Cyclohexanone

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Cyclohexanone[1][2]
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Names
Preferred IUPAC name
Cyclohexanone
Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
Identifiers
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3D model (JSmol)
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  • 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
  • C1CCC(=O)CC1
Properties
C6H10O
Molar mass 98.145 g·mol−1
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)
8.6 g/100 mL (20 °C)
Solubility in all organic solvents Miscible
log P 0.81
Vapor pressure 5 mmHg (20 °C)[4]
−62.04·10−6 cm3/mol
1.447
Viscosity 2.02 cP at 25 °C[5]
Thermochemistry
+229.03 J·K−1·mol−1
−270.7 kJ·mol−1
−3519.3 kJ·mol−1
Hazards
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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)
420 °C (788 °F; 693 K)
Explosive limits 1.1–9.4%
Lethal dose or concentration (LD, LC):
1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally)[8]
8000 ppm (rat, 4 hr)[9]
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).
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Template:Chembox Footer/trackingTemplate:Short description

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]

History and synthesis

The compound was discovered by Edmund Drechsel [de] in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol. He named it hydrophenoketone and correctly suggested that phenol was first hydrogenated by electrolytic hydrogen to cyclohexanol, which he wasn't able to isolate, and then oxidized by electrolytic oxygen.[12][13]

Laboratory synthesis

Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide (Jones oxidation). An alternative method utilizes the safer and more readily available oxidant sodium hypochlorite.[14][15]

Industrial production

Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:[11]

C6H12 + O2 → (CH2)5CO + H2O

This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. The oxidation involves radicals and the hydroperoxide C6H11O2H as an intermediate. In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol:

C6H5OH + 2 H2 → (CH2)5CO

This process can also be adjusted to favor the formation of cyclohexanol.[11]

ExxonMobil developed a process in which benzene is hydroalkylated to cyclohexylbenzene. This latter product is oxidized to a hydroperoxide and then cleaved into phenol and cyclohexanone.[16] Therefore, this newer process without producing the acetone by-product appears attractive and is similar to the cumene process as a hydroperoxide is formed and then decomposed to yield two key products.[17]

Uses

The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to cyclohexanone oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:[11]

Other reactions

In addition to the large scale reactions conducted in service of the polymer industry, many reactions have been developed for cyclohexanone.

In the presence of light, it undergoes alpha-chlorination to give 2-chlorocyclohexanone.[18] It forms a trimethylsilylenol ether upon treatment with trimethylsilylchloride in the presence of base.[19]

It forms an enamine with pyrrolidine.[20]

Self condensation of cyclohexanone gives cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.[21]

Treatment with nitrosyl chloride and ethanol in sulfur dioxide gives the oximinecarboxylic ester:[22]

Page Module:Chem2/styles.css has no content.(CH2)5CO + C2H5OH + NOCl → HON=CH(CH2)4CO2C2H5 + HCl

Illicit use

Cyclohexanone has been used in the illicit production of phencyclidine and its analogs[23] and is often subject to purchase restrictions, such as being listed on the Special Surveillance List in the US.[24]

Safety

Like cyclohexanol, cyclohexanone is not carcinogenic and is moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant.[11]

References

  1. ^ Page Module:Citation/CS1/styles.css has no content."ICSC 0425 – CYCLOHEXANONE". inchem.org. Retrieved 2022-08-24.
  2. ^ Page Module:Citation/CS1/styles.css has no content."CDC – NIOSH Pocket Guide to Chemical Hazards – Cyclohexanone". Centers for Disease Control and Prevention (CDC). Retrieved August 24, 2022.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content."Cyclohexanone (CID 7967)". PubChem.
  4. ^ a b c d Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0166". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Page Module:Citation/CS1/styles.css has no content.Ch. Wohlfarth (2008). "Viscosity of cyclohexanone". In M.D. Lechner (ed.). Viscosity of Pure Organic Liquids and Binary Liquid Mixtures · Supplement to IV/18. Landolt-Börnstein - Group IV Physical Chemistry. Vol. 25. Springer-Verlag. p. 371. doi:10.1007/978-3-540-75486-2_192. ISBN 978-3-540-56050-0.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Cyclohexanone". Sigma-Aldrich.
  7. ^ a b c Sigma-Aldrich Co., Cyclohexanone.
  8. ^ Cyclohexanone: toxicity for animals and humans
  9. ^ a b Page Module:Citation/CS1/styles.css has no content."Cyclohexanone". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  10. ^ Page Module:Citation/CS1/styles.css has no content."Cyclohexanone (CID 7967)". PubChem.
  11. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.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.
  12. ^ Template:Cite Q
  13. ^ Page Module:Citation/CS1/styles.css has no content.Perkin, William Henry; Plant, Sydney Glenn Preston (1921). "Derivatives of tetrahydrocarbazole". Journal of the Chemical Society, Transactions. 119: 1825–1839. doi:10.1039/CT9211901825. ISSN 0368-1645.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Oxidation of Cyclohexanol to Cyclohexanone". Archived from the original on 2012-04-26. Retrieved 2012-07-09.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G. (June 1985). "The design of laboratory experiments in the 1980's: A case study on the oxidation of alcohols with household bleach". Journal of Chemical Education. 62 (6): 519. Bibcode:1985JChEd..62..519M. doi:10.1021/ed062p519.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2019-10-27.
  17. ^ Page Module:Citation/CS1/styles.css has no content."Phenol – The essential chemical industry online". 2017-01-11. Retrieved 2019-10-27.
  18. ^ Page Module:Citation/CS1/styles.css has no content.M. S. Newman; M. D. Farbman; H. Hipsher (1945). "2-chlorocyclohexanone". Org. Synth. 25: 22. doi:10.15227/orgsyn.025.0022.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Valsamma Varghese; Manasi Saha; Kenneth M. Nicholas (1989). "Alkylations Using Hexacarbonyl(Propargylium)dicobalt Salts: 2-(1-methyl-2-propynyl)cyclohexanone". Org. Synth. 67: 141. doi:10.15227/orgsyn.067.0141.
  20. ^ Page Module:Citation/CS1/styles.css has no content.R. B. Woodward; I. J. Pachter; M. L. Scheinbaum (1974). "2,2-(Trimethylenedithio)cyclohexanone". Org. Synth. 54: 39. doi:10.15227/orgsyn.054.0039.
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  22. ^ Script error: No such module "Template wrapper".
  23. ^ Page Module:Citation/CS1/styles.css has no content.Shulgin, A. T.; MacLean, D. E. (25 September 2008). "Illicit Synthesis of Phencyclidine (PCP) and Several of Its Analogs". Clinical Toxicology. 9 (4): 553–560. doi:10.3109/15563657608988157. PMID 975751.
  24. ^ Page Module:Citation/CS1/styles.css has no content."Special Surveillance List of Chemicals, Products, Materials and Equipment Used in the Clandestine Production of Controlled Substances or Listed Chemicals". Archived from the original on April 20, 2011.

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