scholarly journals Preparation of Immobilized Lipase Based on Hollow Mesoporous Silica Spheres and Its Application in Ester Synthesis

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 395 ◽  
Author(s):  
Zhe Dong ◽  
Meng-Ying Jiang ◽  
Jie Shi ◽  
Ming-Ming Zheng ◽  
Feng-Hong Huang
Keyword(s):  
Reaction Time ◽  
Mesoporous Silica ◽  
Immobilized Lipase ◽  
Lipid Production ◽  
Candida Rugosa ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
Free System ◽  
Hollow Mesoporous Silica

In this study, Candida rugosa lipase (CRL) was immobilized into modified hollow mesoporous silica (HMSS) materials with different hydrophobicity. Among propyl-(C3), phenyl-(C6), octyl-(C8), and octadecyl-(C18) modified HMSS as well as native HMSS, taking advantage of more hydrophobic microenvironment, the HMSS-C18-CRL showed exceptional performance in enzymatic esterification reaction. Using the novel HMSS-C18 with immobilized CRL (HMSS-C18-CRL), we investigated the esterification of phytosterols with polyunsaturated fat acid (PUFA) in a solvent-free system for the production of phytosterols esters. Response surface methodology (RSM) was applied to model and optimize the reaction conditions, namely, the enzyme load (5–25%), reaction time (10–110 min), molar ratio of α-linolenic acid (ALA)/phytosterols (1:1–7:1) and represented by the letters E, T, and M respectively. Best-fitting models were successfully established by multiple regressions with backward elimination. The optimum production was achieved at 70 min for reaction time, 20% based on the weight of substrate for enzyme loading, and 5.6:1 for ALA/phytosterols molar ratio. Under optimized conditions, a conversion of about 90 ± 2% was achieved. These results indicated that HMSS-C18-CRL demonstrates to be a promising catalyst and can be potentially applied in the functional lipid production.

scholarly journals OPTIMASI PROSES PEMBUATAN BIODIESEL DARI ASAM LEMAK SAWIT DISTILAT (ALSD) DAN DIMETHYL CARBONATE (DMC) MENGGUNAKAN KATALIS NOVOZYM®435

2016 ◽  
Vol 5 (1) ◽  
pp. 13-19
Author(s):  
William ◽  
Johan Senjaya ◽  
Taslim ◽  
Tjahjono Herawan ◽  
Meta Rivani
Keyword(s):  
Fatty Acid ◽  
Reaction Time ◽  
Energy Content ◽  
Immobilized Lipase ◽  
Chemical Properties ◽  
Intermediate Compound ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
Enzymatic Esterification ◽  
Dialkyl Carbonate

Biodiesel production has rapidly grown over the last decades, and it has attracted much attention in the market as fuel that promising substitute for petroleum diesel, because its physical and chemical properties and energy content are similar to those of petroleum diesel. The main problem in producing biodiesel is its high cost which could be reduced by use of less expensive feedstock. Therefore, in this work biodiesel is synthesized by enzymatic esterification from low quality feedstock which is unrefined and much cheaper than the refined oil, such as palm fatty acid distillate (PFAD) with dialkyl carbonate using immobilized lipase (Novozym®435). Enzymatic process has certain advantages over the chemical process, as it is less energy intensive, allowing the esterification of glycerides with high free fatty acid contents (PFAD, 85-95% FFA) and no enzymatic activity loss. Methanol replaced by dialkyl carbonate, especially DMC due to esterification (methanolysis) is close to equilibrium reaction whereas using DMC the intermediate compound immediately decomposes to carbon dioxide and an alcohol, which have been investigated. Moreover, DMC are cheap, eco-friendly chemical, non-toxic properties and widely available. Factors affecting the reaction such as DMC to PFAD molar ratio, reaction temperature, reaction time and catalyst concentration were systematically analyzed by response surface methodology (RSM) with central composite design (CCD). The optimal condition is using 6:1 molar ratio of DMC to PFAD at 60 oC, for a reaction time 3h in the presence 10wt% of catalyst (based on oil weight). The results showed that synthesis of biodiesel through enzymatic esterification using PFAD suitable for biodiesel production.

