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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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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168 citations
"Surfactant assisted production of r..." refers methods in this paper
...Determination of extent of hydrolysis On the basis of acid and saponification value, the ‘% Hydrolysis’ was calculated as:([19]) % Hydrolysis 1⁄4 A:V: 100 S:V: [2] where, ‘Saponification Value’ (SV) of castor oil was found as 180.([20])...
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154 citations
TL;DR: Examples of the various effects of surfactants on lipase structure, activity and inhibition are reviewed, which show how complex the various equilibria involved in the lipolysis reaction tend to be.
Abstract: Lipase inhibitors are the main anti-obesity drugs prescribed these days, but the complexity of their mechanism of action is making it difficult to develop new molecules for this purpose. The efficacy of these drugs is known to depend closely on the physico-chemistry of the lipid-water interfaces involved and on the unconventional behavior of the lipases which are their target enzymes. The lipolysis reaction which occurs at an oil-water interface involves complex equilibria between adsorption-desorption processes, conformational changes and catalytic mechanisms. In this context, surfactants can induce significant changes in the partitioning of the enzyme and the inhibitor between the water phase and lipid-water interfaces. Surfactants can be found at the oil-water interface where they compete with lipases for adsorption, but also in solution in the form of micellar aggregates and monomers that may interact with hydrophobic parts of lipases in solution. These various interactions, combined with the emulsification and dispersion of insoluble substrates and inhibitors, can either promote or decrease the activity and the inhibition of lipases. Here, we review some examples of the various effects of surfactants on lipase structure, activity and inhibition, which show how complex the various equilibria involved in the lipolysis reaction tend to be.
145 citations
"Surfactant assisted production of r..." refers background in this paper
...The interaction between surfactant and lipase were found to be primarily electrostatic.([13]) Unlike ionic surfactants, nonionic surfactants did not denature three dimensional structure of lipase by strong electrostatic interaction; rather these surfactants stabilized lipase structure by hydrophobic interactions....
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TL;DR: The main effect of the detergent is to shift the conformational equilibrium of lipases toward the open form, and the presence of detergents also permitted to improve the enantioselectivity exhibited by the immobilized lipases in some cases.
Abstract: The addition of a very small concentration of a detergent (in many instances under the critical micellar concentration (cmc)) has been found to greatly increase the activity of immobilized lipases, using those from Pseudomonas fluorescens (PFL) and Candida antarctica (isoform B) as model enzymes. However, the detergents may also have a negative effect on enzyme activity; in fact, for all enzyme preparations and substrates the activity/detergent concentration curve reached a maximum value and started to decrease, in many instances even under the initial value. The concentration and nature of the detergent (SDS, CTAB, Triton X-100, or X-45) that permitted the maximum hyperactivation was different depending on the substrate. The best hyperactivation values promoted by the presence of detergent were over a 20-fold factor. The presence of detergents permitted the inhibition of lipases by irreversible covalent inhibitors (e.g., 4-(2-aminoethyl)benzenesulfonyl fluoride hydrochloride) (AEBSF) while the enzyme, in the absence of detergent, is not inhibited by these irreversible inhibitors. This suggested that the main effect of the detergents is to shift the conformational equilibrium of lipases toward the open form. Moreover, the presence of detergents also permitted to improve the enantioselectivity exhibited by the immobilized lipases in some cases. For example, the enantioselectivity of PFL-glyoxyl agarose increased from 40 to more than 100 in the hydrolysis of (+/-)-2-hydroxy-4-phenylbutyric acid ethyl ester by using 0.1% CTAB.
87 citations
"Surfactant assisted production of r..." refers background in this paper
...The effect of surfactant on lipase depended on type of substrate also.([12]) The interaction between surfactant and lipase were found to be primarily electrostatic....
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TL;DR: In this paper, the lipase catalyzed enzymatic hydrolysis reactions have been carried out with water in oil type emulsion where optimum utilization of enzyme can be obtained, the various parameters such as time study, reusability, non-aqueous to aqueous phase ratio, effects on interfacial area of the two phases and effect of enzyme dosing were studied in order to find out the optimum conditions for maximum castor oil hydrolyisation.
Abstract: The usual methods of castor oil hydrolysis give impure product, i.e. ricinoleic acid. An alternative technique for production is the enzymatic hydrolysis of castor oil where the product is available as a light colored and odorless product. Usually lipase catalyzed enzymatic hydrolysis has been carried out in oil in water emulsions, which require rather high quantities of enzymes limiting the industrial scale operation due to very high enzyme costs. With an aim of finding the solution to this problem, the lipase catalyzed enzymatic hydrolysis reactions have been carried out with water in oil type emulsion where optimum utilization of enzyme can be obtained. The various parameters such as time study, reusability, non-aqueous to aqueous phase ratio, effects on interfacial area of the two phases and effect of enzyme dosing were studied in order to find out the optimum conditions for maximum castor oil hydrolysis.
79 citations
"Surfactant assisted production of r..." refers background or methods in this paper
...Its derivatives are used in preparation of surfactant, soap, plasticizer, lubricant, ingredient of chocolate, foam stabilizer, thermosetting acrylics, etc.([1,2]) It occupies 90% of fatty acid profile of castor oil, its main source....
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...where, ricinoleic acid content in the fatty acid profile of castor oil was taken as 90%.([1])...
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...The conventional hydrolysis processes like base catalyzed process and high temperature splitting process have certain disadvantages like formation of ricinoleic acid estolide, an unwanted by-product([1]) and generation of characteristic odor and colour....
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