2-Ethylhexyl glycidyl ether

2-Ethylhexyl glycidyl ether
Names
	IUPAC name 2-(2-Ethylhexoxymethyl)oxirane
Identifiers
CAS Number	2461-15-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1412431;
ChemSpider	16246;
ECHA InfoCard	100.017.776
EC Number	219-553-6;
PubChem CID	17162;
UNII	LU1UZ98B89;
CompTox Dashboard (EPA)	DTXSID6025301 ;
	InChI InChI=1S/C11H22O2/c1-3-5-6-10(4-2)7-12-8-11-9-13-11/h10-11H,3-9H2,1-2H3 Key: BBBUAWSVILPJLL-UHFFFAOYSA-N;
	SMILES O(CC1OC1)CC(CC)CCCC;
Properties
Chemical formula	C11H22O2
Molar mass	186.295 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, 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

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C₁₁H₂₂O₂^[2] an industrial chemical used to reduce the viscosity of epoxy resins.^[3] These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6.^[4]^[5]^[6] It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.^[7]

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2-Ethylhexanol and epichlorohydrin are reacted in the presence of a Lewis acid catalyst in a condensation reaction to form a halohydrin. This is followed by a caustic dehydrochlorination, to form 2-ethylhexyl glycidyl ether.^[8]^[9] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

The material is produced domestically in the United States and is also produced in other parts of the world.^[10] Over 13 million kg were exported from China in 2019.^[11]

As an Epoxy modifier it is classed as an epoxy reactive diluent.^[12] As well as being used as an epoxy resin diluent, it maybe further reacted to produce cosmetics.^[13] It is also used to synthesize other molecules.^[14] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[15]^[16]

The safety of the product is fairly well understood. It is classed as a skin sensitizer.^[17]^[18]^[19]

[1]
"2-Ethylhexyl glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 27 March 2022.
[2]
"Oxirane, [[(2-ethylhexyl)oxy]methyl]- (CAS 2461-15-6) - Chemical & Physical Properties by Cheméo". www.chemeo.com. Retrieved 2022-03-23.
[3]
"TZ3300000 | C11H22O2 | ChemSpider". www.chemspider.com. Retrieved 2022-03-23.
[4]
"Sigma Aldrich catalogue 2-ethyl hexyl clycidyl ether". Retrieved 2022-03-23.
[5]
"2-Ethylhexyl glycidyl ether | 2461-15-6". www.chemicalbook.com. Retrieved 2022-03-23.
[6]
2-ethylhexyl glycidyl ether - Wikidata
[7]
Deralia, Parveen Kumar; du Poset, Aline Maire; Lund, Anja; Larsson, Anette; Ström, Anna; Westman, Gunnar (2021-04-19). "Oxidation Level and Glycidyl Ether Structure Determine Thermal Processability and Thermomechanical Properties of Arabinoxylan-Derived Thermoplastics". ACS Applied Bio Materials. 4 (4): 3133–3144. doi:10.1021/acsabm.0c01550. PMID 35014401. S2CID 233957334.
[8]
"Glycidyl 2-Ethylhexyl Ether 2461-15-6", Sax's Dangerous Properties of Industrial Materials, Hoboken, NJ, USA: John Wiley & Sons, Inc., 2004-10-15, doi:10.1002/0471701343.sdp13115, ISBN 0471701343, retrieved 2022-03-23
[9]
SpadŁo, M. & Iwański, L. & Pokorska, Z.. (2004). The effect of catalyst type on the synthesis of 2-ethylhexyl glycidyl ether. Przemysl Chemiczny. 83. 133-136.
[10]
Chem, A. A. L. "ME 102". www.aalchem.com. Retrieved 2022-03-23.
[11]
"What Is 2-Ethylhexyl Glycidylether, Cas No 2461-15-6 Guide". ECHEMI. Retrieved 2022-03-23.
[12]
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, retrieved 2022-03-29
[13]
Office, European Patent. "European publication server". data.epo.org. Retrieved 2022-03-23.
[14]
Urata, Kouichi; Takaishi, Naotake (September 1994). "The alkyl glycidyl ether as synthetic building blocks". Journal of the American Oil Chemists' Society. 71 (9): 1027–1033. doi:10.1007/BF02542274. S2CID 96776835.
[15]
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.
[16]
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.
[17]
"Substance Information - ECHA". echa.europa.eu. Retrieved 2022-03-23.
[18]
"NIOSHTIC-2 Publications Search - 00188271 - Information profiles on potential occupational hazards: epoxy compounds (non-cyclic)". www.cdc.gov. Retrieved 2022-03-23.
[19]
Canada, Environment and Climate Change (2020-08-07). "Screening assessment - Epoxides and Glycidyl Ethers Group". www.canada.ca. Retrieved 2022-03-23.

Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.{{cite book}}: CS1 maint: others (link)
Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.{{cite book}}: CS1 maint: location missing publisher (link)
Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.
"Dow Epoxy Resins" (PDF).

[1] [1]
"2-Ethylhexyl glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 27 March 2022.

[2] [2]
"Oxirane, [[(2-ethylhexyl)oxy]methyl]- (CAS 2461-15-6) - Chemical & Physical Properties by Cheméo". www.chemeo.com. Retrieved 2022-03-23.

[3] [3]
"TZ3300000 | C11H22O2 | ChemSpider". www.chemspider.com. Retrieved 2022-03-23.

[4] [4]
"Sigma Aldrich catalogue 2-ethyl hexyl clycidyl ether". Retrieved 2022-03-23.

[5] [5]
"2-Ethylhexyl glycidyl ether | 2461-15-6". www.chemicalbook.com. Retrieved 2022-03-23.

[6] [6]
2-ethylhexyl glycidyl ether - Wikidata

[7] [7]
Deralia, Parveen Kumar; du Poset, Aline Maire; Lund, Anja; Larsson, Anette; Ström, Anna; Westman, Gunnar (2021-04-19). "Oxidation Level and Glycidyl Ether Structure Determine Thermal Processability and Thermomechanical Properties of Arabinoxylan-Derived Thermoplastics". ACS Applied Bio Materials. 4 (4): 3133–3144. doi:10.1021/acsabm.0c01550. PMID 35014401. S2CID 233957334.

[8] [8]
"Glycidyl 2-Ethylhexyl Ether 2461-15-6", Sax's Dangerous Properties of Industrial Materials, Hoboken, NJ, USA: John Wiley & Sons, Inc., 2004-10-15, doi:10.1002/0471701343.sdp13115, ISBN 0471701343, retrieved 2022-03-23

[9] [9]
SpadŁo, M. & Iwański, L. & Pokorska, Z.. (2004). The effect of catalyst type on the synthesis of 2-ethylhexyl glycidyl ether. Przemysl Chemiczny. 83. 133-136.

[10] [10]
Chem, A. A. L. "ME 102". www.aalchem.com. Retrieved 2022-03-23.

[11] [11]
"What Is 2-Ethylhexyl Glycidylether, Cas No 2461-15-6 Guide". ECHEMI. Retrieved 2022-03-23.

[12] [12]
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, retrieved 2022-03-29

[13] [13]
Office, European Patent. "European publication server". data.epo.org. Retrieved 2022-03-23.

[14] [14]
Urata, Kouichi; Takaishi, Naotake (September 1994). "The alkyl glycidyl ether as synthetic building blocks". Journal of the American Oil Chemists' Society. 71 (9): 1027–1033. doi:10.1007/BF02542274. S2CID 96776835.

[15] [15]
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.

[16] [16]
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.

[17] [17]
"Substance Information - ECHA". echa.europa.eu. Retrieved 2022-03-23.

[18] [18]
"NIOSHTIC-2 Publications Search - 00188271 - Information profiles on potential occupational hazards: epoxy compounds (non-cyclic)". www.cdc.gov. Retrieved 2022-03-23.

[19] [19]
Canada, Environment and Climate Change (2020-08-07). "Screening assessment - Epoxides and Glycidyl Ethers Group". www.canada.ca. Retrieved 2022-03-23.

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2-Ethylhexyl glycidyl ether

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2-Ethylhexyl glycidyl ether

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Synthesis

Commercial

Uses

Safety

See also

References

Further reading

External Websites