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Cas Database

108-94-1

108-94-1

Identification

  • Product Name:Cyclohexanone

  • CAS Number: 108-94-1

  • EINECS:203-631-1

  • Molecular Weight:98.1448

  • Molecular Formula: C6H10O

  • HS Code:2914.22

  • Mol File:108-94-1.mol

Synonyms:AI3-00041;Anon;Anone;CCRIS 5897;Cicloesanone;Cicloesanone [Italian];Cyclohexanon;Cyclohexyl ketone;Cykloheksanon;Cykloheksanon [Polish];Hexanon;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis. (USCG, 1999) Absorption, Distribution and Excretion... ABSORPTION OF CYCLOHEXANONE THROUGH SKIN PRODUCES SAME EFFECTS AS BY OTHER ROUTES BUT DOSAGE REQUIRED IS LARGER.

  • Fire-fighting measures: Suitable extinguishing media ALCOHOL FOAM, DRY CHEMICAL OR CARBON DIOXIDE Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Remove all ignition sources. Ventilate area of spill or leak. For small quantities of liquids containing cyclohexanone, absorb on paper towels and place in an appropriate container. Place towels in a safe place (such as a fume hood) for evaporation. Allow sufficient time for evaporation of the vapors so that the hood ductwork is free from cyclohexanone vapors. Burn the paper in a suitable location away from combustible materials.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants.Keep containers closed; prohibit open flame. Store in cool and dark plane.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 25 ppm (100 mg/cu m). Skin.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 2080 Articles be found

Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark

Anderson,Andia, Alexander A.,Woerpel

, (2021)

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

PHOTOOXIDATION OF ALKANES AND BENZENE BY POLYVANADATE IN CF3CO2H

Kats, M. M.,Shul'pin, G. B.

, p. 2233 (1990)

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One-step hydroxylation of benzene to phenol via a Pd capillary membrane microreactor

Wang, Xiaobin,Tan, Xiaoyao,Meng, Bo,Zhang, Xiongfu,Liang, Qi,Pan, Hui,Liu, Shaomin

, p. 2380 - 2391 (2013)

A novel Pd capillary membrane microreactor for one-step hydroxylation of benzene to phenol was synthesized and investigated to showcase the effectiveness of 'Niwa concept'. Reaction parameters including H2/O2 ratio and temperature were systematically studied for their effects on benzene conversion and phenol yield. A detailed examination of different membrane reactors, feed mode and long-term reaction stability was also conducted. Pd capillary membrane displayed good stability for low temperature separation and reaction due to the excellent anchorage of Pd layer into the porous α-alumina support. An optimum H2/O2 ratio was identified at 473 K with the benzene conversion of 19.6% and phenol yield of 18.1%. An increase in reaction temperature caused not only an increase in benzene conversion but also a decrease in phenol selectivity. A comparison between our work and the literature results was also made to discuss the feasibility of the membrane reactor concept. Experimental results proved that narrow flow channels and larger Pd membrane surface area-to-volume ratios provided more effective area of Pd interface and promoted the radial diffusion of reactants, enabling the reactive species more opportunities to react directly with benzene resulting in high benzene conversion. The Royal Society of Chemistry 2013.

Improved Rhodium Hydrogenation Catalysts Immobilized on Oxidic Supports

Merckle,Bluemel

, p. 584 - 588 (2003)

Wilkinson-type rhodium hydrogenation catalysts immobilized on oxidic supports via mono-and bidentate phosphine linkers have been studied by 31P solid-state NMR, and their recycling stability and lifetime with respect to hydrogenation of 1-dodecene, 2-cyclohexen-1-one, and 4-bromostyrene have been improved substantially.

Synthesis of 1,1′-bishydroperoxydi(cycloalkyl) peroxides by homocoupling of 11-15-membered gem-bis(hydroperoxy)cycloalkanes in the presence of boron trifluoride

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

, p. 1214 - 1218 (2005)

A procedure was developed for the synthesis of 1,1′- bishydroperoxydi(C11-C15-cycloalkyl) peroxides based on homocoupling of geminal 11-15-membered bis(hydroperoxy)cycloalkanes in the presence of BF3·OEt2.

Polypyrrole films containing rhodium(I) and iridium(I) complexes: Improvement in their synthesis and electrocatalytic activity in aqueous media

Hamar-Thibault, Sylvaine,Moutet, Jean-Claude,Tingry, Sophie

, p. 31 - 37 (1997)

Functionalized polypyrrole films containing M1(L)(diene)]+ complexes (M = rhodium or iridium, L = substituted 2,2′-bipyridine or 1,10-phenanthroline) have been synthesized by complexation of [M1(diene)CL]2 precu

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Brooks,D.W.,Gettler,J.D.

, p. 4469 - 4475 (1962)

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Role of keto intermediates in the hydrodeoxygenation of phenol over Pd on oxophilic supports

De Souza, Priscilla M.,Rabelo-Neto, Raimundo C.,Borges, Luiz E. P.,Jacobs, Gary,Davis, Burtron H.,Sooknoi, Tawan,Resasco, Daniel E.,Noronha, Fabio B.

