- RETRACTED ARTICLE: Silica supported microporous melamine tri sulfonic acid catalyst towards biodiesel fuel production from waste cooking oil and utilization of side stream
-
A novel silica based melamine tri sulfonic acid catalyst was successfully prepared by chlorosulfonation of melamine at ambient conditions and applied to the transesterification of waste cooking oil for the production of biodiesel. Glycerol obtained as a side stream at the end of the transesterification reaction along with biodiesel molecules. However, world is facing the problems of disposal of glycerol obtained from biodiesel synthesis as a byproduct and simultaneously they are facing the problem of the abundance of feedstocks for biodiesel synthesis. Therefore, obtained crude glycerol was also successfully converted into triglyceride via esterification of lauric acid over same catalyst. Biodiesel yields were calculated using gas chromatography. Highest biodiesel (%) yield was observed up to 98.00%. Synthesized SMTSA revealed optimistic catalytic activity for transesterification of waste cooking oil with 5% catalyst dose (w/w). SMTSA catalyst was duly characterized by FT-IR, XRD, BET, TPD-NH3 and SEM analysis. While, synthesized biodiesel and triglycerides of lauric acid were well characterized by FT-IR as well as 1H and 13C NMR spectroscopic techniques.
- Savaliya, Mehulkumar L.,Dholakiya, Bharatkumar Z.
-
-
Read Online
- Cellulose sulfuric acid catalyzed esterification of biodiesel derived raw glycerol to medium chain triglyceride: The dual advantage
-
Biodiesel derived raw glycerol represent a copious and inexpensive source which can be used as raw material for a variety of value added products such as 1,3-propanediol, poly hydroxyalkanoate, hydrogen, epichlorohydrin and also lactic acid. So, this work was investigated to study chemical conversion of biodiesel derived raw glycerol and lauric acid to triglycerides of lauric acid via esterification reaction over cellulose sulfuric acid as an efficient, biodegradable and recyclable solid acid catalyst. Synthesized catalyst was characterized by fourier transform infra-red spectroscopy (FT-IR) as well as BET surface area analysis. While, synthesized triglyceride of lauric acid was fittingly characterized by FT-IR as well as 1H and 13C Nuclear magnetic resonance spectroscopic techniques. Graphical Abstract: [Figure not available: see fulltext.]
- Savaliya, Mehulkumar L.,Dholakiya, Bharatkumar Z.
-
-
Read Online
- Lipase-catalyzed two-step esterification for solvent-free production of mixed lauric acid esters with antibacterial and antioxidative activities
-
Mixed lauric acid esters (MLE) with antibacterial and antioxidative activities were produced through lipase-catalyzed two-step esterification in solvent-free system without purification. In the first reaction, erythorbyl laurate was synthesized for 72 h. Successive reaction for 6 h at molar ratio of 1.0 (lauric acid to glycerol) produced MLE containing erythorbyl laurate and glyceryl laurate with small amounts of residual substrates, by converting 99.52% of lauric acid. MLE addition (0.5–2.0%, w/w) to Tween 20-stabilized emulsions decreased droplet size, polydispersity index, and zeta-potential, possibly enhancing the emulsion stability. In the emulsions, MLE at 0.5 and 2.0% (w/w) caused 4.4–4.6 and 5.9–6.1 log reductions of Gram-positive (Staphylococcus aureus, Listeria monocytogenes) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), respectively, within 12 h. Lipid hydroperoxide concentrations decreased to 50.8–98.3% in the presence of 0.5–2.0% (w/w) MLE. These findings support a novel approach without needing purification to produce multi-functional food additives for emulsion foods.
- Yu, Hyunjong,Byun, Yerim,Chang, Pahn-Shick
-
-
- Sustainable production of biodiesel and transformation of glycerol to glycerol laurate esters over inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes
-
Solid acid-catalyzed biodiesel production from inedible oils offers a promising mean to reduce the cost of feedstocks and avoid the competition with edible oil market. Here we demonstrate a series of inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes (Ar/PrSO3H–Si(Et)Si) by a toluene swollen mixed Pluronic surfactant micelle-templating co-condensation route for transesterification of tripalmitin or plant oils with methanol to produce fatty acid methyl esters and esterification of glycerol with lauric acid to produce mono- and di-glycerol esters. By combination of superstrong Br?nsted acidity, unique hollow tubular nanostructure, excellent porosity properties and hydrophobic surface, the Ar/PrSO3H–Si(Et)Si nanotubes display higher catalytic activity as compared with acidic resin and zeolite. Additionally, the inner diameters and lengths of Ar/PrSO3H–Si(Et)Si nanotubes influence the activity obviously. The Ar/PrSO3H–Si(Et)Si nanotubes also show excellent catalytic reusability, attributing to covalent bonding of Ar/PrSO3H groups within silica/carbon framework and surface hydrophobicity of the catalysts.
