KCC-1/Pr-SO3H as an efficient heterogeneous catalyst for production of n-butyl levulinate from furfuryl alcohol

Zahra Mohammadbagheri; Alirza Najafi Chermahini

Journal of Industrial and Engineering Chemistry, Vol.62, 401-408, June, 2018

DOI10.1016/j.jiec.2018.01.020 Export Citation

KCC-1/Pr-SO3H as an efficient heterogeneous catalyst for production of n-butyl levulinate from furfuryl alcohol

Zahra Mohammadbagheri, and Alirza Najafi Chermahini^{1, †}

Chemistry Group, Pardis College, Isfahan University of Technology, Isfahan 84156-83111, Iran
¹Department of Chemistry, Isfahan University of Technology, 84154-83111 Isfahan, Iran, Korea

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In this study, production of n-butyl levulinate from furfuryl alcohol was investigated using KCC-1/Pr- SO3H as an efficient heterogeneous catalyst. The catalyst was prepared and characterized using FT-IR, N2 adsorption/desorption, scanning electron microscopy (SEM), transmission electron microscopy (TEM), pyridine-adsorbed FT-IR spectroscopy and TGA techniques. The effects of different parameters on the reaction conditions including temperature, reaction time, catalyst amount, and furfuryl alcohol volume were evaluated. The highest yield of n-butyl levulinate was 81.9% at 120 °C after 3 h. The catalyst was recovered and reused at least four times with insignificant change in yield of n-butyl levulinate.

Keywords:n-Butyl levulinate;Furfuryl alcohol;Biomass conversion;KCC-1;Solid acid catalyst

[References]