, p. 1318 - 1329 (2015)

The performance of Pd catalysts supported on SiO2, Al2O3 and ZrO2 for the hydrodeoxygenation (HDO) of phenol has been compared in the gas phase, at 300 °C and 1 atm using a fixed bed reactor. While Pd supported on SiO2 and Al2O3 exhibits high selectivity to cyclohexanone, when supported on an oxophilic support such as ZrO2, it favors the selectivity toward benzene, reducing the formation of ring-hydrogenated products, cyclohexanone and cyclohexanol. Diffuse reflectance infrared Fourier transform spectroscopy experiments support the participation of a keto-tautomer intermediate (2,4-cyclohexadienone) in the reaction. This intermediate can be hydrogenated in two different pathways. If the ring is hydrogenated, cyclohexanone and cyclohexanol are dominant products, as in the case of Pd/SiO2 and Pd/Al2O3 catalysts. By contrast, if the carbonyl group of the keto-intermediate tautomer is hydrogenated, benzene is directly formed via rapid dehydration of the unstable cyclohexadienol intermediate. This is observed in the case of Pd/ZrO2 catalyst. These results demonstrate that the selectivity for HDO of phenol can be controlled by using supports of varying oxophilicity. (Chemical Equation Presented).

-

Shono et al.

, p. 165 (1979)

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Cobalt immobilized on hydroxyapatite as a low-cost and highly effective heterogeneous catalyst for alkenes epoxidation under mild conditions

Mekrattanachai, Pagasukon,Cao, Changyan,Li, Zhaohua,Li, Huining,Song, Weiguo

, p. 37303 - 37306 (2018)

Transition metal Co immobilized on hydroxyapatite with a loading of 0.05 wt% (denoted 0.05 wt% Co/HAP) could catalyze partial oxidation of cyclic alkenes, aromatic alkenes and aliphatic alkenes to yield epoxide products with excellent selectivity at 30 °C with O2 and iso-butyraldehyde as co-oxidant. The TOF value was as high as 6261 h?1 for epoxidation of cyclohexene. In addition, the prepared 0.05 wt% Co/HAP catalyst can be re-used at least 6 times without significant loss of catalytic activity and selectivity.

Catalytic Activity of a Polymerizable tris(β-ketoesterate)Iron(III) Complex towards the Oxidation of Organic Substrates

Mastrorilli, Piero,Nobile, Cosimo Francesco

, p. 4193 - 4196 (1994)

The facile oxidation of alkenes, aldehydes, cyclic ketones, alkanes, sulfides and alcohols is achieved by a polymerizable b-ketoesterato complex under Mukaiyama's conditions (atmospheric pressure of molecular oxygen in the presence of a sacrificial aldehyde at room temperature).

"Solvent-free" synthesis of thermally stable and hierarchically porous aluminophosphates (SF-APOs) and heteroatom-substituted aluminophosphates (SF-MAPOs)

Zhang, Pengling,Wang, Liang,Ren, Limin,Zhu, Longfeng,Sun, Qi,Zhang, Jian,Meng, Xiangju,Xiao, Feng-Shou

, p. 12026 - 12033 (2011)

Hierarchically porous aluminophosphates (SF-APOs) and metal substituted aluminophosphates (SF-MAPOs, M = Co, Fe, Cr) have been synthesized via simple grinding and heating in the absence of solvent. Characterization results show that these mesoporous aluminophosphates have a hierarchically microporous/mesoporous structure. In addition, metal atoms can be efficiently incorporated into the walls of mesoporous aluminophosphates, and the SF-CoAPO sample shows high catalytic activity in cyclohexene oxidation compared with microporous samples. Special features of the "solvent-free" synthesis route, such as increasing product yield, saving energy, elimination of pollution, and convenience for incorporation of heterogeneous atoms, ensure its great potential in the synthesis of porous materials. The Royal Society of Chemistry 2011.

Cubberley,Mueller

, p. 1535 (1947)

ORGANOBORANES FOR SYNTHESIS. 4. OXIDATION OF ORGANOBORANES WITH PYRIDINIUM CHLOROCHROMATE. A DIRECT SYNTHESIS OF ALDEHYDES FROM TERMINAL ALKENES VIA HYDROBORATION

Brown, Herbert C.,Kulkarni, Surendra U.,Rao, C. Gundu,Patil, Vemanna D.

, p. 5515 - 5522 (1986)

The oxidation of trialkylboranes containing primary alkyl groups with pyridinium chlorochromate (PCC) in methylene chloride provides the corresponding aldehydes in good yields.The stoichiometry for the oxidation of alcohols, borate esters and trialkylboranes with PCC has been examined.In view of the poor regioselectivity (only 94percent primary alkyl groups) and functional group tolerance observed in the hydroboration with borane (BH3*THF or BH3*SMe2), a more selective hydroborating agent, bis(3-methyl-2-butyl)borane (disiamylborane), was utilized for the preparation of aldehydes from terminal alkenes.However, the formation of 3-methyl-2-butanone as a by-product, and the requirement of six moles of PCC per mole of aldehyde are major disadvantages in this method.This difficulty was circumvented by employing monochloroborane-dimethyl sulfide for hydroboration.This reagent exhibits high regioselectivity (> 99percent primary alkyl groups) in the hydroboration of terminal alkenes.Oxidation of the resulting dialkylchloroborane following hydrolysis affords the desired aldehydes in satisfactory yields.Consequently, the hydroboration of terminal alkenes, followed by PCC oxidation, represents a direct convenient method for the transformation of alkenes into the corresponding aldehydes.

