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Cas Database

100-64-1

100-64-1

Identification

  • Product Name:Cyclohexanone oxime

  • CAS Number: 100-64-1

  • EINECS:202-874-0

  • Molecular Weight:113.159

  • Molecular Formula: C6H11NO

  • HS Code:2928.00

  • Mol File:100-64-1.mol

Synonyms:(Hydroxyimino)cyclohexane;Antioxidant D;NSC 6300;OxiKhim-Styrol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides.

  • Fire-fighting measures: Suitable extinguishing media Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. Flash point data for this chemical are not available; however, it is probably combustible. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological 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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  • Manufacture/Brand:TCI Chemical
  • Product Description:Cyclohexanone Oxime >98.0%(GC)
  • Packaging:500g
  • Price:$ 201
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Cyclohexanone Oxime >98.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Cyclohexanone oxime 97%
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  • Manufacture/Brand:Matrix Scientific
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  • Manufacture/Brand:Frontier Specialty Chemicals
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:Cyclohexanone oxime 97%
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  • Manufacture/Brand:Biosynth Carbosynth
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Relevant articles and documentsAll total 219 Articles be found

Mesoporous silica gel as an effective and eco-friendly catalyst for highly selective preparation of cyclohexanone oxime by vapor phase oxidation of cyclohexylamine with air

Liu, Shuilin,You, Kuiyi,Jian, Jian,Zhao, Fangfang,Zhong, Wenzhou,Yin, Dulin,Liu, Pingle,Ai, Qiuhong,Luo, He'an

, p. 239 - 249 (2016)

A simple and environmentally benign approach to highly selective preparation of cyclohexanone oxime by vapor phase catalytic oxidation of cyclohexylamine with air over mesoporous silica gel under atmospheric pressure has been successfully developed in this work. The results demonstrate that the nonmetallic mesoporous silica gel is an effective and eco-friendly catalyst for the vapor phase selective oxidation of cyclohexylamine to cyclohexanone oxime and the surface silicon hydroxyl groups as active sites are responsible for the excellent catalytic performance of silica gel. The present silica gel catalyst has advantages of low cost, long-time stable reactivity, easy regeneration, and reusability. This method employing inexpensive mesoporous silica gel as catalyst and air as green terminal oxidant under facile conditions is a promising process and has the potential to enable sustainable production of cyclohexanone oxime from the selective oxidation of cyclohexylamine with air in industrial applications.

Preparation of cyclic ketoximes using aqueous hydroxylamine in ionic liquids

Ren, Rex X,Ou, Wei

, p. 8445 - 8446 (2001)

Cyclohexanone oxime (the precursor for making ε-caprolactam) is readily prepared from cyclohexanone using aqueous hydroxylamine in ionic liquids.

A novel hydroxylamine ionic liquid salt resulting from the stabilization of NH2OH by a SO3H-functionalized ionic liquid

Li, Zhihui,Yang, Qiusheng,Qi, Xudong,Xu, Yuanyuan,Zhang, Dongsheng,Wang, Yanji,Zhao, Xinqiang

, p. 1930 - 1932 (2015)

A SO3H-functionalized ionic liquid was used as an alternative to conventional inorganic acids in hydroxylamine stabilization, leading to the formation of a novel hydroxylamine ionic liquid salt that exhibits improved thermal stability and reactivity in the one-step, solvent-free synthesis of caprolactam in comparison with hydroxylamine hydrochloride and hydroxylamine sulfate.

A clean conversion of carbonyl compounds to oximes using silica gel supported hydroxylamine hydrochloride

Kiasat, Ali Reza,Kazemi, Foad,Nourbakhsh, Kazem

, p. 1193 - 1196 (2004)

The efficient condensation of carbonyl compounds with hydroxylamine hydrochloride under solvent free conditions is described.

Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile

Ramalingan, Chennan,Park, Yong-Tae

, p. 4536 - 4538 (2007)

(Chemical Equation Presented) An acetonitrile solution of mercury(II) chloride has been found to catalyze efficiently the conversion of a diverse range of ketoximes into their corresponding amides/lactams.

Pd/C Catalyzed selective hydrogenation of nitrobenzene to cyclohexanone oxime in the presence of NH2OH·HCl: Influence of the operative variables and insights on the reaction mechanism

Pietrobon, L.,Pontello, R.,Ronchin, L.,Sadraoui, C.,Tosetto, C.,Vavasori, A.

