Fatty Hydroxamic Acids Research Articles

KAJIAN SINTESIS ASAM LEMAK HIDROKSAMAT MENGGUNAKAN MINYAK GORENG BEKAS

Fatty Hydroxamic Acids (FHA) has been successfully synthesized from used cooking oil. The purpose of this research was the enzymatic synthesis of fatty hydroxamic acids from used cooking oil and determine the optimum conditions, which includes three stages of processing, namely the oil preparation stage, the synthesis optimization stage and the characterization stage. At the oil preparation stage, the yield of used cooking oil was 29%. At the optimization stage, the optimum conditions for the synthesis of fatty hydroxamic acids from used cooking oil were at a temperature of 35oC for 25 hours with a ratio of lipase (gram) : hydroxylamine (mmol) equal to 1:500 and the ratio of lipase (gram) : crude bran rice (gram) was equal to 1:75. The number of hydroxamic acid groups in 1 gram of dry sample of fatty hydroxamic acid was 3,16 mmol. Based on the results of the analysis of the color test with Cu (II) and Fe (III), a complex color that is typical for the two metals which obtained with fatty hydroxamic acids, they were green and dark red. Whereas, from the FTIR analysis, the spectrum of the functional groups of hydroxamic acid was obtained.

Separation of N-Methylhydroxamic Fatty Acids Based on Ketapang Seed Oil using High Performance Liquid Chromatography

N-methyl fatty hydroxamic acids (N-MFHAs) is a derivative of a hydroxamic acid (FHA), were synthesized from ketapang seed oil (Terminalia catappa L.) with N-methyl hydroxylamine enzymatically using immobilized lipase (Lipozyme TL IM). N-MFHAs that are synthesized are still in a mixed state of triglycerides of the ketapang seed oil. This research aims to determine the optimum conditions for the separation of N-MFHAs into their single components and their percentage composition using High Performance Liquid Chromatography (HPLC). The specification of the HPLC system includes using the reverse phase column SGE C-18 ODS-2 and UV detector 213 nm. The optimum conditions for the separation of N-MFHAs in the HPLC system include using the mobile phase of methanol 100% and flow rate of 0.25 mL/minutes with an injection volume of 20 µL and sample concentration of 10.000 ppm. The percentage of the N-MFHAs composition successfully separated using HPLC were linoleoyl-methyl-fatty hydroxamic acid (13.09%), oleoyl-methyl-fatty hydroxamic acid (62.46%), palmitoyl-methyl-fatty hydroxamic acid (19.51%), and stearoyl-methyl-fatty hydroxamic acid (4.93%).

Kajian Kemampuan Adsorpsi Zeolit Alam Terimpregnasi Asam Lemak Hidroksamat sebagai Agen Pengkelat Ion Logam Tembaga

One of the way to recycle heavy metals in the prevention of environmental pollution is by using a solid-liquid extraction method through the impregnation mechanism of chelating agent in the adsorbent to increase its ability to bind heavy metal ions. In this study, the impregnation of fatty hydroxamic acids (FHA) successfully carried out on active natural zeolite (ZAA). This is has been done to increase the maximum adsorption capacity of ZAA towards heavy metals. The purpose of this study was to examine the adsorption ability of FHA impregnated onto ZAA as a chelating agent in copper metal ions by using column chromatography. This column contains FHA, which synthesized from crude rice bran oil and impregnated onto ZAA. There are several parameters were investigated, they are, the effect of FHA concentration, mass of FHA-ZAA resin and pH of the metal ion sample. From this study, the concentration of FHA impregnated on the zeolite surface reached 41.60%. The optimum conditions for Cu(II) adsorption by FHA-ZAA were as follows: mass ratio of FHA-ZAA resin with Cu(II) concentration (g : ppm) was 1:100 and the optimum condition of Cu(II) ion was at pH 5

Synthesis of Fatty Hydroxamic Acids (FHAs) from Coconut Oil Using Lipase as a Catalyst