- Guo, Yihang,Liu, Jingyu,Song, Daiyu,Wu, Qingyin,Zhang, Chaoyue,Zhang, Qingqing
-
-
- Enzymatic esterification of lauric acid to give monolaurin in a microreactor
-
Monolaurin is a naturally occurring compound widely utilized in food and cosmetics. In this paper, we present a new method for the synthesis of monolaurin by esterification between lauric acid and glycerol catalyzed by Novozym 435 using a microreactor. The conversion of lauric acid is 87.04% in 20 min, compared with 70.54% via the batch approach in 5 h. Using an optimized solvent system consisting of t-BuOH/tert-amyl alcohol (1:1, v/v), the selectivity using the microreactor method is enhanced to 90.63% and the space–time yield of the process is 380.91 g/h/L. This newly devised method has the potential for application to other multiphase and enzymatic reactions.
- Li, Xin,Miao, Shanshan
-
p. 660 - 667
(2021/03/03)
-
- MANUFACTURING METHOD OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE, AND MANUFACTURING DEVICE OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE
-
PROBLEM TO BE SOLVED: To provide a method capable of manufacturing a middle chain aliphatic acid triglyceride having good color tone and excellent stability, and a manufacturing device using the method. SOLUTION: There is disclosed a manufacturing method of middle chain aliphatic acid triglyceride and a manufacturing device of middle chain aliphatic acid triglyceride. The manufacturing method includes (a) a process for supplying a reaction system containing middle chain aliphatic acid and glycerin to an esterification reaction to obtain a reaction product containing the middle chain aliphatic acid triglyceride, (b) a process for removing unreacted middle chain aliphatic acid from the reaction product to obtain a reacted de-aliphatic acid product, and (c) a process for distilling the reacted de-aliphatic acid product using a thin film distillation machine to obtain a distilled product. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2019,JPOandINPIT
- -
-
Paragraph 0144-0152
(2019/08/12)
-
- Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids
-
The biocatalytic synthesis of monoacylglycerides (MAGs) was carried out by the direct esterification of fatty acids (i.e. capric, lauric, myristic, palmitic and oleic acids, respectively) with glycerol in different ionic liquids (ILs) based on cations with long alkyl side-chains (e.g. 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C16mim][NTf2], 1-dodecyl-3-methylimidazolium tetrafluoroborate [C12mim][BF4], etc.). Although all ILs have been shown as suitable reaction media for Novozym 435-catalyzed esterification of glycerol with free fatty acids, a high selectivity of MAGs was only observed in the [C12mim][BF4] case (e.g. up to 100% selectivity and 100% yield for monolaurin). Furthermore, as these ILs are temperature switchable ionic liquid/solid phases that behave as sponge-like systems, a straightforward protocol for IL-free MAG recovery, based on iterative centrifugations at controlled temperature, has been developed.
- Lozano, Pedro,Gomez, Celia,Nieto, Susana,Sanchez-Gomez, Gregorio,García-Verdugo, Eduardo,Luis, Santiago V.
-
p. 390 - 396
(2017/08/14)
-
- For producing fatty acid triglyceride method and of esterification reaction of esterification reaction device
-
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.
- -
-
Paragraph 0034-0035
(2017/03/21)
-
- LDH-catalyzed esterification of lauric acid with glycerol in solvent-free system
-
Direct esterification of waste oil materials (high FFA contents) and glycerol can be an important way to improve the energy goals and afford alternative sources to emulsifier production for food and cosmetics industry. This work reports an experimental study of free-solvent esterification of lauric acid with glycerol using a LDH (layered double hydroxide, Mg-Al-CO3) as catalyst. The experiments were performed in a mechanically stirred reactor evaluating the effect of temperature (100-180 C), lauric acid to glycerol molar ratio (1:1-3:1) and catalyst content (2-8 wt%). The results showed that relative high glycerol conversions (99%) can be obtained for the lauric acid esterification with glycerol leading to monolaurine and dilaurine. Results show that free-solvent LDH-catalyzed lauric acid esterification with glycerol might be a potential alternative route to conventional methods, as high contents of reaction products and selectivity was achieved. Furthermore, the results show that the LDH catalyst used was able to drive the reaction to the equilibrium in a relative short time - up to two hours.
