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Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100

Year 2016, Volume: 17 Issue: 1, 25 - 36, 25.04.2016
https://doi.org/10.18038/btda.18655

Abstract

The kinetics of esterification of salicylic acid with amyl alcohol has been studied batchwise in the presence of Lewatit MonoPlus S-100 as heterogeneous catalyst. The kinetic behavior of the reaction has been tested by three different models: the quasi-homogeneous model, the Eley–Rideal model and the Langmuir–Hinselwood model. L-H model fits the experimental data best among the others.

Keywords: Esterification, Salicylic Acid, n-Amyl Alcohol, Kinetic modeling, Lewatit MonoPlus S-100

 

References

  • G.D. Yadav, P.H. Mehta, Ind. Eng. Chem. Res. 33 (1994), Heterogeneous Catalysis in Esterication Reactions: Preparation of Acetate and Cyclohexyl Acetate by Using a Variety of Solid Acidic Catalysts 2198–2208.
  • J. Lilja, J. Aumo, T. Salmi, D. Murzin, P. Maki-Arvela, M. Sundell, K. Ekman, R. Peltonen, H. Vainio, Hydrogenation of citral over a polymer fibre catalyst, Appl. Catal. A: Gen. 228 (2002) 253– 267.
  • C.E. Leyes, D.F. Othmer, Esterification of Butanol and Acetic Acid, Industrial and Engineering Chemistry 37 (10) (1945) 968-975.
  • M.R. Altıokka, A. Cıtak, Appl. Catal. A: Gen. 239 (2003), Kinetics Study of Esterification of Acetic Acid With Isobutanol in The Presence of Amberlite Catalyst, 141–148.
  • M.R. Altıokka, H.L. Hosgün, Ind. Eng. Chem. Res. 46 (2007), Kinetics of Hydrolysis of Benzaldehyde Dimethyl Acetal over Amberlite IR-120, 1058–1062.
  • Tanabe, Misono, Ono, Hattori, New Solid Acid and Bases, Kodan-sha/Elsevier Science, Tokyo/Amsterdam, 1989.
  • A.E.R.S. Khder, Appl. Catal. A: Gen. 343 (1–2) (2008), Preparation, characterization and catalytic activity of tin oxide-supported 12- tungstophosphoric acid as a solid catalyst, 109–116.
  • A. Charkrabati, M.M. Sharma, React. Polym. 20 (1993), Cationic ion exchange resins as catalyst, 1–45. [9] M.M. Sharma, React. Funct. Polym. 26 (1995), Some novel aspects of cationic ion-exchange resins as catalysts, 3–23.
  • S.B. Valdeilson, C.L. Ivoneide, F.A.C. Garcia, S.C.L. Dias, J.A. Dias, Catal. Today 133–135 (2008), Kinetics of esterification of acetic acid with n-amyl alcohol in the presence of Amberlyst-36, 106–112.
  • T.L. Marker, G.A. Funck, T. Barger, U. Hammershaimb, US Patent, Esterification of acetic acid by isoamylic alcohol over catalytic membranes of poly(vinyl alcohol) containing sulfonic acid groups, 5504258 (1996).
  • D.E. Hendriksen, J.R. Lattner, M.J.G. Janssen, US Patent, Alkylation process using zeolite beta, 6002057 (1999).
  • R. Chitnis, M.M. Sharma, React. Funct. Polym. 32 (1997), Industrial applications of acid-treated clays as catalysts, 93–115.
  • J.T. Kloprogge, J. Porous Mater. 5 (1998), Synthetics of smectites and porous pillared clay catalysts, 5–41.
  • C.S.M. Pereira, S.P. Pinho, V.M.T.M. Silva, A.E. Rodrigues, Ind. Eng. Chem. Res. 47 (2008), Multifunctional Reactor for the Synthesis of Dimethylacetal, 1453–1463.
  • V.T.M.M. Silva, A.E. Rodrigues, Chem. Eng. Sci. 61 (2006), Kinetic study of transesterification of methyl acetate with n-butanol catalyzed by NKC-9, 316–331.
  • Y. Fuchigami, J. Chem. Eng. Jpn. 23 (1990), Hydrolysis of Methyl Acetate in Distillation Column, 354–358.
  • Z.P. Xu, K.T. Chuang, Chem. Eng. Sci. 52 (17) (1997), inetic of Acetic Acid Esterication Over Ion Exchange Catalysts 3011–3017.