Fatty hydroxamic acids (FHAs) have been successfully synthesized from coconut oil by a one-step lipase catalyzed reaction. FHAs are the acids that are based on fatty acids. Their hydrophobicity can be use for some applications such as surfactant and metal ions extraction from aqueous media. This paper describes enzymatic synthesis of FHAs from coconut oil by reacting hydroxylamine with the substrate catalyzed by a lipase. The lipase used was Lipozyme, a commercially lipase of Mucor meihe fixed on a polymer anion exchange resin. The use of immobilized lipase as the catalyst for the preparation reaction provides an easy isolation of the enzyme from the products and other components in the reaction mixture. In addition, it also allows the reaction to be carried out under mild conditions, which reduces the reaction’s side products. The optimum preparation conditions obtained were as follows; the reaction temperature was 30oC, the reaction time was 30 h, the ratio of coconut oil: lipozyme (g:g) was 29.5, and the ratio of hydroxylamine: coconut oil (mmol:mmol) was 6. The solvent used was hexane. The purified products were characterized by qualitative test, such as FTIR spectroscopy and HPLC.

Synthesis of Fatty Hydroxamic Acids (FHAs) from Coconut Oil Using Lipase as a Catalyst

Fatty hydroxamic acids (FHAs) have been successfully synthesized from coconut oil by a one-step lipase catalyzed reaction. FHAs are the acids that are based on fatty acids. Their hydrophobicity can be use for some applications such as surfactant and metal ions extraction from aqueous media. This paper describes enzymatic synthesis of FHAs from coconut oil by reacting hydroxylamine with the substrate catalyzed by a lipase. The lipase used was Lipozyme, a commercially lipase of Mucor meihe fixed on a polymer anion exchange resin. The use of immobilized lipase as the catalyst for the preparation reaction provides an easy isolation of the enzyme from the products and other components in the reaction mixture. In addition, it also allows the reaction to be carried out under mild conditions, which reduces the reaction’s side products. The optimum preparation conditions obtained were as follows; the reaction temperature was 30oC, the reaction time was 30 h, the ratio of coconut oil: lipozyme (g:g) was 29.5, and the ratio of hydroxylamine: coconut oil (mmol:mmol) was 6. The solvent used was hexane. The purified products were characterized by qualitative test, such as FTIR spectroscopy and HPLC.

Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase.

N-methyl fatty hydroxamic acid (N-MFHA), which is a derivative of hydroxamic acid (HA), was synthesized from ketapang seed oil (Terminalia catappa L.). In general, HAs have wide applications due to their chelating properties and biological activities. N-MFHAs were synthesized using immobilized lipase (Lipozyme TL IM) in biphasic medium which was the ketapang seed oil dissolved in hexane and N-methylhydroxylamine dissolved in water. The products were characterized through color testing and FT-IR spectroscopy after purification. Various factors affecting the enzyme activity investigated in the study included the effect of incubation time, the amount of lipase used, and the temperature. On the basis of the results, the optimum conditions for the synthesis of N-MFHA obtained are 25 h of incubation time, a temperature of 40 °C, and a ratio of 1:100 for the amount of enzyme (g)/oil (g). At the optimum conditions of the reaction, 59.7% of the oils were converted to N-MFHA.

Removal of Cu(II) ions from aqueous solution by fatty hydroxamic acids immobilized onto bentonite

The mining business in Indonesia has a large contribution to economic growth and the supplies of domestic minerals. However, if the mining businessis conducted illegally and does not use the good mining practice, it will not only harm the country but also risk endangering human safety due to environmental damage caused. In gold mining process, only the main metal, that is gold, is taken while the other metal is discharged into the sewer as waste.One of the metal ions to be waste is copper ion, Cu(II) ion. In this study, removal of Cu(II) ions from illegal gold mining waste was carried out using fatty hydroxamic acids (FHA) immobilized onto bentonite.The FHA used is enzymatically synthesized from Jatropha curcas L. kernel oil. The effects of Cu(II) ion pH and FHA concentration on copper removal have been investigated.The presented results indicated that the extraction of Cu(II) ion was very sensitive to the copper ion pH and extractant concentration. The optimum pH of Cu(II) ion adsorption by FHA-Bentonite (FHA-Bent) is pH 5.A quantitative recovery of Cu(II) ion from FHA-Bent was obtained using 10% HNO3 solutions as eluent with a pre-concentration factorupto 60.

