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Cyclohexanone information


Not to be confused with Cyclexanone.
Cyclohexanone[1][2]
Skeletal formula of cyclohexanone
Skeletal formula of cyclohexanone
Ball-and-stick model of cyclohexanone
Ball-and-stick model of cyclohexanone
Skeletal formula viewed side-on, showing the non-planar conformation
Skeletal formula viewed side-on, showing the non-planar conformation
Ball-and-stick model of cyclohexanone viewed side-on, showing the non-planar conformation
Ball-and-stick model of cyclohexanone viewed side-on, showing the non-planar conformation
Names
Preferred IUPAC name
Cyclohexanone
Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
Identifiers
CAS Number
  • 108-94-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17854 checkY
ChEMBL
  • ChEMBL18850 checkY
ChemSpider
  • 7679 checkY
DrugBank
  • DB02060 checkY
ECHA InfoCard 100.003.302 Edit this at Wikidata
EC Number
  • 203-631-1
KEGG
  • C00414 checkY
PubChem CID
  • 7967
UNII
  • 5QOR3YM052 checkY
CompTox Dashboard (EPA)
  • DTXSID6020359 Edit this at Wikidata
InChI
  • InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 checkY
    Key: JHIVVAPYMSGYDF-UHFFFAOYSA-N checkY
  • InChI=1/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
    Key: JHIVVAPYMSGYDF-UHFFFAOYAY
SMILES
  • C1CCC(=O)CC1
Properties
Chemical formula
 C6H10O
Molar mass 98.15 g/mol
Appearance Colorless liquid[3]
Odor peppermint or acetone-like
Density 0.9478 g/mL, liquid
Melting point −47 °C (−53 °F; 226 K)[6]
Boiling point 155.65 °C (312.17 °F; 428.80 K)
Solubility in water
 8.6 g/100 mL (20 °C)
Solubility in all organic solvents Miscible
log P 0.81
Vapor pressure 5 mmHg (20°C)[4]
Magnetic susceptibility (χ)
 -62.04·10−6 cm3/mol
Refractive index (nD)
 1.447
Viscosity 2.02 cP at 25 °C[5]
Thermochemistry
Std molar
entropy (S⦵298)
 +229.03 J.K−1.mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −270.7 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −3519.3 kJmol−1
Hazards
GHS labelling:
Pictograms
 GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
Signal word
 Danger[7]
Hazard statements
 H226, H302, H305, H312, H315, H318, H332[7]
Precautionary statements
 P280, P305+P351+P338[7]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 44 °C (111 °F; 317 K)
Autoignition
temperature
 420 °C (788 °F; 693 K)
Explosive limits 1.1–9.4%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally)[8]
LC50 (median concentration)
 8000 ppm (rat, 4 hr)[9]
LCLo (lowest published)
 4706 ppm (mouse, 1.5 hr)[9]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 50 ppm (200 mg/m3)[4]
REL (Recommended)
 TWA 25 ppm (100 mg/m3) [skin][4]
IDLH (Immediate danger)
 700 ppm[4]
Related compounds
Related ketones
 Cyclopentanone, cycloheptanone
Related compounds
 Cyclohexanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid[3] has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color.[10] Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.[11]

  1. ^ "ICSC 0425 – CYCLOHEXANONE". inchem.org. Retrieved 2022-08-24.
  2. ^ "CDC – NIOSH Pocket Guide to Chemical Hazards – Cyclohexanone". Centers for Disease Control and Prevention (CDC). Retrieved August 24, 2022.
  3. ^ a b "Cyclohexanone (CID 7967)". PubChem.
  4. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0166". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Ch. Wohlfarth. "Viscosity of cyclohexanone". In M.D. Lechner (ed.). Viscosity of Pure Organic Liquids and Binary Liquid Mixtures · Supplement to IV/18. Springer-Verlag. doi:10.1007/978-3-540-75486-2_192.
  6. ^ "Cyclohexanone". Sigma-Aldrich.
  7. ^ a b c Sigma-Aldrich Co., Cyclohexanone.
  8. ^ Cyclohexanone: toxicity for animals and humans
  9. ^ a b "Cyclohexanone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  10. ^ "Cyclohexanone (CID 7967)". PubChem.
  11. ^ Musser, Michael T. (October 15, 2011). "Cyclohexanol and Cyclohexanone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KgaA. doi:10.1002/14356007.a08_217.pub2. ISBN 978-3-527-30673-2. OCLC 46878292. Retrieved January 27, 2009.

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Cyclohexanone

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Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This...

