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?????????
????????? ??? ???
?? ??:
100-64-1
???:
?????????
???(??):
(????????)?????;?????????;?????????;????????
???:
Cyclohexanone oxime
???(??):
CHO;Cyclohexanonoxim;AKOS BBS-00004405;Cyclohexane oxime;Cyclohexanon-oxime;N-Cyclohexylidenehydroxylamine;Antioxidant D;Cylohexanone oxime;CYCLOHEXANONE OXIME;CCYLOHEXANONE OXIME
CBNumber:
CB8487050
???:
C6H11NO
??? ??:
113.16
MOL ??:
100-64-1.mol
MSDS ??:
SDS

????????? ??

???
86-89 °C (lit.)
?? ?
206-210 °C (lit.)
??
1.0125 (rough estimate)
???
1.78Pa at 20℃
???
1.4860 (estimate)
???
90 °C
?? ??
Store below +30°C.
???
17.7g/L
??? ??
??? ??, ?? ?? ???
?? ?? (pKa)
12.42±0.20(Predicted)
??
????? ???? ????
???
20°C?? <0.1g/100mL
BRN
1616769
Henry's Law Constant
4.3×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
3.0(89℃)
???
????. ?? ??. ?? ???? ???? ????. ???? ????? ???? ???.
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
1.265 at 25℃
CAS ??????
100-64-1(CAS DataBase Reference)
NIST
Cyclohexanone, oxime(100-64-1)
EPA
Cyclohexanone oxime (100-64-1)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xn
?? ???? ?? 22
????? 36/37/39
WGK ?? 1
RTECS ?? GW1925000
TSCA TSCA listed
HS ?? 29280090
???? ??? 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Oral
?? ?? ??? 100-64-1(Hazardous Substances Data)
????(GHS): Exclamation Mark (GHS07)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H302 ??? ??? ?? ?? ?? - ?? ?? 4 ?? P264, P270, P301+P312, P330, P501
??????:
NFPA 704
2
2 0

????????? MSDS


Antioxidant D

????????? C??? ??, ??, ??

??? ??

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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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).

?? ??

Prisms, liquid or light tan crystalline solid.

??? ?? ??

Insoluble in water.

?? ???

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.

????

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

????

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.]

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