Cyclohexanedimethanol

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title: "Cyclohexanedimethanol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["monomers", "diols"] topic_path: "general/monomers" source: "https://en.wikipedia.org/wiki/Cyclohexanedimethanol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443929860 | ImageFile = CHDMisomers.png | IUPACName = [4-(hydroxymethyl)cyclohexyl]methanol | PIN = (cyclohexane-1,4-diyl)dimethanol | OtherNames = 1,4–Cyclohexanedimethanol; CHDM; 1,4-Bis(hydroxymethyl)cyclohexane |Section1={{Chembox Identifiers | CASNo = 105-08-8 | CASNo_Ref = | UNII_Ref = | UNII = 8C3FKR6R1B | PubChem = 7735 | ChemSpiderID_Ref = | ChemSpiderID = 7449 | SMILES = C1CC(CCC1CO)CO | InChI = 1/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2 | InChIKey = YIMQCDZDWXUDCA-UHFFFAOYAS | StdInChI_Ref = | StdInChI = 1S/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2 | StdInChIKey_Ref = | StdInChIKey = YIMQCDZDWXUDCA-UHFFFAOYSA-N}} |Section2={{Chembox Properties | Formula = C8H16O2 | MolarMass = 144.21 g/mol | Appearance = White waxy solid | Density = 1.02 g/ml | MeltingPtC = 41 to 61 | BoilingPtC = 284 to 288 | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

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.{{cite journal | title = Synthesis and Properties of Cyclic Diester Based Aliphatic Copolyesters | author1=S.R. Turner | author2=Y. Li | journal = Journal of Polymer Science Part A: Polymer Chemistry | volume = 48 | pages = 2162–2169 | year = 2010 | issue=10 | url = | doi = 10.1002/pola.23985 | bibcode=2010JPoSA..48.2162L }} The cis/trans ratio of the CHDM is affected by the catalyst.{{cite journal | title = The materials Chemistry of Inorganic Catalyst | author1=J. M. Thomas | author2=R. Raja | journal = Australian Journal of Chemistry | volume = 54 | pages = 551–560 | year = 2002 | url = | doi = 10.1071/CH01150}}

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.

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.{{cite journal | title = Development of amorphous copolyesters based on 1,4- cyclohexane-dimethanol | author = S.R. Turner | journal = Journal of Polymer Science Part A: Polymer Chemistry | volume = 42 | pages = 5847–5852 | year = 2004 | issue = 23 | url = | doi = 10.1002/pola.20460| bibcode = 2004JPoSA..42.5847T | doi-access = free | title = Mini-review The Polyoxaesters |author1=S. Andjelic |author2=D.D. Jamiolkowski |author3=R. Bezwada | journal = Polymer International | volume = 56 | pages = 1063–1077 | year = 2007 | url = | doi = 10.1002/pi.2257}} In addition it maybe spun to form carpet fibers.

:[[File:CHDMester.png|650 px]]

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.{{cite book | title = Encyclopedia of Polymer Science and Technology | author = S. R. Turner | author2 = R.W. Seymour | author3 = T.W. Smith | chapter = Cyclohexanedimethanol Polyesters | pages = | year = 2001 | url = | doi = 10.1002/0471440264.pst257| isbn = 0471440264 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. The key use for this diglycidyl ether is to reduce the viscosity of epoxy resins.

References

References

  1. (2008). "Ullmann's Encyclopedia of Industrial Chemistry".
  2. Hatton. (10 February 2023). "Nylon vs. Polyester Carpet Fibers: Comparison Guide".
  3. Crivello, James V.. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry.
  4. Monte, Salvatore J.. (1998). "Diluents and viscosity modifiers for epoxy resins". Springer Netherlands.

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monomersdiols