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Ion Exchange Resins Catalysed Esterification for the Production of Value Added Petrochemicals and Oleochemicals

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Applications of Ion Exchange Materials in Chemical and Food Industries

Abstract

This book chapter is formulated with the aim to review the literature relevant to the esterification reactions catalysed by strong acidic ion exchange resins. Priority has been given to the works that have been published during the last 15 years. Industrially important esterification reactions in the petrochemical and oleochemical industries have been delineated. Various types of strongly acidic ion exchange resins produced by different manufacturers have been used to accelerate the rate of esterification reactions. In the esterification reactions in both petrochemical and oleochemical industries, gel-type resins showed comparable activity with the macro-reticular type resins after swollen by the polar solvents during the reactions, otherwise the macroporous-type resins always performed better. Gel-type resins were also preferred, in particular, for the esterification reactions involved bulky reactant molecules due to the mass transfer restriction of the macro-reticular type resins. In contrast to the comprehensive studies on the activity of ion exchange resin in the esterification reactions, the works that are related to the reusability, recovery and regeneration of these resin catalysts are rather scarce. In order to scale up the esterification processes catalysed by strongly acidic ion exchange resins to the industrial level, future works should be focusing on the solutions to overcome of the aforementioned constraints and limitations.

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References

  1. Abidin SZ, Haigh KF, Saha B (2012) Esterification of free fatty acids in used cooking oil using ion-exchange resins as catalysts: an efficient pretreatment method for biodiesel feedstock. Ind Eng Chem Res 51:14653–14664

    Article  CAS  Google Scholar 

  2. Ahmad MAA, Kamaruzzaman MR, Chin SY (2014) New method for acrylic acid recovery from industrial waste water via esterification with 2-ethyl hexanol. Process Saf Environ Prot 92(6):522–531

    Article  CAS  Google Scholar 

  3. Altıokka MR, Ödeş E (2009) Reaction kinetics of the catalytic esterification of acrylic acid with propylene glycol. Appl Catal A 362(1–2):115–120

    Article  Google Scholar 

  4. Bhandari VM, Sorokhaibam LG, Ranade VV (2016) Ion exchange resin catalysed reactions-an overview. In: Joshi S, Ranade V (eds) Industrial catalytic processes for fine and specialty chemicals. Elsevier, Amsterdam, pp 393–426

    Google Scholar 

  5. Blagov S, Parada S, Bailer O, Moritz P, Lam D, Weinand R, Hasse H (2006) Influence of ion-exchange resin catalysts on side reactions of the esterification of—Butanol with acetic acid. Chem Eng Sci 61(2):753–765

    Article  CAS  Google Scholar 

  6. Boz N, Degimenbasi N, Kalyon DM (2015) Esterification and transesterification of waste cooking oil over amberlyst 15 and modified amberlyst 15 catalysts. Appl Catal B 165:723–730

    Article  CAS  Google Scholar 

  7. Buluklu AD, Sert E, Karakuş S, Atalay FS (2014) Development of kinetic mechanism for the esterification of acrylic acid with hexanol catalyzed by ion-exchange resin. Int J Chem Kinet 46(4):197–205

    Article  CAS  Google Scholar 

  8. Chin SY, Ahmad MAA, Kamaruzaman MR, Cheng CK (2015) Kinetic studies of the esterification of pure and dilute acrylic acid with 2-ethyl hexanol catalysed by Amberlyst 15. Chem Eng Sci 129:116–125

    Article  CAS  Google Scholar 

  9. Constantino DS, Pereira CS, Faria RP, Ferreira AF, Loureiro JM, Rodrigues AE (2015) Synthesis of butyl acrylate in a fixed-bed adsorptive reactor over Amberlyst 15. AIChE J 61:1263–1274

    Article  CAS  Google Scholar 

  10. Đặng T, Chen B (2013) Optimization in esterification of palmitic acid with excess methanol by solid acid catalyst. Fuel Process Technol 109:7–12

