Preparation of laurel oil alkanolamide from laurel oil

Abstract

A low-temperature synthesis of laurel oil alkanolamides directly from laurel oil and ethanolamine was carried out in essentially quantitative yields. The ethanolamine/laurel oil molar ratio used was 10:1. Even though amine served as a catalyst in the reaction, we used sodium methoxide at a ratio of 0.2-2% as a second catalyst. The reaction was complete in 1-9 h at room temperature. The identity of the amide was confirmed by IR and 13 C NMR spectroscopy.

Synthesis of Linoleoyl Ethanolamide

“…Linoleoyl esteramine and ethanolamide contents in the crude reaction mixture increased and decreased, respectively with increasing reaction time. Sodium methoxide was an effective catalyst for the amidation reaction and the results agreed well with the previous studies 17,18 . In general, the transesterification reaction between ethanolamine and methyl linoleate will happen and thus result in the formation of esteramine even though the amidation reaction is dominant Fig.…”

“…High linoleoyl ethanolamide content resulting from high conversion of methyl linoleate was probably because ethanolamine was a better solvent to dissolve the reactants and catalyst. In addition, as mentioned above, excess ethanolamine may serve as catalyst and thus promoted the amidation reaction 17 . No significant differences were observed among different solvents after 1 h for linoleoyl esteramine content in the crude reaction mixture.…”

“…In general, fatty acid ethanolamides can be synthesized from ethanolamine with a fatty acyl donor, such as free fatty acids 13 15 , fatty acid chlorides 16 , native oils 17 and fatty acid vinyl esters 18 . In general, using fatty acid chlorides as acyl donor to synthesize fatty acid ethanolamides is more expensive and effective than other acyl donors.…”

“…It has been reported that Novozym 435 lipase is an effective biocatalyst for the amidation reaction between free fatty acids and ethanolamine 14,20 and usually results in a better product s quality in color, yield and odor compared to other methods 21 . In addition, sodium methoxide can also be applied to catalyze the amidation reaction at low or high temperature 15,17 , while the amidation reaction conducted in absence of catalysts needs a higher temperature 2 and usually causes various problems in color and odor even though the addition of deodorizers and antioxidants to the process has been suggested to improve product s quality 21 . The main disadvantage using free fatty acid as acyl donor to synthesize fatty acid ethanolamide is the formation of salt ion-pair from equivalent moles of ethanolamine and free fatty acid 21 .…”

The Effect of Reaction Temperature on Retaining Oxirane Oxygen Contents in the Synthesis of Epoxidized Diethanolamides

“…Lately, secondary fatty amides, such as alkanolamides have been reported to be synthesized by using triacylglycerides from tallow and tripalmitin to react with amine, such as ethanolamine, diethanolamine, ethylenediamine, diethylenediamine and others [2] . Besides, preparation of the ethanolamides by using laurel oil from black olive-sized fruits of Laurus nabilis L. has also been reported [3] . However, alkanolamides can also be used as one type of natural oil derived from polyols to produce rigid polyurethane foam.…”