538-24-9Relevant articles and documents
RETRACTED ARTICLE: Silica supported microporous melamine tri sulfonic acid catalyst towards biodiesel fuel production from waste cooking oil and utilization of side stream
Savaliya, Mehulkumar L.,Dholakiya, Bharatkumar Z.
, p. 12 - 21 (2015)
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.
Cellulose sulfuric acid catalyzed esterification of biodiesel derived raw glycerol to medium chain triglyceride: The dual advantage
Savaliya, Mehulkumar L.,Dholakiya, Bharatkumar Z.
, p. 1399 - 1406 (2014)
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.]
Lipase-catalyzed two-step esterification for solvent-free production of mixed lauric acid esters with antibacterial and antioxidative activities
Yu, Hyunjong,Byun, Yerim,Chang, Pahn-Shick
, (2021/08/01)
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.
Sustainable production of biodiesel and transformation of glycerol to glycerol laurate esters over inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes
Guo, Yihang,Liu, Jingyu,Song, Daiyu,Wu, Qingyin,Zhang, Chaoyue,Zhang, Qingqing
, (2021/01/11)
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.
Enzymatic esterification of lauric acid to give monolaurin in a microreactor
Li, Xin,Miao, Shanshan
, p. 660 - 667 (2021/03/03)
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.
MANUFACTURING METHOD OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE, AND MANUFACTURING DEVICE OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE
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Paragraph 0144-0152, (2019/08/12)
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
Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids
Lozano, Pedro,Gomez, Celia,Nieto, Susana,Sanchez-Gomez, Gregorio,García-Verdugo, Eduardo,Luis, Santiago V.
, p. 390 - 396 (2017/08/14)
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.
For producing fatty acid triglyceride method and of esterification reaction of esterification reaction device
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Paragraph 0034-0035, (2017/03/21)
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.
LDH-catalyzed esterification of lauric acid with glycerol in solvent-free system
Hamerski, Fabiane,Corazza, Marcos L.
, p. 242 - 248 (2014/03/21)
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.
METHOD FOR THE PREPARATION OF TRIGLYCERIDES OF MEDIUM-CHAIN LENGTH FATTY ACIDS
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Paragraph 0040-0041, (2013/09/12)
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.
