Castor oil glycidyl ether explained

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. There are two CAS numbers in use, 14228-73-0 and 74398-71-3.[1] The IUPAC name is 2,3-bis[[(E)-12-(oxiran-2-ylmethoxy)octadec-9-enoyl]oxy]propyl (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoate.[2] A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.[3] [4]

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.[5] 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.[6] 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.[7] As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins.[8] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,[9] adhesives,[10] sealants,[11] elastomers. It is also used in composite production.[12] It produces epoxy coatings with high impact resistance.[13] Polymer systems with shape memory may also be produced with this particular molecule.[14] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[15] [16] Production of biocompatible materials is also possible and the material is often classed as a renewable resource.[17] [18] It has also found use in oil well petroleum recovery.[19]

See also

Further reading

External websites

Notes and References

  1. Web site: CASTOR OIL GLYCIDYL ETHER 74398-71-3 . 2022-04-18 . www.chemicalbook.com.
  2. Web site: PubChem . Castor oil glycidyl ether . 2022-04-19 . pubchem.ncbi.nlm.nih.gov . en.
  3. 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 . en . 31 . 11 . 2552–2560 . 10.1002/pat.4982 . 225739893 . 1042-7147.
  4. 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.
  5. US. 3351574. Castor oil polyglycidyl ether. 1967-11-07. Hicks. Darrel D.. Belanger. William J.. Celanese Coatings Co..
  6. Ramon . Eric . Sguazzo . Carmen . Moreira . Pedro M. G. P. . A Review of Recent Research on Bio-Based Epoxy Systems for Engineering Applications and Potentialities in the Aviation Sector . Aerospace . en . 5 . 4 . 110 . October 2018. 10.3390/aerospace5040110 . 2018Aeros...5..110R . 2226-4310. free .
  7. WO. application. 2019238867. 2019-12-19. Herbicidal formulations comprising glyphosate and cote-based adjuvants. Nouryon Chemicals International BV. Bevinakatti. Hanamanthsa. Islam. Mojahedul.
  8. Web site: Zarnitz . Charles . Flexibilizing modifiers . CVC Thermosets.
  9. WO. 2015095994. 2015-07-02. Epoxy resin composition. Dow Global Technologies LLC. Shen. Yue. Zhan. Fu. Wu. Yan. Drumright. Ray E.. application.
  10. 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 . 10.1080/01694243.2018.1517488 . 105550538 . 0169-4243.
  11. Web site: 14228-73-0 CAS DataBase . 2022-04-11 . www.chemicalbook.com . 2022-04-11 . https://web.archive.org/web/20220411203519/https://www.chemicalbook.com/CASEN_14228-73-0.htm . live .
  12. Sathyaraj . S. . Sekar . K. . 2021 . Recent Advances in Bio-Based Sustainable Aliphatic and Aromatic Epoxy Resins for Composite Applications . Key Engineering Materials . en . 882 . 121–131 . 10.4028/www.scientific.net/KEM.882.121 . 233301700 . 1662-9795.
  13. US. 8062468. 2011-11-22. Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins. Sika Technology AG. Finter. Jürgen. Kramer. Andreas. Schulenburg. Jan Olaf. Rheinegger. Urs.
  14. Santiago . David . Guzmán . Dailyn . Ferrando . Francesc . Serra . Àngels . De la Flor . Silvia . March 2020 . Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol . Polymers . en . 12 . 3 . 542 . 10.3390/polym12030542 . 2073-4360 . 7182903 . 32131508. free .
  15. 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.
  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. Mashouf Roudsari . Ghodsieh . Mohanty . Amar K. . Misra . Manjusri . 2017-11-06 . Green Approaches To Engineer Tough Biobased Epoxies: A Review . ACS Sustainable Chemistry & Engineering . en . 5 . 11 . 9528–9541 . 10.1021/acssuschemeng.7b01422 . 2168-0485. free .
  18. 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 . 10.1680/jgrma.20.00085 . 233687152 . 2049-1220.
  19. application. US. 2010326660. 2010-12-30. Use of direct epoxy emulsions for wellbore stabilization. M-I LLC. Ballard. David Antony. Burn. Andrew., since abandoned.

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