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Cyclohexanone oxime

Product Name
Cyclohexanone oxime
CAS No.
100-64-1
Chemical Name
Cyclohexanone oxime
Synonyms
CHO;Antioxidant D;Cyclohexanonoxim;AKOS BBS-00004405;Cyclohexane oxime;Cyclohexanon-oxime;Cylohexanone oxime;Cyclohexanone oxium;CCYLOHEXANONE OXIME;CYCLOHEXANONE OXIME
CBNumber
CB8487050
Molecular Formula
C6H11NO
Formula Weight
113.16
MOL File
100-64-1.mol
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Cyclohexanone oxime Property

Melting point:
86-89 °C (lit.)
Boiling point:
206-210 °C (lit.)
Density 
1.0125 (rough estimate)
vapor pressure 
1.78Pa at 20℃
refractive index 
1.4860 (estimate)
Flash point:
90 °C
storage temp. 
Store below +30°C.
solubility 
17.7g/l
pka
12.42±0.20(Predicted)
form 
Crystalline Powder, Crystals, or Chunks
color 
Off-white to beige-brownish
Water Solubility 
<0.1 g/100 mL at 20 ºC
BRN 
1616769
Dielectric constant
3.0(89℃)
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents. Reacts violently with fuming sulfuric acid at elevated temperature.
InChIKey
VEZUQRBDRNJBJY-UHFFFAOYSA-N
LogP
1.265 at 25℃
CAS DataBase Reference
100-64-1(CAS DataBase Reference)
NIST Chemistry Reference
Cyclohexanone, oxime(100-64-1)
EPA Substance Registry System
Cyclohexanone oxime (100-64-1)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36/37/39
WGK Germany 
1
RTECS 
GW1925000
TSCA 
Yes
HS Code 
29280090
Hazardous Substances Data
100-64-1(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C102202
Product name
Cyclohexanone oxime
Purity
97%
Packaging
500g
Price
$44
Updated
2024/03/01
Sigma-Aldrich
Product number
C102202
Product name
Cyclohexanone oxime
Purity
97%
Packaging
100g
Price
$45.5
Updated
2024/03/01
TCI Chemical
Product number
C0490
Product name
Cyclohexanone Oxime
Purity
>98.0%(GC)
Packaging
25g
Price
$25
Updated
2024/03/01
TCI Chemical
Product number
C0490
Product name
Cyclohexanone Oxime
Purity
>98.0%(GC)
Packaging
500g
Price
$286
Updated
2024/03/01
Alfa Aesar
Product number
A19820
Product name
Cyclohexanone oxime, 97%
Packaging
100g
Price
$19.65
Updated
2024/03/01
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Cyclohexanone oxime Chemical Properties,Usage,Production

Chemical Properties

Cyclohexanone oxime, a white crystalline solid, has a molecular weight of 113.16 and a melting point of 90 C. It is soluble in water and ethanol (Lide, 1992). This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer. Cyclohexanone oxime is produced by the condensation of cyclohexanone with hydroxylamine sulfate or hydroxylamine phosphate (Fisher and Cresentini, 1985).

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).

Uses

Cyclohexanone Oxime is used as a cathodic inhibitor which inhibits the corrosion of aluminum in hydrochloric acid.

Preparation

To a cooled, well-stirred solution of 2 gm (0.0115 mole) of 1-chloro-l-nitrosocyclohexane dissolved in a mixture of 20 ml of ethanol and 10 ml of distilled water is added, in small increments, enough sodium borohydride until the color has been discharged. The reaction mixture, which is neutral, is acidified slightly to pH 4. The product is separated by exhaustive extrac­tion with ether. The ether extract is dried over sodium sulfate, filtered, and freed of ether by evaporation. The colorless crystal mass is pressed dry on a clay plate and recrystallized from petroleum ether to afford 0.94 gm (61%), m.p. 89-90°C.
The partial reduction of aliphatic nitro compounds was mentioned as early as the turn of this century. However, only with the commercialization of nitroalkanes did these reactions achieve any real significance. Among the chemical reducing agents, zinc dust and acetic acid have been recom­mended.

Hydrogenation of nitrocyclohexane on a silver dichromate catalyst has recently been patented. In this procedure, it is said to be important to control the hydrogen take-up to prevent hydrogenation of the oxime to the hydroxylamine. This is accomplished by venting hydrogen off as soon as the theoretical quantity of hydrogen has been used up to convert the nitro compound to the oxime.
Olefinic nitro compounds have been reduced to the saturated oxime with hydrogen and a palladium-on-carbon catalyst. To maximize the yield of oxime, 0.5-1.0 mole of hydrogen chloride per mole of nitroolefin must be present. Since the by-products contain crude ketones also, a posttreatment with hydroxylamine hydrochloride and sodium acetate has been recom­mended. By this means, 1-nitrocyclooctene has been converted to cyclooctanone oxime [b.p. 63°C (0.08 mm Hg), m.p. 41.7-42.7°C] and 1-nitro-l-octadecene has been converted to stearaldoxime (m.p. 88-89.8°C). Whether this method is confined to 1-olefin derivatives is not clear.
Nitro olefins have also been reduced with zinc dust and acetic acid, to produce oximinoalkanes. The preparation of 5-ethyl-3-nonanone oxime gives the necessary details. To be noted is that the carbon bearing nitro group in the starting material also bears the double bond. Whether this structural feature is essential if the reduction is to stop at the oxime stage may need further elucidation.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 76, 1943
The Journal of Organic Chemistry, 48, p. 2766, 1983 DOI: 10.1021/jo00164a026
Tetrahedron Letters, 28, p. 4557, 1987 DOI: 10.1016/S0040-4039(00)96563-8

General Description

Prisms, liquid or light tan crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Cyclohexanone oxime reacts violently with fuming sulfuric acid at temperatures > 302° F. . Several explosions or violent decompositions have occurred during distillation of aldooximes, which may be attributable to the formation of peroxides of various types. This is especially the case in the presence of acid, Chem. Eng. News, 1974, 52(35), 3. A nickel catalyzed aldoxime rearrangement to an amide, went out of control after changing the solvent employed, J. Loss Prev., 1993, 6(2), 69.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Cyclohexanone oxime emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for Cyclohexanone oxime are not available; however, Cyclohexanone oxime is probably combustible.

Flammability and Explosibility

Highly flammable

Purification Methods

Crystallise the oxime from water or pet ether (b 60-80o). [Bousquet Org Synth Coll Vol II 313 1943, Beilstein 7 III 32, 7 IV 21.]

Cyclohexanone oxime Preparation Products And Raw materials

Raw materials

Preparation Products

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Cyclohexanone oxime Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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76
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
Advantage
61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10194
Advantage
62
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696;
Email
info@hanhongsci.com
Country
China
ProdList
42982
Advantage
64
Shandong Xiya Chemical Co., Ltd
Tel
4009903999 13355009207
Fax
0539-6365991
Email
3007715519@qq.com
Country
China
ProdList
18736
Advantage
57
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12990
Advantage
57
BEST-REAGENT
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11726
Advantage
57
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View Lastest Price from Cyclohexanone oxime manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Cyclohexanone oxime 100-64-1
Price
US $30.00-9.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-09-22
Hebei Mojin Biotechnology Co., Ltd
Product
Cyclohexanone oxime 100-64-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-11-10
Hebei Guanlang Biotechnology Co., Ltd.
Product
Cyclohexanone oxime 100-64-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2022-10-10

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