C12–C13 alcohol glycidyl ether

C12–C13 alcohol glycidyl ether

n = 10-11
Identifiers
CAS Number	120547-52-6
3D model (JSmol)	Interactive image
EC Number	271-846-8
SMILES CCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCOCC1CO1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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, 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]

• Oxirane, mono (C12-13-alkyloxy) methyl derivatives
• Alkyl(C12-C13) glycidyl ether
• Alkyl glycidyl ether
• Oxirane, Mono (C12-C13 alkoxymethyl) methyl derivatives
• (C12-C13)alkylglycidyl ether
• Oxirane, 2-[(C12-13-alkyloxy)methyl] derivatives

Uses

As an epoxy modifier it is classed as an epoxy reactive diluent. ^[10] It is one of a family of glycidyl ethers available used for viscosity reduction of epoxy resins. ^{[11] [12]} These are then further formulated into coatings, sealants, adhesives, and elastomers. ^{[13] [14]} Resins with this diluent tend to show improved workability. ^[15] It is also used to synthesize other molecules. ^{[16] [17]} The use of the diluent does effect mechanical properties and microstructure of epoxy resins. ^{[18] [19]}

Toxicology

The toxicology is fairly well known, and it is classed as a skin irritant. ^[20]

See also

• Epoxide
• Glycidol

References

1. Chambers, Michael. "ChemIDplus - 120547-52-6 - Oxirane, 2-((C12-13-alkyloxy)methyl) derivs. - Searchable synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov. Archived from the original on 2022-04-29. Retrieved 2022-04-29.
2. "120547-52-6 CAS MSDS (Oxirane, mono(C12-13-alkyloxy)methyl derivs.) Melting Point Boiling Point Density CAS Chemical Properties". www.chemicalbook.com. Archived from the original on 2022-04-29. Retrieved 2022-04-29.
3. 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.
4. Verkoyen, Patrick; Frey, Holger (August 2020). "Long-Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers". Macromolecular Rapid Communications. 41 (15): 2000225. doi: 10.1002/marc.202000225 . ISSN   1022-1336. PMID   32567153. S2CID   219973760.
5. "Alkyl (C12-C13) glycidyl ether - Hazardous Agents | Haz-Map". haz-map.com. Archived from the original on 2022-05-12. Retrieved 2022-04-29.
6. "Process for the preparation of glycidyl ethers- US Patent 5162547" (PDF). November 1992.
7. SJÖVOLD, HENRICK (2015). "Solvent-Free Synthesis of Glycidyl Ethers : Investigating Factors Influencing the Yield of Alkyl Glycidyl Ethers Master of Science Thesis" (PDF). Chalmers University Sweden. Archived (PDF) from the original on 2017-08-15. Retrieved 2022-05-12.
8. "Preparation method of alkyl glycidyl ether - Patent CN-113429367-A - PubChem". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2022-04-12. Retrieved 2022-04-12.
9. "120547-52-6 CAS MSDS (Oxirane, mono(C12-13-alkyloxy)methyl derivs.) Melting Point Boiling Point Density CAS Chemical Properties". www.chemicalbook.com. Archived from the original on 2022-04-29. Retrieved 2022-04-29.
10. 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
11. Office, European Patent. "European publication server". data.epo.org. Archived from the original on 2022-05-12. Retrieved 2022-04-29.
12. 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. 26 (5): 593–603. doi:10.1002/pc.20131. ISSN   0272-8397. Archived from the original on 2022-04-12. Retrieved 2022-05-12.
13. 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
14. 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 2022-04-12
15. 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. 158: 369–377. doi:10.1016/j.conbuildmat.2017.10.008. ISSN   0950-0618. Archived from the original on 2022-05-12. Retrieved 2022-05-12.
16. 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.
17. Verkoyen, Patrick; Frey, Holger (August 2020). "Long-Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers". Macromolecular Rapid Communications. 41 (15): 2000225. doi: 10.1002/marc.202000225 . ISSN   1022-1336. PMID   32567153.
18. 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.
19. 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.
20. Canada, Environment and Climate Change (2020-08-07). "Screening assessment - Epoxides and Glycidyl Ethers Group". www.canada.ca. Archived from the original on 2022-03-24. Retrieved 2022-04-29.

Further reading

• Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN   0-470-11390-1. OCLC   182890.
• 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.
• 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).

External websites

• Denacol epoxy diluent range
• Reactive Diluents – Olin Epoxy
• Hexion Epoxy Functional Modifiers
• Cargill Reactive diluents