Hydrolysis Of Castor Oil Research Articles

Biomanufacturing of ricinoleic acid from castor oil using immobilized lipase of Pseudomonas guariconensis as biocatalyst

The efficacy of castor oil hydrolysis to ricinoleic acid by a Pseudomonas guariconensis lipase immobilized on glutaraldehyde-activated ferromagnetic nanoparticles was investigated. The prepared nanoparticles were characterized using FTIR and DLS and used as a novel biocatalyst for the production of ricinoleic acid. The optimum reaction conditions for the hydrolysis reaction by Fe3O4-APTES-Glu-lipase were optimized through the response surface methodology (RSM) which resulted in a maximum conversion of 62.5 ± 0.76%. The optimized reaction conditions are the temperature of 40 0C, pH 9, water: oil ratio of 4:1, and biocatalyst concentration of 4% w/w of the oil used. Moreover, the immobilized biocatalyst showed high stability with minimal reduction of hydrolytic efficiency after six consecutive cycles of reuse.

One-pot green synthesis and characterization of novel furan-based oligoesters

The synthesis of bio-based poly(5-hydroxymethyl-2-furancarboxylate-co-ricinoleate) was investigated either from ricinoleic acid and 5-hydroxymethyl-2-furancarboxylic acid or directly from castor oil by green biocatalytic pathways. The reactions were carried out using commercially available native and immobilized hydrolases. The reactions were performed either in the absence of solvent or in different organic solvents or ionic liquids at various molar ratios and temperatures up to 80 °C. The lipase from Pseudomonas stutzeri showed the highest catalytic efficiency at 50 °C in t-butanol. To increase the sustainability of the process, in the next step, an original “one-pot” system consisting of two consecutive reactions catalyzed by the same enzyme was developed. Ricinoleic acid, obtained by in-situ hydrolysis of castor oil, was used together with 5-hydroxymethyl-2-furancarboxylic acid as raw material for the oligoester synthesis at 100 mbar pressure in a solventless reaction system, yielding a product with average molecular weight of about 5800 gmol-1, in optimized conditions. The insertion of 5-hydroxymethyl-2-furancarboxylic acid units into the ricinoleic acid estolide backbone was demonstrated by MALDI-TOF MS and 2D NMR analysis. The thermal properties of the resulting products were evaluated by TG and DSC.

Attempt to Develop an Effective Method for the Separation of Gamma-Decalactone from Biotransformation Medium

Gamma-decalactone (GDL) is a fragrance compound obtained in the process of β-oxidation of ricinoleic acid, which is derived from the hydrolysis of castor oil. The biotechnological method of the synthesis of this lactone has been improved for over two decades, but the vast majority of research results have been based only on determining the concentration of the lactone by chromatographic methods without separating it from the biotransformation medium. In this study, we attempted to separate GDL from the medium in which the lactone was synthesized by Yarrowia lipolytica from castor oil. The effectiveness of liquid–liquid extraction, hydrodistillation, and adsorption on the porous materials (zeolite, vermiculite and resin Amberlite XAD-4) was compared. The influence of the solvent on the efficiency of GDL extraction, the influence of the acidity of the medium on the amount of GDL in the distillate, and the level of lactone adsorption on the above-mentioned adsorbents were compared by calculating the initial adsorption rate. The adsorption isotherm was determined for the most effective adsorbent. Among the five solvents tested, the most effective was diethyl ether, used at the ratio of 1:1. The extraction was characterized by higher efficiency than hydrodistillation; the difference in GDL determinations by these two methods ranged from 12.8 to 22%. The purity of the distillates was much higher than that of the extracts at 88.0 ± 3.4% compared to 53.0 ± 1.8%. The acidification of the biotransformation medium increased the concentration of the lactone in both the reaction mixture and the distillate. GDL was most efficiently adsorbed on Amberlite XAD-4 resin, for which the lactone isotherm adsorption was linear. The amount of lactone adsorbed on Amberlite XAD-4 within 1 h was approx. 80% (2.45 g), of which 1.96 g was then desorbed with ethanol. In the context of industrial applications, adsorption of GDL on Amberlite XAD-4 seems to be the most appropriate method due to material costs, the ease of the process, and low environmental burden.