Chheda JN, Huber GW, Dumesic JA, Angew. Chem.-Int. Edit., 46, 7164 (2007)
Katryniok B, Paul S, Belliere-Baca V, Rey P, Dumeignil F, Green Chem., 12, 2079 (2010)
Tilman D, Socolow R, Foley JA, Hill J, Larson E, Lynd L, Pacala S, Rrilly J, Searchinger T, Somerville C, Williams R, Science, 325, 270 (2009)
Li X, Wu D, Lu T, Yi G, Su V, Zhang YG, Angew. Chem.-Int. Edit., 53, 4284 (2014)
Corma A, Iborra S, Velty A, Chem. Rev., 107(6), 2411 (2007)
Lichtenthaler FW, Accounts Chem. Res., 35, 728 (2002)
Pasquale G, Vazquez P, Romanelli G, Baronetti G, Catal. Commun., 18, 115 (2012)
Huang Y, Fu Y, Green Chem., 15, 1095 (2013)
Pileidis FD, Tabassum M, Coutts S, Titirici M, Chin. J. Catal., 35, 929 (2014)
Hayes DJ, Catal. Today, 145(1), 138 (2009)
Wang ZW, Lei TZ, Leu L, Zhu JL, He XF, Li ZF, BioResources, 7, 5972 (2012)
Windom BC, Lovestead TM, Mascal M, Nikitin EB, Bruno TJ, Energy Fuels, 25(4), 1878 (2011)
Mao RLV, Zhao Q, Dima G, Petraccone D, Catal. Lett., 141(2), 271 (2011)
Neves P, Lima S, Pillinger M, Rocha SM, Rocha J, Valente AA, Catal. Today, 218-219, 76 (2013)
Guo H, Lian Y, Yan L, Qi X, Smith RL, Green Chem., 15, 2167 (2013)
Jacobson K, Gopinath R, Meher LC, Dalai AK, Appl. Catal. B: Environ., 85(1-2), 86 (2008)
Bertarione S, Bonino F, Cesano F, Jain S, Zanetti M, Scarano D, Zecchina A, J. Phys. Chem. B, 114, 10571 (2009)
Zhang Z, Dong K, Zhao ZK, ChemSusChem, 4, 112 (2011)
Neves P, Lima S, Pillinger M, Rocha SM, Rocha J, Valente AA, Catal. Today, 218, 76 (2013)
Neves P, Russo PA, Fernandes A, Antunes MM, Farinha J, Pillinger M, Ribeiro MF, Castanheiro JE, Valente AA, Appl. Catal. A: Gen., 487, 148 (2014)
Cara PD, Ciriminna R, Shiju NR, Rothenberg G, Pagliaro M, ChemSusChem, 7, 835 (2014)
Zhao G, Hu L, Sun Y, Zeng X, Lin L, BioResources, 9, 2634 (2014)
Rao BS, Kumari PK, Lakshmi DD, Lingaiah N, Catal. Today (2017), doi:http://dx.doi.org/10.1016/j.cattod.2017.05.040 (in press).
Huang YB, Yang T, Zhou MC, Pan H, Fu Y, Green Chem., 18, 1516 (2016)
Enumula SS, Koppadi KS, Gurram VRB, Burri DR, Kamaraju SRR, Sustain. Energy Fuels, 1, 644 (2017)
Fihri A, Cha D, Bouhrara M, Almana N, Polshettiwar V, ChemSusChem, 5, 85 (2012)
Polshettiwar V, Cha D, Zhang X, Basset JM, Angew. Chem.-Int. Edit., 4, 9652 (2010)
Chermahini AN, Shahangi F, Dabbagh HA, Saraji M, RSC Adv., 6, 33804 (2016)
Babou F, Coudurier G, Vedrine JC, J. Catal., 152(2), 341 (1995)
Chen WH, Ko HH, Sakthivel A, Huang SJ, Liu SH, Lo AY, Tsai TC, Liu SB, Catal. Today, 116(2), 111 (2006)
Kao HM, Chang PC, Liao YW, Lee LP, Chien CH, Microporous Mesoporous Mater., 114, 352 (2008)
Maldonado GMG, Asary RS, Dumesic JA, Curttis AL, Energy Environ. Sci., 5, 8990 (2012)
Peng L, Li H, Xi L, Chen K, Chen H, BioResources, 9, 3825 (2014)
Pranger L, Tannenbaum R, Macromolecules, 41(22), 8682 (2008)
Mija A, Navard P, Peiti C, Babor D, Guigo N, Eur. Polym. J., 46, 1380 (2010)
Rao BS, Kumari PK, Dhanalakshmi D, Lingaiah N, J. Mol. Catal. A-Chem., 427, 80 (2017)
Neves P, Antunes MM, Russo PA, Abrantes JB, Lima S, Fernandes A, Pilinger M, Rocha SM, Ribeiro MF, Valante AA, Green Chem., 15, 3367 (2013)

[1] Chheda JN, Huber GW, Dumesic JA, Angew. Chem.-Int. Edit., 46, 7164 (2007)

[2] Katryniok B, Paul S, Belliere-Baca V, Rey P, Dumeignil F, Green Chem., 12, 2079 (2010)

[3] Tilman D, Socolow R, Foley JA, Hill J, Larson E, Lynd L, Pacala S, Rrilly J, Searchinger T, Somerville C, Williams R, Science, 325, 270 (2009)

[4] Li X, Wu D, Lu T, Yi G, Su V, Zhang YG, Angew. Chem.-Int. Edit., 53, 4284 (2014)

[5] Corma A, Iborra S, Velty A, Chem. Rev., 107(6), 2411 (2007)

[6] Lichtenthaler FW, Accounts Chem. Res., 35, 728 (2002)

[7] Pasquale G, Vazquez P, Romanelli G, Baronetti G, Catal. Commun., 18, 115 (2012)

[8] Huang Y, Fu Y, Green Chem., 15, 1095 (2013)

[9] Pileidis FD, Tabassum M, Coutts S, Titirici M, Chin. J. Catal., 35, 929 (2014)

[10] Hayes DJ, Catal. Today, 145(1), 138 (2009)