  • J. Gangadwala, S.Mankar, S.M.Mahajani, A. Kienle, E. Stein, Ind. Eng. Chem. Res. 42 (2003), Esterification of acetic acid with butanol in the presence of ion-exchange resins as catalysts 2146– 2155. [20] B. Erdem, M. Cebe, Korean J. Chem. Eng. 23 (6) (2006), Kinetics of Esterification of Propionic Acid with n-amyl Alcohol in the Presence of Cation Exchange Resin, 896–901.
  • M.T. Sanz, R. Murga, S. Beltran, J.L. Cabezas, Ind. Eng. Chem. Res. 41 (2002) 512–517.
  • M.R. Altıokka, E. Ödes¸ Appl. Catal. A: Gen. 362 (2009), Reaction kinetics of the catalytic esterification of acrylic acid with propylene glycol, 115–120.
  • W.T. Liu, C.S. Tan, Ind. Eng. Chem. Res. 40 (2001), eactive-extraction of 2,3-butanediol from Fermentation Broth by Propionaldehyde: Equilibrium and Kinetic Study, 3281–3286.
  • S.R. Kirumakki, N Nagaraju, K.V.V.S.B.S.R Murthy, S. Narayanan, Appl. Catal. A: Gen. 226 (1– 2) (2002), Esterification of salicylic acid over zeolites using dimethyl carbonate, 175–182.
  • H. Shi, W. Zhu, H. Li, H. Liu, M. Zhang, Y. Yan, Z. Wang, Catal. Comm. 11 (7) (2010), Syntheses of novel halogen-free Brİnsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate, 588–591.
  • F.F. Bamoharrama, M.M. Heravib, M. Roshania, M. Jahangira, A. Ghariba, Appl. Catal. A: Gen. 302 (1) (2006), H14[NaP5W30O110]: A heteropoly acid catalyzed acetylation of alcohols and phenols in acetic anhydride, 42–47.
  • F.F. Bamoharram, M.M. Heravi, J. Ebrahimi, A. Ahmadpour, M. Zebarjad, Chin. J. Catal. 32 (5) (2011), Synthesis of Ibuprofen Using Silica-Supported Preyssler Nanoparticles as an Eco-Friendly, Inexpensive, and Efficient Catalyst, 782–788.
  • Y. Zhenga, X. Su, X. Zhang, W. Wei, Y. Sun, Stud. Surf. Sci. Catal. 156 (2005), Enhanced magneto-optical response in dumbbell like Ag-CoFe2O4 nanoparticle pairs, 205–212.
  • H.S. Fogler, Elements of Chemical Reaction Engineering, third ed., Prentice Hall, New Jersey, 1999. [31] M.J. Lee, J.Y. Chiu, H.M. Lin, Ind. Eng. Chem. Res. 41 (2002), Kinetics of Catalytic Esterification of Propionic Acid and n-Butanol over Amberlyst 35, 2882–2887.
  • H.T.R. Teo, B. Saha, J. Catal. 228 (2004), Heterogeneous catalysed esterification of acetic acid
  • with isoamyl alcohol: kinetic studies, 174–182.
  • M.J. Lee, H.T. Wu, H.M. Lin, Ind. Eng. Chem. Res. 39 (2000), Kinetics of Catalytic Esterification of Acetic Acid and Amyl Alcohol over Dowex, Ind. Eng. Chem. Res., 4094–4099.
  • M.J. Lee, H.T. Wu, C.H. Kang, H.M. Lin, J. Chin. Inst. Chem. Eng. 30 (2) (1999), Kinetic Behavior of Amyl Acetate Synthesis Catalyzed by Acidic Cation Exchange Resin, 117–122.
  • A. Palani, A. Pandurangan, J. Mol. Catal. A: Chem. 226 (2005), Esterification of acetic acid over mesoporous Al-MCM-41 molecular sieves, 129–134.
  • P. Delgado, M.T. Sanz, S. Beltran, Chem. Eng. J. 126 (2007), Kinetic study for esterification of lactic acid with ethanol and hydrolysis of ethylactate, 111–118.
  • V.J. Cruz, J.F. Izquierdo, F. Cunill, J. Tejero, M. Iborra, C. Fite, R. Bringue, React. Funct. Polym. 67 (3) (2007), Etherification of tert-Amyl Alcohol with Methanol over Ion-Exchange Resin, 210–224. [37] M.P. Titus, M. Bausach, J. Tejero, M. Iborra, C. Fite, F. Cunill, J.F. Izquierdo, Appl. Catal. A: Gen. 323 (2007), Liquid-phase synthesis of isopropyl tert-butyl ether by addition of 2-propanol to isobutene on the oversulfonated ion-exchange resin Amberlyst-35, 38–50.
  • H.T.R. Teo, B. Saha, J. of Catalysis 228 (2004), Heterogeneous catalysed esterification of acetic acid with isoamyl alcohol: kinetic studies, 174–182.

