Browsing by Subject "Lipase"
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- PublicationOpen AccessA review of guerbet alcohols and their esters: synthesis, applications, and future perspectives(MDPI, 2025-11-14) Montiel Morte, María Claudia; Ortega Requena, Salvadora; Gómez Gómez, María; Murcia Almagro, María Dolores; Máximo, María Fuensanta; Bastida Rodríguez, Josefa; Ingeniería Química; Facultad de QuímicaGuerbet alcohol esters are compounds with specific properties that make them particularly suitable for use as cosmetic ingredients, plasticizers, or biolubricants. Guerbet alcohols are used for their synthesis. These are primary alcohols with beta branching and a lower melting point than their linear counterparts. Due to the branching, the products are liquid at lower temperatures, have good volatility, and exhibit better color and oxidation stability. This paper presents a systematic literature review on the synthesis and applications of Guerbet alcohol esters. Finally, emphasis is placed on the future of these synthesis processes, which could be based on the use of biocatalysts, thus promoting the application of new environmentally friendly procedures.
- PublicationOpen AccessBiocatalytic hydrolysis of di-urethane model compounds in ionic liquid reaction media(Elsevier, 2024-03-15) Salas, Rebeca; Villa Aroca, Rocío; Cano, Sergio; Garcia Verdugo, Eduardo; Villa Aroca, Rocío; Lozano Rodríguez, Pedro; Nieto Cerón, Susana; Bioquímica y Biología Molecular B e InmunologíaThe suitability of different enzymes to carry out the hydrolysis of two-different toluene-based urethane model compounds (i.e. bis(2-methoxyethyl) (4-methyl-1,3-phenylene)dicarbamate, and bis(2-methoxyethyl) (2-methyl-1,3-phenylene)dicarbamate) has been demonstrated for the first time by taking advantage of ionic liquid (IL) technologies. Toluene-based urethane compounds were prepared from usual substrates in polyurethane industrial synthesis. Afterwards, their carbamate groups were target of a biocatalytic hydrolysis by means of different commercial hydrolases (i.e. lipase, urease and proteases) in either water, hydrophilic organic solvents (i.e. ethylene glycol or 1,2-dimethyl-1,3-dioxolane-4-methanol, (solketal)), or hydrophobic ILs (e.g. [C4mim][NTf2], etc.) as reaction media. Because of the insolubility of these compounds in water, most of the enzymes were unable to catalyse the hydrolysis of the di-urethane substrates in pure water, being clearly improved (up to 31.6 mU/mg for the urease case) in solketal:water (90:10, v/v) reaction media. When hydrophobic ILs were added into this reaction medium, the urease activity increased by more than twice (74.1 mU/mg). The most promising results for the hydrolysis of these urethane compounds were obtained by combining lipase and urease biocatalysts in a IL:solketal:H2O (70:25:5, v/v/v) reaction medium. These results demonstrate a possible biocatalytic approach for the hydrolytic depolymerization of polyurethane foam wastes.
- PublicationOpen AccessDeveloping the rate equations for two enzymatic Ping-Pong reactions in series: Application to the bio-synthesis of Bis(2-ethylhexyl) azelate(Elsevier, 2020-09-15) Gómez, M.; Murcia, M.D.; Serrano-Arnaldos, M.; Gómez, E.; Gómez, J.L.; Hidalgo, A.M.; Máximo, M.F.; Ingeniería QuímicaIn this work, the rate equations of two simultaneous bisubstrate Ping-Pong in series reactions have been developed for the first time. To obtain these equations, the approximation to the stationary state has been applied and, for the total balance of enzyme, all the intermediate complexes of the two reactions, which are present simultaneously in the reaction medium, have been taken into account. To check the kinetic equations obtained, the synthesis of bis(2-ethylhexyl) azelate by transesterification from diethyl azelate and 2-ethylhexanol, in the presence of the immobilized lipase Novozym@ 435, has been used as reaction model. The reaction has been carried out in solvent-free conditions in a batch reactor. A design model of the reactor has also been developed and solved by applying a numerical method. The model equations have been implemented in user’s software in Visual Basic for Applications. In that software a routine, based on a very well-known procedure to minimize the sum of the square errors, has also been implemented. By using this software, the model parameters have been determined by fitting the experimental data to the model. A high determination coefficient was obtained, which validated both the kinetic equations and the reactor’s design model.
- PublicationOpen AccessENZYMATIC BIOSYNTHESIS OF RICINOLEIC ACID ESTOLIDES(Elsevier, 2005-05-31) Bódalo-Santoyo, A.; Bastida Rodríguez, Josefa; Máximo Martín, María Fuensanta; Montiel Morte, María Claudia; Murcia Almagro, María Dolores; Ingeniería QuímicaCandida 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 144000 ppm and a lipase concentration of 13.33 mgE/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 hours.
