Surfactant assisted production of ricinoleic acid using cross-linked and entrapped porcine pancreas lipase
01 Jun 2021-Journal of Dispersion Science and Technology (Informa UK Limited)-Vol. 42, Iss: 7, pp 947-955
TL;DR: In this paper, the authors studied the impact of surfactant augmentation on the performance of porcine pancreas lipase in castor oil to ricinoleic acid.
Abstract: This work studied hydrolysis of castor oil to ricinoleic acid, catalyzed by immobilized porcine pancreas lipase (PPL) and impact of surfactant on its augmentation. In immobilization of lipase throu...
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168 citations
TL;DR: In this paper , the authors reviewed some reaction stages to the preparation of ricinoleic acid from castor oil, and the most effective technique was the hydrolysis through the use of the enzyme lipozyme TL IM.
Abstract: Castor oil is a vegetable product extracted from Ricinus communis L (castor seed), which is primarily considered an important commercial value for the manufacturing of soaps, lubricants, coatings, etc. It is rich in hydroxylated fatty acids (ricinoleic acid, 89-92%) and is widely used in the cosmetic, pharmaceutical, oleochemical, and agricultural industries. This oil has also been confirmed as a bactericidal, anti-inflammatory, and antiherpetic agents, due to the ricinoleic acid having functional groups, such as -COOH, -OH, and -C=C-. Furthermore, it is converted into various acid derivative compounds with several applications. Therefore, this article reviewed some reaction stages to the preparation of ricinoleic acid from castor oil. Several methods or reaction pathways were employed in the preparation procedure, such as the Twitchell and Colgate-Emery processes, as well as the alkaline catalyzed, transesterification with methyl ricinoleic, and lipase-catalyzed hydrolysis, respectively. Although each of these preparation methods has advantages and disadvantages, the most effective technique was the hydrolysis through the use of the enzyme lipozyme TL IM. Besides being a green method, the conversion rate in the hydrolysis process was 96.2 ± 1.5.
3 citations
TL;DR: In this paper , the catalytic performance of lipase, an interfacially active enzyme, depends on the reaction medium, such as mixture of mixed micelles, which have advantages like improving lipase-substrate interaction, increasing water nucleophilicity, sometimes greater emulsion stability and reduced product inhibition.
Abstract: The catalytic performance of lipase, an interfacially active enzyme, depends on the reaction medium. Novel reaction media like mixed micelles affect lipase catalysis mostly by stabilizing the lipase structure and increasing the substrate solubilization. Nonionic surfactant addition in ionic micelles formed mixed micelles and increased lipase catalysis by lowering detrimental lipase-ionic surfactant hydrophobic and electrostatic interactions. Nonionic/nonionic mixed micelles enhanced activity and enantiomeric selectivity of free lipase but reduced those for immobilized lipase. Nonconventional cationic/cationic, anionic/nonionic/ionic liquid, and substrate/nonionic mixed micelles also improved lipase catalysis. Lipase activity was high in bile salt/surfactant mixed micelles but was low in bile salt/phospholipid mixed micelle. Mixed micelles have advantages like improving lipase-substrate interaction, increasing water nucleophilicity, sometimes greater emulsion stability, and reduced product inhibition. In mixed micelles, increasing the lipase concentration can overcome the problem regarding inaccessibility of insoluble substrates.
2 citations
TL;DR: In this paper , the response surface methodology (RSM) has been used for process optimization to increase the yield of ricinoleic acid and decrease the oil loss, which microorganisms utilizes in biomass production.
Abstract: Ricinoleic acid is a biobased green chemical industrially produced from castor oil. Microbial conversion is a cleaner and greener approach to ricinoleic acid production from castor oil. These processes should be further optimized for a better yield of the product. Aspergillus flavus BU22S was used to convert castor oil into ricinoleic acid. The strain was isolated and identified by molecular biological techniques. It was found to be effective in the biotransformation of castor oil. The ricinoleic acid production and dry cell weight of the fungus were studied as functions of time. In this study, to increase the yield of ricinoleic acid and decrease the oil loss, which microorganisms utilizes in biomass production, response surface methodology (RSM) has been used for process optimization. The central composite design was used to optimize the predictor variables such as oil concentration (% w/v), glucose concentration (% w/v), and calcium chloride concentration (% w/v) to increase the overall yield of ricinoleic acid. A quadratic model was found to be the best fit to predict the responses of the experimental results. The model suggested that the concentrations of oil, glucose, and calcium chloride should be lower in order to increase the ricinoleic acid yield and minimize the oil loss. The bench scale studies of optimized conditions from RSM were also conducted. The yield of ricinoleic acid in batch and fed-batch culture studies was also compared. The yield of the ricinoleic acid in batch culture was 21.67 g/kg of total oil. The yield of ricinoleic acid in fed-batch culture in the absence of an external air supply was 46.77 g/kg of total oil. In this case, the oil loss was also reduced to only 12%.
