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.
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.
Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups
Cauvel, Anne,Renard, Gilbert,Brunel, Daniel
, p. 749 - 751 (1997)
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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.
LDH-catalyzed esterification of lauric acid with glycerol in solvent-free system
Hamerski, Fabiane,Corazza, Marcos L.
, p. 242 - 248 (2014)
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 PREPARING MONOGLYCERIDES
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Paragraph 0076-0078, (2020/08/18)
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
