Home Experimental and Kinetic Study of Esterification of Acrylic Acid with Ethanol Using Homogeneous Catalyst
Article
Licensed
Unlicensed Requires Authentication

Experimental and Kinetic Study of Esterification of Acrylic Acid with Ethanol Using Homogeneous Catalyst

  • Ghoshna Jyoti , Amit Keshav EMAIL logo and J. Anandkumar
Published/Copyright: March 12, 2016

Abstract

Esterification of acrylic acid with ethanol, catalyzed by sulfuric acid has been carried out in stirred batch reactor under atmospheric pressure. Different parameters such as effect of initial molar ratios of the reactants, effect of catalyst concentration, initial water and effect of temperature has been studied in the batch reactor. Different catalyst loading system (1–3 vol%), reaction temperatures (50–70 °C), initial reactants molar ratio (1:1–1:3) and water concentration in feed (0–20 vol%) was used in the reaction system. The temperature dependence is exponential and expressed by Arrhenius type of relationship. Kinetics parameters such as equilibrium constant, rate constants, activation energy and reaction enthalpy and entropy were estimated by experimental data. The rate equation has a remarkable fit to the data and was able to describe the behavior of the system at various reaction temperatures. Hydrochloric acid (HCl) and hydro iodic acid (HI) were also compared with sulphuric acid as catalyst for esterification of acrylic acid with ethanol. Sulphuric acid was found to be more efficient catalyst for esterification as it induces the maximum conversion of acrylic acid.

Award Identifier / Grant number: SB/FTP/ETA-97/2012

Funding statement: This work was supported by the DST, Ministry of Science and Technology, New Delhi, India (SB/FTP/ETA-97/2012).

Nomenclature

CA

concentration of acrylic acid (mol/m3)

CB

concentration of ethyl alcohol (mol/m3)

CE

concentration of ethyl acrylate (mol/m3)

CW

concentration of water (mol/m3)

CC

concentration of catalyst (mol/m3)

CA0

initial concentration of acrylic acid (mol/m3)

CB0

initial concentration of ethyl alcohol (mol/m3)

k1

forward reaction rate constant ((m3)2/kmol2.min)

k–1

backward reaction rate constant ((m3)2/kmol2.min)

t

reaction time (min)

T

reaction temperature (°C)

Keq

equilibrium constant

XA

conversion of acrylic acid

XAe

equilibrium conversion of acrylic acid

R

rate constant (8.314 J/mol K)

ΔH

reaction enthalpy (J/mol)

ΔS

reaction entropy (J/mol K)

Ea

activation energy (J/mol)

References

1. Aafaqi, R., Mohamed, A.R., Bhatia, S., 2004. Kinetics of Esterification of Palmitic Acid with Isopropanol Using p-toluene Sulfonic Acid and Zinc Ethanoate Supported Over Silica Gel as Catalysts. J. Chem. Technol. Biotechnol. 79, 1127–1134.10.1002/jctb.1102Search in Google Scholar

2. Ali, S.H., Tarakmah, A., Merchant, S.Q., Al-Sahhaf, T., 2007. Synthesis of Esters: Development of the Rate Expression for the Dowex 50 Wx8-400 Catalyzed Esterification of Propionic Acid with 1-Propanol. Chem. Eng. Sci. 62, 3197–3217.10.1016/j.ces.2007.03.017Search in Google Scholar

3. Akbay, E.O., Altiokka, M.R., 2011. Kinetics of Esterification of Acetic Acid with n-Amyl Alcohol in the Presence of Amberlyst-36. Appl. Catal. A: Gen. 396, 14–19.10.1016/j.apcata.2011.01.013Search in Google Scholar

4. Altiokka, M.R., Citak, A., 2003. Kinetics Study of Esterification of Acetic Acid with Isobutanol in the Presence of Amberlite Catalyst. Appl. Catal. A Gen. 239, 141–148.10.1016/S0926-860X(02)00381-2Search in Google Scholar

5. Altiokka, M.R., Odes, E., 2009. Reaction Kinetics of the Catalytic Esterification of Acrylic Acid with Propylene Glycol. Appl. Catal. A: Gen. 362, 115–120.10.1016/j.apcata.2009.04.028Search in Google Scholar

6. Bart, H.J., Reidetschlager, J., Schatka, K., Lehmann, A., 1994. Kinetics of Esterification of Levulinic Acid with n-Butanol by Homogeneous Catalysis. Ind. Eng. Chem. Res. 33, 21–25.10.1021/ie00025a004Search in Google Scholar

7. Chen, X., Xu, Z., Okuhara, T., 1999. Liquid Phase Esterification of Acrylic Acid with 1-Butanol Catalyzed by Solid Acid Catalysts. Appl. Catal. A: Gen. 180, 261–269.10.1016/S0926-860X(98)00337-8Search in Google Scholar

