Английская Википедия:Cyclohexanedimethanol
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.[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.
Applications
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]
References
External links
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen and Juha Lehtonen "Alcohols, Polyhydric" Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. Шаблон:Doi
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Citation
