Trimethylolpropane triglycidyl ether

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family.^[2][3] It has the formula C₁₅H₂₆O₆ and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3.^[4][5] It also has another CAS number of 30499-70-8^[6][7] A key use is as a modifier for epoxy resins as a reactive diluent.^[8]

Trimethylolpropane triglycidyl ether

Names
IUPAC name 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane
Other names 1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
Identifiers
CAS Number	3454-29-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:189372
ChemSpider	93067
EC Number	222-384-0
PubChem CID	103015
CompTox Dashboard (EPA)	DTXSID90873907
InChI InChI=1S/C15H26O6/c1-2-15(9-16-3-12-6-19-12,10-17-4-13-7-20-13)11-18-5-14-8-21-14/h12-14H,2-11H2,1H3 Key: QECCQGLIYMMHCR-UHFFFAOYSA-N
SMILES CCC(COCC1CO1)(COCC2CO2)COCC3CO3
Properties
Chemical formula	C15H26O6
Molar mass	302.364 g/mol
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H315, H317, H318, H319, H334, H335, H412
Precautionary statements	P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P313, P337+P317, P342+P316, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Alternative names

• Oxirane, 2,2′-[[2-ethyl-2-[(2-oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis-
• Butane, 1-(2,3-epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]-
• Oxirane, 2,2′-[[2-ethyl-2-[(oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis-
• 2,2′-[[2-Ethyl-2-[(2-oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis[oxirane]
• 1,1,1-Trimethylolpropane triglycidyl ether

Manufacture

Trimethylolpropane 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.^[9][10]

Uses

As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins.^[11] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings,^[12] Adhesives,^[13] Sealants,^[14] Elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[15][16] It produces epoxy coatings with high impact resistance^[17] Polymer systems with shape memory may also be produced with this particular molecule.^[18] Fluoropolymers have also been produced with the material via a photoinitiated mechanism.^[19] Production of biocompatible materials is also possible.^[20]

See also

• Epoxide
• Glycidol
• Glycerol triglycidyl ether