- Production and immobilization of Geotrichum candidum lipase via physical adsorption on eco-friendly support: Characterization of the catalytic properties in hydrolysis and esterification reactions
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The present study reports the production of an extracellular lipase from Geotrichum candidum by submerged fermentation using cottonseed oil as inductor agent and its immobilization on poly-hydroxybutyrate (PHB) particles via physical adsorption. The catalytic properties of the biocatalyst prepared were determined in aqueous (hydrolysis of olive oil emulsion) and organic (ethyl linoleate synthesis) media. In the enzyme production, maximum hydrolytic activity of 22.91 IU/mL at 30 °C and pH 5.2 was reached after 48 h of cultivation. A single protein band with an apparent molecular mass of 65 kDa was detected by SDS-PAGE analysis. The biocatalyst prepared by offering 75 mL of crude enzymatic extract (without cells) per gram of support exhibited maximum hydrolytic activity of 404.4 ± 2.3 IU/g at 37 °C and pH 7.0, with a recovered activity percentage of around 40% and an immobilization yield of 59%. The optimal pH and temperature for both soluble and immobilized enzyme in the hydrolysis reaction was 8.0 and around 37-40 °C. The biocatalyst was more thermally stable than the crude enzymatic extract at 35 °C in 8 h (46.2% and 23.7%, respectively) and slightly more stable at 45 °C in 40 min (47.5% and 35.2%, respectively). In the esterification reaction, around 70% ester conversion was reached after 2 h of reaction under experimental conditions previously optimized by Central Composite Rotatable Design (CCRD). The biocatalyst retained 93% of its initial esterification activity after 6 successive cycles of esterification reaction. This biocatalyst is a promising one to catalyze reactions in aqueous and organic media.
- Ramos, Elisa Z.,Júnior, Rodney H. Miotti,De Castro, Patrícia F.,Tardioli, Paulo. W.,Mendes, Adriano A.,Fernandéz-Lafuente, Roberto,Hirata, Daniela B.
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Read Online
- IONIZABLE LIPIDS FOR NUCLEIC ACID DELIVERY
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The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) Wherein R1 includes an amino group. These compounds are particularly useful in the formulation and in vivo and ex vivo delivery of nucleic acid and protein therapeutics for preparing and implementing T cell transfection, gene editing, cancer therapies, cancer prophylactics, and in the preparation of vaccines.
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Paragraph 00410
(2021/01/23)
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- Novel synthesized microporous ionic polymer applications in transesterification of Jatropha curcas seed oil with short Chain alcohol
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New suites of sulfonic acid-functionalized microporous ionic polymers (PIPs) catalysts were synthesized with polymer, alkyl bromides, and 1, 3-propane sultone via a two-step procedure. The synthesized microporous PIP catalysts were characterized using FT-IR, SEM-Mapping, XPS, N2 adsorption–desorption isotherms, solid NMR spectroscopy, and element analysis. Esterification of several fatty acids with ethanol, which was used as a model reaction in the stabilization of Jatropha curcas seed oil, was checked over functionalized PIP. We tested the catalytic performance of PIP-C8 on the synthesis of fatty acid esters via the transesterification of J. curcas seed oil with a mixture of short-chain alcohols such as ethanol, ethanol–to–diethyl carbonate (1;1 molar ratio), and ethanol–to–dimethyl carbonate (1:1 molar ratio) with 170 mg of PIP-C8 at reflux temperature with agitation. The PIP-C8 catalyst was particularly effective, having achieved yields of 85%, 94%, and 70% for J. curcas seed oil with ethanol, J. curcas seed oil with ethanol–to–DEC, and J. curcas seed oil with ethanol–to–DMC, respectively, under the optimized reaction conditions. The catalyst could be recycled more than five times without significant deactivation. Kinetic studies performed at different temperatures revealed that the conversion of oleic acid to an ethyl ester follows a first-order reaction. The best catalysts with microporous structure (average pore diameter: 1.7–1.9 nm, pore volume: 0.23–0.33 cm3 g–1) and –SO3H density (0.70–0.84 mmol/gcat) were obtained by 1, 3-propane sultone of the chemically activated. The results indicate that the site activity of functionalized microporous ionic polymer materials shows promising approach for the development of environmentally friendly technology.
