1,4-Cyclohexanedimethanol diglycidyl ether

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]

1,4-Cyclohexanedimethanol diglycidyl ether

Names
IUPAC name 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]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
CAS Number	14228-73-0
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3184513
ChemSpider	55618
ECHA InfoCard	100.034.620
EC Number	238-098-4
PubChem CID	61718
CompTox Dashboard (EPA)	DTXSID1044805
InChI 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
SMILES C1CC(CCC1COCC2CO2)COCC3CO3
Properties
Chemical formula	C14H24O4
Molar mass	256.342 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H412
Precautionary statements	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). Infobox references

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]

Toxicology

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

See also

• Glycidol