- METHOD FOR PREPARING MONOGLYCERIDES
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The present application relates to a method for preparing monoglycerides, a method for recovering glycerin and catalysts after the process for preparing monoglycerides, and a process for preparing cyclic monoglycerides.(AA) Fatty acid glycerin catalyst(BB) Esterification(CC) Reuse(DD) Settling and separation(EE) Glycerin and most of catalyst(F1,F2) Glyceride layer(GG) Glycerin(HH) Washing and separation(II) Glycerin and traces of catalyst(JJ) Glyceride layer(KK) Molecular distillation(LL) Glycerin and unreacted fatty acid(MM) Di- and tri-glycerideCOPYRIGHT KIPO 2020
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Paragraph 0079-0081; 0084; 0085
(2020/08/18)
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- Development of a lipase-mediated epoxidation process for monoterpenes in choline chloride-based deep eutectic solvents
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Chemical syntheses in contemporary process industries today are predominantly conducted using organic solvents, which are potentially hazardous to humans and the environment alike. Green chemistry was developed as a means to overcome this hazard and it also holds enormous potential for designing clean, safe and sustainable processes. The present work incorporates the concepts of green chemistry in its design of a lipase-mediated epoxidation process for monoterpenes; the process uses alternative reaction media, namely deep eutectic solvents (DESs), which have not been reported for such an application before. Choline chloride (ChCl), in combination with a variety of hydrogen bond donors (HBD) at certain molar ratios, was screened and tested for this purpose. The process was optimized through the design of experiments (DoE) using the Taguchi method for four controllable parameters (temperature, enzyme amount, peroxide amount and type of substrate) and one uncontrollable parameter (DES reaction media) in a crossed-array design. Two distinct DESs, namely glycerol:choline chloride (GlCh) and sorbitol:choline chloride (SoCh), were found to be the best systems and they resulted in a complete conversion of the substrates within 8 h. Impurities (esters) were found to form in both the DESs, which was a concern; as such, we developed a novel minimal DES system that incorporated a co-substrate into the DES so that this issue could be overcome. The minimal DES consisted of urea·H2O2 (U·H2O2) and ChCl and exhibited better results than both the GlCh and SoCh systems; complete conversions were achieved within 2 h for 3-carene and within 3 h for both limonene and α-pinene. Product isolation with a simple water/ethyl acetate based procedure gave isolated yields of 87.2 ± 2.4%, 77.0 ± 5.0% and 84.6 ± 3.7% for 3-carene, limonene and α-pinene respectively.
- Ranganathan, Sumanth,Zeitlhofer, Sandra,Sieber, Volker
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supporting information
p. 2576 - 2586
(2017/07/24)
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- For producing fatty acid triglyceride method and of esterification reaction of esterification reaction device
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The invention relates to an esterification reaction method and device for production of fatty acid triglyceride. The esterification reaction method and device for production of fatty acid triglyceride have the characteristics of high reaction efficiency and short reaction time and can be used for producing high-content fatty acid triglyceride. The esterification reaction method comprises the following steps: (1) carrying out esterification reaction on a catalyst and glycerin; (2) controlling the reaction pressure and the reaction temperature in an esterification reactor; and (3) discharging the product of reaction through a discharge port. The esterification reaction device for production of fatty acid triglyceride comprises an esterification reactor and further comprises a pre-mixing tank and a fatty acid pre-heater, wherein the pre-mixing tank is communicated with a catalyst feed port and a glycerin feed port, the outlet of the pre-mixing tank is communicated with an atomizer, the bottom of the inner cavity of the esterification reactor is provided with a bubbling air sifter, the fatty acid pre-heater is communicated with a fatty acid feed port, the top of the esterification reactor is communicated with a fatty acid cooler and a vacuum device interface, and the bottom of the esterification reactor is provided with a discharge port.