- Chang, Tao,Hao, Yongjing,Jinxi, Jinxi,Kai, Kai,Panchal, Balaji,Qin, Shenjun,Sun, Yuzhuang,Zhao, Cunling,Zhao, Qiaojing,Zhu, Zheng
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- Linoleic acid, α-linolenic acid, and monolinolenins as antibacterial substances in the heat-processed soybean fermented with Rhizopus oligosporus
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Antibacterial activities against Staphylococcus aureus and Bacillus subtilis were found in an ethanol fraction of tempe, an Indonesian fermented soybean produced using Rhizopus oligosporus. The ethanol fraction contained free fatty acids, monoglycerides, and fatty acid ethyl esters. Among these substances, linoleic acid and α-linolenic acid exhibited antibacterial activities against S. aureus and B. subtilis, whereas 1-monolinolenin and 2-monolinolenin exhibited antibacterial activity against B. subtilis. The other free fatty acids, 1-monoolein, monolinoleins, ethyl linoleate, and ethyl linolenate did not exhibit bactericidal activities. These results revealed that R. oligosporus produced the long-chain polyunsaturated fatty acids and monolinolenins as antibacterial substances against the Gram-positive bacteria during the fungal growth and fermentation of heat-processed soybean.
- Kusumah, Dewi,Maeda, Isamu,Murakami, Mai,Wakui, Misaki,Xie, Xiaonan,Yukihito, Kabuyama
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p. 1285 - 1290
(2020/03/03)
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- PKC activators and combinations thereof
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The present disclosure relates to PKC activators and combinations thereof. The disclosure further relates to compositions, kits, uses, and methods thereof.
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Page/Page column 45
(2020/11/13)
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- Ethyl linoleate catalytically synthesized by using ionic liquid microemulsion and preparation method thereof
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The invention belongs to the technical field of preparation of ethyl linoleate, and discloses ethyl linoleate catalytically synthesized by using an ionic liquid microemulsion and a preparation methodthereof. The preparation process comprises the following steps: (1) adding a non-polar solvent into a conventional surfactant, carrying out uniform mixing, dropwise adding imidazole ionic liquid, andcarrying out sufficient mixing to obtain a single ionic liquid microemulsion; and (2) adding linoleic acid and ethanol into the single ionic liquid microemulsion, carrying out a heating reaction, andcarrying out rotary evaporation to obtain ethyl linoleate. According to the method, the single ionic liquid microemulsion with good high-temperature stability is used as a reaction medium, the contactarea of a catalyst and a reaction substrate is increased, and generated water is solubilized in an ionic liquid microemulsion core, so a reaction rate is increased; the used catalyst is high in activity, small in equipment corrosion and low in equipment requirement, the problems of high catalyst cost, serious equipment corrosion, low reaction yield, poor product quality, harsh reaction conditionsand the like in the prior art are solved; and the method can be popularized and applied to catalytic esterification reactions.
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Paragraph 0033-0062
(2020/07/12)
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- Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids
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The α-hydrophobic long chain-α-amino esters are prepared by α-hydroxylation of a series of fatty acid esters [derived from oleic acid (OA), linoleic acid (LA), arachidonic acid (ARA) and docosahexaenoic acid (DHA)] followed by Mitsunobu reaction and hydrazinolysis of the phthalimide. These amino esters are mixed with aldehydes and electrophilic alkenes to give very good chemical yields and diastereoselectivities of prolinate derivatives incorporating a hydrophobic long chain at the α-position. This multicomponent 1,3-dipolar cycloaddition (1,3-DC) takes place at room temperature. The synthesis of the homologue hydrophobic chain of OA is performed by its oxidation to aldehyde/racemic N-tert-butylsulfinyl imine/Neff reaction. Final 1,3-DC with benzaldehyde and N-methylmaleimide affords homologue prolinate derivative in good yield.
- Selva, Elisabet,Soto, J. Javier,Nájera, Carmen,Foubelo, Francisco,Sansano, José M.
