Displaying publications 41 - 60 of 170 in total

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  1. Membrane-lytic actions of sulphonated methyl ester surfactants and implications to bactericidal effect and cytotoxicity
    Pan F, Li Z, Gong H, Petkov JT, Lu JR
    J Colloid Interface Sci, 2018 Dec 01;531:18-27.
    PMID: 30015167 DOI: 10.1016/j.jcis.2018.07.031
    Surfactants are multifunctional molecules widely used in personal care and healthcare formulations to cleanse, help disperse active ingredients (e.g., forming emulsions) and stabilise products. With increasing demands on improving biosafety, there is now mounting pressure to understand how different surfactants elicit toxicities at molecular and cellular levels. This work reports the membrane-lytic behaviour of a group of sulphonated methyl ester (SME) surfactants together with representative conventional surfactants. All surfactants displayed the clear rise of lysis of the model lipid bilayer membranes around their CMCs, but the two ionic surfactants SDS and C12TAB even caused measurable lysis below their CMCs, with membrane-lytic actions increasing with monomer concentration. Furthermore, whilst ionic and nonionic surfactants could achieve full membrane lysis once above their CMCs, this ability was weak from the SME surfactants and decreased with increasing the acyl chain length. In contrast to the conventional anionic surfactants such as SDS and SLES, the protein solubilizing capability of the SME surfactants was also low. On the other hand, MTT assays against 3T3 fibroblast cells and human chondrocyte cells revealed high toxicity from SDS and C12TAB against the other surfactants studied, but the difference between SME and the rest of conventional surfactants was small. Similar behaviour was also observed in their bactericidal effect against E. coli and S. aureus. The trend is broadly consistent with their membrane-lytic behaviour, indicating little selectivity in their cytotoxicity and bactericidal action. These results thus reveal different toxicities implicated from different surfactant head groups. Increase in acyl chain length as observed from SME surfactants could help improve surfactant biocompatibility.
    Matched MeSH terms: Esterification
  2. Synthesis of conjugated linoleic acid-rich triacylglycerols by immobilized mutant lipase with excellent capability and recyclability
    Lian W, Li D, Zhang L, Wang W, Faiza M, Tan CP, et al.
    Enzyme Microb Technol, 2018 Oct;117:56-63.
    PMID: 30037552 DOI: 10.1016/j.enzmictec.2018.06.007
    Conjugated linoleic acid (CLA)-rich triacylglycerols (TAG) have received significant attention owing to their health promoting properties. In this study, CLA-rich TAG were successfully synthesized by an immobilized mutant lipase (MAS1-H108A)-catalyzed esterification of CLA-rich fatty acids and glycerol under vacuum. MAS1-H108A was first immobilized onto ECR1030 resin. Results showed that the lipase/support ratio of 41 mg/g was suitable for the immobilization and the thermostability of immobilized MAS1-H108A was greatly enhanced. Subsequently, the immobilized MAS1-H108A was employed for the synthesis of CLA-rich TAG and 95.21% TAG with 69.19% CLA was obtained under the optimized conditions. The TAG content (95.21%) obtained by immobilized MAS1-H108A is the reported highest value thus far, which was significantly higher than that (9.26%) obtained by Novozym 435 under the same conditions. Although the TAG content comparable to the results obtained in this study could also be obtained by Novozym 435, the used enzyme amount is approximately 5-fold of the immobilized MAS1-H108A. Additionally, the immobilized MAS1-H108A exhibited excellent recyclability during esterification retaining 95.11% of its initial activity after 10 batches. Overall, such immobilized mutant lipase with superior esterification activity and recyclability has the potential to be used in oils and fats industry.
    Matched MeSH terms: Esterification
  3. Physicochemical property enhancement of biodiesel synthesis from hybrid feedstocks of waste cooking vegetable oil and Beauty leaf oil through optimized alkaline-catalysed transesterification
    Milano J, Ong HC, Masjuki HH, Silitonga AS, Kusumo F, Dharma S, et al.
    Waste Manag, 2018 Oct;80:435-449.