Emulsifier and antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis of oxidized fatty acid esters from hydrolyzed castor oil

This study aimed to synthesize esters from oxidized fatty acids produced by castor oil hydrolysis as emulsifiers and antimicrobial compounds. Castor oil was hydrolyzed using KOH and the fatty acids were then oxidized using KMnO4. The success of oxidation proven by determined the iodine number. Esterification was conducted with varied alcohols, namely methanol, ethanol, isopropanol, and 1-butanol using ZnCl2 as catalyst and mole ratio was 1:2. The conversion percentage of esterification was determined using titrimetric method and products were characterized using FTIR. From the hydrolysis of castor oil, 84% of fatty acids were produced. Decreasing iodine number from 43.38 mg/g to 13.11 mg/g and increasing intensity of the -OH group absorption in the FTIR spectrum showed the success of fatty acids oxidation. Emulsifier test showed all products have emulsifier ability and emulsions were stable up to 24 hours with a water-in-oil (w/o) emulsion type. The best ability as an emulsifier demonstrated by methyl ester. Antimicrobial assay against Propionibacterium acnes and Staphylococcus epidermidis showed all ester products could inhibit the growth of both bacteria. Largest inhibition zone obtained from isopropyl ester for P. acnes by 16 mm and butyl ester for S. epidermidis by 17 mm.

Surfactant assisted production of ricinoleic acid using cross-linked and entrapped porcine pancreas lipase

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 through entrapment in calcium alginate beads, concentration of calcium chloride (CaCl2) was the most significant factor. Optimum conditions for immobilization were, 1.3 M CaCl2 and 12% (w/v) sodium alginate. On cross-linking with glutaraldehyde after entrapment in calcium alginate bead, PPL led to 2.7-fold higher hydrolysis compared to only entrapped PPL. Most suitable surfactant and speed of agitation were Span 80 and 300 rpm, respectively, in enhancing ricinoleic acid production involving cross-linked and entrapped PPL. Central composite design and subsequent optimization with response surface methodology (RSM) found optimum production (recovery) as 21.2% (in 3 h and 25 °C) under the optimum set of process conditions like 9.96 mg lipase/ml, pH of 8.8, 0.014 M Span 80, 2.98% (v/v) glutaraldehyde, 1.3 M CaCl2 and 12% (w/v) sodium alginate. Each of concentration of lipase, pH, surfactant (Span 80) concentration and glutaraldehyde concentration was found to be highly significant. Interactions between any two of these four variables remained insignificant. On varying temperature keeping other variables at their optima, maximum recovery for free lipase (31.29% in 3 h) was obtained at 35 °C; whereas, for immobilized lipase, recovery was maximum (26.27% in 3 h) at 45 °C. Immobilized lipase acted much better than free lipase at higher temperatures.

Production of fatty alcohols from non-edible oils by enzymatic cascade reactions

A biocatalytic cascade transforming castor oil into (R,Z)-octadec-9-en-7-ol is presented by combining a lipase catalysed hydrolysis of castor oil into ricinoleic acid followed by a photoenzymatic decarboxylation into (R,Z)-octadec-9-en-7-ol.

Biocatalytic production of ricinoleic acid from castor oil: augmentation by ionic liquid

In present study involving castor oil hydrolysis catalyzed by porcine pancreas lipase, organic solvent, and ionic liquid were applied to augment production of ricinoleic acid. Toluene was the best organic solvent (30.18% hydrolysis in 2 h). In presence of 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]), an ionic liquid, the optimal conditions were, 0.12 g ionic liquid/g oil, 4 mg enzyme/g oil, 2 g buffer/g oil, pH of 8, and 2.5 h. Under this condition, ricinoleic acid recovery was 43.41 and 52% at 25 °C and 35 °C, respectively. Organic solvent concentration, enzyme concentration, buffer concentration and time had significant impacts on lipase catalyzed hydrolysis in the presence of organic liquid; whereas, pH and speed remained insignificant. In hydrolysis involving ionic liquid, time had most important effect on ricinoleic acid production. Interaction between enzyme and buffer concentration was most significant. Interactions of ionic liquid concentration with all other variables were also significant besides buffer concentration–time interaction.

