Kinetics of Transesterification of Methyl Acetate and <i>n</i>-Butanol Catalyzed by Ionic Liquid

Cui, Xianbao; Cai, Jialin; Zhang, Ying; Li, Rui; Feng, Tingting

doi:10.1021/ie2000715

Cited by 36 publications

(48 citation statements)

References 27 publications

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“…Moreover, the study highlighted that the catalytic activity increased with increasing acidity of the ILs and particularly with cations bearing SO 3 H anions (Scheme 5: ILs I , II , III , and IV ). The same imidazolium salts ( I and II , respectively) have been used also by Cui et al for the transesterification of methyl acetate and n- butanol [47]. The authors observed that the presence of two acidic sites in both the cation and the anion of ILs improved the performance of the catalyst, in analogy to previously reported results for the synthesis of esters from the reaction of nitriles and alcohols [48].…”

Section: Reviewmentioning

confidence: 57%

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

Selva¹,

Perosa²,

Guidi³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe use of ionic liquids (ILs) as organocatalysts is reviewed for transesterification reactions, specifically for the conversion of nontoxic compounds such as dialkyl carbonates to both linear mono-transesterification products or alkylene carbonates. An introductory survey compares pros and cons of classic catalysts based on both acidic and basic systems, to ionic liquids. Then, innovative green syntheses of task-specific ILs and their representative applications are introduced to detail the efficiency and highly selective outcome of ILs-catalyzed transesterification reactions. A mechanistic hypothesis is discussed by the concept of cooperative catalysis based on the dual (electrophilic/nucleophilic) activation of reactants.

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Section: Reviewmentioning

confidence: 57%

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

Selva¹,

Perosa²,

Guidi³

et al. 2016

Beilstein J. Org. Chem.

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“…The activity coefficient c i is calculated by the UNIQUAC model and the parameters needed are obtained from the literature reported [22,24]. k ?…”

Section: Effects Of Catalyst Concentrationmentioning

confidence: 99%

“…, E A-are 40.89 and 40.85 kJ/mol. Cui et al [24] have applied a NIH model to describe the same reaction catalyzed by an acidic IL and the active energies E A? , E A-are 36.26 and 36.02 kJ/mol.…”

Section: Effects Of Catalyst Concentrationmentioning

confidence: 99%

“…But the transesterification catalyzed by ILs is different from that catalyzed by acidic ion-exchange resin, because the former is homogenous and the latter is heterogeneous. Cui et al have proposed two kinetic models, the ideal homogeneous (IH) model and the nonideal homogeneous (NIH) model, for the transesterification of methyl acetate and n-butanol catalyzed by an acidic IL [24].…”

mentioning

confidence: 99%

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Transesterification of Methyl Acetate with n-Butanol Catalyzed by Single and Mixed Ionic Liquids

Yang

Cui

Yu³

et al. 2015

Catal Lett

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Several acidic ionic liquids (ILs) with different cations and anions were used as catalysts in the transesterification of methyl acetate with n-butanol. The IL [omim][PF 6 ] can enhance the catalytic activity of the partially soluble IL catalyst. The kinetics for the transesterification using the catalysts [HSO 3 bmim][p-TS] and [HSO 3 bmim][OTF] were measured. The ideal homogeneous model and the nonideal homogeneous (NIH) model were used to correlate the kinetic data. The NIH model was more reliable to describe the reaction rate. Graphical Abstract 0 50 100 150 200 250 300 350 400 450 0.0 0.1 0.2 0.3 0.4 0.5 0.6 [HSO 3 bmim][CL] [HSO 3 bmim][OTF] [HSO 3 bpy][OTF] [HSO 3 bmim][p-TS] [HSO 3 Hmim][HSO 4 ],ref 24 Conversion of methyl acetate Time (min) Abbreviations IL Ionic liquid MRD Mean relative deviation BuOH n-Butanol MeOAc Methyl acetate [HSO 3 bmim][Cl] 1-Sulfobutyl-3-methylimidazolium chloride [HSO 3 bmim][OTF] 1-Sulfobutyl-3-methylimidazolium trifluoromethanesulfonate [HSO 3 bmim][p-TS] 1-Sulfobutyl -3-methylimidazolium tosylate [HSO 3 bpy][OTF] N-sulfobutylpyridinium trifluoromethanesulfonate [HSO 3 bHim][HSO 4 ] 1-Sulfobutylimidazolium hydrogensulfate [omim][PF 6 ] 1-Octyl-3-methylimidazolium hexafluorophosphateVariables r 0 Initial reaction rate (mol/(L min)) rReaction rate (mol/(L min)) cMole concentration (mol/L) E Constant defined in Eq 2 c cat Mole concentration of ionic liquid catalysts (mol/L) k ?Forward reaction rate constant (L 2 /(min mol 2 )) kBackward reaction rate constant (L 2 /(min mol 2 )) k 0 þ Arrhenius pre-exponential factors (L 2 /(min mol 2 )) k 0 À Arrhenius pre-exponential factors (L 2 /(min mol 2 )) E A? Activation energy of forward reaction (kJ/mol) E A-Activation energy of backward reaction (kJ/mol) V Volume of the reaction mixture (L)

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“…We assume that [HSO 3 Pmim]HSO 4 can quickly provide protons and the dissociation process is in equilibrium state. The initial reaction rate r 0 is a function [21] of catalyst concentration c cat ,…”

Section: Kinetic Modelmentioning

confidence: 99%

Reaction kinetics for synthesis of sec-butyl alcohol catalyzed by acid-functionalized ionic liquid

Qiu

Tang

et al. 2015

Chinese Journal of Chemical Engineering

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Kinetics of Transesterification of Methyl Acetate and n-Butanol Catalyzed by Ionic Liquid

Cited by 36 publications

References 27 publications

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

Transesterification of Methyl Acetate with n-Butanol Catalyzed by Single and Mixed Ionic Liquids

Reaction kinetics for synthesis of sec-butyl alcohol catalyzed by acid-functionalized ionic liquid

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