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{{Chembox
⚫ Glycerol triglycidyl ether
| Name = Glycerol triglycidyl ether
| ImageFile = Glycerol triglycidyl ether.svg
| OtherNames = Triglycidylglycerol; triglycidyl glycerol
| Section1 = {{Chembox Identifiers
| CASNo = 13236-02-7
| PubChem = 25795
| ChemSpiderID = 24031
| EC_number = 236-211-1
| UNII = 0KVT2Q7Z17
| 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
| InChIKey = SYEWHONLFGZGLK-UHFFFAOYSA-N
| SMILES = C1C(O1)COCC(COCC2CO2)OCC3CO3
}}
| Section2 = {{Chembox Properties
| C = 12 | H = 20 | O = 6
}}
}}

'''Glycerol triglycidyl ether''' (triglycidyl glycerol) is an ] organic chemical in the glycidyl ether family.<ref>{{Cite web |last=PubChem |title=Triglycidylglycerol |url=https://pubchem.ncbi.nlm.nih.gov/compound/Triglycidylglycerol |access-date=2024-12-17 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> It has the formula C<sub>12</sub>H<sub>20</sub>O<sub>6</sub>.<ref>{{Cite web |title=Glycerol triglycidyl ether {{!}} 13236-02-7 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0426574.htm |access-date=2024-12-17 |website=ChemicalBook |language=en}}</ref> The ] is 13236-02-7. The ] name is 2-oxirane. A key use is as a modifier for ] resins as a ].<ref>{{Cite journal |last1=Jagtap |first1=Ameya Rajendra |last2=More |first2=Aarti |date=2022-08-01 |title=Developments in reactive diluents: a review |url=https://doi.org/10.1007/s00289-021-03808-5 |journal=Polymer Bulletin |language=en |volume=79 |issue=8 |pages=5667–5708 |doi=10.1007/s00289-021-03808-5 |s2cid=235678040 |issn=1436-2449}}</ref>

==Alternative names==
There are a variety of recognized alternate names.<ref>{{Cite web |title=Glycerol triglycidyl ether {{!}} 13236-02-7 {{!}} FG173064 |url=https://www.biosynth.com/p/FG173064/13236-02-7-glycerol-triglycidyl-ether#:~:text=2910900090%20-%20China:%202910900090-,Glycerol%20triglycidyl%20ether%20is%20a%20reactive,%20hydrophobic%20compound%20that%20can,to%20yield%20glycerol%20triglycidyl%20ether. |access-date=2024-12-17 |website=www.biosynth.com}}</ref><ref>{{Cite web |title=2-({2,2-Bisbutoxy}methyl)oxirane {{!}} C15H26O6 {{!}} ChemSpider |url=http://www.chemspider.com/Chemical-Structure.93067.html |access-date=2022-04-12 |website=www.chemspider.com}}</ref>
* 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==
] and ] are reacted with a ] ] to form a ]. The next step is ] with ]. This forms the triglycidyl ether.<ref>{{Cite journal |last=Crivello |first=James V. |date=2006 |title=Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization |url=https://doi.org/10.1002/pola.21761 |journal=Journal of Polymer Science Part A: Polymer Chemistry |volume=44 |issue=21 |pages=6435–6448 |doi=10.1002/pola.21761 |bibcode=2006JPoSA..44.6435C |issn=0887-624X}}</ref><ref>{{Cite patent|country=US|pubdate=1992-11-10|assign1=]|number=5162547|title=Process for the preparation of glycidyl ethers|=|inventor1-last=Roth|inventor1-first=Martin|inventor2-last=Wolleb|inventor2-first=Heinz|inventor3-last=Truffer|inventor3-first=Marc-Andre}}</ref>

