Glycerol triglycidyl ether

Glycerol triglycidyl ether
Names
Other names
Triglycidylglycerol; triglycidyl glycerol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.905 Edit this at Wikidata
EC Number
  • 236-211-1
UNII
  • 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,1-8H2
    Key: SYEWHONLFGZGLK-UHFFFAOYSA-N
  • C1C(O1)COCC(COCC2CO2)OCC3CO3
Properties
C12H20O6
Molar mass 260.286 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycerol triglycidyl ether (triglycidyl glycerol) is an aliphatic organic chemical in the glycidyl ether family.[1] It has the formula C12H20O6.[2] The CAS number is 13236–02–7. The IUPAC name is 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane. A key use is as a modifier for epoxy resins as a reactive diluent.[3]

Alternative names

There are a variety of recognized alternate names.[4]

  • Triglycidylglycerol
  • 1,2,3-Tris(2,3-epoxypropoxy)propane
  • Glycerine triglycidyl ether
  • Glycerol tris(2,3-epoxypropyl) ether
  • 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]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.[5][6]

Uses

As the molecule has 3 oxirane functionalities, it is a reactive modifier and viscosity reduction agent of epoxy resins.[7] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings, Adhesives, Sealants, and Elastomers.[8] 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.[9][10] Uses in modern battery technology have also been researched.[11] The molecule maybe further reacted to produce materials such as surfactants.[12]

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. ^ 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.
  6. ^ 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. 
  7. ^ 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
  8. ^ 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
  9. ^ 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.
  10. ^ 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. Bibcode:2001JPoSA..39.3578C. doi:10.1002/pola.10015. ISSN 1099-0518.
  11. ^ 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.
  12. ^ 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.

Further reading