scholarly journals Enzymatic Esterification as Potential Strategy to Enhance the Sorbic Acid Behavior as Food and Beverage Preservative

Fermentation ◽  
2020 ◽  
Vol 6 (4) ◽  
pp. 96
Author(s):  
Federico Zappaterra ◽  
Daniela Summa ◽  
Bruno Semeraro ◽  
Raissa Buzzi ◽  
Claudio Trapella ◽  
...  
Keyword(s):  
Sorbic Acid ◽  
Immobilized Lipase ◽  
Antimicrobial Properties ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
Free System ◽  
Food And Beverage ◽  
Solvent Free System ◽  
Potential Strategy ◽  
Acid Derivate

Sorbic acid is the most commonly used preservative in the food industry. The antimicrobial inhibition of sorbic acid could be influenced by its lipophilic nature, which reduces its use in hydrophilic food formulations. Reactions between sorbic acid and glycerol catalyzed by lipases were studied in order to develop a novel sorbic acid derivate with a promising hydrophilic profile. The esterification reaction between sorbic acid and glycerol in a solvent-free system were performed with an immobilized lipase B from Candida antarctica (CALB). The glycerol sorbate product has been tested against S. griseus bacterium and Saccharomyces cerevisiae yeast. Results indicate that the esterification of sorbic acid with glycerol does improve its antimicrobial properties against Saccharomyces cerevisie. The reported results demonstrate that esterification can be used as a strategy to improve the antimicrobial activity of sorbic acid.

scholarly journals Optimization of lipase-catalyzed synthesis of flavour esters in solvent free system

2014 ◽  
Vol 6 (1) ◽  
Author(s):  
Syamsul Kamar Muhamad ◽  
Salina Mat Radzi ◽  
Siti Salhah Othman ◽  
Mohd Basyaruddin Abdul Rahman ◽  
Hanina Mohd Noor
Keyword(s):  
Reaction Time ◽  
Chain Length ◽  
Reaction Temperature ◽  
Immobilized Lipase ◽  
Solvent Free ◽  
Esterification Reaction ◽  
Reaction Parameters ◽  
Free System ◽  
Solvent Free System ◽  
Flavour Esters

The effects of important reaction parameters for enhancing flavour esters formation through lipase-catalyzed reaction were investigated in this study.Various commercial immobilized lipases were used to catalyze the esterification reaction between short-chain fatty acids and alcohols to produce flavour esters which are nonyl caprylate and ethyl valerate which differ in chain length of esters. These synthetic flavour esters with fruity notes are widely used in food, cosmetic and pharmaceutical industries. The effect of various reaction parameters was optimized to obtain a high yield of flavour esters. A maximum percentage for nonyl caprylate with conversion of flavour esters more than 90 % in a solvent-free system was successfully obtained under the following conditions: reaction time (RT), 5 hours; reaction temperature, 40 °C; amount of immobilized lipase, 25 % w/w of total substrate and shaking speed 200 rpm. Compared to ethyl valerate, a maximum percentage conversion of flavour ester more than 80 % in solvent free system was successfully obtained under following conditions: reaction time (RT), 45 minutes; reaction temperature, 40 °C; amount of immobilized lipase, 15 % w/w of total substrate and shaking speed 200 rpm. Comparison between these two ester showed that the chain length give an effect to optimize the reaction condition in esterification reaction.

Free Candida Rugosa Lipase–Catalyzed Synthesis Of Citronellyl Butyrate In n–Hexane By Direct Esterification: Effect Of Reaction Parameters

2012 ◽  
Author(s):  
Irvan Dahlan ◽  
Azlina Harun @ Kamaruddin ◽  
Ghasem D. Najafpour
Keyword(s):  
Butyric Acid ◽  
Active Sites ◽  
Immobilized Lipase ◽  
Candida Rugosa ◽  
Candida Rugosa Lipase ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Reaction Parameters ◽  
Direct Esterification ◽  
Competitive Nature