- PublicationOpen AccessGuerbet alcohols, ideal substrates for the sustainable production of branched esters(MDPI, 2025-11-11) Montiel Morte, María Claudia; Máximo, María Fuensanta; Gómez Gómez, María; Murcia Almagro, María Dolores; Ortega Requena, Salvadora; Bastida Rodríguez, Josefa; Ingeniería Química; Facultad de QuímicaSaturated and branched high molecular weight organic esters are highly valued as emollients in the cosmetic industry due to their superior properties. Their saturated character provides resistance to oxidation and rancidity. Additionally, their branched structure endows them with low melting temperatures, enabling them to remain liquid over a broad temperature range. These esters can be obtained from branched alcohols, branched fatty acids or both, using chemical or enzymatic processes. Among branched alcohols, Guerbet alcohols stand out. Due to their characteristic properties as branched, saturated alcohols with superior oxidative stability and extremely low volatility, they are proposed as excellent substrates for the enzymatic synthesis of these compounds. This study represents the first investigation into the biocatalytic synthesis of three specific esters: those formed between 2-octyl-1-dodecanol (C20 Guerbet alcohol) and the fatty acids myristic (MA), palmitic (PA), and stearic acid (SA). To achieve this, an environmentally sustainable biocatalytic process was developed. The synthesis involves a solvent-free esterification catalyzed by the commercial immobilized lipase, Lipozyme® 435, conducted within a vertically stirred, thermostated batch tank reactor. Optimal conditions for lipase concentration and temperature were established, and the sustainability of the process was successfully quantified using various “green metrics”.
- PublicationRestrictedOptimized enzymatic synthesis of the food additive polyglycerol polyricinoleate (PGPR) using Novozym® 435 in a solvent free system(Elsevier, 2014-01-21) Ortega Requena, Salvadora; Bódalo-Santoyo, A.; Bastida Rodríguez, Josefa; Máximo, María Fuensanta; Montiel Morte, María Claudia; Gómez Gómez, María; Ingeniería Química; Facultad de QuímicaPolyglycerol polyricinoleate (PGPR) is used as an emulsifier in the food industry, especially in chocolate coatings and chocolate bars. PGPR improves the characteristics of molten chocolate by reducing yield stress, facilitating the coating of confectionery pieces, while limiting the amount of cocoa butter involved. The enzymatic synthesis of PGPR catalyzed by lipases presents several advantages over chemical synthesis, including enzyme specificity and the mild conditions needed, thereby avoiding undesirable side-reactions and by-products. A novel process to synthesize PGPR using a biocatalyst, Novozym® 435, is presented. Novozym® 435 is appropriate for catalyzing both the reactions involved in this process. A PGPR fulfilling European specifications for this food additive as well as recommendations set out in the Food Chemical Codex, was obtained using a discontinuous vacuum reactor with a dry nitrogen flow. In addition, the biocatalyst reuse would decrease costs. Moreover, it was confirmed that the ability to obtain PGPR in a one-step reaction significantly shortens the time required.
- PublicationOpen AccessSCREENING AND SELECTION OF LIPASES FOR THE ENZYMATIC PRODUCTION OF POLYGLYCEROL POLYRICINOLEATE(2009-05-07) Bódalo, A.; Bastida Rodríguez, Josefa; Máximo Martín, María Fuensanta; Montiel Morte, María Claudia; Gómez, M.; Ortega Requena, Salvadora; Ingeniería QuímicaWe have demonstrated, for the first time, that polyglylcerol polyricinoleate (PGPR) can be synthesised using lipases as biocatalyst with very good results. Of the twenty one lipases screened for their ability to catalyse PGPR production from a mixture of polyricinoleic acid and polyglycerol-3, only twelve lipases were able to catalyse the reaction. All of them were from microbial sources (bacteria and fungi) and were 1, 3-specific or "random" lipases. The selection procedure was based not only on the enzymatic activity but also on economic criteria. Lipases from Mucor javanicus, Rhizopus arrhizus and Rhizopus oryzae were finally chosen, and all three enzymes were successfully immobilized by adsorption onto an anion exchange resin where they showed their suitability to catalyse the synthesis of PGPR. This represents a promising starting point for developing an industrial process for the green production of polyglycerol polyricinoleate.