Reduction of Aromatic Nitro Compounds by Secondary Alcohols Using Rhodium Complexes as Catalysts

Liou, K. F.,Cheng, C. H.

, p. 3018 - 3021 (1982)

-

Nitrogen-functionalized ordered mesoporous carbons as multifunctional supports of ultrasmall Pd nanoparticles for hydrogenation of phenol

Li, Zelong,Liu, Jianhua,Xia, Chungu,Li, Fuwei

, p. 2440 - 2448 (2013)

N-functionalized ordered mesoporous carbons could be readily obtained by post-synthesis treatment with nitrogen containing molecules to achieve materials with a nitrogen loading as high as 8.6 wt % and well preserved mesopore structure. Using NH3/su

Effect of Zirconia Morphology on Hydrodeoxygenation of Phenol over Pd/ZrO2

De Souza, Priscilla M.,Rabelo-Neto, Raimundo C.,Borges, Luiz E. P.,Jacobs, Gary,Davis, Burtron H.,Graham, Uschi M.,Resasco, Daniel E.,Noronha, Fabio B.

, p. 7385 - 7398 (2015)

This work studies the effect of zirconia structure on the performance of Pd/ZrO2 catalysts for hydrodeoxygenation of phenol at 300 °C and 1 atm using a fixed bed reactor. Benzene was the major product over Pd/t-ZrO2, while significant formation of cyclohexanone was observed over Pd/m-ZrO2. On the other hand, Pd/m,t-ZrO2 exhibited intermediary behavior. DRIFTS of adsorbed pyridine, NH3-TPD, and the dehydration of the cyclohexanol reaction revealed that the Pd/t-ZrO2 catalyst exhibits a higher density of oxophilic sites than Pd/m-ZrO2 and Pd/m,t-ZrO2. This promoted the formation of deoxygenated products. However, a mechanism involving dehydration of cyclohexanol to cyclohexene, followed by dehydrogenation to benzene, may not be ruled out. Pd/ZrO2 catalysts significantly deactivated as a function of time on stream. Results of dehydrogenation of cyclohexane and dehydration of cyclohexanol indicate that the Pd particle size increased and the density of oxophilic sites decreased during the hydrodeoxygenation of the phenol reaction. In addition, the DRIFTS spectra under reaction conditions demonstrated that the coverage of oxophilic sites by phenoxy and intermediate species increased during the reaction. The growth of Pd particles is likely responsible for the losses in the metal-support interface that gradually inhibits the ability of the adsorbed species to turnover at the metal-support boundary.

Liquid phase cyclohexene oxidation over vanadia based catalysts with tert-butyl hydroperoxide: Epoxidation versus allylic oxidation

El-Korso, Sanaa,Khaldi, Ilyes,Bedrane, Sumeya,Choukchou-Braham, Abderrahim,Thibault-Starzyk, Frédéric,Bachir, Redouane

, p. 89 - 96 (2014)

VO2-SiO2 based catalysts with V contents between 5 and 20 wt.% were prepared from inorganic precursors via the sol-gel process and subsequently dried, calcined and reduced at 673 K. Structural characterization of these materials was carried out with X-rays diffraction (XRD), ICP, N 2 adsorption-desorption at 77 K, UV-vis diffused reflectance spectroscopy (DR UV-vis), FTIR and pyridine adsorption followed by FTIR. Their catalytic activities in the cyclohexene epoxidation with TBHP as oxidant and heptane as solvent were also examined. Results of XRD and DR UV-visible spectroscopy revealed that VO2 species are well dispersed on silica. BET analysis showed that the surface area decreases from 390 to 22 m2 g-1 with V content. The results of pyridine adsorption followed by FTIR indicated that the 5 wt.% VO2-SiO2 catalyst displays low acid densities. Experimental results pointed out that the 5 wt.% VO 2-SiO2 catalysts offer excellent activity. The obtained cyclohexene conversion and selectivity toward epoxide are 21% and 84% respectively. A reaction mechanism explaining clearly epoxidation versus allylic oxidation is proposed.

Epoxidation of cyclohexene with tert-butyl hydroperoxide catalyzed by mixed oxide V2O5–TiO2

Lahcene, Driss,Choukchou-Braham, Abderrahim

, p. 1529 - 1535 (2018)

TiO2 and 20 wt% V2O5–TiO2 catalysts were prepared by the sol–gel route and calcined at 500 °C. The mixed oxide presented the crystalline structures of TiO2 anatase and V2O5 Shcherbinaite phases, with a BET (Brunauer–Emmett–Teller) surface area of 19 m2/g. The catalytic material was tested for the epoxidation of cyclohexene by tert-butyl hydroperoxide at 80 °C. The activity and selectivity were investigated as a function of the reaction time as well as the amounts of the catalyst and solvent. The reaction followed second-order kinetics, and the best catalytic performance was observed after 6 hr of reaction time, with 150 mg of catalyst in n-heptane solvent. The epoxidation selectivity reached 76% at 48% conversion. The catalyst remained stable after two cycles.

