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2-Ethylhexyl glycidyl ether
Reference material by Wikipedia contributors. This retains its source identity and is not 411 news reporting.
2-ethylhexyl glycidyl ether.svg 200px {[(2-Ethylhexyl)oxy]methyl}oxirane 2461-15-6 1412431 16246 219-553-6 17162 LU1UZ98B89 1S/C11H22O2/c1-3-5-6-10(4-2)7-12-8-11-9-13-11/h10-11H,3-9H2,1-2H3 BBBUAWSVILPJLL-UHFFFAOYSA-N O(CC1OC1)CC(CC)CCCC
11 22 2
2-Ethylhexyl glycidyl ether https://pubchem.ncbi.nlm.nih.gov/compound/17162#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 27 March 2022 en 07 Warning 315 317 319 335 261 264 264+265 271 272 280 302+352 304+340 305+351+338 319 321 332+317 333+313 337+317 362+364 403+233 405 501
2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2Oxirane, [[(2-ethylhexyl)oxy]methyl]- (CAS 2461-15-6) - Chemical & Physical Properties by Cheméo https://www.chemeo.com/cid/20-494-1/Oxirane,%20%5B%5B(2-ethylhexyl)oxy%5Dmethyl%5D- 2022-03-23 www.chemeo.com en an industrial chemical used to reduce the viscosity of epoxy resins.TZ3300000 C11H22O2 ChemSpider http://www.chemspider.com/Chemical-Structure.16246.html 2022-03-23 www.chemspider.com These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6.Sigma Aldrich catalogue 2-ethyl hexyl clycidyl ether https://www.sigmaaldrich.com/US/en/product/aldrich/251747?gclid=CjwKCAjwiuuRBhBvEiwAFXKaNFsWtQCZxQs7zzX3vcT87jBr21i8v6unEHhgTqDm_106N51w973APRoCf8EQAvD_BwE 2022-03-232-Ethylhexyl glycidyl ether 2461-15-6 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7212453.htm#:~:text=2-Ethylhexyl%20glycidyl%20ether%20Chemical%20Properties,Usage,Production&text=Uses%20It%20constitutes%20a%20reactive,as%20a%20commercial%20reactive%20diluent. 2022-03-23 www.chemicalbook.com2-ethylhexyl glycidyl ether - Wikidata It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.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 https://doi.org/10.1021/acsabm.0c01550 ACS Applied Bio Materials 4 4 3133–3144 10.1021/acsabm.0c01550 35014401 233957334 free
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.Glycidyl 2-Ethylhexyl Ether 2461-15-6 2004-10-15 http://dx.doi.org/10.1002/0471701343.sdp13115 Sax's Dangerous Properties of Industrial Materials Hoboken, NJ, USA John Wiley & Sons, Inc. 10.1002/0471701343.sdp13115 0471701343 2022-03-23 subscription 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. 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.Chem A. A. L. ME 102 https://www.aalchem.com/en/product/category/diluent-dilu/2-ethylhexyl-glycidyl-ether-me-102 2022-03-23 www.aalchem.com en Over 13 million kg were exported from China in 2019.What Is 2-Ethylhexyl Glycidylether, Cas No 2461-15-6 Guide https://www.echemi.com/products/pid_Seven17560-2-ethylhexylglycidylether.html 2022-03-23 ECHEMI
Uses
As an Epoxy modifier it is classed as an epoxy reactive diluent.Monte Salvatore J. Diluents and viscosity modifiers for epoxy resins 1998 https://doi.org/10.1007/978-94-011-5862-6_24 Plastics Additives: An A-Z reference Polymer Science and Technology Series 1 211–216 Pritchard Geoffrey Dordrecht Springer Netherlands en 10.1007/978-94-011-5862-6_24 978-94-011-5862-6 2022-03-29 subscription As well as being used as an epoxy resin diluent, it maybe further reacted to produce cosmetics.Office European Patent European publication server https://data.epo.org/publication-server/document?iDocId=5999858&iFormat=0 2022-03-23 data.epo.org en It is also used to synthesize other molecules.Urata Kouichi Takaishi Naotake September 1994 The alkyl glycidyl ether as synthetic building blocks http://doi.wiley.com/10.1007/BF02542274 Journal of the American Oil Chemists' Society en 71 9 1027–1033 10.1007/BF02542274 96776835 subscription The use of the diluent does effect mechanical properties and microstructure of epoxy resins.Khalina Morteza Beheshty Mohammad Hosain Salimi Ali 2019-08-01 The effect of reactive diluent on mechanical properties and microstructure of epoxy resins https://doi.org/10.1007/s00289-018-2577-6 Polymer Bulletin en 76 8 3905–3927 10.1007/s00289-018-2577-6 105389177 1436-2449 subscription 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 https://doi.org/10.1007/s11998-022-00737-4 Journal of Coatings Technology and Research en 20 4 1207–1221 10.1007/s11998-022-00737-4 256749849 1935-3804 subscription
Safety
The safety of the product is fairly well understood. It is classed as a skin sensitizer.Substance Information - ECHA https://echa.europa.eu/substance-information/-/substanceinfo/100.017.776 2022-03-23 echa.europa.eu en-GBNIOSHTIC-2 Publications Search - 00188271 - Information profiles on potential occupational hazards: epoxy compounds (non-cyclic). https://www.cdc.gov/niosh/nioshtic-2/00188271.html 2022-03-23 www.cdc.govCanada Environment and Climate Change 2020-08-07 Screening assessment - Epoxides and Glycidyl Ethers Group https://www.canada.ca/en/environment-climate-change/services/evaluating-existing-substances/screening-assessment-epoxides-glycidyl-ethers-group.html 2022-03-23 www.canada.ca
See also
Epoxide
Glycidol
References
Further reading
Epoxy resin technology. 1968 Interscience Publishers Paul F. Bruins, Polytechnic Institute of Brooklyn 0-470-11390-1 New York 182890
Flick Ernest W. Epoxy resins, curing agents, compounds, and modifiers : an industrial guide 1993 978-0-8155-1708-5 Park Ridge, NJ 915134542
Lee Henry Handbook of epoxy resins 1967 McGraw-Hill Kris Neville 0-07-036997-6 [2nd, expanded work] New York 311631322
http://nmt.edu/academics/mtls/faculty/mccoy/docs2/chemistry/DowEpoxyResins.pdf Dow Epoxy Resins
External Websites
Sachem Glycidyl Ethers
Cameo Chemicals
Hexion website
Miller-Stephenson Diluents
Category:Glycidyl ethers
Category:Reactive diluents