16409-45-3Relevant academic research and scientific papers
A Method For Preparing (Meth)Acrylic Acid Ester Based Compound
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Paragraph 0071-0072, (2021/05/07)
The invention relates to a method for preparing a (meth)acrylic acid ester-based compound, and according to the preparation method, a (meth)acrylic acid ester-based compound can be prepared with high purity and high yield, by easily introducing an acrylic structure into alcohol using a diamine-based compound and acid anhydride.
IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
Talukdar, Ranadeep
supporting information, p. 5303 - 5308 (2020/04/17)
An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification
Adarme, Carlos A.A.,Le?o, Raquel A.C.,de Souza, Stefania P.,Itabaiana, Ivaldo,de Souza, Rodrigo O.M.A.,Rezende, Claudia M.
, p. 39 - 46 (2018/05/22)
Monoterpenic esters are very important flavor and fragrance compounds due to their organoleptic properties. Despite their importance, many drawbacks are found for the production of monoterpenic esters. Here in we report two different approach's (chemo and enzymatic) for the continuous production of monoterpenic esters with integrated purification arriving on the desired molecules with high yields (>95%) and short reaction times.
Production of l-menthyl acetate through kinetic resolution by?Candida cylindracea lipase: effects of alkaloids as additives
Belkacemi, Fatima Zohra,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
, p. 6847 - 6860 (2018/07/15)
Abstract: Enzymatic transesterification of dl-menthol with vinyl acetate in tert-Butyl methyl ether (TBME) catalyzed by Candida cylindracea lipase (CCL) was carried out in the presence of cinchona alkaloid as additive. The effects of various reaction parameters, such as lipase nature and loading, acylating agent, molecular sieves, solvents and various additives, on the reactivity as well as on the enantioselectivity were investigated. A significant improvement of CCL reactivity has been recorded after using cinchona alkaloid as additive in TBME. A high enantiomeric ratio (E = 80) was achieved when 30?mol% of quinidine was added, and l-(-)-menthyl acetate was obtained with 93% optical purity and 49% conversion. This process was easily applied to gram-scale quantities, using commercially inexpensive lipase, providing high yield optically active menthol under mild experimental conditions. Graphical abstract: [Figure not available: see fulltext.].
Enantioselective enzymatic resolution of racemic alcohols by lipases in green organic solvents
Belafriekh, Abderahmane,Secundo, Francesco,Serra, Stefano,Djeghaba, Zeineddine
, p. 473 - 478 (2017/03/23)
The effects of two eco-friendly solvents, 2-methyltetrahydrofuran (MeTHF) and cyclopentyl methyl ether (CPME), on the enzyme activity and enantioselectivity of Novozym 435, Candida rugosa lipase (CRL), Porcine pancreas lipase (PPL), Lipase AK, Lipase PS, and Lipozyme, a series of commercial lipases, in the enantioselective transesterfications of racemic menthol, racemic sulcatol and racemic α-cyclogeraniol were studied. Vinyl acetate was chosen as the acyl donor and the reactions were carried out at water activity 0.06. The activity of lipases in CPME was similar to that observed in other largely employed organic solvents [toluene and tert-butyl methyl ether (MTBE)], and was slightly lower in MeTHF. However, for most of the lipases tested, the enantioselectivity was higher in the eco-friendly solvents. Lipase AK exhibited a high enantioselectivity (E?=?232) for the resolution of racemic menthol but the reaction rate was low. Lipase formulation (the enzyme was frozen and lyophilized in potassium phosphate buffer without and with 5% (w/v) of sucrose, D-mannitol, or methoxy poly(ethylene glycol)) was tested with this lipase in order to improve its activity, which increased up to 4.5 times, compared to the untreated enzyme. CALB was found to be a useful biocatalyst for the resolution of racemic sulcatol, where high activity and enantioselectivity were obtained (E?≥?1000). For the resolution of the racemic primary alcohol α-cyclogeraniol, most of the lipases tested were active but not enantioselective, except lipase PS which displayed a moderate enantioselectivity (E?=?19). The effect of the presence of a low percentage of two ionic liquids (ILs) 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM][TFSI]) (5% (v/v)) and 1-Butyl-3-methylimidazoliumtetrafluoroborate ([BMIM][BF4]) (1% (v/v)) in the medium was also investigated. Only in the case of CRL the ILs slightly increased the enantioselectivity from E?=?91 to E?=?103 and E?=?120 for [BMIM][TFSI] and [BMIM][BF4], respectively. However, in all cases ILs caused a decrease of enzyme activity.
Proton-gradient-transfer acid complexes and their catalytic performance for the synthesis of geranyl acetate
Chen, Yongle,Ding, Shiya,Zheng, Wentao,Zhang, Yiyang,Wu, Youting,Hu, Xingbang
, p. 2114 - 2121 (2017/01/16)
Special proton-gradient-transfer acid complexes (PGTACs) in which the bonded protons are not equivalent and have gradients in transfer ability, acidity, and reactivity were reported. The acidity gradient of the protons gave the PGTACs excellent catalytic activity and selectivity in the esterification of terpenols. These PGTACs are “reaction-induced self-separation catalysts” and can be easily reused. The kinetics with PGTACs as catalyst in the esterification of geraniol were also studied for use in engineering design.
P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
Shirini, Farhad,Fallah-Shojaei, Abdollah,Abedini, Masoumeh,Samavi, Laleh
, p. 1699 - 1712 (2016/07/27)
P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.
Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: Acetylation of nopol and terpenic alcohols
Costa, Vinicius V.,Da Silva Rocha, Kelly A.,Oliveira, Luiz C. A.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.,Gusevskaya, Elena V.
, p. 43217 - 43222 (2016/05/24)
The cesium salt of tungstophosphoric heteropoly acid, Cs2.5H0.5PW12O40, is an active and environmentally friendly heterogeneous catalyst for the liquid-phase acetylation of nopol and several biomass-derived terpenic alcohols (i.e., α-terpineol, nerol, geraniol, linalool, menthol, isoborneol, perillyl alcohol, carveol, isopulegol, carvacrol and nerolidol) with acetic anhydride. The resulting flavor and fragrance acetic esters, which are widely used in perfumery, household and food products, are obtained in good to excellent yields. The reactions occur at room temperature with low catalyst loadings without substantial catalyst leaching and can be performed with stoichiometric amounts of an acetylating agent in solvent free systems.
Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO
Albadi, Jalal,Alihosseinzadeh, Amir,Mardani, Mehdi
, p. 308 - 313 (2015/09/28)
A new method has been developed for the chemoselective acetylation of alcohols with acetic anhydride in the presence of phenols using a novel, recyclable CuO-ZnO nanocatalyst. The catalyst was synthesized using the co-precipitation method and characterized by N2 adsorption-desorption, X-ray diffraction, scanning electron microscopy, transmission electron microscopy and energy dispersion scanning analyses. Furthermore, this catalyst could be recycled up to six times without significant loss in its activity.
