Synthesis of β-Amino Alcohols from Terminal Epoxy Fatty Acid Methyl Ester

Abstract

Fats and oils are renewable feedstock that can be treated chemically or enzymatically to derive materials that often act as a replacement for petroleum-derived materials. Long-chain fatty epoxides can be transformed to several chemical derivatives. There has been increasing interest in using these substances as intermediates in the production of new biobased industrial materials. In the present work, renewable methyl 10,11-epoxyundecanoate were reacted with various cyclic, aliphatic, and aromatic amines in the presence of zinc(II) perchlorate hexahydrate as a Lewis acid catalyst under solvent-free conditions, to derive several new β-amino alcohols in a regioselective manner.

Curing of epoxidized linseed oil: Investigation of the curing reaction with different hardener types

“…An important parameter is the degree of unsaturation of the vegetable oil, which is measured by the iodine number. In correlation with this value, linseed oil is one of the most common drying oils with a high iodine number of 130 due to its high content of oleic, linoleic and linolenic acid 2,12–18 …”

From Epoxidized Linseed Oil to Bioresin: An Overall Approach of Epoxy/Anhydride Cross‐Linking

“…Important parameters of functional vegetal oils are the degree of unsaturation, their stereochemistry, also the lengths of the fatty acids. [14] The average degree of unsaturation is measured by the iodine number.I nc orrelation with this value, linseed oil is ad rying oil [11] (iodine number > 130) largely composed of linolenic acids (all-cis-9,12,15-octadecatrienoic acid and all-cis-9,12-octadecadienoic acid (linoleic acid)). [15] To enhancet he potential applications of these monomers, severalc hemical modifications have been realized to functionalize them for furtherp olymerization.…”

Ruthenium‐ and Rhodium‐Catalyzed Strain‐Driven Cleavage and Reconstruction of the C–C Bond

“…Some fatty acids are saturated and some are unsaturated, with one or more double bonds. Important parameters of functional vegetal oils are the degree of unsaturation, their stereochemistry, also the lengths of the fatty acids 14. The average degree of unsaturation is measured by the iodine number.…”