C12–C13 alcohol glycidyl ether explained

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family.[1] It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated.[2] It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction.[3] [4] It has the CAS number 120547-52-6.[5]

Manufacture

A fatty alcohol mixture rich in C12-C13 alcohols is placed in a reactor with a Lewis acid catalyst. Epichlorohydrin is then added slowly to control the exotherm. The reaction results in the formation of the halohydrins.[6] This is followed by a caustic dehydrochlorination, to form C12-C13 alcohol glycidyl ether.[7] The waste products are water and sodium chloride and excess caustic soda.[8] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Synonyms

The material has a number of synonyms.[9]

Uses

As an epoxy modifier it is classed as an epoxy reactive diluent. It is one of a family of glycidyl ethers available used for viscosity reduction of epoxy resins.[10] [11] These are then further formulated into coatings, sealants, adhesives, and elastomers.[12] Resins with this diluent tend to show improved workability.[13] It is also used to synthesize other molecules.[14] [15] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[16] [17]

Toxicology

The toxicology is fairly well known, and it is classed as a skin irritant.[18]

See also

Further reading

External websites

Notes and References

  1. Web site: Chambers . Michael . ChemIDplus - 120547-52-6 - Oxirane, 2-((C12-13-alkyloxy)methyl) derivs. - Searchable synonyms, formulas, resource links, and other chemical information. . 2022-04-29 . chem.nlm.nih.gov . en . 2022-04-29 . https://web.archive.org/web/20220429185334/https://chem.nlm.nih.gov/chemidplus/rn/120547-52-6 . live .
  2. Web site: 120547-52-6 CAS MSDS (Oxirane, mono(C12-13-alkyloxy)methyl derivs.) Melting Point Boiling Point Density CAS Chemical Properties . 2022-04-29 . www.chemicalbook.com . 2022-04-29 . https://web.archive.org/web/20220429185529/https://www.chemicalbook.com/ChemicalProductProperty_US_CB21214417.aspx . live .
  3. Jagtap . Ameya Rajendra . More . Aarti . 2022-08-01 . Developments in reactive diluents: a review . Polymer Bulletin . en . 79 . 8 . 5667–5708 . 10.1007/s00289-021-03808-5 . 235678040 . 1436-2449.
  4. Verkoyen . Patrick . Frey . Holger . August 2020 . Long‐Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers . Macromolecular Rapid Communications . en . 41 . 15 . 2000225 . 10.1002/marc.202000225 . 32567153 . 219973760 . 1022-1336 . free .
  5. Web site: Alkyl (C12-C13) glycidyl ether - Hazardous Agents Haz-Map . 2022-04-29 . haz-map.com . 2022-05-12 . https://web.archive.org/web/20220512202053/https://haz-map.com/Agents/12626?referer=BrowseByAlphabet&return_url=%2FAgents%2F%28BrowseByAlphabet%29%2FA . live .
  6. Web site: November 1992 . Process for the preparation of glycidyl ethers- US Patent 5162547 .
  7. Web site: SJÖVOLD . HENRICK . 2015 . Solvent-Free Synthesis of Glycidyl Ethers : Investigating Factors Influencing the Yield of Alkyl Glycidyl Ethers Master of Science Thesis . Chalmers University Sweden . 2022-05-12 . 2017-08-15 . https://web.archive.org/web/20170815033020/http://publications.lib.chalmers.se/records/fulltext/218842/218842.pdf . live .
  8. Web site: Preparation method of alkyl glycidyl ether - Patent CN-113429367-A - PubChem . 2022-04-12 . pubchem.ncbi.nlm.nih.gov . 2022-04-12 . https://web.archive.org/web/20220412144546/https://pubchem.ncbi.nlm.nih.gov/patent/CN-113429367-A . live .
  9. Web site: 120547-52-6 CAS MSDS (Oxirane, mono(C12-13-alkyloxy)methyl derivs.) Melting Point Boiling Point Density CAS Chemical Properties . 2022-04-29 . www.chemicalbook.com . 2022-04-29 . https://web.archive.org/web/20220429185529/https://www.chemicalbook.com/ChemicalProductProperty_US_CB21214417.aspx . live .
  10. Web site: Office . European Patent . European publication server . 2022-04-29 . data.epo.org . en . 2022-05-12 . https://web.archive.org/web/20220512202058/https://data.epo.org/publication-server/document?iDocId=6766801&iFormat=0 . live .
  11. Ali . M. . Hammami . A. . July 2005 . Experimental modeling of the cure behavior of a formulated blend of DGEBA epoxy and C12-C14 glycidyl ether as a reactive diluent . Polymer Composites . en . 26 . 5 . 593–603 . 10.1002/pc.20131 . 0272-8397 . 2022-05-12 . 2022-04-12 . https://web.archive.org/web/20220412145713/https://onlinelibrary.wiley.com/doi/10.1002/pc.20131 . live .
  12. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 23,24,39 Master of Science Thesis April 1997 Imperial College London
  13. Ozeren Ozgul . Eren . Ozkul . M. Hulusi . 2018-01-15 . Effects of epoxy, hardener, and diluent types on the workability of epoxy mixtures . Construction and Building Materials . en . 158 . 369–377 . 10.1016/j.conbuildmat.2017.10.008 . 0950-0618 . 2022-05-12 . 2022-05-12 . https://web.archive.org/web/20220512202057/https://www.sciencedirect.com/science/article/pii/S095006181732038X . live .
  14. 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 .
  15. Verkoyen . Patrick . Frey . Holger . August 2020 . Long‐Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers . Macromolecular Rapid Communications . en . 41 . 15 . 2000225 . 10.1002/marc.202000225 . 32567153 . 1022-1336. free .
  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 . en . 76 . 8 . 3905–3927 . 10.1007/s00289-018-2577-6 . 105389177 . 1436-2449.
  17. 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.
  18. Web site: Canada . Environment and Climate Change . 2020-08-07 . Screening assessment - Epoxides and Glycidyl Ethers Group . 2022-04-29 . www.canada.ca . 2022-03-24 . https://web.archive.org/web/20220324190040/https://www.canada.ca/en/environment-climate-change/services/evaluating-existing-substances/screening-assessment-epoxides-glycidyl-ethers-group.html . live .

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