    PMID: 30455026 DOI: 10.1016/j.wasman.2018.09.005
    Recycling waste cooking vegetable oils by reclaiming and using these oils as biodiesel feedstocks is one of the promising solutions to address global energy demands. However, producing these biodiesels poses a significant challenge because of their poor physicochemical properties due the high free fatty acid content and impurities present in the feedstock, which will reduce the biodiesel yields. Hence, this study implemented the following strategy in order to address this issue: (1) 70 vol% of waste cooking vegetable oil blended with 30 vol% of Calophyllum inophyllum oil named as WC70CI30 used to alter its properties, (2) a three-stage process (degumming, esterification, and transesterification) was conducted which reduces the free fatty acid content and presence of impurities, and (3) the transesterification process parameters (methanol/oil ratio, reaction temperature, reaction time, and catalyst concentration) were optimized using response surface methodology in order to increase the biodiesel conversion yield. The results show that the WC70CI30 biodiesel has favourable physicochemical properties, good cold flow properties, and high oxidation stability (22.4 h), which fulfil the fuel specifications stated in the ASTM D6751 and EN 14214 standards. It found that the WC70CI30 biodiesel has great potential as a diesel substitute without the need for antioxidants and pour point depressants.
    Matched MeSH terms: Esterification
  4. Anticancer potential of rosmarinic acid and its improved production through biotechnological interventions and functional genomics
    Swamy MK, Sinniah UR, Ghasemzadeh A
    Appl Microbiol Biotechnol, 2018 Sep;102(18):7775-7793.
    PMID: 30022261 DOI: 10.1007/s00253-018-9223-y
    Rosmarinic acid (RA) is a highly valued natural phenolic compound that is very commonly found in plants of the families Lamiaceae and Boraginaceae, including Coleus blumei, Heliotropium foertherianum, Rosmarinus officinalis, Perilla frutescens, and Salvia officinalis. RA is also found in other members of higher plant families and in some fern and horned liverwort species. The biosynthesis of RA is catalyzed by the enzymes phenylalanine ammonia lyase and cytochrome P450-dependent hydroxylase using the amino acids tyrosine and phenylalanine. Chemically, RA can be produced via methods involving the esterification of 3,4-dihydroxyphenyllactic acid and caffeic acid. Some of the derivatives of RA include melitric acid, salvianolic acid, lithospermic acid, and yunnaneic acid. In plants, RA is known to have growth-promoting and defensive roles. Studies have elucidated the varied pharmacological potential of RA and its derived molecules, including anticancer, antiangiogenic, anti-inflammatory, antioxidant, and antimicrobial activities. The demand for RA is therefore, very high in the pharmaceutical industry, but this demand cannot be met by plants alone because RA content in plant organs is very low. Further, many plants that synthesize RA are under threat and near extinction owing to biodiversity loss caused by unscientific harvesting, over-collection, environmental changes, and other inherent features. Moreover, the chemical synthesis of RA is complicated and expensive. Alternative approaches using biotechnological methodologies could overcome these problems. This review provides the state of the art information on the chemistry, sources, and biosynthetic pathways of RA, as well as its anticancer properties against different cancer types. Biotechnological methods are also discussed for producing RA using plant cell, tissue, and organ cultures and hairy-root cultures using flasks and bioreactors. The recent developments and applications of the functional genomics approach and heterologous production of RA in microbes are also highlighted. This chapter will be of benefit to readers aiming to design studies on RA and its applicability as an anticancer agent.
    Matched MeSH terms: Esterification
  5. In situ transesterification of solid coconut waste in a packed bed reactor with CaO/PVA catalyst
    Talha NS, Sulaiman S
    Waste Manag, 2018 Aug;78:929-937.
    PMID: 32559988 DOI: 10.1016/j.wasman.2018.07.015
    In this study, solid coconut waste and CaO/PVA was used as raw material and catalyst respectively to produce biodiesel through in situ transesterification. Both, raw material and catalyst were packed in a packed bed reactor. The reaction was fixed for 3 h and the mixing was kept constant at 350 rpm. The highest biodiesel yield of 95% was obtained at reaction temperature of 61 °C with catalyst loading (CaO/PVA) of 2.29 wt% and methanol to solid ratio of 12:1. CaO-waste derived catalyst has been successfully proven to be utilized as heterogeneous base catalyst for the production of biodiesel from solid coconut waste.
    Matched MeSH terms: Esterification
  6. Insight into the Rhizomucor miehei lipase supported on chitosan-chitin nanowhiskers assisted esterification of eugenol to eugenyl benzoate
    Abd Manan FM, Attan N, Zakaria Z, Mahat NA, Abdul Wahab R
    J Biotechnol, 2018 May 28;280:19-30.
