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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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

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

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