KINETICS OF ESTERIFICATION OF SALICYLIC ACID WITH N-AMYL ALCOHOL IN THE PRESENCE OF LEWATIT MONOPLUS S-100

Year 2016, Volume: 17 Issue: 1, 25 - 36, 25.04.2016
https://doi.org/10.18038/btda.18655

Abstract

Amil alkol ile salisilik asidin esterifikasyon kinetiği heterojen bir katalizör olan Lewatit MonoPlus S-100 varlığında kesikli bir sistemde incelenmiştir. Reaksiyon kinetik davranışı, üç farklı modelde tarafından test edilmiştir: yarı-homojen bir model, Eley-Rideal modeli ve Langmuir-Hinselwood modeli. Bütün modeller arasında en iyi deneysel verileri L-H modelinin sağladığı bulunmuştur

References

  • G.D. Yadav, P.H. Mehta, Ind. Eng. Chem. Res. 33 (1994), Heterogeneous Catalysis in Esterication Reactions: Preparation of Acetate and Cyclohexyl Acetate by Using a Variety of Solid Acidic Catalysts 2198–2208.
  • J. Lilja, J. Aumo, T. Salmi, D. Murzin, P. Maki-Arvela, M. Sundell, K. Ekman, R. Peltonen, H. Vainio, Hydrogenation of citral over a polymer fibre catalyst, Appl. Catal. A: Gen. 228 (2002) 253– 267.
  • C.E. Leyes, D.F. Othmer, Esterification of Butanol and Acetic Acid, Industrial and Engineering Chemistry 37 (10) (1945) 968-975.
  • M.R. Altıokka, A. Cıtak, Appl. Catal. A: Gen. 239 (2003), Kinetics Study of Esterification of Acetic Acid With Isobutanol in The Presence of Amberlite Catalyst, 141–148.
  • M.R. Altıokka, H.L. Hosgün, Ind. Eng. Chem. Res. 46 (2007), Kinetics of Hydrolysis of Benzaldehyde Dimethyl Acetal over Amberlite IR-120, 1058–1062.
  • Tanabe, Misono, Ono, Hattori, New Solid Acid and Bases, Kodan-sha/Elsevier Science, Tokyo/Amsterdam, 1989.
  • A.E.R.S. Khder, Appl. Catal. A: Gen. 343 (1–2) (2008), Preparation, characterization and catalytic activity of tin oxide-supported 12- tungstophosphoric acid as a solid catalyst, 109–116.
  • A. Charkrabati, M.M. Sharma, React. Polym. 20 (1993), Cationic ion exchange resins as catalyst, 1–45. [9] M.M. Sharma, React. Funct. Polym. 26 (1995), Some novel aspects of cationic ion-exchange resins as catalysts, 3–23.
  • S.B. Valdeilson, C.L. Ivoneide, F.A.C. Garcia, S.C.L. Dias, J.A. Dias, Catal. Today 133–135 (2008), Kinetics of esterification of acetic acid with n-amyl alcohol in the presence of Amberlyst-36, 106–112.
  • T.L. Marker, G.A. Funck, T. Barger, U. Hammershaimb, US Patent, Esterification of acetic acid by isoamylic alcohol over catalytic membranes of poly(vinyl alcohol) containing sulfonic acid groups, 5504258 (1996).
  • D.E. Hendriksen, J.R. Lattner, M.J.G. Janssen, US Patent, Alkylation process using zeolite beta, 6002057 (1999).
  • R. Chitnis, M.M. Sharma, React. Funct. Polym. 32 (1997), Industrial applications of acid-treated clays as catalysts, 93–115.
  • J.T. Kloprogge, J. Porous Mater. 5 (1998), Synthetics of smectites and porous pillared clay catalysts, 5–41.
  • C.S.M. Pereira, S.P. Pinho, V.M.T.M. Silva, A.E. Rodrigues, Ind. Eng. Chem. Res. 47 (2008), Multifunctional Reactor for the Synthesis of Dimethylacetal, 1453–1463.
  • V.T.M.M. Silva, A.E. Rodrigues, Chem. Eng. Sci. 61 (2006), Kinetic study of transesterification of methyl acetate with n-butanol catalyzed by NKC-9, 316–331.
  • Y. Fuchigami, J. Chem. Eng. Jpn. 23 (1990), Hydrolysis of Methyl Acetate in Distillation Column, 354–358.
  • Z.P. Xu, K.T. Chuang, Chem. Eng. Sci. 52 (17) (1997), inetic of Acetic Acid Esterication Over Ion Exchange Catalysts 3011–3017.