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Cyclohexanone oxime

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Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production...

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Cyclohexanone dehydrogenase

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enzymology, a cyclohexanone dehydrogenase (EC 1.3.99.14) is an enzyme that catalyzes a redox chemical reaction of the form cyclohexanone + acceptor ⇌ {\displaystyle...

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Cyclohexanone monooxygenase

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Cyclohexanone monooxygenase (EC 1.14.13.22, cyclohexanone 1,2-monooxygenase, cyclohexanone oxygenase, cyclohexanone:NADPH:oxygen oxidoreductase (6-hydroxylating...

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Caprolactam

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caprolactam. It was estimated that 90% of all caprolactam is synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime...

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Cyclohexane

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cyclohexane undergoes catalytic oxidation to produce cyclohexanone and cyclohexanol. The cyclohexanone–cyclohexanol mixture, called "KA oil", is a raw material...

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Phenol

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alkenes, and ketones. Thus, adamantyl-1-bromide, dicyclopentadiene), and cyclohexanones give respectively 4-adamantylphenol, a bis(2-hydroxyphenyl) derivative...

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Ketone

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for cyclopropanone ((CH2)2CO) to the tens. Larger derivatives exist. Cyclohexanone ((CH2)5CO), a symmetrical cyclic ketone, is an important intermediate...

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Cyclohexanol

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the formation of cyclohexanone. Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted...

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Caraway

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γ‑terpinene, trimethylene dichloride, β-pinene, 2-(1-cyclohexenyl), cyclohexanone, β-phellandrene, 3-carene, α-thujene, and linalool. Wikibooks Cookbook...

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Cyclohexene

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to both phenol and cyclohexanone. Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam...

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Hydroperoxide

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industry. For example, the cobalt catalyzed oxidation of cyclohexane to cyclohexanone: C6H12 + O2 → (CH2)5C=O + H2O Drying oils, as found in many paints and...

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Adipic acid

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known as adipates. Adipic acid is produced by oxidation of a mixture of cyclohexanone and cyclohexanol, which is called KA oil, an abbreviation of ketone-alcohol...

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Methylenecyclohexane

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produced by a Wittig reaction or a reaction with a Tebbe's reagent from cyclohexanone. It can also be synthesized as a side product of the dehydration of...

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Methylcyclohexanone

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3-methylcyclohexanone, and 4-methylcyclohexanone. They can be viewed as derivative of cyclohexanone. They can be prepared by oxidation of methylcyclohexane as well as partial...

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Cumene process

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cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone. Cyclohexanone is an important precursor to some nylons. Starting with the alkylation...

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Nitrous oxide

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degradation of the nitrolic acid intermediate derived from the nitration of cyclohexanone. Natural processes that generate nitrous oxide may be classified as...

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Flammability limit

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Book Published by McGraw-Hill Professional, 2001 pg. 216 "ICSC 0425 - CYCLOHEXANONE". www.inchem.org. Retrieved 18 March 2018. "MSDS Cyclopentadiene". ox...

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Nitroxyl

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which then further decompose. HNO is generated via organic oxidation of cyclohexanone oxime with lead tetraacetate to form 1-nitrosocyclohexyl acetate: This...

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Nitric acid

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is produced on a large scale by oxidation of "KA oil"—a mixture of cyclohexanone and cyclohexanol—with nitric acid. Nitric acid has been used in various...

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Bisphenol Z

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polycarbonate plastics. It is prepared by the condensation on phenol and cyclohexanone: Clinofibrate Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto;...

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Acetone

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Determination of the Equilibrium Constants for Keto-Enol Tautomerism for Cyclohexanone and Acetone". Bulletin of the Chemical Society of Japan. 49 (11): 3089–3092...

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Polystyrene

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carbon disulfide, chlorinated aliphatic hydrocarbons, chloroform, cyclohexanone, dioxane, ethyl acetate, ethylbenzene, MEK, NMP, THF Thermal conductivity...

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Solvent

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Solvent R-12 toluene 60%, butyl acetate 30%, xylene 10%. Solvent R-14 cyclohexanone 50%, toluene 50%. Solvent R-24 solvent 50%, xylene 35%, acetone 15%...

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Solvent bonding

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Acetone Cyclohexane Methyl ethyl ketone (MEK) Tetrahydrofuran Polyester Cyclohexanone Polybutadiene Benzene Cyclohexane Hexane Toluene Polysulfone Methylene...

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Hydroxylamine

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reaction) Approximately 95% of hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6. The treatment of this oxime with acid...

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