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Names | |
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IUPAC name
[4-(hydroxymethyl)cyclohexyl]methanol
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Preferred IUPAC name
(cyclohexane-1,4-diyl)dimethanol | |
Other names
1,4–Cyclohexanedimethanol; CHDM; 1,4-Bis(hydroxymethyl)cyclohexane
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
ECHA InfoCard | 100.002.972 |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
|
|
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Properties | |
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).
|
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.
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):
In the second step DMCD is further hydrogenated to CHDM:
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]
![]() | |
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 | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.002.972 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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).
|
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.
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):
In the second step DMCD is further hydrogenated to CHDM:
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]