Sintesis sitronelil butirat melalui pengesteran langsung telah dikaji di dalam n–hexane sebagai pelarut organik yang dimangkinkan oleh lipase bebas dan lipase tersekatgerak daripada Candida rugosa. Kajian telah dijalankan untuk mengesahkan pengaruh pelbagai parameter pada pembentukan sitronelil butirat oleh lipase bebas daripada Candida rugosa, iaitu kesan kepekatan lipase, nisbah molar substrat, suhu, tiga jenis bahan sokongan untuk lipase tersekatgerak dan nisbah sekatgerak. Peningkatan kepekatan lipase bebas menyebabkan peningkatan kepada penukaran asid. Sifat peningkatan tidak berubah dari tindak balas pengesteran dapat diperhatikan pada kepekatan lipase tinggi yang memberikan kepekatan optimum lipase pada 3.33 g/l dengan penukaran asid sebanyak 92%. Kemungkinan ini disebabkan oleh tapak aktif lipase yang berlebihan yang berada di dalam zarah lipase pukal, yang tidak memberi sumbangan bererti kepada tindak balas. Aktiviti lipase didapati terencat dengan bertambahnya kepekatan asid butirik (pada kepekatan sitronelol tetap) dan sitronelol (pada kepekatan asid butirik tetap). Ini disebabkan adanya persaingan semulajadi pengikatan alkohol dan asid. Penukaran asid optimum diperolehi pada suhu 40°C selepas 24 jam pengeraman. Bagaimanapun, atas dari suhu ini, aktiviti pengesteran yang dimangkinkan oleh lipase mula menurun kerana penyahaslian protein. Daripada tiga jenis sokongan yang digunakan untuk lipase tersekatgerak, Amberlite MB–1 menunjukkan penukaran asid tertinggi berbanding dengan Amberlite XAD–1180 dan Celite 545. Penukaran asid optimum diperolehi pada nisbah sekatgerak 10 mg lipase/g penyokong. Pada nisbah sekatgerak ini, lipase mengoptimumkan sentuhan dengan permukaan penyokong dengan mengekalkan konformasi yang aktif pada tahap optimum. Kata kunci: Sitronelil butirat; lipase Candida rugosa; pengesteran langsung; lipase tersekatgerak; pelarut organik Free and immobilized Candida rugosa lipases were investigated for the synthesis of citronellyl butyrate by direct esterification reaction in n–hexane as organic solvent. A set of experiments was carried out to verify the influence of various parameters on the formation of citronellyl butyrate by free Candida rugosa lipase, such as lipase loading, substrate molar ratio, temperature, three kinds of support for immobilization, and ratio of immobilization. The conversion was increased with increasing lipase loading. The behavior of leveling–off in esterification was observed at higher lipase loading which gave the optimal amount of lipase loading at 3.33 g/l with 92% conversion. This might be due to the excess of lipase active sites, which remained inside the bulk of lipase particles, was not contributing significantly to the reaction. Increasing butyric acid and citronellol concentrations (at fixed citronellol and butyric acid concentrations, respectively) inhibited the lipase activity due to competitive nature of alcohol and acid binding. Optimal acid conversion was obtained at 40°C after 24–h incubation time. Above this temperature, however, the activity of lipase–catalyzed esterification begins to decrease due to denaturation of protein. From the three kinds of supports for immobilized lipase, Amberlite MB–1 showed the highest conversion compared to Amberlite XAD–1180 and Celite 545. The optimal acid conversion was obtained at lipase loading of 10 mg lipase/g support. At this loading, lipase attempts to optimize its contact with the surface of the support whereby optimum active conformation was retained. Key words: Citronellyl butyrate; Candida rugosa lipase; direct esterification; immobilized lipase; organic media

scholarly journals Optimization of enzymatic synthesis of ethyl hexanoate in a solvent free system using response surface methodology (RSM)

Biocatalysis ◽  
2018 ◽  
Vol 4 (1) ◽  
pp. 14-26 ◽  
Author(s):  
Sarita D. Gawas ◽  
Nidya Lokanath ◽  
Virendra K. Rathod
Keyword(s):  
Response Surface Methodology ◽  
Response Surface ◽  
Solvent Free ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
Ethyl Hexanoate ◽  
Free System ◽  
Acid Ratio ◽  
Solvent Free System