, (2020)

We studied the influence of temperature, solvent, pressure, catalysts type on the selectivity of nitrobenzene hydrogenation to cyclohexanone oxime (COX) in the presence of NH2OH. The best reaction conditions are: pressure 0.8 MPa, temperature 333 K, solvent ethers, and catalyst Pd/C5%. Other hydrogenation metal catalysts did not give comparable results. The amount of Pd/C influences the yield in COX, which rises above to 90 % at the highest load. The reaction profile shows that aniline is the reaction intermediate. Indeed, aniline as a substrate gives COX, though in lower yield than that achieved employing nitrobenzene. The NH2OH parallel hydrogenation to NH4Cl, influences positively the selectivity to COX. It has been observed that COX, cyclohexanone and N-cyclohexylideneaniline are in equilibrium in the reaction solution and all likely derive from nucleophilic substitutions to a common imine intermediate formed on the Pd surface, whose high activity does not need any further metal catalyst.

-

Naylor,Anderson

, p. 115 (1953)

-

-

Donaruma,Huber

, p. 965 (1956)

-

Annulation of Oxime-Ether Tethered Donor–Acceptor Cyclopropanes

Irwin, Lauren C.,Allen, Meredith A.,Vriesen, Matthew R.,Kerr, Michael A.

, p. 171 - 175 (2020)

Novel oxime-ether tethered cyclopropanes, when exposed to Yb(OTf)3 and heat, annulate to generate hydropyrrolo-oxazines products that can be taken to their respective pyrrolidines via hydrogenative N?O bond cleavage. The hydropyrrolo-oxazines are generated in a diastereoselective manner isolating the cis or trans product based on the temperature of the reaction. 20 examples of selective cis and trans hydropyrrolo-oxazines were generated in high yields by temperature control.

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones

Jahn, Ullrich,Ma?ek, Tomá?

, p. 11608 - 11632 (2021)

The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.

Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure

Matsumoto, Yohei,Kuriyama, Masami,Yamamoto, Kosuke,Nishida, Koyo,Onomura, Osamu

, p. 1312 - 1317 (2018)

A direct metal-free approach for the production of adipic acid from cyclohexane is reported. The use of N-hydroxyphthalimide (NHPI) as a catalyst in the presence of HNO3/TFA enables the direct oxidation of cyclohexane to yield adipic acid under ambient temperature and pressure via a simple procedure. This reaction proceeds through an initial oxidation of cyclohexane to cyclohexanone oxime and cyclohexanone followed by a second oxidation of these intermediates to adipic acid. NHPI plays a crucial role in both oxidation steps to achieve a high yield and selectivity for adipic acid.

One-pot conversion of cyclohexanol to ?-caprolactam using a multifunctional Na2WO4-acidic ionic liquid catalytic system

Wang, Hefang,Jia, Liyuan,Hu, Rongbin,Gao, Meidan,Wang, Yanji

, p. 58 - 64 (2017)

Na2WO4-acidic ionic liquid was used as a simple, ecofriendly, recyclable and efficient catalytic system for the one-pot conversion of cyclohexanol to ?-caprolactam. The effect of the structure of the ionic liquid on the catalytic activity of this system was investigated, and the results revealed that sulfonic acid-functionalized ionic liquids with HSO4?as an anion gave the best results. The highly efficient performance of this catalyst system was attributed to the phase-transfer behavior of the cation of the ionic liquid, the improved coordination of the substrate to bisperoxotungstate during the oxidation reaction, and the stabilization of the intermediate formed during the Beckmann rearrangement.

The influences of preparation methods on the structure and catalytic performance of single-wall carbon nanotubes supported palladium catalysts in nitrocyclohexane hydrogenation

Liu, Sihua,Hao, Fang,Liu, Pingle,Luo, He'An

, p. 22863 - 22868 (2015)

Single-wall carbon nanotubes (CNTs) supported palladium catalysts were prepared by different methods. The influences of different preparation methods on the structure and catalytic performance in nitrocyclohexane hydrogenation were investigated. The catalysts were characterized by nitrogen adsorption-desorption, XRD, TEM, hydrogen chemisorption and X-ray photoelectron spectroscopy. The results show that Pd/SWCNTs prepared by a water impregnation method provide a smaller particle size of palladium. The reduction conditions have great influence on the valence state of palladium on the support. A catalyst with smaller particle size, better dispersion and higher content of monovalent palladium exhibits better catalytic performance in nitrocyclohexane hydrogenation to cyclohexanone oxime. Pd/SWCNTs-2 prepared by a water impregnation method and reduced at 723 K has 96.4% selectivity when synthesizing cyclohexanone oxime with a 96.0% conversion from nitrocyclohexane under mild conditions of 0.3 MPa and 323 K.