Anodic Oxidation of Heterocumulenes in Acetonitrile

Becker, James Y.,Zinger, Baruch

, p. 2327 - 2329 (1982)

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o-Nitrobenzyl Alcohol, a Simple and Efficient Reagent for the Photoreversible Protection of Aldehydes and Ketones

Gravel, Denis,Murray, Stevens,Ladouceur, Gaetan

, p. 1828 - 1829 (1985)

Two independent procedures are described for the preparation of bis-o-nitrobenzyl acetal derivatives of aldehydes and ketones which are shown to be photoremovable in high yield by simple irradiation at 350 nm in an aprotic solvent.

Synergistic catalysis of nano-Pd and nano rare-earth oxide/AC: Complex nanostructured catalysts fabricated by a photochemical route for selective hydrogenation of phenol

Zhang, Yanji,Zhou, Jicheng,Si, Jiaqi

, p. 54779 - 54788 (2017)

Cyclohexanone is an important industrial intermediate in the manufacture of polyamides in the chemical industry, but direct selective hydrogenation of phenol to cyclohexanone under mild conditions to achieve both high conversion and selectivity is a chall

Mild oxidative conversion of nitroalkanes into carbonyl compounds in ionic liquids

Bortolini, Olga,Nino, Antonio De,Garofalo, Angelo,Maiuolo, Loredana,Russo, Beatrice

, p. 2483 - 2487 (2010)

Basic hydrogen peroxide and sodium perborate were found to be cheap and efficient alternatives for the conversion of primary and secondary nitro to carbonyl compounds (Nef reaction) in ionic liquids. Copyright Taylor & Francis Group, LLC.

A novel, green 1-glycyl-3-methyl imidazolium chloride-copper(II) complex catalyzed CH oxidation of alkyl benzene and cyclohexane

Karthikeyan, Parasuraman,Bhagat, Pundlik Rambhau,Kumar, S. Senthil

, p. 681 - 684 (2012)

A variety of alkyl-arenes and cyclohexane were converted to the corresponding ketones with NaClO as the oxidant in the presence of 1-glycyl-3-methyl imidazolium chloride-copper(II) complex. This method contains simplified product isolation and catalyst recycling, affording benzylic CH oxidation of alkyl-arenes imparting high yield of ketones. Furthermore, complex could be reused seven times without a significant loss of its catalytic activity.

Rhodium(iii) complexes with a bidentate N-heterocyclic carbene ligand bearing flexible dendritic frameworks

Fujihara, Tetsuaki,Obora, Yasushi,Tokunaga, Makoto,Tsuji, Yasushi

, p. 1567 - 1569 (2007)

Rh(iii) complexes with a bidentate N-heterocyclic carbene ligand bearing flexible dendritic frameworks have been synthesized and fully characterized by X-ray crystallographic analysis, NMR measurements and theoretical calculations. The Royal Society of Chemistry.

Calcium tungstate: A convenient recoverable catalyst for hydrogen peroxide oxidation

Tressler, Caitlin M.,Stonehouse, Peter,Kyler, Keith S.

, p. 4875 - 4878 (2016)

Calcium tungstate was found to be an excellent catalyst for large scale "green" oxidations of organic substrates (amines, alkenes, alcohols, sulfides) with hydrogen peroxide. It displays the unusual dual characteristics of producing a soluble pertungstate species, allowing for homogeneous reaction conditions, but then precipitating, unchanged, at the end of the oxidation. These qualities allow for easy catalyst recovery and minimal waste stream generation for large scale application.

On the efficiency of phenol and cyclohexanone electrocatalytic hydrogenation - Effect of conditioning and working pH in acetic acid solution on palladium/fluorine-doped tin dioxide supported catalyst

Tountian, Dihourahouni,Brisach-Wittmeyer, Anne,Nkeng, Paul,Poillerat, Gerard,Menard, Hugues

, p. 463 - 471 (2010)

The electrocatalytic hydrogenation (ECH) of phenol and cyclohexanone was performed on a conductive Pd/SnO2:F catalyst. The catalyst was obtained by the impregnation method. We studied the influence of the pH of the supporting electrolyte, the conditioning pH, and the quantity of the conditioning charge passed before hydrogenation. Fourier transform infrared spectroscopy analysis showed that the functionalization of the catalyst surface by the acetic acid electrolyte depends on the pH. A direct correlation was observed between the efficiency of the hydrogenation, the pH of the electrolyte, and the electrode conditioning charge. Phenol hydrogenation was favored in acidic media, whereas cyclohexanone hydrogenation needed an acidic medium for conditioning and a basic medium for hydrogenation. The ECH rate appeared to depend on the functionalization of the catalyst surface, the adsorption of the target organic molecule on the catalyst, and its structural modification with the pH.

Molecular Recognition on Synthetic Amorphous Surfaces. The Influence of Functional Group Positioning on the Effectiveness of Molecular Recognition

Shea, K. J.,Dougherty, T. K.

, p. 1091 - 1093 (1986)

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Dehydrogenation of cyclohexanol on copper containing catalysts: The role of the support and the preparation method

Popova,Dimitrov,Santo, V. Dal,Ravasio,Scotti

, p. 150 - 153 (2012)

SiO2 and Al2O3 supported copper catalysts were prepared by "chemisorption-hydrolysis" or incipient wetness impregnation methods and investigated by XRD, TG-TPR, UV-vis diffuse reflectance and FTIR spectroscopy. Formation of finely dispersed copper oxide species was registered for the samples prepared by "chemisorption-hydrolysis" method, while a significant amount of XRD detectable copper oxide phase is registered for the SiO2 impregnated one. The latter materials possess higher catalytic selectivity in cyclohexanol dehydrogenation to cyclohexanone.