Enhanced Ricinoleic Acid Preparation Using Lipozyme TLIM as a Novel Biocatalyst: Optimized by Response Surface Methodology

Ricinoleic acid (RA) is an important raw material for plasticizers, emulsifiers, and nanomaterials. In this work, a green and efficient method was developed for RA production. Results showed that Lipozyme TLIM can be used as a novel biocatalyst to catalyze the hydrolysis of castor oil (CO) for RA preparation. Response surface methodology (RSM) was used to evaluate and optimize the effects of reaction variables on the hydrolysis of CO. Reaction conditions were optimized as follows: 41.3 °C, enzyme load 8.9%, 39.2 h, and 40:1 molar ratio of water to oil. Under these optimized reaction variables, the maximum hydrolysis ratio of CO (96.2 ± 1.5%) was obtained. The effect of hydrolysis variables on the reaction was as follows: enzyme load > hydrolysis time > temperature. In conclusion, this is a green, simple, and efficient method for RA preparation and can provide a good alternative method for RA industrial production.

Immobilization of Candida rugosa Lipase on Glutaraldehyde‐Activated Fe3O4@Chitosan as a Magnetically Separable Catalyst for Hydrolysis of Castor Oil

In this study, the catalyzed hydrolysis of castor oil by Candida rugosa lipase (CRL) immobilized on glutaraldehyde‐activated magnetic Fe3O4@chitosan is investigated. Magnetic Fe3O4 is prepared by hydrothermal method and coated with chitosan (CS). Next, CRL is immobilized on Fe3O4@chitosan using glutaraldehyde as a cross‐linking reagent. The prepared Fe3O4@CS@CRL is confirmed by scanning electron microscopy (SEM), X‐ray powder diffraction (XRD), vibrating sample magnetometry (VSM), Fourier transform infrared (FTIR) spectroscopy, and thermogravimetric analysis (TGA). The response surface methodology (RSM) based on the Box–Behnken design is used to evaluate and optimize the hydrolysis reaction variables. The optimum reaction conditions for the hydrolysis of castor oil by the Fe3O4@CS@CRL heterogeneous catalyst are found to be a water/oil ratio of 1.60:1, pH of 7.05, reaction temperature of 34 °C, and lipase concentration of 3.27%; under these conditions, the hydrolysis conversion of castor oil reached 46.81%. Moreover, the immobilized lipase showed high stability with no appreciable loss in its activity after three consecutive cycles.Practical Applications: RSM is found to be a useful technique for optimizing hydrolysis of castor oil. The high conversion of the hydrolysis of castor oil indicates that the Fe3O4@CS@CRL have potential to be used in preparing ricinoleic acid from castor oil. Ricinoleic acid have the potential to be used in printing ink as a pigment and dye disperser, plasticizers, surfactants, lubricants, and other valuable products.Ricinoleic acid can be used in pigment and dye disperser in printing ink, sebacic acid, azelaic acid, heptaldehyde, plasticizers, surfactants, lubricants, and other valuable products. Hydrolysis of castor oil catalyzed by Candida rugosa lipase (CRL) immobilized on glutaraldehyde‐activated magnetic Fe3O4@chitosan is investigated. The response surface methodology (RSM) based on the Box–Behnken design is used to evaluate and optimize the hydrolysis reaction variables. Fe3O4@CS@CRL can be easily separated from the suspension using an external strong magnet. Fe3O4@CS@CRL have potential to be used in preparing ricinoleic acid from castor oil.