References
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TL;DR: Lipase from Rhizomucor miehei was immobilized onto chitosan support in the presence of some surfactants added at low levels using two different strategies and the derivatives obtained showed high catalytic activity and excellent thermal stability at 60° and 37 °C.
Abstract: Lipase from Rhizomucor miehei (RML) was immobilized onto chitosan support in the presence of some surfactants added at low levels using two different strategies. In the first approach, the enzyme was immobilized in the presence of surfactants on chitosan supports previously functionalized with glutaraldehyde. In the second one, after prior enzyme adsorption on chitosan beads in the presence of surfactants, the complex chitosan beads-enzyme was then cross-linked with glutaraldehyde. The effects of surfactant concentrations on the activities of free and immobilized RML were evaluated. Hexadecyltrimethylammonium bromide (CTAB) promoted an inhibition of enzyme activity while the nonionic surfactant Triton X-100 caused a slight increase in the catalytic activity of the free enzyme and the derivatives produced in both methods of immobilization. The best derivatives were achieved when the lipase was firstly adsorbed on chitosan beads at 4 °C for 1 h, 220 rpm followed by cross-link the complex chitosan beads-enzyme with glutaraldehyde 0.6% v.v−1 at pH 7. The derivatives obtained under these conditions showed high catalytic activity and excellent thermal stability at 60° and 37 °C. The best derivative was also evaluated in the synthesis of two flavor esters namely methyl and ethyl butyrate. At non-optimized conditions, the maximum conversion yield for methyl butyrate was 89%, and for ethyl butyrate, the esterification yield was 92%. The results for both esterifications were similar to those obtained when the commercial enzyme Lipozyme® and free enzyme were used in the same reaction conditions and higher than the one achieved in the absence of the selected surfactant.
57 citations
TL;DR: In this paper, the authors used a three-bladed propeller stirrer as mixing device to obtain an estolide of ricinoleic acid with an acid number of 65.
Abstract: Candida rugosa lipase has been shown to have sufficient activity to catalyse the enzymatic synthesis of ricinoleic acid estolides in a batch reactor. The water requirements of the reactor change during the reaction: at the beginning of the process a minimum amount of water is necessary but, later, the reaction mixture must be dried out to obtain an estolide with a high degree of condensation. The influence on the reaction rate of variables, such as water content, enzyme concentration and mixing devices, was established and optimised. Using an initial water content of 144,000 ppm and a lipase concentration of 13.33 mg E/g ricin, and maintaining the temperature at 40 °C by mean of hot air circulation and using a three-bladed propeller stirrer as mixing device, an estolide of ricinoleic acid with an acid number of 65 was obtained in 48 h.
51 citations
"Surfactant assisted production of r..." refers methods in this paper
...Ricinoleic acid was detected by its absorbance at 205 nm with the help of UV detector.([21]) The recovery of ricinoleic acid was calculated as:...
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TL;DR: In this article, three commercial lipases were studied (from Thermomyces lanuginosa (TLL), Candida Antarctica fraction B (CALB) and Lecitase (LEC)).
Abstract: Most of lipases are in equilibrium between a majority inactive closed form and a minority active open form in aqueous media. Perhaps, a certain stabilization of these open forms of lipases could be achieved in the presence of cosolvents or surfactants in the reaction medium. Three commercial lipases were studied (from Thermomyces lanuginosa (TLL), Candida Antarctica fraction B (CALB) and Lecitase (LEC)). Different derivatives were tested: TLL and LEC were adsorbed on an anionic exchanger and their activity strongly depends on the equilibrium between their open and closed form and CALB was adsorbed on a hydrophobic support when the open form was already stabilized by the support. Derivatives ionically adsorbed were hyperactivated by surfactans as well as by cosolvents: the activity of LEC increased 12 times in the presence of 15–20% of ethanol. CALB adsorbed on hydrophobic supports was hardly hyperactivated and even it was inhibited. The modification of the rate of covalent modification of the catalytic Ser seems to confirm that the observed hyperactivations were due to a stabilization of the open form of the adsorbed lipases (TLL and LEC). The hydrolysis of sardine oil was also studied in the presence or absence of surfactants and cosolvents. An interesting improvement in the ability of derivatives to discriminate the release of eicosipentaenic acid (EPA) and docosahexaenicacid (DHA) was found.
43 citations
"Surfactant assisted production of r..." refers background in this paper
...Surfactant-lipase interaction varied significantly with type of surfactant, whether the lipase was free([10]) or immobilized.([11]) The effect of surfactant on lipase depended on type of substrate also....
