Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Abstract

SUMMARY:The highly strained ring in epoxides makes these compounds very versatile intermediates. Epoxidized vegetable oils are gaining a lot of attention as renewable and environmentally friendly feedstock with various industrial applications such as plasticizers, lubricant base oils, surfactants, etc. Numerous papers have been published on the development of the epoxidation methods and the number is still growing. This review reports the synthetic approaches and applications of epoxidized vegetable oils. KEYWORDS: Epoxidation; Renewable feedstock; Unsaturated fatty acids; Vegetable Oils RESUMEN:Modificación del doble enlace olefínico en ácidos grasos insaturados y en derivados de aceites vegetales via epoxidación: Revisión. La alta tensión del anillo en los epóxidos hace que estos compuestos intermediarios sean muy versátiles. Los aceites vegetales epoxidados están ganando mucha atención como materia prima renovable y respetuosa con el medio ambiente con diversas aplicaciones industriales, tales como plastificantes, aceites base para lubricantes, tensioactivos, etc. Por esta razón, se han publicado numerosos trabajos sobre el desarrollo de métodos de epoxidación y el número todavía es creciente. Esta revisión aporta información sobre enfoques sintéticos y aplicaciones de aceites vegetales epoxidados.

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

“…The carbon–oxygen (C─O) stretching peak appeared at 1169–1172 cm −1 . The ester carbon–hydrogen (C─H) stretching and bending vibrations were observed at 2853–2923 and 1461–1463 cm −1 …”

“…The DFAEs—dihexyl, di‐(2ethylhexyl) and dioctyl dimerate—were obtained using reaction conditions as previously reported . In general, a mixture of dimer acid (114.0 g, 0.2 mol), alcohol (0.9 mol), and molecular sieve (17.2 g, 15 wt%) were transferred into a single neck 500 mL round bottom flask.…”

“…Various green technologies for esterification have been investigated including self‐esterification, heterogeneous catalysis, and enzymatic reactions, and there are several previous studies highlighting solvent‐free esterification for biolubricant production . However, to the best of our knowledge, most of DFAEs are produced by esterification of dimer acid and alcohol catalyzed by organic acid such as p ‐toluenesulfonic acid, or dimerization of methyl ester of fatty acids . In order to investigate the performance of DFAE as a biolubricant, in the present study, we extended our previous study to produce DFAE by catalyst‐ and solvent‐free esterification which was then compared to tin‐catalyzed esterification.…”

Oleochemicals from Palm Oil for the Petroleum Industry

“…A cost-effective and sustainable supply of energy sources is of enormous importance to the economy and national security. Oleochemicals are chemicals derived from sustainable resources that are majorly oils and fats of vegetable and animal origin [1]. These resources are widely available or can be easily cultivated (virgin vegetable oils) or cheaply sourced (waste vegetable oils and animal fat) in virtually all parts of the world.…”

“…Basic oleochemicals include fatty acids, methyl esters, fatty alcohols of these fatty acids and glycerol [1,5] as well as fatty amines [6]. With a better understanding of oleochemistry, researchers now variously functionalize triglycerides in vegetable oils to manufacture different useful products [7].…”