124-06-1Relevant articles and documents
Electrochemical Tandem Olefination and Hydrogenation Reaction with Ammonia
Zhang, Xiaofeng,Jiang, Runze,Cheng, Xu
, p. 16016 - 16025 (2021/08/24)
An electrochemical Horner-Wadsworth-Emmons/hydrogenation tandem reaction was achieved using ammonia as electron and proton donors. The reaction could give two-carbon-elongated ester and nitrile from aldehyde or ketones directly. This reaction could proceed with a catalytic amount of base or even without a base. The ammonia provides both the electron and proton for this tandem reaction and enables the catalyst-free hydrogenation of an α,β-unsaturated HWE intermediate. More than 40 examples were reported, and functional groups, including heterocycles and hydroxyl, were tolerated.
Novel synthesized microporous ionic polymer applications in transesterification of Jatropha curcas seed oil with short Chain alcohol
Chang, Tao,Hao, Yongjing,Jinxi, Jinxi,Kai, Kai,Panchal, Balaji,Qin, Shenjun,Sun, Yuzhuang,Zhao, Cunling,Zhao, Qiaojing,Zhu, Zheng
, (2021/09/28)
New suites of sulfonic acid-functionalized microporous ionic polymers (PIPs) catalysts were synthesized with polymer, alkyl bromides, and 1, 3-propane sultone via a two-step procedure. The synthesized microporous PIP catalysts were characterized using FT-IR, SEM-Mapping, XPS, N2 adsorption–desorption isotherms, solid NMR spectroscopy, and element analysis. Esterification of several fatty acids with ethanol, which was used as a model reaction in the stabilization of Jatropha curcas seed oil, was checked over functionalized PIP. We tested the catalytic performance of PIP-C8 on the synthesis of fatty acid esters via the transesterification of J. curcas seed oil with a mixture of short-chain alcohols such as ethanol, ethanol–to–diethyl carbonate (1;1 molar ratio), and ethanol–to–dimethyl carbonate (1:1 molar ratio) with 170 mg of PIP-C8 at reflux temperature with agitation. The PIP-C8 catalyst was particularly effective, having achieved yields of 85%, 94%, and 70% for J. curcas seed oil with ethanol, J. curcas seed oil with ethanol–to–DEC, and J. curcas seed oil with ethanol–to–DMC, respectively, under the optimized reaction conditions. The catalyst could be recycled more than five times without significant deactivation. Kinetic studies performed at different temperatures revealed that the conversion of oleic acid to an ethyl ester follows a first-order reaction. The best catalysts with microporous structure (average pore diameter: 1.7–1.9 nm, pore volume: 0.23–0.33 cm3 g–1) and –SO3H density (0.70–0.84 mmol/gcat) were obtained by 1, 3-propane sultone of the chemically activated. The results indicate that the site activity of functionalized microporous ionic polymer materials shows promising approach for the development of environmentally friendly technology.
NATURAL BIOSURFACTANT OF ESTER AND MANUFACTURING METHOD THEREOF
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Paragraph 0125; 0126; 0129-0132, (2020/12/11)
The present invention relates to an ester natural surfactant and a manufacturing method thereof. The present invention relates to an eco-friendly ester natural surfactant having excellent solubility in water and biodegradability, and a manufacturing method thereof. The present invention relates to an ester natural surfactant, and more particularly, to an ester natural surfactant and a method for preparing the same. (by machine translation)
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation
Betke, Tobias,Gr?ger, Harald,Kleber, Joscha,Liese, Andreas,Schlipk?ter, Kim E.
, p. 7862 - 7867 (2020/11/02)
Fatty alcohols are important products in chemical industry to be used in the formulation of surfactants and lubricants. This work describes a two step approach for the production of myristyl alcohol under neat conditions by combining a lipase catalyzed esterification of myristic acid and myristyl alcohol with a ruthenium catalyzed hydrogenation of the intermediate myristyl myristate. The esterification was carried out in a bubble column reactor with the commercial immobilized lipase B from Candida antarctica as a biocatalyst, while the hydrogenation was conducted under pressurized conditions being catalyzed by the homogeneous chemocatalyst Ru-Macho-BH. By investigating the reaction steps separately, comparable reaction rates were found for the esterification of short chain and long chain alcohols. Additionally, the hydrogen pressure could be reduced to 35 bar compared to the current industrial Lurgi process. Characterization of cross interactions by the reactants myristic acid and sodium myristate in the hydrogenation demonstrates that the metal catalyst was completely deactivated, even at a low amount of 0.5 mol% of myristic acid. Complete conversion of myristic acid in the esterification with equal amounts of myristic acid and myristyl alcohol was obtained, overcoming any limitation in the hydrogenation. In comparison to the Lurgi process starting also from fatty acid and fatty alcohols, the chemoenzymatic two step reaction sequence could be realized at lower reaction temperatures of 60 and 100 °C as well as lower hydrogen pressures of 35 bar. This journal is
Preparation method of long-chain ester
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Paragraph 0121; 0122; 0123, (2019/03/23)
The invention relates to the field of organic synthesis and provides a preparation method of long-chain ester, which comprises the following steps: carrying out esterification reaction of the carboxylic acid and the alcohol through a catalyst and obtaining a long-chain ester phase and a water phase post the standing and layering of the reaction liquid; the catalyst comprises ionic liquid or eutectic solvent; purifying and separating the long-chain ester phase to obtain high-purity long-chain ester; introducing the residual substance again into the esterification reaction system for reaction after the water in the water phase is removed. The yield and the purity of the long-chain ester prepared by the invented method are as high as 99.8% and 99% respectively as indicated by the embodiment of the preparation method.