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p. 1378 - 1386
(2019/02/05)
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- Zirconium-containing metal organic frameworks as solid acid catalysts for the esterification of free fatty acids: Synthesis of biodiesel and other compounds of interest
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Zr-containing metal organic frameworks (MOFs) formed by terephthalate (UiO-66) and 2-aminoterephthalate ligands (UiO-66-NH2) are active and stable catalysts for the acid catalyzed esterification of various saturated and unsaturated fatty acids with MeOH and EtOH, with activities comparable (in some cases superior) to other solid acid catalysts previously reported in literature. Besides the formation of the corresponding fatty acid alkyl esters as biodiesel compounds (FAMEs and FAEEs), esterification of biomass-derived fatty acids with other alcohols catalyzed by the Zr-MOFs allows preparing other compounds of interest, such as oleyl oleate or isopropyl palmitate, with good yields under mild conditions.
- Cirujano,Corma,Llabrés I Xamena
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p. 213 - 220
(2015/02/19)
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- ESTERS OF DCPLA AND METHODS OF TREATMENT USING THE SAME
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The present disclosure relates to esters of 8-[2-(2-pentyl- cyclopropylmethyl)cyclopropyl]-octanoic acid ("DCPLA"). The disclosure further relates to compositions, kits, and methods for treatment using the esters.
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Paragraph 0106
(2013/05/23)
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- Novel and highly efficient SnBr2-catalyzed esterification reactions of fatty acids: The notable anion ligand effect
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In this work, the efficiency of Lewis acid catalysts, SnX2 (X = F-, Cl-, Br-, or -OAc), was investigated on the esterification reactions of fatty acids (i.e., myristic, palmitic, stearic, oleic, linoleic, and linoleic) with different alcohols (i.e., methyl, ethyl, propyl, isopropyl, and butyl alcohol). Tin(II) bromide was the most active catalyst in all reactions studied. We investigated the effects of main reaction parameters, such as catalyst concentration, temperature, and nature of alcohol and fatty acid. The highest activity of SnBr2 catalyst was discussed in terms of its lower activation energy, higher Lewis acid strength, and higher softness of anionic ligand. Finally, the SnBr 2 catalyst can be easily recovered and reused without loss of catalytic activity. Graphical Abstract: Effect of the tin catalyst nature on the oleic acid esterification with ethyl alcohol. [Figure not available: see fulltext.]
- Ferreira, Arthur Batista,Cardoso, Abiney Lemos,Da Silva, Marcio Jose
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p. 1240 - 1246
(2014/01/06)
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- Maximizing the potency of siRNA lipid nanoparticles for hepatic gene silencing in vivo
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Special (lipid) delivery: The role of the ionizable lipid pKa in the in?vivo delivery of siRNA by lipid nanoparticles has been studied with a large number of head group modifications to the lipids. A tight correlation between the lipid pKa?value and silencing of the mouse FVII gene (FVII ED50) was found, with an optimal pKa range of 6.2-6.5 (see graph). The most potent cationic lipid from this study has ED50 levels around 0.005?mg?kg?1 in mice and less than 0.03?mg?kg?1 in non-human primates.
- Jayaraman, Muthusamy,Ansell, Steven M.,Mui, Barbara L.,Tam, Ying K.,Chen, Jianxin,Du, Xinyao,Butler, David,Eltepu, Laxman,Matsuda, Shigeo,Narayanannair, Jayaprakash K.,Rajeev, Kallanthottathil G.,Hafez, Ismail M.,Akinc, Akin,Maier, Martin A.,Tracy, Mark A.,Cullis, Pieter R.,Madden, Thomas D.,Manoharan, Muthiah,Hope, Michael J.