Cationic Palladium Nitro Complexes as Catalysts for the Oxygen-based Oxidation of Alkenes to Ketones, and for the Oxydehydrogenation of Ketones and Aldehydes to the α,β-Unsaturated Analogues

Wenzel, Timothy T.

, p. 932 - 933 (1989)

Cationic palladium nitro complexes permit more rapid and more selective oxidation of alkenes to ketones than existing metal nitro catalysts; they also oxidatively dehydrogenate ketones and aldehydes to the corresponding α,β-unsaturated analogues under extremely mild conditions.

Comparison of three enoate reductases and their potential use for biotransformations

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

, p. 1521 - 1531 (2007)

Enoate reductases (ERs) selectively reduce carbon-carbon double bonds in α,β-unsaturated carbonyl compounds and thus can be employed to prepare enantiomerically pure aldehydes, ketones, and esters. Most known ERs, most notably Old Yellow Enzyme (OYE), are biochemically very well characterized. Some ERs have only been used in whole-cell systems, with endogenous ketoreductases often interfering with the ER activity. Not many ERs are biocatalytically characterized as to specificity and stability. Here, we cloned the genes and expressed three non-related ERs, two of them novel, in E. coli: XenA from Pseudomonas putida, KYE1 from Kluyveromyces lactis, and Yers-ER from Yersinia bercovieri. All three proteins showed broad ER specificity and broad temperature and pH optima but different specificity patterns. All three proteins prefer NADPH as cofactor over NADH and are stable up to 40°C. By coupling Yers-ER with glucose dehydrogenase (GDH) to recycle NADP(H), conversion of > 99 % within one hour was obtained for the reduction of 2-cyclohexenone. Upon lowering the loadings of Yers-ER and GDH, we discovered rapid deactivation of either enzyme, especially of the thermostable GDH. We found that the presence of enone substrate, rather than oxygen or elevated temperature, is responsible for deactivation. In summary, we successfully demonstrate the wide specificity of enoate reductases for a range of α,β- unsaturated carbonyl compounds as well as coupling to glucose dehydrogenase for recycling of NAD(P)(H); however, the stability limitations we found need to be overcome to envision large-scale use of ERs in synthesis.

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Ogura,K. et al.

, p. 2767 - 2770 (1975)

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Me'rour et al.

, p. 337,348 (1979)

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OXIDATION OF OLEFINS TO KETONES IN COMBINATION WITH ELECTROOXIDATION

Tsuji, Jiro,Minato, Makoto

, p. 3683 - 3686 (1987)

In combination with anodic oxidation, 1-alkenes are oxidized to methyl ketones efficiently by the catalyses of Pd(OAc)2 and benzoquinone.Cyclopentene and Cyclohexene are oxidized smoothly to the corresponding ketones in high yields.

Copper nanoparticle/carbon quantum dots hybrid as green photocatalyst for high-efficiency oxidation of cyclohexane

Qiao, Shi,Fan, Baohu,Yang, Yanmei,Liu, Naiyun,Huang, Hui,Liu, Yang

, p. 43058 - 43064 (2015)

To develop green catalysts for cyclohexane oxidation with high efficiency and high selectivity is a trend in nanotechnology and nanocatalysis. In this work, we demonstrate that copper nanoparticles/carbon quantum dots (Cu/CQDs) hybrid as photocatalyst exh

One-pot synthesis of phenol and cyclohexanone from cyclohexylbenzene catalyzed by N-hydroxyphthalimide (NHPI)

Aoki, Yasuhiro,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 5219 - 5222 (2005)

Synthesis of phenol and cyclohexanone in one pot was examined by means of the NHPI-catalyzed aerobic oxidation of cyclohexylbenzene. The aerobic oxidation of cyclohexylbenzene catalyzed by NHPI followed by treatment with sulfuric acid afforded phenol and

Highly Effective Dehydrogenation of Cyclohexanol to Cyclohexanone over Carbon-Supported Cobalt Catalyst

Uemichi, Yoshio,Shouji, Kiyoshi,Sugioka, Masatoshi,Kanazuka, Takaji

, p. 385 - 387 (1995)

The dehydrogenation of cyclohexanol to cyclohexanone has been studied over activated carbon-supported transition metals as catalysts.The Co/carbon catalyst was found to be highly effective for the reaction.Its catalytic behaviors strongly depended on the temperature of hydrogen reduction.Highly dispersed and well-reduced cobalt catalyst showed pronounced activity and stability.

Effective hydrodechlorination of 4-chlorophenol over pd deposited on multiwall carbon nanotubes

Deng, Hongying,Fan, Guangyin,Wang, Yinhu

, p. 1306 - 1311 (2014)

Multiwall carbon nanotubes (MWCNTs) supported Pd nanoparticles were prepared by impregnation method and characterized by TEM, XRD, XPS, and FT-IR. The as-prepared catalyst Pd/MWCNTs exhibited excellent catalytic property for the hydrodechlorination (HDC) of 4-chlorophenol (4-CP) in aqueous medium without any additives under mild conditions. The results indicated that the choice of support and the introduction of metal ions played a significant role in the catalytic property for HDC of 4-CP. The high catalytic performance of Pd/MWCNTs was attributed to the highly dispersed Pd nanoparticles on the support MWCNTs and the interaction between support and metal actives. Copyright Taylor & Francis Group, LLC.

