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

Hossein Jahangirian,Mazyar Peyda,Yadollah Gharayebi,Sidik Silong,Md Jelas Haron,Nor Azah Yusof,Roshanak Rafiee-Moghaddam,Anuar Kassim

doi:10.3390/molecules16086634

Hossein Jahangirian, Mazyar Peyda + Show 6 more

Open Access

https://doi.org/10.3390/molecules16086634

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Abstract

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%.

Highlights

Hydroxamic acids and their derivatives with the general formula R–CO–NHOH and R–CO–NR′OH have wide applications due to their biological activities and chelating properties
We have investigated the synthesis of the phenyl fatty hydroxamic acids (PFHAs) as the first derivative of fatty hydroxamic acids [19]
Results of elemental analysis showed that the nitrogen content in the methyl fatty hydroxamic acids (MFHAs), isopropyl fatty hydroxamic acids (IPFHAs) and benzyl fatty hydroxamic acids (BFHAs) synthesized from the palm kernel oil were 5.31, 4.62 and 3.91% respectively

Summary

Introduction

Hydroxamic acids and their derivatives with the general formula R–CO–NHOH and R–CO–NR′OH have wide applications due to their biological activities and chelating properties. The synthesis of fatty hydroxamic acids (FHAs) from canola oil and hydroxylamine has been reported by our group [18] In this investigation the reaction was carried out in biphasic medium in the present of lipozyme as immobilized enzyme, for optimization of the reaction we investigated the effect of changing of reaction conditions such as types of organic solvent, pH, amount of enzyme, mol ratio of reactants and reaction time on the reaction. We have investigated the synthesis of the phenyl fatty hydroxamic acids (PFHAs) as the first derivative of fatty hydroxamic acids [19] In this synthesis, phenyl hydroxylaminolysis of canola or palm kernel oils were carried out in biphasic organic/aqueous medium using lipozyme as catalyst. The reactions were catalyzed by an immobilized lipase catalysts, it include all the advantages of enzymatic reactions such as high selectivity, good saving in energy, mild reaction conditions and environmental friendliness

Synthesis

Effect of Mol Ratio of Reactants

Elemental analysis

Materials

Characterization

Conclusions