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supporting information; experimental part
p. 8529 - 8533
(2012/10/18)
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- Enzyme-based hybrid macroporous foams as highly efficient biocatalysts obtained through integrative chemistry
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Integrative chemistry-based rational design has been used to synthesize the first lipase [C-CRl]@Glymo-Si(HIPE) and [C-TAl]@Glymo-Si(HIPE) hybrid macrocellular biocatalysts, where immobilization of crude enzymes is optimized, while circumventing the reactants' low kinetic diffusion, by the use of silica macroporous hosts. As a direct consequence, these new hybrid biocatalysts display unprecedented cycling catalysis performance, as demonstrated by the syntheses of butyloleate ester (used as biodiesel lubricant), hydrolysis of linoleic-glycero ester derivatives (end products used for detergent and soap generations), and trans-esterification (reaction involved in the synthesis of low viscosity biodiesel). Considering that the catalytic performances are given in terms of absolute conversion percentage and not just relative enzyme activity, the enzyme@Glymo-Si(HIPE) hybrid macrocellular biocatalysts presented in this study display unprecedented high yield cycling catalysis performances, where turnover numbers (TON) and turnover frequencies (TOF) show promise for real industrial applications. This study can be considered as a milestone for enzyme-based heterogeneous catalyzes, thereby enhancing their competitiveness with the supported-catalysts commonly used in industry, in total agreement with current sustainable development issues. Also, the new macrocellular biocatalysts are well-suited for large-scale industrial production because of their above-mentioned performance characteristics, further enhanced by their monolithic character, which eases the separation of the catalysts from other reaction components.
- Brun,Babeau Garcia,Deleuze,Achard,Sanchez,Durand,Oestreicher,Backov
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experimental part
p. 4555 - 4562
(2011/12/15)
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- Novel H3PW12O40: Catalysed esterification reactions of fatty acids at room temperature for biodiesel production
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The catalytic activity of Bronsted acids on fatty acid (FA) esterification at room temperature has been investigated. Noticeably, the H 3PW12O40 heteropolyacid (HPW) showed a very high activity than other catalysts herein evaluated, i.e. p-toluene sulfonic acid and sulfuric acid. High yields in ethyl esters (ca. 90%) were reached after a 4 h reaction at 25 °C on a HPW catalysed reactions. Despite the fact that HPW catalyst was used in a homogeneous phase, it could be efficiently recovered and reused through out a simple recycling protocol, without any activity loss. The effects of alcohol and the FA nature on yield reaction were also investigated.
- De Godoi Silva, Vinicius Wilker,Laier, Leticia Oliveira,Silva, Marcio Jose Da
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experimental part
p. 207 - 211
(2010/08/03)
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- METHOD OF MAKING ALKYL ESTERS
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Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70° C. to about 120° C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.
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Page/Page column 5-6
(2008/06/13)
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- Process for producing fatty acid alkyl ester composition
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An object of the present invention is to solve a problem of separation and recovery of catalysts present in an alkali metal catalytic method currently often used, a problem of excess consumption of a catalyst by a free fatty acid in a raw material, and other problems, and to solve a problem of the presence of a large excess amount of alcohol in a conventional supercritical methanol method, and to provide a method for producing a fatty acid alkyl ester composition in a reaction system containing water and free fatty acid present. The present invention has attained the above-mentioned object by provided a method for producing a fatty acid alkyl ester composition using fats and oils containing a fatty acid glyceride and/or fatty acid, wherein alcohol and/or water is allowed to co-exist with the above-mentioned fats and oils and the reaction is conducted under conditions of a temperature of 100° C. to 370° C. and a pressure of 1 to 100 MPa.
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Page/Page column 7-8
(2008/06/13)
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- PROCESS FOR EXTRACTION AND CATALYTIC ESTERIFICATION OF FATTY ACIDS FOUND IN SEWAGE SCUM
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The innovation proposed herein describes the process of a fatty acids esterification presents in the sewage scum namely the surface phase of sewage rich in fatty matter, being that this fatty acids are extracted from the scum and esterified by acid catalysts and reagents like as methanol or ethanol.
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- Dicarbonates: Convenient 4-dimethylaminopyridine catalyzed esterification reagents
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The DMAP (4-dimethylaminopyridine) catalyzed reaction of dialkyl dicarbonates la-e and carboxylic acids 2 afforded the corresponding esters 5 in good yield.
- Takeda,Akiyama,Nakamura,Takizawa,Mizuno,Takayanagi,Harigaya
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p. 1063 - 1066
(2007/10/02)
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