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Title: Cyclohexanol  
Author: World Heritage Encyclopedia
Language: English
Subject: Cycloalkanols, Elimination reaction, Thermoresponsive polymers in chromatography, Homosalate, Hexanol
Collection: Cycloalkanols, Cyclohexanols
Publisher: World Heritage Encyclopedia


Skeletal formula of cyclohexanol
Ball-and-stick model of the cyclohexanol molecule
IUPAC name
Other names
Cyclohexyl Alcohol,
ChemSpider  Y
DrugBank  Y
EC number 203-630-6
Jmol-3D images Image
RTECS number GV7875000
Molar mass 100.158 g/mol
Appearance Colorless, viscous liquid.
Odor camphor-like
Density 0.9624 g/mL, liquid
Melting point 25.93 °C (78.67 °F; 299.08 K)
Boiling point 161.84 °C (323.31 °F; 434.99 K)
3.60 g/100 mL (20 °C)
4.3 g/100 mL (30 °C)
Solubility soluble in ethanol, ethyl ether acetone, chloroform
miscible with ethyl acetate, linseed oil, benzene
Vapor pressure 1 mmHg (20°C)[2]
4.40 x 10−6 atm-cu m/mol
Acidity (pKa) 16
Viscosity 41.07 mPa·s (30 °C)
Main hazards Flammable, skin irritant
Reacts violently with oxidizing agents
Safety data sheet MSDS for cyclohexanol
R-phrases R20 R22 R37 R38
S-phrases S24 S25
NFPA 704
Flash point 67 °C (153 °F; 340 K)
300 °C (572 °F; 573 K)
Explosive limits 2.7-12%
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
2060 mg/kg (oral, rat)
2200-2600 mg/kg (oral, rabbit)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 50 ppm (200 mg/m3)[2]
REL (Recommended)
TWA 50 ppm (200 mg/m3)[2]
400 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Cyclohexanol is the formula (CH2)5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxyl group.[4] This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.[5]


  • Production 1
  • Basic reactions 2
  • Structure 3
  • Applications 4
  • Safety 5
  • References 6


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

C6H12 + 1/2 O2 → C6H11OH

This process co-forms cyclohexanone, and this mixture ("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. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol:

C6H5OH + 3 H2 → C6H11OH

This process can also be adjusted to favor the formation of cyclohexanone.

Basic reactions

Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted on a large scale in industry to the oxime, a precursor to caprolactam. As a laboratory exercise, this oxidation can be effected with chromic acid. Esterification affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used as plasticizers. Heating in the presence of acid catalysts converts cyclohexanol to cyclohexene.[5]


Cyclohexanol has at least two solid phases. One of them is a plastic crystal.


As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor to nylons, but also to various plasticizers. Small amounts are used as a solvent.


Cyclohexanol is somewhat toxic: the TLV for the vapor for 8 h is 50 ppm.[5] The IDLH concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals.[6] Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.[7]


  1. ^ Merck Index, 11th Edition, 2731.
  2. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0165".  
  3. ^ "Cyclohexanol". Immediately Dangerous to Life and Health.  
  4. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press.  
  5. ^ a b c d Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  6. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  7. ^ [2] Lucrecia Márquez-Rosado, Cristina Trejo-Solís 2, María del Pilar Cabrales-Romero, Evelia Arce-Popoca, Adolfo Sierra-Santoyo, Leticia Alemán-Lazarini, Samia Fatel-Fazenda, Claudia E. Carrasco-Legleu, Saúl Villa-Treviño, "Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model", Molecular Carcinogenesis, Vol. 46, No. 7, Pages 524 - 533, March 2007.
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