Cyclohexanone oxime

Base Information

• Chemical Name: Cyclohexanone oxime
• CAS No.: 100-64-1
• Deprecated CAS: 136056-95-6,136057-01-7,1071540-61-8,1071540-61-8,136057-01-7
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 2928.00
• European Community (EC) Number: 202-874-0
• NSC Number: 6300
• UN Number: 2811
• UNII: 2U60L00CGF
• DSSTox Substance ID: DTXSID4021842
• Nikkaji Number: J45.666G
• Wikipedia: Cyclohexanone_oxime
• Wikidata: Q1147519
• ChEMBL ID: CHEMBL137035
• Mol file: 100-64-1.mol

Synonyms:cyclohexanone oxime

Chemical Property of Cyclohexanone oxime

Chemical Property:

• Appearance/Colour: tan crystals
• Vapor Pressure: 0.0879mmHg at 25°C
• Melting Point: 86-89 °C(lit.)
• Refractive Index: 1.529
• Boiling Point: 208 °C at 760 mmHg
• PKA: 12.42±0.20(Predicted)
• Flash Point: 112.4 °C
• PSA: 32.59000
• Density: 1.1 g/cm³
• LogP: 1.78070
• Storage Temp.: Store below +30°C.
• Solubility.: 17.7g/l
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 90.7
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

Cyclohexanone Oxime >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Oximes
• Canonical SMILES: C1CCC(=NO)CC1
• Uses: Cyclohexanone oxime is used in a wide variety of industrial applications. Primarily, it is used as a captive intermediate in the synthesis of caprolactam, which is polymerized in the production of polycaprolactam (Nylon-6) fibers and plastics (Fisher and Cresentini, 1985; NCI, 1985). The annual U.S. caprolactam production is over 500,000 tons (NCI, 1985). Approximately 90% of the monomer is used to produce fibers for clothing, carpets, home furnishings, and tire cording. The remaining 10% is used to produce nylon resins for food packaging film, extrusion compounds for bristle filaments and wire coatings, and molded plastics for automobiles and appliances (NCI, 1985). Cyclohexanone oxime is also thought to be an intermediate in the oxidative metabolism of sodium cyclamate, an artificial sweetener (Unger and McMahon, 1981). Cyclohexanone Oxime is used as a cathodic inhibitor which inhibits the corrosion of aluminum in hydrochloric acid.

Technology Process of Cyclohexanone oxime

There total 165 articles about Cyclohexanone oxime which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-cyclohexyl-hydroxylamine (2211-64-5) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethylsulfoxide-d6; at 45 ℃; for 0.5h;

DOI:10.1055/s-0036-1588457

Reference yield: 91.0%

cyclohexylamine (108-91-8,157973-60-9) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With diperoxydodecanedioic acid; In N,N-dimethyl-formamide; at 20 - 55 ℃; for 0.333333h;

DOI:10.1039/c5nj00801h

Reference yield: 90.0%

trimethylsilyl cyclohexyl ether (13871-89-1) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With trichloroisocyanuric acid; hydroxylamine hydrochloride; In neat (no solvent); at 100 ℃; for 4.25h; Green chemistry;

DOI:10.1080/10426507.2014.990015

upstream raw materials:

cyclohexyl-1-phenyl-1-hydroperoxide

cyclohexane

1-chloro-1-nitrosocyclohexane

1-chloro-1-nitrocyclohexane

Downstream raw materials:

caprolactam

cyclohexanone O-ethyl oxime

cyclohexanone O-4-nitrobenzoyl oxime

2-isopropylidenecyclohexan-1-one

Refernces

• 1、 Zhao, Song,Xie, Wei,Yang, Junxia,Liu, Yueming,Zhang, Yingtian,Xu, Biliang,Jiang, Jin-Gang,He, Mingyuan,Wu, Peng. "An investigation into cyclohexanone ammoximation over Ti-MWW in a continuous slurry reactor". . p. 1 - 8. Retrieved 2011.
• 2、 Hirabayashi, Tomotaka,Sakaguchi, Satoshi,Ishii, Yasutaka. "A new route to lactam precursors from cycloalkanes: Direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-Butyl nitrite and N-hydroxyphthalimide". . p. 1120 - 1123. Retrieved 2004.
• 3、 Peng, Ling,Liu, Chan,Li, Na,Zhong, Wenzhou,Mao, Liqiu,Kirk, Steven Robert,Yin, Dulin. "Direct cyclohexanone oxime synthesis: Via oxidation-oximization of cyclohexane with ammonium acetate". . p. 1436 - 1439. Retrieved 2020.
• 4、 Moormann, Alan E.,Metz, Sue,Toth, Mihaly V.,Moore, William M.,Jerome, Gina,Kornmeier, Christine,Manning, Pamela,Hansen Jr., Donald W.,Pitzele, Barnett S.,Webber. "Selective heterocyclic amidine inhibitors of human inducible nitric oxide synthase". . p. 2651 - 2653. Retrieved 2001.
• 5、 Merritt,Ruff. "". . p. 1392. Retrieved 1964.
• 6、 Rong, Mark K.,Holtrop, Flip,Bobylev, Eduard O.,Nieger, Martin,Ehlers, Andreas W.,Slootweg, J. Chris,Lammertsma, Koop. "Atypical and Asymmetric 1,3-P,N Ligands: Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes". . p. 14007 - 14016. Retrieved 2021.
• 7、 Dutta, Papia,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli. "Dual nature of polyethylene glycol under microwave irradiation for the clean synthesis of oximes". . p. 505 - 508. Retrieved 2014.
• 8、 McCoy,Gohlke. "-". . p. 286. Retrieved 1957.
• 9、 Schuemperli, Martin T.,Hammond, Ceri,Hermans, Ive. "Reactivity of α-amino-peroxyl radicals and consequences for amine oxidation chemistry". . p. 11002 - 11007. Retrieved 2012.
• 10、 Reid,Wilcox. "-". . p. 646. Retrieved 1975.