    Article  Google Scholar 

  11. Dange PN, Rathod VK (2017) Equilibrium and thermodynamic parameters for heterogeneous esterification of butyric acid with methanol under microwave irradiation. Resour Efficient Technol 3:64–70

    Article  Google Scholar 

  12. Darge O, Thyrion FC (1993) Kinetics of the liquid phase esterification of acrylic acid with butanol catalysed by cation exchange resin. J Chem Technol Biotechnol 58(4):351–355

    Article  CAS  Google Scholar 

  13. de Aguiar VM, de Souza ALF, Galdino FS, da Silva MMC, Teixeira VG, Lachter ER (2017) Sulfonated poly(divinylbenzene) and poly(styrene-divinylbenzene) as catalysts for esterification of fatty acids. Renew Energy 114Part B 725–732

    Google Scholar 

  14. Delgado P, Sanz MT, Beltran S (2007) Kinetic study for esterification of lactic acid with ethanol and hydrolysis of ethyl lactate using an ion-exchange resin catalyst. Chem Eng J 126:111–118

    Article  CAS  Google Scholar 

  15. Feng Y, He B, Cao Y, Li J, Liu M, Yan F, Liang X (2010) Biodiesel production using cation-exchange resin as heterogeneous catalyst. Bioresour Technol 101(5):1518–1521

    Article  CAS  Google Scholar 

  16. Gangadwala J, Mankar S, Mahajani S, Kienle A, Stein E (2003) Esterification of acetic acid with butanol in the presence of ion-exchange resins as catalysts. Ind Eng Chem Res 42:2146–2155

    Article  CAS  Google Scholar 

  17. Hykkerud A, Marchetti JM (2016) Esterification of oleic acid with ethanol in the presence of Amberlyst 15. Biomass Bioenerg 95:340–343

    Article  CAS  Google Scholar 

  18. Ilgen O (2014) Investigation of reaction parameters kinetics and mechanism of oleic acd esterification with methanol by using Amberlyst 46 as a catalyst. Fuel Process Technol 123:134–139

    Article  Google Scholar 

  19. Izci A, Bodur F (2007) Liquid-phase esterification of acetic acid with isobutanol catalyzed by ion-exchange resins. React Funct Polym 67(12):1458–1464

    Article  CAS  Google Scholar 

  20. Jiang Y, Lu J, Sun K, Ma L, Ding J (2013) Esterification of oleic acid with ethanol catalyzed by sulfonated cation exchange resin: experimental and kinetic studies. Energy Convers Manag 76:980–985

    Article  CAS  Google Scholar 

  21. Ju IB, Lim H-W, Jeon W, Suh DJ, Park M-J, Suh Y-W (2011) Kinetic study of catalytic esterification of butyric acid and n-butanol over Dowex 50WX8-400. Chem Eng J 168:293–302

    Article  CAS  Google Scholar 

  22. Kale S, Umbarkar S, Dongare M, Eckelt R, Armbruster U, Martin A (2015) Selective formation of triacetin by glycerol acetylation using acidic ion-exchange resins as catalyst and toluene as entrainer. Appl Catal 490:10–16

    Article  CAS  Google Scholar 

  23. Karakus S, Sert E, Buluklu D, Atalay FS (2014) Liquid phase esterification of acrylic acid with isobutyl alcohol catalyzed by different cation exchange resins. Ind Eng Chem Res 53:4192–4198

    Article  CAS  Google Scholar 

  24. Khan JA, Jamal Y, Shahid A, Boulanger BO (2016) Esterification of acetic acid and oleic acids within the Amberlyst 15 packed catalytic column. Koren J Chem Eng 33:582–586

    Article  Google Scholar 

  25. Komoń T, Niewiadomski P, Oracz P, Jamróz ME (2013) Esterification of acrylic acid with 2-ethylhexan-1-ol: Thermodynamic and kinetic study. Appl Catal A 451:127–136

