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KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36

Year 2017, Volume: 18 Issue: 5, 1098 - 1106, 31.12.2017
https://doi.org/10.18038/aubtda.310676

Abstract



The kinetics of esterification of acetic acid with 2-ethylhexanol
catalyzed by Amberlyst 36 was studied in a stirred batch reactor. The
equilibrium constant, Kc, was found to be 81 and it is independent
of temperature within the range of 333 to 363 K. The uncatalyzed reaction was
proved to follow a second-order reversible reaction model. In the presence of
Amberlyst 36, experimental data well fitted with a pseudo-homogeneous (PH)
model.




References

  • Kirk, R. E. Othmer, D. F. In Encyclopedia of Chemical Technology, CD-ROM, 4th Ed. New York: John Wiley and Sons, 2001.
  • BASF, Technical Information, Petrochemicals: 2-Ethylhexyl Acetate, 2016. http://www.solvents.basf.com/portal/streamer?fid=278918
  • Solomons, T. W. G. Fundamentals of Organic Chemistry. Canada: John Wiley and Sons, 1982.
  • Altiokka, M. R., Citak, A. Kinetics study of esterification of acetic acid with isobutanol in the presence of amberlite catalyst. Appl. Catal. A: Gen. 2003; 239: 141-148.
  • Blagov, S., Parada, S., Bailer, O., Moritz, P., Lam, D., Weinand, R., Hasse, H. Influence of ion-exchange resin catalysts on side reactions of the esterification of n-butanol with acetic acid. Chem. Eng. Sci. 2006; 61: 753-765.
  • Tsai, Y.-T., Lin, H.-M., Lee, M.-J. Kinetics behavior of esterification of acetic acid with methanol over Amberlyst 36. Chem. Eng. J. 2011; 171: 1367–1372.
  • Richard, R., Guillaume, D., Jacquin, M. Kinetics modeling of the heterogeneously catalyzed esterification of 2,3-Butanediol with acetic acid. Ind. Eng. Chem. Res. 2016; 55: 5247-5256.
  • Leyva, F., Orjuela, A., Miller, D. J., Gil, I., Vargas, J., Rodríguez, G. Kinetics of propionic acid and isoamyl alcohol liquid esterification with Amberlyst 70 as catalyst. Ind. Eng. Chem. Res. 2013; 52: 18153-18161.
  • Ali, S. H., Merchant, S. Q. Kinetics of the esterification of acetic acid with 2-propanol: Impact of different acidic cation exchange resins on reaction mechanism. Int J Chem Kinet 2006; 38: 593– 612.
  • Schmid, B., Dölker, M., Gmehling, J. Esterification of Ethylene Glycol with Acetic Acid Catalyzed by Amberlyst 36. Ind. Eng. Chem. Res. 2008; 47: 698-703.
  • Akbay, E. Ö., Altiokka, M. R. Kinetics of esterification of acetic acid with n-amyl alcohol in the presence of Amberlyst-36. Appl. Catal. A: Gen. 2011; 396: 14–19.
  • Akyalçın, S. Altıokka, M. R. Kinetics of esterification of acetic acid with 1-octanol in the presence of Amberlyst 36. Appl. Catal. A: Gen. 2012; 429-430: 79-84.
  • Schildhauer, T. J., Hoek, I., Kapteijn, F., Moulijn, J. A. Zeolite BEA catalysed esterification of hexanoic acid with 1-octanol: Kinetics, side reactions and the role of water. Appl. Catal. A: Gen. 2009; 358: 141–145.
  • Kirumakki, S. R., Nagaraju, N., Chary, K. V. R. Esterification of alcohols with acetic acid over zeolites Hβ, HY and HZSM5. Appl. Catal. A: Gen. 2006; 299: 185–192.
  • Do Nascimento, L. A. S., Angélica, R. S., Da Costa, C. E. F., Zamian, J. R., Da Rocha Filho, G. N. Comparative study between catalysts for esterification prepared from kaolins. Appl. Clay Sci. 2011; 51: 267–273.
  • Zatta, L., Gardolinski, J. E. F. da C., Wypych, F. Raw halloysite as reusable heterogeneous catalyst for esterification of lauric acid. Appl. Clay Sci. 2011; 51: 165–169.
  • Peters, T. A., Benes, N. E., Holmen, A., Keurentjes, J.T.F. Comparison of commercial solid acid catalysts for the esterification of acetic acid with butanol. Appl. Catal. A: Gen. 2006; 297: 182–188.
  • Liu, W. T., Tan, C. S. Liquid-phase esterification of propionic acid with n-butanol. Ind. Eng. Chem. Res. 2001; 40: 3281 ‒ 3286.
  • Ragaini, V., Bianchi, C.L., Pirola, C. Kinetics of esterification of diluted acetic acid with pure 2-ethyl-1-hexanol. Chemical Eng. J. 2007; 131: 257–262.
  • Rajkumar, T., Ranga Rao, G. Porous hydrous zirconia supported 12-tungstophosphoric acid catalysts for liquid-phase esterification of 2-ethyl-1-hexanol. J. Mol. Catal A: Chem. 2008; 295:1-9.
  • Gyani, V. C., Mahajani, S. Reactive chromatography for the synthesis of 2- Ethylhexyl acetate. Sep. Sci. Technol. 2008; 43: 2245–2268.
  • Patidar, P., Mahajani, S. Entrainer-Based Reactive Distillation for the Synthesis of 2-Ethylhexyl Acetate. Ind. Eng. Chem. Res. 2012; 51: 8748-8759.
  • Ali, S. H., Tarakmah, A., Merchant, S. Q., Al-Sahhaf, T. 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. 2007; 62: 3197-3217.
  • Foggler, H. S. Elements of Chemical Reaction Engineering. 3rd ed. New Jersey, USA: Prentice Hall, 1999.
  • Bartholomew, C. H., Farrauto, R. J. Fundamentals of Industrial Catalytic Processes. 2nd ed. USA: John Wiley &Sons, 2006.
  • BASF, Technical leaflet, Petrochemicals: 2-Ethylhexanol, 1999. http://www.solvents.basf.com/portal/load/fid245412/Technical%20Spec%20-%202%20Ethylhexanol_BPC.pdf
  • Teo, H. T. R., Saha, B. Heterogeneous Catalyzed Esterification of Acetic Acid with Isoamyl Alcohol: Kinetic Studies. J. Catal. 2004; 228: 174-182.
  • İzci, A., Bodur, F. Liquid-phase esterification of acetic acid with isobutanol catalyzed by ion-exchange resins. React. Funct. Polym. 2007; 67: 1458-1464.
Year 2017, Volume: 18 Issue: 5, 1098 - 1106, 31.12.2017
https://doi.org/10.18038/aubtda.310676

