scholarly journals System Development from Organic Solvents to Ionic Liquids for Synthesiz-ing Ascorbyl Esters with Conjugated Linoleic Acids

2012 ◽  
Vol 6 (1) ◽  
pp. 5-12 ◽  
Author(s):  
Zhiyong Yang ◽  
Lise Schultz ◽  
Zheng Guo ◽  
Charlotte Jacobsen ◽  
Xuebing Xu
Keyword(s):  
Ascorbic Acid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
System Development ◽  
Solvent System ◽  
Liquid System ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
Screening Experiments

The aim of this paper is to screen suitable reaction systems for the modification of antioxidants through enzy-matic synthesis. Enzymatic esterification of ascorbic acid with conjugated linoleic acid (CLA) was investigated as a mod-el. Four organic solvents and five different enzymes were evaluated. Results show that only Novozym® 435 turned out to be a useful enzymatic preparation for the production of ascorbyl-CLA ester. The optimum reaction conditions in the or-ganic solvent system were 4 h at 55°C and at a molar ratio of 5 (CLA/ascorbic acid). The esterification reaction was trans-ferred to an ionic liquid system for the purpose of improving solubility of the polar substrate and avoiding the application of organic solvents. From screening experiments, it was evident that only methyltrioctylammonium triflouroacetate (tO-MA·TFA) could provide a proper reaction environment for production of ascorbyl-CLA ester when using Novozym® 435 as biocatalyst. It was possible to significantly increase the productivity (150 g/l) through the increase of ascorbic acid sol-ubility in ionic liquids by super saturation together with the increase of reaction temperature to 70°C, far beyond than that in organic solvents (35 g/l) after preliminary optimizations for both systems.

scholarly journals Conformation and Catalytic Properties Studies ofCandida rugosaLip7 via Enantioselective Esterification of Ibuprofen in Organic Solvents and Ionic Liquids

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Xiang Li ◽  
Shuangshuang Huang ◽  
Li Xu ◽  
Yunjun Yan
Keyword(s):  
Enzyme Activity ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Functional Group ◽  
Candida Rugosa ◽  
Reaction Medium ◽  
Molar Ratio ◽  
Acyl Acceptor ◽  
Carbon Chains ◽  
Ft Ir

Enantioselective esterification of ibuprofen was conducted to evaluate the enzyme activity and ees of lipase fromCandida rugosa(CRL7) in ten conventional organic solvents and three ionic liquids. Different alcohols were tested for selecting the most suitable acyl acceptor due to the fact that the structure of alcohols (branch and length of carbon chains; location of –OH functional group) could affect the enzyme activity and ees. The results of alcohol and solvent selection revealed that 1-isooctanol and isooctane were the best substrate and reaction medium, respectively, because of the highest enzyme activity and ees. Compared with the control, conformational studies via FT-IR indicate that the variations of CRL7’s secondary structure elements are probably responsible for the differences of enzyme activity and ees in the organic solvents and ionic liquids. Moreover, the effects of reaction parameters, such as molar ratio, water content, temperature, and reaction time, in the selected reaction medium, were also examined.

Synthesis and Characterization of 2-Di-methyl Amino Ethyl Laurate Betaine Surfactant

2021 ◽  
Vol 58 (3) ◽  
pp. 220-229
Author(s):  
Rutu Parikh ◽  
Shital Godse ◽  
Nitin Pawar ◽  
Amit Pratap
Keyword(s):  
Coconut Oil ◽  
Enzyme Concentration ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Enzymatic Esterification ◽  
H Nmr ◽  
Temperature Time ◽  
By Products ◽  
Betaine Ester

Abstract The growing need for sustainable natural-based surfactants from green chemistry has led to syntheses of surfactants without the use of solvents and without the generation of by-products when milder manufacturing processes are used. The zwitterionic betaine ester surfactants are derived from natural renewable sources and are biodegradable. In this research, the betaine ester surfactant 2-di-methylaminoethyllaurate betaine was synthesized from 2-di-methylaminoehanol and lauric acid derived from coconut oil in a three-step chemo-enzymatic esterification reaction. The enzymatic process was optimized in terms of operating parameters such as temperature, time, molar ratio and enzyme concentration, resulting in a yield of 87.91%. Structural analysis of the intermediate 2-di-methylaminoethyl laurate as well as the final product 2-di-methylaminoethyl laurate betaine was carried out with FTIR and 1H NMR. The surfactant properties of the betaine were also determined and showed that the betaine can be used as a co-surfactant in many cosmetic and personal care products.

