Glycerol triglycidyl ether

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]

Glycerol triglycidyl ether

Names
Other names Triglycidylglycerol; triglycidyl glycerol
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,1-8H2 Key: SYEWHONLFGZGLK-UHFFFAOYSA-N
SMILES C1C(O1)COCC(COCC2CO2)OCC3CO3
Properties
Chemical formula	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). Infobox references

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]