Optimization of the Lipase Catalyzed Production of Structured Acylglycerols With Polyunsaturated Fatty Acids Isolated From Sardine Oil

In the present work, direct enzyme-catalyzed esterification of n-3 polyunsaturated fatty acids (n-3 PUFA) isolated from sardine oil was optimized to obtain structured acyglycerols. A n-3 PUFA concentrate was prepared by urea crystallization of refined sardine oil and esterification was carried out mixing free fatty acids and glycerol at different molar ratios (M = 0.48, 1.5, 3.0, 4.5 and 5.52 mol/mol), using an immobilized lipase preparation from Candida antarctica (NV-435) at different temperatures (T = 38, 45, 55, 65 and 72 °C) and reaction times (t = 0.7, 2.75, 5.75, 8.75 and 10.8 h) in a rotatable central composition design. The degree of esterification was determined by analysis of the acylglycerides produced, using liquid chromatography (HPLC-ELSD). Optimization by response surface methodology (RSM) showed that in order to obtain higher esterification levels of n-3 PUFA to glycerol (99.5%), a molar ratio of 1.3 mol n-3 PUFA/mol glycerol, time 8.3 h and temperature 38 °C, are required. However, results of this work show that it is possible to drive the reaction to any determined product (MAG, DAG or TAG) by modifying the reaction conditions.

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Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids

Pure and Applied Chemistry ◽

10.1515/pac-2016-0920 ◽

2016 ◽

Vol 88 (12) ◽

pp. 1191-1201 ◽

Cited By ~ 5

Author(s):

Diana Aparaschivei ◽

Anamaria Todea ◽

Iulia Păuşescu ◽

Valentin Badea ◽

Mihai Medeleanu ◽

...

Keyword(s):

Fatty Acids ◽

Degradation Products ◽

Hydroxy Fatty Acids ◽

Molar Ratio ◽

Molar Ratios ◽

Chemical Structures ◽

Buffer Solutions ◽

Different Temperatures ◽

Ft Ir ◽

Candida Antarctica B

AbstractNew copolymers of ε-caprolactone with three hydroxy-fatty acids, 12-hydroxy stearic acid, 16-hydroxyhexadecanoic acid and ricinoleic acid, were synthesized by catalytic polyesterification. The reactions were carried out in solvent-free systems and in organic solvents as well, using tin(II) 2-ethylhexanoate as catalyst, at different temperatures and molar ratios of the comonomers. Cyclic and linear polymeric products with medium molar weight of about 2000 Da have been synthesized and their chemical structures were confirmed by FT-IR, NMR and MALDI-TOF MS analysis. The synthesis parameters were optimized and the ε-caprolactone/hydroxy acid molar ratio was set as 5:1, according to mass spectrometry results. The biodegradability of the newly synthesized polymers was studied in the presence of Candida antarctica B lipase in phosphate buffer solutions (pH=7.4), at 37°C. The weight-loss profile emphasized the degradation of the 16-hydroxyhexadecanoic acid based polymer samples at more than 50% of their initial weight in 18 days of incubation in the presence of the lipase. The composition of the degradation products was assessed using the GC-MS technique and displayed residues of the comonomers moieties.

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Production of biodiesel by esterification and transesterification from waste cooking oils

Revista de la Facultad de Agronomía, Universidad del Zulia ◽

10.47280/revfacagron(luz).v38.n1.06 ◽

2020 ◽

Vol 38 (1) ◽

pp. 105-127

Author(s):

Elsy Arenas ◽

Aidin Urribarrí ◽

John Sánchez ◽

Marisela Rincón ◽

Karina Martínez ◽

...

Keyword(s):

Fatty Acids ◽

Free Fatty Acids ◽

Fast Food ◽

Methyl Esters ◽

Reaction Times ◽

Molar Ratio ◽

Reaction Conditions ◽

Waste Cooking Oils ◽

Hcl Concentration ◽

Cooking Oils

Large quantities of used vegetable oils (AVUs) are generated annually, as a result of food preparation, which can cause contamination of waters and soils, if they are not disposed of properly, but in turn have great potential in the production of biodiesel. In this work, the AVU collected from fast food establishments were subjected to an esterification pretreatment, varying the reaction conditions, molar ratio, catalyst concentration and time, to decrease the content of free fatty acids generated in the frying processes; after an alkaline transesterification. The initial acidity of the AVUs (10,08 ± 0,22 %) was found to drop below 1 % during esterification at 60 °C and 100 rpm, with RMAVU:MeOH of 1: 7 and HCl concentration of 0.3 % v/v, with a conversion of free fatty acids (FFA) to methyl esters of 94.48 and 98.61 % for reaction times of 4 and 6 hours, respectively. The previously esterified AVUs were subjected to a transesterification process with KOH as a catalyst in the presence of methanol, at 60 °C and 100 rpm, finding that the biodiesel produced was a mixture composed of the methyl esters of linoleic acids (57 %), palmitic (14 %), oleic (22 %), stearic (4 %) and elaidic (3 %). The highest concentration of methyl esters (93,797 ± 0.685 g.L-1) was obtained when using the esterified AVU during 6 hours of reaction. FTIR spectra confirmed the conversion of fatty acids to methyl esters, so this product could be used as a biofuel.

