1,4-Cyclohexanedimethanol diglycidyl ether
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
2,2â²-[Cyclohexane-1,4-diylbis(methyleneoxymethylene)]bis(oxirane) | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.034.620 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C14H24O4 | |
| Molar mass | 256.342 g·molâ1 |
| Hazards | |
| GHS labelling:[1] | |
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| 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).
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Synonyms
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
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
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]