1,4-Cyclohexanedimethanol diglycidyl ether

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1,4-Cyclohexanedimethanol diglycidyl ether
File:1,4-Cyclohexanedimethanol diglycidyl ether.svg
Names
Preferred IUPAC name
2,2′-[Cyclohexane-1,4-diylbis(methyleneoxymethylene)]bis(oxirane)
Other names
    • 1,4-Bis(glycidyloxymethyl)cyclohexane
    • 1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane
    • 2,2'-(1,4-Cyclohexanediylbis(methyleneoxymethylene))bis-oxirane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 238-098-4
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C14H24O4/c1-2-12(6-16-8-14-10-18-14)4-3-11(1)5-15-7-13-9-17-13/h11-14H,1-10H2
    Key: VQMQXWYQIIUJIT-UHFFFAOYSA-N
  • C1CC(CCC1COCC2CO2)COCC3CO3
Properties
C14H24O4
Molar mass 256.342 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317, H319, H412
P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P313, P337+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family.[2] Its formula is C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane. It has the CAS number of 14228-73-0[3] and is REACH registered in Europe.[4] An industrial chemical, a key use is in the reduction of the viscosity of epoxy resin systems functioning as a reactive diluent.[5][6]

Synonyms

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The material is known under various names which include:[7]

  • 2,2'-[1,4-Cyclohexanediylbis(methyleneoxymethylene)]bis[oxirane]
  • 1,4-Bis(glycidoxymethyl)cyclohexane
  • 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether
  • 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane
  • 1,4-Bis[(glycidyloxy)methyl]cyclohexane
  • 1,4-Cyclohexanedimethanol diglycidyl Ether

Manufacture

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The manufacturing process involves reacting cyclohexanedimethanol with epichlorohydrin, using a Lewis acid as catalyst, to form a halohydrin. This is followed by washing with sodium hydroxide in a dehydrochlorination step to form the epoxide rings.[8] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

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As the molecule has oxirane functionality, a key use is reducing the viscosity of epoxy resins.[9] These reactive diluent modified epoxy resins may then be further formulated into which may then be formulated into CASE applications: Coatings,[10] Adhesives, Sealants,[11] Elastomers, and electronic encapsulant.[12] The use of the diluent does affect mechanical properties and microstructure of epoxy resins.[13][14]

It is also used as a monomer in UV curing systems.[15] In addition it is used to synthesize other molecules such as the acrylated version.[16]

Toxicology

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The material is classed as a skin irritant.[17][18]

See also

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References

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  5. ^ EP 2621994, Hefner, Robert E., "Epoxy resin compositions", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Dow Global Technologies LLC 
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  10. ^ WO application 2015095994, Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Dow Global Technologies LLC 
  11. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  12. ^ JP 4965715, Hosono, Yohei & Homma, Hiroki, "Epoxy resin composition and semiconductor sealing material using the same", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Namics Corp. 
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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Further reading

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  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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