Two-step enzymatic production of environmentally friendly biolubricants using castor oil: Enzyme selection and product characterization

We performed two-step enzymatic biolubricant production: castor oil hydrolysis and esterification of castor oil free fatty acids (COFFA) rich in ricinoleic acid. The hydrolysis step utilized castor seeds as catalyst yielding 93.13±5.9% COFFA in only 1h. In the esterification step, C. rugosa lipase (CRL) decreased the acidity by over 80% after 96h, utilizing as polyols neopenthylglicol (NPG), trimethylolpropane (TMP) and pentaerytritol (PE) and showed about 70% acidity decrease without polyols, indicating the production of COFFA polymers (estolides). Nuclear magnetic resonance (NMR) confirmed estolides as the main product, reaching a polymerization degree of 6/7 without polyols, 4 in the presence of PE and ricinoleic acid dimers in the presence of NPG and TMP. Analyses of biolubricant properties showed that the best product was the estolide with a polymerization degree of 6/7: viscosity index of 162, oxidation stability of 51min and pour point of −42°C.

Enzymatic incorporation of caffeoyl into castor oil to prepare the novel castor oil-based caffeoyl structured lipids

In this work, a novel castor oil-based caffeoyl structured lipids was successfully prepared by the enzymatic transesterification using castor oil (CO) as caffeoyl acceptor. During the structured lipids preparation, two competitive reactions, the hydrolysis of CO to form hydrophilic caffeoyl glycerols (CG)+dicaffeoyl glycerols (DCG) and the transesterification of CO with ethyl caffeate (EC) to form lipophilic caffeoyl mono- and di-acylglycerols (CMAG and CDAG), were found. Reaction progress was monitored using HPLC-ESI–MS and HPLC-UV. The effects of by-product ethanol removal and reaction variables on the transesterification and reaction selectivity were evaluated. Results showed that, the activation energies for the transesterification and for the selective formations of CMAG+CDAG and CG+DCG were 57.60kJ/mol, 58.86kJ/mol, and 60.53kJ/mol, respectively. Under the optimal reaction conditions (enzyme load 23%, 90°C, 1:3 molar ratio of EC to CO, and 46.5h), EC conversion and the yield of CMAG+CDAG were 93.68±2.52% and 78.11±1.35%, respectively.

Kinetics of enzymatic hydrolysis of methyl ricinoleate

Ricinoleic acid is an unsaturated hydroxy fatty acid that naturally occurs in castor oil in proportions of up to 85–90%. Ricinoleic acid is a potential raw material and finds several applications in coatings, lubricant formulations and pharmaceutical areas. Enzymatic hydrolysis of castor oil is preferred over conventional hydrolysis for the preparation of ricinoleic acid to avoid estolide formation. A kinetics analysis of the enzymatic hydrolysis of Methyl Ricinoleate in the presence of Candida antarctica Lipase B was carried out in this study by varying reaction temperature (40–60 °C) and enzyme concentration (2–5%). The optimal conditions were found to be 6 h reaction time, temperature 60°C, buffer to methyl ricinoleate ratio 2:1(v/w) and 4% enzyme concentration to achieve a maximum conversion of 98.5%. A first order reversible reaction kinetic model was proposed to describe this reaction and a good agreement was observed between the experimental data and the model values. The effect of temperature on the forward reaction rate constant was determined by fitting data to the Arrhenius equation. The activation energy for forward reaction was found to be 14.69 KJ·mol−1.