MECHANISM OF THE SELECTIVE FORMATION OF CYCLOHEXANONE IN THE DECOMPOSITION OF CYCLOHEXYL HYDROPEROXIDE BY CHROMIUM STEARATE

Petrov, L. V.,Solyanikov, V. M.

, p. 1958 - 1960 (1991)

From a comparison of the rates of formation of cyclohexanone and 2-decanone in cyclohexane solutions of cyclohexyl hydroperoxide or tert-butyl-hydroperoxide in the presence of chromium(III) stearate and a mixture of cyclohexanol and 2-decanol in an atmosphere of argon at 350 K, it is concluded that the direct breakdown of cyclohexyl hydroperoxide by chromium stearate leads to selective formation of cyclohexanone.The contribution of the oxidation of cyclohexanol to ketone formation at a cyclohexanol concentration comparable with the hydroperoxide concentration (ca. 0.1 M) is ca. 10percent.

Intercalation of a Rhodium Carbonyl into the Layered Vanadyl Phosphate VOPO4.2H2O and its Catalytic Activity

Datta, Arunabha,Bhaduri, Sumit,Kelkar, Ravindra Y.,Khwaja, Hanif I.

, p. 11811 - 11813 (1994)

Evidence for the intercalation of a rhodium carbonyl into the layered vanadyl phosphate, VOPO4.2H2O has been provided from XRD, FTIR and XPS studies.The incorporated rhodium carbonyl has been found to exhibit catalytic activity and shape selectivity in the hydrogenation of olefinic substrates.

Study of the deactivation of copper-based catalysts for dehydrogenation of cyclohexanol to cyclohexanone

Simón, Ernesto,Rosas, Juana María,Santos, Aurora,Romero, Arturo

, p. 150 - 158 (2012)

Catalytic dehydrogenation of cyclohexanol was carried out in the gas phase in a continuous fixed bed reactor under atmospheric pressure. Two commercial catalysts composed by copper chromite and copper zinc oxide were tested. The activity of the catalysts

PALLADIUM CATALYSED OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS UNDER SOLID-LIQUID PHASE TRANSFER CONDITIONS

Choudary, B. M.,Reddy, N. Prabhakar,Kantam, M. Lakshmi,Jamil, Zafar

, p. 6257 - 6258 (1985)

Palladium acetate catalysed the oxidation of primary and secondary alcohols to aldehydes and ketones respectively at room temperature and atmospheric pressure under solid-liquid phase transfer conditions.

CYCLOKETONIZATION AND LINEAR POLYKETONIZATION OF α,ω-DICARBOXYLIC ACIDS. COMMUNICATION 7. PREPARATION AND REACTIONS OF ZINC SALTS OF UNBRANCHED DICARBOXYLIC ACIDS

Vasina, T. V.,Chelmakova, S. A.,Lutovinova, V. N.,Liberman, A. L.

, (1982)

-

-

Tiffeneau,Tchoubar

, p. 1624 (1934)

-

Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system

Tong, Xinli,Xu, Jie,Miao, Hong

, p. 1953 - 1957 (2005)

A highly efficient o-phenanthroline-mediated, metal-free catalytic system has been developed for oxidation of hydrocarbons with dioxygen in the presence of N-hydroxyphthalimide; various hydrocarbons were efficiently and high selectively oxidized, e.g., ethylbenzene to acetophenone in 97% selectivity and 76% conversion, under mild conditions.

Preparation and Characterisation of a Palladium-Copper Heterometallic Complex and its Catalytic Activity towards Oxidation of Alkenes

Hosokawa, Takahiro,Takano, Minoru,Murahashi, Shun-Ichi,Ozaki, Hiroshi,Kitagawa, Yasuyuki,et al.

, p. 1433 - 1434 (1994)

Treatment of PdCl2(MeCN)2 and CuCl2 with pyrrolidin-2-one L gives a novel Pd-Cu heterometallic complex having a polymeric structure of n which catalyses the oxidation of cyclohexene in ClCH2CH2Cl-MeOH.

Catalytic synergism in a C;inf;60;/inf;IL;inf;10;/inf;TEMPO;inf;2;/inf; hybrid in the efficient oxidation of alcohols

Beejapur, Hazi Ahmad,Campisciano, Vincenzo,Giacalone, Francesco,Gruttadauria, Michelangelo

, p. 51 - 58 (2015)

A novel fullerene [5:1]hexakisadduct bearing two 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) radicals and ten 1-propyl-3-methylimidazolium bromide moieties has been synthesized and characterized. Such an C;inf;60;/inf;IL;inf;10;/inf;TEMPO;inf;2;/inf; hybrid has been successfully employed as a catalyst in the selective oxidation of a wide series of alcohols and is highly active at just 0.1 mol% loading. Moreover, it can be easily recovered by adsorption onto a multilayered covalently-linked SILP phase (mlc-SILP) through a "release and catch" approach and reused for up to 12 cycles without loss in efficiency. Interestingly, a catalytic synergistic effect of TEMPO and imidazolium bromide moieties combined in the same hybrid has been clearly shown.