    PMID: 29852195 DOI: 10.1016/j.jbiotec.2018.05.015
    To overcome drawbacks in the conventional chemical route to synthesize eugenyl benzoate, immobilized Rhizomucor miehei lipase (RML) as the biocatalyst was proposed. The RML conjugated to a hybrid support consisting of biopolymers, chitosan (CS) and chitin nanowhiskers (CNWs). 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDAC) was used as the crosslinker to bind the lipase. Immobilization of RML was the highest on crosslinked CS/CNWs which gave a protein loading of ∼8.12 mg/g, corresponding to specific and residual activity of 537 U/g and 137%, respectively. Fourier transform infrared spectroscopy, thermogravimetric analysis-differential thermogravimetry, field emission scanning electron and atomic force microscopy of RML-CS/CNWs revealed that RML was successfully attached to the surface of crosslinked CS/CNWs. Under an optimized condition, the highest yield of eugenyl benzoate (56.3%) was attained after 5 h using 3 mg/mL of RML-CS/CNWs with molar ratio of eugenol: benzoic acid of 3:1, as compared to only 47.3% for the free RML. Analyses of FTIR and NMR on purified eugenyl benzoate affirmed that the ester was successfully produced in the enzymatic esterification. Therefore, the use of the RML-CS/CNWs biocatalysts appears promising to afford good yields of eugenyl benzoate within a relatively shorter reaction time.
    Matched MeSH terms: Esterification
  7. Influence of enzymatic and chemical interesterification on crystallisation properties of refined, bleached and deodourised (RBD) palm oil and RBD palm kernel oil blends
    Norizzah AR, Nur Azimah K, Zaliha O
    Food Res Int, 2018 04;106:982-991.
    PMID: 29580013 DOI: 10.1016/j.foodres.2018.02.001
    Interesterification reaction involves rearrangement of the fatty acid radicals on the glycerol backbone, either randomly (chemical interesterification) or regioselectivity (enzymatic interesterification). Refined, bleached and deodourised palm oil (RBDPO) and palm kernel oil (RBDPKO) were blended in ratios from 25:75 to 75:25 (wt/wt). All blends were subjected to enzymatic (EI) and chemical interesterification (CI) using Lipozyme TL IM (4% w/w) and sodium methoxide (0.2% m/m) as the catalysts, respectively. The effect of EI and CI on the triacylglycerol (TAG) composition, thermal behaviour, polymorphism, crystal morphology and crystallisation kinetics were studied. The aim of this research is to characterise the nature of crystals in food product for certain desired structure. The crystallisation behaviour discussed in this study involves microstructure (PLM), polymorphism (XRD), thermal properties and crystallisation kinetics by DSC. The alteration in TAG composition was greater after CI as compared to EI with the reduction of LaLaLa (from 11.00% to 5.15%) and POO (from 14.28% to 4.87%). The DSC complete melting and crystallisation temperature of blend with 75% PO increased after CI, from 39.58 °C to 41.67 °C and from -30.84 °C to -28.33 °C, respectively. EI contributed to finer crystals than CI. However, the β' and β polymorph mixture and crystallisation kinetics (n = 2) of PO-PKO blends did not change after CI and EI. The knowledge on controlling crystallisation of RBDPO and RBDPKO blends is vital for proper processing condition like margarine production.
    Matched MeSH terms: Esterification
  8. Fulltext Kinetics and Optimization of Lipophilic Kojic Acid Derivative Synthesis in Polar Aprotic Solvent Using Lipozyme RMIM and Its Rheological Study
    Ishak N, Lajis AFB, Mohamad R, Ariff AB, Mohamed MS, Halim M, et al.
    Molecules, 2018 Feb 24;23(2).
    PMID: 29495254 DOI: 10.3390/molecules23020501
    The synthesis of kojic acid derivative (KAD) from kojic and palmitic acid (C16:0) in the presence of immobilized lipase from Rhizomucor miehei (commercially known as Lipozyme RMIM), was studied using a shake flask system. Kojic acid is a polyfunctional heterocycles that acts as a source of nucleophile in this reaction allowing the formation of a lipophilic KAD. In this study, the source of biocatalyst, Lipozyme RMIM, was derived from the lipase of Rhizomucor miehei immobilized on weak anion exchange macro-porous Duolite ES 562 by the adsorption technique. The effects of solvents, enzyme loading, reaction temperature, and substrate molar ratio on the reaction rate were investigated. In one-factor-at-a-time (OFAT) experiments, a high reaction rate (30.6 × 10-3 M·min-1) of KAD synthesis was recorded using acetone, enzyme loading of 1.25% (w/v), reaction time of 12 h, temperature of 50 °C and substrate molar ratio of 5:1. Thereafter, a yield of KAD synthesis was optimized via the response surface methodology (RSM) whereby the optimized molar ratio (fatty acid: kojic acid), enzyme loading, reaction temperature and reaction time were 6.74, 1.97% (w/v), 45.9 °C, and 20 h respectively, giving a high yield of KAD (64.47%). This condition was reevaluated in a 0.5 L stirred tank reactor (STR) where the agitation effects of two impellers; Rushton turbine (RT) and pitch-blade turbine (PBT), were investigated. In the STR, a very high yield of KAD synthesis (84.12%) was achieved using RT at 250 rpm, which was higher than the shake flask, thus indicating better mixing quality in STR. In a rheological study, a pseudoplastic behavior of KAD mixture was proposed for potential application in lotion formulation.
