Cyclohexanone

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Cyclohexanone[1][2]
Skeletal formula of cyclohexanone Ball-and-stick model of cyclohexanone
Skeletal formula viewed side-on, showing the non-planar conformation
Identifiers
CAS number 108-94-1 YesY
PubChem 7967
ChemSpider 7679 YesY
UNII 5QOR3YM052 YesY
DrugBank DB02060
KEGG C00414 YesY
ChEBI CHEBI:17854 YesY
ChEMBL CHEMBL18850 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H10O
Molar mass 98.15 g/mol
Appearance Colorless liquid
Odor peppermint or acetone-like
Density 0.9478 g/mL, liquid
Melting point −47 °C (−53 °F; 226 K)[4]
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
Refractive index (nD) 1.447
Viscosity 2.02 cP at 25 °C[3]
Thermochemistry
Std molar
entropy
So298
+229.03 J.K−1.mol−1
Std enthalpy of
formation
ΔfHo298
−270.7 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−3519.3 kJmol−1
Hazards
EU classification Harmful (Xn)
R-phrases R10, R20
S-phrases (S2), S25
NFPA 704
Flammability code 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 fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 44 °C (111 °F; 317 K)
Autoignition temperature 420 °C (788 °F; 693 K)
Explosive limits 1.1-9.4%
Related compounds
Related ketones Cyclopentanone, cycloheptanone
Related compounds Cyclohexanol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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 oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble in water, but miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.[5]

Production[edit]

Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:[5]

C6H12 + O2 → (CH2)5CO + H2O

This process co-forms cyclohexanol, 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 intermediacy of the hydroperoxide C6H11O2H. 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.[5]

Laboratory methods[edit]

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.[6]

Uses[edit]

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 the oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:[5]

Caprolactam Synth.png

Safety[edit]

Like cyclohexanol, cyclohexanone is not carcinogenic and is only moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant.[5]

A recent study of plastic tubing used in medical procedures that circulate blood outside the body suggests a link between this compound and decreased heart function, swelling, loss of taste and short term memory loss.[7]

References[edit]

  1. ^ International Chemical Safety Card 0425
  2. ^ NIOSH Pocket Guide to Chemical Hazards
  3. ^ Data extract from Landolt-Börnstein IV/25: Viscosity of Pure Organic Liquids and Binary Liquid Mixtures
  4. ^ Sigma-Aldrich - Cyclohexanone
  5. ^ a b c d e Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217
  6. ^ http://www2.volstate.edu/CHEM/2010/Labs/Cyclohexanone.html
  7. ^ http://www.eurekalert.org/pub_releases/2009-05/jhmi-cfi043009.php