Products obtained by acid clay catalyzed dimerization of oleic, elaidic, and tall oil fatty acids were characterized. The monomeric products (35% of total) consisted of stearic, octadecenoic (66% trans-), and mid chain monomethyl branched acids, both saturated and unsaturated. The polymeric products (65% of total) consisted of linear, alicyclic, aromatic, and polycyclic dimers. The tall oil fatty acid based dimer closely resembled oleic dimer in polycyclic character and linoleic dimer in aromatic and linear structures. Oleic dimers contained the highest linear structural content, while linoleic dimer contained the largest polycyclic content. Alicyclic structures were the principal components of all three products. The monocyclic dimer structures present consisted of six membered ring systems with linoleic and tall oil fatty acid dimers containing the highest aromatic contents.
Menthanyl acetate is a commercial product used in the formulation of fragrances. This material and its precursor, p‐menthanol, were each found to be mainly mixtures of four isomers. The use of preparative GC and 1H‐NMR spectroscopy proved invaluable in distinguishing the isomers of the p‐menthanols and p‐menthanyl acetates. This work identifies each isomer and corrects spectroscopic assignments previously reported in the literature. 1H‐NMR distinguished isomers with axial and equatorial methyl and hydroxyl groups on a cyclohexane ring.
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