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Paragraph 0032-0033
(2017/03/21)
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- Biobased catalyst in biorefinery processes: Sulphonated hydrothermal carbon for glycerol esterification
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Sulphonated hydrothermal carbon (SHTC), obtained from d-glucose by mild hydrothermal carbonisation and subsequent sulphonation with sulphuric acid, is able to catalyse the esterification of glycerol with different carboxylic acids, namely, acetic, butyric and caprylic acids. Product selectivity can be tuned by simply controlling the reaction conditions. On the one hand, SHTC provides one of the best selectivity towards monoacetins described up to now without the need for an excess of glycerol. On the other hand, excellent selectivity towards triacylglycerides (TAG) can be obtained, beyond those described with other solid catalysts, including well-known sulphonic resins. Recovery of the catalyst showed partial deactivation of the solid. The formation of sulphonate esters on the surface, confirmed by solid state NMR, was the cause of this behaviour. Acid treatment of the used catalyst, with subsequent hydrolysis of the surface sulphonate esters, allows SHTC to recover its activity. The higher selectivity towards mono- and triesters and its renewable origin makes SHTC an attractive catalyst in biorefinery processes.
- De La Calle, Carlos,Fraile, José M.,García-Bordejé, Enrique,Pires, Elísabet,Roldán, Laura
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p. 2897 - 2903
(2015/05/13)
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- Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation
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Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters.
- Ferreira, Rui,Garcia, Helga,Sousa, Andreia F.,Guerreiro, Marina,Duarte, Filipe J. S.,Freire, Carmen S. R.,Calhorda, Maria Jose,Silvestre, Armando J. D.,Kunz, Werner,Rebelo, Luis Paulo N.,Silva Pereira, Cristina
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p. 2993 - 3002
(2014/01/06)
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- METHOD FOR THE PREPARATION OF TRIGLYCERIDES OF MEDIUM-CHAIN LENGTH FATTY ACIDS
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A method is disclosed for the preparation of glycerol esters (triglycerides) of medium-chain length monocarboxylic fatty acids which consists of the reaction of the precursor free fatty acid and glycerol in the presence of a catalyst under partial vacuum. The process preferably uses a metal catalyst such as an oxide or a chloride of tungsten, molybdenum, calcium, zinc, chromium or magnesium. The method of the invention allows the preparation in high yield and high purity (>99.5%) of the final triglyceride. The present method allows the formation of triglycerides without solvent. Are also contemplated, the triglyceride obtained by the method, and the pharmaceutical composition containing the triglyceride as an excipient or as an active ingredient.
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Paragraph 0040; 0042
(2013/09/12)
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- MALLEABLE, BIODEGRADABLE HEMOSTATIC AGENT
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A malleable, biodegradable hemostatic agent is provided that can be used for mechanical sealing of bleeding bone tissue, as well as a method for forming a malleable, biodegradable hemostatic agent of this type, and a medical implant having a coating that includes a malleable, biodegradable hemostatic agent of this type. The malleable, biodegradable hemostatic agent contains (a) at least one saturated glycerol-1,2,3-tri-fatty acid ester having a melting temperature above 37° C., (b) at least one filling agent present in particulate form, at least in part, and having a melting temperature above 37° C., and (c) at least one compound having a melting temperature not above 37° C. and a solubility at a temperature of 25° C. of less than 50 grams per liter of water.
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- Method for carrying out reactions characterized by an equilibrium
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The invention relates to a process for conducting a chemical reaction characterized by an equilibrium in a reaction system designed as a loop reactor, said loop reactor comprising a reactor vessel (1), at least one loop connected to said reactor vessel (1) each by means of an outlet and an inlet, said loop comprising means (3) for pumping over a fluid reaction material, at least one he exchanger (4), optionally means (5) for feeding said reaction material into Me reactor vessel (1) and a separate gas loop (8) which is connected to the gas space of the reactor vessel (1) above the reaction mixture and has separate means for feeding a gas into the gas loop (8), for withdrawing gas from the gas loop (8) and/or for treating said gas circulating in the gas loop (8), said process comprising the steps of circulating and/or treating said gas in said gas loop (8), feeding said gas into the reactor vessel (1) for influencing the equilibrium of a reaction conducted in said reactor vessel (1) and being characterized by the equilibrium and, after influencing said equilibrium reaction conducted in said reactor vessel (1), exhausting said gas from said reactor vessel (1) into the gas loop (8).
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Page column 12
(2008/06/13)
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- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
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1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
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p. 839 - 843
(2007/10/03)
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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- Topical corticosteroid formulations
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This present invention relates to a solution for topical or local application comprising at least one corticosteroid; from about 1% to 4% by weight of solubilization agents consisting essentially of a combination of at least one glyceryl ester of a fatty acid of 6 to 22 carbon atoms and a betaine surfactant, from about 10% to 50% by weight of composition of an alkanol cosolvent, and from about 20% to 50% water.
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