Soybean Oil Fatty Acid Ester Estolides as Potential Plasticizers

Lucas J. Stolp, Patrick J. Gronlund, Dharma R. Kodali

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Fatty acid ester estolides were synthesized from soybean oil and evaluated for plasticizer functionality in poly(vinyl chloride) (PVC). The plasticization ability of the fatty acid ester estolides depends upon the molecular features such as polarity, molecular weight, and branching. The structure of the fatty acid derivatives was modified at the ester head group with various alcohols and the estolide branch was created at the site of unsaturation. Soy fatty acid esters of methanol, iso-butanol, 2-ethylhexanol, and glycerol were prepared to vary the size and polarity at the ester head group. Estolides of these fatty acid esters were prepared using two synthetic routes. In the first route, the fatty acid ester was condensed with an aliphatic acid at the site of unsaturation in the presence of a strong mineral acid. In the second route, the fatty acid ester double bonds were converted to epoxy groups, which were ring opened and acetylated to form acetate estolides. The first synthetic route resulted in low-average estolide content per fatty acid chain while the second route resulted in a higher estolide content per fatty acid chain. The fatty acid ester estolides compounded with PVC showed good plasticizer properties as evidenced by the rheological properties and reduction in glass transition temperature. The fatty acid ester estolides with a higher estolide content had better plasticizer functionality, comparable to commercial controls.

Original languageEnglish (US)
Pages (from-to)727-738
Number of pages12
JournalJAOCS, Journal of the American Oil Chemists' Society
Volume96
Issue number6
DOIs
StatePublished - Jan 1 2019

Bibliographical note

Funding Information:
The authors would like to thank the United Soybean Board for funding this research study. We would also like to thank Aspen Research for use of their compounding and testing equipment as well as supplying formulated poly(vinyl chloride) for the study.

Funding Information:
Acknowledgments The authors would like to thank the United Soybean Board for funding this research study. We would also like to thank Aspen Research for use of their compounding and testing equipment as well as supplying formulated poly(vinyl chloride) for the study.

Publisher Copyright:
© 2019 AOCS

Keywords

  • Estolide
  • Fatty acid esters
  • Plasticizer
  • Poly(vinyl chloride)
  • PVC
  • Soybean oil

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