2-Ethylhexyl glycidyl ether explained

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C₁₁H₂₂O₂^[1] an industrial chemical used to reduce the viscosity of epoxy resins.^[2] These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6.^{[3] [4] [5]} It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.^[6]

Synthesis

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.^[7] 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.

Commercial

The material is produced domestically in the United States and is also produced in other parts of the world.^[8] Over 13 million kg were exported from China in 2019.^[9]

Uses

As an Epoxy modifier it is classed as an epoxy reactive diluent. As well as being used as an epoxy resin diluent, it maybe further reacted to produce cosmetics.^[10] It is also used to synthesize other molecules.^[11] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^{[12] [13]}

Safety

The safety of the product is fairly well understood. It is classed as a skin sensitizer.^{[14] [15] [16]}

See also

• Epoxide
• Glycidol

Further reading

• Book: Epoxy resin technology.. 1968. Interscience Publishers. Paul F. Bruins, Polytechnic Institute of Brooklyn. 0-470-11390-1. New York. 182890.
• Book: Flick, Ernest W.. Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. 1993. 978-0-8155-1708-5. Park Ridge, NJ. 915134542.
• Book: Lee, Henry. Handbook of epoxy resins. 1967. McGraw-Hill. Kris Neville. 0-07-036997-6. [2nd, expanded work]. New York. 311631322.
• Web site: Dow Epoxy Resins.

External Websites

• Sachem Glycidyl Ethers
• Cameo Chemicals
• Hexion website
• Miller-Stephenson Diluents

Notes and References

1. Web site: Oxirane, (2-ethylhexyl)oxymethyl]- (CAS 2461-15-6) - Chemical & Physical Properties by Cheméo ]. 2022-03-23 . www.chemeo.com . en.
2. Web site: TZ3300000 C11H22O2 ChemSpider . 2022-03-23 . www.chemspider.com.
3. Web site: Sigma Aldrich catalogue 2-ethyl hexyl clycidyl ether . 2022-03-23.
4. Web site: 2-Ethylhexyl glycidyl ether 2461-15-6 . 2022-03-23 . www.chemicalbook.com.
5. 2-ethylhexyl glycidyl ether - Wikidata
6. 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 . 10.1021/acsabm.0c01550. 35014401 . 233957334 .
7. 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.
8. Web site: Chem . A. A. L. . ME 102 . 2022-03-23 . www.aalchem.com . en.
9. Web site: What Is 2-Ethylhexyl Glycidylether, Cas No 2461-15-6 Guide . 2022-03-23 . ECHEMI.
10. Web site: Office . European Patent . European publication server . 2022-03-23 . data.epo.org . en.
11. Urata . Kouichi . Takaishi . Naotake . September 1994 . The alkyl glycidyl ether as synthetic building blocks . Journal of the American Oil Chemists' Society . en . 71 . 9 . 1027–1033 . 10.1007/BF02542274. 96776835 .
12. 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 . en . 76 . 8 . 3905–3927 . 10.1007/s00289-018-2577-6 . 105389177 . 1436-2449.
13. 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 . en . 20 . 4 . 1207–1221 . 10.1007/s11998-022-00737-4 . 256749849 . 1935-3804.
14. Web site: Substance Information - ECHA . 2022-03-23 . echa.europa.eu . en-GB.
15. Web site: NIOSHTIC-2 Publications Search - 00188271 - Information profiles on potential occupational hazards: epoxy compounds (non-cyclic). . 2022-03-23 . www.cdc.gov.
16. Web site: Canada . Environment and Climate Change . 2020-08-07 . Screening assessment - Epoxides and Glycidyl Ethers Group . 2022-03-23 . www.canada.ca.