Cyclohexanone Oxime

less than 1 mg/mL at 68 °F (NTP, 1992)

SOL IN WATER, ALCOHOL, ETHER, METHYL ALCOHOL

403 to 410 °F at 760 mmHg (NTP, 1992)

206-210 °C

192 to 196 °F (NTP, 1992)

89-90 °C

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

Solid; [HSDB] Liquid or light tan solid; mp = 89-91 deg C; [CAMEO] White chunks or powder; [Alfa Aesar MSDS]

This chemical does not meet GHS hazard criteria for 1.9% (5 of 262) of reports.

Danger

H228 (55%): Flammable solid [Danger Flammable solids]

P210, P240, P241, P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P319, P330, P337+P317, P370+P378, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 262 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Cyclohexanone, oxime

Status: Active Update: 27-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7659

Cyclohexanone oxime: Does not have an individual approval but may be used under an appropriate group standard

Mixtures of cyclohexanone and oxime (varying ratios) produced anesthesia, conjunctivitis, and increased aggression in oral studies of rats; Emergency treatment: Methemoglobinemia; [HSDB] May peroxidize; [CAMEO] Increased methemoglobin levels observed in dermal lethal-dose study or rabbits; Progressive anemia with increased splenic hemosiderin deposition and hematopoiesis observed in 90-day gavage study of rats; No changes in sperm motility or vaginal cytological parameters seen; Limited evidence of mutagenicity in vitro and no evidence in vivo; A major metabolite, cyclohexanone (CAS # 108-94-1), caused reduced fetal body weight and increased frequency of retardation of ossification at levels maternally toxic in inhalation study of rats (LOAEL for maternal and developmental toxicity both equal 5,600 mg/m3/day); [EPA ChAMP: Screening Level Hazard Characterization] A strong eye irritant; Harmful by ingestion; Prolonged or repeated ingestion exposure may cause injury to the hematopoietic system; [ECHA REACH Registrations] An irritant; Toxic by ingestion; [Alfa Aesar MSDS]

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.

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.

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.

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)

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=100-64-1]

Cyclohexanone oxime was examined for mutagenic activity in Salmonella typhimurium tester strains TA98, TA100, TA1535, TA1537 and TA1538 in the presence and absence of metabolic activation provided by rat liver S9 fraction. The method used to induce liver enzyme activities was not reported. The test article was not mutagenic in the plate incorporation assay at concentrations of 5 to 5000 ug/plate with or without activation. The investigators observed toxicity at the high dose level, but did not report the degree of toxicity or in which strain(s) it was observed.

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.

Used to make caprolactam; [HSDB] A closed-system intermediate (CSI); [EPA ChAMP: Screening Level Hazard Characterization] Used in coatings; [ECHA REACH Registrations]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

IN PREPN OF CAPROLACTAM