Abstract The present paper demonstrates application of biocatalysis to the synthesis of ethyl hexanoate, i.e. pineapple flavour ester, in a solvent free system. In order to evaluate the effect of various process parameters on reaction conversion, response surface methodology (RSM) complemented by central composite design (CCD) was employed. A maximum conversion of 88.57% was obtained while changing one factor at a time, at optimum conditions of temperature (50 °C), enzyme dose (2%), molar ratio acid to alcohol (1:3), speed of agitation 250 rpm and reaction time of 120 min. Based on this RSM study, the optimum predicted conditions were: 1:3.39 alcohol to acid ratio, 2.35% enzyme loading and 48.83 oC, for a predicted conversion of 90.99%. The activation energy for the enzymatic esterification was determined and calculated to be 25.76 kJ/mol. The positive values of Gibbs-free energy (ΔG), enthalpy (ΔH) and negative value of entropy (ΔS) revealed that the esterification reaction was non-spontaneous and an endothermic reaction. The reaction seems to follow bi-substrate Ping Pong Bi Bi mechanism with inhibition by both substrates.

Optimization of Eugenol Ester Using Statistical Approach of Response Surface Methodology

2016 ◽  
Vol 857 ◽  
pp. 469-474 ◽  
Author(s):  
Salina Mat Radzi ◽  
M.Z.R. Hanif ◽  
K.M.W. Syamsul
Keyword(s):  
Response Surface Methodology ◽  
Reaction Time ◽  
Response Surface ◽  
Statistical Approach ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
Lipozyme Tl Im ◽  
Green Route ◽  
Molar Ratio Substrate

In this study, optimization of eugenol caprylate, a type of ester was successfully carried out using statistical approach of Response surface methodology (RSM). The eugenol ester was synthesized via green route of an enzymatic esterification reaction between eugenol and caprylic acid. Four important enzymology parameters were investigated such as reaction time, temperature, molar ratio of substrate and amount of enzyme. High percentage conversion of ester >80 % was achieved at reaction time of 240.40 minute, 25.52 mg of enzyme’s amount, 1.13 molar ratio substrate and temperature of 56.57 °C based on the optimum conditions. The efficiency of a new dual enzymes system consisting of Novozym 435 and Lipozyme TL IM was also evaluated based on the effect of heat and its reusability on the esterification reaction.

Study on the Synthesis of Isoamyl Acetate Catalyzed by Strong Acidic Cation Exchange Resin

2011 ◽  
Vol 396-398 ◽  
pp. 2411-2415 ◽  
Author(s):  
Ping Lan ◽  
Li Hong Lan ◽  
Tao Xie ◽  
An Ping Liao
Keyword(s):  
Acetic Acid ◽  
Reaction Time ◽  
Cation Exchanger ◽  
Cation Exchange Resin ◽  
Isoamyl Acetate ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Reaction Conditions ◽  
Optimum Reaction

Isoamyl acetate was synthesized from isoamylol and glacial acetic acid with strong acidic cation exchanger as catalyst. The effects of reaction conditions such as acid-alcohol ratio, reaction time, catalyst dosage to esterification reaction have been investigated and the optimum reaction conditions can be concluded as: the molar ratio of acetic acid to isoamylol 0.8:1, reaction time 2h, 25 % of catalyst (quality of acetic acid as benchmark). The conversion rate can reach up to 75.46%. The catalytic ability didn’t reduce significantly after reusing 10 times and the results showed that the catalyst exhibited preferably catalytic activity and reusability.

