Fatty Alkanolamides Research Articles

Kinetics in the thermal and catalytic amidation of C18 fatty acids with ethanolamine for the production of pharmaceuticals

For the first time, in this work, C18 fatty acid amidation with equimolar amounts of ethanolamine was studied both in the absence and presence of heterogeneous catalysts in hexane as a solvent at 180 °C. The products, saturated, and especially unsaturated fatty alkanol amides, which exhibit endocannabinoid activities, have been conventionally prepared using toxic and corrosive homogeneous catalysts. The results revealed that noncatalytic thermal amidation of stearic acid proceeding much faster for stearic than for oleic or linoleic acids. Furthermore, microporous H-Beta-150 was the most active catalyst. Mesoporous, H-MCM-41 with lower acidity was also active in oleic acid amidation, whereas more acidic, mesoporous H-MCM-36 gave lower yield due to formation of esteramides.

Direct synthesis of fatty acid alkanolamides and fatty acid alkyl esters from high free fatty acid containing triglycerides as lubricity improvers using heterogeneous catalyst

Direct one-step aminolysis of high free fatty acid containing triglycerides of used cotton seed oil, karanja oil and jatropha oil was investigated using a new heterogeneous catalyst. The catalyst, 2.5-NaOH/CaO, was prepared in nanocrystalline form by using simple wet chemical method. Complete conversion of used cotton seed oil (99%) to fatty alkanolamides has been obtained in 45min with the prepared catalyst when 5wt% of catalyst amount and 6:1M ratio of diethanolamine/oil were used. The catalyst was equally active for the transesterification reaction of similar feed stocks. The prepared fatty acid alkanolamides was found to improve lubricity of diesel fuel significantly.

Pharmaceuticals and Surfactants from Alga-Derived Feedstock: Amidation of Fatty Acids and Their Derivatives with Amino Alcohols.

Amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, was demonstrated with zeolites and mesoporous materials as catalysts and ethanolamine, alaninol, and leucinol. The last two can be derived from amino acids present in alga. The main products were fatty alkanol amides and the corresponding ester amines, as confirmed by NMR and IR spectroscopy. Thermal amidation of technical-grade oleic acid and stearic acid at 180 °C with ethanolamine were non-negligible; both gave 61% conversion. In the amidation of stearic acid with ethanolamine, the conversion over H-Beta-150 was 80% after 3 h, whereas only 63% conversion was achieved for oleic acid; this shows that a microporous catalyst is not suitable for this acid and exhibits a wrinkled conformation. The highest selectivity to stearoyl ethanolamide of 92% was achieved with mildly acidic H-MCM-41 at 70% conversion in 3 h at 180 °C. Highly acidic catalysts favored the formation of the ester amine, whereas the amide was obtained with a catalyst that exhibited an optimum acidity. The conversion levels achieved with different fatty acids in the range C12-C18 were similar; this shows that the fatty acid length does not affect the amidation rate. The amidation of methyl palmitate and biodiesel gave low conversions over an acidic catalyst, which suggested that the reaction mechanism in the amidation of esters was different.

Lipase-catalyzed chemoselective aminolysis of various aminoalcohols with fatty acids

Candida antarctica lipase is well known to convert amines and alcohols into amides and esters. This report describes the development of a solvent-free enzymatic process for the production of fatty alkanolamides. The aminolysis of linoleyl ethyl ester with several aminoalcohols from C2 to C6 (linear or branched compounds), and the very high selectivity of amide compounds have been observed. Our investigation leads us to develop an original biotechnological process for the chemoselective synthesis of new active molecules for cutaneous application.

Solvent‐free enzymatic synthesis of fatty alkanolamides

An environmentally benign and volume efficient process for enzymatic production of alkanolamides is described. Immobilized Candida antarctica lipase B, Novozym435, was used to catalyze the condensation of lauric acid with monoethanolamine. The reaction temperature of 90 degrees C was required to keep the reactants in a liquid state. Stepwise addition of the amine minimized problems caused by the formation of a highly viscous amine/fatty acid ion-pair. The enzyme was both very active and stable under the reaction conditions, with about half of the activity remaining after 2 weeks. The maximum amide yield obtained when using equimolar amounts of the reactants was 75%, which could be increased to 95% upon water removal. Special precautions to avoid co-distillation of the amine were required. Two different strategies to avoid the amine loss are presented.

A novel technique for the preparation of secondary fatty amides

AbstractA low‐temperature synthesis of fatty alkanolamides, fatty diamides and fatty aralkylamides directly from triglycerides and primary amines provides essentially quantitative yields of the various products. The reactions run to completion in 3–12 h at temperatures of 50–60°C, approximately 100°C lower than employed in present conventional practice. The amines are used in excess and serve as solvent, reagent and, perhaps, as catalyst. The amides were characterized by melting point and spectroscopic (infrared and nuclear magnetic resonance) methods. If the mixed amides produced from the various natural triglyceride mixtures of fats and oils are acceptable products, this synthetic method provides these products in satisfactory quality while conserving energy and avoiding the intermediate production of free fatty acids or their esters.

Methyl esters in the fatty acid industry

AbstractMethyl esters, derived from natural fats or oils, can be used as alternatives to fatty acids in the production of a number of derivatives. The derivatives that can be made from methyl esters include fatty alkanolamides, fatty alcohols, isopropyl esters, and sucrose polyesters. By using methyl esters as the raw materials, several benefits may be realized, such as, the ability to make higher purity finished products, the use of milder conditions during syntheses, and the need for less expensive materials of construction. In addition to the applications mentioned, methyl esters are being used increasingly in fractional distillations because they have lower boiling points and are less corrosive than fatty acids.

Soap‐based detergent formulations: IX. α‐sulfo fatty alkanolamides as lime soap dispersing agents

Abstractα‐Sulfo fatty alkanolamides were prepared by sodium methylate catalyzed reactions of methyl α‐sulfo fatty esters with alkanolamines, such as ethanolamine, N‐methyl‐2‐hydroxyethylamine, diethanolamine, 3‐hydroxypropylamine, 2‐hydroxypropylamine, and diglycolamine. Pure compounds, such as α‐sulfo palmitamides and stearamides, as well as the α‐sulfo tallow amides, were prepared and evaluated as surface‐active agents. The α‐sulfo fatty alkanolamides were found to have excellent stability to alkali. Their stability to acid ranged from excellent in the case of α‐sulfo diglycolamides to poor in the case of α‐sulfo diethanolamides. Poor stability to acid was related to ease of conversion to ester‐amines. Washing tests on standard soil cloths showed that the compounds were good detergents by themselves and were also effective in combination with soap and silicates. Their lime soap dispersant requirements ranged from 7–10.