Modeling TauD- J: A high-spin nonheme oxoiron(IV) complex with high reactivity toward C-H bonds

Biswas, Achintesh N.,Puri, Mayank,Meier, Katlyn K.,Oloo, Williamson N.,Rohde, Gregory T.,Bominaar, Emile L.,Münck, Eckard,Que, Lawrence

, p. 2428 - 2431 (2015)

High-spin oxoiron(IV) species are often implicated in the mechanisms of nonheme iron oxygenases, their C-H bond cleaving properties being attributed to the quintet spin state. However, the few available synthetic S = 2 FeIV=O complexes supported by polydentate ligands do not cleave strong C-H bonds. Herein we report the characterization of a highly reactive S = 2 complex, [FeIV(O)(TQA)(NCMe)]2+ (2) (TQA = tris(2-quinolylmethyl)amine), which oxidizes both C-H and C=C bonds at -40 °C. The oxidation of cyclohexane by 2 occurs at a rate comparable to that of the oxidation of taurine by the TauD-J enzyme intermediate after adjustment for the different temperatures of measurement. Moreover, compared with other S = 2 complexes characterized to date, the spectroscopic properties of 2 most closely resemble those of TauD-J. Together these features make 2 the best electronic and functional model for TauD-J to date.

TRANSFORMATION OF ORGANOIRON COMPLEXES OF SYNTHETIC AND CHEMICAL INTEREST.

Rosenblum,Bucheister,Chang,Cohen,Marsi,Samuels,Scheck,Sofen,Watkins

, p. 129 - 136 (1983)

Cationic organometallic complexes derived by complexation of vinyl ethers with the dicarbonyl cyclopentadienyliron cation (F//p** plus ) are readily prepared, highly reactive reagents. These substances have been shown to function as vinyl cation equivalents for the vinylation of ketones, and for the synthesis of alpha -methylene- gamma -lactones and dihydrofurans. Similar complexation of propiolic esters gives a reactive species, which functions as a beta -acrylic ester cation equivalent and yields cyclobutenes, 1,3-dienes and dihydro- alpha -pyrones with olefins and cinnamic esters with aromatic systems.

-

Greene et al.

, p. 2707 (1976)

-

Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles

Ardakani, Mehdi Hatefi,Sabet, Mohammad,Samani, Mahnaz

, (2022/01/22)

The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4

An efficient method for the catalytic aerobic oxidation of cycloalkanes using 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI)

Guha, Samar K.,Ishii, Yasutaka

, p. 327 - 335 (2021/12/13)

N-Hydroxyphthalimide (NHPI) is known to be an effective catalyst for the oxidation of hydrocarbons. The catalytic activity of NHPI derivatives is generally increased by introducing an electron-withdrawing group on the benzene ring. In a previous report, two NHPI derivatives containing fluorinated alkyl chain were prepared and their catalytic activity was investigated in the oxidation of cycloalkanes. It was found that the fluorinated NHPI derivatives showed better yields for the oxidation reaction. As a continuation of our work with fluorinated NHPI derivatives, our next aim was to investigate the catalytic activity of the NHPI derivatives by introducing fluorine atoms in the benzene ring of NHPI. In the present research, 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI) is prepared and its catalytic activity has been investigated in the oxidation of two different cycloalkanes for the first time. It has been found that F4-NHPI showed higher catalytic efficiency compared with that of the parent NHPI catalyst in the present reactions. The presence of a fluorinated solvent and an additive was also found to accelerate the oxidation.

An alternative route for the preparation of phenol: Decomposition of cyclohexylbenzene-1-hydroperoxide

Yang, Yufei,Zhang, Yadong

, p. 71 - 80 (2021/09/28)

In this work, a HPW/ZSM-5 catalyst was prepared by impregnating phosphotungstic acid (HPW) with carrier ZSM-5 zeolite and characterized by XRD, SEM, N2 adsorption/desorption isotherm, NH3-TPD, and FT-IR techniques. The catalytic performance of HPW/ZSM-5 was investigated by using the decomposition reaction of cyclohexylbenzene-1-hydroperoxide (CHBHP) to phenol and cyclohexanone. The conversion rate of CHBHP was up to 97.28%. In addition, the reusability test exhibited that the high durability HPW/ZSM-5 as the conversion rate of CHBHP only decreased by 3.11% after five runs. The kinetic study of the decomposition reaction indicated it was a primary reaction. The apparent activation energy of the decomposition reaction was 102.39?kJ·mol–1 in the temperature range of 45–60℃. All results indicate that the HPW/ZSM-5 catalyst has good performance and promising applications in acid catalyzed organic chemistry.

Rational synthesis of palladium nanoparticles modified by phosphorous for the conversion of diphenyl ether to KA oil

Bai, Hong-Cun,Cao, Jing-Pei,Jiang, Wei,Wei, Yu-Lei,Xie, Jin-Xuan,Zhang, Chuang,Zhao, Liang,Zhao, Ming,Zhao, Xiao-Yan

, (2021/12/23)

Conversion of lignin-derived molecules into value-added chemicals is critical for sustainable chemistry but still challenging. Herein, phosphorus-modified palladium catalyzed the degradation of lignin-derived 4-O-5 linkage to produce KA oil (cyclohexanone-cyclohexanol oil) was reported. The reaction proceeds via a restricted partial hydrogenation-hydrolysis pathway. Phosphorus-modified palladium catalyst suppressed the full hydrogenation of diary ether, which was the key point to produce KA oil selectively. Under the optimized conditions, the 4.5 nm Pd-P NPs could catalyze the conversion of 4-O-5 linkage into KA oil in 83% selectivity with a high production rate of 32.5 mmol·g?1Pd·min?1. This study represented an original method for KA oil production.

