Trimethylolpropane triglycidyl ether

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:
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

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]

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]

References

^ "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 13 April 2022.
^ PubChem. "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-11.
^ "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.
^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2022-04-12.
^ "Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3". www.chemindustry.com. Retrieved 2022-04-12.
^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-12.
^ "Trimethylolpropane triglycidyl ether". www.carbosynth.com. Retrieved 2022-04-12.
^ 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.
^ 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.
^ 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.
^ 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
^ WO application 2019238867, Bevinakatti, Hanamanthsa & Islam, Mojahedul, "Herbicidal formulations comprising glyphosate and cote-based adjuvants", published 2019-12-19, assigned to Nouryon Chemicals International BV
^ Hao, Xiu; Fan, Dong-Bin (2018-12-17). "Preparation and characterization of epoxy-crosslinked soy protein adhesive". Journal of Adhesion Science and Technology. 32 (24): 2682–2692. doi:10.1080/01694243.2018.1517488. ISSN 0169-4243. S2CID 105550538.
^ "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
^ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.
^ US 8062468, Finter, Jürgen; Kramer, Andreas & Schulenburg, Jan Olaf et al., "Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins", published 2011-11-22, assigned to Sika Technology AG
^ Santiago, David; Guzmán, Dailyn; Ferrando, Francesc; Serra, Àngels; De la Flor, Silvia (March 2020). "Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol". Polymers. 12 (3): 542. doi:10.3390/polym12030542. ISSN 2073-4360. PMC 7182903. PMID 32131508.
^ Trusiano, Giuseppe; Vitale, Alessandra; Bonneaud, Céline; Pugliese, Diego; Dalle Vacche, Sara; Joly-Duhamel, Christine; Friesen, Chadron M.; Bongiovanni, Roberta (2021-03-01). "Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers". Colloid and Polymer Science. 299 (3): 509–521. doi:10.1007/s00396-020-04723-3. ISSN 1435-1536. PMC 7952294. PMID 33785978.
^ "Journal of Electrochemical Science and Technology". www.jecst.org. Retrieved 2022-04-12.

External websites

[1] "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 13 April 2022.

[2] PubChem. "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-11.

[3] "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.

[4] "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2022-04-12.

[5] "Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3". www.chemindustry.com. Retrieved 2022-04-12.

[6] "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-12.

[7] "Trimethylolpropane triglycidyl ether". www.carbosynth.com. Retrieved 2022-04-12.

[8] 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.

[9] 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.

[10] 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.

[11] 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

[12] WO application 2019238867, Bevinakatti, Hanamanthsa & Islam, Mojahedul, "Herbicidal formulations comprising glyphosate and cote-based adjuvants", published 2019-12-19, assigned to Nouryon Chemicals International BV

[13] Hao, Xiu; Fan, Dong-Bin (2018-12-17). "Preparation and characterization of epoxy-crosslinked soy protein adhesive". Journal of Adhesion Science and Technology. 32 (24): 2682–2692. doi:10.1080/01694243.2018.1517488. ISSN 0169-4243. S2CID 105550538.

[14] "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.

[15] Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.

[16] Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.

[17] US 8062468, Finter, Jürgen; Kramer, Andreas & Schulenburg, Jan Olaf et al., "Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins", published 2011-11-22, assigned to Sika Technology AG

[18] Santiago, David; Guzmán, Dailyn; Ferrando, Francesc; Serra, Àngels; De la Flor, Silvia (March 2020). "Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol". Polymers. 12 (3): 542. doi:10.3390/polym12030542. ISSN 2073-4360. PMC 7182903. PMID 32131508.

[19] Trusiano, Giuseppe; Vitale, Alessandra; Bonneaud, Céline; Pugliese, Diego; Dalle Vacche, Sara; Joly-Duhamel, Christine; Friesen, Chadron M.; Bongiovanni, Roberta (2021-03-01). "Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers". Colloid and Polymer Science. 299 (3): 509–521. doi:10.1007/s00396-020-04723-3. ISSN 1435-1536. PMC 7952294. PMID 33785978.

[20] "Journal of Electrochemical Science and Technology". www.jecst.org. Retrieved 2022-04-12.

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v t e Ethers of glycidol
Mono-epoxy	Allyl glycidyl ether n-Butyl glycidyl ether C12–C13 alcohol glycidyl ether C12–C14 alcohol glycidyl ether o-Cresyl glycidyl ether 2-Ethylhexyl glycidyl ether Phenyl glycidyl ether
Di-epoxy	Bisphenol A diglycidyl ether 1,4-Butanediol diglycidyl ether 1,4-Cyclohexanedimethanol diglycidyl ether Diethylene glycol diglycidyl ether Diglycidyl ether Diglycidyl resorcinol ether 1,6-Hexanediol diglycidyl ether Neopentyl glycol diglycidyl ether
Tri-epoxy	Castor oil glycidyl ether Trimethylolethane triglycidyl ether Trimethylolpropane triglycidyl ether
Category