Palladium supported catalysts for nitrocyclohexane hydrogenation to cyclohexanone oxime with high selectivity

Liu, Ping-Le,Zhang, Hai-Ke,Liu, Si-Hua,Yao, Zheng-Jie,Hao, Fang,Liao, Hong-Guang,You, Kui-Yi,Luo, He-An

, p. 2932 - 2938 (2013)

Different kinds of activated carbon- and carbon nanotube-supported palladium catalysts were investigated in the selective hydrogenation of nitrocyclohexane to cyclohexanone oxime under mild conditions. Carbon nanotube-supported palladium catalysts demonstrate better catalytic performance than activated carbon-supported palladium catalysts in general because of their mesoporous structures, which are favorable supports for the accessibility of the reactants to the active sites and the product desorption from the catalyst. Hydrogen chemisorption, transmission electron microscopy and X-ray photoelectron spectroscopy indicate that higher composition of Pd+ on the catalyst surface, larger palladium surface area, and better palladium dispersion contribute to an increase in the activity and selectivity toward cyclohexanone oxime. In addition, single-wall carbon nanotube-supported palladium catalysts give the best result of 97.7% conversion of nitrocyclohexane and 97.4% selectivity toward cyclohexanone oxime. On the basis of the results of GC-MS and the designed experiments, a possible reaction scheme was proposed. Brilliance in the performance: Carbon nanotube-supported palladium catalysts demonstrate better catalytic performance than activated carbon-supported palladium catalysts in general because of their mesoporous structures, which are favorable supports for the accessibility of the reactants to the active sites and the product desorption from the catalyst.

Kulevsky et al.

, p. 1154 (1973)

Hydrogenation of nitrocyclohexane to cyclohexanone oxime over Pd/CNT catalyst under mild conditions

Liao, Hong-Guang,Xiao, Yan-Juan,Zhang, Hai-Ke,Liu, Ping-Le,You, Kui-Yi,Wei, Chao,Luo, He'An

, p. 80 - 84 (2012)

The Pd/C, Pt/C, Ni/CNT and Pd/CNT catalysts were prepared by impregnation method and characterized by BET, XRD, TEM and H2 chemisorption. These catalysts were tested in the hydrogenation of nitrocyclohexane to cyclohexanone oxime. The results show that 5% Pd/CNT catalyst exhibits good performance, it gives nitrocyclohexane conversion of 97.6% and cyclohexanone oxime selectivity of 85.9% under mild conditions of 0.2 MPa and 323 K. The products include cyclohexanone oxime, cyclohexylamine, cyclohexanol and N- cyclohexylhydroxylamine. It has been found that higher temperature is in favor of the formation of cyclohexylamine, while the amount of cyclohexanol decreases with the increment of reaction temperature.

Oxidation of amines over alumina based catalysts

Rakottyay, Karol,Kaszonyi, Alexander,Vají?ek, Stanislav

, p. 33 - 41 (2010)

Amines were oxidized by molecular oxygen in the vapor phase at atmospheric pressure over alumina and silicotungstic acid/alumina catalysts. The study is focused on the influence of structure of amine and catalyst properties on the composition of the main reaction products and byproducts. Coating of γ-Al2O3 with silicotungstic acid or its semisalt can significantly enhance its catalytic activity in amine oxidation. The adsorption of amine on weak acidic sites of catalyst is essential for its oxidation to main reaction products. Cycloalkylamines are oxidized mainly to cyclic oximes (selectivity up to 64%) and Schiff bases of appropriate cycloalkanone and cycloalkylamine (selectivity up to 38%). Mainly nitriles (selectivity up to 55%) and appropriate Schiff bases (selectivity up to 54%) were observed in the oxidation products of primary alkylamines. Their molar ratio depends on the catalyst acidity and reaction conditions. 1,6-Hexanediamine is oxidized mainly to caprolactam (yield 48%) and other cyclic lactames and Schiff bases as well as to dinitrile (yield 13%).