- Hamerski, Fabiane,Corazza, Marcos L.
-
p. 242 - 248
(2014/03/21)
-
- METHOD FOR THE PREPARATION OF TRIGLYCERIDES OF MEDIUM-CHAIN LENGTH FATTY ACIDS
-
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.
- -
-
Paragraph 0040-0041
(2013/09/12)
-
- Glycerol eutectics as sustainable solvent systems
-
In this work the use of glycerol as a hydrogen bond donor in Deep Eutectic Solvents is studied. The physical properties of choline chloride mixtures with glycerol are quantified and it is shown that eutectic mixtures can circumvent some of the difficulties of using glycerol as a solvent viz. high viscosity and high melting point. The solvent properties are characterised using polarity parameters and the values are similar to other ionic liquids although it is shown that this procedure is a poor method of characterising Lewis basicity. The application of these liquids to the esterification of glycerol is used as a demonstration of the ability to tune a reaction with the quaternary ammonium halide acting as a quasi-protecting group. The liquids represent a sustainable way of preparing non-toxic, tuneable solvent systems.
- Abbott, Andrew P.,Harris, Robert C.,Ryder, Karl S.,D'Agostino, Carmine,Gladden, Lynn F.,Mantle, Mick D.
-
scheme or table
p. 82 - 90
(2011/04/12)
-
- Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
-
Glycerol-fatty acid esterification has been conducted with lipase from Penicillium camembertii lipase immobilized on epoxy SiO2-PVA in solvent-free media, with the major product being 1-monoglyceride, a useful food emulsifier. For a given set of initial conditions, the influence of reaction was measured in terms of product formation and selectivity using different fatty acids as acyl donors. Results were found to be relatively dependent of the chain length of the fatty acids, showing high specificity for both myristic and palmytic acids attaining final mixture that fulfills the requirements established by the World Health Organization to be used as food emulsifiers.
- Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
-
experimental part
p. 87 - 90
(2010/10/19)
-
- High purity palm monoglycerides
-
The present invention relates to a process for producing high purity monoglycerides from edible oils/fats and fatty acids through glycerolysis, in particular but not exclusively to the production of monoglycerides from palm oil and palm oil products. This is achieved by providing a process for the production of monoglycerides of fatty acids or fats and oils, comprising the steps of reacting fatty acids or fats and oils with excess glycerol in the presence of an acidic or alkaline catalyst; substantially separating the crude reaction product from the other reaction components; removing unwanted reaction components from the crude reaction product by washing; drying the reaction product.
- -
-
Page/Page column 5
(2008/06/13)
-
- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
-
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
-
p. 839 - 843
(2007/10/03)
-
- Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides
-
Glycerol was esterified with an equimolar amount of lauric acid to monolaurin using zeolites, sulfonic resins, and sulfonic mesoporous materials as catalysts. The latter were obtained by immobilization of 3-mercaptopropyl groups and oxidation with H2O2. In particular, fatty acid conversions, monoglyceride yields, and selectivities obtained with mesoporous (ordered, amorphous) sulfonic catalysts were compared with those of other heterogeneous or homogeneous catalysts.When using silica gel coated with propylsulfonic acids, high reaction rates are coupled to high monoglyceride yields, e.g., 53% mono yield for a 1:1 glycerol:lauric acid ratio. Minimizing the autocatalytic contribution of the fatty acid reactant is a critical issue. The influence of a number of reaction parameters is investigated. The mesoporous sulfonic catalysts are also employed in the esterification of propanediols and meso-erythritol, and for reactions with other fatty acids.
- Bossaert, Wim D.,De Vos, Dirk E.,Van Rhijn, Wim M.,Bullen, Joren,Grobet, Piet J.,Jacobs, Pierre A.