Study on Synthesis of Ester of Citric Acid and Palmityl Alcohol

2014 ◽  
Vol 900 ◽  
pp. 361-364
Author(s):  
Xiao Hui Wang ◽  
Xi Hua Du ◽  
Li Min Dong
Keyword(s):  
Reaction Time ◽  
Citric Acid ◽  
Cation Exchange ◽  
Sulfonic Acid ◽  
Exchange Resin ◽  
Cation Exchange Resin ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Process Conditions ◽  
Toluene Sulfonic Acid

Esters of Citric acid and palmityl alcohol were synthesized by esterification reaction under catalysis of cation exchange resin and P-toluene sulfonic acid respectively. The effects of amount of catalyst, ratio of raw materials, reaction time and temperature on the synthesis reaction were investigated . The experimental results showed that optimum of process conditions were 1:1~1:1.5 molar ratio of citric acid and palmityl alcohol, reaction temperature of 130~140°C, reaction time of 2 h. Conversion of palmityl alcohol were all more than 90% under 0.3% dosage using p-toluene sulfonic acid as the catalyst, or 0.5% dosage using 721 cation exchange resin with sulfonic acid type as catalyst. The synthesized product had good surface activity.

scholarly journals Simplified Method to Optimize Enzymatic Esters Syntheses in Solvent-Free Systems: Validation Using Literature and Experimental Data

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1357
Author(s):  
Ronaldo Rodrigues de Sousa ◽  
Ayla Sant’Ana da Silva ◽  
Roberto Fernandez-Lafuente ◽  
Viridiana Santana Ferreira-Leitão
Keyword(s):  
Immobilized Lipase ◽  
Solvent Free ◽  
Molar Ratio ◽  
Mathematical Tool ◽  
Enzymatic Esterification ◽  
Reaction Conditions ◽  
Reaction Behavior ◽  
Optimum Reaction ◽  
Interesting Correlation ◽  
Using Data

The adoption of biocatalysis in solvent-free systems is an alternative to establish a greener esters production. An interesting correlation between the acid:alcohol molar ratio and biocatalyst (immobilized lipase) loading in the optimization of ester syntheses in solvent-free systems had been observed and explored. A simple mathematical tool named Substrate-Enzyme Relation (SER) has been developed, indicating a range of reaction conditions that resulted in high conversions. Here, SER utility has been validated using data from the literature and experimental assays, totalizing 39 different examples of solvent-free enzymatic esterifications. We found a good correlation between the SER trends and reaction conditions that promoted high conversions on the syntheses of short, mid, or long-chain esters. Moreover, the predictions obtained with SER are coherent with thermodynamic and kinetics aspects of enzymatic esterification in solvent-free systems. SER is an easy-to-handle tool to predict the reaction behavior, allowing obtaining optimum reaction conditions with a reduced number of experiments, including the adoption of reduced biocatalysts loadings.

scholarly journals Interesterification of Egg-Yolk Phosphatidylcholine with p-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1181
Author(s):  
Magdalena Rychlicka ◽  
Anna Gliszczyńska
Keyword(s):  
Reaction Time ◽  
Design Method ◽  
Immobilized Lipase ◽  
Reaction Medium ◽  
Solvent System ◽  
Novozym 435 ◽  
Molar Ratio ◽  
Binary Solvent ◽  
Methoxycinnamic Acid ◽  
Substrate Molar Ratio

The p-methoxycinnamic acid (p-MCA) is one of the most popular phenylpropanoids, the beneficial impact of which on the human health is well documented in the literature. This compound has shown many valuable activities including anticancer, antidiabetic, and neuro- and hepatoprotective. However, its practical application is limited by its low bioavailability resulting from rapid metabolism in the human body. The latest strategy, aimed at overcoming these limitations, is based on the production of more stability in systemic circulation bioconjugates with phospholipids. Therefore, the aim of this research was to develop the biotechnological method for the synthesis of phospholipid derivatives of p-methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl p-methoxycinnamate (Ep-MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (v/v) were found to be the effective biocatalyst and reaction medium for the synthesis of structured p-MCA phospholipids, respectively. The effects of the other reaction parameters, such as substrate molar ratio, enzyme dosage, and reaction time, on the degree of incorporation of p-MCA into PC were evaluated by use of an experimental factorial design method. The results showed that substrate molar ratio and biocatalyst load have significant effects on the synthesis of p-methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (w/w) of Novozym 435, and 1/10 substrate molar ratio PC/Ep-MCA. Under these parameters, p-methoxycinnamoylated lysophosphatidylcholine (p-MCA-LPC) and p-methoxycinnamoylated phosphatidylcholine (p-MCA-PC) were obtained in isolated yields of 32% and 3% (w/w), respectively.

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