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.

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Cyclohexanedimethanol

Names
IUPAC name [4-(hydroxymethyl)cyclohexyl]methanol
Preferred IUPAC name (cyclohexane-1,4-diyl)dimethanol
Other names 1,4–Cyclohexanedimethanol; CHDM; 1,4-Bis(hydroxymethyl)cyclohexane
Identifiers
CAS Number	105-08-8 Y
3D model (JSmol)	Interactive image
ChemSpider	7449 N
ECHA InfoCard	100.002.972
PubChem CID	7735
UNII	8C3FKR6R1B N
CompTox Dashboard (EPA)	DTXSID9026712
InChI InChI=1S/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2 N Key: YIMQCDZDWXUDCA-UHFFFAOYSA-N N InChI=1/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2 Key: YIMQCDZDWXUDCA-UHFFFAOYAS
SMILES C1CC(CCC1CO)CO
Properties
Chemical formula	C8H16O2
Molar mass	144.21 g/mol
Appearance	White waxy solid
Density	1.02 g/ml
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). N verify (what is YN ?) Infobox references

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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.^[1] The cis/trans ratio of the CHDM is affected by the catalyst.^[2]

Byproduct of this process are 4-methylcyclohexanemethanol (CH₃C₆H₁₀CH₂OH) and the monoester methyl 4-methyl-4-cyclohexanecarboxylate (CH₃C₆H₁₀CO₂CH₃, CAS registry number 51181-40-9).^[3] The leading producers in CHDM are Eastman Chemical in US and SK Chemicals in South Korea.

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.^[4][5] In addition it maybe spun to form carpet fibers.^[6]

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.^[7] 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 a raw material for the production of 1,4-cyclohexanedimethanol diglycidyl ether, an epoxy diluent.^[8] The key use for this diglycidyl ether is to reduce the viscosity of epoxy resins.^[9]