Castor oil glycidyl ether

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12 and the CAS number 14228-73-0.[2] The IUPAC name is 2,3-bis[12-(oxiran-2-ylmethoxy)octadec-9-enoyloxy]propyl 12-(oxiran-2-ylmethoxy)octadec-9-enoate.[3] A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.[4][5]

Castor oil glycidyl ether
Names
IUPAC name
2,3-bis[12-(oxiran-2-ylmethoxy)octadec-9-enoyloxy]propyl 12-(oxiran-2-ylmethoxy)octadec-9-enoate
Identifiers
3D model (JSmol)
EC Number
  • 616-085-8
  • InChI=1S/C66H116O12/c1-4-7-10-31-40-57(70-49-60-52-73-60)43-34-25-19-13-16-22-28-37-46-64(67)76-55-63(78-66(69)48-39-30-24-18-15-21-27-36-45-59(42-33-12-9-6-3)72-51-62-54-75-62)56-77-65(68)47-38-29-23-17-14-20-26-35-44-58(41-32-11-8-5-2)71-50-61-53-74-61/h25-27,34-36,57-63H,4-24,28-33,37-56H2,1-3H3
    Key: ZFJYZDDXGKWNCH-UHFFFAOYSA-N
  • CCCCCCC(CC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCC(CCCCCC)OCC1CO1)OC(=O)CCCCCCCC=CCC(CCCCCC)OCC2CO2)OCC3CO3
Properties
C66H16O12
Molar mass 1101.6 g/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Manufacture

It is made by glycidation of castor oil which is a vegetable oil. Castor oil and epichlorohydrin are reacted in the presence of a Lewis acid catalyst to form halohydrin: each hydroxyl group of the triol reacts with an epoxide on epichlorohydrin. This process is followed neutralizing the catalyst with a small amount of sodium hydroxide and then adding a large excess of epichlorohydrin as solvent. To re-form the epoxide rings in a dehydrochlorination reaction, solid sodium hydroxide flake is used rather than a solution. On completion the epichlorohydrin is recovered and the product cleaned up.[6] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Uses

A 2018 study concluded that its use as a flexiblizing agent as well as an epoxy diluent has application in the aviation field.[7] Poly(propylene glycol) diglycidyl ether may also be used for the same application but has the perceived disadvantage that it is petroleum based rather than renewable plant based like the castor oil glycidyl ether. A patent application shows it may also be used as a co-reactant-surfactant in herbicide production.[8] As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins.[9][10] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,[11] adhesives,[12] sealants,[13] elastomers. It is also used in composite production.[14] It produces epoxy coatings with high impact resistance.[15] Polymer systems with shape memory may also be produced with this particular molecule.[16] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[17][18] Production of biocompatible materials is also possible and the material is often classed as a renewable resource.[19][20] It has also found use in oil well petroleum recovery.[21]

See also

References
  1. "Homopolymer of glyceryl triester with 12-glycidyl-9-octadecenoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 20 April 2022.
  2. "CASTOR OIL GLYCIDYL ETHER | 74398-71-3". www.chemicalbook.com. Retrieved 2022-04-18.
  3. PubChem. "Castor oil glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-19.
  4. Fu, Qinghe; Tan, Jihuai; Han, Changhao; Zhang, Xiaoxiang; Fu, Bo; Wang, Fang; Zhu, Xinbao (November 2020). "Synthesis and curing properties of castor oil‐based triglycidyl ether epoxy resin". Polymers for Advanced Technologies. 31 (11): 2552–2560. doi:10.1002/pat.4982. ISSN 1042-7147. S2CID 225739893.
  5. 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.
  6. US 3351574, Hicks, Darrel D. & Belanger, William J., "Castor oil polyglycidyl ether", published 1967-11-07, assigned to Celanese Coatings Co.
  7. Ramon, Eric; Sguazzo, Carmen; Moreira, Pedro M. G. P. (October 2018). "A Review of Recent Research on Bio-Based Epoxy Systems for Engineering Applications and Potentialities in the Aviation Sector". Aerospace. 5 (4): 110. Bibcode:2018Aeros...5..110R. doi:10.3390/aerospace5040110. ISSN 2226-4310.
  8. WO application 2019238867, Bevinakatti, Hanamanthsa & Islam, Mojahedul, "Herbicidal formulations comprising glyphosate and cote-based adjuvants", published 2019-12-19, assigned to Nouryon Chemicals International BV
  9. Zarnitz, Charles. "Flexibilizing modifiers" (PDF). CVC Thermosets.
  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, Dordrecht: Springer Netherlands, vol. 1, 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. WO application 2015095994, Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published 2015-07-02, assigned to Dow Global Technologies LLC
  12. Hao, Xiu; Fan, Dong-Bin (2018-12-17). "Preparation and characterization of epoxy-crosslinked soy protein adhesive". Journal of Adhesion Science and Technology. 32 (24): 2682–2692. doi:10.1080/01694243.2018.1517488. ISSN 0169-4243. S2CID 105550538.
  13. "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  14. Sathyaraj, S.; Sekar, K. (2021). "Recent Advances in Bio-Based Sustainable Aliphatic and Aromatic Epoxy Resins for Composite Applications". Key Engineering Materials. 882: 121–131. doi:10.4028/www.scientific.net/KEM.882.121. ISSN 1662-9795. S2CID 233301700.
  15. US 8062468, Finter, Jürgen; Kramer, Andreas & Schulenburg, Jan Olaf et al., "Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins", published 2011-11-22, assigned to Sika Technology AG
  16. Santiago, David; Guzmán, Dailyn; Ferrando, Francesc; Serra, Àngels; De la Flor, Silvia (March 2020). "Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol". Polymers. 12 (3): 542. doi:10.3390/polym12030542. ISSN 2073-4360. PMC 7182903. PMID 32131508.
  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. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
  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. Mashouf Roudsari, Ghodsieh; Mohanty, Amar K.; Misra, Manjusri (2017-11-06). "Green Approaches To Engineer Tough Biobased Epoxies: A Review". ACS Sustainable Chemistry & Engineering. 5 (11): 9528–9541. doi:10.1021/acssuschemeng.7b01422. ISSN 2168-0485.
  20. Ma, Yufeng; Wang, Rui; Li, Qiaoguang; Li, Mei; Liu, Chengguo; Jia, Puyou (2021-03-24). "Castor oil as a platform for preparing bio-based chemicals and polymer materials". Green Materials. 10 (3): 99–109. doi:10.1680/jgrma.20.00085. ISSN 2049-1220. S2CID 233687152.
  21. US application 2010326660, Ballard, David Antony & Burn, Andrew, "Use of direct epoxy emulsions for wellbore stabilization", published 2010-12-30, assigned to M-I LLC, since abandoned.

Further reading

External websites
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