Enzymatic Synthesis of Fatty Hydroxamic Acid Derivatives Based on Palm Kernel Oil

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%.

A novel hydroxamic acid-containing antibiotic produced by a Saharan soil-livingStreptomycesstrain

“…; Jahangirian et al . ). Among their numerous properties, hydroxamic acids and derivatives have been largely reported as effective antibacterial and antifungal agents (Li et al .…”

“…Hydroxamic acids (bearing the functional group Nhydroxy amide) are one such interesting class of molecule produced by many Streptomyces species (Dimkpa et al 2008;Kodani et al 2013). Their low toxicities in general, their weak acid properties and their ability for complexing transition metal ions have resulted in these molecules receiving considerable attention for broad therapeutic and industrial applications (Vanjari and Pande 2003;Rho et al 2006;Jahangirian et al 2011). Among their numerous properties, hydroxamic acids and derivatives have been largely reported as effective antibacterial and antifungal agents (Li et al 2003;Pepeljnjak et al 2005).…”

Benzyl and Methyl Fatty Hydroxamic Acids Based on Palm Kernel Oil as Chelating Agent for Liquid-Liquid Iron(III) Extraction

“…The molecular weight of MFHAs and BFHAs were 264 and 358 g/mol, respectively as determined from elemental analysis data as reported earlier [20]. …”

Copper Extraction by Fatty Hydroxamic Acids Derivatives Synthesized Based on Palm Kernel Oil

“…PFHAs, MFHAs, IPFHAs and BFHAs were separately synthesized from palm kernel oil according to the method reported recently by our group 15,16 .…”

“…This is the fi rst report for using those fatty hydroxamic acids derivatives as chelating agents. The synthesis of PFHAs, MFHAs, IPFHAs and BFHAs are simple, environmental friendly and using easily available palm kernel oil raw material 15,16 .…”