Trimethylolethane triglycidyl ether

Trimethylolethane triglycidyl ether

Names
IUPAC name 2-({2-Methyl-3-(2-oxiranylmethoxy)-2-[(2-oxiranylmethoxy)methyl]propoxy}methyl)oxirane
Identifiers
CAS Number	36366-26-4
3D model (JSmol)	Interactive image
ChemSpider	2666788
ECHA InfoCard	100.214.877
CompTox Dashboard (EPA)	DTXSID50889403
InChI InChI=1S/C14H24O6/c1-14(8-15-2-11-5-18-11,9-16-3-12-6-19-12)10-17-4-13-7-20-13/h11-13H,2-10H2,1H3 Key: YIEBXCCPOCRXRB-UHFFFAOYSA-N
SMILES CC(COCC1CO1)(COCC2CO2)COCC3CO3
Properties
Chemical formula	C14H24O6
Molar mass	288.340 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trimethylolethane triglycidyl ether (TMETGE) is an organic chemical in the glycidyl ether family. It has the formula C₁₄H₂₄O₆ and the IUPAC name is 2-({2-methyl-3-[(oxiran-2-yl)methoxy]-2-{[(oxiran-2-yl)methoxy]methyl}propoxy}methyl)oxirane. The CAS number is 68460-21-9.^{[dubious – discuss][1]} A key use is as a modifier for epoxy resins as a reactive diluent.^[2][3]

^[4]

• Trimethylolethane,chloromethyloxirane polymer
• Trimethylolethane triglycidyl ether
• 1,3-Propanediol,2-(hydroxymethyl)-2-methyl-,polymer with (chloromethyl)oxirane
• 1,3-Propanediol,2-(hydroxymethyl)-2-methyl-,polymer with 2-(chloromethyl)oxirane
• 2-(hydroxymethyl)-2-methylpropane-1,3-diol-2-(chloromethyl)oxirane (1:1)

Trimethylolethane and epichlorohydrin are reacted with a Lewis acid catalyst to form a halohydrin. The next step is dehydrochlorination with sodium hydroxide. This forms the triglycidyl ether. Waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine).^[5][6]

As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins but giving higher functionality.^[7] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings, Adhesives, Sealants, and Elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[8][9] It produces epoxy coatings with high impact resistance^[10] The molecule has been used to synthesize other molecules.^[11][12]

• Epoxide
• Glycidol

• Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.{{cite book}}: CS1 maint: others (link)
• Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.{{cite book}}: CS1 maint: location missing publisher (link)
• Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.
• "Dow Epoxy Resins" (PDF).
• Ash, Michael (2007). Handbook of Fillers, Extenders, and Diluents. Synapse Info Resources. p. 64. ISBN 978-1-890595-96-8.

• Hexion Poly-functional Modifiers
• Denacol epoxy diluent range
• Cargill Reactive diluents
• GE31_Technical Data Sheet