  • J. Gangadwala, S.Mankar, S.M.Mahajani, A. Kienle, E. Stein, Ind. Eng. Chem. Res. 42 (2003), Esterification of acetic acid with butanol in the presence of ion-exchange resins as catalysts 2146– 2155. [20] B. Erdem, M. Cebe, Korean J. Chem. Eng. 23 (6) (2006), Kinetics of Esterification of Propionic Acid with n-amyl Alcohol in the Presence of Cation Exchange Resin, 896–901.
  • M.T. Sanz, R. Murga, S. Beltran, J.L. Cabezas, Ind. Eng. Chem. Res. 41 (2002) 512–517.
  • M.R. Altıokka, E. Ödes¸ Appl. Catal. A: Gen. 362 (2009), Reaction kinetics of the catalytic esterification of acrylic acid with propylene glycol, 115–120.
  • W.T. Liu, C.S. Tan, Ind. Eng. Chem. Res. 40 (2001), eactive-extraction of 2,3-butanediol from Fermentation Broth by Propionaldehyde: Equilibrium and Kinetic Study, 3281–3286.
  • S.R. Kirumakki, N Nagaraju, K.V.V.S.B.S.R Murthy, S. Narayanan, Appl. Catal. A: Gen. 226 (1– 2) (2002), Esterification of salicylic acid over zeolites using dimethyl carbonate, 175–182.
  • H. Shi, W. Zhu, H. Li, H. Liu, M. Zhang, Y. Yan, Z. Wang, Catal. Comm. 11 (7) (2010), Syntheses of novel halogen-free Brİnsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate, 588–591.
  • F.F. Bamoharrama, M.M. Heravib, M. Roshania, M. Jahangira, A. Ghariba, Appl. Catal. A: Gen. 302 (1) (2006), H14[NaP5W30O110]: A heteropoly acid catalyzed acetylation of alcohols and phenols in acetic anhydride, 42–47.
  • F.F. Bamoharram, M.M. Heravi, J. Ebrahimi, A. Ahmadpour, M. Zebarjad, Chin. J. Catal. 32 (5) (2011), Synthesis of Ibuprofen Using Silica-Supported Preyssler Nanoparticles as an Eco-Friendly, Inexpensive, and Efficient Catalyst, 782–788.
  • Y. Zhenga, X. Su, X. Zhang, W. Wei, Y. Sun, Stud. Surf. Sci. Catal. 156 (2005), Enhanced magneto-optical response in dumbbell like Ag-CoFe2O4 nanoparticle pairs, 205–212.
  • H.S. Fogler, Elements of Chemical Reaction Engineering, third ed., Prentice Hall, New Jersey, 1999. [31] M.J. Lee, J.Y. Chiu, H.M. Lin, Ind. Eng. Chem. Res. 41 (2002), Kinetics of Catalytic Esterification of Propionic Acid and n-Butanol over Amberlyst 35, 2882–2887.
  • H.T.R. Teo, B. Saha, J. Catal. 228 (2004), Heterogeneous catalysed esterification of acetic acid
  • with isoamyl alcohol: kinetic studies, 174–182.
  • M.J. Lee, H.T. Wu, H.M. Lin, Ind. Eng. Chem. Res. 39 (2000), Kinetics of Catalytic Esterification of Acetic Acid and Amyl Alcohol over Dowex, Ind. Eng. Chem. Res., 4094–4099.
  • M.J. Lee, H.T. Wu, C.H. Kang, H.M. Lin, J. Chin. Inst. Chem. Eng. 30 (2) (1999), Kinetic Behavior of Amyl Acetate Synthesis Catalyzed by Acidic Cation Exchange Resin, 117–122.
  • A. Palani, A. Pandurangan, J. Mol. Catal. A: Chem. 226 (2005), Esterification of acetic acid over mesoporous Al-MCM-41 molecular sieves, 129–134.
  • P. Delgado, M.T. Sanz, S. Beltran, Chem. Eng. J. 126 (2007), Kinetic study for esterification of lactic acid with ethanol and hydrolysis of ethylactate, 111–118.
  • V.J. Cruz, J.F. Izquierdo, F. Cunill, J. Tejero, M. Iborra, C. Fite, R. Bringue, React. Funct. Polym. 67 (3) (2007), Etherification of tert-Amyl Alcohol with Methanol over Ion-Exchange Resin, 210–224. [37] M.P. Titus, M. Bausach, J. Tejero, M. Iborra, C. Fite, F. Cunill, J.F. Izquierdo, Appl. Catal. A: Gen. 323 (2007), Liquid-phase synthesis of isopropyl tert-butyl ether by addition of 2-propanol to isobutene on the oversulfonated ion-exchange resin Amberlyst-35, 38–50.
  • H.T.R. Teo, B. Saha, J. of Catalysis 228 (2004), Heterogeneous catalysed esterification of acetic acid with isoamyl alcohol: kinetic studies, 174–182.
There are 35 citations in total.

