Studies on the Immobilized-Lipase-Catalyzed Esterification of Alkyl Oleates in Solvent-Free Systems

2013 ◽  
Vol 645 ◽  
pp. 19-23 ◽  
Author(s):  
Hui Zhong ◽  
Zheng Fang ◽  
Bao Hua Zou ◽  
Xin Li ◽  
Kai Guo
Keyword(s):  
Oleic Acid ◽  
Low Temperature ◽  
High Selectivity ◽  
Immobilized Lipase ◽  
Enzyme Concentration ◽  
Molar Ratio ◽  
High Yield ◽  
Secondary Alcohols ◽  
Tertiary Alcohols ◽  
Candida Sp

The esterification of oleic acid with alkyl alcohols in solv ent-free systems was catalyzed by an immobilized lipase from Candida sp . 99-125. The influence of several factors, including enzyme concentration, temperature, molar ratio between oleic acid and alkyl alcohols, and structure of alcohol was also investigated. The results indicated that the reactions catalyzed by lipase at 20 o C, in the presence of 3% (w/w) lipase, on the molar ratio of 1:1 between oleic acid and alcohols, afforded products in high yield. It showed high selectivity to primary and low selectivity to secondary alcohols and tertiary alcohols because of the sterically hindered effect. Methanol has certain toxicity on the activity of the lipase. The lipase from Candida sp. 99-125 was identified to be an effective catalyst in the esterification of alcohol and oleic acid at low temperature.

Studies on the Esterification Synthesis of Alkyl Oleates in Solvent-Free System by Candida Sp. Lipase

2013 ◽  
Vol 634-638 ◽  
pp. 599-603
Author(s):  
Hui Zhong ◽  
Zheng Fang ◽  
Bao Hua Zou ◽  
Xin Li ◽  
Kai Guo
Keyword(s):  
Oleic Acid ◽  
High Selectivity ◽  
Enzyme Concentration ◽  
Solvent Free ◽  
Hydroxyl Group ◽  
Molar Ratio ◽  
High Yield ◽  
Free System ◽  
Candida Sp ◽  
Solvent Free System

The alkyl oleates were prepared by esterification of oleic acid with alkyl alcohols catalyzed by the lipase from Candida sp. 99-125 in solvent-free system. The influence of several factors, including enzyme concentration, temperature, molar ratio between oleic acid and alkyl alcohols and the structures of alcohols, was also investigated. The results indicated that the reactions catalyzed by lipase at 20 oC, in the presence of 5% (w/w) lipase, on the molar ratio of 1:1 between oleic acid and alcohols, afforded products in high yield and showed high selectivity to the alcohols with less hindrance on hydroxyl group. The lipase from Candida sp. 99-125 was identified to be an effective catalyst in the esterification of alcohol and oleic acid at low temperature.

scholarly journals Low-Temperature Esterification to Produce Oleic Acid-Based Wax Esters Catalyzed by 4-Dodecylbenzenesulfonic Acid

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1471
Author(s):  
Zhenzhen Li ◽  
Wei Liu ◽  
Guolong Yang
Keyword(s):  
Oleic Acid ◽  
Low Temperature ◽  
Inhibitory Effect ◽  
Wax Esters ◽  
Molar Ratio ◽  
Efficient Catalyst ◽  
Dodecylbenzenesulfonic Acid ◽  
Effect Of Water ◽  
Solvent Free Conditions ◽  
Increasing Temperature

Synthesized oleic acid-based wax esters (e.g., cetyl oleate), which can replace spermaceti oil or jojoba oil, have been widely used in the cosmetic, pharmaceutical and other industries. In this work, 4-dodecylbenzenesulfonic acid (DBSA) has been successfully used as an efficient catalyst to synthesize oleic acid-based wax esters through esterification at 40 °C under solvent-free conditions. A 93.6% conversion rate of cetyl alcohol was obtained under optimal conditions: 10 mol% DBSA, a molar ratio of 1.3:1 oleic acid to alcohol, a reaction temperature 40 °C and a reaction time of 4 h. The effect of water content on esterification was investigated, and it was found that the inhibitory effect of water decreased significantly with increasing temperature. Moreover, DBSA-catalyzed esterification could be applied in the production of various oleic acid-based wax esters and excellent conversion (>90%) to esters was obtained under such mild conditions. DBSA-catalyzed low-temperature esterification is an efficient method for the production of liquid wax esters.