Electrocatalytic hydrogenation of lignin monomer to methoxy-cyclohexanes with high faradaic efficiency

Chen, Henan,Kumar, Mohan,Liang, Baiyao,Peng, Tao,Wang, Miao,Yang, Chenxin,Zhang, Yun,Zhao, Wei

supporting information, p. 142 - 146 (2022/01/19)

Developing efficient renewable electrocatalytic processes in chemical manufacturing is of commercial interest, especially from biomass-derived feedstock. Selective electrocatalytic hydrogenation (ECH) of biomass-derived lignin monomers to high-value oxygen-functional compounds is promising towards achieving this goal. However, ECH has to date lacked the satisfied selectivity to upgrade lignin monomers to high-value oxygenated chemicals due to the reduction of vulnerable ?OCH3 that exists in most lignin monomers. Herein we report carbon-felt supported ternary RhPtRu catalysts with a record faradaic efficiency (FE) of 62.8% and selectivity of 91.2% to methoxy-cyclohexanes (2-methoxy-cyclohexanol and 2-methoxy-cyclohexanone) from guaiacol, via a strong inhibition effect on the cleavage of the methoxy group, representing the best performance compared to previous reports. We further conducted a brief TEA to demonstrate a profitable ECH of guaiacol to high-value methoxy-cyclohexanes using our designed RhPtRu ternary catalysts.

Process route upstream and downstream products

Process route

1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane
19073-15-5

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane

1-phenyl-acetone
103-79-7,136675-26-8

1-phenyl-acetone

2-benzyl-2-methyl-1,3-dioxolane
4362-18-9

2-benzyl-2-methyl-1,3-dioxolane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
Conditions Yield
Product distribution;
1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane
19073-15-5

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane

3-Methylcyclohexanone
591-24-2,625-96-7

3-Methylcyclohexanone

7-methyl-1,4-dioxa-spiro[4.5]decane
935-46-6

7-methyl-1,4-dioxa-spiro[4.5]decane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
Conditions Yield
Product distribution;
Cyclohex-1-enyl-(4-nitro-phenyl)-amine

Cyclohex-1-enyl-(4-nitro-phenyl)-amine

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With hydrogenchloride; water; In dimethylsulfoxide-d6; at 25 ℃; Rate constant; Mechanism; I = 0.10 M KCl;
N-(p-nitrophenyl)-N-methylcyclohex-1-en-1-amine
125519-87-1

N-(p-nitrophenyl)-N-methylcyclohex-1-en-1-amine

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
Conditions Yield
With hydrogenchloride; water; at 25 ℃; Rate constant; Mechanism; I = 0.10 M KCl;
acetophenone
98-86-2

acetophenone

cyclohexanol
108-93-0

cyclohexanol

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

Conditions
Conditions Yield
potassium hydroxide; Ru(CF3CO2)CO(PPh3)2; at 140 ℃; for 6h; Equilibrium constant; Rate constant;
With trifluoroacetic acid; carbonylbis(trifluoroacetato)bis(triphenylphosphine)ruthenium; at 140 ℃; Equilibrium constant; Thermodynamic data; ΔG (gas); reaction without reagent or in the presence of KOH, further temp.;
potassium hydroxide; Ru(CF3CO2)CO(PPh3)2; at 140 ℃; for 12h; Equilibrium constant; Rate constant; variat. KOH concentration;
dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

N-cyclohexylacetamide
1124-53-4

N-cyclohexylacetamide

Cyclohexyl isocyanate
3173-53-3

Cyclohexyl isocyanate

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
Conditions Yield
With lithium perchlorate; In acetonitrile; anodic oxidation;
16 % Chromat.
90 % Chromat.
4 % Chromat.
52 % Chromat.
cyclohexanol
108-93-0

cyclohexanol

tert-butylamine hydrochloride
10017-37-5

tert-butylamine hydrochloride

Conditions
Conditions Yield
With N,N-dichloro-t-butylamine; In tetrachloromethane; at 20 ℃; for 1h; Mechanism; Product distribution; Irradiation; other alcohol;
23 % Chromat.
90%
4-<(cyclohex-1-enyl)oxy>butan-1-ol
175907-98-9

4-<(cyclohex-1-enyl)oxy>butan-1-ol

7,12-dioxaspiro<5.6>dodecane
181-28-2

7,12-dioxaspiro<5.6>dodecane

Conditions
Conditions Yield
With acetic acid; In [D3]acetonitrile; water;
50 % Spectr.
50 % Spectr.
tetrachloromethane
56-23-5

tetrachloromethane

aniline
62-53-3

aniline

cyclohexanol
108-93-0

cyclohexanol

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

Conditions
Conditions Yield
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexanol
108-93-0

cyclohexanol

Conditions
Conditions Yield
at 200 ℃; Pr. 5: Phenol;

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