - 1132 Title/Abstract Full Text View citing articles Show Details

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409 Synthesize Find similar

A: 75% B: 17%

With WO3; aluminum oxide in acetonitrile

T=20°C; 3 h;

410

Rx-ID: 28151346 Find similar reactions

Suzuki, Ken; Watanabe, Tomonari; Murahashi, Shun-Ichi

Angewandte Chemie - International Edition, 2008 , vol. 47, # 11 p. 2079 - 2081 Title/Abstract Full Text View citing articles Show Details

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A: 90 %Chromat. B: 2 %Chromat. C: 4 %Chromat.

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With WO3; aluminum oxide; DPPH radical; oxygen in acetonitrile

T=80°C; P=37503.8 Torr; 8 h;

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Rx-ID: 28151348 Find similar reactions

Suzuki, Ken; Watanabe, Tomonari; Murahashi, Shun-Ichi

Angewandte Chemie - International Edition, 2008 , vol. 47, # 11 p. 2079 - 2081 Title/Abstract Full Text View citing articles Show Details

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411 Synthesize Find similar

With oxygen

T=60°C; Activation energyReactivity; Temperature;

Rx-ID: 28165351 Find similar reactions

Koshel'; Kurganova; Smirnova; Plakhtinskii; Belysheva

Russian Journal of Organic Chemistry, 2008 , vol. 44, # 4 p. 553 - 556 Title/Abstract Full Text View citing articles Show Details

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412 Synthesize Find similar

With oxygen

T=60°C; Activation energyReactivity; Temperature;

Rx-ID: 28165353 Find similar reactions

Koshel'; Kurganova; Smirnova; Plakhtinskii; Belysheva

Russian Journal of Organic Chemistry, 2008 , vol. 44, # 4 p. 553 - 556 Title/Abstract Full Text View citing articles Show Details

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413 Synthesize Find similar

With oxygen

T=60°C; Activation energyReactivity; Temperature;

Rx-ID: 28165354 Find similar reactions

Koshel'; Kurganova; Smirnova; Plakhtinskii; Belysheva

Russian Journal of Organic Chemistry, 2008 , vol. 44, # 4 p. 553 - 556 Title/Abstract Full Text View citing articles Show Details

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414 Synthesize Find similar

Rx-ID: 28165355 Find similar reactions

With oxygen

T=60°C; Activation energyReactivity; Temperature;

Koshel'; Kurganova; Smirnova; Plakhtinskii; Belysheva

Russian Journal of Organic Chemistry, 2008 , vol. 44, # 4 p. 553 - 556 Title/Abstract Full Text View citing articles Show Details

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415 Synthesize Find similar

With oxygen

T=60°C; Activation energyReactivity; Temperature;

Rx-ID: 28165356 Find similar reactions

Koshel'; Kurganova; Smirnova; Plakhtinskii; Belysheva

Russian Journal of Organic Chemistry, 2008 , vol. 44, # 4 p. 553 - 556 Title/Abstract Full Text View citing articles Show Details

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416 Synthesize Find similar

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Rx-ID: 28165565 Find similar reactions

A: 3 %Chromat. B: 12 %Chromat. C: 11 %Chromat. D: 30 %Chromat.

With tert.-butylhydroperoxide; anhydrous iron chloride; [(n-C4H9)4N][OsVI(N)Cl4] in dichloromethane

T=23°C; 0.0833333 h;

Yiu, Shek-Man; Man, Wai-Lun; Lau, Tai-Chu

Journal of the American Chemical Society, 2008 , vol. 130, # 32 p. 10821 - 10827 Title/Abstract Full Text View citing articles Show Details

417 Synthesize Find similar

87%

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Rx-ID: 28170870 Find similar reactions

With tetraethylammonium bromide; 1-hydroxy-3H-benz[d] [1,2]iodoxole-1,3-dione in acetonitrile

T=20 - 60°C;

Bellale, Eknath V.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.

Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9473 - 9475 Title/Abstract Full Text View citing articles Show Details

418 Synthesize Find similar

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Rx-ID: 28170871 Find similar reactions

With tetraethylammonium bromide; 1-hydroxy-3H-benz[d] [1,2]iodoxole-1,3-dione in acetonitrile

Bellale, Eknath V.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.

Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9473 - 9475

T=60°C;

Title/Abstract Full Text View citing articles Show Details

419 Synthesize Find similar

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Rx-ID: 28194818 Find similar reactions

With hydrogenchloride in water; acetonitrile

T=20°C; 40 h; Kinetics;

Krohn, Karsten; Cludius-Brandt, Stephan

Synthesis, 2008 , # 15 art. no. T01408SS, p. 2369 - 2372 Title/Abstract Full Text View citing articles Show Details

420 Synthesize Find similar

52%

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With acetic acid in ethanol

Reflux;

Rx-ID: 28232941 Find similar reactions

Ragavendran, Jegadeesan Vaigunda; Sriram, Dharmarajan; Kotapati, Srikanth; Stables, James; Yogeeswari, Perumal

European Journal of Medicinal Chemistry, 2008 , vol. 43, # 12 p. 2650 - 2655 Title/Abstract Full Text View citing articles Show Details

421 Synthesize Find similar

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Rx-ID: 28254891 Find similar reactions

With caesium carbonate in N,N-dimethyl-formamide

T=70°C;

Knowles, Deborah A.; Mathews, Christopher J.; Tomkinson, Nicholas C. O.

Synlett, 2008 , # 18 p. 2769 - 2772 Title/Abstract Full Text View citing articles Show Details

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422 Synthesize Find similar Rx-ID: 28505817 Find similar reactions

With Pt/titania; water

3 h; Photolysis; Reactivity; Reagent/catalystWavelength;

Yoshida, Hisao; Yuzawa, Hayato; Aoki, Masanori; Otake, Kazuko; Itoh, Hideaki; Hattori, Tadashi

Chemical Communications, 2008 , # 38 p. 4634 - 4636 Title/Abstract Full Text View citing articles Show Details

423 Synthesize Find similar

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Rx-ID: 1979638 Find similar reactions

99%

With water

T=80°C; 0.25 h; microwave irradiation;

Procopio, Antonio; Gaspari, Marco; Nardi, Monica; Oliverio, Manuela; Tagarelli, Antonio; Sindona, Giovanni

Tetrahedron Letters, 2007 , vol. 48, # 49 p. 8623 - 8627 Title/Abstract Full Text View citing articles Show Details

85%

With water; acetone; mesoporous aluminosilicate T=55°C; 2 h;

Robinson, Mathew W.C.; Graham, Andrew E.

Tetrahedron Letters, 2007 , vol. 48, # 27 p. 4727 - 4731 Title/Abstract Full Text View citing articles Show Details

90 % Chromat.

With aluminium(III) iodide in acetonitrile; benzene

0.166667 h; Ambient temperature;

Barua, Nabin C.; Sarmah, Parijat

Tetrahedron Letters, 1989 , vol. 30, # 35 p. 4703 - 4704 Title/Abstract Full Text View citing articles Show Details

Hide Details

With erbium trifluoromethanesulfonate in nitromethane

0.5 h; Product distribution; Further Variations:Solventsreaction time;

Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Nardi, Monica; Procopio, Antonio; Tagarelli, Antonio

Synthesis, 2004 , # 4 p. 496 - 498 Title/Abstract Full Text View citing articles Show Details

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424 Synthesize Find similar Rx-ID: 9963180 Find similar reactions

With oxygen

Product distribution / selectivity; Hide Experimental Procedure

Sumitomo Chemical Company, Limited

Patent: EP1748042 A1, 2007 ; Location in patent: Page/Page column 6-7; 10-11 ; Title/Abstract Full Text Show Details

1; 11; 13:

Example 1; Cyclohexane was oxidized in a liquid phase and the reaction mixture was washed with water to obtain the wastewater containing hydroxycaproic acid together with a mixture of cyclohexanone and cyclohexanol. The wastewater was cooled and the crystallized adipic acid was filtered to obtain the wastewater wherein the content of hydroxycaproic acid was 18.5percent by weight. In the wastewater, adipic acid, glutaric acid, e-caprolactone, esters of adipic acid and esters of hydrocaproic acid were contained other than hydroxycaproic acid. Into a 100 mL Schlenk Tube equipped with a reflux condenser, 0.07 g of sodium tungstate, 9.61 g of 30percent by weight aqueous hydrogen peroxide and 80 mg of sulfuric acid were charged at room temperature and the mixture was stirred at room temperature for 1 minute to prepare a tungsuten catalyst suspension. 14.3 g of the wastewater containing hydroxycaproic acid obtained the above (content of hydroxycaproic acid: 18.5percent by weight) was charged into this and the mixture was stirred at an inner temperature of 90°C for 4 hours to effect reaction. The reaction liquid containing adipic acid was obtained. Yield of adipic acid: 26percent.; Example 11; Cyclohexane was oxidized in a liquid phase and the reaction mixture was washed with water to obtain the wastewater containing hydroxycaproic acid (content of hydroxycaproic acid: 8.8percent by weight) together with a mixture of cyclohexanone and cyclohexanol. In the wastewater, adipic acid, glutaric acid, e-caprolactone, esters of adipic acid and esters of hydroxycaproic acid were contained other than hydroxycaproic acid. Into a 500 mL four-necked flask equipped with a reflux condenser, 2.47 g of sodium tungstate, 7.5 g of water and 9.0 g of sulfuric acid were charged at room temperature to prepare a tungsten catalyst suspension. 226.6 g of the above-mentioned wastewater containing hydroxycaproic acid (content of hydroxycaproic acid: 8.8percent by weight) was added thereto and the mixture was adjusted at an inner temperature of 100°C. 72.1 g of 30percent by weight aqueous hydrogen peroxide was added dropwise thereto at the same temperature over 8 hours and then the mixture was stirred for 3 hours to effect reaction and the reaction liquid containing adipic acid was obtained. The reaction liquid was filtered at an inner temperature of 70°C and a yellow solid was filtered off. The filtrate obtained was cooled to an inner temperature of 10°C over 12 hours and the crystal of adipic acid precipitated was filtered. Yield of adipic acid combined in crystal and in the filtrate: 89percent.; Example 13; Cyclohexane was oxidized in a liquid phase and the reaction mixture was washed with water to obtain the wastewater containing hydroxycaproic acid (content of hydroxycaproic acid: 7.5percent by weight) together with a mixture of cyclohexanone and cyclohexanol. In the wastewater, adipic acid, glutaric acid, e-caprolactone, esters of adipic acid and esters of hydroxycaproic acid were contained other than hydroxycaproic acid. Into a 300 mL four-necked flask equipped with a reflux condenser, 1.29 g of sodium tungstate, 3.9 g of water and 6.8 g of 60percent nitric acid were charged at room temperature to prepare a tungsten catalyst suspension. 120 g of the above-mentioned wastewater containing hydroxycaproic acid (content of hydroxycaproic acid: 7.5percent by weight) was added thereto and the mixture was adjusted at an inner temperature of 100°C. 37.6 g of 30percent by weight aqueous hydrogen peroxide was added dropwise thereto at the same temperature over 6 hours and then the mixture was stirred for 4 hours to effect reaction and the reaction liquid containing adipic acid was obtained. Yield of adipic acid: 73percent. A

425

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With bis(acetylacetonate)oxovanadium; trifluorormethanesulfonic acid; oxygen in acetic acid

T=91.85°C; P=760 Torr; 10 h; Product distribution;

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Kobayashi, Hirokazu; Yamanaka, Ichiro

Chemistry Letters, 2007 , vol. 36, # 1 p. 114 - 115 Title/Abstract Full Text View citing articles Show Details

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426 Synthesize Find similar Rx-ID: 10672745 Find similar reactions

With oxygen; acetic acid; 1-hydroxy-pyrrolidine-2,5dione; anhydrous cobalt diacetate in water

T=105°C; P=22502.3 Torr; 0.75 h; Product distribution / selectivity; Hide Experimental Procedure

DAICEL CHEMICAL INDUSTRIES, LTD.

Patent: EP1862442 A1, 2007 ; Location in patent: Page/Page column 16 ; Title/Abstract Full Text Show Details

In a 2000-cc titanium autoclave were placed 450 g of cyclohexane, 550 g of acetic acid, 0.690 g of N-hydroxysuccinimide, and 9.960 g of cobalt acetate tetrahydrate, and the autoclave was pressurized to 3 MPa with a 50:50 (by mole) gaseous mixture of oxygen and nitrogen. The autoclave was held to 105°C on an oil bath for carrying out a reaction for forty-five minutes, was cooled to room temperature, and opened to release the pressure. The resulting reaction mixture included a solid layer mainly containing adipic acid, and a liquid layer. The liquid layer contained two separated layers, i.e., an upper layer mainly containing cyclohexane, and a lower layer mainly containing acetic acid. Each of these layers was separated and analyzed to find that the conversion from cyclohexane was 17.3percent and the selectivities of adipic acid, cyclohexanone, cyclohexanol, and succinic acid were 54.3percent, 11.2percent, 7.5percent, and 4.2percent, respectively.

With oxygen; acetic acid; 1-hydroxy-pyrrolidine-2,5dione; N-hydroxy-glutarimide; anhydrous cobalt diacetate in water

T=105°C; P=22502.3 Torr; 0.75 h; Product distribution / selectivity; Hide Experimental Procedure

DAICEL CHEMICAL INDUSTRIES, LTD.

