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Cyclohexanone oxime

CAS：100-64-1
MW:113.16
MF：C6H11NO

Prisms, liquid or light tan crystalline solid.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Cyclohexanone oxime

1.2 Synonyms: AKOS BBS-00004405; Antioxidant D; CCYLOHEXANONE OXIME; CHO; CYCLOHEXAN-1-ONE OXIME; Cyclohexanone, oxime; Cyclohexylimine; EINECS 202-874-0; HYDROXYIMINOCYCLOHEXANE; LABOTEST-BB LT00853999; MFCD00001660; N-cyclohexylidenehydroxylamine; N-Hydroxycyclohexanimine;

1.3 CAS No.: 100-64-1

1.4 CID: 7517

1.5 EINECS: 202-874-0

1.6 Molecular Formula: C6H11NO

1.7 Inchi: InChI=1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2

1.8 InChkey: VEZUQRBDRNJBJY-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CCC(=NO)CC1

1.10 Isomers Smiles: C1CCC(=NO)CC1

2. Properties

2.1 Vapour pressure: 3.91 (NTP, 1992) (Relative to Air)

2.2 Solubility: 17.7g/l

2.3 VaporDensity: 3.91 (NTP, 1992) (Relative to Air)

2.4 Appearance: Off-white to beige-brownish Crystalline Powder, Crystals, or Chunks

2.5 Storage: Ambient temperatures.

2.6 Chemical Properties: tan crystals

2.7 Color/Form: HEXAGONAL PRISMS FROM PETROLEUM ETHER

2.8 pKa: 12.42±0.20(Predicted)

2.9 Water Solubility: H2O: <0.1 g/100 mL at 20 oC

2.10 Spectral Properties: SADTLER REFERENCE NUMBER: 276 (IR, PRISM); 95 (IR, GRATING)
IR: 1677 (Coblentz Society Spectral Collection)
UV: 7-91 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 6160 (Sadtler Research Laboratories Spectral Collection)
MASS: 51 (Aldermaston, Eight Peak Index of Mass Spectra, UK)

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2.11 Stability: Stable. Combustible. Incompatible with strong oxidizing agents. Reacts violently with fuming sulfuric acid at elevated temperature.

2.12 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Description

PHYSICAL DESCRIPTION: Prisms, liquid or light tan crystalline solid. (NTP, 1992)

Prisms, liquid or light tan crystalline solid. (NTP, 1992)|Liquid

Prisms, liquid or light tan crystalline solid. (NTP, 1992)

3.2 General Description: Prisms, liquid or light tan crystalline solid.

3.3 Methods of Manufacturing: Cyclohexanone oxime is an intermediate product in the production of caprolactam.

3.4 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 Preparation Products

3.5 Usage: In prepn of caprolactam. Antioxidant.

4. Safety and Handling

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

4.2 Report: Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.3 Safety: Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. Violent reaction with oleum (fuming sulfuric acid) above 150°C. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes:
Xn: Harmful
Risk Statements about (Hydroxyimino)cyclohexane (100-64-1):
R22 Harmful if swallowed.
Safety Statements about (Hydroxyimino)cyclohexane (100-64-1):
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
Attentions:
1. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid ingestion and inhalation. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.

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4.4 Specification: tan crystals
Safety Statements:36/37/39
36/37/39:Wear suitable protective clothing, gloves and eye/face protection

4.5 Toxicity

1.	msc-mus:lym 1938 mg/L	MUREAV Mutation Research. 204 (1988),149.
2.	orl-rat LD:>500 mg/kg	NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),26.
3.	ipr-mus LD50:250 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

100-64-1Total: 108 Synthesis Route

98-95-3 66 Suppliers

100-64-1 63 Suppliers

98-95-3 66 Suppliers

100-64-1 63 Suppliers

108-94-1 282 Suppliers

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8. Precursor and Product

precursor:

98-95-3

108-94-1

product:

956-09-2

765-87-7

124-09-4

873-92-7

54-95-5

780-02-9

371-90-4

4903-39-3

105-60-2

108-91-8

9. Computed Properties

Molecular Weight：113.16g/mol
Molecular Formula：C₆H₁₁NO
Compound Is Canonicalized：True
Exact Mass：1.2
XLogP3-AA：113.084063974
Monoisotopic Mass：113.084063974
Complexity：90.7
Rotatable Bond Count：0
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：2
Topological Polar Surface Area：32.6
Heavy Atom Count：：8
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBiIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAAAAAAAHAAECAAACAiBAAAAAAAQAAAgAQAgAAAAAAAAAAAAAAAwAAAAAAIAAAAAAAAAAAAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

BRN: 1616769

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).

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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).

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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 extrac-tion 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 recom-mended.

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 recom-mended. 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.

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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

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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.

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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.

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.]

Storage Conditions: Cyclohexanone oxime is an intermediate product in the production of caprolactam.

Reactive Group: Oximes

Reactivity Profile: CYCLOHEXANONE OXIME reacts violently with fuming sulfuric acid at temperatures > 302° F. (NTP, 1992). Several explosions or violent decompositions have occurred during distillation of aldoximes, 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.

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Fire Hazards: Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Nonfire Spill Response: SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

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Personal Protective Equipment: RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Metabolism: CYCLOHEXYLAMINE WAS DEAMINATED TO CORRESPONDING KETONES BY RABBIT LIVER MICROSOMES IN PRESENCE OF NADPH & MOL OXYGEN. CYCLOHEXANONE OXIME, IDENTIFIED FROM INCUBATION MIXTURES, MAY BE AN INTERMEDIATE OF MICROSOMAL DEAMINATION OF ALICYCLIC PRIMARY AMINES.

First Aid: EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

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Mesh Entry Terms: cyclohexanone oxime

Production: 250,000,000 - 500,000,000 lb

Manufacturing Info: All other basic organic chemical manufacturing|Cyclohexanone, oxime: ACTIVE

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12. Related Questions

: What is the application of Cyclohexanone oxime in the chemical industry?Cyclohexanone oxime, also known as Cyclohexanone oxime, is a white prismatic crystal that is soluble in water, ethanol, ether, and methanol. It is a fine chemical intermediate in the production of fin..

13. Realated Product Infomation