Vanillin-derived non-ionic surfactants as green corrosion inhibitors for carbon steel in acidic environments

Four eco-friendly ('green') non-ionic surface active agents were synthesized via reaction of fatty acids obtained from hydrolysis of castor oil with vanillin. The products were then reacted with monoethanol amine to form a vanillin ester Schiff base. The vanillin ester Schiff base was ethoxylated using ethylene oxide gas in the presence of tri-ethyl amine as a catalyst to give the desired non-ionic surfactants. The chemical structures of the obtained surfactants were characterized using FTIR and 1HNMR spectroscopy. The inhibition effect of the four synthesized non-ionic surfactants derived from vanillin (VE15, VE20, VE40, and VE60) on the corrosion of carbon steel in acidic media of 0.5-M HCl was studied by weight loss, potentiodynamic and electrochemical impedance spectroscopy measurements. The results show that the synthesized inhibitors are effective inhibitors even at very low concentrations, and the adsorption on carbon steel surface obeys the Langmuir adsorption isotherm. Potentiodynamic polarization curves reveal that the synthesized inhibitors behave as mixed-type inhibitors. Adsorption of used inhibitors led to a reduction in the double layer capacitance and an increase in the charge transfer resistance. Calculated ΔG ads o values indicated that the mechanism by which these inhibitors adsorb onto carbon steel in 0.5-M HCl solution is chemical adsorption. The surface activities of the synthesized surfactants were determined using surface tension measurements. The biodegradability of these surfactants indicates that the compounds readily degrade in the environment and can be considered as green corrosion inhibitors.

Effect of POX genotype and Lip2p overexpression on lactone production and reconsumption by Yarrowia lipolytica using castor oil as substrate

γ-Decalactone production from ricinoleic acid biotransformation by Yarrowia lipolytica has drawn the attention of many authors and, in the last years, molecular and physiological developments were made through the use of engineered strains in novel culture conditions.The purpose of this work was to monitor the performance of modified Y. lipolytica strains in their lipid metabolism specifically at the β-oxidation pathway (MTLY40-2P strain, disrupted in the native genes POX2-5 and expressing an ectopic Aox2p-encoding gene) or at the triglyceride hydrolysis (JMY3010 strain, Lip2p overexpressed) using castor oil as substrate, in a lab-scale bioreactor. Using step-wise fed-batch cultures of MTLY40-2P strain, a γ-decalactone concentration of 7gL−1 was reached. γ-Decalactone reconsumption was prevented and hydroxylactone production was reduced by Y. lipolytica MTLY40-2P strain. Moreover, substantial increase in the initial rate of aroma production was obtained with strain overexpressing LIP2 gene due to the fast hydrolysis of castor oil.

Monitoring the Rhizopus oryzae lipase catalyzed hydrolysis of castor oil by ATR-FTIR spectroscopy

A rapid and environmental friendly Attenuated total reflectance Fourier-transform infrared (ATR-FTIR) spectroscopic method was developed for monitoring the Rhizopus oryzae lipase (ROL) catalyzed hydrolysis of castor oil in oil-in-water emulsion system. A calibration curve was constructed using partial least square (PLS) model by gravimetric addition of oleic acid (10–50%) in castor oil to detect the carbonyl absorption of free fatty acids (FFA) in the region (1690–1730cm−1). The correlation co-efficient (R2) and root mean square error of calibration (RMSEC) by PLS model were found to be 0.999 and 0.316, respectively. ROL was found to be an efficient biocatalyst to produce free fatty acids (FFA) from castor oil. Factors affecting the rate of hydrolysis such as enzyme concentration (0.01%, w/v), pH (7), temperature (37°C), oil–water ratio (1:4) and reaction time (12h) were optimized. Under all set of conditions the ROL effectively hydrolyzed castor oil up to 90% yield of fatty acids. The methodology is fairly environmental friendly in both cases, i.e. using lipase for hydrolysis of castor oil and analyzing the product through FTIR spectroscopy.

