Abstract: A method of isomerizing methyl 9-decenoate in a reaction mixture, and forming methyl 8-decenoate, and reacting the methyl 8-decenoate by metathesis to form 1,16-dimethyl 8-hexadecenedioate, and hydrogenating 1,16-dimethyl 8-hexadecenedioate to form 1,16-dimethyl hexadecanedioate. In some embodiments, the 1,16-dimethyl hexadecanedioate can be converted to hexadecanedioic acid.

Abstract: Methods of making polyamides from renewable materials, such as natural oils, are generally disclosed herein. In some embodiments, the polyamides are nylon-10. In some such embodiments, nylon-10 is made by polymerizing 10-aminodecanoic acid, or esters thereof. In some further such embodiments, the 10-aminodecanoic acid monomers (or esters thereof) are derived from natural oils via the metathesis of unsaturated fatty acid moieties of the natural oil.

Abstract: Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

Abstract: A method of isomerizing a substance includes combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture. The method may be used to functionalize a substance, as the substance including a 2-alkenyl group can be reacted with a functionalizing agent to form a substance including a first functional group. The methods may be used to form a dicarboxylic acid, such as suberic acid, from a renewable feedstock.

Abstract: A method of isomerizing a substance includes combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture. The method may be used to functionalize a substance, as the substance including a 2-alkenyl group can be reacted with a functionalizing agent to form a substance including a first functional group. The methods may be used to form a dicarboxylic acid, such as suberic acid, from a renewable feedstock.