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.
Effect of Hydrogen Bond Donor on the Physical Properties of Benzyltriethylammonium Chloride Based Deep Eutectic Solvents and Their Usage in 2-Ethyl-Hexyl Acetate Synthesis as a Catalyst
Taysun, M. Bengi,Sert, Emine,Atalay, Ferhan S.
, p. 1173 - 1181 (2017)
Deep eutectic solvents (DES) containing benzyl triethylammonium chloride (BTEAC) as a hydrogen bond acceptor (HBA) and p-toluene sulfonic acid (PTSA), citric acid (CA), and oxalic acid (OX) as a hydrogen bond donor (HBD) were formed at their respective eutectic points. The physical properties such as pH, ionic conductivity, viscosity, density, and refractive index were measured between 293 and 333 K. Viscosity values as low as 0.21 Pa·s and conductivity values as high as 8 mS/cm were achieved, where the pH values of each DES proved to be extremely low. The effect of HBD on the physical properties was investigated and was found to be very significant. Also, the catalytic application of BTEAC based DES in the esterification reaction of the acetic acid with 2-ethyl-hexanol was studied, and the activation energy was obtained using initial reaction rates. The results showed that very high initial reaction rates and low activation energy can be achieved when catalyzed by DES which was formed using BTEAC and PTSA.
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.
Cobalt polyoxometalate, CoW12O405- as a new reusable catalyst for the direct, fast, and efficient acetylation of alcohols and phenols under solventless conditions
Habibi,Tangestaninejad,Mirkhani,Yadollahi
, p. 863 - 867 (2002)
Alcohols and phenols were efficiently acetylated with acetic anhydride without solvent in the presence of 0.01 molar equiv. of cobalt polyoxometalate (CoW12O405-).
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.
Cerium polyoxometalate as a reusable catalyst for acetylation and formylation of alcohols
Mirkhani, Valiollah,Tangestaninejad, Shahram,Moghadam, Majid,Yadollahi, Bahram,Alipanah, Ladan
, p. 1257 - 1263 (2004)
Efficient esterification of primary and sterically-hindered secondary or tertiary alcohols with acetic anhydride was achieved in the presence of ammonium decatungestocerate(IV) icosahydrate, (NH4)8[CeW 10O36]·OH2O, as catalyst in high yields. Primary and secondary alcohols were also converted to their corresponding acetates and formates with acetic acid and ethyl formate in the presence of this catalyst. Easy work-up, non-toxicity, reusability, and stability of the catalyst are noteworthy advantages of this method. Springer-Verlag 2004.
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.
Acidic ionic liquid based UiO-67 type MOFs: A stable and efficient heterogeneous catalyst for esterification
Xu, Zichen,Zhao, Guoying,Ullah, Latif,Wang, Meng,Wang, Aoyun,Zhang, Yanqiang,Zhang, Suojiang
, p. 10009 - 10016 (2018)
A facile strategy for the synthesis of acidic ionic liquid based UiO-67 type MOFs was developed in this study. Br?nsted acids (H2SO4, CF3SO3H and hifpOSO3H (hexafluoroisopropyl sulfuric acid)) were introduced into UiO-67-bpy (bpy = 2,2′-bipyridine-5,5′-dicarboxylic acid) frameworks by reacting with bipyridyl nitrogen to introduce the properties of an acidic ionic liquid into the frameworks. The prepared catalysts, denoted as UiO-67-HSO4, UiO-67-CF3SO3 and UiO-67-hifpOSO3, were characterized by XRD, SEM, FT-IR, EA, TGA and N2 adsorption-desorption studies. The relatively high surface area was still maintained and acidic active groups were uniformly dispersed in the frameworks. The catalytic performance of UiO-67-HSO4, UiO-67-CF3SO3 and UiO-67-hifpOSO3 was evaluated by the esterification of acetic acid with isooctyl alcohol. The prepared catalysts showed good catalytic activities in the esterification, of which UiO-67-CF3SO3 gave the maximum isooctyl alcohol conversion of 98.6% under optimized conditions. The catalyst could be reused five times without a significant decrease in the conversion of isooctyl alcohol, and almost no active species were leached, indicating the excellent stability and reusability of the catalyst. Our study provides one effective way to synthesize heterogeneous acidic ionic liquid catalysts consisting of isolated, well defined acidic groups that will probably attract interest in acid catalyst chemistry.
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.
Catalytic acetylation of alcohols and phenols with potassium dodecatungstocobaltate trihydrate
Habibi, Mohammad H.,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yadollahi, Bahram
, p. 323 - 327 (2002)
Alcohols and phenols are converted to esters in a mild, clean, and efficient reaction with acetic anhydride in the presence of a catalytic amount of potassium dodecatungstocobaltate trihydrate (K5CoW12O40· 3H2O).