Abstract

References

  • Kirk, R. E. Othmer, D. F. In Encyclopedia of Chemical Technology, CD-ROM, 4th Ed. New York: John Wiley and Sons, 2001.
  • BASF, Technical Information, Petrochemicals: 2-Ethylhexyl Acetate, 2016. http://www.solvents.basf.com/portal/streamer?fid=278918
  • Solomons, T. W. G. Fundamentals of Organic Chemistry. Canada: John Wiley and Sons, 1982.
  • Altiokka, M. R., Citak, A. Kinetics study of esterification of acetic acid with isobutanol in the presence of amberlite catalyst. Appl. Catal. A: Gen. 2003; 239: 141-148.
  • Blagov, S., Parada, S., Bailer, O., Moritz, P., Lam, D., Weinand, R., Hasse, H. Influence of ion-exchange resin catalysts on side reactions of the esterification of n-butanol with acetic acid. Chem. Eng. Sci. 2006; 61: 753-765.
  • Tsai, Y.-T., Lin, H.-M., Lee, M.-J. Kinetics behavior of esterification of acetic acid with methanol over Amberlyst 36. Chem. Eng. J. 2011; 171: 1367–1372.
  • Richard, R., Guillaume, D., Jacquin, M. Kinetics modeling of the heterogeneously catalyzed esterification of 2,3-Butanediol with acetic acid. Ind. Eng. Chem. Res. 2016; 55: 5247-5256.
  • Leyva, F., Orjuela, A., Miller, D. J., Gil, I., Vargas, J., Rodríguez, G. Kinetics of propionic acid and isoamyl alcohol liquid esterification with Amberlyst 70 as catalyst. Ind. Eng. Chem. Res. 2013; 52: 18153-18161.
  • Ali, S. H., Merchant, S. Q. Kinetics of the esterification of acetic acid with 2-propanol: Impact of different acidic cation exchange resins on reaction mechanism. Int J Chem Kinet 2006; 38: 593– 612.
  • Schmid, B., Dölker, M., Gmehling, J. Esterification of Ethylene Glycol with Acetic Acid Catalyzed by Amberlyst 36. Ind. Eng. Chem. Res. 2008; 47: 698-703.
  • Akbay, E. Ö., Altiokka, M. R. Kinetics of esterification of acetic acid with n-amyl alcohol in the presence of Amberlyst-36. Appl. Catal. A: Gen. 2011; 396: 14–19.
  • Akyalçın, S. Altıokka, M. R. Kinetics of esterification of acetic acid with 1-octanol in the presence of Amberlyst 36. Appl. Catal. A: Gen. 2012; 429-430: 79-84.
  • Schildhauer, T. J., Hoek, I., Kapteijn, F., Moulijn, J. A. Zeolite BEA catalysed esterification of hexanoic acid with 1-octanol: Kinetics, side reactions and the role of water. Appl. Catal. A: Gen. 2009; 358: 141–145.
  • Kirumakki, S. R., Nagaraju, N., Chary, K. V. R. Esterification of alcohols with acetic acid over zeolites Hβ, HY and HZSM5. Appl. Catal. A: Gen. 2006; 299: 185–192.
  • Do Nascimento, L. A. S., Angélica, R. S., Da Costa, C. E. F., Zamian, J. R., Da Rocha Filho, G. N. Comparative study between catalysts for esterification prepared from kaolins. Appl. Clay Sci. 2011; 51: 267–273.
  • Zatta, L., Gardolinski, J. E. F. da C., Wypych, F. Raw halloysite as reusable heterogeneous catalyst for esterification of lauric acid. Appl. Clay Sci. 2011; 51: 165–169.
  • Peters, T. A., Benes, N. E., Holmen, A., Keurentjes, J.T.F. Comparison of commercial solid acid catalysts for the esterification of acetic acid with butanol. Appl. Catal. A: Gen. 2006; 297: 182–188.
