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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #393820

Research Project: New High-Value Biobased Materials with Applications Across Industry

Location: Bio-oils Research

Title: A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

item Moser, Bryan
item Cermak, Steven - Steve
item Doll, Kenneth - Ken
item Kenar, James - Jim
item Sharma, Brajendra - Bk

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Review Article
Publication Acceptance Date: 6/8/2022
Publication Date: 7/14/2022
Citation: Moser, B.R., Cermak, S.C., Doll, K.M., Kenar, J.A., Sharma, B.K. 2022. A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications. Journal of the American Oil Chemists' Society. 99(10):801-842.

Interpretive Summary:

Technical Abstract: Fatty epoxides are produced from the corresponding alkenes by oxidation in the presence of peracids or other oxidants. The classic method is the Prilezhaev epoxidation in which peracids are generated by in situ oxidation of formic or acetic acids with hydrogen peroxide. Epoxidized vegetable oils and esters are used directly as biobased plasticizers and stabilizers for poly(vinyl chloride) or as important platform chemicals for the oleochemical industry. Nucleophilic attack at the oxirane moiety affords a variety of ring opened monomeric or polymeric products, which in many cases undergo further synthetic modification to yield finished products. The most common nucleophiles include water, alcohols, carboxylic acids, acid anhydrides, and amines, although numerous others can also lead to valuable functionalized fatty derivatives. This review summarizes the chemistry of fatty epoxide ring opening reactions as well as applications of the resultant products. Literature from the last 20 years will be emphasized, although older publications of particular significance will be included. Important applications include biobased lubricants as well as polyols for subsequent production of polyurethanes. In addition, ring-opening reactions hitherto unreported on fatty oxiranes will be suggested to facilitate further advancements in the chemistry and utility of fatty epoxides. Finally, interest in fatty epoxides and their consequent products will continue to grow due to the simplicity, efficiency, and versatility of oxirane formation and ring opening as well as the continued societal transition away from petroleum to a sustainable, circular, low-carbon, and biobased economy.