Analisis Pembuatan Asam Lemak Hidroksamat Dari Minyak Kelapa Melalui Metode Enzimatis

Generally, fatty hydroxamic acids (FHA) are synthesized from basic ingredients containing fatty acids.Fatty acids can be obtained from coconut oil among several other sources. Coconut oil contains fatty acids with medium and long chains so it has enormous potential as a raw material for the synthesis of hydroxamic fatty acids. The purpose of this research is to synthesize FHA from coconut oil enzymatically and determine the amount of FHA products produced. The method used is the enzymatic method which includes several stages of work, namely the synthesis stage, the multiplication stage, and the purification stage. From the research results, the percentage obtained from the synthesis was around 48.58% of hydroxamic fatty acids from coconut oil after propagation using the synthesis conditions.The number of hydroxamic acid groups in 1 gram of dry hydroxamic fatty acid sample was 2.97 mmol. Thus, from the two results mentioned above, it was concluded that hydroxamic fatty acids can be synthesized from coconut oil

Analisis Pembuatan Asam Lemak Hidroksamat Dari Minyak Kelapa Melalui Metode Enzimatis

Generally, fatty hydroxamic acids (FHA) are synthesized from basic ingredients containing fatty acids.Fatty acids can be obtained from coconut oil among several other sources. Coconut oil contains fatty acids with medium and long chains so it has enormous potential as a raw material for the synthesis of hydroxamic fatty acids. The purpose of this research is to synthesize FHA from coconut oil enzymatically and determine the amount of FHA products produced. The method used is the enzymatic method which includes several stages of work, namely the synthesis stage, the multiplication stage, and the purification stage. From the research results, the percentage obtained from the synthesis was around 48.58% of hydroxamic fatty acids from coconut oil after propagation using the synthesis conditions.The number of hydroxamic acid groups in 1 gram of dry hydroxamic fatty acid sample was 2.97 mmol. Thus, from the two results mentioned above, it was concluded that hydroxamic fatty acids can be synthesized from coconut oil

Extraction And Pre-Concentration of Zinc(Ii) Ion by Fatty Hydroxamic Acids Immobilized Onto Zeolit

Mining in Indonesia contributes significantly to mineral supplies nationally, but illegal mining activities can cause natural destruction, habitat loss and loss of biodiversity. This is because only the main metal, which is the gold taken while the other metal is discharged into the drain as waste. One of the metal ions to be waste is the zinc(II) ion. A method of zinc(II) ion extraction from other ions by using a column containing fatty hydroxamic acids – loaded zeolit (FHA-Zeo) is described. Several factors, which affect the extraction efficiency such as pH, sample volume, and concentration of eluent and flow rate, have been investigated. The maximum sorption capacity of FHA-zeo obtained was 88.38 mg/g. A quantitative recovery of zinc(II) ion from FHA-zeo column was obtained using 10% HNO3 solutions as eluent with a pre-concentration factor up to 60. A method for separation of zinc(II) from lead(II) is proposed. A rapid sample throughput, a clean separation, a high pre-concentration factor and simplicity are the main advantages in these analytical procedures.

Study on the spectrophotometric detection of free fatty acids in palm oil utilizing enzymatic reactions.

In this paper, a comprehensive study has been made on the detection of free fatty acids (FFAs) in palm oil via an optical technique based on enzymatic aminolysis reactions. FFAs in crude palm oil (CPO) were converted into fatty hydroxamic acids (FHAs) in a biphasic lipid/aqueous medium in the presence of immobilized lipase. The colored compound formed after complexation between FHA and vanadium (V) ion solution was proportional to the FFA content in the CPO samples and was analyzed using a spectrophotometric method. In order to develop a rapid detection system, the parameters involved in the aminolysis process were studied. The utilization of immobilized lipase as catalyst during the aminolysis process offers simplicity in the product isolation and the possibility of conducting the process under extreme reaction conditions. A good agreement was found between the developed method using immobilized Thermomyces lanuginose lipase as catalyst for the aminolysis process and the Malaysian Palm Oil Board (MPOB) standard titration method (R2 = 0.9453).