  • Liu, W. T., Tan, C. S. Liquid-phase esterification of propionic acid with n-butanol. Ind. Eng. Chem. Res. 2001; 40: 3281 ‒ 3286.
  • Ragaini, V., Bianchi, C.L., Pirola, C. Kinetics of esterification of diluted acetic acid with pure 2-ethyl-1-hexanol. Chemical Eng. J. 2007; 131: 257–262.
  • Rajkumar, T., Ranga Rao, G. Porous hydrous zirconia supported 12-tungstophosphoric acid catalysts for liquid-phase esterification of 2-ethyl-1-hexanol. J. Mol. Catal A: Chem. 2008; 295:1-9.
  • Gyani, V. C., Mahajani, S. Reactive chromatography for the synthesis of 2- Ethylhexyl acetate. Sep. Sci. Technol. 2008; 43: 2245–2268.
  • Patidar, P., Mahajani, S. Entrainer-Based Reactive Distillation for the Synthesis of 2-Ethylhexyl Acetate. Ind. Eng. Chem. Res. 2012; 51: 8748-8759.
  • Ali, S. H., Tarakmah, A., Merchant, S. Q., Al-Sahhaf, T. 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. 2007; 62: 3197-3217.
  • Foggler, H. S. Elements of Chemical Reaction Engineering. 3rd ed. New Jersey, USA: Prentice Hall, 1999.
  • Bartholomew, C. H., Farrauto, R. J. Fundamentals of Industrial Catalytic Processes. 2nd ed. USA: John Wiley &Sons, 2006.
  • BASF, Technical leaflet, Petrochemicals: 2-Ethylhexanol, 1999. http://www.solvents.basf.com/portal/load/fid245412/Technical%20Spec%20-%202%20Ethylhexanol_BPC.pdf
  • Teo, H. T. R., Saha, B. Heterogeneous Catalyzed Esterification of Acetic Acid with Isoamyl Alcohol: Kinetic Studies. J. Catal. 2004; 228: 174-182.
  • İzci, A., Bodur, F. Liquid-phase esterification of acetic acid with isobutanol catalyzed by ion-exchange resins. React. Funct. Polym. 2007; 67: 1458-1464.
There are 28 citations in total.

Details

Subjects Engineering
Journal Section Articles
Authors

Sema Akyalçın

Publication Date December 31, 2017
Published in Issue Year 2017 Volume: 18 Issue: 5

Cite

APA Akyalçın, S. (2017). KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 18(5), 1098-1106. https://doi.org/10.18038/aubtda.310676
AMA Akyalçın S. KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36. AUJST-A. December 2017;18(5):1098-1106. doi:10.18038/aubtda.310676
Chicago Akyalçın, Sema. “KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18, no. 5 (December 2017): 1098-1106. https://doi.org/10.18038/aubtda.310676.
EndNote Akyalçın S (December 1, 2017) KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18 5 1098–1106.
IEEE S. Akyalçın, “KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36”, AUJST-A, vol. 18, no. 5, pp. 1098–1106, 2017, doi: 10.18038/aubtda.310676.
ISNAD Akyalçın, Sema. “KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18/5 (December 2017), 1098-1106. https://doi.org/10.18038/aubtda.310676.
JAMA Akyalçın S. KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36. AUJST-A. 2017;18:1098–1106.
MLA Akyalçın, Sema. “KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 18, no. 5, 2017, pp. 1098-06, doi:10.18038/aubtda.310676.
Vancouver Akyalçın S. KINETICS OF ESTERIFICATION OF ACETIC ACID WITH 2-ETHYLHEXANOL IN THE PRESENCE OF AMBERLYST 36. AUJST-A. 2017;18(5):1098-106.