8. Ganesh, B., Yamuna Rani, K., Styavthi, B., Venkateswrlu Ch., 2011. Development of Kinetic Models for Acid-Catalyzed Methyl Acetate Formation Reaction: Effect of Catalyst Concentration and Water Inhibition. Int. J. Chem. Kinet. 43, 263–277.10.1002/kin.20555Search in Google Scholar

9. Jagadeesh Babu, P.E., Sandesh, K., Saidutta, M.B., 2011. Kinetics of Esterification of Acetic Acid with Methanol in the Presence of Ion Exchange Resin Catalysts. Ind. Eng. Chem. Res. 50, 7155–7160.10.1021/ie101755rSearch in Google Scholar

10. Ju, I.B., Lim, H., Jeon, W., Suh, D.J., Park, M., Suh, Y., 2011. Kinetic Study of Catalytic Esterification of Butyric Acid and n-Butanol Over Dowex. Chem. Eng. J. 168, 293–302.10.1016/j.cej.2010.12.086Search in Google Scholar

11. Korkmaz, S., Salt, Y., Hasanoglu, A., Ozkan, S., Salt, I., Dincer, S., 2009. Pervaporation Membrane Reactor Study for the Esterification of Acetic Acid and Isobutanol Using Polydimethylsiloxane Membrane. Appl. Catal. A Gen. 366, 102–107.10.1016/j.apcata.2009.06.037Search in Google Scholar

12. Lilja, J., Murzin, D.Y., Salmi, T., Aumo, J., Mäki-arvela, P., Sundell, M., 2002. Esterification of Different Acids Over Heterogeneous and Homogeneous Catalysts and Correlation with the Taft Equation. J. Mol. Catal. A: Chem 182–183, 555–563.10.1016/S1381-1169(01)00495-2Search in Google Scholar

13. Liu, W., Tan, C., 2001. Liquid-Phase Esterification of Propionic Acid with n –Butanol. Ind. Eng. Chem. Res. 40, 3281–3286.10.1021/ie001059hSearch in Google Scholar

14. Liu, Y., Lotero, E., Goodwin, J.G., 2006a. Effect of Carbon Chain Length on Esterification of Carboxylic Acids with Methanol Using Acid Catalysis. J. Catal. 243, 221–228.10.1016/j.jcat.2006.07.013Search in Google Scholar

15. Liu, Y., Lotero, E., Goodwin, J.G., 2006b. Effect of Water on Sulfuric Acid Catalyzed Esterification. J. Mol. Catal. A: Chem. 245, 132–140.10.1016/j.molcata.2005.09.049Search in Google Scholar

16. Malshe, V.C., Chandalia, S.B., 1977. Kinetics of the Liquid Phase Esterification of Acrylic Acid with Methanol and Ethanol. Chem. Eng. Sci. 32, 1530–1531.10.1016/0009-2509(77)80251-0Search in Google Scholar

17. Mekala, M., Goli, V.R., 2015. Kinetics of Esterification of Methanol and Acetic Acid with Mineral Homogeneous Acid Catalyst. Chin. J. Chem. Eng. 23, 100–105.10.1016/j.cjche.2013.08.002Search in Google Scholar

18. Ronnback, R., Salmi, T., Vuori, A., Juha, H.H., Sundqvist, A., Tirronen, E., 1997. Development of a Kinetic Model for the Esterification of Acetic Acid with Methanol in the Presence of a Homogeneous Acid Catalyst. Chem. Eng. Sci. 52, 3369–3381.10.1016/S0009-2509(97)00139-5Search in Google Scholar

19. Sert, E., Buluklu, A.D., Karakuş, S., Atalay, F.S., 2013. Kinetic Study of Catalytic Esterification of Acrylic Acid with Butanol Catalyzed by Different Ion Exchange Resins. Chem. Eng. Process. Process Intensif. 73, 23–28.10.1016/j.cep.2013.06.004Search in Google Scholar

20. Truong, H.T., Rode, S., Roizard, D., Mouzon-Pelletier, S., Tretjak, S., 2012. Pervaporation of the Esterification Reaction Mixture of Ethyl Acrylate with Commercial Membranes. Procedia Eng. 44, 1590–1592.10.1016/j.proeng.2012.08.877Search in Google Scholar

21. Wasewar, K., Patidar, S., Agarwal, V.K., 2009. Esterification of Lactic Acid with Ethanol in a Pervaporation Reactor: Modeling and Performance Study. Desalination 243, 305–313.10.1016/j.desal.2008.04.030Search in Google Scholar

22. Yadav, G.D., Thathagar, M.B., 2002. Esterification of Maleic Acid with Ethanol Over Cation-Exchange Resin Catalysts. React. Funct. Polym. 52, 99.10.1016/S1381-5148(02)00086-XSearch in Google Scholar

Published Online: 2016-3-12
Published in Print: 2016-4-1

©2016 by De Gruyter

Downloaded on 16.11.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ijcre-2015-0131/pdf?lang=en
Scroll to top button