Antifungal Properties of Phenyl Fatty Hydroxamic Acids and Their Copper Complexes Synthesized Based on Canola and Palm Kernel Oils

Phenyl fatty hydroxamic acids (PFHAs) were synthesized by phenyl hydroxylaminolysis of canola or palm kernel oils using lipozyme TL IM as catalyst. Copper complexes of phenyl fatty hydroxamic acids (copper phenyl fatty hydroxamate (Cu-PFHs)) acids were prepared by stirring the phenyl fatty hydroxamic acids which were dissolved in hexane and copper(II) nitrate solution. The antifungal properties of phenyl fatty hydroxamic acids and its copper(II) complex Cu-PFHs based on canola and palm kernel oils were separately investigated against Candida parapsilosis, Candida albicans and Aspergillus fumigatus by the disc diffusion method using Mueller-Hinton agar. The results showed that antifungal activity of Cu-PFHs is higher than phenyl fatty hydroxamic acids do and also the activity of phenyl fatty hydroxamic acids and Cu-PFHs increase while their concentrations increase. The antifungal activity of phenyl fatty hydroxamic acids and Cu-PFHs are significantly higher than nystatin while use against the A. fumigatus, C. parapsilosis and C. albicans and also are significantly higher than ketoconazole while use against the A. fumigatus.

Sintesis Asam-Asam Lemak Hidroksamik dari Minyak Kelapa Menggunakan Lipase sebagai Katalis

Fatty hydroxamic acids (FHAs) have been successfully synthesized from coconut oil by a one-step lipase catalyzed reaction. FHAs are theacids that are based on fatty acids. Their hydrophobicity can be use for some applications such as surfactant and metal ions extraction fromaqueous media. This paper describes enzymatic synthesis of FHAs from coconut oil by reacting hydroxylamine with the substrate catalyzedby a lipase. The lipase used was Lipozyme, a commercially lipase of Mucor meihe fixed on a polymer anion exchange resin. The use ofimmobilized lipase as the catalyst for the preparation reaction provides an easy isolation of the enzyme from the products and othercomponents in the reaction mixture. In addition, it also allows the reaction to be carried out under mild conditions, which reduces thereaction’s side products. The optimum preparation conditions obtained were as follows; the reaction temperature was 30 oC, the reactiontime was 30 h, the ratio of coconut oil : lipozyme (g : g) was 29.5, and the ratio of hydroxylamine : coconut oil (mmol : mmol) was 6. Thesolvent used was hexane. The purified products were characterized by qualitative test, such as FTIR spectroscopy and HPLC.

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

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).

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

Fatty hydroxamic acids derivatives based on palm kernel oil which are phenyl fatty hydroxamic acids (PFHAs), methyl fatty hydroxamic acids (MFHAs), isopropyl fatty hydroxamic acids (IPFHAs) and benzyl fatty hydroxamic acids (BFHAs) were applied as chelating agent for copper liquid-liquid extraction. The extraction of copper from aqueous solution by MFHAs, PFHAs, BFHAs or IPFHAs were carried out in hexane as an organic phase through the formation of copper methyl fatty hydroxamate (Cu-MFHs), copper phenyl fatty hydroxamate (Cu-PFHs), copper benzyl fatty hydroxamate (Cu-BFHs) and copper isopropyl fatty hydroxamate (Cu-IPFHs). The results showed that the fatty hydroxamic acid derivatives could extract copper at pH 6.2 effectively with high percentage of extraction (the percentages of copper extraction by MFHAs, PFHAs, IPFHs and BFHAs were found to be 99.3, 87.5, 82.3 and 90.2%, respectively). The extracted copper could be quantitatively stripped back into sulphuric acid (3M) aqueous solution. The obtained results showed that the copper recovery percentages from Cu-MFHs, Cu-PFHs, Cu-BFHs and Cu-IPFHs are 99.1, 99.4, 99.6 and 99.9 respectively. The copper extraction was not affected by the presence of a large amount of Mg (II), Ni (II), Al (III), Mn (II) and Co (II) ions in the aqueous solution.

