The Role of Water in Phase Transfer Catalysis

Sasson, Yoel; Arrad, Onn; Dermeik, S.; Zahalka, Hayder A.; Weiss, M.; Wiener, Harold

doi:10.1080/00268948808070274

Cited by 19 publications

(14 citation statements)

References 25 publications

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“…PTC is one of the most efficient methods that can be used to carry out a variety of chemical reactions under mild conditions with improved results. Adoption of PTC technique in industry provides cost reduction and pollution prevention which are highly significant in the era of green chemistry [3][4][5]. There are reports on using permanganate and chromate as oxidizing agent in organic synthesis under PTC [6][7][8][9][10][11][12] but reports on the use of hypochlorite as oxidant in synthetic preparation of organic compounds are scanty [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Benzaldehydes by Hypochlorite Oxidation of Benzyl Alcohols under Phase Transfer Catalysis

Bijudas¹,

Bashpa²,

Bibin³

et al. 2014

Bull. Chem. React. Eng. Catal.

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The selective synthesis of benazaldehyde and substituted benzaldehydes from corresponding benzyl alcohols has been carried out by using hypochlorite as an oxidant in organic medium under phase transfer catalysis. The reaction is highly selective since no traces of benzoic acid or substituted benzoic acids have been detected and the yield is found to be more than 90%. The products obtained were precipitated as 2,4-dinitrophenylhydrazone and the recrystallised products were characterized by melting point and by spectrophotometric techniques like infra red and UV-Visible analysis.

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Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Benzaldehydes by Hypochlorite Oxidation of Benzyl Alcohols under Phase Transfer Catalysis

Bijudas¹,

Bashpa²,

Bibin³

et al. 2014

Bull. Chem. React. Eng. Catal.

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“…In order to reaction take place, the pinch of phase-transfer catalyst was added to the reaction system. The phasetransfer agent must forming active catalyst with the reactant anion from the aqueous or solid phase and transports it through the interfacial region into the organic phase [5] for an ion-pair extraction of normal phase-transfer catalysis. Undoubtedly, PTC offers many substantial advantages for the practical execution of numerous reactions [6].…”

Section: Introductionmentioning

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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“…However, the insolubility of such initiators in organic solvents and monomers makes their use impractical for the polymerization. Fortunately, thanks to phase transfer catalyst (PTC) reaction methodology [12][13][14][15][16][17], phase transfer catalyst facilitates the migration of a reactant from one phase to another in which the reaction occurs, which avoids mass transfer limitations and increases the efficiency of twophase system. This type of catalyst is very versatile for synthesis of polymers and organic compounds in both academia and industry because of its simple experimental process, mild reaction conditions, being inexpensive and the possibility to be implemented on a large scale [18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Ultrasonic condition boosts up the rate of phase transfer catalyzed polymerization of acrylonitrile in two-phase system

Marimuthu

Murugesan

2017

Appl Petrochem Res

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An ultrasound condition associated with phasetransfer catalyst (PTC) has great diverse applications in synthesis of various organic and polymeric materials because of its fast reaction and high yield in short period of time. Phase transfer catalyst (cetyltrimethylammonium bromide as PTC) extracts the reactive radical anion from aqueous phase and transfer to organic phase whilst ultrasound condition enhances the radical formation; consequently, acrylonitrile was polymerized in ethyl acetate/ water two-phase system at 60 ± 1°C under ultrasound (25 kHz/300 W) and silent condition. The rate of polymerization (R p ) was doubled under ultrasound compare to silent condition. The various experimental parameters such as monomer, initiator, catalyst and temperature, solvent polarity on the rate of polymerization was studied in both conditions. The activation energy (E a ) and other thermodynamic parameters were calculated. The E a value of ultrasound condition supports the enhancement of rate of polymerization. On the basis of observed results, a suitable kinetic model, mechanism and effect of ultrasound in the rate of polymerization were discussed. The obtained polymer was analyzed by TG/DTA and FT-IR. The viscosity average molecular weight of the polymer was found to be 6.8526 9 10 4 g mol -1 .

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The Role of Water in Phase Transfer Catalysis

Cited by 19 publications

References 25 publications

Selective Synthesis of Benzaldehydes by Hypochlorite Oxidation of Benzyl Alcohols under Phase Transfer Catalysis

Selective Synthesis of Benzaldehydes by Hypochlorite Oxidation of Benzyl Alcohols under Phase Transfer Catalysis

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

Ultrasonic condition boosts up the rate of phase transfer catalyzed polymerization of acrylonitrile in two-phase system

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