==Uses==
As the molecule has 3 ] functionalities, it is a reactive modifier and viscosity reduction agent of epoxy resins.<ref>{{Citation |last=Monte |first=Salvatore J. |title=Diluents and viscosity modifiers for epoxy resins |date=1998 |url=https://doi.org/10.1007/978-94-011-5862-6_24 |work=Plastics Additives: An A-Z reference |series=Polymer Science and Technology Series |volume=1 |pages=211–216 |editor-last=Pritchard |editor-first=Geoffrey |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-011-5862-6_24 |isbn=978-94-011-5862-6 |access-date=2022-03-29 |archive-date=2022-04-11 |archive-url=https://web.archive.org/web/20220411203514/https://link.springer.com/chapter/10.1007/978-94-011-5862-6_24 |url-status=live }}</ref> These ] modified epoxy resins may then be further formulated into CASE applications: ]s, ]s, ]s, and ]s.<ref>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</ref> 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.<ref>{{Cite journal |last=Huang |first=Biwu |last2=Chen |first2=Yiwang |last3=Deng |first3=Qilan |date=2008-12-01 |title=Photopolymerization of glycerin triglycidyl ether based systems |url=https://link.springer.com/article/10.1007/s11595-007-6795-2 |journal=Journal of Wuhan University of Technology-Mater. Sci. Ed. |language=en |volume=23 |issue=6 |pages=795–798 |doi=10.1007/s11595-007-6795-2 |issn=1993-0437}}</ref><ref>{{Cite journal |last=Crivello |first=James V. |last2=Ortiz |first2=Ricardo Acosta |date=2001 |title=Synthesis of epoxy monomers that undergo synergistic photopolymerization by a radical-induced cationic mechanism |url=https://onlinelibrary.wiley.com/doi/10.1002/pola.10015 |journal=Journal of Polymer Science Part A: Polymer Chemistry |language=en |volume=39 |issue=20 |pages=3578–3592 |doi=10.1002/pola.10015 |issn=1099-0518}}</ref> Uses in modern battery technology have also been researched.<ref>{{Cite journal |last=Huang |first=Hao |last2=Yi |first2=Linyun |last3=Chen |first3=Xiaoxiao |last4=Wei |first4=Chaohui |last5=Zhou |first5=Aijun |last6=Wang |first6=Yuehui |last7=Li |first7=Jingze |date=2024 |title=A glycerol triglycidyl ether cross-linker assisting an in situ thermally polymerized gel polymer electrolyte for advanced lithium metal batteries |url=https://xlink.rsc.org/?DOI=D4NJ01484G |journal=New Journal of Chemistry |language=en |volume=48 |issue=30 |pages=13631–13638 |doi=10.1039/D4NJ01484G |issn=1144-0546}}</ref> The molecule maybe further reacted to produce materials such as surfactants.<ref>{{Cite journal |last=Zhou |first=Ming |last2=Zhao |first2=Jinzhou |last3=Wang |first3=Xu |last4=Jing |first4=Jiaqiang |last5=Zhou |first5=Lizhi |date=2013 |title=Synthesis and Characterization of Novel Surfactants 1,2,3-tri(2-oxypropylsulfonate-3-alkylether-propoxy) Propanes |url=https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11743-013-1442-8 |journal=Journal of Surfactants and Detergents |language=en |volume=16 |issue=5 |pages=665–672 |doi=10.1007/s11743-013-1442-8 |issn=1558-9293}}</ref>

==Further reading==
* {{Cite book|url=https://www.worldcat.org/oclc/182890|title=Epoxy resin technology.|date=1968|publisher=Interscience Publishers|others=Paul F. Bruins, Polytechnic Institute of Brooklyn|isbn=0-470-11390-1|location=New York|oclc=182890}}
* {{Cite book|last=Flick|first=Ernest W.|url=https://www.worldcat.org/oclc/915134542|title=Epoxy resins, curing agents, compounds, and modifiers : an industrial guide|date=1993|isbn=978-0-8155-1708-5|location=Park Ridge, NJ|oclc=915134542}}
* {{Cite book|last=Lee|first=Henry|url=https://www.worldcat.org/oclc/311631322|title=Handbook of epoxy resins|date=1967|publisher=McGraw-Hill|others=Kris Neville|isbn=0-07-036997-6|edition=|location=New York|oclc=311631322}}

==References==
{{reflist}}

]
]

Latest revision as of 21:30, 10 January 2025

Glycerol triglycidyl ether
Names
Other names Triglycidylglycerol; triglycidyl glycerol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.905 Edit this at Wikidata
EC Number
  • 236-211-1
PubChem CID
UNII
CompTox Dashboard (EPA)
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 260.286 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.
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