Recycling of waste poly(ethylene terephthalate) with castor oil using microwave heating

The chemical recycling of waste poly(ethylene terephthalate) (PET) using castor oil (CO) as a reagent is reported. CO presents a renewable alternative to petrochemical based reagents, e.g. glycols, and enables also substantial modification of final physico-chemical properties of a received product. Advantageously, microwave irradiation was used to accelerate the depolymerization of PET. A composition of obtained product was strongly influenced by the reaction temperature. When the decomposition of PET was performed at temperature higher than 240 °C, then a significant extent of side products based on PET oligomers and transesterified CO was observed due to dehydration and hydrolysis of CO. Contrary to that, PET decomposition took place at slow rate below 230 °C and the optimal reaction temperature lies in the relatively narrow interval from 230 °C to 240 °C. The product prepared in the optimal temperature range did not contain any high molecular weight PET oligomers. MALDI-TOF mass spectrometry enabled to identify the structures included in the obtained polyol product. The maximum number of six repeating monomeric unit of PET was found in the product, which confirmed practically the complete depolymerization of PET chain and good reactivity of the acylester hydroxyl groups of CO.

Features of the enzymatic hydrolysis of castor oil

Ricinoleic acid, which is used in medicine and veterinary science and is the initial material in the organic synthesis of various valuable products, is obtained via the hydrolysis of castor oil. The enzymatic hydrolysis of castor oil, which allows us to conduct the process under mild conditions (in the temperature range of 35–45°C and without high pressures) is a promising method for obtaining ricinoleic acid. This work demonstrates the feasibility of the enzymatic hydrolysis of castor oil with lipase from Candida rugosa in oil-water systems without an emulsifier. We propose a method for hydrolysis without emulsifiers, simplifying the process of isolating the target product (a mixture of free fatty acids in which ricinoleic acid predominates) and thus the relevant technology. The catalyst that we use ensures the environmental friendliness of the process. Our selection of the experimental conditions for hydrolysis resulted in a 47% yield of fatty acids.

Erratum to: Impact of Lipase-Mediated Hydrolysis of Castor Oil on γ-Decalactone Production by Yarrowia lipolytica

Erratum to: Impact of Lipase-Mediated Hydrolysis of Castor Oil on γ-Decalactone Production by Yarrowia lipolytica

Impact of Lipase‐Mediated Hydrolysis of Castor Oil on γ‐Decalactone Production by Yarrowia lipolytica

Abstractγ‐Decalactone is an industrially interesting peach‐like aroma compound that can be produced biotechnologically through the biotransformation of ricinoleic acid. Castor oil (CO) is the raw material most used as the ricinoleic acid source. The effect of different CO concentrations on the γ‐decalactone production by Yarrowia lipolytica was investigated in batch processing, and 30 g L−1 was found to be the optimal oil concentration. Under these conditions, cells were able to produce lipase but at low activity levels, which might limit ricinoleic acid release and consequently, the γ‐decalactone production rate. Thus, the enzymatic hydrolysis of CO by commercial lipases was studied under different operating conditions. Lipozyme TL IM was found to be the most efficient and the optimal hydrolysis conditions were pH 8 and 27 °C. The use of hydrolyzed CO in the aroma production allowed a decrease in the lag phase for γ‐decalactone secretion.

Lipase Induction in Yarrowia lipolytica for Castor Oil Hydrolysis and Its Effect on γ‐Decalactone Production

Abstractγ‐Decalactone is an aromatic compound of industrial interest, resulting from the biotransformation of ricinoleic acid, the major constituent of castor oil. In order to increase the availability of the substrate to the cells for the aroma production, castor oil previously hydrolyzed can be used. This hydrolysis may be promoted by enzymatic action, more specifically by lipases. In this work, the influence upon the aroma production of the lipase produced by Yarrowia lipolytica, a microorganism able to carry out the biotransformation, was studied. In a first approach, lipase induction conditions were analyzed using different Y. lipolytica strains and culture conditions, such as the inoculation mode of the lipase production medium. Lipase production was not affected by the cells centrifugation, so this step was eliminated, reducing the time and phases of the process. Moreover, Y. lipolytica W29 was shown to be the most adequate strain for lipase production. To investigate the importance of castor oil hydrolysis, the pre‐addition of an inducer of lipase production (olive oil) to the biotransformation medium was tested. Results showed that the highest aroma production (1,600 mg L−1) was obtained without a lipase inducer. However, the pre‐induction of lipase decreased the lag phase for γ‐decalactone secretion.