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Cyclohexanonoxim
CHO · Cyclohexanonoxim · AKOS BBS-00004405 · Cyclohexane oxime · Cyclohexanon-oxime · N-Cyclohexylidenehydroxylamine · Antioxidant D · Cylohexanone oxime
Identifikatoren & physikalische Daten
| CAS No. | 100-64-1 |
|---|---|
| Summenformel | C6H11NO |
| Durchschnittliche Molmasse | 113,16 g/mol |
| Monoisotopische Masse | 113,08406397 g/mol |
| SMILES | ON=C1CCCCC1 |
| InChIKey | VEZUQRBDRNJBJY-UHFFFAOYSA-N |
| PubChem CID | 7517 |
| ChEMBL | CHEMBL137035 |
| EC No. | 202-874-0 |
| DTXSID | DTXSID4021842 |
| Lokaler Name | Cyclohexanonoxim |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 32,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 90,7 |
| Stoffklassen | Nitrogen Compounds -> Oximes |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Color/Form | HEXAGONAL PRISMS FROM PETROLEUM ETHER |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)SOL IN WATER, ALCOHOL, ETHER, METHYL ALCOHOL17.7g/l<0.1 g/100 mL at 20 ºC |
| Siedepunkt | 403 to 410 °F at 760 mmHg (NTP, 1992)206-210 °C206-210 °C (lit.) |
| Schmelzpunkt | 192 to 196 °F (NTP, 1992)89-90 °C86-89 °C (lit.) |
| Dampfdichte | 3.91 (NTP, 1992) - Heavier than airwill sink (Relative to Air) |
| Physical Description | Prisms, liquid or light tan crystalline solid. (NTP, 1992)[HSDB] Liquid or light tan solidmp = 89-91 deg C[CAMEO] White chunks or powder[Alfa Aesar MSDS] |
| Dichte | 1.0125 (rough estimate) |
| Dampfdruck | 1.78Pa at 20℃ |
| Brechungsindex | 1.4860 (estimate) |
| Flammpunkt | 90 °C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 12.42±0.20(Predicted) |
| Aggregatzustand | Crystalline Powder, Crystals, or Chunks |
| Farbe | Off-white to beige-brownish |
| BRN | 1616769 |
| Henry-Konstante | 4.3×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 3.0(89℃) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. Reacts violently with fuming sulfuric acid at elevated temperature. |
| InChI | 1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 |
| InChIKey | VEZUQRBDRNJBJY-UHFFFAOYSA-N |
| SMILES | O\N=C1/CCCCC1 |
| LogP (Verteilungskoeffizient) | 1.265 at 25℃ |
| CAS Datenbank | 100-64-1(CAS DataBase Reference) |
| NIST chemische Informationen | Cyclohexanone, oxime(100-64-1) |
| EPA chemische Informationen | Cyclohexanone oxime (100-64-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (5 of 262) of reports.DangerH228 (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. |
|---|---|
| Regulatorische Informationen | Chemical: Cyclohexanone, oximeStatus: Active Update: 27-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7659Cyclohexanone oxime: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Cyclohexanone, oxime: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992) |
| Gefahrenübersicht | Mixtures of cyclohexanone and oxime (varying ratios) produced anesthesia, conjunctivitis, and increased aggression in oral studies of ratsEmergency treatment: Methemoglobinemia[HSDB] May peroxidize[CAMEO] Increased methemoglobin levels observed in dermal lethal-dose study or rabbitsProgressive anemia with increased splenic hemosiderin deposition and hematopoiesis observed in 90-day gavage study of ratsNo changes in sperm motility or vaginal cytological parameters seenLimited evidence of mutagenicity in vitro and no evidence in vivoA 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 irritantHarmful by ingestionProlonged or repeated ingestion exposure may cause injury to the hematopoietic system[ECHA REACH Registrations] An irritantToxic by ingestion[Alfa Aesar MSDS] |
| Reaktive Gruppe | Oximes |
| Reactivity Alerts | Peroxidizable Compound |
| 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. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Flam. Sol. 2 (55%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | 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. |
| Freisetung ohne Brand | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | 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) |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Ongoing Test Status | 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] |
| TSCA Test Submissions | 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. |
| Non-Human Toxicity Excerpts | ACUTE TOXIC EFFECTS OF CYCLOHEXANONE & OXIME & MIXTURES OF BOTH IN DIFFERENT RATIOS WERE TESTED BY ORAL PROBING IN RATS. THE ANESTHETIC EFFECT, CONJUNCTIVITIS & INCREASED AGGRESSIONS WERE PARTICULARLY STRIKING. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29280090 |
| RTECS-Nr. | GW1925000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 100-64-1(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
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).