Diels‐alder adducts from safflower oil fatty acids: I. Maleic anhydride as dienophile

Abstract

The Diels-Alder reaction between alkali conjugated and elaidinized safflower oil fatty acids and maleic anhydride was studied under various experimental conditions. The principal product which was obtained in 51-55% yields was a mixture of the adduct of maleic anhydride and maleic acid in 40:60 proportions. The isolation and properties of this mixed adducts from the reaction mixture and their conversion to trimethyl, tributyl and triallyl esters are described. The trimethyl ester was also obtained in good yield from the methyl esters of the fatty acids and dimethyl maleate.

Self‐emulsifying binders for water‐borne coatings—Synthesis and characteristics of maleated alkyd resins

“…Maleation of TOFA was carried out separately. The reaction of maleic anhydride with unsaturated fatty acids is well known 16, 19–21. With conjugated cis‐ double bonds, maleic anhydride reaction mechanism is Diels‐Alder type, which proceeds exothermically.…”

“…With conjugated cis‐ double bonds, maleic anhydride reaction mechanism is Diels‐Alder type, which proceeds exothermically. With isolated double bonds, higher temperatures are needed and reaction of maleic anhydride occurs at the allylic position via ene‐reaction, forming a substituted succinic anhydride derivative (Schemes and ) 16–21…”

Thermally Reversible Polymeric Networks from Vegetable Oils

“…Safflower oil was isomerized to arrange the C-C double bonds into conjugated configuration and used in DA reactions, in earlier works dating back to 1971 and 1972 [27][28][29]. Esters of the modified oil were successfully reacted with maleic anhydride, styrene, and acrylic acid as dienophiles [27][28][29]. Another interesting raw material is tung oil, which naturally contains conjugated trienes.…”

Properties of Thermosets Derived from Chemically Modified Triglycerides and Bio-Based Comonomers

“…As itaconic acid is readily derived from carbohydrates via fungal fermentation, it has been successfully used in a variety of polymer applications [14]. These include as a dienophile for Diels-Alder chemistry in modification of fatty acids [15], grafting of polyitaconic acid onto other polymers [16], and incorporation into epoxy resins [17]. We also studied ethyl cinnamate ( Figure 1C) as a lignin model compound, to determine whether the cinnamyl moieties found in native or isolated lignins (and potentially in bio-oils as well) are reactive with AESO.…”