Antibacterial effect of phenyl fatty hydroxamic acids synthesized from canola oil

Phenyl fatty hydroxamic acids (PFHAs) were synthesized in a biphasic organic/aqueous medium from canola oil and phenyl hydroxylamine (PHA). The reaction was carried out in a sealed flask, incubated in water batch shaker at 39°C for 72 h and catalyzed by immobilised lipase (Lipozyme TL IM). The products were then separated by filtration, solvent extraction followed by evaporation of the solvent. Elemental analysis, 1H NMR (hydrogen nuclear magnetic resonance) and FTIR (Fourier transform infrared) spectra showed that PFHAs were produced from the reaction of PHA and canola oil. The antibacterial activity of PFHAs dissolved in hexane were investigated against gram-positive (that is, Staphylococcus aureus) and gram-negative bacteria (that is, Escherichia coli) by the disk and well diffusion methods using Mueller-Hinton Agar (MHA). The results showed that PFHAs have high antibacterial activity and their antibacterial property on E. coli is stronger than on S. aureus. The antibacterial property of PFHAs increased with the increase in PFHAs concentration. Key words: Antibacterial activity, phenyl fatty hydroxamic acids, canola oil, enzymatic reaction.

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 (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%.

Preparation of new polymer nanocomposites based on poly(lactic acid)/fatty nitrogen compounds modified clay by a solution casting process

In this study, different organoclays (OMMTs) were prepared using various fatty nitrogen compounds (FNCs) and natural clay, sodium montmorillonite (MMT). The clay modification was carried out by stirring the clay particles in an aqueous solution of fatty amides (FA), fatty hydroxamic acids (FHA), and carbonyl difatty amides (CDFA). These OMMTs were then used for nanocomposites production to improve the property balance of poly(lactic acid) (PLA) by solution casting process. All sets of OMMTs and nanocomposites were characterized using various apparatuses. In the nanocomposites, where the clay surface is pretreated with FA, FHA and CDFA, the basal spacing of the clay increased to 2.94, 3.26 and 3.80 nm, respectively The X-ray diffraction (XRD) and transmission electron microscopy (TEM) results confirmed the production of nanocomposites. PLA modified clay nanocomposites show higher thermal stability and significant improvement of mechanical properties in comparison with pure PLA.

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

Phenyl fatty hydroxamic acids (PFHAs) were synthesized from canola or palm oils and phenyl hydroxylamine (FHA) catalyzed by Lipozyme TL IM or RM IM. The reaction was carried out by shaking the reaction mixture at 120 rpm. The optimization was carried out by changing the reaction parameters, namely; temperature, organic solvent, amount and kind of enzyme, period of reaction and the mol ratio of reactants. The highest conversion was obtained when the reaction was carried out under the following conditions: temperature, 39°C; solvent, petroleum ether; kind and amount of lipase, 80 mg Lipozyme TL IM/mmol oil; reaction period, 72 h and FHA-oil ratio, 7.3 mmol FHA/ mmol oil. The highest conversion percentage of phenyl hydroxylaminolysis of the Ladan and Kristal brands commercial canola oils, palm stearin and palm kernel oils were 55.6, 52.2, 51.4 and 49.7 %, respectively.

Epoxidized Palm Oil Plasticized Polylactic Acid/Fatty Nitrogen Compound Modified Clay Nanocomposites: Preparation and Characterization

Fatty nitrogen compounds (FNCs); fatty amides (FAs), fatty hydroxamic acids (FHAs), and N,N′-carbonyl difatty amides (CDFAs), which were synthesized from palm oil, have been used as organic compounds to modify a natural clay (sodium montmorillonite). The clay modification was carried out by stirring the clay particles in an aqueous solution of FAs, FHAs, or CDFAs by which the clay layer distance increased from 1.23 to 2.69, 2.89 and 3.21 nm, respectively. The modified clay was then used in the preparation of the epoxidized palm oil (EPO) plasticized polylactic acid (PLA) nanocomposites. The interaction of the modifier in the clay layer was characterized by X-ray diffractometry (XRD) and Fourier transform infrared spectroscopy (FTIR). Elemental analysis was used to estimate the presence of these FNCs in the clay. The nanocomposites were synthesized by solution casting of the modified clay and a PLA/EPO blend at the weight ratio of 80/20, which has the highest elongation at break. The nanocomposites were then characterized using XRD, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and tensile properties measurements. The XRD and TEM results confirmed the production of nanocomposites. PLA/EPO modified clay nanocomposites show higher thermal stability and significant improvement of mechanical properties in comparison with those of the PLA/EPO blend.