Kinetics of reaction of benzyl chloride with sodium acetate/benzoate: phase transfer catalysis in solid-liquid system

Yadav, Ganapati D.; Sharma, Man Mohan

doi:10.1021/i200013a032

Cited by 60 publications

(40 citation statements)

References 11 publications

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“…First one is the n o n -s o l u b l e s y s t e m ( h e t e r o g e n e o u s solubilization) introduced by Doraiswamy and Naik [21] and other is soluble system (homogeneous solubilization) introduced by Yadav and Sharma [22]. In this work, β-naphthol dissolved in the organic solvent with the addition of quaternary ammonium salt (QBr).…”

Section: Reaction Mechanism and Kinetic Modelmentioning

confidence: 99%

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Abimannan¹,

Rajendran²

2016

Bull. Chem. React. Eng. Catal.

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In this paper, the synthesis of ethyl 2-(naphthalen-2-yloxy)acetate from β-naphthol and ethyl 2-bromoacetate under ultrasound and catalyzed by quaternary ammonium salt in solid-liquid heterogeneous condition was described. Trace amount of water play a major role in this solid-liquid reaction. The reaction follows pseudo first order rate law. The apparent rate constant of the organic phase reaction was obtained form the experimental data. The combination of small amount of tetrabutylammonium bromide (TBAB) and ultrasound (kapp = 25.22×10 -3 min -1 ) shows several fold enhanced rate of the reaction than the conventional operation (kapp = 6.42×10 -3 min -1 for TBAB only). The rate constant increases (0.05 to 0.3 g) with increase in the concentration of catalyst (from kapp = 10.12×10 -3 min -1 to kapp = 34.46×10 -3 min -1 ). The other kinetic effects such as, effect of agitation speed, kind of frequency of ultrasound, kind of various quantity of K2CO3, quantity of water, temperature, different quaternary ammonium salts, solvents and volume of organic solvents on the conversion of ethyl 2-bromoacetate and apparent rate constant were investigated in detail and rational explanations are provided.

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Section: Reaction Mechanism and Kinetic Modelmentioning

confidence: 99%

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Abimannan¹,

Rajendran²

2016

Bull. Chem. React. Eng. Catal.

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“…While L-L PTC involves heterogeneous reaction between two reagents located in an aqueous, and an organic phase, S-L PTC involves reaction of an anionic reagent in a solid phase (usually a salt) with a reactant located in a continuous organic phase. Yadav and Sharma [5] proposed the first mechanistic and kinetic model of solid-liquid PTC followed by Naik and Doraiswamy [6]. We have carried out the detailed mechanistic and modelling studies for industrially important reactions under S-L PTC conditions [7,8].…”

Section: Introductionmentioning

confidence: 99%

Novelties of solid–liquid phase transfer catalysed synthesis of p-toluenesulfonyl fluoride from p-toluenesulfonyl chloride

Yadav

Paranjape

2005

Journal of Fluorine Chemistry

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Organic sulfonyl fluorides are of interest owing to their insecticidal, germicidal and enzyme inhibitory properties. In the current work, synthesis of p-toluenesufonyl fluoride was accomplished by reacting p-toluenesulfonyl chloride with solid potassium fluoride using PEG-400 as a catalyst under solid-liquid phase transfer catalysis (S-L PTC) at 30 8C. p-Toluenesulfonyl fluoride is used as peroxygen bleach activator. It also finds use in the treatment of Alzheimer's disease. The mechanism is based on homogeneous solubilization of solid. PEG forms a complex with metal cation which associates with the nucleophile and it participates in SN 2 type reactions. The reaction is intrinsically kinetically controlled. A complete theoretical analysis is done to determine both the rate constant and equilibrium constant from the same set of data. The activation energy and Gibbs free energy are also calculated. #

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“…For liquid-liquid phase-transfer catalysis (LLPTC), by contrast, the anion reactant in the aqueous phase reacts with a soluble catalyst to form the catalytic intermediate, which then transfers into the organic phase to conduct the intrinsic organic reaction. Yadav and Sharma [3] investigated the kinetics of reaction of benzyl chloride with sodium acetate/benzoate by SLPTC and found that cetyldimethylbenzylammonium chloride was the most efficient catalyst among those studied. Yang and Wu [4] investigated the reaction of dipotassium phthalate with benzyl bromide and concluded that the esterification can be carried out effectively in SLPTC even without water addition; the behaviors of the active intermediate were also reported.…”

Section: Introductionmentioning

confidence: 99%

Kinetics for synthesizing benzyl salicylate via solid–liquid phase-transfer catalysis

Yang

Liu

2004

Applied Catalysis A: General

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The kinetics for synthesizing benzyl salicylate (C 6 H 4 (OH)COOCH 2 C 6 H 5 , denoted as Ph(OH)COOR) from the carboxylation of benzyl bromide (C 6 H 5 CH 2 Br, RBr) via solid-liquid phase-transfer catalysis (SLPTC) was investigated. The key component to conduct the substitution reaction is the catalytic intermediate generated from solid sodium salicylate (C 6 H 4 (OH)COONa, denoted as Ph(OH)COONa) reacted with tetraalkylammonium salt. The concentration of catalytic intermediate remained nearly constant after the induction period and increased with the increase of the amount of catalyst employed. The reaction between catalytic intermediate and organic reactant is identified as the controlling step. Factors affecting the formation of the catalytic intermediate include the relative amounts of catalyst, solid reactant, organic reactant, and extra addition of inorganic salts. Different phase-transfer catalysts were employed to compare their catalytic efficiency: tetra-n-butylammonium bromide (Bu 4 NBr, TBAB or QBr in general) > tetra-n-butylammonium iodide (TBAI) > tetra-n-butylphosphonium bromide (TBPB) > aliquat 336 > tetra-n-butylammonium hydrogen sulfate (TBAHS) > polyethylene glycol (PEG) 1500. The product yield above 98% was achieved within 1 h at 70 • C by using tetra-n-butylammonium bromide as the catalyst. A kinetic model was developed for the solid-liquid reaction. The overall reaction can be described by pseudo-first-order kinetics with the apparent activation energy in chlorobenzene to be 62.52 kJ mol −1 .

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Kinetics of reaction of benzyl chloride with sodium acetate/benzoate: phase transfer catalysis in solid-liquid system

Cited by 60 publications

References 11 publications

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Novelties of solid–liquid phase transfer catalysed synthesis of p-toluenesulfonyl fluoride from p-toluenesulfonyl chloride

Kinetics for synthesizing benzyl salicylate via solid–liquid phase-transfer catalysis

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