Reactions of Conjugated Fatty Acids. IV. Diels-Alder Adducts of 9,11-Octadecadienoic Acid¹

Abstract

Adducts of trans,trans-9,11-octadecadienoic acid and dienophiles including nitroethylene, /3-nitrostyrene, acrylic acid, acrylonitrile, acrolein, methacrolein, methyl vinyl ketone, methyl vinyl sulfone, and acetylene carboxylic acid have been prepared. The presence of a six-membered ring in the adducts of acrolein, acrylic acid, and acetylene carboxylic acid was demonstrated by dehydrogenation of the latter adduct and oxidation of the product to trimellitic acid. Hydrogenation of the acrylic acid and the acetylene carboxylic acid adduct gave the same product. Oxidation of the acrolein adduct gave the acrylic acid adduct. The nitroethylene adduct has been shown to exist in two isomeric forms.

Soybean-Derived Biofuels and Home Heating Fuels

“…1 H chemical shifts are reported in units of ppm downfield from TMS (set at 0.0 ppm). 13 C chemical shifts are listed in δ (ppm) relative to chloroform (set at 77.0). Coupling constants, J, are reported in units of Hertz (Hz).…”

“…The acidic compounds found in the recycled soy oil sample are probably attributed to both the temperature and the time period to which these restaurant cooking oils were used, since none of them are found in the newly manufactured soy liquid. [12,13] The recycling and distillation process removed most of the acid components (>99%).…”

Fat‐based dibasic acids

“…Diacid is prepared by the Diels-Alder addition of acrylic acid to a conjugated linoleic acid (36)(37)(38)(39). Ordinary 9,12linoleic acid also undergoes the condensation when conducted under conditions which also isomerize the linoleic acid to mainly 10,12-and 9,11-linoleic acid, which then reacts.…”

Diels‐alder adducts from safflower fatty acids: III. Acrylic and related acid dienophiles

“…Acrylic acid has been studied as a dienophile in the Diels-Alder reaction with some conjugated fatty materials (1)(2)(3)(4)(5). Except for the work of Teeter et al (6) and Kaufman et al (5) on the use of ethyl crotonate, no work of similar nature has been undertaken with acrylic acid, methacrylic acid(2-methyl acrylic acid), crotonic acid (3-methyl acrylic acid), and cinnamic acid(3-phenyl acrylic acid) as dienophiles.…”