Patent: EP1862442 A1, 2007 ; Location in patent: Page/Page column 16 ; Title/Abstract Full Text Show Details

An aliquot of this mixture (12.44 g) was diluted with 540 g of acetic acid, and placed together with 450 g of cyclohexane and 8.39 g of cobalt acetate tetrahydrate in a 2000-cc titanium autoclave, and the autoclave was pressurized to 3 MPa with a 50:50 (by mole) gaseous mixture of oxygen and nitrogen. The autoclave was held to 105°C on an oil bath to carry out a reaction for forty-five minutes, cooled to room temperature, and opened to release the pressure. The resulting mixture contained a solid layer mainly containing adipic acid, and a liquid layer, as in the first reaction. The liquid layer had been separated into two layers, i.e., an upper layer mainly containing cyclohexane, and a lower layer mainly containing acetic acid. Each of these layers was separated and analyzed to find that the conversion from cyclohexane was 17.1percent, and the selectivities of adipic acid, cyclohexanone, cyclohexanol, and succinic acid were 53.9percent, 12.1percent, 7.9percent, and 4.6percent, respectively. A

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427 Synthesize Find similar

A: 90%

428

With water; oxygen; lithium bromide; copper(ll) bromide in tetrahydrofuran

T=25°C; P=760.051 Torr;

Rx-ID: 11162091 Find similar reactions

Qaseer

Polish Journal of Chemistry, 2007 , vol. 81, # 1 p. 31 - 38 Title/Abstract Full Text View citing articles Show Details

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With recombinant enoate reductase from Yersinia bercovieri in phosphate buffer

T=25°C; pH=7.5; Enzyme kinetics;

Rx-ID: 25921743 Find similar reactions

Chaparro-Riggers, Javier F.; Rogers, Thomas A.; Vazquez-Figueroa, Eduardo; Polizzi, Karen M.; Bommarius, Andreas S.

Advanced Synthesis and Catalysis, 2007 , vol. 349, # 8-9 p. 1521 - 1531 Title/Abstract Full Text View citing articles Show Details

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429 Synthesize Find similar Rx-ID: 25956255 Find similar reactions

A: 76.5 % Chromat. B: 5.9 % Chromat. C: 4.8 % Chromat. D: 6.4 % Chromat.

With SiAlP-4.5 in acetonitrile

T=400°C; Beckmann rearrangement; 12 h; atmospheric pressure; Product distribution; Further Variations:CatalystsSolventsTemperaturesmicrowave irradiation;

Conesa; Mokaya; Yang; Luque; Campelo; Romero

Journal of Catalysis, 2007 , vol. 252, # 1 p. 1 - 10 Title/Abstract Full Text View citing articles Show Details

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430 Synthesize Find similar

A: 66.6%

Rx-ID: 25963609 Find similar reactions

Erhardt, Stefan; Macgregor, Stuart A.; McCullough, Kevin J.; Savill, Karen; Taylor, Benjamin J.

Organic Letters, 2007 , vol. 9, # 26 p. 5569 - 5572 Title/Abstract Full Text View citing articles Show Details

in decane

T=180°C; 16 h;

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431 Synthesize Find similar

Hooley, Richard J.; Restorp, Per; Iwasawa, Tetsuo; Rebek Jr., Julius

Journal of the American Chemical Society, 2007 , vol. 129, # 50 p. 15639 - 15643 Title/Abstract Full Text View citing articles Show Details

in benzene-d6

Equilibrium constant;

432 Synthesize

Rx-ID: 25994226 Find similar reactions

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Rx-ID: 25994244 Find similar reactions

Hooley, Richard J.; Restorp, Per; Iwasawa, Tetsuo; Rebek Jr., Julius

Journal of the American Chemical Society, 2007 , vol. 129, # 50 p. 15639 - 15643 Title/Abstract Full Text View citing articles Show Details

in various solvent(s) Equilibrium constant;

433 Synthesize Find similar

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Rx-ID: 2105374 Find similar reactions

in butan-1-ol

T=30°C; other solv., and temp.; Equilibrium constant;

Efimova, G. A.; Shutova, I. V.; Shapiro, Yu. E.; Efimov, V. A.; Turov, B. S.; Makarov, V. M.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 6.1 p. 1081 - 1084 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 6 p. 1201 - 1204 Title/Abstract Full Text Show Details

With aluminum oxide; iron(III) oxide in decalin

T=20°C; effect of catalyst poisoning with benzoic acid and pyridine, var. temperatures; Rate constant;

Vit, Zdenek; Nondek, Lubomir; Malek, Jaroslav

Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 8 p. 2235 - 2245 Title/Abstract Full Text Show Details

With potassium hydroxide

T=20.45°C; Equilibrium constant; Further Variations:Temperatures;

Shevelyova, Marina P.; Kabo, Gennady J.; Blokhin, Andrey V.; Kabo, Audrey G.; Jursha, Joseph A.; Rajko, Anna A.

Journal of Chemical and Engineering Data, 2006 , vol. 51, # 1 p. 40 - 45 Title/Abstract Full Text View citing articles Show Details

Hide Details

Shevelyova, Marina P.; Zaitsau, Dzmitry H.; Paulechka, Yauheni U.; Kabo, Gennady J.; Verevkin, Sergey P.

Journal of Chemical and Engineering Data, 2006 , vol. 51, # 5 p. 1946 - 1952 Title/Abstract Full Text View citing articles Show Details

T=58.95°C; Equilibrium constant;

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434 Synthesize Find similar

435

Rx-ID: 2676976 Find similar reactions

A: 52.2% B: 0.9%

With hydrogen; cyclohexanone; magnesium oxide; ruthenium in water

T=99.9°C; P=15001.2 Torr; Product distribution;

Sokol'skii, D. V.; Ualikhanova, A.; Temirbulatova, A. E.; Mailyubaev, B. T.

Journal of Organic Chemistry USSR (English Translation), 1986 , p. 1520 - 1524 Zhurnal Organicheskoi Khimii, 1986 , vol. 22, # 8 p. 1693 - 1697 Title/Abstract Full Text Show Details

A: 67 % Chromat. B: 29 % Chromat.

With aluminium; platinum on activated charcoal in water

0.166667 h; microwave irradiation;

Miyazawa, Akira; Saitou, Kaori; Tanaka, Kan; Gaedda, Thomas M.; Tashiro, Masashi; Prakash, G. K. Surya; Olah, George A.

Tetrahedron Letters, 2006 , vol. 47, # 9 p. 1437 - 1439 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5163439 Find similar reactions

88%

With HOF* CH3CN in dichloromethane

T=0°C; 0.0166667 h;

Carmeli, Mira; Rozen, Shlomo

Tetrahedron Letters, 2006 , vol. 47, # 5 p. 763 - 766 Title/Abstract Full Text View citing articles Show Details

60%

With hexaaquairon(III) perchlorate

2 h;

Parmar, Anupama; Goyal, Rita; Kumar, Baldev; Kumar, Harish

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998 , vol. 37, # 9 p. 941 - 942 Title/Abstract Full Text Show Details

Multi-step reaction with 3 steps 1: colloid/al platinum; hydrochloric acid / 1520 Torr / Hydrogenation 2: diethyl ether / Leiten von Luft durch die Loesung 3: diluted hydrochloric acid View Scheme

Harkins; Lochte

Journal of the American Chemical Society, 1924 , vol. 46, p. 454 Full Text Show Details

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436 Synthesize Find similar

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With triethylamine in dichloromethane

T=-20°C; Swern oxidation; Product distribution; Further Variations:Temperatures;

Kawaguchi, Tatsuya; Miyata, Hiroyuki; Ataka, Kikuo; Mae, Kazuhiro; Yoshida, Jun-Ichi

Angewandte Chemie - International Edition, 2005 , vol. 44, # 16 p. 2413 - 2416 Title/Abstract Full Text View citing articles Show Details

Stage #1: dimethyl sulfoxide; trifluoroacetic anhydride in dichloromethane

T=-30 - 20°C; Swern Oxidation; 2.77778E-06 0.166667 h; Stage #2: cyclohexanol in dichloromethane

T=-30 - 20°C; Swern Oxidation; 2.77778E-06 0.166667 h; Stage #3: With triethylamine in dichloromethane

T=-30 - 20°C; Swern Oxidation; 0.0666667 h; Product distribution / selectivity; Hide Experimental Procedure

Ube Industries, Ltd.

Patent: EP1710223 A1, 2006 ; Location in patent: Page/Page column 8-21; 23-37; 39-45 ; Title/Abstract Full Text Show Details

1; 2; 3; 4; 5; 6; 7; 8; 9; 10; 11; 12; 13; 14; 17; 19; 20; 21; 22; 23; 24; 25; 26; 27; 28; 29; 30; 3; 4; 40; 41; 42; 43; 44; 45; 46; 47; 48; 49; 50; 51; 52; 53; 54; 55; 56:

In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two channels for respectively introducing a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, introducing channel, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and the each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as that for the step (1)) was used. A reaction product liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 0.1 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for the step (1)) was used. A reaction product solution-discharging channel of the microreactor of step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound-supply source through SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor, for step (1), at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained in the reactor for 0.01 seconds, the resultant reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained in the reactor for the step (2) for 1.2 seconds, the resultant reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min into the reactor. After the above reaction operation was carried out for 4 minutes, the resultant reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle containing an internal standard substance for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 0.01 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 78percent Cyclohexyl trifluoroacetate 5percent Cyclohexyl methylthiomethyl ether 3percent Cyclohexanol 10percent; Example 2 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for sulfoxide-containing liquid and activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and the each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as that for the step (1)) was used. A reaction product liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution introducing channel of a microreactor of the step (2) through a connecting SUS tube (inner diameter: 0.25 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of the microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 0.05 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 0.05 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 66percent Cyclohexyl trifluoroacetate 6percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 21percent; Example 3 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as that for the step (1)) was used. A reaction product

liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of a microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution discharging channel of the microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low temperature bath set at a temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the resultant reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle containing an internal standard substance for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 66percent Cyclohexyl trifluoroacetate 6percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 18percent; Example 4 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as that for the step (1)) was used. A reaction product liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution introducing channel of a microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 100 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution discharging channel of the microreactor of the step (2) was connected to a reaction product solution introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low temperature bath set at a temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min, through a gas-tight syringe. Immediately after the reaction mixture solution was retained for 24 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 24 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 70percent Cyclohexyl trifluoroacetate 5percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 15percent; Example 5 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as that for step (1)) was used. A reaction product liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of a microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 100 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low temperature bath set at a temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 12 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 71percent Cyclohexyl trifluoroacetate 5percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 15percent; Example 6 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) T-shaped joint-type reactor (cross-sectional inner diameter: 0.8 mm) To each of two introduction channels for a sulfoxide-containing liquid and an activating agentcontaining liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source, through the SUS tube.Step (2) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid-introducing channel width: 40 μm) was used. A reaction product liquid-discharging channel of the T joint type reactor of the step (1) was connected to a reaction product solution introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (2)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low temperature bath set at a temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 72percent Cyclohexyl trifluoroacetate 10percent Cyclohexyl methylthiomethyl ether 3percent Cyclohexanol 8percent; Example 7 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid-introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A T-joint-type reactor (cross-sectional inner diameter: 0.8 mm) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol introducing-channel of a microreactor for step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA used in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 55percent Cyclohexyl trifluoroacetate 24percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 15percent; Example 8 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the reactors shown below.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solutionintroducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A T-joint-type reactor (cross-sectional inner diameter: 0.8 mm) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the resultant reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA used in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 69percent Cyclohexyl trifluoroacetate 7percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 19percent; Example 9 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A T-joint-type reactor (cross-sectional inner diameter: 0.8 mm) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 63percent Cyclohexyl trifluoroacetate 22percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 9percent; Example 10 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was

retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution discharged from the microreactor for the step (3) was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.0 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 67percent Cyclohexyl trifluoroacetate 1percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 23percent; Example 11 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) using a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide (DMSO)/methylene chloride solution having a concentration of 2.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle containing an internal standard substance for one minute. The amount of DMSO and TFAA used in the step (1) was 1.0 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 69percent Cyclohexyl trifluoroacetate 5percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 17percent; Example 12 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 3.0 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 74percent Cyclohexyl trifluoroacetate 2percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 15percent; Example 13 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid-introducing channel and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as microreactor for the step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution discharging channel. The microreactors for steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 0.8 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 0.5 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 0.2 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 0.3 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution was determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 84percent Cyclohexyl trifluoroacetate 4percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 9percent; Example 14 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agentcontaining liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of 0°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.5 equivalents, the reaction temperature of the step (1) was 0°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 36percent Cyclohexyl trifluoroacetate 9percent Cyclohexyl methylthiomethyl ether 2percent Cyclohexanol 48percent; Example 17 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle containing an internal standard substance for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 77percent Cyclohexyl trifluoroacetate 4percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 12percent; Example 19 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out by using the following reactors.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 0.1 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of the microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 0.01 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 0.01 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 75percent Cyclohexyl trifluoroacetate 1percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 15percent; Example 20 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out by using the following reactor.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agentcontaining liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) using a connecting SUS tube (inner diameter: 0.1 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of 0°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 0.01 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was 0°C, and the reaction time was 0.01 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 80percent Cyclohexyl trifluoroacetate 1percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 10percent; Example 21 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out by using the following reactor.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 0.1 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for

step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of 20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 0.01 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was 20°C, and the reaction time was 0.01 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 71percent Cyclohexyl trifluoroacetate 2percent Cyclohexyl methylthiomethyl ether 4percent Cyclohexanol 19percent; Example 22 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as microreactor for the step (1)) was used. A reaction product solutiondischarging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of 0°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.3 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was 0°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 32percent Cyclohexyl trifluoroacetate 7percent Cyclohexyl methylthiomethyl ether 3percent Cyclohexanol 50percent; Example 23 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agentcontaining liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 0.25 mm, length: 3.2 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 4.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.02 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.6 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, triethylamine was fed at a flow rate of 1.6 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution was determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 55percent Cyclohexyl trifluoroacetate 9percent Cyclohexyl methylthiomethyl ether 7percent Cyclohexanol 27percent; Example 24 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid discharging channel of the microreactor of the step (1) was connected to a reaction product solution introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 4.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for step (1) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.8 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.6 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, triethylamine was fed at a flow rate of 1.6 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle containing an internal standard substance for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 60percent Cyclohexyl trifluoroacetate 7percent Cyclohexyl methylthiomethyl ether 7percent Cyclohexanol 23percent; Example 25 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 4.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.8 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.6 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, triethylamine was fed at a flow rate of 1.6 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 58percent Cyclohexyl trifluoroacetate 11percent Cyclohexyl methylthiomethyl ether 9percent Cyclohexanol 21percent; Example 26 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) using a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel of the microreactor for the step (3) through a connecting SUS tube (inner diameter: 0.25 mm, length: 3.2 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 4.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.8 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.01 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, triethylamine was fed at a flow rate of 1.6 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 52percent Cyclohexyl trifluoroacetate 10percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 29percent; Example 27 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as microreactor for the step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel for step (3) using a connecting SUS tube (inner diameter: 1.0 mm, length: 30 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for the step (1) at a flow rate of 4.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter was fed into the microreactor for step (1) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 0.8 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 2.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.8 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, triethylamine was fed at a flow rate of 1.6 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below.' Cyclohexanone 64percent Cyclohexyl trifluoroacetate 6percent Cyclohexyl methylthiomethyl ether 7percent Cyclohexanol 23percent; Example 28 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM CO., Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel of the microreactor for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.2 mol/liter was fed into the microreactor for step (1) at a flow rate of 1.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.1 mol/liter was fed into the microreactor for step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, triethylamine was fed at a flow rate of 0.8 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 63percent Cyclohexyl trifluoroacetate 6percent Cyclohexyl methylthiomethyl ether 6percent Cyclohexanol 22percent; Example 29 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for step (2) using a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution introducing channel for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.2 mol/liter was fed into the microreactor for step (1) at a flow rate of 1.0 ml/min and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.1 mol/liter was fed into the microreactor for step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0

ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, triethylamine was fed at a flow rate of 0.8 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 60percent Cyclohexyl trifluoroacetate 8percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 24percent; Example 30 In the production of cyclohexanone from cyclohexanol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor. Step (1) A microreactor (manufactured by GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of step (1) was connected to a reaction product solution-introducing channel of the microreactor of step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of step (2) was connected to a reaction product solution-introducing channel of the microreactor for step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 3.0 mol/liter were respectively fed into the microreactor for step (1) at a flow rate of 1.0 ml/min, respectively. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for step (2) and, at the same time, a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for step (3) and, at the same time, triethylamine was fed at a flow rate of 0.8 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Cyclohexanone 62percent Cyclohexyl trifluoroacetate 6percent Cyclohexyl methylthiomethyl ether 8percent Cyclohexanol 21percent; Comparative Example 3 (Batch Synthesis Comparative Example) In an argon gas atmosphere, 2 ml of a dimethyl sulfoxide/methylene chloride solution having a concentration of 4 mol/liter was charged in a Schrenk tube having an inner volume of 30 ml and then cooled to a temperature of -27°C. While stirring this solution using a magnetic stirrer, 2 ml of a trifluoroacetic anhydride/methylene chloride solution having a concentration of 3.0 mol/liter was added dropwise to the solution at an addition rate of 0.2 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To this mixed solution, 4 ml of a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was added dropwise at an addition rate of 0.4 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To the resulting mixed solution, 8 ml of a triethylamine/methylene chloride solution having a concentration of 1.4 mol/liter was added dropwise at an addition rate of 0.8 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the temperature of the resultant mixture solution was returned to room temperature and an internal standard agent was added thereinto, and then the contents of the compounds in the mixed solution were measured by a gas chromatograph internal standard method. The measurement results are shown below. Cyclohexanone 45percent Cyclohexyl trifluoroacetate 11percent Cyclohexyl methylthiomethyl ether 5percent Cyclohexanol 36percent; Comparative Example 4 (Batch Synthesis Comparative Example) In an argon gas atmosphere, 1 ml of a dimethyl sulfoxide/methylene chloride solution having a concentration of 4 mol/liter was charged in a Schrenk tube having an inner volume of 30 ml and then cooled to a temperature of -23°C. While stirring this solution using a magnetic stirrer, 1 ml of a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/liter was added dropwise to the solution at an addition rate of 0.1 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To this mixed solution, 2 ml of a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/liter was added dropwise at an addition rate of 0.2 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To the resulting mixed solution, 4 ml of a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was added dropwise at an addition rate of 0.4 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the temperature of the resultant mixture solution was returned to room temperature and an internal standard agent was added thereinto, and then the contents of the compounds in the mixed solution were measured by a gas chromatograph internal standard method. The measurement results are shown below. Cyclohexanone 16percent Cyclohexyl trifluoroacetate 60percent Cyclohexyl methylthiomethyl ether 2percent Cyclohexanol 14percent; Examples 40 to 41 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of 10°C and -10°C and a reaction time of 0.01 seconds) In each of Examples 40 and 41, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.1 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low temperature water bath at a predetermined temperature described in Table 2. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus using a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed into one of two inlets of the second unit from the reaction solution outlet of the first unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled into sample bottle containing an internal standard substance from the outlet of the third unit. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 2. Table 2 Example No. Starting Substance Reaction temperature (°C) Yield (percent)Product *9 TFA ether *10 MTM ester *11 Non-reacted Starting Substance 40 Cyclohexanol -10 78 5 5 11 41 Cyclohexanol 10 80 4 4 9(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Example 42 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of 0°C and a reaction time of 0.1 seconds) SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.25 mm, length = 6.8 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low temperature water bath at 0°C. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gastight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed from two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed into the second unit through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed into the third unit through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled into sample bottle containing an internal standard substance through the outlet of the third unit. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 3. Table 3 Example No. Starting Substance Reaction temperature (°C) Yield (percent)Product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 42 Cyclohexanol 0 74 4 3 8(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Examples 43 to 46 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -20 to 10°C and a reaction time of 0.5 seconds) In each of Examples 43 to 46, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.5 mm, length = 8.5 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low temperature water bath at a predetermined temperature described in Table 4. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed into one of two inlets of the second unit through the reaction solution outlet of the first unit and a ccylohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed from the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed into one of two inlets of the third unit through the reaction solution outlet of the second unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled into sample bottle containing an internal standard substance through the outlet of the third unit. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 4. Table 4 Example No. Starting Substance Reaction temperature (°C) Yield (percent)Product *9 TFA ester ester *10 MTM ether *11 Non-reacted Starting Substance 43 Cyclohexanol -20 77 5 5 11 44 -10 76 5 5 10 45 0 77 3 3 8 46 10 73 3 4 17(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Example 47 (Example of synthesis of cyclohexane from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of 0°C and a reaction time of 1.2 seconds) SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 1 mm, length = 5 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a low and constant-temperature water bath at 0°C. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 5. Table 5 Example No. Starting Substance Reaction temperature (°C) Yield (percent)Product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 47 Cyclohexanol 0 69 2 2 17(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Example 48 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of 0°C and a reaction time of 1.6 seconds) SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 1 mm, length = 7 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low-temperature water bath at 0°C. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. Using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 6. Table 6 Example No. Starting Substance Reaction temperature (°C) Yield (percent)Product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 48 Cyclohexanol 0 64 4 2 18(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Example 49 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -10°C and a reaction time of 2.4 seconds) SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 1 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low temperature water bath at a predetermined temperature of -10°C. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 7. Table 7 Example No. Starting Substance Reaction temperature (°C) Yield (percent)product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 49 Cyclohexanol -10 80 4 5 10(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Examples 50 to 52 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -20°C, 0°C or 20°C and a reaction time R1 of 0.01 seconds and R2 of 0.02 seconds) In each of Examples 50 to 52, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.1 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 0.25 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low-temperature water bath at a predetermined temperature described in Table 8. Furthermore, a SUS tube (inner diameter =

1.0 mm, length = 100 cm) was connected to the outlet of the apparatus using a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed into the first unit through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.4 mol/L was fed into the third unit through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 8. Table 8 Example No. Starting Substance Reaction temperature (°C) Yield percent)product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 50 Cyclohexanol -20 75 4 3 8 51 0 76 3 3 8 52 20 81 3 2 7(Note) *9: Cyclohexanone *10: Cyclohexyltrifluoro acetate *11: Cyclohexyl methylthiomethyl ether; Example 53 and 54 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -20°C or 0°C and a reaction time of 0.01 seconds) In each of Examples 53 and 54, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.1 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a low and constant-temperature water bath at a predetermined temperature described in Table 9. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus using a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 2.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.0 mol/L were respectively fed into the first unit through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed into the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit and, then, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed into the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 9. Table 9 Example No. Starting Substance Reaction temperature (°C) Yield (percent)product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 53 Cyclohexanol -20 69 8 4 12 54 0 66 8 4 13(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether; Examples 55 and 56 (Example of synthesis of cyclohexanone from cyclohexanol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -20°C or 0°C and a reaction time of 0.01 seconds) In each of Examples 55 and 56, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM Co. (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.1 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a low-temperature water bath at a predetermined temperature shown in Table 10. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus using a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). This connecting portion was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.0 mol/L were respectively fed into the first unit through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed from the reaction solution outlet of the first unit into one of two inlets of the second unit and a cyclohexanol/methylene chloride solution having a concentration of 1.0 mol/L was fed into the second unit through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed from the reaction solution outlet of the second unit into one of two inlets of the third unit, and then a triethylamine/methylene chloride solution having a concentration of 1.5 mol/L was fed into the third unit through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled from the outlet of the third unit into sample bottle containing an internal standard substance. The yield of the product was determined by a GC internal standard method. The reaction results are shown in Table 10. Table 10 Example No. Starting Substance Reaction temperature (°C) Yield (percent)product *9 TFA ester *10 MTM ether *11 Non-reacted Starting Substance 55 Cyclohexanol -20 70 3 4 13 56 0 73 3 4 15(Note) *9: Cyclohexanone *10: Cyclohexyl trifluoroacetate *11: Cyclohexyl methylthiomethyl ether A

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437 Synthesize Find similar

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Rx-ID: 10537610 Find similar reactions

B: 31%

With benzophenone

13.5 h; Irradiation;

Doohan, Roisin A.; Hannan, John J.; Geraghty, Niall W.A.

Organic and Biomolecular Chemistry, 2006 , vol. 4, # 5 p. 942 - 952 Title/Abstract Full Text View citing articles Show Details

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438 Synthesize Find similar

Rx-ID: 11160188 Find similar reactions

Bi, Xian-Jun; Higham, Luke T.; Scott, Janet L.; Strauss, Christopher R.

Australian Journal of Chemistry, 2006 , vol. 59, # 12 art. no. CH06381, p. 883 - 886 Title/Abstract Full Text View citing articles Show Details

in water

T=220°C; retro-Claisen-Schmidt condensation; 8 h; microwave irradiation; Title compound not separated from byproducts.; A

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439 Synthesize Find similar

in water

T=220°C; retro-Claisen-Schmidt

Rx-ID: 11160189 Find similar reactions

Bi, Xian-Jun; Higham, Luke T.; Scott, Janet L.; Strauss, Christopher R.

Australian Journal of Chemistry, 2006 , vol. 59, # 12 art. no. CH06381, p. 883 - 886

condensation; 4 h; microwave irradiation;

Title/Abstract Full Text View citing articles Show Details

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440 Synthesize Find similar Rx-ID: 11160190 Find similar reactions

Bi, Xian-Jun; Higham, Luke T.; Scott, Janet L.; Strauss, Christopher R.

Australian Journal of Chemistry, 2006 , vol. 59, # 12 art. no. CH06381, p. 883 - 886 Title/Abstract Full Text View citing articles Show Details

in water

T=220°C; retro-Claisen-Schmidt condensation; 4 h; microwave irradiation; Title compound not separated from byproducts.; A

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441 Synthesize Find similar

Rx-ID: 11160193 Find similar reactions

Bi, Xian-Jun; Higham, Luke T.; Scott, Janet L.; Strauss, Christopher R.

Australian Journal of Chemistry, 2006 , vol. 59, # 12 art. no. CH06381, p. 883 - 886 Title/Abstract Full Text View citing articles Show Details

in water

T=220°C; retro-Claisen-Schmidt condensation; 6 h; microwave irradiation; Title compound not separated from byproducts.; A

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442 Synthesize Find similar Rx-ID: 11166397 Find similar reactions

With oxygen; chromium colloid/silica T=129.84°C; 2.5 h; Product distribution; Further Variations:Catalysts; A

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Breynaert, Eric; Hermans, Ive; Lambie, Bert; Maes, Guido; Peeters, Jozef; Maes, Andre; Jacobs, Pierre

Angewandte Chemie - International Edition, 2006 , vol. 45, # 45 p. 7584 - 7588 Title/Abstract Full Text View citing articles Show Details

443

With hydrogen

T=199.84 - 249.84°C; P=760.051 Torr; 1 7 h; Conversion of starting material;

Rx-ID: 23685366 Find similar reactions

Council of Scientific and Industrial Research

Patent: US7015359 B1, 2006 ; Location in patent: Page/Page column 4; 5; 6 ;

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Title/Abstract Full Text Show Details

1; 2; 3; 4:

Approximately 230 ml of aqueous solution containing 8.36 g and 49.358 g of Cu(NO3)2.3H2O and Mg(NO3)2.6H2O respectively have been simultaneously precipitated using an aqueous solution containing 1M K2CO3 at a pH of 9. The coprecipitated mass was thoroughly washed with distilled water for three times and filtered. The resultant mass was impregnated with 2 ml of aqueous solution containing 0.53 g of Cr(NO3)3.9H2O. The excess water was evaporated over a hot water bath and the sample was then dried overnight in an oven at 383 K followed by calcination in air at 723 K for 4 h.This catalyst has been tested for furfural hydrogenation and cyclohexanol dehydrogenation simultaneously. In the activity experiment, the molar ratio of furfural and cyclohexanol is maintained at 1:5. Following are the results obtained.EXAMPLE-2The catalyst mentioned in example-1 has been tested for the furfural hydrogenation and cyclohexanol dehydrogenation simultaneously. In the activity experiment, the molar ratio of furfural and cyclohexanol is maintained at 1:3.5. Following are the results obtained.EXAMPLE-3The catalyst mentioned in example-1 has been tested for the furfural hydrogenation and cyclohexanol dehydrogenation simultaneously.In the activity experiment, the molar ratio of furfural and cyclohexanol is maintained at 1:1.7. Following are the results obtained.EXAMPLE-4Approximately 222 ml of ethanol solution containing 8.36 g, 47.45 g and 2.11 g of Cu (NO3)2. 3H2O, Mg (NO3)2. 6H2O and Cr(NO3)3. 9H2O respectively have been simultaneously precipitated using 20 weight percent tetraethylammonium hydroxide solution at a pH of 9. The coprecipitated mass has been thoroughly washed with ethanol for three times and filtered. The sample was then dried in an oven at 383 K for overnight followed by calcination in air at 723 K for 4 h.This catalyst has been tested for the furfural hydrogenation and cyclohexanol dehydrogenation simultaneously. In the activity experiment, the molar ratio of furfural and cyclohexanol is maintained at 1:5. Following are the results obtained A

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444

With sodium hydroxide; water; sodium carbonate

T=60 - 65°C; pH=9.1; Purification / work up; Hide Experimental Procedure

Rx-ID: 23771102 Find similar reactions

DSM IP ASSETS B.V.