    Matched MeSH terms: Esterification
  9. Rhizomucor miehei lipase immobilized on reinforced chitosan-chitin nanowhiskers support for synthesis of eugenyl benzoate
    Abdul Manan FM, Attan N, Widodo N, Aboul-Enein HY, Wahab RA
    Prep Biochem Biotechnol, 2018 Jan 02;48(1):92-102.
    PMID: 29194017 DOI: 10.1080/10826068.2017.1405021
    An alternative environmentally benign support was prepared from chitosan-chitin nanowhiskers (CS/CNWs) for covalent immobilization of Rhizomucor miehei lipase (RML) to increase the operational stability and recyclability of RML in synthesizing eugenyl benzoate. The CS/CNWs support and RML-CS/CNWs were characterized using X-ray diffraction, fluorescent microscopy, and Fourier transform infrared spectroscopy. Efficiency of the RML-CS/CNWs was compared to the free RML to synthesize eugenyl benzoate for parameters: reaction temperature, stirring rate, reusability, and thermal stability. Under optimal experimental conditions (50°C, 250 rpm, catalyst loading 3 mg/mL), a twofold increase in yield of eugenyl benzoate was observed for RML-CS/CNWs as compared to free RML, with the former achieving maximum yield of the ester at 62.1% after 5 hr. Results demonstrated that the strategy adopted to prepare RML-CS/CNWs was useful, producing an improved and prospectively greener biocatalyst that supported a sustainable process to prepare eugenyl benzoate. Moreover, RML-CS/CNWs are biodegradable and perform esterification reactions under ambient conditions as compared to the less eco-friendly conventional acid catalyst. This research provides a facile and promising approach for improving activity of RML in which the resultant RML-CS/CNWs demonstrated good operational stability for up to eight successive esterification cycles to synthesize eugenyl benzoate.
    Matched MeSH terms: Esterification
  10. Enzymatic esterification of eugenol and benzoic acid by a novel chitosan-chitin nanowhiskers supported Rhizomucor miehei lipase: Process optimization and kinetic assessments
    Manan FMA, Attan N, Zakaria Z, Keyon ASA, Wahab RA
    Enzyme Microb Technol, 2018 Jan;108:42-52.
    PMID: 29108626 DOI: 10.1016/j.enzmictec.2017.09.004
    A biotechnological route via enzymatic esterification was proposed as an alternative way to synthesize the problematic anti-oxidant eugenyl benzoate. The new method overcomes the well-known drawbacks of the chemical route in favor of a more sustainable reaction process. The present work reports a Box-Behnken design (BBD) optimization process to synthesize eugenyl benzoate by esterification of eugenol and benzoic acid catalyzed by the chitosan-chitin nanowhiskers supported Rhizomucor miehei lipase (RML-CS/CNWs). Effects of four reaction parameters: reaction time, temperature, substrate molar ratio of eugenol: benzoic acid and enzyme loading were assessed. Under optimum conditions, a maximum conversion yield as high as 66% at 50°C in 5h using 3mg/mL of RML-CS/CNWs, and a substrate molar ratio (eugenol: benzoic acid) of 3:1. Kinetic assessments revealed the RML-CS/CNWs catalyzed the reaction via a ping-pong bi-bi mechanism with eugenol inhibition, characterized by a Vmax of 3.83mMmin-1. The Michaelis-Menten constants for benzoic acid (Km,A) and eugenol (Km,B) were 34.04 and 138.28mM, respectively. The inhibition constant for eugenol (Ki,B) was 438.6mM while the turnover number (kcat) for the RML-CS/CNWs-catalyzed esterification reaction was 40.39min-1. RML-CS/CNWs were reusable up to 8 esterification cycles and showed higher thermal stability than free RML.
    Matched MeSH terms: Esterification
  11. Optimization and kinetic study of ultrasonic assisted esterification process from rubber seed oil
    Trinh H, Yusup S, Uemura Y
    Bioresour Technol, 2018 Jan;247:51-57.
