C12–C14 alcohol glycidyl ether

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C12–C14 alcohol glycidyl ether

n = 10-12
Names
IUPAC name
2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane
Other names
Alkyl glycidyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.065.295 Edit this at Wikidata
  • InChI=1S/C17H34O2.C16H32O2.C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-17-16-19-17;1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-16-15-18-16;1-2-3-4-5-6-7-8-9-10-11-12-16-13-15-14-17-15/h17H,2-16H2,1H3;16H,2-15H2,1H3;15H,2-14H2,1H3
    Key: CKNWGKWITWNVEY-UHFFFAOYSA-N
  • CCCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCOCC1CO1
Properties
C48H96O6
Molar mass 769.3 g/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family.[2] It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction.[3] It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane.[4] Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

Manufacture[edit]

A fatty alcohol mixture rich in C12-C14 alcohols is placed in a reactor with a Lewis acid catalyst. Then epichlorohydrin is added slowly to control exotherm which results in the formation of the halohydrins.[5] This is followed by a caustic dehydrochlorination, to form C12-C14 alcohol glycidyl ether.[6] The waste products are water and sodium chloride and excess caustic soda.[7] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses[edit]

As an epoxy modifier it is classed as an epoxy reactive diluent.[8] It is one of a family of glycidyl ethers available used for viscosity reduction of epoxy resins.[9] These are then further formulated into coatings, sealants, adhesives, and elastomers.[10][11] Resins with this diluent tend to show improved workability.[12] It is also used to synthesize other molecules.[13][14] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[15][16]

Toxicology[edit]

The toxicology is well known, and it is classed as a skin irritant.[17]

See also[edit]

References[edit]

  1. ^ "Dodecyl and tetradecyl glycidyl ethers". pubchem.ncbi.nlm.nih.gov. Retrieved 12 April 2022.
  2. ^ "Alkyl (C12-C14) glycidyl ether | 68609-97-2". www.chemicalbook.com. Retrieved 2022-04-10.
  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. ^ PubChem. "Dodecyl and tetradecyl glycidyl ethers". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-12.
  5. ^ "Process for the preparation of glycidyl ethers- US Patent 5162547" (PDF). November 1992.
  6. ^ 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.
  7. ^ "Preparation method of alkyl glycidyl ether - Patent CN-113429367-A - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-12.
  8. ^ 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
  9. ^ 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.
  10. ^ 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
  11. ^ 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 2022-04-12
  12. ^ 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.
  13. ^ 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.
  14. ^ 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.
  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. ^ "C&L Inventory". echa.europa.eu. Retrieved 2022-04-12.

Further reading[edit]

External websites[edit]

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