Cyclohexanedimethanol
chemical compound
Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.
Production
CHDM is produced by catalytic hydrogenation of dimethyl terephthalate (DMT). The reaction conducted in two steps beginning with the conversion of DMT to the diester dimethyl 1,4-cyclohexanedicarboxylate (DMCD):
C6H4(CO2CH3)2 + 3 H2 → C6H10(CO2CH3)2
In the second step DMCD is further hydrogenated to CHDM:
C6H10(CO2CH3)2 + 4 H2 → C6H10(CH2OH)2 + 2 CH3OH
A copper chromite catalyst is usually used industrially. The cis/trans ratio of the CHDM is affected by the catalyst.
Byproduct of this process are 4-methylcyclohexanemethanol (CH3C6H10CH2OH) and the monoester methyl
4-methyl-4-cyclohexanecarboxylate (CH3C6H10CO2CH3, CAS registry number 51181-40-9). The leading producers in CHDM are Eastman Chemical in US and SK Chemicals in South Korea.
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