    PMID: 28946094 DOI: 10.1016/j.biortech.2017.09.075
    Recently, rubber seed oil (RSO) has been considered as a promising potential oil source for biodiesel production. However, RSO is a non-edible feedstock with a significant high free fatty acid (FFA) content which has an adverse impact on the process of biodiesel production. In this study, ultrasonic-assisted esterification process was conducted as a pre-treatment step to reduce the high FFA content of RSO from 40.14% to 0.75%. Response surface methodology (RSM) using central composite design (CCD) was applied to the design of experiments (DOE) and the optimization of esterification process. The result showed that methanol to oil molar ratio was the most influential factor for FFA reduction whereas the effect of amount of catalyst and the reaction were both insignificant. The kinetic study revealed that the activation energy and the frequency factor of the process are 52.577kJ/mol and 3.53×108min-1, respectively.
    Matched MeSH terms: Esterification
  12. Production of biodiesel from palm fatty acid distillate by microwave-assisted sulfonated glucose acid catalyst
    Nur Nazlina Saimon, Heng Khuan Eu, Anwar Johari, Norzita Ngadi, Mazura Jusoh, Zaki Yamani Zakaria
    Sains Malaysiana, 2018;47:109-115.
    Biodiesel, one of the renewable energy sources has gained attention for decades as the alternative fuel due to its remarkable properties. However, there are several drawbacks from the industrial production of biodiesel such as the spike in the production cost, environmental issues related to the usage of homogeneous catalyst and profitability in long term. One of the solutions to eliminate the problem is by utilizing low cost starting material such as palm fatty acid distillate (PFAD). PFAD is a byproduct from the refining of crude palm oil and abundantly available. Esterification of PFAD to biodiesel will be much easier with the presence of heterogeneous acid catalyst. Most of acid catalyst preparation involves series of heating process using conventional method. In this study, microwave was utilized in catalyst preparation, significantly reducing the reaction time from conventional heating method. The catalyst produced was characterized using X-Ray Diffraction (XRD), Brunauer Emmet and Teller (BET), Scanning Electron Microscopy (SEM), Temperature-Programmed Desorption - Ammonia (TPD-NH3) and Fourier Transform Infrared (FTIR) while percentage yield and conversion of the PFAD were analysed by gas chromatography - flame ionization detector (GC-FID) and acid-base titration, respectively. It has been demonstrated that the percentage yield of biodiesel from the PFAD by employing sulfonated glucose acid catalyst (SGAC) reached 98.23% under the following conditions: molar ratio of methanol to PFAD of 10:1, catalyst loading of 2.5% and reaction temperature of 70oC. The microwave-assisted SGAC showed its potential to replace the SGAC produced via conventional heating method.
    Matched MeSH terms: Esterification
  13. Esterification of levulinic acid to levulinate esters in the presence of sulfated silica catalyst
    Nur Aainaa Syahirah Ramli, Nur Irsalina Hisham, Nor Aishah Saidina Amin
    Sains Malaysiana, 2018;47:1131-1138.
    Levulinic acid (LA) is one of biomass derived building block chemicals with various applications. Catalytic esterification
    of LA with alkyl alcohol produces levulinate ester which can be applied as fragrance, flavouring agents, as well as fuel
    additives. In this study, a series of sulfated silica (SiO2
    ) catalyst was prepared by modification of SiO2
    with sulfuric acid
    (H2
    SO4
    ) at different concentrations; 0.5 M to 5 M H2
    SO4
    . The catalysts were characterized, and tested for esterification
    of LA with ethanol to ethyl levulinate (EL). The effect of various reaction parameters including reaction time, catalyst
    loading and molar ratio of LA to ethanol on esterification of LA to EL were inspected. The catalyst with high concentration
    of acid sites seemed suitable for LA esterification to EL. Among the sulfated SiO2
    catalysts tested (0.5 M-SiO2
    , 1 M-SiO2
    ,
    3 M-SiO2
    and 5 M-SiO2
    ), 3 M-SiO2
    exhibited the highest performance with the optimum EL yield of 54% for reaction
    conducted at reflux temperature for 4 h, 30% 3 M-SiO2
    loading and LA to ethanol molar ratio of 1:20. Besides, the
    reusability of 3 M-SiO2
    catalyst for LA esterification with ethanol was examined for five cycles. Esterification of LA with
    methanol and 1-butanol were also carried out for methyl levulinate (ML) and butyl levulinate (BL) productions with 69%
    and 40% of ML and BL yields, respectively. This study demonstrates the potential of sulfated SiO2
    catalyst for levulinate
    ester production from LA at mild process condition.
