Enzymatic Synthesis of Phenyl Fatty Hydroxamic Acids from Canola and Palm Oils

Jahangirian, Hossein; Haron, Jelas; Silong, Sidik; Yusof, Nor Azah

doi:10.5650/jos.60.281

Cited by 14 publications

(24 citation statements)

References 20 publications

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“…Fatty hydroxamic acids were synthesised from fatty acids or fatty acid methyl esters and hydroxylamine by using lipase-acyltransferase from Candida Parapsilopsis as catalyst in a biphasic lipid/aqueous medium by Vaysse et al [ 17 ]. Recently 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 also 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.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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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%.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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“…MFHAs and BFHAs were separately synthesized from palm kernel oil and N -methylhydroxylamine hydrochloride, or N -benzyl-hydroxylamine hydrochloride catalyzed by Lipozyme TL IM according to the method reported recently by our group [20,24]. The molecular weight of MFHAs and BFHAs were 264 and 358 g/mol, respectively as determined from elemental analysis data as reported earlier [20].…”

Section: Methodsmentioning

confidence: 99%

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

Haron

Jahangirian

Silong

et al. 2012

IJMS

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Liquid-liquid iron(III) extraction was investigated using benzyl fatty hydroxamic acids (BFHAs) and methyl fatty hydroxamic acids (MFHAs) as chelating agents through the formation of iron(III) methyl fatty hydroxamate (Fe-MFHs) or iron(III) benzyl fatty hydroxamate (Fe-BFHs) in the organic phase. The results obtained under optimized conditions, showed that the chelating agents in hexane extract iron(III) at pH 1.9 were realized effectively with a high percentage of extraction (97.2% and 98.1% for MFHAs and BFHAs, respectively). The presence of a large amount of Mg(II), Ni(II), Al(III), Mn(II) and Co(II) ions did affect the iron(III) extraction. Finally stripping studies for recovering iron(III) from organic phase (Fe-MFHs or Fe-BFHs dissolved in hexane) were carried out at various concentrations of HCl, HNO3 and H2SO4. The results showed that the desired acid for recovery of iron(III) was 5 M HCl and quantitative recovery of iron(III) was achieved from Fe(III)-MFHs and Fe(III)-BFHs solutions in hexane containing 5 mg/L of Fe(III).

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“…There are various methods that have been developed to synthesize hydrazides, either by using chemical methods [11][12][13] or enzymatic methods [14][15][16][17]. Chemical method generally requires multiple steps that start with heating of corresponding oils or esters with hydrazine hydrate in a basic condition for a few hours.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Epoxidized Fatty Hydrazides from Epoxidized Palm Oil Using Native Muchor meihei Lipase in n-Hexane Solvent

Jamingan¹,

Yunus²,

Khim³

et al. 2018

Asian J. Chem.

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Epoxidized fatty hydrazides have been synthesized through an enzymatic catalytic synthesis reaction of epoxidized palm oil with hydrazine monohydrate by native Muchor meihei lipase enzyme in n-hexane solvent. Optimum reaction conditions were studied by observing the yield of epoxidized fatty hydrazides production using several parameters. The highest production of epoxidized fatty hydrazides was obtained when reaction temperature was 50 ºC with an addition of 5 % of enzyme to catalyze the reaction. This were accompanied using stirring speed of 165 rpm under 24 h of reaction. The epoxidized fatty hydrazides was further characterized using Fourier transform infrared spectroscopy, nuclear magnetic resonance spectrometry and CHN elemental analyzer.

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Enzymatic Synthesis of Phenyl Fatty Hydroxamic Acids from Canola and Palm Oils

Cited by 14 publications

References 20 publications

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

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

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

Enzymatic Synthesis of Epoxidized Fatty Hydrazides from Epoxidized Palm Oil Using Native Muchor meihei Lipase in n-Hexane Solvent

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