Enzymatic synthesis of fatty hydroxamic acid derivatives based on palm kernel oil

Fatty hydroxamic acid derivatives were synthesized using Lipozyme TL IM catalyst at biphasic medium as the palm kernel oil was dissolved in hexane and hydroxylamine derivatives were dissolved in water: (1) N-methyl fatty hydroxamic acids (MFHAs); (2) N-isopropyl fatty hydroxamic acids (IPFHAs) and (...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2011-08, Vol.16 (8), p.6634-6644
Main Authors: Jahangirian, Hossein, Haron, Md Jelas, Yusof, Nor Azah, Silong, Sidik, Kassim, Anuar, Rafiee-Moghaddam, Roshanak, Peyda, Mazyar, Gharayebi, Yadollah
Format: Article
Language:English
Subjects:
benzyl fatty hydroxamic acids
Canola
Chemical reactions
Elements
enzymatic reaction
Enzymes
Fatty acids
Fatty Acids - chemical synthesis
Hydroxamic Acids - chemical synthesis
Investigations
isopropyl fatty hydroxamic acids
Lipase - metabolism
lipozyme
methyl fatty hydroxamic acids
palm kernel oil
Palm Oil
Plant Oils - chemistry
Proton Magnetic Resonance Spectroscopy
Solvents
Spectroscopy, Fourier Transform Infrared
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Summary:Fatty hydroxamic acid derivatives were synthesized using Lipozyme TL IM catalyst at biphasic medium as the palm kernel oil was dissolved in hexane and hydroxylamine derivatives were dissolved in water: (1) N-methyl fatty hydroxamic acids (MFHAs); (2) N-isopropyl fatty hydroxamic acids (IPFHAs) and (3) N-benzyl fatty hydroxamic acids (BFHAs) were synthesized by reaction of palm kernel oil and N-methyl hydroxylamine (N-MHA), N-isopropyl hydroxylamine (N-IPHA) and N-benzyl hydroxylamine (N-BHA), respectively. Finally, after separation the products were characterized by color testing, elemental analysis, FT-IR and 1H-NMR spectroscopy. For achieving the highest conversion percentage of product the optimum molar ratio of reactants was obtained by changing the ratio of reactants while other reaction parameters were kept constant. For synthesis of MFHAs the optimum mol ratio of N-MHA/palm kernel oil = 6/1 and the highest conversion was 77.8%, for synthesis of IPFHAs the optimum mol ratio of N-IPHA/palm kernel oil = 7/1 and the highest conversion was 65.4% and for synthesis of BFHAs the optimum mol ratio of N-BHA/palm kernel oil = 7/1 and the highest conversion was 61.7%.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules16086634