Patent: WO2006/79485 A1, 2006 ; Location in patent: Page/Page column 12-14 ; Title/Abstract Full Text Show Details

1; 2:

Example 1; An oxidation mixture (line 1 in figure 1), obtained from an uncatalyzed cyclohexane oxidation, consisted of cyclohexane, 3.2 wt.percent cyclohexylhydroperoxide, 0.5 wt.percent EPO <DP n="14"/>cyclohexanol,0.3 wt.percent cyclohexanone and by-products. Among other by-products, this mixture also contained 0.02 wt.percent CO2 and 0.4 wt.percent mixed organic acids (mono and di- acids ranging from C1 to C6). The oxidation mixture was cooled to 60 0C. Before being fed to a well-stirred neutralization reactor (Ia in figure 1), the cooled oxidation mixture was pre-mixed with an aqueous base solution (line 2 in figure 1) obtained from the plate separator after the cyclohexylhydroperoxide decomposition reactors. The aqueous base solution (line 2) contained 4.1 wtpercent Na2CO3, 1.4 wtpercent NaOH and 14.6 wt.percent sodium-carboxylates of mixed monoacids and di-acids ranging from C1 to C6 acids. Both aqueous and organic solutions were thoroughly mixed in the neutralization reactor (Ia) to obtain a fine organic-aqueous emulsion. The aqueous phase content in this emulsion was 3.8 vol.percent. At the outlet of this reactor, CO2 and organic acids were quantitatively neutralized. The temperature at the outlet of the neutralisation reactor was 650C. After this reactor, the emulsion was supplied to a gravity settler (Ib in figure 1) in which aqueous phase is separated from the emulsion.

The resulting aqueous phase contained 0.3 wt.percent Na2CO3, 3.6 wt.percent NaHCO3 and 21.5 wt.percent Na-carboxylates of mixed monoacids and di-acids ranging from C1 to C6 acids (No NaOH). The amount of stream 2 was chosen such that the pH of the aqueous phase leaving the gravity settler was 9.1. Since the total surplus of aqueous phase in neutralization and decomposition steps is completely purged at this point in the process (purge stream 3), this pH could only be obtained by adjusting the purge stream in a way that 35percent of this stream was sent, together with the separated organic phase, to the first decomposition reactor (stream 4). Thus the amount of the aqueous phase purged (line 3 in figure 1) was 65percent of the aqueous phase leaving the gravity-settler. Thus, 35 percent of the aqueous phase leaving the gravity settler was united with the separated organic phase (line 4 in figure 1). The resulting mixture (line 4) was pre-mixed with an aqueous base solution (line 5) before being fed to the first well-stirred decomposition reactor Ha. The aqueous base solution (line 5) was obtained by mixing a part (line 9) of the aqueous base solution (line 6 in figure 1) obtained from the plate separator after the cyclohexylhydroperoxide decomposition reactors with an aqueous NaOH solution (line 10). An additional aqueous NaOH solution (line 10) was fed to stream 9 to replenish the consumed base in the neutralization and decomposition process. The amount of NaOH fed was such that the NaOH concentration in the aqueous phase at the outlet of the last decomposition reactor was 0.4 mol/liter. Also a small amount of aqueous solution of cobalt sulphate (line 11 in figure 1) was added to the first decomposition reactor as catalyst for the decomposition of cyclohexylhydroperoxide to cyclohexanol EPO <DP n="15"/>and cyclohexanone. The concentration of cobalt in the aqueous phase present in the decomposition reactors was approx. 5 ppm. After the last decomposition reactor the cyclohexylhydroperoxide conversion was complete. Due to the adiabatic temperature rise the temperature at the outlet of the last decomposition reactor was 95 0C. The obtained emulsion at the outlet of this reactor was allowed to settle (lib in figure 1) in 2 consecutive gravity-settlers followed by a plate-separator. After L/L separation the sodium content of the resulting organic phase (line 7 in figure 1) was less than 5 ppm, demonstrating an effective removal of the aqueous phase. The separated organic phase comprised mainly cyclohexane and further 1.7 wt.percent cyclohexanone and 1.7 wt.percent cyclohexanol. This corresponded to a selectivity of the cyclohexylhydroperoxide decomposition reaction of 91.5 percent. The aqueous phase from the L/L separators after the decomposition reactors was largely recycled to the first decomposition reactor (line 9 in figure 1). The size of this stream was controlled such that the decomposition reactors contained approx. 15 vol.percent of aqueous phase. A minor part of the aqueous phase from the LJL separators after the decomposition reactors was fed to the feed, of the neutralization reactor (line 8 of figure 1). In this experiment the total NaOH consumption was 96 kg per ton of produced cyclohexanone+cyclohexanol.; Example 1 was repeated, with the exception that the amount of stream 2 was chosen such that the separated aqueous phase leaving the gravity settler Ib was completely purged (stream 3). Thus, the. separated aqueous phase leaving the gravity settler Ib was not fed to the decomposition Ha. In this experiment the separation of the aqueous and organic phases became very difficult and unfavorable effects occurred in downstream operations (fouling and yield-loss in reboilers). A

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445

A: 3.29%

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Rx-ID: 23859899 Find similar reactions

Korea Research Institute of Chemical Technology

Patent: US5208392 A1, 1993 ; Title/Abstract Full Text Show Details

1:EXAMPLE 1

EXAMPLE 1 To a solution of 1 g of FeCl2.4H2 O and 0.1 g of PdCl2 in 15 ml of water was added 9 g of silica gel (Kiesel gel 60, surface area=426 m2 /g).

The water was then evaporated off to impregnate iron and palladium onto the silica gel. The Fe-Pd/silica was dried at 150° C. for 2 hours and calcined at 400° C. for 3 hours in a flow of N2 (96percent by mole) and H2 (4percent by mole) gaseous mixture. 1 g of the catalyst so obtained was added to a solution of 5 g of cyclohexane in 20 ml of acetone; and, the reaction mixture was stirred at 30° C. under atmospheric pressure for 3 hours, bubbling gases of hydrogen and oxygen into the reation medium at the rate of 20 ml/min, respectively. The yield of cyclohexanol was 2.87percent by mole and the yield of cyclohexanone was 0.42percent by mole. The total yield was 3.29percent by mole.

B: 1.6%

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Miura, Hiroyuki; Watanabe, Hitoshi; Kuwana, Akihiro; Shimamura, Mami; Hirai, Naruhisa

Patent: US2002/169331 A1, 2002 ; Title/Abstract Full Text Show Details

A.1.1:Example A1-1

Example A1-1 To an autoclave (volume 1L) made of titanium and equipped with a condenser and a pressure-controller, were added 50 g (0.594 mol) of cyclohexane, 9.692 g (0.059 mol) of N-hydroxyphthalimide, 0.296 g (0.0012 mol) of cobalt acetate (II) tetrahydrate and 400 g of acetonitrile, and heated to elevate a temperature under applied nitrogen-pressure (33 kgf/cm2; 3.24 MPa) with stirring. At a temperature of 75° C. was steadied, and a reaction was conducted for 4 hours under applied pressure (40 kgf /cm2; 3.92 MPa) with flowing air. The system was substituted with nitrogen to be cooled. The reaction mixture was analyzed by gas chromatography and high performance liquid chromatography, and, as a result, the conversion of cyclohexane was 19.5percent, is cyclohexanone and cyclohexanol were formed in yield 14.5percent (selectivity 74.4percent) and yield 1.6percent (selectivity 8.2percent), respectively.

Purification / work up; Hide Experimental Procedure

BASF Corporation

Patent: US2006/189829 A1, 2006 ; Location in patent: Page/Page column 6-8 ; Title/Abstract Full Text Show Details

