Thermodynamic Equilibrium For The Esterification of Acrylic Acid With Different Alcohols Catalyzed by Ion Exchange Resin

Thermodynamic equilibrium for the esterification of acrylic acid with
different alcohols catalyzed by ion exchange resin

E. Sert, S. Karaku, A. D. Buluklu, F. S. Atalay
Ege University, Chemical Engineering Department, 35100, Bornova, Izmir, Turkey;
Tel.: 90 232 311 1493, Fax: 90 232 388 7776, E-mail: simgekarakus@hotmail.com.
Esterification is a chemically reversible reaction producing ester and water from two
reactants of acid and alcohol. The desired product, ester, provides useful applications in
chemical industry, such as solvents, plasticizers, medicinal agents, flavors and fragrances [1].
However, esterification shows limited conversion due to low reaction rate and reversibility
[2]. Although the reaction rate and the conversion in esterification reactions can be enhanced
by varying several reaction parameters, including the elevation of temperatures, the increase
in alcohol-to-acid ratios and the utilization of more catalytically active sites (e.g., higher
concentration in the case of mineral acids), these can cause several drawbacks in industrial
applications such as corrosion, energy consuming product separation, and difficult and costly
recovery of the product.
The problem with low reaction rate can be resolved by the employment of suitable
catalysts. There are two catalysts to accelerate the rate of esterification reaction, that is,
homogeneous and heterogeneous catalyst. Mineral acid (H2SO4, HCl, and so on) and only
organic acid including HCOOH are typical acids for homogeneous acid catalysts [3].
Although homogeneous catalysts provide distinguished performance in terms of reaction rate,
the benefit of those catalysts is diminished since separation and recovery of catalyst are
difficult due to the miscibility between liquid acid catalyst and reaction medium [1,3]. In
addition, the homogeneous acid catalysts cause the corrosion of equipment, more side
reactions and additional neutralization cost to treat waste containing acids [4]. The ionexchange resin is a promising material for the replacement of the homogeneous acid catalysts.
The solid type of material has good physical and chemical properties, and shows
Esterification reactions are known to be equilibrium limited chemical reactions. The
reaction of a carboxylic acid and an alcohol results in the formation of the corresponding ester
and water molecules, where the overall reaction can be expressed as
Acrylic acid + Butanol/iso-Butanol/Hexanol Butyl/iso-Butyl/Hexyl acrylate + Water
In this study, equilibrium constants were determined for the esterification of acrylic
acid with butanol/iso-butanol and hexanol catalyzed by Amberlyst 131. Also the effects of
carbon chain length and OH group location on the thermodynamic equilibrium were
investigated.
Experiments were performed at four different temperatures by using Amberlyst 131 as
catalyst. Alcohol and acrylic acid (Merck) were used as the reactants. Initial volume of the
reaction mixture was approximately 300 mL. The experimental assembly was consisted of a
reactor fitted with a condenser to prevent any loss of products. The electrical heater was used
to heat the reaction mixture and batch content is stirred magnetically using a magnetic stirrer.
Temperature of the reaction mixture was controlled using a temperature controller. In a typical
run, alcohol, catalyst and phenothiazine as inhibitor were charged into the reaction vessel in a
predetermined ratio. The temperature of the reactor was set to the desired value. After the
desired temperature was reached, acrylic acid was added into the reactor and this was taken as
zero time for a run. All the experiments lasted long enough to ensure that the equilibrium was
reached.
Also, equilibrium constants at each temperature and temperature dependency of
equilibrium constant according to Vant Hoff equation were calculated.
The equilibrium constants and activity coefficients were determined theoretically by
using UNIQUAC method and compared with the experimental results.
References
1. S.H. Ali, A. Tarakmah, S.Q. Merchant, T. Al-Sahhaf, Chem. Eng. Sci. 62 (2007) 3197.
2. W.T. Liu, C.S. Tan, Ind. Eng. Chem. Res. 40 (2001) 3281.
3. J. Lilja, D.Y. Murzin, T. Salmi, J. Aumo, P. Mki-Arvela, M. Sundell, J. Mol. Catal. A:
Chem. 182183 (2002) 555.
4. I. Jua, H. Limb, W. Jeona, D. Suha, M. Parkb, Y. Suha, Chemical Engineering Journal 168
(2011) 293.

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Thermodynamic equilibrium for the esterification of acrylic acid with

different alcohols catalyzed by ion exchange resin

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