    Matched MeSH terms: Esterification
  14. Evaluating the Potential of Oleaginous Yeasts as Feedstock for Biodiesel Production
    Mukhtar H, Suliman SM, Shabbir A, Mumtaz MW, Rashid U, Rahimuddin SA
    Protein Pept Lett, 2018;25(2):195-201.
    PMID: 29359654 DOI: 10.2174/0929866525666180122112805
    BACKGROUND: Lipid-producing microorganisms, said to be oleaginous have been recognized since several years. We had investigated the effects of medium components and culturing situations on cell growth and lipid accumulation of oleaginous yeasts which were analytically examined so as to enhance lipid yield for biodiesel production.

    OBJECTIVE: The main objective of this study was to explore oleaginous yeast, Yarrowia lipolytica isolated from soil and optimization of culture conditions and medium components to obtained better quality microbial oil for biodiesel production.

    METHODS: Fifty yeast strains were isolated from soil from different regions of Lahore and eleven of them were selected for oil production. The isolated yeast colonies were screened to further check their lipid producing capabilities by the qualitative analysis. Five yeast strains were designated as oleaginous because they produced more than 16% of oil based on their biomass. To estimate the total lipid content of yeast cells, the extraction of lipids was done by performing the procedure proposed by Bligh and Dyer. The transesterification of yeast oils was performed by using different methods. There were three different strategies customized to transesterifying microbial oil using base catalyzed transesterification, acid catalyzed transesterification and enzyme-based transesterification. After completion of transesterification, sample was used for fatty acid methyl esters (FAMEs) were analyzed by gas-chromatograph with ionization detector type MS.

    RESULTS: The isolate IIB-10 identified as Yarrowia lipolytica produced maximum amount of lipids i.e. 22.8%. More amount of biomass was obtained when cane molasses was utilized as carbon source where it produced 29.4 g/L of biomass while sucrose and lactose were not utilized by IIB-10 and no biomass was obtained. Similarly, meat extracts showed best results when it was used as nitrogen source because it resulted in 35.8 g/L biomass of Yarrowia lipolytica IIB-10. The culturing conditions like size of inoculum, effect of pH and time of incubation were also studied. The 10% of inoculum size produced 25.4 g/L biomass at 120 h incubation time, while the pH 7 was the optimum pH at which 24.8 g/L biomass was produced by Yarrowia lipolytica IIB-10. GC-MS analysis showed that biodiesel produced by transesterification contained similar fatty acids as found in vegetable oil for this reason it is widely accepted feedstock for biodiesel production.

    CONCLUSION: The analysis of fatty acids methyl esters showed the similar composition of microbial oil as in vegetable oils and high amount of methyl esters were obtained after transesterification. Therefore, potentially oleaginous yeast could be used to generate a large amount of lipids for biodiesel production that will be the better substitute of petroleum-based diesel and will also control the environmental pollution.

    Matched MeSH terms: Esterification
  15. Palm-Based Neopentyl Glycol Diester: A Potential Green Insulating Oil
    Raof NA, Yunus R, Rashid U, Azis N, Yaakub Z
    Protein Pept Lett, 2018;25(2):171-179.
    PMID: 29359647 DOI: 10.2174/0929866525666180122095056
    BACKGROUND: The transesterification of high oleic palm oil methyl ester (HOPME) with neopentyl glycol (NPG) has been investigated. The present study revealed the application of low-pressure technology as a new synthesis method to produce NPG diesters. Single variable optimization and response surface methodology (RSM) were implemented to optimize the experimental conditions to achieve the maximum composition (wt%) of NPG diesters.

    OBJECTIVE: The main objective of this study was to optimize the production of NPG diesters and to characterize the optimized esters with typical chemical, physical and electrical properties to study its potential as insulating oil.

    METHODS: The transesterification reaction between HOPME and NPG was conducted in a 1L three-neck flask reactor at specified temperature, pressure, molar ratio and catalyst concentration. For the optimization, four factors have been studied and the diester product was characterized by using gas chromatography (GC) analysis. The synthesized esters were then characterized with typical properties of transformer oil such as flash point, pour point, viscosity and breakdown voltage and were compared with mineral insulating oil and commercial NPG dioleate. For formulation, different samples of NPG diesters with different concentration of pour point depressant were prepared and each sample was tested for its pour point measurement.