The method of minimizing aldehyde-based impurities in the process stream including the alkanone and the aldehyde-based impurities includes introducing the amine into the process stream to form the heavy product. The amine interacts with the alkanone and the aldehyde-based impurities to form the heavy product, and it is contemplated that more than one heavy product may be formed. The heavy product is separated from the alkanone, preferably through distillation. According to the subject invention, the amines were added to 50:50 mixtures of cyclohexyl ketone and cyclohexyl alcohol including n-hexanal. The amines interacted with the n-hexanal to form the imine. The cyclohexyl ketone interacted with the n-hexanal, in the presence of the amine, to form 2-hexylidene-cyclohexanone. TABLE 1 n-Hexanal Reduction as a Function of DETA Added 4.6 Equivalents of DETA 8.8 equivalents of DETA 13.4 equivalents of DETA Added; pH = 4.6 Added; pH = 4.5 Added; pH = 4.5 n- percent n- n- percent n- n- percent n- Hexanal Time Hexanal Hexanal Time Hexanal Hexanal Time Hexanal [ppm] (h) Reduction (ppm) (h) Reduction (ppm) (h) Reduction 415 Before 0 415 Before 0 415 Before 0 Addition Addition Addition 53 0.1 87.2 35 0.1 91.6 26 0.1 93.7 50 0.5 88 31 0.5 92.5 22 0.5 94.7 49 12 88.2 29 12 93 20 12 95.2 Table 1 shows n-hexanal reduction in a 50:50 mixture of cyclohexyl ketone and cyclohexyl alcohol including 415 parts per million of n-hexanal at time 0. A pH of the mixture was adjusted with addition of formic acid. Table 1 also shows DETA added in three quantities to identical samples of the mixture. The samples were stirred at room temperature and gas chromatography measurements of the samples were taken at times 0, 0.1, 0.5, and 12 hours after addition of DETA. TABLE 2 n-Hexanal Reduction as a Function of DETA Added DETA Added; pH = 8; Room Temperature; n-Hexanal [ppm] 1 Molar 2 Molar 3 Molar 4 Molar 5 Molar Time (h) Equiv. Equiv. Equiv. Equiv. Equiv. Before 324 324 324 324 324 Addition 0.1 123 105 94 88 84 0.5 114 100 89 84 80 1 106 93 86 78 79 12 86 78 77 72 70 Table 2 shows n-hexanal reduction in a 50:50 mixture of cyclohexyl ketone and cyclohexyl alcohol including 324 parts per million of n-hexanal at time 0. A pH of the mixture was unadjusted at 8. Table 2 also shows DETA added in five quantities to five identical samples in 1, 2, 3, 4 and 5 molar equivalents to n-hexanal. The samples were stirred at room temperature and gas chromatography measurements of the samples were taken at times 0, 0. 1, 0.5, 1, and 12 hours after addition of DETA. TABLE 3 n-Hexanal Reduction as a Function of DETA Added DETA Added; pH = 4.5; Room Temperature; n-Hexanal [ppm] 1 Molar 2 Molar 3 Molar 4 Molar 5 Molar Time (h) Equiv. Equiv. Equiv. Equiv. Equiv. Before 305 305 305 305 305 Addition 0.1 48 34 35 30 32 0.5 38 36 34 32 29 1 38 35 33 31 30 12 36 32 27 23 22 Table 3 shows n-hexanal reduction in a 50:50 mixture of cyclohexyl ketone and cyclohexyl alcohol including 305 parts per million of n-hexanal at time 0. A pH of the mixture was adjusted to 4.5 with addition of formic acid. Table 3 also shows DETA added in five quantities to five identical samples in one, two, three, four, and five molar equivalents to n-hexanal. The samples were stirred at room temperature and gas chromatography measurements of the samples were taken at times 0, 0.1, 0.5, 1, and 12 hours after addition of DETA. TABLE 4 n-Hexanal Reduction as a Function of TETA Added TETA Added; pH = 8; Room Temperature; n-Hexanal [ppm] Time 1 Molar 2 Molar 3 Molar 4 Molar 5 Molar (h) Equiv. Equiv. Equiv. Equiv. Equiv. Before 324 324 324 324 324 Addition 0.1 198 142 125 102 94 0.5 174 127 108 95 88 1 176 115 101 92 82 12 194 131 96 83 87 Table 4 shows n-hexanal reduction in a 50:50 mixture of cyclohexyl ketone and cyclohexyl alcohol including 324 parts per million of n-hexanal at time 0. A pH of the mixture was unadjusted at 8. Table 4 also shows TETA added in five quantities to five identical samples in 2, 3, 4 and 5 molar equivalents to n-hexanal. The samples were stirred at room temperature and gas chromatography measurements of the samples were taken at times 0, 0.1, 0.5, 1, and 12 hours after addition of TETA. TABLE 5 n-Hexanal Reduction as a Function of TETA Added TETA Added; pH = 4.5; Room Temperature; n-Hexanal [ppm] Time 1 Molar 2 Molar 3 Molar 4 Molar 5 Molar (h) Equiv. Equiv. Equiv. Equiv. Equiv. Before 318 318 318 318 318 Addition 0.1 47 38 31 32 27 0.5 31 35 30 30 25 1 33 30 28 30 25 12 45 34 27 24 26 Table 5 shows n-hexanal reduction in a 50:50 mixture of cyclohexyl ketone and cyclohexyl alcohol including 318 parts per million of n-hexanal at time 0. A pH of the mixture was adjusted to 4.5 with addition of formic acid. Table 5 also shows TETA added in five quantities to five identical samples in 1, 2, 3, 4 and 5 molar equivalents to n-hexanal. The samples were stirred at room temperature and gas chromatography measurements of the samples were taken at times 0, 0. 1, 0.5, 1, and 12 hours after addition of TETA. TABLE 6 n-Hexanal Reduction After 60 Minutes Reflux as a Function of Amine Added pH = 3.1 pH = 4.5 percent n- percent n- Amine (3 molar Initial Final Hexanal Initial Final Hexanal equiv.) ppm ppm Reduct. ppm ppm Reduct. Hexamethylene 320 74 77 360 0 100 Diamine Cyclohexylamine 283 94 67 254 44 83 Hexylamine 296 48 84 312 84 77 Phenylhydrazine 292 224 24 307 218 29 Isobutylamine 270 64 69 273 23 92 Octylamine 276 200 28 273 206 25 Nonylamine 208 178 80 209 34 84 DETA 250 18 93 260 15 94 TETA 344 24 93 375 21 95 Table 6 shows percent n-hexanal reduction in 50:50 mixtures of cyclohexyl ketone and cyclohexyl alcohol including n-hexanal at time 0. A pH of the mixtures was adjusted to 3.1 or 4.5 with addition of formic acid. Table 6 also shows amines added to nine samples in 3 molar equivalents to nhexanal. Gas chromatography measurements of the samples were taken before and after 60 minutes of reflux of the samples. TABLE 7 n-Hexanal Reduction After 60 Minutes Reflux as a Function of Amine Added pH = 5.6 pH = 8 percent n- percent n- Amine (3 molar Initial Final Hexanal Initial Final Hexanal equiv.) ppm ppm Reduct. ppm ppm Reduct. Hexamethylene 305 153 50 280 213 24 Diamine Cyclohexylamine 207 104 50 191 185 3 Hexylamine 322 79 74 300 281 73 Phenylhydrazine 342 303 12 324 323 0 Isobutylamine 285 81 76 246 128 48 Octylamine 306 218 29 312 245 22 Nonylamine 207 35 84 210 131 38 DETA 255 20 92 251 25 90 TETA 301 17 95 270 31 89 Table 7 shows percent nhexanal reduction in mixtures of 50:50 mixtures of cyclohexyl ketone and cyclohexyl alcohol including n-hexanal. A pH of the mixtures was adjusted to 5.6 or 8 with addition of formic acid. Table 7 also shows amines added to nine samples in 3 molar equivalents to n-hexanal. Gas chromatography measurements of the samples were taken before and after 60 minutes of reflux of the samples. TABLE 8 n-Hexanal and Cyclohexyl Ketone Reduction as a Function of Amine Type percent Cyclic percent n- Boiling Alkanone Hexanal Amine FW Pt (° C.) Reduction Reduction Cyclohexyl N/A N/A <5percent 0 Ketone + Cyclohexyl Alcohol Diphenylamine 169.23 302 0 0 Melamine 126.12 N/A 0 4 Aniline 93.13 184 0 5 Cyclohexylamine 99.18 134 <5percent 5 Acetamide 59.07 221 0 6 Octylamine 129.25 175-177 <5percent 22 Hexamethylene 116.21 204 <5percent 24 Diamine Nonylamine 143.27 201 <5percent 38 Isobutylamine 73.14 64-71 <5percent 48 Hexylamine 101.19 131-132 <5percent 73 TETA 146.24 266-267 0 89 DETA 103.17 199-209 0 90 Table 8 shows percent n-hexanal and cyclohexyl ketone reduction in 50:50 mixtures of cyclohexyl ketone and cyclohexyl alcohol including 300 parts per million n-hexanal. Table 8 shows the amines added to twelve samples in 3 molar equivalents to n-hexanal. The samples were refluxed for thirty minutes. After thirty minutes of reflux of the samples, gas chromatography measurements of the samples were taken. Hide Details

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Miura, Hiroyuki; Watanabe, Hitoshi; Kuwana, Akihiro; Shimamura, Mami; Hirai, Naruhisa

Patent: US2002/169331 A1, 2002 ; Title/Abstract Full Text Show Details

B.5:Example B5

From the reaction mixture, cyclohexane was distilled off, and to the reaction mixture was added 30 mL of 2N (2 mol/L) sodium hydroxide aqueous solution. After mixing at 97° C. for 1 hour and standing for 1 hour, an aqueous phase and an organic phase were separated. The aqueous and organic phases were analyzed by gas chromatography and liquid chromatography, and, as a result, the recover ratio of cyclohexanol into the organic phase was 85percent, the recover ratio of cyclohexanone into the organic phase was 90percent, the extraction ratio of phthalimide (conversion into sodium phthalate) into the aqueous phase (on basis of the amount of phthalimide in the reaction mixture) was 89percent and the extraction rario of N-cyclohexyloxyphthalimide (conversion into sodium phthalate) into the aqueous phase (on basis of the amount of N-cyclohexylphthalimide) was 90percent.

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Sun Company, Inc. (R and M)

Patent: US5672778 A1, 1997 ; Title/Abstract Full Text Show Details

8:Example 8

Example 8 When a catalytic quantity of phthalocyanotochromium chloride is added to a dry cyclohexane oxidate rich in cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone are formed in total molar excess over the cyclohexyl hydroperoxide in the original feed.

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Barton; Derek H. R.

Patent: US5756852 A1, 1998 ; Title/Abstract Full Text Show Details

4:EXAMPLE 4

EXAMPLE 4 Example 3 was repeated except that CuCl (2.5 mmol) was substituted for Fe(ClO4)2 and the amount of picolinic acid was increased to 6 mmol. The yields obtained were cyclohexanone (2.21 mmol) and cyclohexanol (2.86 mmol).

Hyosung Corporation

Patent: US6245907 B1, 2001 ;

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Title/Abstract Full Text Show Details

C.1:COMPARATIVE EXAMPLE 1

400 ppm of methylcyclopentanol was added to 500 g of cyclohexanol free of methylcyclopentanol and methylcyclopentanone and the dehydrogenation process of Example 4 was repeated. The mixture of the cyclohexanol and the cyclohexanone obtained by the preceding dehydrogenation was separated by the same method as Example 1. The conversion of cyclohexanone was 53percent, and the purity of the cyclohexanone obtained was 99.4percent, and methylcyclopentanone content of cyclohexanone was 610 ppm, and methylcyclopentanol content of cyclohexanol was less than 10 ppm. A

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446 Synthesize Find similar Rx-ID: 24790780 Find similar reactions

With acetylperoxyborate; FeAlPO in water

T=110°C; pH=5.2; 8 - 16 h; Product distribution / selectivity; Hide Experimental Procedure

U.S. BORAX, INC.

Patent: WO2006/43075 A1, 2006 ; Location in patent: Page/Page column 11-13 ; Title/Abstract Full Text Show Details

Two runs (each with different reaction times) were carried out as follows.Solid acetylperoxyborate (3.49g) prepared according to US 5462692 and capable of liberating peracetic acid (0.70Ig) and hydrogen peroxide (0.045g) when dissolved in water, was mixed with double-distilled water (20ml). The resulting solution was fed EPO <DP n="13"/>slowly by a syringe pump'to a stirred reactor containing cyclohexane (2.5g) and FeAlPO-31 catalyst (0.25g), while the temperature was maintained at 1 10°C. This corresponds to a cyclohexane to peracetic acid molar ratio of 3:1.The reaction products were analysed by gas chromatography (GC, Varian Model 3400 CX) employing a HP Innovax Column (30m x 0.53 mm x 0.1 μm) and flame ionisation detector using a variable ramp temperature program from 650C to 220°C.The identity of each product was first confirmed using authenticated standards and their individual response factors were determined using a suitable internal standard (calibration method).The identity of the products was also confirmed by liquid crystal mass spectrometry using an LCMS-QP8000 (Shimadzu).The reaction pH was 5.2.One run was conducted for 16 hours. In this case the results were as follows:Conversion of cyclohexane to oxidised products was calculated to be 29.5percent .Product selectivity was as follows: * Other acids (here and below) = succinic, glutaric and valeric acids.One run was conducted for 8 hours. In this case the results were as follows: EPO <DP n="14"/>Conversion of cyclohexane to oxidised products was calculated to be 24.7percent.Product selectivity was as follows: A

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447 Synthesize Find similar

Rx-ID: 3863382 Find similar reactions

A: 4% B: 85%

With sodium hydroxide; sodium chlorite; tetra(nbutyl)ammonium hydrogensulfate in dichloromethane

8 h; Ambient temperature;

Ballini, Roberto; Petrini, Marino

Tetrahedron Letters, 1989 , vol. 30, # 39 p. 5329 - 5332 Title/Abstract Full Text View citing articles Show Details

A: 4% B: 85%

With sodium hydroxide; sodium chlorite; tetra(nbutyl)ammonium hydrogensulfate in dichloromethane

8 h; Ambient temperature;

Ballini, Roberto; Petrini, Marino

Tetrahedron Letters, 1989 , vol. 30, # 39 p. 5329 - 5332 Title/Abstract Full Text View citing articles Show Details

A: 37 % Turnov. B: 7 % Turnov.

With sodium hydroxide; sodium chloride in dichloromethane; water

T=8 - 10°C; Electrochemical reaction;

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

448 Synthesize Find similar Rx-ID: 8867262 Find similar reactions

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A: 90.4%

With boron(III) phosphate in benzene

T=300°C; Beckmann rearrangement; P=750.06 Torr; 2.66667 h; Product distribution; Further Variations:CatalystsSolvents;

Tsuji, Hideto; Setoyama, Tohru

Chemistry Letters, 2005 , vol. 34, # 9 art. no. CL-050587, p. 1232 - 1233 Title/Abstract Full Text View citing articles Show Details

With Hβ(10)500 in benzene

T=300°C; Product distribution; Further Variations:CatalystsSolventsTemperatures;

Ouyang, Kuang-Hao; Chen, Chih-Wei; Ko, An-Nan

Journal of the Chinese Chemical Society, 2001 , vol. 48, # 2 p. 137 - 144 Title/Abstract Full Text View citing articles Show Details

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449 Synthesize Find similar

Rx-ID: 9457415 Find similar reactions

A: 4 % Chromat. B: 10 % Chromat. C: 49 % Chromat.

With triethylamine in acetone

T=20°C; 10 h; Irradiation;

Horiuchi, C. Akira; Takeda, Akinori; Chai, Wen; Ohwada, Kishoh; Ji, Shun-Jun; Takahashi, T. Tomoyoshi

Tetrahedron Letters, 2003 , vol. 44, # 52 p. 9307 - 9311 Title/Abstract Full Text View citing articles Show Details

A: 4 % Chromat. B: 10 % Chromat. C: 49 % Chromat.

With air; triethylamine in acetone

10 h; Irradiation;

Chai, Wen; Takeda, Akihiro; Hara, Makoto; Ji, Shun-Jun; Horiuchi, C. Akira

Tetrahedron, 2005 , vol. 61, # 9 p. 2453 - 2463 Title/Abstract Full Text View citing articles Show Details

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450 Synthesize Find similar Rx-ID: 9875474 Find similar reactions

B: 7%

Stage #1: With 2-hydroxy-1,3-isoindolinedione; 2,2'-azobisisobutyronitrile; oxygen in acetonitrile

T=75°C; P=760 Torr; 3 h; Stage #2: With sulfuric acid in acetonitrile

T=25°C; 2 h; Further byproducts given; A

Aoki, Yasuhiro; Sakaguchi, Satoshi; Ishii, Yasutaka

Tetrahedron, 2005 , vol. 61, # 22 p. 5219 - 5222 Title/Abstract Full Text View citing articles Show Details

451 Synthesize Find similar Rx-ID: 9876230 Find similar reactions

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Stage #1: With 2-hydroxy-1,3-isoindolinedione; oxygen

T=100°C; P=760 Torr; 3 h; Stage #2: With sulfuric acid

T=20°C; 2 h;

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Aoki, Yasuhiro; Sakaguchi, Satoshi; Ishii, Yasutaka

Tetrahedron, 2005 , vol. 61, # 22 p. 5219 - 5222 Title/Abstract Full Text View citing articles Show Details

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452 Synthesize Find similar

A: 96.1 % Turnov.

With silicalite-1 treated with hydrofluoric acid in ethanol

T=370°C; P=750.06 Torr; Product distribution; Further Variations:Catalystsconversion with reaction time;

Rx-ID: 9939216 Find similar reactions

Tao, Weichuan; Mao, Dongsen; Xia, Jianchao; Chen, Qingling; Hu, Ying

Chemistry Letters, 2005 , vol. 34, # 4 p. 472 - 473 Title/Abstract Full Text View citing articles Show Details

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453 Synthesize Find similar

A: 52%

With FeBr2 in tetrahydrofuran

T=20°C; 16 h;

Rx-ID: 9962984 Find similar reactions

Tang, Yuanqing; Dong, Yuxiang; Wang, Xiaofang; Sriraghavan, Kamaraj; Wood, James K.; Vennerstrom, Jonathan L.

