The reaction of maleic anhydride with alkenes: a review on the mechanisms involved in the reaction of maleic anhydride with lipids

Abstract

Maleic anhydride is one of the most widely used anhydrides after acetic and phthalic anhydride and its market has grown rapidly over the last century. This compound is a versatile monomer widely used in industrial and commodity chemicals. It is interesting to note that it can be obtained from biosourced molecules such as furfural and 5-hydroxymethylfurfural. The maleinization reaction involves the addition of maleic anhydride molecules to unsaturated compounds, particularly lipids, without the need of solvents. This review article provides a comprehensive overview of the maleinization reaction, focusing on the mechanisms involved in these reaction with lipidic compounds, providing a state-of-the-art overview. The review covers various aspects of the maleinization process, including properties and industrial applications of maleic anhydride, current production methods, experimental setups, and characterization methods for the final products. Different mechanisms involved in the maleinization reaction, such as the Diels-Alder reaction, free radical reaction, and ene reaction, are discussed. The use of additives like catalysts and inhibitors to optimize the reaction is also explored. This review aims to consolidate existing knowledge on maleinization reactions, addressing contradictions in earlier literature and highlighting recent developments. By providing a comprehensive understanding of the maleinization process, this work supports the future development of maleinized compounds for various applications, including biobinders, bioplasticizers, biopolymer synthesis, paints, and coatings.