    RESULTS: The optimum conditions inferred from the analyses were: molar ratio of HOPME to NPG of 2:1.3, temperature = 182°C, pressure = 0.6 mbar and catalyst concentration of 1.2%. The synthesized NPG diesters showed very important improvement in fire safety compared to mineral oil with flash point of 300°C and 155°C, respectively. NPG diesters also exhibit a relatively good viscosity of 21 cSt. The most striking observation to emerge from the data comparison with NPG diester was the breakdown voltage, which was higher than mineral oil and definitely in conformance to the IEC 61099 limit at 67.5 kV. The formulation of synthesized NPD diesters with VISCOPLEX® pour point depressant has successfully increased the pour point of NPG diester from -14°C to -48°C.

    CONCLUSION: The reaction time for the transesterification of HOPME with NPG to produce NPG diester was successfully reduced to 1 hour from the 14 hours required in the earlier synthesis method. The main highlight of this study was the excess reactant which is no longer methyl ester but the alcohol (NPG). The optimum reaction conditions for the synthesis were molar ratio of 2:1.13 for NPG:HOPME, 182°C, 0.6 mbar and catalyst concentration of 1.2 wt%. The maximum NPG diester yield of 87 wt% was consistent with the predicted yield of 87.7 wt% obtained from RSM. The synthesized diester exhibited better insulating properties than the commercial products especially with regards to the breakdown voltage, flash point and moisture content.

    Matched MeSH terms: Esterification
  16. Fulltext One-Step Partially Purified Lipases (ScLipA and ScLipB) from Schizophyllum commune UTARA1 Obtained via Solid State Fermentation and Their Applications
    Kam YC, Woo KK, Ong LGA
    Molecules, 2017 Dec 08;22(12).
    PMID: 29292721 DOI: 10.3390/molecules22122106
    Lipases with unique characteristics are of value in industrial applications, especially those targeting cost-effectiveness and less downstream processes. The aims of this research were to: (i) optimize the fermentation parameters via solid state fermentation (SSF); and (ii) study the performance in hydrolysis and esterification processes of the one-step partially purified Schizophyllum commune UTARA1 lipases. Lipase was produced by cultivating S. commune UTARA1 on sugarcane bagasse (SB) with used cooking oil (UCO) via SSF and its production was optimized using Design-Expert® 7.0.0. Fractions 30% (ScLipA) and 70% (ScLipB) which contained high lipase activity were obtained by stepwise (NH₄)₂SO₄ precipitation. Crude fish oil, coconut oil and butter were used to investigate the lipase hydrolysis capabilities by a free glycerol assay. Results showed that ScLipA has affinities for long, medium and short chain triglycerides, as all the oils investigated were degraded, whereas ScLipB has affinities for long chain triglycerides as it only degrades crude fish oil. During esterification, ScLipA was able to synthesize trilaurin and triacetin. Conversely, ScLipB was specific towards the formation of 2-mono-olein and triacetin. From the results obtained, it was determined that ScLipA and ScLipB are sn-2 regioselective lipases. Hence, the one-step partial purification strategy proved to be feasible for partial purification of S. commune UTARA1 lipases that has potential use in industrial applications.
    Matched MeSH terms: Esterification
  17. Fulltext The Role of Solvent-Accessible Leu-208 of Cold-Active Pseudomonas fluorescens Strain AMS8 Lipase in Interfacial Activation, Substrate Accessibility and Low-Molecular Weight Esterification in the Presence of Toluene
    Yaacob N, Ahmad Kamarudin NH, Leow ATC, Salleh AB, Raja Abd Rahman RNZ, Mohamad Ali MS
    Molecules, 2017 Aug 12;22(8).
    PMID: 28805665 DOI: 10.3390/molecules22081312
    The alkaline cold-active lipase from Pseudomonas fluorescens AMS8 undergoes major structural changes when reacted with hydrophobic organic solvents. In toluene, the AMS8 lipase catalytic region is exposed by the moving hydrophobic lid 2 (Glu-148 to Gly-167). Solvent-accessible surface area analysis revealed that Leu-208, which is located next to the nucleophilic Ser-207 has a focal function in influencing substrate accessibility and flexibility of the catalytic pocket. Based on molecular dynamic simulations, it was found that Leu-208 strongly facilitates the lid 2 opening via its side-chain. The KM and Kcat/KM of L208A mutant were substrate dependent as it preferred a smaller-chain ester (pNP-caprylate) as compared to medium (pNP-laurate) or long-chain (pNP-palmitate) esters. In esterification of ethyl hexanoate, L208A promotes a higher ester conversion rate at 20 °C but not at 30 °C, as a 27% decline was observed. Interestingly, the wild-type (WT) lipase's conversion rate was found to increase with a higher temperature. WT lipase AMS8 esterification was higher in toluene as compared to L208A. Hence, the results showed that Leu-208 of AMS8 lipase plays an important role in steering a broad range of substrates into its active site region by regulating the flexibility of this region. Leu-208 is therefore predicted to be crucial for its role in interfacial activation and catalysis in toluene.
