103-09-3Relevant articles and documents
Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterifications
Xu, Zhenjin,Wan, Hui,Miao, Jinmei,Han, Mingjuan,Yang, Cao,Guan, Guofeng
, p. 152 - 157 (2010)
Polystyrene (PS)-supported 1-(propyl-3-sulfonate) imidazolium hydrosulfate acidic ionic liquid (PS-CH2-[SO3H-pIM][HSO4]) catalyst was prepared by supporting the ionic liquid onto highly cross-linked chloromethylated polystyrene (PS-CH2Cl). FT-IR, SEM and TG-DSC were employed to characterize the structure and property of the catalyst. Results suggested that acidic ionic liquid was supported onto the surface of PS-CH 2Cl by covalent bond. The original rough surface of PS-CH 2Cl was covered with acidic ionic liquid, forming a compact and thin surface layer, and its size had no obvious change. Moreover, the PS-CH 2-[SO3H-pIM][HSO4] catalyst showed a better thermal stability than that of PS-CH2Cl support. It also exhibited high catalytic activity for a series of esterifications. After the catalyst was reused for 13 times in the synthesis of n-butyl acetate, the yield only decreased 7.3%. A reaction mechanism of esterification over this new catalyst was proposed as well.
Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non-aqueous reaction medium
Dhake, Kishor P.,Deshmukh, Krishna M.,Wagh, Yogesh S.,Singhal, Rekha S.,Bhanage, Bhalchandra M.
, p. 15 - 23 (2012)
In present study, the application of steapsin lipase (as a biocatalyst) was investigated for kinetic resolution of secondary alcohols (1-phenyl ethanol and their derivatives) using vinyl acetate as an activated acyl donor. The enzymatic protocol was optimized for various reaction parameters such as effect of the molar ratio, solvent, temperature, time and biocatalyst loading to obtain best reaction conditions. On optimization, developed enzymatic methodology provided considerable enantiomeric excess of the product (up to 92% ee) at 55 °C in n-hexane as a solvent. Furthermore using the developed protocol, synthesis of several industrially important acetates was successfully achieved with excellent yield (up to 99%). During acetate synthesis, the biocatalyst was remarkably reused for eight consecutive recycles without any significant loss in its catalytic activity. This revealed the good potential of steapsin lipase for application in organic solvents.
Microwave-Assisted Catalytic Acetylation of Alcohols by Gold-Nanoparticle-Supported Gadolinium Complex
Chang, Tsao-Ching,Yu, Shuchun Joyce
, p. 661 - 672 (2015)
A gold nanoparticle (AuNP)-supported gadolinium complex (RS-Au-L-Gd) catalyst was prepared through simple chelation of GdCl3 to the surface-bound spacer, 1,4,7-tris(carboxymethyl)-10-(11-mercaptoundecyl)-1,4,7,10-tetraazacyclododecane (HSDO3A). This AuNP-supported Gd complex was found to be a highly effective catalyst for the acetylation of various alcohols and phenol in the presence of acetic anhydride. With a loading of 0.4 mol% of RS-Au-L-Gd, the almost complete transformation can be achieved in 60 s under microwave irradiation conditions. This hybrid catalyst was air stable, water soluble, dissolvable in many organic media, and precipitable. It can be readily recycled more than eight times without any significant loss of its catalytic activity. GRAPHICAL ABSTRACT.
Deep eutectic solvent choline chloride·2CrCl3·6H2O: An efficient catalyst for esterification of formic and acetic acid at room temperature
Cao, Jin,Qi, Bin,Liu, Jun,Shang, Yuhan,Liu, Huiwen,Wang, Wenjing,Lv, Jia,Chen, Zhiyan,Zhang, Haibo,Zhou, Xiaohai
, p. 21612 - 21616 (2016)
A highly efficient and selective method for esterification of formic and acetic acid with alcohols has been achieved at room temperature, with the choline chloride (ChCl)/chromium(iii) chloride hexahydrate (CrCl3·6H2O) deep eutectic solvent as a catalyst. High yields and good selectivities of organic esters are obtained using DES [ChCl][CrCl3·6H2O]2 with the molar ratio 5:1 (carboxylic acids:alcohols) at room temperature in 24 h. The ease of recovery and reusability of DES with high catalytic activity makes this method efficient and practical.