scholarly journals Statistical Optimization of Biodiesel Production from Salmon Oil via Enzymatic Transesterification: Investigation of the Effects of Various Operational Parameters

Processes ◽  
2021 ◽  
Vol 9 (4) ◽  
pp. 700
Author(s):  
Vegneshwaran V. Ramakrishnan ◽  
Deepika Dave ◽  
Yi Liu ◽  
Winny Routray ◽  
Wade Murphy
Keyword(s):  
Atlantic Salmon ◽  
Immobilized Lipase ◽  
Enzyme Concentration ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
Operational Parameters ◽  
Enzymatic Transesterification ◽  
Optimum Parameters ◽  
Response Surface Modelling ◽  
The Relationship

The enzymatic transesterification of Atlantic salmon (Salmo salar) oil was carried out using Novozym 435 (immobilized lipase from Candida antartica) to produce biodiesel. A response surface modelling design was performed to investigate the relationship between biodiesel yield and several critical factors, including enzyme concentration (5, 10, or 15%), temperature (40, 45, or 50 °C), oil/alcohol molar ratio (1:3, 1:4, or 1:5) and time (8, 16, or 24 h). The results indicated that the effects of all the factors were statistically significant at p-values of 0.000 for biodiesel production. The optimum parameters for biodiesel production were determined as 10% enzyme concentration, 45 °C, 16 h, and 1:4 oil/alcohol molar ratio, leading to a biodiesel yield of 87.23%. The step-wise addition of methanol during the enzymatic transesterification further increased the biodiesel yield to 94.5%. This is the first study that focused on Atlantic salmon oil-derived biodiesel production, which creates a paradigm for valorization of Atlantic salmon by-products that would also reduce the consumption and demand of plant oils derived from crops and vegetables.

scholarly journals Enzymatic Synthesis of Formate Ester through Immobilized Lipase and Its Reuse

Polymers ◽  
2020 ◽  
Vol 12 (8) ◽  
pp. 1802 ◽  
Author(s):  
Yesol Baek ◽  
Jonghwa Lee ◽  
Jemin Son ◽  
Taek Lee ◽  
Abdus Sobhan ◽  
...  
Keyword(s):  
Reaction Temperature ◽  
Enzymatic Synthesis ◽  
Immobilized Enzyme ◽  
Immobilized Lipase ◽  
Enzymatic Reaction ◽  
Optimization Method ◽  
Enzyme Concentration ◽  
Novozym 435 ◽  
Molar Ratio ◽  
Optimal Conditions

Octyl formate is an important substance used in the perfume industry in products such as cosmetics, perfumes, and flavoring. Octyl formate is mostly produced by chemical catalysts. However, using enzymes as catalysts has gathered increasing interest due to their environment-friendly proprieties. In the present study, we aimed to identify the optimal conditions for the synthesis of octyl formate through immobilized enzyme-mediated esterification. We investigated the effects of enzymatic reaction parameters including the type of immobilized enzyme, enzyme concentration, molar ratio of reactants, reaction temperature, and type of solvent using the optimization method of one factor at a time (OFAT). The maximum conversion achieved was 96.51% with Novozym 435 (15 g/L), a 1:7 formic acid to octanol ratio, a reaction temperature of 40 °C, and with 1,2-dichloroethane as solvent. Moreover, we demonstrated that the Novozym 435 can be reused under the optimal conditions without affecting the octyl formate yield, which could help reduce the economic burden associated with enzymatic synthesis.

Esterification of Oleic Acid and Bioalcohols Using Immobilized Lipase

2013 ◽  
Vol 724-725 ◽  
pp. 1154-1157 ◽  
Author(s):  
Sawittree Mulalee ◽  
Jiranan Chanprasert ◽  
Piboon Kerdpoksup ◽  
Netnapa Sawangpanya Sawangpanya ◽  
Muenduen K.M. Phisalaphong
Keyword(s):  
Oleic Acid ◽  
Fatty Acid ◽  
Immobilized Lipase ◽  
Biodiesel Production ◽  
Novozym 435 ◽  
Molar Ratio ◽  
Optimal Conditions ◽  
Free System ◽  
Solvent Free System ◽  
Significant Attention

Biodiesel has been receiving significant attention as a renewable and nonpolluting fuel. In this study, oleic acid and bioalcohols (ethanol and butanol) were used as substrates for biodiesel production. The reactions were performed in a solvent-free system using immobilized lipase (Novozym 435) as biocatalyst in a batch esterification process. The optimal conditions were 45°C, oleic acid to alcohol molar ratio of 1:2, Novozym 435 loading at 5% based on oleic acid weight and 250 rpm, in which the free fatty acid (FFA) conversion at 91.0% was obtained after 12 hours of the reaction.