Reduction of conjugated nitroalkenes with zinc borohydride. A mild method for converting monosubstituted nitroalkenes to nitroalkanes and disubstituted ones to oximes

Ranu,Chakraborty

, p. 5317 - 5322 (1992)

Mono-β-substituted conjugated nitroalkenes are readily reduced by zinc borohydride in 1,2-dimethoxyethane to the corresponding nitroalkanes, whereas the disubstituted ones furnish the corresponding oximes in excellent yields.

A convenient one-pot method of converting alcohols into oximes

Kiasat, Ali Reza,Kazemi, Foad,Nourbakhsh, Kazem

, p. 1809 - 1812 (2004)

The one-pot conversion of primary and secondary alcohols into oximes is reported using chromium trioxide supported on alumina and hydroxylamine hydrochloride under solvent free condition. This oxidation-oxime formation reaction has been applied to a range of aliphatic and benzylic alcohols.

Preparation of cyclic prodiginines by mutasynthesis in pseudomonas putida kt2440

Klein, Andreas Sebastian,Brass, Hannah Ursula Clara,Klebl, David Paul,Classen, Thomas,Loeschcke, Anita,Drepper, Thomas,Sievers, Sonja,Jaeger, Karl-Erich,Pietruszka, J?rg

, p. 1545 - 1552 (2018)

Prodiginines are a group of naturally occurring pyrrole alkaloids produced by various microorganisms and known for their broad biological activities. The production of nature-inspired cyclic prodiginines was enabled by combining organic synthesis with a mutasynthesis approach based on the GRAS (generally recognized as safe) certified host strain Pseudomonas putida KT2440. The newly prepared prodiginines exerted antimicrobial effects against relevant alternative biotechnological microbial hosts whereas P. putida itself exhibited remarkable tolerance against all tested prodiginines, thus corroborating the bacterium’s exceptional suitability as a mutasynthesis host for the production of these cytotoxic secondary metabolites. Moreover, the produced cyclic prodiginines proved to be autophagy modulators in human breast cancer cells. One promising cyclic prodiginine derivative stood out, being twice as potent as prodigiosin, the most prominent member of the prodiginine family, and its synthetic derivative obatoclax mesylate.

-

Robertson

, p. 395,397 (1948)

-

Site-specific catalytic activities to facilitate solvent-free aerobic oxidation of cyclohexylamine to cyclohexanone oxime over highly efficient Nb-modified SBA-15 catalysts

Ding, Wei,Mao, Liqiu,Peng, Haoyu,Yin, Dulin,Zhong, Wenzhou

, p. 3409 - 3422 (2020)

The development of highly active and selective heterogeneous catalysts for efficient oxidation of cyclohexylamine to cyclohexanone oxime is a challenge associated with the highly sensitive nitrogen center of cyclohexylamine. In this work, dispersed Nb oxide supported on SBA-15 catalysts are disclosed to efficiently catalyze the selective oxidation of cyclohexylamine with high conversion (>75%) and selectivity (>84%) to cyclohexanone oxime by O2without any addition of solvent (TOF = 469.8 h?1, based on the molar amount of Nb sites). The role of the active-site structure identity in dictating the site-specific catalytic activities is probed with the help of different reaction and control conditions and multiple spectroscopy methods. Complementary to the experimental results, further poisoning tests (with KSCN or dehydroxylation reagents) and DFT computational studies clearly unveil that the surface exposed active centers toward activation of the reactants are quite different: the surface -OH groups can catch the NH2group from cyclohexylamine by forming a hydrogen bond and lead to a more facile cyclohexylamine oxidation to desired products, while the monomeric or oligomeric Nb sites with a highly distorted structure play a key role in the dissociation of O2molecules beneficial for insertion of active oxygen species into cyclohexylamine. These catalysts exhibit not only satisfactory recyclability for cyclohexylamine oxidation but also efficiently catalyze the aerobic oxidation of a wide range of amines under solvent-free conditions.

Ammoximation: Direct Synthesis of Oximes from Ammonia, Oxygen, and Ketones

Armor, John N.