Journal of Organic Chemistry, 2005 , vol. 70, # 13 p. 5103 - 5110 Title/Abstract Full Text View citing articles Show Details

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454 Synthesize Find similar

A: 5% B: 5% C: 88%

With samarium diiodide; water in tetrahydrofuran

T=20°C; 0.166667 h;

Rx-ID: 10046389 Find similar reactions

Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira

Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 8 p. 1017 - 1020 Title/Abstract Full Text View citing articles Show Details

455 Synthesize Find similar

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With 2-hydroxy-1,3isoindolinedione; bromine; oxygen; 1,10-phenanthroline monohydrate in tetrachloromethane; acetonitrile

T=99.85°C; P=2250.18 Torr; 5 h;

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Rx-ID: 10117666 Find similar reactions

Tong, Xinli; Xu, Jie; Miao, Hong

Advanced Synthesis and Catalysis, 2005 , vol. 347, # 15 p. 1953 - 1957 Title/Abstract Full Text View citing articles Show Details

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456 Synthesize Find similar

A: 45% B: 36% C: 7%

With boron trifluoride diethyl etherate in diethyl ether

T=20°C; 1 h;

Rx-ID: 10122409 Find similar reactions

Terent'ev; Kutkin; Platonov; Starikova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 5 p. 1214 - 1218 Title/Abstract Full Text View citing articles Show Details

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457 Synthesize Find similar

With ozone; Titanium(IV) oxide

T=80°C; 2 h; UV-irradiation; Product distribution; Further Variations:time;

Rx-ID: 10153232 Find similar reactions

Pillai, Unnikrishnan R.; Sahle-Demessie, Endalkachew

Chemical Communications, 2005 , # 17 p. 2256 - 2258 Title/Abstract Full Text View citing articles Show Details

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458 Synthesize Find similar

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Rx-ID: 10153575 Find similar reactions

A: 20 % Turnov. B: 5 % Turnov. C: 15 % Turnov.

With sodium methylate

T=8 - 10°C; Electrochemical reaction;

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

459 Synthesize Find similar

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Rx-ID: 10153576 Find similar reactions

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A: 27 % Turnov. B: 8 % Turnov. C: 18 % Turnov.

With sodium hydroxide; water in dichloromethane

T=8 - 10°C; Electrochemical reaction;

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

A: 15 % Turnov. B: 10 % Turnov. C: 20 % Turnov.

With sodium hydroxide; water in dichloromethane

T=8 - 10°C; Electrochemical reaction;

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

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460 Synthesize Find similar

A: 54 % Turnov. B: 7 % Turnov.

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With sodium hydroxide; water in dichloromethane

T=8 - 10°C; Electrochemical reaction;

Rx-ID: 10153577 Find similar reactions

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

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461 Synthesize Find similar

A: 51 % Turnov. B: 17 % Turnov.

With sodium hydroxide; sodium nitrite in dichloromethane; water

T=8 - 10°C; Electrochemical reaction;

Rx-ID: 10153578 Find similar reactions

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

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462 Synthesize Find similar

Rx-ID: 10153579

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A: 85 % Turnov. B: 2 % Chromat.

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With sodium hydroxide; sodium bromide in dichloromethane; water

T=8 - 10°C; Electrochemical reaction;

Find similar reactions

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

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463 Synthesize Find similar

A: 80 % Turnov. B: 3 % Chromat.

With sodium hydroxide; sodium iodide in dichloromethane; water

T=8 - 10°C; Electrochemical reaction;

Rx-ID: 10153580 Find similar reactions

Ilovaisky; Merkulova; Ogibin; Nikishin

Russian Chemical Bulletin, 2005 , vol. 54, # 7 p. 1585 - 1592 Title/Abstract Full Text View citing articles Show Details

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464 Synthesize Find similar

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Rx-ID: 23319044 Find similar reactions

A: 19.95 %Chromat. B: 1.07 %Chromat. C: 0.74 %Chromat. D: 18.19 %Chromat. E: 1.6 %Chromat. F: 0.19 %Chromat. G: 0.46 %Chromat.

With sodium carbonate

T=200°C; liquid phase pyrolysis oilized reaction; P=37503.8 Torr; 1 h; Product distribution / selectivity;

Victor Co. of Japan Ltd.

Patent: JP2005/112781 A, 2005 ; Location in patent: Page/Page column 7-8 ; Title/Abstract Full Text Show Details

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465 Synthesize Find similar

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Rx-ID: 23578411 Find similar reactions

With water

T=400°C; 0.05 - 1 h; Product distribution / selectivity;

Toyota Motor Corporation; Genesis Research Institute, Inc.

Patent: JP2005/225826 A, 2005 ; Location in patent: Page/Page column 25; 52 ; Title/Abstract Full Text Show Details

466 Synthesize Find similar

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Rx-ID: 9523356 Find similar reactions

With oxygen

T=-48.15°C; P=50 Torr; KineticsActivation energy; Further Variations:TemperaturesPressures;

Zhang, Lei; Kitney, Katherine A.; Ferenac, Melissa A.; Deng, Wei; Dibble, Theodore S.

Journal of Physical Chemistry A, 2004 , vol. 108, # 3 p. 447 - 454 Title/Abstract Full Text View citing articles Show Details

467 Synthesize Find similar

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Rx-ID: 9583244 Find similar reactions

With toluene-4-sulfonic acid

T=89.85°C; P=45003.6 Torr; Equilibrium constant; Further Variations:Pressures;

Abbott, Andrew P.; Corr, Stuart; Durling, Nicola E.; Hope, Eric G.

Journal of Physical Chemistry B, 2004 , vol. 108, # 15 p. 4922 - 4926 Title/Abstract Full Text View citing articles Show Details

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468 Synthesize Find similar

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Rx-ID: 9665026 Find similar reactions

With oxygen; butanone; molecular sieve

T=99.85°C; 12 h; atmospheric pressure; Product distribution; Further Variations:Reagents;

Mohapatra, Susanta K.; Selvam, Parasuraman

Chemistry Letters, 2004 , vol. 33, # 2 p. 198 - 199 Title/Abstract Full Text View citing articles Show Details

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469 Synthesize Find similar

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With silica gel; 1-n-butyl-3-methylimidazolium tetrafluoroborate in water

T=20°C; Product distribution; Further Variations:CatalystsSolvents; A

Rx-ID: 9674209 Find similar reactions

Li, Dongmei; Shi, Feng; Deng, Youquan

Tetrahedron Letters, 2004 , vol. 45, # 36 p. 6791 - 6794 Title/Abstract Full Text View citing articles Show Details

470 Synthesize Find similar

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With [bis(acetoxy)iodo]benzene; iodine in dichloromethane

T=20°C; 0.166667 h; UV-irradiation;

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Rx-ID: 9723365 Find similar reactions

Antunes, Carla S. Aureliano; Bietti, Massimo; Lanzalunga, Osvaldo; Salamone, Michela

Journal of Organic Chemistry, 2004 , vol. 69, # 16 p. 5281 - 5289 Title/Abstract Full Text View citing articles Show Details

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471 Synthesize Find similar

With [bis(acetoxy)iodo]benzene; iodine in dichloromethane

T=20°C; 0.166667 h; UV-irradiation;

Rx-ID: 9723366 Find similar reactions

Antunes, Carla S. Aureliano; Bietti, Massimo; Lanzalunga, Osvaldo; Salamone, Michela

Journal of Organic Chemistry, 2004 , vol. 69, # 16 p. 5281 - 5289 Title/Abstract Full Text View citing articles Show Details

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472 Synthesize Find similar

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Rx-ID: 9810677 Find similar reactions

With sodium nitrite

T=0 - 20°C; 5 h;

Matsumura, Yoshihiro; Yamamoto, Yutaka; Moriyama, Noriaki; Furukubo, Shigeru; Iwasaki, Fumiaki; Onomura, Osamu

Tetrahedron Letters, 2004 , vol. 45, # 44 p. 8221 - 8224 Title/Abstract Full Text View citing articles Show Details

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473 Synthesize Find similar

Rx-ID: 10018212 Find similar reactions

A: 82 % Chromat. B: 7 % Chromat.

With chlorine dioxide in acetonitrile

T=35°C; 12 h; Kinetics; Further Variations:TemperaturesSolvents;

Abdrakhmanova; Kabal'nova; Rol'nik; Yagafarova; Shereshovets

Russian Chemical Bulletin, 2004 , vol. 53, # 8 p. 1755 - 1760 Title/Abstract Full Text View citing articles Show Details

A: 82 % Chromat. B: 7 % Chromat.

With chlorine dioxide in acetonitrile

T=35°C; 12 h; Title compound not separated from byproducts;

Abdrakhmanova; Kabal'nova; Rol'nik; Yagafarova; Shereshovets

Russian Chemical Bulletin, 2004 , vol. 53, # 8 p. 1755 - 1760 Title/Abstract Full Text View citing articles Show Details

474 Synthesize Find similar

Rx-ID: 10076207 Find similar reactions

With hydrogen in toluene

T=20°C; P=760 Torr;

Orlova; Stromnova; Kazyul'kin; Boganova; Kochubey; Novgorodov

Russian Chemical Bulletin, 2004 , vol. 53, # 4 p. 819 - 824 Title/Abstract Full Text View citing articles Show Details

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475 Synthesize Find similar

With dihydrogen peroxide

T=20°C; pH=10; Kinetics;

Rx-ID: 11016268 Find similar reactions

Huber, Marc M.; Ternes, Thomas A.; Von Gunten, Urs

Environmental Science and Technology, 2004 , vol. 38, # 19 p. 5177 - 5186 Title/Abstract Full Text View citing articles Show Details

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476 Synthesize Find similar Rx-ID: 22958296 Find similar reactions

With oxygen

Chu, Luis A.; Fodor, Ludovic; Valdez, David L.

Patent: US2004/92767 A1, 2004 ; Location in patent: Page 1 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

contacting cyclohexane with an oxygen-containing gas to produce an oxidation product that comprises cyclohexane, cyclohexyl hydoperoxide, cyclohexanone, cyclohexanol, hydroperoxyhexanoic acid, adipic acid, hydroxyhexanoic acid and water; A

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477 Synthesize Find similar Rx-ID: 23048109 Find similar reactions

With oxygen; alumina catalyst containing tungsten oxide T=160°C; Gas phase; Hide Experimental Procedure

Suzuki, Ken; Nagahara, Hajime

Patent: US2004/176592 A1, 2004 ; Location in patent: Page 13-14 ;

Title/Abstract Full Text Show Details

1.4:4) Step of Subjecting Cyclohexylamine to Partial Oxidation to Obtain Cyclohexanone Oxime

The solid catalyst was charged into a tubular reactor having an inner diameter of 30 mm, which was made of stainless steel. The tubular reactor containing the solid catalyst was placed in a furnace. The reactor was purged with nitrogen gas, and then heated to 160° C. Then, a reaction gas containing 6.0percent by volume of cyclohexylamine and 7.0percent by volume of oxygen was introduced into the reactor at an LHSV of 0.1 liter per hour per liter of the catalyst, thereby effecting a reaction. Samples of the resultant gaseous reaction mixture were automatically withdrawn from the reactor, and analyzed by GC. The results of the analysis of the samples by GC showed that, when the reaction became steady, the conversion of cyclohexylamine was 29.2percent, and the selectivity for cyclohexanone oxime was 87.5percent. Further, it was found that, as by-products, cyclohexanone (selectivity: 2.1percent), nitrocyclohexane (selectivity: 1.8percent), N-cyclohexylidenecyclohexylamine (selectivity: 6.6percent), dicyclohexylamine (selectivity: 0.9percent) and the like were generated. A

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478

Rx-ID: 25782951 Find similar reactions

Nippon Shokubai Co., Ltd.

Patent: EP1398080 A1, 2004 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

C.7:[Baeyer-Villiger oxidation reaction]

Examples 29 to 30 and Comparative Example 7 [Baeyer-Villiger oxidation reaction] The hydrogen peroxide oxidation of cyclohexanone and cyclobutanone was carried out under the following conditions using the catalysts obtained in Preparation Method 6. The results are shown in Table 6. Substrate(cyclohexanone, cyclobutanone): 1 mmol 60percent aqueous hydrogen peroxide: 1 mmol Benzonitrile: 2 mL A

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479

Rx-ID: 25783206 Find similar reactions

Ring, Sven; Kaufmann, Guenter; Wyrwa, Ralf; Elger, Walter

Patent: US2004/24231 A1, 2004 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

1:17β-Hydroxy-17α-trifluoromethyl-androst-4-en-3-one

12 g of 3β-acetoxy-17β-trimethylsilyloxy-17α-trifluoromethyl-androst-5-ene is dissolved in 100 ml of THF and mixed at room temperature with 20 ml of 30percent hydrofluoric acid. After 3 hours, it is poured into 200 ml of 12percent ammonia solution, extracted with 3*100 ml of ethyl acetate, the organic extracts are dried and concentrated by evaporation. 9 g of 3β-acetoxy-17β-hydroxy-17α-trifluoromethyl-androst-5-ene, which is dissolved in 300 ml of methanol and mixed with 6 g of potassium hydroxide, is obtained. After 30 minutes of stirring at room temperature, it is neutralized with 2N hydrochloric acid, and the methanol is drawn off in a vacuum. The residue is extracted with 4*100 ml of ethyl acetate, and the combined organic extracts are dried and concentrated by evaporation. 7.5 g of 3β,17β-dihydroxy-17α-trifluoromethyl-androst-5-ene, which is refluxed with 80 ml of cyclohexanone, 5 g of aluminum triisopropanolate and 250 ml of toluene for 3 hours, is obtained.

