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Enzymatic chemoselective synthesis of secondary-amide surfactant from N-methylethanol amine.

Journal of bioscience and bioengineering (2006-02-14)
Jitender Sharma, Daniela Batovska, Yuko Kuwamori, Yasuhisa Asano

Efficient selective synthesis of the secondary amide surfactant N-methyl lauroylethanolamide from methyl laurate and N-methylethanol amine by carrier-fixed Chirazyme L-2 (Candida antarctica) using a kinetic strategy has been demonstrated. When different solvents were screened for product yields using Chirazyme L-2, acetonitrile was found to be optimal. The rate of the reaction increased sharply by increasing the molar ratio of the reactants and the reaction temperature. When the reaction was performed at 50 degrees C for 36 h with 50 mmol ester and 100 mmol amine, the product was obtained in a 97.1% yield. With 50 mmol ester and 150 mmol amine, the highest yield (97.3%) was obtained after 16 h of incubation at 50 degrees C. It took only 5 h to get a yield of 95.8% at 60 degrees C using 50 mmol ester and 200 mmol amine. The enzyme activity in the amidation reaction mixture did not decrease notably even after six uses.

Product Number
Product Description

Methyl laurate, 99.5%
2-(Methylamino)ethanol, ≥98%
Methyl dodecanoate, analytical standard
Methyl laurate, ≥98%, FG
Methyl laurate, certified reference material, TraceCERT®
Methyl laurate, PharmaGrade, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production.

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