Details

Journal Section Articles
Authors

Elif Akbay

Ilay Aytek This is me

Publication Date April 25, 2016
Published in Issue Year 2016 Volume: 17 Issue: 1

Cite

APA Akbay, E., & Aytek, I. (2016). Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(1), 25-36. https://doi.org/10.18038/btda.18655
AMA Akbay E, Aytek I. Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100. AUJST-A. June 2016;17(1):25-36. doi:10.18038/btda.18655
Chicago Akbay, Elif, and Ilay Aytek. “Kinetics of Esterification of Salicylic Acid With N-Amyl Alcohol in the Presence of Lewatit MonoPlus S-100”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17, no. 1 (June 2016): 25-36. https://doi.org/10.18038/btda.18655.
EndNote Akbay E, Aytek I (June 1, 2016) Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17 1 25–36.
IEEE E. Akbay and I. Aytek, “Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100”, AUJST-A, vol. 17, no. 1, pp. 25–36, 2016, doi: 10.18038/btda.18655.
ISNAD Akbay, Elif - Aytek, Ilay. “Kinetics of Esterification of Salicylic Acid With N-Amyl Alcohol in the Presence of Lewatit MonoPlus S-100”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17/1 (June 2016), 25-36. https://doi.org/10.18038/btda.18655.
JAMA Akbay E, Aytek I. Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100. AUJST-A. 2016;17:25–36.
MLA Akbay, Elif and Ilay Aytek. “Kinetics of Esterification of Salicylic Acid With N-Amyl Alcohol in the Presence of Lewatit MonoPlus S-100”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 17, no. 1, 2016, pp. 25-36, doi:10.18038/btda.18655.
Vancouver Akbay E, Aytek I. Kinetics of esterification of salicylic acid with n-amyl alcohol in the presence of Lewatit MonoPlus S-100. AUJST-A. 2016;17(1):25-36.