    Article  Google Scholar 

  26. Kouzu M, Nakagaito A, Hidaka J-S (2011) Pre-esterification of FFA in plant oil tranesterified into biodiesel with the help of solid acid catalysis of sulfonated cation-exchange resin. Appl Catal A 405:36–44

    Article  CAS  Google Scholar 

  27. Kuzminska M, Backov R, Gaigneaux (2015a) Behaviour of cation-exchange resin employed as heterogeneous catalysts for esterification of oleic acid with trimethylolpropane. Appl Catal A Gen 504:11–16

    Article  CAS  Google Scholar 

  28. Kuzminska M, Backov R, Gaigneaux (2015b) Complementarity of heterogeneous and homogeneous catalysis for oleic acid esterification with trimethylolpropane over ion-exchange resins. Catal Commun 59: 222–225

    Article  CAS  Google Scholar 

  29. Liu L, Liu Z, Tang G, Tan W (2014) Esterification of free fatty acids in waste cooking oil by heterogeneous catalyst. Trans Tianjin Univ 20:266–272

    Article  CAS  Google Scholar 

  30. Mariana Reinoso D, Marta Tonetto G (2018) Bioadditives synthesis from selective glycerol esterification over acidic ion exchange resin as catalyst. J. Environ Chem Eng 6:3399–3407

    Article  Google Scholar 

  31. Mulay A, Rathod VK. (2017) Esterification of maleic acid and butanol using cationic exchange resin as catalyst. J Chem Sci 129: 1713–1720

    Article  CAS  Google Scholar 

  32. Orjuela A, Yanez AJ, Santhanakrishnan A, Lira CT, Miller DJ (2012) Kinetics of mixed succinic acid/acetic acid esterification with Amberlyst 70 ion exchange resin as catalyst. Chem Eng J 188:98–107

    Article  CAS  Google Scholar 

  33. Özbay N, Oktar N, Tapan NA (2008) Esterification of free fatty acids in waste cooking oils (WCO): role of ion-exchange resins. Fuel 87(10–11):1789–1798

    Article  Google Scholar 

  34. Pappu VKS, Kanyi V, Santhanakrishnan A, Lira CT, Miller DJ (2013) Butyric acid esterification kinetics over Amberlyst solid acid catalysts: the effect of alcohol carbon chain length. Bioresour Tehnol 130:793–797

    Article  CAS  Google Scholar 

  35. Patel D, Saha B (2012) Esterification of acetic acid with n-hexanol in batch and continuous chromatographic reactors using a gelular ion-exchange resin as a catalyst. Ind Eng Chem Res 51(37):11965–11974

    Article  CAS  Google Scholar 

  36. Qu Y, Peng S, Wang S, Zhang Z, Wang J (2009) Kinetic study of esterification of lactic acid with isobutanol and n-butanol catalysed by ion-exchange resins. Chin J Chem Eng 17:773–780

    Article  CAS  Google Scholar 

  37. Russbueldt BME, Hoelderich WF (2009) New sulfonic acid ion-exchange resins for the preesterification of different oils and fats with high content of free fatty acids. Appl Catal A 362(1–2):47–57

    Article  CAS  Google Scholar 

  38. Saboya RMA, Cecilia JA, García-Sancho C, Sales AV, de Luna FMT, Rodríguez-Castellón E, Cavalcante CL (2017) Synthesis of biolubricants by the esterification of free fatty acids from castor oil with branched alcohols using cationic exchange resins as catalysts. Ind Crops Prod 104:52–61.