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

Catalysts ◽

10.3390/catal11111357 ◽

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.

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Efficient synthesis of pyrido[2,3-d]pyrimidine-7-carboxylic acids catalyzed by a TiO2/SiO2 nanocomposite in aqueous media at room temperature

Zeitschrift für Naturforschung B ◽

10.1515/znb-2018-0076 ◽

2018 ◽

Vol 73 (9) ◽

pp. 641-645 ◽

Cited By ~ 1

Author(s):

Sepehr Sadegh-Samiei ◽

Shahrzad Abdolmohammadi

Keyword(s):

Heterogeneous Catalyst ◽

Carboxylic Acids ◽

Room Temperature ◽

Aqueous Media ◽

Reaction Times ◽

Molar Ratio ◽

Efficient Synthesis ◽

Reaction Conditions ◽

Moderate Reaction ◽

Recyclable Heterogeneous Catalyst

AbstractA novel and efficient synthesis of eight 5-aryl-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-7-carboxylic acids using a TiO2/SiO2 nanocomposite with a molar ratio of 1:1 as a recyclable heterogeneous catalyst is described. The desired products, five of which are new, are formed in short reaction times (2–3 h) with high to excellent yields (94%–98%) under very moderate reaction conditions (room temperature, aqueous media).

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Concentration of omega 3-polyunsaturated fatty acids of seal blubber oil by urea complexation: optimization of reaction conditions

Food Chemistry ◽

10.1016/s0308-8146(98)00153-8 ◽

1999 ◽

Vol 65 (1) ◽

pp. 41-49 ◽

Cited By ~ 115

Author(s):

Udaya N Wanasundara ◽

Fereidoon Shahidi

Keyword(s):

Fatty Acids ◽

Polyunsaturated Fatty Acids ◽

Omega 3 ◽

Reaction Conditions ◽

Urea Complexation ◽

Seal Blubber Oil

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Esterification of polyunsaturated fatty acids by various forms of immobilized lipase from Rhizomucor miehei

Lipids ◽

10.1007/s11745-000-545-7 ◽

2000 ◽

Vol 35 (4) ◽

pp. 461-466 ◽

Cited By ~ 2

Author(s):

Yoshitsugu Kosugi ◽

Prodyut Kumar Roy ◽

Qinglong Chang ◽

Cao Shu-gui ◽

Makoto Fukatsu ◽

...

Keyword(s):

Fatty Acids ◽

Polyunsaturated Fatty Acids ◽

Immobilized Lipase ◽

Rhizomucor Miehei

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Enzymatic Concentration of n−3 Polyunsaturated Fatty Acids from Indian Sardine Oil

Biotechnology and Biochemical Engineering ◽

10.1007/978-981-10-1920-3_15 ◽

2016 ◽

pp. 137-143 ◽

Cited By ~ 1

Author(s):

Charanyaa Sampath ◽

N. Anita ◽

B. D. Prasanna ◽

Iyyaswami Regupathi

Keyword(s):

Fatty Acids ◽

Polyunsaturated Fatty Acids ◽

Sardine Oil

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The Influence of Interesterification of Structured Fats on the Properties of the Fat Blends

Czech Journal of Food Sciences ◽

10.17221/1088-cjfs ◽

2009 ◽

Vol 27 (Special Issue 1) ◽

pp. S293-S296

Author(s):

M. Tesařová ◽

M. Zárubová ◽

V. Filip ◽

V. Spěváčková ◽

J. Šmidrkal

Keyword(s):

Fatty Acids ◽

Saturated Fatty Acids ◽

Point Of View ◽

Molar Ratio ◽

Medium Chain ◽

Molar Ratios ◽

Lower Molar ◽

Long Chain ◽

Soft Margarines

Consistency, rheology and melting/solidification characteristics of model fat blends (FB) on the basis of interesterified structured fats (SF) are discussed. SF were prepared by an alkaline catalysed random interesterification of fully hydrogenated coconut (FHCO) and high-erucic rapeseed (FHHERO) oils with variable molar ratio (2:1; 1.4:1; 1:1; 1:1.4 and 1:2) of the medium chain (M; C8:0–C14:0) and long chain (L; C16:0–C22:0) saturated fatty acids (FA) to find out, if stearic/arachic/behenic acids can substitute palmitic/stearic acids in SF. This substitution in SF is possible at molar ratios M:L 2:1 and 1.4:1 from the point of view of melting and solidifications characteristics as well as consistency and rheology for soft margarines. Lower molar ratios of M:L are suitable for FB of shortenings. The final ratio of saturated:unsaturated FA in FB for soft-margarines is 33:67 w/w.

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