480 Synthesize Find similar

97%

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Rx-ID: 2068873 Find similar reactions

With ammonium chlorochromate on aluminum oxide in diethyl ether

0.5 h; Heatingvarious conditions;

Zhang, Gui-Sheng; Gong, Hui; Yang, De-Hong; Chen, Mi-Feng

Synthetic Communications, 1999 , vol. 29, # 7 p. 1165 - 1170 Title/Abstract Full Text View citing articles Show Details

92%

With Zr(HSO4)4; silica gel in hexane

T=20°C; 0.3 h;

Shirini; Zolfigol; Safari; Mohammadpoor-Baltork; Mirjalili

Tetrahedron Letters, 2003 , vol. 44, # 40 p. 7463 - 7465 Title/Abstract Full Text View citing articles Show Details

90%

With water; silica gel; silicon tetrabromide in tetrachloromethane

T=20°C; 0.233333 h;

De, Surya Kanta

Tetrahedron Letters, 2003 , vol. 44, # 50 p. 9055 - 9056 Title/Abstract Full Text View citing articles Show Details

Hide Details

85%

With K-10 clay-supported Fe(NO3)3 ("clayfen" reagent) in dichloromethane

1.16667 h; Ambient temperature;

Laszlo, Pierre; Polla, Eugenio

Synthesis, 1985 , # 4 p. 439 - 440 Title/Abstract Full Text Show Details

85%

With bis(trimethylsilyl)chromate; Montmorillonite K10

Solid phase reaction; Cleavage; 0.0333333 h; microwave irradiation;

Heravi, Majid M.; Tajbakhsh, Mahmood; Bakooie, Hamid; Ajami, Dariush

Monatshefte fur Chemie, 1999 , vol. 130, # 7 p. 933 - 936 Title/Abstract Full Text View citing articles Show Details

80%

With ammonium dichromate(VI); water; silica gel; zirconium tetrachloride

T=80°C; 0.25 h;

Shirini; Zolfigol; Pourhabib

Synthetic Communications, 2002 , vol. 32, # 18 p. 2837 - 2841 Title/Abstract Full Text View citing articles Show Details

72%

With NaBiO3; silica gel

Hydrolysis; 0.133333 h; microwave irradiation, solid phase reaction;

Mitra, Alok Kumar; De, Aparna; Karchaudhuri, Nilay

Journal of Chemical Research - Part S, 1999 , # 5 p. 320 - 321 Title/Abstract Full Text View citing articles Show Details

71%

With copper dichloride in acetonitrile

0.25 h; Heating;

Ram, Ram N.; Varsha, Kiran

Tetrahedron Letters, 1991 , vol. 32, # 41 p. 5829 - 5832 Title/Abstract Full Text View citing articles Show Details

71%

With polumer-supported phenyliodine bis(trifluoroacetate); water in tetrahydrofuran

0.833333 h;

Chen; Cheng

Synthetic Communications, 2001 , vol. 31, # 24 p. 3847 - 3850 Title/Abstract Full Text View citing articles Show Details

70%

With water; antimony trichloride

Substitution; 0.00333333 h; microwave irradiation;

Mitra, Alok Kumar; De, Aparna; Karchaudhuri, Nilay

Synthetic Communications, 2000 , vol. 30, # 9 p. 1651 - 1656 Title/Abstract Full Text View citing articles Show Details

62%

With hexaaquairon(III) perchlorate

2 h;

Parmar, Anupama; Goyal, Rita; Kumar, Baldev; Kumar, Harish

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998 , vol. 37, # 9 p. 941 - 942 Title/Abstract Full Text Show Details

other semicarbazones; Product distribution;

Ranu, Brindaban C.; Sarkar, Dipak C.

Journal of Organic Chemistry, 1988 , vol. 53, # 4 p. 878 - 879 Title/Abstract Full Text View citing articles Show Details

With potassium carbonate in water

T=9.9°C; E(activ.), ΔG(excit.), ΔH(excit.), ΔS(excit.); other temperatures; KineticsMechanismThermodynamic data;

Rao, M. Anand; Sethuram, B.; Rao, T. Navaneeth

Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981 , vol. 20, # 6 p. 575 - 578 Title/Abstract Full Text Show Details

With sodium perborate in acetic acid

T=40°C; Oxidation; 3 h;

Bandgar, B. P.; Zirange, Sangita M.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997 , vol. 36, # 8 p. 695 - 696 Title/Abstract Full Text Show Details

With silica gel; tin(ll) chloride in tetrahydrofuran

0.5 h; Heating;

Das, Nalin B.; Nanda, Bhagabat; Nayak, Amalendu

Synthetic Communications, 2002 , vol. 32, # 23 p. 3647 - 3651 Title/Abstract Full Text View citing articles Show Details

With dimethylammonium chlorochromate; silica gel in

Zhang, Gui-Sheng; Chai, Bing

diethyl ether; dichloromethane

T=38 - 40°C; 4 h;

Synthetic Communications, 2000 , vol. 30, # 10 p. 1849 - 1855 Title/Abstract Full Text View citing articles Show Details

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481 Synthesize Find similar

Rx-ID: 5321573 Find similar reactions

B: 95%

With hydrogen; [RuCl(η2-H2)(dppe)2]OTf in 1,2-dichloroethane

T=50°C; P=760 Torr; 48 h; Product distribution; Further Variations:Catalysts;

Takei, Izuru; Nishibayashi, Yoshiaki; Ishii, Youichi; Mizobe, Yasushi; Uemura, Sakae; Hidai, Masanobu

Journal of Organometallic Chemistry, 2003 , vol. 679, # 1 p. 32 - 42 Title/Abstract Full Text View citing articles Show Details

With hydrogen; [cis-(Cl)(PPh2CH2CH2PPh2)2Ru][TfO] in benzene-d6

T=50°C; Hydrogenolysis; 3 h; Title compound not separated from byproducts;

Nishibayashi, Yoshiaki; Takei, Izuru; Hidai, Masanobu

Angewandte Chemie - International Edition, 1999 , vol. 38, # 20 p. 3047 - 3050 Title/Abstract Full Text View citing articles Show Details

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482 Synthesize Find similar

A: 28 % Chromat. B: 78 % Chromat.

With polystyrene-supported 5-hydroxy-2-iodoxybenzoic acid in dichloromethane

T=65°C; 2 h;

Sorg; Mengel; Jung; Rademann

Angewandte Chemie - International Edition, 2001 , vol. 40, # 23 p. 4395 - 4397 Title/Abstract Full Text View citing articles Show Details

With diethyl allyl phosphate; potassium carbonate; palladium diacetate in N,N-dimethyl-formamide

Shvo, Youval; Goldman-Lev, Vered

Journal of Organometallic Chemistry, 2002 , vol. 650, # 1-2 p. 151 - 156 Title/Abstract Full Text View citing articles Show Details

5 h;

Rx-ID: 9040461 Find similar reactions

With polystyrene supported 2-iodyl benzamide in dichloromethane

T=25°C; 14 h;

Chung, Woo-Jae; Kim, Duk-Ki; Lee, Yoon-Sik

Tetrahedron Letters, 2003 , vol. 44, # 52 p. 9251 - 9254 Title/Abstract Full Text View citing articles Show Details

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483 Synthesize Find similar Rx-ID: 9310095 Find similar reactions

A: 1% C: 14% D: 13%

With oxygen in acetonitrile

T=13°C; 18 h; UV-irradiation; Product distributionKinetics; Further Variations:Reagents;

Takaki, Ken; Yamamoto, Jun; Matsushita, Yuka; Morii, Hirokazu; Shishido, Tetsuya; Takehira, Katsuomi

Bulletin of the Chemical Society of Japan, 2003 , vol. 76, # 2 p. 393 - 398 Title/Abstract Full Text View citing articles Show Details

484 Synthesize Find similar

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Rx-ID: 9459055 Find similar reactions

Takei, Izuru; Nishibayashi, Yoshiaki; Ishii, Youichi; Mizobe, Yasushi; Uemura, Sakae; Hidai, Masanobu

Journal of Organometallic Chemistry, 2003 , vol. 679, # 1 p. 32 - 42 Title/Abstract Full Text View citing articles Show Details

With hydrogen; [RuCl(η2-H2)(BINAP)2]OTf

T=50°C; P=760 Torr; 18 h; Product distribution; Further Variations:Catalysts;

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485 Synthesize Find similar

A: 97% B: 95%

With Sodium bromate; ammonium cerium(IV) nitrate in acetonitrile

T=80°C; 0.333333 h;

Rx-ID: 9486698 Find similar reactions

Ates, Ali; Gautier, Arnaud; Leroy, Bernard; Plancher, Jean-Marc; Quesnel, Yannick; Vanherck, Jean-Christophe; Marko, Istvan E.

Tetrahedron, 2003 , vol. 59, # 45 p. 8989 - 8999 Title/Abstract Full Text View citing articles Show Details

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486 Synthesize Find similar

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Rx-ID: 9714262 Find similar reactions

With RuO2-FAU in acetone

T=20°C; 5 h; Product distribution; Further Variations:Reagentsconcentration;

Zhan, Bi-Zeng; White, Mary Anne; Pincock, James A.; Robertson, Katherine N.; Cameron, T. Stanley; Sham, Tsun-Kong

Canadian Journal of Chemistry, 2003 , vol. 81, # 6 p. 764 - 769 Title/Abstract Full Text View citing articles Show Details

487 Synthesize Find similar

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Rx-ID: 13949381 Find similar reactions

Multi-step reaction with 2 steps 1: H2 / nickel/silica / methanol / 149.85 °C / atmospheric pressure 2: H2 / nickel/silica / 149.85 °C / atmospheric pressure View Scheme

Pina, Gonzalo; Louis, Catherine; Keane, Mark A.

Physical Chemistry Chemical Physics, 2003 , vol. 5, # 9 p. 1924 - 1931 Title/Abstract Full Text View citing articles Show Details

488 Synthesize Find similar

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With oxygen; alumina catalyst

T=160°C; Product distribution / selectivity; Hide Experimental Procedure

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Rx-ID: 23568375 Find similar reactions

Asahi Kasei Kabushiki Kaisha

Patent: EP1364940 A1, 2003 ; Location in patent: Page/Page column 16 ; Title/Abstract Full Text Show Details

1.2.3:

100 g of commercially available aluminum sec-butoxide was placed in a beaker. Then, into the beaker was stepwise charged an aqueous solution of ammonium metatungstate while vigorously stirring by means of a glass rod, wherein the aqueous solution of ammonium metatungstate was obtained by dissolving 7.0 g of commercially available ammonium metatungstate in 100 g of water. The resultant gel-like product was dried at room temperature for 1 hour, followed by vacuum drying at 120 °C for a whole night. The resultant, dried product was calcined at 400 °C for 4 hours under atmospheric pressure under air circulation, thereby obtaining an alumina catalyst containing tungsten oxide. The obtained alumina catalyst was examined by X-ray fluorescence analysis. The analysis of the alumina catalyst showed that the catalyst had a tungsten content of 21.8 percent by weight. The catalyst was subjected to compression molding, followed by pulverization, thereby obtaining a particulate catalyst. The particles of the catalyst were sieved to obtain catalyst particles having diameters in the range of from 1.0 to 1.4 mm. The obtained solid catalyst was used in the below-mentioned reaction. The solid catalyst was charged into a tubular reactor having an inner diameter of 30 mm, which was made of stainless steel. The tubular reactor containing the solid catalyst was placed in a furnace. The reactor was purged with nitrogen gas, and then heated to 160 °C. Then a reaction gas containing 6.0 percent by volume of cyclohexylamine and 7.0 percent by volume of oxygen was introduced into the reactor at an LHSV of 0.1 liter per hour per liter of the catalyst, thereby effecting a reaction. Samples of the resultant gaseous reaction mixture were automatically withdrawn from the reactor, and analyzed by GC. The analysis of the samples by GC showed that, when the reaction became steady, the conversion of cyclohexylamine was 25.8 percent, and the selectivity for cyclohexanone oxime was 88.5 percent. Further, it was found that, as a by-product, cyclohexanone (selectivity: 5.1 percent) and Ncyclohexylidenecyclohexylamine (selectivity: 4.9 percent) were generated. The analysis by GC was conducted in substantially the same manner as in the case of the amination of cyclohexene in the above-mentioned step 2-1). The reaction mixture was subjected to distillation to obtain a cyclohexanone oxime product having a purity of 99.5 percent or more. A

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489 Synthesize Find similar

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Rx-ID: 24790782 Find similar reactions

With oxygen; anhydrous cobalt diacetate

T=100°C; P=22502.3 Torr; 2 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 19 ; Title/Abstract Full Text Show Details

21:

The procedure of Example 20 was repeated, except that the composition of charged materials to the reactor was changed as follows. [0096] Charged material composition Cyclohexane: 45percent by weight (2.939 mol) Acetic acid: 53.90percent by weight N-Hydroxyphthalimide: 0.1percent by weight Cobalt(II) acetate tetrahydrate: 1percent by weight [0097] The reaction mixture had separated into two liquid-phase layers and was mixed with acetic acid in equal proportions to thereby yield a homogenous one layer, followed by analysis to find that a conversion from cyclohexane was 15.1percent and a selectivity for adipic acid was 50.8percent (0.226 mol). In addition, cyclohexanone (0.113 mol; selectivity: 25.4percent), cyclohexanol (0.0589 mol; selectivity: 13.2percent), cyclohexyl acetate (0.008 mol; selectivity: 1.8percent), glutaric acid (0.023 mol; selectivity: 5.2percent), succinic acid (0.009 mol; selectivity: 2.0percent), phthalimide (0.0013 mol), and phthalic acid (0.0017 mol) were by-produced. A

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490 Synthesize Find similar

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Rx-ID: 24790783 Find similar reactions

20:

With oxygen; anhydrous cobalt diacetate

T=100°C; P=22502.3 Torr; 2 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 19 ; Title/Abstract Full Text Show Details

