Cyclohexanol

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Structural formula
Structural formula of cyclohexanol
General
Surname Cyclohexanol
other names
  • Cyclohexyl alcohol
  • Anol
  • Hydraline
  • Sextole
  • Adronal
Molecular formula C 6 H 12 O
Brief description

colorless, crystalline powder with a camphor-like odor

External identifiers / databases
CAS number 108-93-0
EC number 203-630-6
ECHA InfoCard 100.003.301
PubChem 7966
ChemSpider 7678
DrugBank DB03703
Wikidata Q423282
properties
Molar mass 100.16 g mol −1
Physical state

firmly

density

0.95 g cm −3

Melting point

24 ° C

boiling point

161 ° C

Vapor pressure

1.3 h Pa (30 ° C)

solubility

moderate in water (40 g l −1 at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning

Caution

H and P phrases H: 302 + 332-315-335
P: 261
MAK
  • DFG : not specified
  • Switzerland: 50 ml m −3 or 200 mg m −3
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyclohexanol is a secondary alcohol that is derived from cyclohexane . It has the molecular formula C 6 H 12 O.

Extraction and presentation

Cyclohexanol is obtained together with cyclohexanone in the catalytic oxidation of cyclohexane with atmospheric oxygen. This radical reaction takes place via an unstable intermediate product, cyclohexane hydroperoxide, which breaks down spontaneously into the two products. The product mixture can be separated by distillation.

Synthesis of cyclohexanol from cyclohexane

Alternatively, cyclohexanol can be obtained by catalytic hydrogenation of phenol :

Synthesis of cyclohexanol from phenol

properties

Cyclohexanol melts at 24 ° C and boils at 161 ° C. Cyclohexanol dissolves well in ethanol . In water dissolve at 20 ° C, 56.7 g cyclohexanol per liter. The colorless crystals smell like camphor . The flash point is 68 ° C, the ignition temperature 290 ° C. With a density of 0.95 g / cm 3 , it is lighter than water. Cyclohexanol is slightly viscous at room temperature, but mostly frozen.

Reactions

Cyclohexanol reacts with elemental chlorine in sunlight to form tetrachlorocyclohexanone. This can be converted to tetrachlorocyclohexanol with aluminum triisopropoxide , an example of the Meerwein-Ponndorf-Verley reduction . 2,6-dichlorophenol is obtained by heating .

use

Extraction and solvents for the production of paints and plastics, intermediate product for chemical syntheses, standard reference substance in gas chromatography . Up until the 1980s, it was also used as an evaporating liquid for heat cost allocators .

safety instructions

Cyclohexanol is harmful and slightly hazardous to water.

Individual evidence

  1. ↑ a b c d e f g h i j Entry on cyclohexanol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ Entry on cyclohexanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  3. ↑ The MAK Collection for Occupational Health and Safety: Cyclohexanol , 2010 (PDF), doi : 10.1002 / 3527600418.mb10893d0048 .
  4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 108-93-0 or cyclohexanol ), accessed on November 2, 2015.
  5. ^ O. Hassel, K. Lunde: Tetrachloro-Cyclohexanone and Tetrachloro-Cyclohexanol Obtained from Cyclohexanol. In: Acta Chem. Scand. 1950 , 4 , pp. 200-204, doi : 10.3891 / acta.chem.scand.04-0200 .

Web link

Wiktionary: Cyclohexanol  - explanations of meanings, word origins, synonyms, translations