scholarly journals Enzymatic Synthesis of O-Methylated Phenophospholipids by Lipase-Catalyzed Acidolysis of Egg-Yolk Phosphatidylcholine with Anisic and Veratric Acids

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 538 ◽  
Author(s):  
Marta Okulus ◽  
Anna Gliszczyńska
Keyword(s):  
Egg Yolk ◽  
Solvent System ◽  
Biologically Active ◽  
Molar Ratio ◽  
Binary Solvent ◽  
Molar Ratios ◽  
Egg Yolk Phosphatidylcholine ◽  
Screening Experiments ◽  
Acidolysis Reaction ◽  
System 1

Lipase-catalyzed acidolysis reactions of egg-yolk phosphatidylcholine (PC) with anisic (ANISA) and veratric (VERA) acids were investigated to develop a biotechnological method for the production of corresponding biologically active O-methylated phenophospholipids. Screening experiments with four commercially available immobilized lipases indicated that the most effective biocatalyst for the incorporation of ANISA into phospholipids was Novozym 435. None of the tested enzymes were able to catalyze the synthesis of PC structured with VERA. The effects of different solvents, substrate molar ratios, temperature, enzyme loading, and time of the reaction on the process of incorporation of ANISA into the phospholipids were evaluated in the next step of the study. The mixture of toluene/chloroform in the ratio 9:1 (v/v) significantly increased the incorporation of ANISA into PC. The acidolysis reaction was carried out using the selected binary solvent system, 1/15 substrate molar ratio PC/ANISA, 30% (w/w) enzyme load, and temperature of 50 °C afforded after 72 h anisoylated lysophosphatidylcholine (ANISA-LPC) and anisoylated phosphatidylcholine (ANISA-PC) in isolated yields of 28.5% and 2.5% (w/w), respectively. This is the first study reporting the production of ANISA-LPC and ANISA-PC via a one-step enzymatic method, which is an environmentally friendly alternative to the chemical synthesis of these biologically active compounds.

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.

Ionic Liquids as Catalysts for the Acetylation of Camphene

2017 ◽  
Vol 743 ◽  
pp. 355-359
Author(s):  
Svetlana A. Popova ◽  
Irina Yu. Chukicheva
Keyword(s):  
Acetic Acid ◽  
Ionic Liquids ◽  
Ion Exchange Resin ◽  
Effect Of Temperature ◽  
Molar Ratio ◽  
Catalyst Loading ◽  
Esterification Reaction ◽  
The Face ◽  
Environmental Requirements ◽  
Acid Catalyzed

[bnmim]HSO4 and [bnpy]HSO4 are active and environmentally friendly catalysts for the acetylation of camphene with acetic acid. The reaction provides isobornyl acetate with 100% selectivity and 72-86% yield. The effect of temperature, molar ratio camphene/acetic acid, and catalyst loading were investigated. The catalyst can be reused four times without loss of activity. Isobornyl acetate is an important fine chemical and has been used in the field of fragrance, medicine, organic synthesis and cosmetics [1]. It is an intermediary in the synthesis of camphor [2]. Usually it is prepared by an acid-catalized reaction of camphene with acetic acid or acetic anhydride. But this process has serious drawbacks such as the corrosion of equipment, non-recyclability of the catalyst and serious environmental pollution. In the face of increasing environmental requirements, the use of such catalysts becomes unacceptable. Therefore many studies have recently focused on the development of "clean" (green) processes for the production of terpene derivatives with high selectivity. For this purpose, heteropolyacids [3, 4], zeolites [5, 6], solid acid catalysts [7, 8], ion-exchange resin [9-11] were used as catalysts for synthesizing terpene esters. However, these catalysts have drawbacks such as a large ratio of catalyst/substrate, fast deactivation and a selectivity that leaves much to be desired. In the recent years ionic liquids (IL) have been investigated by many researchers as catalysts for different reactions. Due to its low volatility, negligible vapor pressure, reasonable thermal stability, outstanding recyclability and reusability, ionic liquids may be a viable alternative to widely applicable catalysts in the processes of modern synthetic chemistry, the green chemistry [12]. The improvement of the versatility of ionic liquids was achieved by creating acidic functionalized ionic liquids and combining the properties of a reagent and solvent [13]. A number of such ionic liquids were synthesized and successfully applied in the esterification reaction [14-17]. Received that the structure of the IL cation determines the direction of the rearrangement of terpene, whereas the nature of the anion affects the selectivity of the reaction [18, 19]. In the present work, we report the acetylation of camphene with acetic acid catalyzed by imidazolium and pyridinium ionic liquids (Scheme 1). The influence of various reaction parameters, such as the temperature, the molar ratio of camphene/acetic acid and catalyst loading, on the activity of the most active catalyst is also studied.