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TL;DR: This is the first report on the application of response surface methodology for optimizing surfactant enhanced ricinoleic acid production using C. rugosa lipase and the most important variable was pH, whereas enzyme and buffer concentrations also showed pronounced effect on response.
Abstract: In this study, ricinoleic acid was produced on surfactant enhanced castor oil hydrolysis using Candida rugosa lipase. The most effective surfactant was Span 80. Employing fractional factorial design, the most suitable temperature and surfactant concentration were found to be 31 degrees C and 0.257% (w/w in buffer) respectively whereas pH, enzyme concentration, buffer concentration and agitation were identified as the most significant independent variables. A 2(4) full factorial central composite design was applied and the optimal conditions were found to be pH 7.0, enzyme concentration 7.42 mg/g oil, buffer concentration 0.20 g/g oil and agitation 1400 rpm with the maximum response of 76% in 4 h. The most important variable was pH, whereas enzyme and buffer concentrations also showed pronounced effect on response. This is the first report on the application of response surface methodology for optimizing surfactant enhanced ricinoleic acid production using C. rugosa lipase.
42 citations
"Surfactant assisted production of r..." refers background or methods in this paper
...2020 Taylor & Francis Group, LLC have substrate and/or product specificity coupled with a high enantioselectivity and regioselectivity;[4] Goswami et al.[5] applied free Candida rugosa lipase (CRL) in castor oil hydrolysis to ricinoleic acid....
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...Goswami et al.([8]) found optimal conditions as 31 C, pH 7, 7....
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...Ranges of concentration of lipase, pH and surfactant concentration were selected based on the studies by Goswami et al.([5,8]) Table 3 represents central composite design matrix of coded test variables and corresponding response (% ricinoleic acid recovery) in presence of cross-linked and entrapped lipase (PPL) and Span 80 (nonionic surfactant)....
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...In presence of Span 80 (nonionic surfactant), free CRL showed better catalytic ability to produce ricinoleic acid from castor oil.([8]) Immobilized lipase is better than free lipase as a catalyst for its higher thermostability, recyclability, etc....
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...Ranges of concentration of lipase, pH and surfactant concentration were selected based on the studies by Goswami et al.[5,8] Table 3 represents central composite design matrix of coded test variables and corresponding response (% ricinoleic acid recovery) in presence of cross-linked and entrapped lipase (PPL) and Span 80 (nonionic surfactant)....
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TL;DR: This is the first report on the application of response surface methodology in castor oil hydrolysis using C. rugosa lipase with higher percentage conversion in 6 h.
Abstract: In this study, response surface methodology was applied to optimize process variables like temperature, pH, enzyme concentration (mg/g oil), and buffer concentration (g/g oil) for hydrolysis of castor oil using Candida rugosa lipase. A 2 4 full factorial central composite design was used to develop the quadratic model that was subsequently optimized and the optimal conditions were as follows: temperature 40 °C, pH 7.72, enzyme concentration 5.28 mg/g oil, buffer concentration 1 g/g oil and there was 65.5% conversion in 6 h. These predicted optimal conditions agreed well with the experimental results. This is the first report on the application of response surface methodology in castor oil hydrolysis using C. rugosa lipase with higher percentage conversion in 6 h.
34 citations
"Surfactant assisted production of r..." refers background or methods in this paper
...2020 Taylor & Francis Group, LLC have substrate and/or product specificity coupled with a high enantioselectivity and regioselectivity;[4] Goswami et al.[5] applied free Candida rugosa lipase (CRL) in castor oil hydrolysis to ricinoleic acid....
[...]
...have substrate and/or product specificity coupled with a high enantioselectivity and regioselectivity;([4]) Goswami et al.([5]) applied free Candida rugosa lipase (CRL) in castor oil hydrolysis to ricinoleic acid....
[...]
...Ranges of concentration of lipase, pH and surfactant concentration were selected based on the studies by Goswami et al.([5,8]) Table 3 represents central composite design matrix of coded test variables and corresponding response (% ricinoleic acid recovery) in presence of cross-linked and entrapped lipase (PPL) and Span 80 (nonionic surfactant)....
[...]
...Ranges of concentration of lipase, pH and surfactant concentration were selected based on the studies by Goswami et al.[5,8] Table 3 represents central composite design matrix of coded test variables and corresponding response (% ricinoleic acid recovery) in presence of cross-linked and entrapped lipase (PPL) and Span 80 (nonionic surfactant)....
[...]
...Goswami et al.[8] found optimal conditions as 31 C, pH 7, 7.42mg CRL/g oil, 0.20 g buffer/g oil, 0.257% Span 80 (w/w in buffer) and 1400 rpm with 76% ricinoleic acid in 4 h....
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