Synthesis of 2-ethylhexyl acetate by transesterification of methyl acetate with 2-ethylhexanol
Yin, Lina,Wang, Dazhi,Qu, Fengzuo,Jia, Lin,Zhang, Shaoyin
, p. 2861 - 2864 (2015)
In order to explore a new application field of methyl acetate which is of limited industrial importance, one of the possibilities to obtain the desired products would be the transesterification of methyl acetate with 2-ethylhexanol. The choice of catalyst and the determination of the best experimental conditions for the transesterification were investigated in this paper. Strongly acidic cation-exchange resin NKC-9 was chose as the catalyst in this reaction. The reaction time, the effects of the reaction temperature, the catalyst loading and the molar ratio of methyl acetate to 2-ethylhexyl acetate on the conversion of 2-ethylhexyl acetate were discussed. This paper describes an optimization study on the transesterification reaction based on nine well-planned orthogonal experiments. The maximum conversion of 2-ethylhexanol was found at a NKC-9 catalyst loading of 20 wt. %, a molar ratio of methyl acetate to 2-ethylhexanol of 4:1, a reactive time of 3 h and a reaction temperature of 80 °C. The product yield and the conversion of 2-ethylhexanol under optimal conditions reached 90.90 and 79.64 %, respectively. The structure of the product 2-2-ethylhexyl acetate acetate has been conformed by IR and 1H NMR.
A synthesis of copper based metal-organic framework for O-acetylation of alcohols
Singh, Savita J.,Kale, Sandip R.,Gawande, Manoj B.,Velhinho,Jayaram, Radha V.
, p. 24 - 28 (2014)
A novel metal-organic framework, Cu-BDC was synthesized by static hydrothermal method using innocuous solvents and characterized by several techniques such as powder XRD, ESR, TG-DTA, elemental analysis, ICP-AES, SEM, EDXS, FT-IR, BET surface area, pore volume and pore size. The catalytic performance of Cu-BDC was explored for O-acetylation of alcohols under solvent-free conditions at room temperature. The catalyst exhibited remarkable activity and reusability affording the desired products in excellent yields.
Novel catalytic acetylation and formylation of alcohols with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O)
Habibi, Mohammad H,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yadollahi, Bahram
, p. 8333 - 8337 (2001)
Acetylation and formylation reactions of alcohols with ethyl acetate, acetic acid and ethyl formate were catalyzed with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O) in a mild, efficient and convenient method with high to excellent yields.
Synthesis of lipase nano-bio-conjugates as an efficient biocatalyst: Characterization and activity-stability studies with potential biocatalytic applications
Badgujar, Kirtikumar Chandulal,Sasaki, Takehiko,Bhanage, Bhalchandra Mahadeo
, p. 55238 - 55251 (2015)
In the present study, we have synthesized lipase-nano-bio-conjugates via immobilization of various lipases on multiwall carbon nano-tubes (MCNT), in order to construct an efficient and recyclable biocatalytic system. In a screening study lipase Pseudomonas fluorescens (PFL) acted as an efficient biocatalyst (lipase-nano-bio-conjugates) which showed higher retention of lipase activity and protein loading. Consequently the immobilization support : lipase (MCNT : PFL) composition was screened in which MCNT : PFL (2 : 1) was calculated as a robust biocatalyst composition which showed higher activity retention and protein loading. This nano-bio-conjugate was then characterized in detail with physical and biochemical techniques using SEM, TEM, FTIR, Km, Vmax, catalytic efficiency and (%) water content analysis. This developed biocatalyst was further used for practical biocatalytic applications such as O-acylation reactions. Various reaction parameters were optimized in detail like reactant molar ratio (2 : 3.5), solvent, MCNT : PFL biocatalyst amount (36 mg), temperature (50°C) etc. The developed biocatalytic protocol was then extended to synthesize several (twenty-two) industrially important acylated moieties with an excellent yield, these products are well characterized by 1HNMR, 13CNMR and GCMS analysis. Moreover in the present study, we have reviewed the potential industrial applications of various synthesized compounds. Also, we have studied the thermodynamic aspect which demonstrated more feasibility of use of immobilized MCNT : PFL lipase over free lipase. Interestingly, immobilized MCNT : PFL lipase showed 2.3 fold higher catalytic activity than free PFL. Besides this, the biocatalyst was efficiently recycled for up to five cycles. Thus the present protocol demonstrated, (i) synthesis of nano-bio-conjugates as a bio-catalyst, (ii) detailed physical-biochemical characterization of nano-bio-conjugates, (iii) optimization of the biocatalytic protocol (iv) practical biocatalytic applications along with a mechanistic study (v) a thermodynamic feasibility study and (vi) recyclability study. 2015
A sun-screening agent to the methoxy cinnamic acid process of isooctyl ester (by machine translation)
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Paragraph 0024-0033, (2018/04/01)
The invention relates to a sun-screening agent to the methoxy cinnamic acid isooctyl (OMC) clean synthetic process. The process adopts a one-pot preparation of methoxy cinnamic acid isooctyl: in a small amount of toluene sulfonic acid under the catalysis of the methyl acetate and isooctanol under isooctyl ester exchange reaction to produce acetic acid, then, in the sodium methoxide under the catalysis of the formaldehyde with the methoxyl condensation reaction, generating to the methoxy cinnamic acid ester. This invention adopts the advanced good ester exchange reaction and then condensation reaction process flow of expensive raw materials to help to improve the utilization rate of the methoxy benzaldehyde, in the process of synthesis does not use any other solvent, no waste water is produced, safety and environmental protection, and the product yield is as high as 97% or more. (by machine translation)