4-Hydroxy Pyridinium Triflate@SiO2 Nanoparticles as a Novel Efficient Catalyst for Fries Rearrangement of Aryl Esters with High Selectivity

2020 ◽  
Vol 17 (8) ◽  
pp. 654-660
Author(s):  
Shermineh Sadat Ghalehbandi ◽  
Dadkhoda Ghazanfari ◽  
Sayed Ali Ahmadi ◽  
Enayatollah Sheikhhosseini
Keyword(s):  
High Selectivity ◽  
Sio2 Nanoparticles ◽  
High Yield ◽  
Synthetic Method ◽  
Functionalized Silica ◽  
Efficient Catalyst ◽  
Fries Rearrangement ◽  
Free Condition ◽  
Solvent Free Condition ◽  
Work Up

Introduction: We developed a simple, fast and new method for the Fries rearrangement of aryl esters. Materials and Methods: 4-Hydroxy pyridinium triflate functionalized silica is a very efficient, reusable and economically available catalyst for the Fries rearrangement in solvent-free condition and under microwave irradiation. Results and Discussion: Also, a notable selectivity was observed in the presence of 4-hydroxy pyridinium triflate functionalized silica. Conclusion: Selectivity, shorter reaction time, high yield, and easy work-up are advantages of this synthetic method.

scholarly journals Promising Immobilization of Industrial-Class Phospholipase A1 to Attain High-Yield Phospholipids Hydrolysis and Repeated Use with Optimal Water Content in Water-in-Oil Microemulsion Phase

2021 ◽  
Vol 11 (4) ◽  
pp. 1456
Author(s):  
Yusuke Hayakawa ◽  
Ryoichi Nakayama ◽  
Norikazu Namiki ◽  
Masanao Imai
Keyword(s):  
Water Content ◽  
Reaction Rate ◽  
Enzyme Reaction ◽  
Initial Reaction Rate ◽  
Industrial Applications ◽  
Molar Ratio ◽  
High Yield ◽  
Initial Reaction ◽  
Phospholipase A1 ◽  
Repeated Use

In this study, we maximized the reactivity of phospholipids hydrolysis with immobilized industrial-class phospholipase A1 (PLA1) at the desired water content in the water-in-oil (W/O) microemulsion phase. The optimal hydrophobic-hydrophilic condition of the reaction media in a hydrophobic enzyme reaction is critical to realize the maximum yields of enzyme activity of phospholipase A1. It was attributed to enzymes disliking hydrophobic surroundings as a special molecular structure for reactivity. Immobilization of PLA1 was successfully achieved with the aid of a hydrophobic carrier (Accurel MP100) combination with the treatment using glutaraldehyde. The immobilized yield was over 90% based on simple adsorption. The hydrolysis reaction was kinetically investigated through the effect of glutaraldehyde treatment of carrier and water content in the W/O microemulsion phase. The initial reaction rate increased linearly with an increasing glutaraldehyde concentration and then leveled off over a 6% glutaraldehyde concentration. The initial reaction rate, which was predominantly driven by the water content in the organic phase, changed according to a typical bell-shaped curve with respect to the molar ratio of water to phospholipid. It behaved in a similar way with different glutaraldehyde concentrations. After 10 cycles of repeated use, the reactivity was well sustained at 40% of the initial reaction rate and the creation of the final product. Accumulated yield after 10 times repetition was sufficient for industrial applications. Immobilized PLA1 has demonstrated potential as a biocatalyst for the production of phospholipid biochemicals.

scholarly journals Synthesis and Characterization of Partially Renewable Oleic Acid-Based Ionomers for Proton Exchange Membranes