[11] Wang ZW, Lei TZ, Leu L, Zhu JL, He XF, Li ZF, BioResources, 7, 5972 (2012)

[12] Windom BC, Lovestead TM, Mascal M, Nikitin EB, Bruno TJ, Energy Fuels, 25(4), 1878 (2011)

[13] Mao RLV, Zhao Q, Dima G, Petraccone D, Catal. Lett., 141(2), 271 (2011)

[14] Neves P, Lima S, Pillinger M, Rocha SM, Rocha J, Valente AA, Catal. Today, 218-219, 76 (2013)

[15] Guo H, Lian Y, Yan L, Qi X, Smith RL, Green Chem., 15, 2167 (2013)

[16] Jacobson K, Gopinath R, Meher LC, Dalai AK, Appl. Catal. B: Environ., 85(1-2), 86 (2008)

[17] Bertarione S, Bonino F, Cesano F, Jain S, Zanetti M, Scarano D, Zecchina A, J. Phys. Chem. B, 114, 10571 (2009)

[18] Zhang Z, Dong K, Zhao ZK, ChemSusChem, 4, 112 (2011)

[19] Neves P, Lima S, Pillinger M, Rocha SM, Rocha J, Valente AA, Catal. Today, 218, 76 (2013)

[20] Neves P, Russo PA, Fernandes A, Antunes MM, Farinha J, Pillinger M, Ribeiro MF, Castanheiro JE, Valente AA, Appl. Catal. A: Gen., 487, 148 (2014)

[21] Cara PD, Ciriminna R, Shiju NR, Rothenberg G, Pagliaro M, ChemSusChem, 7, 835 (2014)

[22] Zhao G, Hu L, Sun Y, Zeng X, Lin L, BioResources, 9, 2634 (2014)

[23] Rao BS, Kumari PK, Lakshmi DD, Lingaiah N, Catal. Today (2017), doi:http://dx.doi.org/10.1016/j.cattod.2017.05.040 (in press).

[24] Huang YB, Yang T, Zhou MC, Pan H, Fu Y, Green Chem., 18, 1516 (2016)

[25] Enumula SS, Koppadi KS, Gurram VRB, Burri DR, Kamaraju SRR, Sustain. Energy Fuels, 1, 644 (2017)

[26] Fihri A, Cha D, Bouhrara M, Almana N, Polshettiwar V, ChemSusChem, 5, 85 (2012)

[27] Polshettiwar V, Cha D, Zhang X, Basset JM, Angew. Chem.-Int. Edit., 4, 9652 (2010)

[28] Chermahini AN, Shahangi F, Dabbagh HA, Saraji M, RSC Adv., 6, 33804 (2016)

[29] Babou F, Coudurier G, Vedrine JC, J. Catal., 152(2), 341 (1995)

[30] Chen WH, Ko HH, Sakthivel A, Huang SJ, Liu SH, Lo AY, Tsai TC, Liu SB, Catal. Today, 116(2), 111 (2006)

[31] Kao HM, Chang PC, Liao YW, Lee LP, Chien CH, Microporous Mesoporous Mater., 114, 352 (2008)

[32] Maldonado GMG, Asary RS, Dumesic JA, Curttis AL, Energy Environ. Sci., 5, 8990 (2012)

[33] Peng L, Li H, Xi L, Chen K, Chen H, BioResources, 9, 3825 (2014)

[34] Pranger L, Tannenbaum R, Macromolecules, 41(22), 8682 (2008)

[35] Mija A, Navard P, Peiti C, Babor D, Guigo N, Eur. Polym. J., 46, 1380 (2010)

[36] Rao BS, Kumari PK, Dhanalakshmi D, Lingaiah N, J. Mol. Catal. A-Chem., 427, 80 (2017)

[37] Neves P, Antunes MM, Russo PA, Abrantes JB, Lima S, Fernandes A, Pilinger M, Rocha SM, Ribeiro MF, Valante AA, Green Chem., 15, 3367 (2013)