A total of 550 g of a mixture having the following composition was charged into a 1-L autoclave with a titanium jacket having an agitator including three paddle blades and an agitating motor, an opening for charging an oxygen-containing gas, and another opening for extracting gaseous components. [0092] Charged material composition Cyclohexane: 45percent by weight (2.939 mol) Acetic acid: 53.93percent by weight N-Hydroxysuccinimide: 0.07percent by weight Cobalt(II) acetate tetrahydrate: 1percent by weight [0093] The inside of the reactor (autoclave) was pressurized to 3 MPa with nitrogen gas, and the temperature was raised while rotating the agitator at 500 rpm. At the time when the inside temperature of the reactor reached 100 DEG C, air supply at a flow rate of 100 L (normal conditions) per hour was started. Immediately after the beginning of air supply, a reaction began and the temperature was raised to some extent. While keeping the inner temperature of the reactor at 100 DEG C, the reaction was continued for 120 minutes. The supplied gas was changed to nitrogen gas, and the reaction mixture was cooled. At the time when the temperature of the reaction mixture reached room temperature, the gas in the reactor was released, and the reaction mixture was extracted. [0094] The reaction mixture had separated into two liquid-phase layers and was mixed with acetic acid in equal proportions to thereby yield a homogenous one layer, followed by analysis to find that a conversion from cyclohexane was 15.4percent and a selectivity for adipic acid was 54.2percent (0.245 mol). In addition, cyclohexanone (0.113 mol; selectivity: 25.0percent), cyclohexanol (0.059 mol; selectivity: 13.1percent), cyclohexyl acetate (0.009 mol; selectivity: 2.0percent), glutaric acid (0.023 mol; selectivity: 5.1percent), succinic acid (0.014 mol), and succinimide (0.0015 mol) were by-produced. A

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491 Synthesize Find similar

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Rx-ID: 24790784 Find similar reactions

With oxygen; 2-hydroxy-1,3-isoindolinedione; .LAMBDA.tris(2,4-pentanedionato)cobalt(III); anhydrous cobalt diacetate

T=100°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 14; 18 ; Title/Abstract Full Text Show Details

15:

In a 316 stainless steel reactor having an internal volume of 100 ml, 13.5 g (160 mmol) of cyclohexane, 16.5 g of acetonitrile, 52.3 mg (0.320 mmol) of N-hydroxyphthalimide, 57.1 mg (0.160 mmol) of tris(acetylacetonato)cobalt(III), and 39.9 mg (0.160 mmol) of cobalt(II) acetate were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 100 DEG C. Immediately after the liquid temperature reached 100 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was analyzed to find that a conversion from cyclohexane was 8.8percent and a selectivity for adipic acid was 17.9percent. In addition, glutaric acid (selectivity: 3.4percent), succinic acid (selectivity: 1.7percent), cyclohexanone (selectivity: 41.3percent), cyclohexanol (selectivity: 35.3percent), and cyclohexyl acetate (selectivity: 0.43percent) were by-produced. A

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492 Synthesize Find similar

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Rx-ID: 24790786 Find similar reactions

With oxygen; 2-hydroxy-1,3-isoindolinedione; .LAMBDA.tris(2,4-pentanedionato)cobalt(III) in water

T=110°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 12; 18 ; Title/Abstract Full Text Show Details

In a 316 stainless steel reactor having an internal volume of 300 ml, 52 g (618 mmol) of cyclohexane, 28 g of acetic acid, 203.6 mg (1.236 mmol) of N-hydroxyphthalimide, and 441 mg (1.236 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 120 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 13.8percent and a selectivity for adipic acid was 58.8percent. In addition, glutaric acid (selectivity: 11.0percent), succinic acid (selectivity: 10.9percent), cyclohexanone (selectivity: 3.67percent), cyclohexanol (selectivity: 14.6percent), and cyclohexyl acetate (selectivity: 1.09percent) were by-produced.

With oxygen; 2-hydroxy-1,3isoindolinedione; manganese(II) 2,4pentanedionate; anhydrous cobalt diacetate in water

T=110°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 13; 18 ; Title/Abstract Full Text Show Details

In a 316 stainless steel reactor having an internal volume of 300 ml, 26 g (309 mmol) of cyclohexane, 14 g of acetic acid, 100.8 mg (0.617 mmol) of N-hydroxyphthalimide, 179 mg (0.617 mmol) of bis(acetylacetonato)manganese(II) dihydrate, and 15.4 mg (0.0617 mmol) of cobalt(II) acetate tetrahydrate were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 14.7percent and a selectivity for adipic acid was 62.9percent. In addition, glutaric acid (selectivity: 20.2percent), succinic acid (selectivity: 5.5percent), cyclohexanone (selectivity: 7.1percent), cyclohexanol (selectivity: 3.3percent), and cyclohexyl acetate (selectivity: 1.0percent) were by-produced.

With oxygen; 2-hydroxy-1,3-isoindolinedione; .LAMBDA.-

Daicel Chemical Industries, Ltd.

tris(2,4-pentanedionato)cobalt(III); anhydrous cobalt diacetate in water

T=110°C; P=36778.6 Torr; 0.333333 - 1 h; Product distribution / selectivity; Hide Experimental Procedure

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 10-12; 16-18 ; Title/Abstract Full Text Show Details

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

In a 316 stainless steel reactor having an internal volume of 300 ml, 26 g (309 mmol) of cyclohexane, 14 g of acetic acid, 100.9 mg (0.618 mmol) of N-hydroxyphthalimide, 76.9 mg (0.309 mmol) of cobalt(II) acetate tetrahydrate, and 110 mg (0.309 mmol) of bis(acetylacetonato)cobalt(II) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 20 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 24.4percent and a selectivity for adipic acid was 56.1percent. In addition, glutaric acid (selectivity: 14.3percent), succinic acid (selectivity: 12.1percent), cyclohexanone (selectivity: 10.9percent), cyclohexanol (selectivity: 5.9percent), and cyclohexyl acetate (selectivity: 0.71percent) were by-produced. EXAMPLE 2[0069] In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 53.3 mg (0.214 mmol) of cobalt(II) acetate tetrahydrate, and 76.2 mg (0.214 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 20 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 64.8percent and a selectivity for adipic acid was 71.6percent. In addition, glutaric acid (selectivity: 13.0percent), succinic acid (selectivity: 12.5percent), cyclohexanone (selectivity: 2.1percent), cyclohexanol (selectivity: 1.7percent), and cyclohexyl acetate (selectivity: 0.29percent) were by-produced. EXAMPLE 3[0070] In a 316 stainless steel reactor having an internal volume of 300 ml, 36 g (428 mmol) of cyclohexane, 4 g of acetic acid, 139.7 mg (0.856 mmol) of N-hydroxyphthalimide, 106.6 mg (0.428 mmol) of cobalt(II) acetate tetrahydrate, and 152.5 mg (0.428 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 20 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 8.3percent and a selectivity for adipic acid was 36.4percent. In addition, glutaric acid (selectivity: 10.4percent), succinic acid (selectivity: 7.7percent), cyclohexanone (selectivity: 22.6percent), cyclohexanol (selectivity: 21.6percent), and cyclohexyl acetate (selectivity: 1.4percent) were by-produced. EXAMPLE 4[0071] In a 316 stainless steel reactor having an internal volume of 300 ml, 39.6 g (470 mmol) of cyclohexane, 0.4 g of acetic acid, 153.5 mg (0.940 mmol) of N-hydroxyphthalimide, 117.2 mg (0.470 mmol) of cobalt(II) acetate tetrahydrate, and 167.8 mg (0.470 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 6.9percent and a selectivity for adipic acid was 14.9percent. In addition, glutaric acid (selectivity: 4.5percent), succinic acid (selectivity: 3.9percent), cyclohexanone (selectivity: 40.6percent), cyclohexanol (selectivity: 35.5percent), and cyclohexyl acetate (selectivity: 0.5percent) were by-produced. EXAMPLE 5[0072] In a 316 stainless steel reactor having an internal volume of 300 ml, 12 g (142 mmol) of cyclohexane, 28 g of acetic acid, 46.53mg (0.285 mmol) of N-hydroxyphthalimide, 35.49 mg (0.143 mmol) of cobalt(II) acetate tetrahydrate, and 50.75 mg (0.143 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 13.5percent and a selectivity for adipic acid was 61.0percent. In addition, glutaric acid (selectivity: 12.2percent), succinic acid (selectivity: 11.8percent), cyclohexanone (selectivity: 7.7percent), cyclohexanol (selectivity: 5.8percent), and cyclohexyl acetate (selectivity: 1.5percent) were by-produced. EXAMPLE 6[0074] In a 316 stainless steel reactor having an internal volume of 300 ml, 52 g (618 mmol) of cyclohexane, 28 g of acetic acid, 50.5 mg (0.309 mmol) of N-hydroxyphthalimide, 38.5 mg (0.154 mmol) of cobalt(II) acetate tetrahydrate, and 55.0 mg (0.154 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 20 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 21.7percent and a selectivity for adipic acid was 57.0percent. In addition, glutaric acid (selectivity: 9.37percent), succinic acid (selectivity: 8.37percent), cyclohexanone (selectivity: 15.2percent), cyclohexanol (selectivity: 9.4percent), and cyclohexyl acetate (selectivity: 0.69percent) were by-produced. EXAMPLE 7[0075] In a 316 stainless steel reactor having an internal volume of 300 ml, 52 g (618 mmol) of cyclohexane, 28 g of acetic acid, 25.3 mg (0.154 mmol) of N-hydroxyphthalimide, 19.2 mg (0.077 mmol) of cobalt(II) acetate tetrahydrate, and 27.4 mg (0.077 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 20 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 20.5percent and a selectivity for adipic acid was 55.4percent. In addition, glutaric acid (selectivity: 10.1percent), succinic acid (selectivity: 8.9percent), cyclohexanone (selectivity: 14.2percent), cyclohexanol (selectivity: 8.54percent), and cyclohexyl acetate (selectivity: 2.94percent) were by-produced. EXAMPLE 8[0076] In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 5.33 mg (0.0214 mmol) of cobalt (II) acetate tetrahydrate, and 7.62 mg (0.0214 mmol) of tris(acetylacetonato)cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 17.5percent and a selectivity for adipic acid was 45.8percent. In addition, glutaric acid (selectivity: 10.1percent), succinic acid (selectivity: 7.4percent), cyclohexanone (selectivity: 23.8percent), cyclohexanol (selectivity: 11.1percent), and cyclohexyl acetate (selectivity: 1.9percent) were by-produced. Hide Details

With oxygen; 2-hydroxy-1,3-isoindolinedione; copper diacetate; copper(l) chloride

T=110°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 13; 18 ; Title/Abstract Full Text Show Details

12; 13:

In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 21.2 mg (0.214 mmol) of copper(I) chloride, and 42.7 mg (0.214 mmol) of copper(II) acetate were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 13.0percent and a selectivity for adipic acid was 38.8percent. In addition, glutaric acid (selectivity: 9.4percent), succinic acid (selectivity: 8.4percent), cyclohexanone (selectivity: 29.5percent), cyclohexanol (selectivity: 11.8percent), and cyclohexyl acetate (selectivity: 2.1percent) were by-produced. In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 212 mg (2.14 mmol) of copper(I) chloride, and 427 mg (2.14 mmol) of copper(II) acetate were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 36.6percent and a selectivity for adipic acid was 62.1percent. In addition, glutaric acid (selectivity: 17.7percent), succinic acid (selectivity: 12.7percent), cyclohexanone (selectivity: 1.41percent), cyclohexanol (selectivity: 4.90percent), and cyclohexyl acetate (selectivity: 1.14percent) were by-produced.

With oxygen; 2-hydroxy-1,3isoindolinedione; manganese(II) 2,4pentanedionate; tris(acetylacetonato)manganese(III) in water

T=110°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 12-13; 18 ; Title/Abstract Full Text Show Details

10:

In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 61.9 mg (0.214 mmol) of bis(acetylacetonato)manganese(II) dihydrate, and 75.4 mg (0.214 mmol) of tris(acetylacetonato)manganese(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 38.9percent and a selectivity for adipic acid was 71.5percent. In addition, glutaric acid (selectivity: 14.0percent), succinic acid (selectivity: 9.3percent), cyclohexanone (selectivity: 0.4percent), cyclohexanol (selectivity: 3.9percent), and cyclohexyl acetate (selectivity: 1.0percent) were by-produced.

With oxygen; Fe(acac)3; iron(II) lactate; 2-hydroxy-1,3isoindolinedione

T=110°C; P=36778.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Daicel Chemical Industries, Ltd.

Patent: EP1350786 A1, 2003 ; Location in patent: Page/Page column 13; 18 ; Title/Abstract Full Text Show Details

In a 316 stainless steel reactor having an internal volume of 300 ml, 18 g (214 mmol) of cyclohexane, 22 g of acetic acid, 69.7 mg (0.428 mmol) of N-hydroxyphthalimide, 61.6 mg (0.214 mmol) of iron(II) lactate [ferrous lactate], and 75.5 mg (0.214 mmol) of tris(acetylacetonato)iron(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm<2> (4.9 MPa) with a gaseous mixture comprising 50percent of O2 and 50percent of N2. The liquid temperature was raised on an oil bath and was held at 110 DEG C. Immediately after the liquid temperature reached 110 DEG C, absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 14.3percent and a selectivity for adipic acid was 31.8percent. In addition, glutaric acid (selectivity: 8.1percent), succinic acid (selectivity: 9.9percent), cyclohexanone (selectivity: 38.9percent),

cyclohexanol (selectivity: 10.0percent), and cyclohexyl acetate (selectivity: 1.4percent) were by-produced.

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86%

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80%

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78%

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59%

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96 % Chromat.

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494 Synthesize Find similar 89%

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