, p. 1453 - 1454 (1980)

-

Reactivity of hydroxylamine ionic liquid salts in the direct synthesis of caprolactam from cyclohexanone under mild conditions

Li, Zhihui,Yang, Qiusheng,Gao, Liya,Xu, Yuanyuan,Zhang, Dongsheng,Wang, Shufang,Zhao, Xinqiang,Wang, Yanji

, p. 83619 - 83625 (2016)

The reactivity of several sulfobutyl hydrosulfate hydroxylamine ionic liquid salts in the direct synthesis of caprolactam from cyclohexanone under mild conditions was investigated. The results showed that the cyclohexanone conversion was mainly affected by cation species in the molecules of the hydroxylamine ionic liquid salts, and hydroxylamine N,N,N-trimethyl-N-sulfobutyl hydrosulfate salt was a better choice for the direct synthesis of caprolactam. The optimum reaction condition was at 80 °C for 4 h, and the suitable molar ratio of cyclohexanone: hydroxylamine ionic liquid salt: ZnCl2 was 2: 1:3. Under the optimal reaction conditions, cyclohexanone was almost completely converted into caprolactam, corresponding to 99.1% cyclohexanone conversion and 92.0% caprolactam selectivity. Furthermore, the reaction medium acetonitrile, and the ionic liquid which was combined in the hydroxylamine salt, can be recovered after the reaction, achieving an eco-friendly route for the direct synthesis of caprolactam.

Synthesis, Characterization, and Catalytic Activities of Palladium Complexes with Phenylene-Bridged Bis(thione) Ligands

Jia, Wei-Guo,Gao, Li-Li,Wang, Zhi-Bao,Sun, Li-Ying,Han, Ying-Feng

, p. 1946 - 1954 (2019)

The neutral phenylene-bridged bis(thione) compounds, 1,3-bis(3′-ethylimidazolyl-2′-thione)benzene (Betb), 1,3-bis(3′-butylimidazolyl-2′-thione)benzene (Bbtb), and 1,3-bis(3′-allylimidazolyl-2′-thione)benzene (Batb), have been synthesized and characterized. Reactions of palladium precursor PdCl2(CH3CN)2 with phenylene-bridged bis(thione) ligands in 1:2 ratio resulted in the formation of the complexes: PdCl2(L)2 (L = Betb, 3a; L = Bbtb, 3b; L = Batb, 3c, respectively). In contrast, treatment of the ligands with PdCl2(CH3CN)2 in 1:1 ratio gave cyclometalation palladium complexes Pd2+Cl(L-) (L = Betb-H, 4a; L = Bbtb-H, 4b; L = Batb-H, 4c) through the metal-induced C-H activation. Complexes 4a-c can also be obtained by the reaction of bis(thione) ligands and PdCl2 in 1:1 ratio. The reaction of 3a-c with additional PdCl2(CH3CN)2 also afforded complexes 4a-c. All ligands and palladium complexes were fully characterized by one-/two-dimensional NMR spectra, mass spectrometry, and infrared spectrometry. And the molecular structures of 3a-c, 4a, and 4c have been determined by the single-crystal X-ray diffraction method. Furthermore, the detailed spectroscopic properties and catalytic activities of the complexes for the reduction of nitro compounds were discussed in terms of the modification of the coordination ligands to the center metal.

Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane

-

, (2021/06/13)

The invention relates to a method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane. The method comprises the following steps: (1) carrying out oxidation nitration on cyclohexane and NOx to generate adipic acid, nitrocyclohexane, nitrogen oxides and a byproduct-A, and separating to obtain crude adipic acid and nitrocyclohexane; (2) carrying out catalytic hydrogenation on the obtained nitrocyclohexane and hydrogen to generate cyclohexanone-oxime and a small amount of cyclohexylamine, separating to obtain crude cyclohexanone-oxime and cyclohexylamine, and enabling cyclohexylamine to be directly used as a byproduct or to be continuously converted into cyclohexanone-oxime. and (3) partially oxidizing the cyclohexylamine obtained in the previous step with molecular oxygen to obtain an oxidation reaction product consisting of cyclohexanone-oxime, a byproduct B and possibly unconverted cyclohexylamine, and then separating the oxidation reaction product without separation, or firstly separating part or all of water in the oxidation reaction product, carrying out hydrogenation amination reaction under the action of a catalyst, or carrying out hydrogenation and amination reaction, or only carrying out hydrogenation reaction, and then separating to obtain the cyclohexanone-oxime. The method can realize high-selectivity co-production of adipic acid and cyclohexanone-oxime, and is short in process flow, low in equipment investment and low in material consumption, energy consumption and cost.

