Reusable and Efficient Polystryrene-Supported Acidic Ionic Liquid Catalyst for the Synthesis of n-Butyl Acetate

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A series of polystyrene-supported 1-(propyl-3-sulfonate)-3-methy-imidazolium hydrosulfate acidic ionic liquid (PS-[SO3H-PMIM][HSO4]) catalysts with different [SO3H-PMIM][HSO4] contents were prepared and tested for esterification of n-butyl alcohol with acetic acid. It was found that the reactivity of the catalyst increased with increasing [SO3H-PMIM][HSO4] content, and best yield of n-Butyl acetate of 98% was obtained using PS-[SO3H-PMIM][HSO4]1 within 1.5h. The catalytic activity of this catalyst decreased slightly after fifth using.

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20-25

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June 2014

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© 2014 Trans Tech Publications Ltd. All Rights Reserved

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[1] S. Kaewta, L. Edgar, G.G. James, Solid bronsted acid catalysis in the gas-phase esterification of acetic acid, Ind. Eng. Chem. Res. 46 (2007) 7050–7056.

DOI: 10.1021/ie070536u

Google Scholar

[2] X.Z. Li, W.J. Eli, A green approach for the synthesis of long chain aliphatic acid esters at room temperature, J. Mol. Catal. A: Chem. 279 (2008) 159–164.

DOI: 10.1016/j.molcata.2007.08.032

Google Scholar

[3] V.R. Vamsi, V.R. Modukuri, A. Ratnamala, et. al. A Simple, Efficient, Green, Cost Effective and Chemoselective Process for the Esterification of Carboxylic Acids, Org. Process Res. Dev. 13 (2009) 769-773.

DOI: 10.1021/op900096y

Google Scholar

[4] J.F. Dubreuil, K. Bourahla, M. Rahmouni, et. al. Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media, Catal. Commun. 3 (2002) 185-190.

DOI: 10.1016/s1566-7367(02)00087-0

Google Scholar

[5] T. Joseph, S. Sahoo, S.B. Halligudi, Brönsted acidic ionic liquids: A green, efficient and reusable catalyst system and reaction medium for Fischer esterification, J. Mol. Catal. A: Chem. 234 (2005) 107-110.

DOI: 10.1016/j.molcata.2005.03.005

Google Scholar

[6] P.M. Christian, A.C. Raymond, C.D. Nicholas, et. al. Supported Ionic Liquid Catalysis − A New Concept for Homogeneous Hydroformylation Catalysis, J. Am. Chem. Soc. 124 (2002) 12932-12933.

DOI: 10.1021/ja0279242

Google Scholar

[7] C. DeCastro, E. Sauvage, M.H. Valkenberg, et. al. Immobilised Ionic Liquids as Lewis Acid Catalysts for the Alkylation of Aromatic Compounds with Dodecene, J. Catal. 196 (2000) 86-94.

DOI: 10.1006/jcat.2000.3004

Google Scholar

[8] H.L. Shim, S. Udayakumar, J.I. Yu, et. al. Synthesis of cyclic carbonate from allyl glycidyl ether and carbon dioxide using ionic liquid-functionalized amorphous silica, Catal. Today 148 (2009) 350-354.

DOI: 10.1016/j.cattod.2009.06.011

Google Scholar

[9] D.W. Kim, D.J. Hong, K.S. Jang, et. al. Structural modification of polymer-supported ionic liquids as catalysts for nucleophilic substitution reactions including fluorination, Adv. Synth. Catal. 348 (2006) 1719-1727.

DOI: 10.1002/adsc.200606119

Google Scholar

[10] Z.J. Xu, H. Wan, J.M. Miao, et. al. Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterifications, J. Mol. Catal. A: Chem 332 (2010) 152-157.

DOI: 10.1016/j.molcata.2010.09.011

Google Scholar

[11] X.L. Li, Q. L. Ling, Z. L. Liu, et. al. Reusable and Efficient Polystryrene-supported Acidic Ionic Liquid Catalyst for Mononitration of Aromatic Compounds, Bull. Korean Chem. Soc. 2012, 33(2012) 3373-3377.

DOI: 10.5012/bkcs.2012.33.10.3373

Google Scholar

[12] L.X. Li, Q.L. Ling, X.D. Xing, et. al. Reusable and Efficient PS-supported Acidic Ionic Liquid Catalyst for Mononitration of Toluene, Advanced Materials Research, 581-582(2012) 252-257.

DOI: 10.4028/www.scientific.net/amr.581-582.252

Google Scholar

[13] A.S. Amarasekara, O.S. Owereh, Synthesis of a sulfonic acid functionalized acidic ionic liquid modified silica catalyst and applications in the hydrolysis of cellulose, Catal. Commun. 11 (2010) 1072-1075.

DOI: 10.1016/j.catcom.2010.05.012

Google Scholar

[14] F.S. Macintyre, D.C. Sherrington, L. Tetley, Synthesis of Ultrahigh Surface Area Monodisperse Porous Polymer Nanospheres, Macromolecules 39 (2006) 5381-5384.

DOI: 10.1021/ma0610010

Google Scholar

[15] Q. Wu, H. Chen, M.H. Han, et. al. Transesterification of Cottonseed oil catalyzed by bronsted acidic ionic liquids, Ind. Eng. Chem. Res. 46 (2007) 7955-7906.

DOI: 10.1021/ie070678o

Google Scholar

[16] M.J. Earl, S. Haas, C.B. Carl, et. al. Catalystic nitration of aromatics by ionic liquid, CN1469859A, (2004).

Google Scholar

[17] F. Xu, H.Y. Chen, H.B. Zhang, et. al. Protophilic amide ionic liquid assisted esterification and catalysis mechanism, J. Mol. Catal. A: Chem. 307 (2009) 9-12.

DOI: 10.1016/j.molcata.2009.03.003

Google Scholar

[18] S.R. Kirumakki, N. Nagaraju, S. Narayanan, A comparative esterification of benzyl alcohol with acetic acid over zeolites Hβ, HY and HZSM5, Appl. Catal. A 273 (2004) 1-9.

DOI: 10.1016/j.apcata.2004.03.016

Google Scholar

[19] J.Z. Gui, H.Y. Ban, X.H. Cong, et. al. Selective alkylation of phenol with tert-butyl alcohol catalyzed by Brönsted acidic imidazolium salts, J. Mol. Catal. A: Chem. 225 (2005) 27-31.

DOI: 10.1016/j.molcata.2004.08.026

Google Scholar