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Triglycidylglycerol

Identifiers
CAS Number	13236-02-7
3D model (JSmol)	Interactive image
ChemSpider	24031
ECHA InfoCard	100.032.905
EC Number	236-211-1
PubChem CID	25795
UNII	0KVT2Q7Z17
CompTox Dashboard (EPA)	DTXSID00884584
InChI InChI=1S/C12H20O6/c1(13-3-10-5-16-10)9(15-7-12-8-18-12)2-14-4-11-6-17-11/h9-12H,1-8H2Key: SYEWHONLFGZGLK-UHFFFAOYSA-N
SMILES C1C(O1)COCC(COCC2CO2)OCC3CO3
Properties
Chemical formula	C₁₂H₂₀O₆
Molar mass	260.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Glycerol triglycidyl ether (triglycidyl glycerol) is an aliphatic organic chemical in the glycidyl ether family. It has the formula C₁₂H₂₀O₆. The CAS number is 13236-02-7. The IUPAC name is 2-oxirane. A key use is as a modifier for epoxy resins as a reactive diluent.

Alternative names

There are a variety of recognized alternate names.

• TRIGLYCIDYLGLYCEROL
• 1,2,3-Tris(2,3-epoxypropoxy)propane
• Glycerine triglycidyl ether
• Glycerol tris(2,3-epoxypropyl) ether
• 2-oxirane
• Propane, 1,2,3-tris(2,3-epoxypropoxy)-
• Glycerol 1,2,3-triglycidyl ether

Manufacture

Glycerine 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.

Uses

As the molecule has 3 oxirane functionalities, it is a reactive modifier and viscosity reduction agent of epoxy resins. 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. Its use in photochemical applications has also been extensively used and studied. Uses in modern battery technology have also been researched. The molecule maybe further reacted to produce materials such as surfactants.

Further reading

• 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 ( ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.

References

1. PubChem. "Triglycidylglycerol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-12-17.
2. "Glycerol triglycidyl ether | 13236-02-7". ChemicalBook. Retrieved 2024-12-17.
3. Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
4. "Glycerol triglycidyl ether | 13236-02-7 | FG173064". www.biosynth.com. Retrieved 2024-12-17.
5. "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.
6. Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry. 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN 0887-624X.
7. US 5162547, Roth, Martin; Wolleb, Heinz & Truffer, Marc-Andre, "Process for the preparation of glycidyl ethers", published 1992-11-10, assigned to Ciba-Geigy Corp. 
8. Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, vol. 1, Dordrecht: Springer Netherlands, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, archived from the original on 2022-04-11, retrieved 2022-03-29
9. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" Master of Science Thesis April 1997 Imperial College London
10. Huang, Biwu; Chen, Yiwang; Deng, Qilan (2008-12-01). "Photopolymerization of glycerin triglycidyl ether based systems". Journal of Wuhan University of Technology-Mater. Sci. Ed. 23 (6): 795–798. doi:10.1007/s11595-007-6795-2. ISSN 1993-0437.
11. Crivello, James V.; Ortiz, Ricardo Acosta (2001). "Synthesis of epoxy monomers that undergo synergistic photopolymerization by a radical-induced cationic mechanism". Journal of Polymer Science Part A: Polymer Chemistry. 39 (20): 3578–3592. doi:10.1002/pola.10015. ISSN 1099-0518.
12. Huang, Hao; Yi, Linyun; Chen, Xiaoxiao; Wei, Chaohui; Zhou, Aijun; Wang, Yuehui; Li, Jingze (2024). "A glycerol triglycidyl ether cross-linker assisting an in situ thermally polymerized gel polymer electrolyte for advanced lithium metal batteries". New Journal of Chemistry. 48 (30): 13631–13638. doi:10.1039/D4NJ01484G. ISSN 1144-0546.
13. Zhou, Ming; Zhao, Jinzhou; Wang, Xu; Jing, Jiaqiang; Zhou, Lizhi (2013). "Synthesis and Characterization of Novel Surfactants 1,2,3-tri(2-oxypropylsulfonate-3-alkylether-propoxy) Propanes". Journal of Surfactants and Detergents. 16 (5): 665–672. doi:10.1007/s11743-013-1442-8. ISSN 1558-9293.

• Reactive diluents
• Glycidyl ethers