- PublicationOpen AccessSolvent-free polyglycerol polyricinoleate synthesis mediated by lipase from Rhizopus arrhizus(2011-02-04) Gómez, J.L.; Bastida Rodríguez, Josefa; Máximo Martín, María Fuensanta; Montiel Morte, María Claudia; Murcia Almagro, María Dolores; Ortega Requena, Salvadora; Ingeniería Química
- PublicationOpen AccessSustainable Biocatalytic Synthesis of a Second-Generation Biolubricant(2024-02-15) Montiel, M.C.; Gómez, M.; Murcia, M.D.; Ortega Requena, Salvadora; Máximo, F.; Bastida, J.; Ingeniería QuímicaBackground: Biolubricants represent a category of lubricating substances derived from sustainable sources such as vegetable oils, animal fats, and other bio-based materials. They are considered more environmentally friendly than mineral-based lubricants because they are biodegradable and nontoxic. Biolubricants derived from vegetable oils or animal fats were used as first-generation biolubricants. They have limited performance at extreme temperatures, both high and low, as well as low oxidative stability. Substitution of the double bonds by branching improves the performance and stability of the resulting second-generation biolubricants. Methods: In the past, the production of these compounds has relied on the chemical pathway. This method involves elevated temperatures and inorganic catalysts, leading to the necessity of additional purification steps, which decreases environmental sustainability and energy efficiency. A more environmentally friendly alternative, the enzymatic route, has been introduced, in accordance with the principles of “Green Chemistry”. Results: In this paper, the esterification of 2-methylhexanoic acid with 2-octyl-1-dodecanol and its optimization were developed for the first time. The synthesis was conducted within a jacketed batch reactor connected to a thermostatic bath in a solvent-free reaction medium and using Lipozyme® 435 as biocatalyst. Conclusions: The high viscosity index value of this new hyperbranched ester (>200, ASTM D2270) suggests that it may be an excellent biolubricant to be used under extreme temperature conditions. Regarding sustainability, the main green metrics calculated point to an environmentally friendly process.
- PublicationOpen AccessSustainable synthesis of branched-chain diesters(Elsevier, 2020-11-11) Serrano-Arnaldos, M.; Ortega Requena, Salvadora; Sánchez, J.A.; Hernández, A.; Montiel, M.C.; Máximo, F.; Bastida, J.; Ingeniería QuímicaEsters from branched alcohols and dicarboxylic linear acids are widely used as lube bases due to their good performance at low temperatures. This work proposes a new process to synthesize bis(2-ethylbutyl) adipate and bis(2-ethylbutyl) sebacate by using the lipase-based catalyst Novozym® 435 in a solvent-free system. Different reaction strategies have been tested in order to minimize 2-ethyl-1-butanol losses due to its evaporation and optimum operation conditions have been determined: 2.5 % of biocatalyst, 50 °C and a molar excess of alcohol of 15 % for the adipic diester and of 25 % for the sebacic one. It has also been proven that the immobilized enzyme can be reused in seven successive reaction cycles, achieving high yields without an appreciable reduction of activity. This biocatalytic pathway is a promising basis for the development of a more sustainable large scale process for obtaining biodegradable lubricants, as it is pointed out by productivity, economic and green metrics calculations.
- PublicationOpen AccessUnderstanding the enzymatic synthesis of a new biolubricant: decane-1,10-diyl bis(2-methylpentanoate)(MDPI, 2024-12-26) Ortega Requena, Salvadora; Máximo, María Fuensanta; Montiel Morte, María Claudia; Gómez Gómez, María; Murcia Almagro, María Dolores; Bastida Rodríguez, Josefa; Ingeniería Química; Facultades de la UMU::Facultad de QuímicaThe value of branched esters comes from the special properties they have in cold environments, which allow them to remain liquid over a wide range of temperatures. These properties make them useful for application in the cosmetic industry or as lubricant additives. This paper presents the studies carried out to ascertain the operational feasibility of the enzymatic esterification of 2-methylpentanoic acid (MPA) with 1,10-decanediol (DD), with the objective of obtaining a novel molecule: decane-1,10-diyl bis(2-methylpentanoate) (DDBMP). The enzymatic reaction is conducted in a thermostated batch reactor, utilizing the commercially available immobilized lipase Lipozyme® 435 in a solvent-free medium. The reaction conversion is determined by an acid number determination and a gas chromatographic analysis. The most optimal result is achieved at a temperature of 80 °C, a biocatalyst concentration of 2.5% (w/w), and a non-stoichiometric substrate relation. A preliminary economic study and the calculation of Green Metrics has established that the operation with a 30% molar excess of acid is the best option to obtain a product with 92.6% purity at a lower cost than the other options and in accordance with the 12 Principles of Green Chemistry. The synthetized diester has a viscosity index of 210, indicating that this new molecule can be used as a biolubricant at extreme temperatures.