Polymers ◽  
2020 ◽  
Vol 13 (1) ◽  
pp. 130
Author(s):  
Carlos Corona-García ◽  
Alejandro Onchi ◽  
Arlette A. Santiago ◽  
Araceli Martínez ◽  
Daniella Esperanza Pacheco-Catalán ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Proton Conductivity ◽  
Electrochemical Impedance ◽  
Proton Exchange Membranes ◽  
Proton Exchange ◽  
Molar Ratio ◽  
Aromatic Diamines ◽  
Chemical Structures ◽  
Long Chain

The future availability of synthetic polymers is compromised due to the continuous depletion of fossil reserves; thus, the quest for sustainable and eco-friendly specialty polymers is of the utmost importance to ensure our lifestyle. In this regard, this study reports on the use of oleic acid as a renewable source to develop new ionomers intended for proton exchange membranes. Firstly, the cross-metathesis of oleic acid was conducted to yield a renewable and unsaturated long-chain aliphatic dicarboxylic acid, which was further subjected to polycondensation reactions with two aromatic diamines, 4,4′-(hexafluoroisopropylidene)bis(p-phenyleneoxy)dianiline and 4,4′-diamino-2,2′-stilbenedisulfonic acid, as comonomers for the synthesis of a series of partially renewable aromatic-aliphatic polyamides with an increasing degree of sulfonation (DS). The polymer chemical structures were confirmed by Fourier transform infrared (FTIR) and nuclear magnetic resonance (1H, 13C, and 19F NMR) spectroscopy, which revealed that the DS was effectively tailored by adjusting the feed molar ratio of the diamines. Next, we performed a study involving the ion exchange capacity, the water uptake, and the proton conductivity in membranes prepared from these partially renewable long-chain polyamides, along with a thorough characterization of the thermomechanical and physical properties. The highest value of the proton conductivity determined by electrochemical impedance spectroscopy (EIS) was found to be 1.55 mS cm−1 at 30 °C after activation of the polymer membrane.

scholarly journals Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3317
Author(s):  
Maria Carolina Pereira Gonçalves ◽  
Jéssica Cristina Amaral ◽  
Roberto Fernandez-Lafuente ◽  
Ruy de Sousa Junior ◽  
Paulo Waldir Tardioli
Keyword(s):  
Oleic Acid ◽  
Methyl Ethyl Ketone ◽  
Molar Ratio ◽  
Methyl Ethyl ◽  
Sugar Ester ◽  
Molar Ratios ◽  
Emulsion Capacity ◽  
Ping Pong ◽  
Commercial Sugar ◽  
Repeated Use

In this paper, we have performed the Lipozyme 435-catalyzed synthesis of xylose oleate in methyl ethyl ketone (MEK) from xylose and oleic acid. The effects of substrates’ molar ratios, reaction temperature, reaction time on esterification rates, and Lipozyme 435 reuse were studied. Results showed that an excess of oleic acid (xylose: oleic acid molar ratio of 1:5) significantly favored the reaction, yielding 98% of xylose conversion and 31% oleic acid conversion after 24 h-reaction (mainly to xylose mono- and dioleate, as confirmed by mass spectrometry). The highest Lipozyme 435 activities occurred between 55 and 70 °C. The predicted Ping Pong Bi Bi kinetic model fitted very well to the experimental data and there was no evidence of inhibitions in the range assessed. The reaction product was purified and presented an emulsion capacity close to that of a commercial sugar ester detergent. Finally, the repeated use of Lipozyme 435 showed a reduction in the reaction yields (by 48 and 19% in the xylose and oleic acid conversions, respectively), after ten 12 h-cycles.

Selection of high-quality sperm with thousands of parallel channels

Lab on a Chip ◽  
2021 ◽  
Author(s):  
Mohammad Simchi ◽  
Jason Riordon ◽  
Jae Bem You ◽  
Yihe Wang ◽  
Sa Xiao ◽  
...  
Keyword(s):  
Clinical Practice ◽  
High Selectivity ◽  
High Yield ◽  
Sperm Selection ◽  
High Quality ◽  
Parallel Channels ◽  
Selection Of

A 3D-structured sperm selection device is presented that achieves both high selectivity and high yield via thousands of parallel channels. The device significantly outperforms the best clinical practice by selecting ∼100 000 of higher-quality sperm.

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