Medium-chain fatty acids from Eugenia winzerlingii leaves causing insect settling deterrent, nematicidal, and phytotoxic effects
Cruz-Estrada, Angel,Ruiz-Sánchez, Esaú,Cristóbal-Alejo, Jairo,González-Coloma, Azucena,Andrés, María Fe,Gamboa-Angulo, Marcela
, (2019/05/27)
Eugenia winzerlingii (Myrtaceae) is an endemic plant from the Yucatan peninsula. Its organic extracts and fractions from leaves have been tested on two phloem-feeding insects, Bemisia tabaci and Myzus persicae, on two plant parasitic nematodes, Meloidogyne incognita and Meloidogyne javanica, and phytotoxicity on Lolium perenne and Solanum lycopersicum. Results showed that both the hexane extract and the ethyl acetate extract, as well as the fractions, have strong antifeedant and nematicidal effects. Gas chromatography-mass spectrometry analyses of methylated active fractions revealed the presence of a mixture of fatty acids. Authentic standards of detected fatty acids and methyl and ethyl derivatives were tested on target organisms. The most active compounds were decanoic, undecanoic, and dodecanoic acids. Methyl and ethyl ester derivatives had lower effects in comparison with free fatty acids. Dose-response experiments showed that undecanoic acid was the most potent compound with EC50 values of 21 and 6 nmol/cm2 for M. persicae and B. tabaci, respectively, and 192 and 64 nmol for M. incognita and M. javanica, respectively. In a phytotoxicity assay, medium-chain fatty acids caused a decrease of 38-52% in root length and 50-60% in leaf length of L. perenne, but no effects were observed on S. lycopersicum. This study highlights the importance of the genus Eugenia as a source of bioactive metabolites for plant pest management.
Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents
Jumina,Nurmala, Asma,Fitria, Anggit,Pranowo, Deni,Sholikhah, Eti Nurwening,Kurniawan, Yehezkiel Steven,Kuswandi, Bambang
, (2018/12/11)
In the present work, monoacylglycerol derivatives, i.e., 1-monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (1H- and13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.
Sulfonic acid-functionalized organic knitted porous polyaromatic microspheres as heterogeneous catalysts for biodiesel production
Varyambath, Anuraj,Kim, Mi-Ra,Kim, Il
, p. 12745 - 12753 (2018/08/04)
The use of renewable energy sources decreases the consequences of greenhouse gas emission from fossil fuels. Biodiesel, an easily burning and biodegradable fuel, is an alternative to conventional diesel fuel. The esterification of long-chain fatty acids and transesterification of triglycerides are two major reactions widely used to convert vegetable oils or animal fats into biodiesel. As solid acid catalysts are considered promising candidates for biodiesel production, we have synthesized a series of organic knitted porous polyaromatics (OPPs) using pyrene, anthracene, and naphthalene as monomers via Friedel-Crafts alkylation, followed by crosslinking reactions. The resultant polymers showed good surface morphology, stability and swelling property, high capacity for functionalization due to the unreacted bromomethyl groups on the surface, and excellent hydrophobicity. The sulfonated polymer microspheres obtained by the surface sulfonation showed good surface acidity; thus, they can be employed as heterogeneous solid acid catalysts for the esterification of long-chain fatty acids and transesterification of triglycerides, and they are reusable without any leaching of functional groups.
P-Sulfonic acid calix[4]arene-functionalized alkyl-bridged organosilica in esterification reactions
De Assis,Abranches,Braga,Zu?iga,Sathicq,Romanelli,Sato,Fernandes
, p. 24285 - 24289 (2016/03/15)
Two new p-sulfonic acid calix[4]arene- and p-sulfonic acid calix[6]arene-functionalized organosilica have been synthesized using a sol-gel method and applied as heterogeneous catalysts in esterification reactions. The catalytic performance was evaluated using the esterification of carboxylic acids with ethanol, and good catalytic activity (i.e., 55-88%) was observed under the optimum reaction conditions. This study reports the first promising example of the successful employment of calix[n]arenes as a heterogeneous catalyst for catalytic esterification. The catalyst was easily separated by filtration and reused five times without any significant loss of activity.
Use of Lecitase-Ultra immobilized on styrene-divinylbenzene beads as catalyst of esterification reactions: Effects of ultrasounds
Alves, Joana S.,Garcia-Galan, Cristina,Danelli, Daiane,Paludo, Natália,Barbosa, Oveimar,Rodrigues, Rafael C.,Fernandez-Lafuente, Roberto
, p. 27 - 32 (2015/08/06)
Abstract In this work it was evaluated for the first time, the ester synthesis catalyzed by the phospholipase Lecitase-Ultra immobilized styrene-divinylbenzene beads (MCI-Lecitase), comparing the mechanical stirring and the ultrasonic energy. It was studied the specificity of the enzyme using carboxylic acids from C4 to C18, as well as the effects of alcohol chain, organic solvents, biocatalyst content, reaction temperature and substrate concentration. Caprylic and myristic acids were those with the highest reaction rates and yields, using ethanol as substrate. The shorter the alcohol chain, the higher the enzyme activity. Regarding the secondary alcohols, while MCI-Lecitase had no activity versus isopropanol, using 2-pentanol the activity was similar to that with 1-pentanol. Comparing the agitation systems, MCI-Lecitase presented an initial reaction rate more than 2-times higher in the ultrasound-assisted reaction than under traditional mechanical stirring. Moreover, under ultrasonic energy the maximum rate was achieved using 0.5 M of substrates, while under mechanical stirring the maximum enzyme activity was reached at 0.3 M of substrates. Concerning the operational stability, MCI-Lecitase was quite unstable, losing its activity after 6 reaction cycles. By adding molecular sieves in the reaction medium, MCI-Lecitase retained 30% of its initial activity after 6 cycles.
