1,4–Cyclohexanedimethanol; CHDM; 1,4-Bis(hydroxymethyl)cyclohexane
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||144.21 g/mol|
|Appearance||White waxy solid|
|Melting point||41 to 61 °C (106 to 142 °F; 314 to 334 K)|
|Boiling point||284 to 288 °C (543 to 550 °F; 557 to 561 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
Via the process called polycondensation, CHDM is a precursor to polyesters. It is one of the most important comonomers for production of polyethylene terephthalate (PET), or polyethylene terephthalic ester (PETE), from which plastic bottles are made.
Thermoplastic polyesters containing CHDM exhibit enhanced strength, clarity, and solvent resistance. The properties of the polyesters vary from the high melting crystalline poly(1,4-cyclohexylenedimethylene terephthalate), PCT, to the non-crystalline copolyesters derived from both ethylene glycol and CHDM. The properties of these polyesters also is affected by the cis/trans ratio of the CHDM monomer. CHDM reduces the degree of crystallinity of PET homopolymer, improving its processability. The copolymer tends to resist degradation, e.g. to acetaldehyde. The copolymer with PET is known as glycol-modified polyethylene terephthalate, PETG. PETG is used in many fields, including electronics, automobiles, barrier, and medical, etc.
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
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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