    Article  CAS  Google Scholar 

  39. Sert E, Buluklu AD, Karakuş S, Atalay FS (2013) Kinetic study of catalytic esterification of acrylic acid with butanol catalyzed by different ion exchange resins. Chem Eng Process 73:23–28

    Article  CAS  Google Scholar 

  40. Sharma M, Wanchoo RK, Toor AP (2014) Amberlyst 15 catalyzed esterification of nonanoic acid with 1-propanol: kinetics, modeling, and comparison of its reaction kinetics with lower alcohols. Ind Eng Chem Res 53:2167–2174

    Article  CAS  Google Scholar 

  41. Singh N, Kumar R, Sachan PK (2013) Kinetic study of catalytic esterification of butyric acid and ethanol over Amberlyst 15. ISRN Chem Eng 2013:6

    Google Scholar 

  42. Siril PF, Cross HE, Brown DR (2008) New polystyrene sulfonic acid resin catalysts with enhanced acidic and catalytic properties. J Mol Catal A Chem 279(1):63–68

    Article  CAS  Google Scholar 

  43. Sirsam R, Hansora D, Usmani GA (2016) A Mini-Review on solid acid catalysts for esterification reactions. J Inst Eng India Ser E

    Google Scholar 

  44. Son SM, Kimura H, Kasukabe K (2011) Esterification of oleic acid in a three-phase, fixed-bed reactor packed with a cation exchange resin catalyst. Biores Technol 102:2130–2132

    Article  CAS  Google Scholar 

  45. Speight JG (2016) Environmental organic chemistry for engineers. Butterworth-Heinemann

    Google Scholar 

  46. Van de Steena E, De Clereq J, Thybaut JW (2014) Ion exchange resin catalysed transesterification of ethyl acetate with methanol: gel versus macroporous resins. Chem Eng J 242:170–179

    Article  Google Scholar 

  47. Toor AP, Sharma M, Thakur S, Wanchoo RK (2011) Ion-exchange resin catalyzed esterification of lactic acid with isopropanol: a kinetic study. Bull. Chem. React Eng Catal 39–45

    Google Scholar 

  48. Willing A (1999) Oleochemical esters—environmentally compatible raw materials for oils and lubricants from renewable resources. Fett/Lipid 101:192–198

    Article  CAS  Google Scholar 

  49. Yin P, Chen L, Wang Z, Qu R, Liu X, Xu Q, Ren S (2012) Biodiesel production from esterification of oleic acid over aminophosphonic acid resin D418. Fuel 102:499–505

    Article  CAS  Google Scholar 

  50. Yunus NBM, Roslan NAB, Chin SY, Abidin SZ (2016) Esterification of free fatty acid in used cooking oil using gelular exchange resin as catalysts. Procedia Engineering 148:1274–1281

    Article  Google Scholar 

  51. Zhou L, Al-Zaini E, Adesina A (2013) Catalytic characteristics and parameters optimization of the glycerol acetylation over solid acid catalysts. Fuel 103:617–625

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Faculty of Chemical and Natural Resources Engineering, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300, Gambang, Kuantan, Pahang, Malaysia

    Sim Yee Chin, Nurwadiah Azizan, Mohd Amirul Asyraf Ahmad & Muhammad Ridzuan Kamaruzaman

  2. Centre of Excellence for Advance Research in Fluid Flow, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300, Gambang, Kuantan, Pahang, Malaysia

    Sim Yee Chin

Authors
  1. Sim Yee Chin
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  2. Nurwadiah Azizan
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  3. Mohd Amirul Asyraf Ahmad
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  4. Muhammad Ridzuan Kamaruzaman
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Corresponding author

Correspondence to Sim Yee Chin .

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Editors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia

    Inamuddin

  2. Department of Chemistry, National Institute of Technology Srinagar, Srinagar, India

    Tauseef Ahmad Rangreez

  3. Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia

    Abdullah M. Asiri

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Chin, S.Y., Azizan, N., Ahmad, M.A.A., Kamaruzaman, M.R. (2019). Ion Exchange Resins Catalysed Esterification for the Production of Value Added Petrochemicals and Oleochemicals. In: Inamuddin, Rangreez, T., M. Asiri, A. (eds) Applications of Ion Exchange Materials in Chemical and Food Industries. Springer, Cham. https://doi.org/10.1007/978-3-030-06085-5_4

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