Kinetic investigations on esterification of maleic anhydride with butanols

• Autorzy: Bartoszewicz Maria , Kulawska Maria , Organek Wiesław

Identyfikatory

DOI

10.24425/cpe.2020.136014

• Języki publikacji: EN

Abstrakty

EN

Kinetic studies of esterification reaction of maleic anhydride with butan-1-ol, 2-methylpropan-1-ol and butan-2-ol were carried out in a semibatch reactor, in the presence of four acidic catalysts: sulfuric acid, phosphotungstic acid, ion exchange resin Dowex 50WX8 and tetrabutyl zirconate. Phosphotungstic acid proved to be the most active catalyst. The temperature range was 383–413 K, the initial molar ratio of alcohol to acid ranged 2.2-5:1. The kinetic parameters were given. The kinetics appeared to be that of the second order with respect both to the acid and to the alcohol. The reaction carried out in the presence of tetrabutyl zirconate was very slow and depended only on acid concentration. The effect of temperature on the reaction rate follows the Arrhenius equation well.

Słowa kluczowe

EN

acidic catalysts; butyl alcohol; dibutyl maleate; esterification reaction; plasticizer

PL

katalizator kwasowy; alkohol butylowy; reakcja estryfikacji; plastyfikator

• Wydawca: Komitet Inżynierii Chemicznej i Procesowej Polskiej Akademii Nauk
• Czasopismo: Chemical and Process Engineering
• Rocznik: 2020
• Tom: Vol. 41, nr 4
• Strony: 293–--306
• Opis fizyczny: Bibliogr. 38 poz., wykr., tab.

Twórcy

autor

Bartoszewicz Maria

• Łukasiewicz Research Network – Institute of Heavy Organic Synthesis “Blachownia”, Energetyków 9, 47-225 Kędzierzyn-Koźle, Poland

autor

Kulawska Maria

• Polish Academy of Sciences, Institute of Chemical Engineering, Bałtycka 5, 44-100 Gliwice, Poland

autor

Organek Wiesław

• Polish Academy of Sciences, Institute of Chemical Engineering, Bałtycka 5, 44-100 Gliwice, Poland