Poly(N-vinylimidazole): A biocompatible and biodegradable functional polymer, metal-free, and highly recyclable heterogeneous catalyst for the mechanochemical synthesis of oximes

Fahim, Hoda,Ghaffari Khaligh, Nader,Gorjian, Hayedeh

, p. 2007 - 2012 (2022/01/08)

The catalytic activity of poly(N-vinylimidazole), a biocompatible and biodegradable synthetic functional polymer, was investigated for the synthesis of oximes as an efficient, halogen-free, and reusable heterogeneous catalyst. The corresponding oximes were afforded in high to excellent yields at room temperature and in short times using the planetary ball mill technique. Some merits, such as the short reaction times and good yields for poorly active carbonyl compounds, and avoiding toxic, expensive, metal-containing catalysts, and hazardous and flammable solvents, can be mentioned for the current catalytic synthesis of the oximes. Furthermore, the heterogeneous organocatalyst could be easily separated after the reaction, and the regenerated catalyst was reused several times with no significant loss of its catalytic activity.

Process route upstream and downstream products

Process route

nitrobenzene
98-95-3,26969-40-4

nitrobenzene

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

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

N-phenyl-2-cyclohexylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; In diethyl ether; for 4h; Catalytic behavior;
48 %Chromat.
20 %Chromat.
6 %Chromat.
10 %Chromat.
16 %Chromat.
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

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

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With aluminum (III) chloride; 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; In diethyl ether; for 4h; Catalytic behavior;
19 %Chromat.
25 %Chromat.
26 %Chromat.
14 %Chromat.
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

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

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

aniline
62-53-3

aniline

Conditions
Conditions Yield
With 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; platinum(II) chloride; In diethyl ether; for 4h; Catalytic behavior;
54 %Chromat.
6 %Chromat.
24 %Chromat.
N-phenyl(methylidene)cyclohexanamine
2211-66-7

N-phenyl(methylidene)cyclohexanamine

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

2-cyclohexyl-3-phenyl-1,2-oxaziridine
21711-00-2,75768-08-0,75780-72-2

2-cyclohexyl-3-phenyl-1,2-oxaziridine

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With sodium hydroxide; 1,1,1-trifluoro-2-propanone; dihydrogen peroxide; N-tosylimidazole; In methanol; at 5 ℃;
32%
26%
27%
cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

nitrosocyclohexane
2696-95-9

nitrosocyclohexane

Conditions
Conditions Yield
With tert.-butylnitrite; N-hydroxyphthalimide; In tetradeuterioacetic acid; at 80 ℃; for 6h;
8%
18%
With tert.-butylnitrite; In tert-butyl alcohol; at 20 ℃; for 16h;
cyclohexanone-O-(phenylmethyl)oxime
19731-71-6

cyclohexanone-O-(phenylmethyl)oxime

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

cyclohexylideneamine
22554-30-9

cyclohexylideneamine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
In various solvent(s); at 149.84 ℃; for 264h; Further Variations:; Solvents; Kinetics; Product distribution;
trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

1-nitrocyclohexane
1122-60-7

1-nitrocyclohexane

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

cyclohexanone O-methyloxime
13858-85-0

cyclohexanone O-methyloxime

Conditions
Conditions Yield
at 50 ℃;
hexahydro-2H-oxepin-2-one
502-44-3,24980-41-4,80137-66-2

hexahydro-2H-oxepin-2-one

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

Conditions
Conditions Yield
With aluminum oxide; ammonia; water; tungsten(VI) oxide; 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 79.84 ℃;
25%
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

aniline
62-53-3

aniline

Conditions
Conditions Yield
With 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; scandium tris(trifluoromethanesulfonate); In diethyl ether; for 4h; Reagent/catalyst; Catalytic behavior;
7 %Chromat.
93 %Chromat.
With 5% Pd/C; hydroxylamine hydrochloride; hydrogen; In diethyl ether; at 59.84 ℃; for 20h; under 6000.6 Torr; Reagent/catalyst; Solvent; Pressure; Catalytic behavior;
dicyclohexyl ketone
119-60-8

dicyclohexyl ketone

isopentyl nitrite
110-46-3

isopentyl nitrite

cyclohexanone-oxime
100-64-1

cyclohexanone-oxime

isopentyl cyclohexanecarboxylate
25183-19-1

isopentyl cyclohexanecarboxylate

Conditions
Conditions Yield
dicyclohexyl ketone; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere; Schlenk technique;
isopentyl nitrite; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere; Schlenk technique;
31%

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  • Shanghai Upbio Tech Co.,Ltd
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  • SAGECHEM LIMITED
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  • Win-Win chemical Co.Ltd
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  • GIHI CHEMICALS CO.,LIMITED
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