-
p. 156 - 164
(2007/10/03)
-
- Biocatalytic esterification in supercritical carbon dioxide by using a lipid-coated lipase
-
A lipid-coated lipase is soluble and acts as a more efficient catalyst for triglyceride syntheses in supercritical carbon dioxide (scCO2) than in conventional organic solvents, and the reactivity can be controlled reversibly by changing pressure and temperature in scCO2.
- Mori, Toshiaki,Kobayashi, Atsushi,Okahata, Yoshio
-
p. 921 - 922
(2007/10/03)
-
- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
-
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
-
p. 155 - 171
(2007/10/03)
-
- Preparation of a Lipid-Coated Lipase and Catalysis of Glyceride Ester Syntheses in Homogeneous Organic Solvents
-
A lipid-coated lipase was prepared by mixing aqueous solutions of lipase and dialkyl amphiphiles: A hydrophilic surface of the enzyme is converted with a lipid layer, of which lipophilic two-long-alkyl tails solubilize the enzyme in hydrophobic organic solvents.The lipid-coated lipase was prepared in various conditions by changing hydrophilic head groups of lipid molecules, a ratio of lipid/lipase, and an origin of lipase; the complex prepared from nonionic amphiphiles and lipase D from Rhizopus delemar showed a high stability and a high enzymatic activity in hydrophobic organic solutions.The lipid-coated lipase catalyzed di- and triacylglycerol syntheses from monoacylglycerols and aliphatic acids in the homogeneous and dry benzene solution in the presence of two pieces of molecular sieves (water: 80 ppm). the lipid-coated lipase could also catalyze ester exchange reactions in organic solvents with a small amount of water (250 ppm).Enzymatic activity was effected by a nature of organic solvents and a water content in organic solvents.The catalytic activity of the lipid-coated lipase was highly efficient compared with other enzyme systems such as the poly(ethylene glycol)-grafted lipase and the direct dispersion of lipase powder for glyceride syntheses in the dry organic solution.
- Okahata, Yoshio,Ijiro, Kuniharu
-
p. 2411 - 2420
(2007/10/02)
-
- Fat Hydrolysis and Esterification by a Lipase from Humicola lanuginosa
-
The hydrolysis and esterification by a thermostable lipase from Humicola lanuginosa No. 3 were investigated.Both reactions occurred readily at temperatures between 45-50 deg C.Esterification by the enzyme with glycerol was observed to be specific towards fatty acids with carbon numbers of C12-C18.Lauric acid esters with different alcohols such as primary alcohols, terpene alcohols, etc., were also synthesized readily.Esterification by the enzyme was adversely affected by the water content (optimum, ca. 7percent), however, the hydrolysis rate increased rapidly with increasing water content (optimum, ca. 60percent).The enzyme showed increased activity in organic solvent-aqueous reaction systems.Nevertheless, hydrolysis in complete organic phase reactions was found not to be feasible.Hydrolysis at a higher temperature (50 or 55 deg C) in a solvent free phase was almost the same as that in organic solvent-aqueous phase reactions.The components of glycerides varied considerably during hydrolysis, whereby esterification resulted in a higher quantity of mono- and diglycerides (about 40percent), compared to in the case of hydrolysis, for which the value was about 10-20percent.
- Omar, Ibrahim Che,Nishio, Naomichi,Nagai, Shiro
-
p. 2153 - 2160
(2007/10/02)
-
- A CONVENIENT METHOD OF ESTERIFICATION OF FATTY ACIDS. PREPARATION OF ALKYL ESTERS, STEROL ESTERS, WAX ESTERS AND TRIACYLGLYCEROLS
-
A quick and mild, one-pot method of esterification of fatty acids with pripary, secondary and tertiary alcohols as well as with fatty alcohols, sterols and glycerol is proposed via the acyl bromides formed in situ.
- Saroja, M.,Kaimal, T. N. B.
-
p. 1423 - 1430
(2007/10/02)
-
- Topical corticosteroid formulations
-
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.
- -
-
-
- Coal tar gel composition
-
Compositions effective for topically treating skin conditions, especially psoriasis and eczema which contains as an essential ingredient coal tar in a gel base.
- -
-
-
- Speckle particle for dentifrice
-
Functional speckle particle suitable for use in dentifrice containing allantoin, aluminum dihydroxy allantoinate (ALDA) or aluminum chlorohydroxyallantoinate (ALCA). The speckle is effective in promoting healing of inflamed and bleeding gums or periodontal tissue.
- -
-
-