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 A Preliminary Study: Esterification of Free Fatty Acids (FFA) in Artificially Modified Feedstock Using Ionic Liquids as Catalysts.

2016 ◽  
Vol 11 (2) ◽  
pp. 182
Author(s):  
Nurul Asmawati Roslan ◽  
Mohammad Haniff Che Hasnan ◽  
Norhayati Abdullah ◽  
Syamsul Bahari Abdullah ◽  
Sumaiya Zainal Abidin
Keyword(s):  
Fatty Acids ◽  
Ionic Liquids ◽  
Free Fatty Acids ◽  
Edible Oils ◽  
Batch Reactor ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Preliminary Study ◽  
Hydrogen Sulphate

<p>The exploration of non-edible oils as a feedstock has been positively affect the economic viability of biodiesel production.  Due to the high level of free fatty acid (FFA) in non-edible oils, esterification is needed to remove the acidity to the minimum level before base-catalyzed transesterification.  In this study, 1-hexyl-3-methylimidazolium hydrogen sulphate (HMIMHSO<sub>4</sub>) was self-synthesized and compared with the commercialized ionic liquid, 1-butyl-3-methylimidazolium hydrogen sulphate (BMIMHSO<sub>4</sub>). HMIMHSO<sub>4</sub> and BMIMHSO<sub>4</sub> were characterized by <sup>1</sup>H NMR prior to use in the esterification reaction. The reaction was carried out in a batch reactor and variables such as types of alcohol, oil: alcohol molar ratio, temperature and types of stirring were investigated. The highest conversion for each catalyst was achieved using ethanol as a solvent at the condition of 343 K reaction temperature, 12:1 alcohol to oil ratio in 8 h reaction time. BMIMHSO<sub>4</sub> showed higher conversion (98%) as compared to HMIMHSO<sub>4</sub> with only 82% conversion. Clearly, BMIMHSO<sub>4</sub> shows considerable potential to reduce the FFA in the feedstock as it is exhibit excellent catalytic activity due to lower alkyl chain of BMIMHSO<sub>4</sub> compared to HMIMHSO<sub>4</sub>. Copyright © 2016 BCREC GROUP. All rights reserved</p><p><em>Received: 21<sup>st</sup> January 2016; Revised: 29<sup>th</sup> February 2016; Accepted: 6<sup>th</sup> March 2016</em></p><strong>How to Cite:</strong> Roslan, N.A.,  Che Hasnan M.H., Abdullah, N., Abdullah, S.B., Abidin, S.Z. (2016). A Preliminary Study: Esterification of Free Fatty Acids (FFA) in Artificially Modified Feedstock Using Ionic Liquids as Catalysts. <em>Bulletin of Chemical Reaction Engineering &amp; Catalysis</em>, 11 (2): 182-191 (doi:10.9767/bcrec.11.2.549.182-190)<p><strong>Permalink/DOI:</strong> <a href="http://dx.doi.org/10.9767/bcrec.11.2.549.182-190">http://dx.doi.org/10.9767/bcrec.11.2.549.182-190</a></p>

Electrogenerated NHCs in Organic Synthesis: Ionic Liquids vs Organic Solvents Effects

2021 ◽  
Author(s):  
Fabrizio Vetica ◽  
Martina Bortolami ◽  
Rita Petrucci ◽  
Daniele Rocco ◽  
Marta Feroci
Keyword(s):  
Ionic Liquids ◽  
Organic Synthesis ◽  
Organic Solvents

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.

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