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DOP Process 2

The document studies the kinetics of esterification of phthalic anhydride with 2-ethylhexanol using methane sulphonic acid and para-toluene sulphonic acid as catalysts, finding that the reaction follows second order kinetics. It also analyzes the advantages and disadvantages of various catalysts, including traditional acids, alkyl titanates, solid acid catalysts, heteropolyacids, and functionalized ionic liquids. The research highlights the challenges in achieving high yields of di-octyl phthalate due to by-product formation and catalyst deactivation.

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Manish Tikle
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20 views2 pages

DOP Process 2

The document studies the kinetics of esterification of phthalic anhydride with 2-ethylhexanol using methane sulphonic acid and para-toluene sulphonic acid as catalysts, finding that the reaction follows second order kinetics. It also analyzes the advantages and disadvantages of various catalysts, including traditional acids, alkyl titanates, solid acid catalysts, heteropolyacids, and functionalized ionic liquids. The research highlights the challenges in achieving high yields of di-octyl phthalate due to by-product formation and catalyst deactivation.

Uploaded by

Manish Tikle
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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ESTERIFICATION OF PHTHALIC ANHYDRIDE

WITH 2-ETHYLHEXANOL
Satchidanand R Satpute1, Yogesh H Shinde2, Prakash V Chavan1*
1
Department of Chemical Engineering, College of Engineering, Bharati Vidyapeeth Deemed University,
Dhanakwadi, Pune- 411046, India
2
Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai-400019, India
Email: [email protected], [email protected]

ABSTRACT:

The kinetics of esterification of phthalic anhydride (PAN) with 2-ethylhexanol (2EH) has been studied using

methane sulphonic acid (MSA) and para- toluene sulphonic acid (p-TSA) as a catalyst. In each case, the kinetic

parameters (rate constant, order with respect to reactants and catalyst, activation energy, and collision frequency)

have been determined. It has been found that the reaction follows an overall second order kinetics, first order with

respect to each reactant. The order with respect to both the catalysts has also been determined and it has been found

that the reaction shows first order dependence on catalyst concentration. Furthermore, the literature pertaining to the

synthesis of di-octyl phthalate (DOP) has been critically analysed and reported in the present work.

Key words: Di-2-ethyhexyl phthalate, Phthalic anhydride, 2- Ethyl hexanol, Esterification, Kinetics

1. INTRODUCTION
DOP, synthesized by esterification of PAN with 2EH, is the most widely used plasticizer. Normally
sulphuric acid and p-TSA are used as a catalyst. Sulphuric acid and p-TSA, however, suffer from the disadvantage of
by-product formation and colouration of the product due to various side reactions with increasing temperatures, in
particular. In comparison with sulphuric acid and p-TSA, the non-acidic alkyl titanates have the advantage of very
low by-product formation.1, 2 Their activity, however, is much lower than that of the Bronsted acids, necessitating
reaction temperature of more than 2000C. Further, the titanates also suffer from the disadvantages of higher cost and
difficult separation from the products. The solid acid catalysts overcome the disadvantages of Bronsted acids and
titanates.3 Nevertheless, they suffer from disadvantages of easily deactivation, operation loss, and high mass transfer
resistance.
The heteropolyacids (HPAs) have also been used to catalyze the esterification reaction in the presence of
low boiling carrier liquid like benzene, toluene, xylene, and dichloromethane to remove the water azeotropically.4
The use of low boiling carrier, however, tends to reduce the rate of esterification reaction. In addition, the HPAs
catalyze both, the esterification and hydrolysis reactions which result into lower yield of DOP at a given temperature.
Further, their activity reduces drastically with a reuse. Recently, functionalized ionic liquids have also been exercised
to catalyse the esterification reaction.5 The pertinent dispersion of ionic liquid in the reaction phase is, however,
necessary during the course of reaction to obtain high yield of DOP. In addition, some ionic liquid gradually
decomposes under a given reaction conditions which results into dissolution of ionic liquid in the reaction mixture,
giving poor yield of DOP. The ionic liquids also associated with the disadvantages like reduction of catalytic activity
with reuse and colorization of the product.

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