    Matched MeSH terms: Esterification
  18. Factors screening to statistical experimental design of racemic atenolol kinetic resolution via transesterification reaction in organic solvent using free Pseudomonas fluorescens lipase
    Agustian J, Kamaruddin AH, Aboul-Enein HY
    Chirality, 2017 Jul;29(7):376-385.
    PMID: 28439969 DOI: 10.1002/chir.22702
    As the (R)-enantiomer of racemic atenolol has no β-blocking activity and no lack of side effects, switching from the racemate to the (S)-atenolol is more favorable. Transesterification of racemic atenolol using free enzymes investigated as a resource to resolve the racemate via this method is limited. Screenings of enzyme, medium, and acetyl donor were conducted first to give Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate. A statistical design of the experiment was then developed using Central Composite Design on some operational factors, which resulted in the conversions of 11.70-61.91% and substrate enantiomeric excess (ee) of 7.31-100%. The quadratic models are acceptable with R2 of 95.13% (conversion) and 89.63% (ee). The predicted values match the observed values reasonably well. Temperature, agitation speed, and substrate molar ratio factor have low effects on conversion and ee, but enzyme loading affects the responses highly. The interaction of temperature-agitation speed and temperature-substrate molar ratio show significant effects on conversion, while temperature-agitation speed, temperature-substrate molar ratio, and agitation speed-substrate molar ratio affect ee highly. Optimum conditions for the use of Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate were found at 45°C, 175 rpm, 2000 U, and 1:3.6 substrate molar ratio.
    Matched MeSH terms: Esterification
  19. Comparative study of the antioxidant activities of some lipase-catalyzed alkyl dihydrocaffeates synthesized in ionic liquid
    Gholivand S, Lasekan O, Tan CP, Abas F, Wei LS
    Food Chem, 2017 Jun 01;224:365-371.
    PMID: 28159281 DOI: 10.1016/j.foodchem.2016.12.075
    The solubility limitations of phenolic acids in many lipidic environments are now greatly improved by their enzymatic esterification in ionic liquids (ILs). Herein, four different ILs were tested for the esterification of dihydrocaffeic acid with hexanol and the best IL was selected for the synthesis of four other n-alkyl esters with different chain-lengths. The effect of alkyl chain length on the anti-oxidative properties of the resulted purified esters was investigated using β-carotene bleaching (BCB) and free radical scavenging method DPPH and compared with butylated hydroxytoluene (BHT) as reference compound. All four esters (methyl, hexyl, dodecyl and octadecyl dihydrocaffeates) exhibited relatively strong radical scavenging abilities. The scavenging activity of the test compounds was in the following order: methyl ester>hexyl ester⩾dodecyl ester>octadecyl ester>BHT while the order for the BCB anti-oxidative activity was; BHT>octadecyl ester>dodecyl ester>hexyl ester>methyl ester.
    Matched MeSH terms: Esterification
  20. Microalgae biorefinery: High value products perspectives
    Chew KW, Yap JY, Show PL, Suan NH, Juan JC, Ling TC, et al.
    Bioresour Technol, 2017 Apr;229:53-62.
    PMID: 28107722 DOI: 10.1016/j.biortech.2017.01.006
    Microalgae have received much interest as a biofuel feedstock in response to the uprising energy crisis, climate change and depletion of natural sources. Development of microalgal biofuels from microalgae does not satisfy the economic feasibility of overwhelming capital investments and operations. Hence, high-value co-products have been produced through the extraction of a fraction of algae to improve the economics of a microalgae biorefinery. Examples of these high-value products are pigments, proteins, lipids, carbohydrates, vitamins and anti-oxidants, with applications in cosmetics, nutritional and pharmaceuticals industries. To promote the sustainability of this process, an innovative microalgae biorefinery structure is implemented through the production of multiple products in the form of high value products and biofuel. This review presents the current challenges in the extraction of high value products from microalgae and its integration in the biorefinery. The economic potential assessment of microalgae biorefinery was evaluated to highlight the feasibility of the process.
    Matched MeSH terms: Esterification
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