142-18-7Relevant articles and documents
Ionic Liquid–Silicotungstic Acid Composites as Efficient and Recyclable Catalysts for the Selective Esterification of Glycerol with Lauric Acid to Monolaurin
Han, Xiaoxiang,Zhang, Xiaofang,Zhu, Guangqi,Liang, Juanjuan,Cao, Xianghui,Kan, Renjun,Hung, Chin-Te,Liu, Li-Li,Liu, Shang-Bin
, p. 2727 - 2738 (2017)
The synthesis of glycerol monolaurate (GML) by the esterification of glycerol (GL) with lauric acid (LA) over a series of propyl sulfonic acid-functionalized ionic liquids (SAFILs)-modified silicotungstic acid (STA; H4SiW12O40) composite catalysts has been investigated. The synthesized organic–inorganic hybrid catalysts were characterized by different physicochemical techniques. In particular, their acidic properties were studied by solid-state 31P magic angle spinning (MAS) NMR spectroscopy by using adsorbed trimethylphosphine oxide (TMPO) as a probe. The effects of key reaction parameters, such as glycerol/lauric acid molar ratio, amount of catalyst, reaction time, and reaction temperature on LA conversion and GML product yield were elucidated and optimized with response surface methodology (RSM). The N,N-dimethyl(benzyl)ammonium propyl sulfobetaine (DMBPS)-modified STA [DMBPSH]H3SiW12O40 exhibited the optimal catalytic activity and was exploited for process optimization. A highest GML yield of 79.1 % was achieved with the optimized reaction conditions. The high catalytic activity of these hybrid catalysts were attributed to strong acidity, low transport resistance, and their “pseudoliquid” characteristics. A kinetic study was made based on a second-order irreversible model of the esterification reaction, which resulted in an activation energy of 39.49 kJ mol?1 for [DMBPSH]H3SiW12O40 under optimized reaction conditions.
Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides
Bossaert, Wim D.,De Vos, Dirk E.,Van Rhijn, Wim M.,Bullen, Joren,Grobet, Piet J.,Jacobs, Pierre A.
, p. 156 - 164 (1999)
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.
Enzymatic esterification of lauric acid to give monolaurin in a microreactor
Li, Xin,Miao, Shanshan
, p. 660 - 667 (2021)
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.
Synthesis and antibacterial activity of 1-monolaurin
Nitbani, Febri Odel,Jumina,Siswanta, Dwi,Sholikhah, Eti Nurwening,Fitriastuti, Dhina
, p. 863 - 867 (2018)
An improvement of method for synthesizing 1-monolaurin from lauric acid and glycerol has been done. The reaction was carried on mol ratio between lauric acid and glycerol 1:1 at 130 °C for 6 h with variation of pTSA catalyst of 2.5%, 5%, 7.5% (w/w of lauric acid). The purification of 1-monolaurin was conducted only by extracting with alcoholic solution. The product of 1-monolaurin was obtained as a white solid with 100% of purity from variation of 2.5% and 5% of pTSA catalyst with 43.54% and 27.89% yield, respectively. 1-Monolaurin could inhibit the growth of S. aureus and E. coli bacteria at 500 μg/mL of concentration.
Synthesis and tandem mass spectrometry of chlorinated triacylglycerols
Lefsay, Abir M.,Guy, Robert D.,Chatt, Amares,White, Robert L.
, p. 55 - 63 (2013)
The incorporation of 9,10-dichlorooctadecanoyl groups using enzyme-catalyzed acylation and protecting group strategies yielded specific regioisomers of di- and tetrachlorinated triacylglycerols. Hexachloroand hexabromotriacylglycerols were synthesized by addition of chlorine or bromine to tri-(cis-9-octadecenoyl)glycerol. Upon electrospray ionization and tandem mass spectrometry, the sodium adductions of all compounds containing a 9,10-dichlorooctadecanoyl group readily lost two molecules of HCl when subjected to collision-induced dissociation. A mechanism describing sequential HCl losses and the formation of a conjugated diene is proposed for the loss of both vicinal chlorine atoms from an alkyl chain. This characteristic fragmentation behavior and the availability of characterized standards will facilitate the development of quantitative analytical methods for the determination of chlorinated triacylglycerols in lipid mixtures isolated from marine and other biological sources.
Acid-catalyzed intra- and intermolecular acyl exchange in mono- and diglycerides
Isai,Usol'tsev,Stiba
, p. 325 - 329 (2003)
Acid-catalyzed transformation of 1-monolauroylglycerine (1-MLG) was investigated. It has been demonstrated that 1-MLG disproportionates readily and quickly into a mixture of 1,2- and 1,3-diacylglycerines and glycerine. The transformation of 1,3-diglycerides into 1,2-diglycerides was studied.
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
, (2022)
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.
Kinetics of acyl migration in monoglycerides and dependence on acyl chainlength
Boswinkel,Derksen,Van't Riet,Cuperus
, p. 707 - 711 (1996)
The chemical rearrangement reaction of β- into α-monoglycerides is described. Four monoglycerides with different fatty acid chainlength have been investigated, and the equilibrium constant and the reaction velocity constants characterizing the reaction of the chemical rearrangement were estimated with a mathematical model. A 1:6.5 mixture of α/β-monoglycerides appeared to rearrange to a mixture of 1:1 α/β-monoglycerides within 24 h. Furthermore, the reaction velocity of the rearrangement reaction of β- to α-monoglycerides depended on the fatty acyl chainlength in the monoglyceride.
Pore size control and organocatalytic properties of nanostructured silica hybrid materials containing amino and ammonium groups
El Hankari, Samir,Motos-Perez, Blanca,Hesemann, Peter,Bouhaouss, Ahmed,Moreau, Joel J. E.
, p. 6948 - 6955 (2011)
Periodic mesoporous organosilicas containing amine and ammonium substructures were synthesized via soft templating approaches using anionic surfactants. Pore size control was achieved either using anionic surfactants containing alkyl groups of variable chain lengths or by addition of swelling agents such as mesitylene (1,3,5-trimethylbenzene, TMB) to the hydrolysis-polycondensation mixture. The addition of mesitylene allows to increase the pore size in the materials from 2 to 6 nm. The materials appear as versatile and recyclable heterogeneous organocatalysts in Knoevenagel and Henry reactions and in the formation of monoglycerides by ring opening reaction of glycidol. This study highlights the huge potential of silica hybrid materials containing ionic substructures (i-silica) materials in heterogeneous catalysis.
Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
, p. 87 - 90 (2010)
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.