Bibliografia

• 1. Ali S.H, Tarakmah A., Merchant S.Q., Al-Sahhaf T., 2007. Synthesis of esters: development of the rate expression for the Dowex 50WX8-400 catalysed esterification of propionic acid with 1-propanol. Chem. Eng. Sc., 62, 3197– 3217. DOI: 10.1016/j.ces.2007.03.017.
• 2. Ali S.H., Merchant S.Q., 2009. Kinetic study of Dowex 50WX8 – catalysed esterification and hydrolysis of benzyl acetate. Ind. Eng. Chem. Res., 48, 2519–2532. DOI: 10.1021/ie8006787.
• 3. Alsalme A., Kozhevnikova E., Kozhevnikov I., 2008. Heteropoly acids as catalysts for liquid-phase esterification and transesterification. Appl. Catal, 349, 170–176. DOI: 10.1016/j.apcata.2008.07.027.
• 4. Alvarez J., Alvarez J.J., 1988. Kinetics for preparation of diethyl maleate from maleic anhydride and ethanol catalyzed by sulphuric acid. J. Ind. Chem., 16, 263–271.
• 5. Burghardt A., Bartelmus G., 2001. Inżynieria Reaktorow Chemicznych. Tom 1, Wydawnictwo Naukowe PWN, Warszawa.
• 6. Dharwadkar A., Hussain Z., 1977. Kinetics of and semibatch reactor design for the preparation of dibutyl maleate. Indian. J. Technol., 15, 156–159.
• 7. Dupont P., Lefebre F., 1996. Esterification of propionic acid by butanol and 2-ethylhexylanol catalyzed by het- eropolyacids pure or supported. J. Mol. Catal. A: Chem., 114, 299–307. DOI: 10.1016/S1381-1169(96)00329-9.
• 8. DuPont.Tyzor, 2001. Organic Titanates. Product Information–Tyzor®TNTB.
• 9. Esfandmaz S., Chaibakhsh N., Moradi-Shoeili Z., Mohammadi A., 2018. Eco-friendly synthesis of maleate ester: A comparison between solid acid and enzyme-catalyzed esterification. Sustainable Chem. Pharm., 8, 82–88. DOI: 10.1016/j.scp.2018.03.003.
• 10. Fischer R., Kaibel G., Pinkos R., Rahn R., 2000. Method for producing mixtures of 1,4-butanediol, tetrahydrofuran and -butyrolactone. US6350924B1.
• 11. Fischer R., Kaibel G., Pinkos R., Rahn R., 2002. Method for producing mixtures of 1,4-butanediol, tetrahydrofuranu and -butyrolactone. US6433192B1.
• 12. Grzesik M., Skrzypek J., Gumuła T., 2000. The effect of the catalyst used on the kinetics of di-2-ethylhexyl maleate synthesis. React. Kinet. Catal. Lett., 71, 13–18. DOI: 10.1023/A:1010397108805.
• 13. Grzesik M., Skrzypek J., Lachowska M., 2003. Kinetics of esterification of maleic anhydride with hexan-1-ol using selected catalysts. Chem.Pap., 57(6), 421–423.
• 14. Grzesik M., J. Skrzypek J., Tuszyński T., 1999. Estryfikacja bezwodnika maleinowego alkoholem 2- etyloheksy-lowym w warunkach niekatalitycznych i katalizowanych kwasem siarkowym. Inż. Chem. i Proc., 20, 351–362.
• 15. Induri S., Sengupta S., Basu J.K., 2010. A kinetic approach to the esterification of maleic anhydride with metanol on H-Y zeolite. J. Ind. Eng. Chem., 16, 467–473. DOI: . DOI: 10.1016/j.jiec.2010.01.053.
• 16. Iovel G., Lukevics E., 1998. Hydroxymethylation and alkylation of compounds of the furan, thiophene, and pyrrole in the presence of H+ cations (review). Chem. Heterocycl. Compd., 34, 1–12. DOI: 10.1007/BF02290607.
• 17. Johnson Mattey Catalysts, 2003. Vertec – Direct Esterification Technology, www.matthey.com.
• 18. Ju I.B., Lim H-W.,Wonjin J., Suh D.J., Park M.J., Suh Y.W., 2011. Kinetic study of catalytic esterification of butyric
• 19. acid and n-butanol over Dowex 50WX8-400. Chem. Eng. J., 168, 293–302. DOI: 10.1016/j.cej.2010.12.086.
• 20. Liu Z-T.,Wu J., Liu L., Sun Ch., Song L., Gao Z., DongW., Lu J., 2006a. Solubilities of AOT analogues surfactants in supercritical CO2 and HFC-134a fluids. J. Chem. Eng. Data, 51, 1761–1768, 2006. DOI: 10.1021/je0601659.
• 21. Liu Z-T. Liu L., Wu J.,Song L., Gao Z., Dong W., Lu J., 2006b. Solubility and phase behaviors of AOT analogue surfactants in 1,1,1,2-tetrafluoroethane and supercritical carbon dioxide. J. Chem. Eng. Data, 51, 2045–2050. DOI: 10.1021/je060152v.
• 22. Kozhevnikov I., 1987. Advances in catalysis by heteropolyacid. Russ. Chem. Rev, 56, 811–825. DOI: 10.1070/RC1987v056n09ABEH003304.
• 23. Kozhevnikov I., 1998. Catalysis by heteropoly acids and multicomponent liquid-phase reactions. Chem. Rev., 98, 171–198. DOI: 10.1021/cr960400y.
• 24. Kulawska M., Sadłowski J.Z., Skrzypek J., 2005. Kinetics of the esterification of maleic anhydride with octyl, decyl, or dodecyl alcohol over dowex catalyst. React. Kinet. Catal. Lett., 85, 51–56. DOI: 10.1007/s11144-005-0242-1.
• 25. Kulawska M., Sadłowski J.Z., Skrzypek J., Moroz H., 2005. Kinetyka estryfikacji bezwodnika maleinowego alkoholem n-oktylowym katalizowanej żywic˛a jonowymienn˛a. Inż. Chem. i Proc., 26, 631–635.
• 26. March J., 1992. Advanced organic chemistry. Reactions, mechanism and structure. 4th edition, JohnWiley & Sons, New York.
• 27. Morrison R., Boyd R., 1985. Chemia organiczna. PWN, Warszawa, 1985.
• 28. Mulay A., Rathod V.K., 2017. Esterification of maleic acid and butanol using cationic exchange resin as catalyst. J. Chem. Sci., 129, 1713–1720. DOI: 10.1007/s12039-017-1375-2.
• 29. Nagasoe Y., Ichiyanagi N., Okabayashi H., Nave S., Eastoe J., O’Connor C., 1999. Raman and IR spectroscopic studies of the interaction between counterion and polar group in self-assembled systems of AOT-homologous sodium dialkyl sulfosuccinates. Phys. Chem., 4395–4408. DOI: 10.1039/A904815D.
• 30. Okabayashi O., Sumiya A., Izawa K-I., Eastoe J., O’Connor C., 2010. Role of the succinate skeleton in the disorder-order transition of AOT and its analogous molecules: Detection by infrared absorption spectra of the configurations arising from the difference in torsion angles of the succinate. Bull. Chem. Soc. Jap., 83, 651–659. DOI: 10.1246/bcsj.20100002.
• 31. Reddy R., Iyengar P., Nagendrappa G., Prahash J., 2005. Esterification of dicarboxylic acids to diesters over Mn+-montmorillonite clay catalysts. Catal. Lett., 101, 87–91. DOI: 10.1007/s10562-004-3754-9.
• 32. Sepulveda J., Yori J., Vera C., 2005. Repeated use of supported H3PW12O40 catalysts in the liquid phase esterification of acetic acid with butanol. Appl. Catal. A, 288, 18–24. DOI: 10.1016/j.apcata.2005.03.038.
• 33. Shanmungam T.K., Viswanathan B., Varadarajan B., 2004. Esterification by solid acid catalysts – a comparison. J. Mol. Catal. A: Chem., 223, 143–147. DOI: 10.1016/j.molcata.2004.02.030.
• 34. Taysun M. B., Sert E., Atalay F.S., 2014. Esterification of maleic acid with butanol catalysed by environmentally friendly catalysts. ISITES 2014, 2nd International Symposium on Innovative Technologies in Engineering and Science, June 18–20, Karabuk, Turkey, 1325–1332.
• 35. The Dow Chemical Company, 2002. Dowex ion exchange resins – suggested operating temperature for Dowex ion exchange resins.
• 36. Timofeev A.F., Sushchenko L.F., Tereshchenko G.F., Golubkov I.M, 1985. J. Appl. Chem. USSR, 58(7), 1534–1537.
• 37. Tuck M., Wood M., Hiles A., 2000. Process for the production of 1,4-butanediol. US6100410.
• 38. Yadav G., Thathgar M., 2002. Esterification of maleic acid with ethanol over cation-exchange resin catalysts. React. Func. Polym, 52, 99–100. DOI: 10.1016/S1381-5148(02)00086-X.