1,4-cyclohexanedimethanol

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Structural formula
Structure of dimethyl terephthalate
Mixture of cis and trans isomers - structural formula without stereochemistry
General
Surname 1,4-cyclohexanedimethanol
other names
  • Cyclohex-1,4-ylene dimethanol
  • 1,4-bis (hydroxymethyl) cyclohexane
  • 1,4-dimethylolcyclohexane
Molecular formula C 8 H 16 O 2
Brief description

colorless solid with a sweetish odor

External identifiers / databases
CAS number
  • 105-08-8
  • 3236-47-3 ( cis )
  • 3236-48-4 ( trans )
PubChem 7735
Wikidata Q1064929
properties
Molar mass 144.21 g mol −1
Physical state

firmly

density

1.04 g cm −3

Melting point

41 ° C

boiling point

286 ° C

Vapor pressure

<0.13 h Pa (30 ° C)

solubility

(slightly) soluble in water (34–143 g · l −1 at 25 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 319
P: 305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,4-Cyclohexanedimethanol (CHDM) is one of the organic compounds from the class of diols . There are two isomeric forms, the cis and the trans isomer.

Manufacturing

1,4-Cyclohexanedimethanol is obtained from dimethyl terephthalate by hydrogenation . The reaction proceeds in two steps, starting with the conversion of dimethyl terephthalate to 1,4-dimethylhexahydroterephthalate (DMHT). In the second step, DMHT is further hydrogenated to CHDM. The cis / trans ratio of CHDM differs depending on the catalyst, from 80:20 for the Cu 4 Ru 12 catalyst, 65:35 for the Ru - Pt catalyst and 88:12 for the Ru - Sn catalyst.

C 6 H 4 (CO 2 CH 3 ) 2 + 3 H 2 → C 6 H 10 (CO 2 CH 3 ) 2
C 6 H 10 (CO 2 CH 3 ) 2 + 4 H 2 → C 6 H 10 (CH 2 OH) 2 + 2 CH 3 OH

use

1,4-Cyclohexanedimethanol is a basic material for the industrial production of polyurethanes and polyesters , such as. B. Polycyclohexylenedimethylene terephthalate (PCT).

Polycondensation of CHDM with dicarboxylic acids

Individual evidence

  1. ↑ a b c d e f g Entry on cyclohex-1,4-ylenedimethanol in the GESTIS substance database of the IFA , accessed on January 16, 2014(JavaScript required) .
  2. ↑ MSDS Eastman
  3. ↑ JM Thomas; R. Raja: The materials Chemistry of Inorganic Catalyst . In: Australian journal of Chemistry . 54, 2002, pp. 551-560. doi : 10.1071 / CH01150 .