Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H2O2 solutions

doi:10.1016/S1872-2067(14)60039-5

Abstract

Abstract:

To mitigate the negative environmental impact of greenhouse gas (GHG) emission originated from the use of fossil fuels, the chemical world is switching to utilize renewable biomass resources. Co-producing value-added chemicals is important for an integrated biorefinery to improve economics of biofuels. Lignin derived compounds, e.g. guaiacol, are common by-products of fast pyrolysis of lignocellulosic biomass. In this paper, the feasibility of low-temperature selective oxidation of guaiacol to value-added dicarboxylic acids, e.g. maleic acid, was investigated using titanium silicalite/hydrogen peroxide (TS-1/H₂O₂) reaction system. Under the reaction conditions (80 ℃ and the initial pH = 13.3), the molar yields of maleic acid from guaiacol were approximately 20%-30%. The effects of catalyst amount, initial pH values, reaction time, and temperature on the yields of maleic acid were investigated. A possible reaction mechanism of TS-1 catalyzed aromatic ring opening was proposed.

Key words: Biomass, Lignin, Guaiacol, Oxidation, Maleic acid, TS-1, Hydrogen peroxide, Carboxylic acid

Ji Su, Lisha Yang, Reed Nicholas Liu, Hongfei Lin. Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H₂O₂ solutions[J]. Chinese Journal of Catalysis, 2014, 35(5): 622-630.

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References

[1] U.S. Billion-Ton Update: Biomass Supply for a Bioenergy and Bioproducts Industry, 2011
[2] Bridgwater A V, Meier D, Radlein D. Org Geochem, 1999, 30: 1479
[3] Pattiya A, Titiloye J O, Bridgwater A V. Fuel, 2010, 89: 244
[4] Nowakowski D J, Bridgwater A V, Elliott D C, Meier D, de Wild P. J Anal Appl Pyrolysis, 2010, 88: 53
[5] Bridgwater A V, Peacocke G V C. Renew Sustain Energy Rev, 2000, 4: 1
[6] Vispute T P, Zhang H Y, Sanna A, Xiao R, Huber G W. Science, 2010, 330: 1222
[7] Carlson T R, Tompsett G A, Conner W C, Huber G W. Top Catal, 2009, 52: 241
[8] Bridgwater A V. Biomass Bioenergy, 2012, 38: 68
[9] Zhang Q, Chang J, Wang T J, Xu Y. Energy Convers Manag, 2007, 48: 87
[10] de Miguel Mercader F, Groeneveld M J, Kersten S R A, Geantet C, Toussaint G, Way N W J, Schaverien C J, Hogendoorn K J A. Energy Environ Sci, 2011, 4: 985
[11] Crossley S, Faria J, Shen M, Resasco D E. Science, 2010, 327: 68
[12] Zakzeski J, Bruijnincx P C A, Jongerius A L, Weckhuysen B M. Chem Rev, 2010, 110: 3552
[13] Furimsky E. Appl Catal A, 2000, 199: 147
[14] Zhao C, Kou Y, Lemonidou A A, Li X, Lercher J A. Angew Chem Int Ed, 2009, 121: 4047
[15] Gutierrez A, Kaila R K, Honkela M L, Slioor R, Krause A O I. Catal Today, 2009, 147: 239
[16] Bykova M V, Ermakov D Yu, Kaichev V V, Bulavchenko O A, Saraev A A, Lebedev M Y, Yakovlev V А. Appl Catal B, 2012, 113-114: 296
[17] Jongerius A L, Jastrzebski R, Bruijnincx P C A, Weckhuysen B M. J Catal, 2012, 285: 315
[18] Ruiz P E, Frederick B G, De Sisto W J, Austin R N, Radovic L R, Leiva K, García R, Escalona N, Wheeler M C. Catal Commun, 2012, 27: 44
[19] Ghampson I T, Sepúlveda C, Garcia R, Radovic L R, Fierro J L G, DeSisto W J, Escalona N. Appl Catal A, 2012, 439-440: 111
[20] Zhang X H, Wang T J, Ma L L, Zhang Q, Yu Y X, Liu Q Y. Catal Commun, 2013, 33: 15
[21] Zhao H Y, Li D, Bui P, Oyama S T. Appl Catal A, 2011, 391: 305
[22] Bui V N, Laurenti D, Delichère P, Geantet C. Appl Catal B, 2011, 101: 246
[23] Lee C R, Yoon J S, Suh Y-W, Choi J-W, Ha J-M, Suh D J, Park Y-K. Catal Commun, 2012, 17: 54
[24] Wu S-K, Lai P-C, Lin Y-C, Wan H-P, Lee H-T, Chang Y-H. ACS Sustain Chem Eng, 2013, 1: 349
[25] Ghampson I T, Sepúlveda C, Garcia R, García Fierro J L, Escalona N, DeSisto W J. Appl Catal A, 2012, 435-436: 51
[26] Nimmanwudipong T, Runnebaum R C, Block D E, Gates B C. Energy Fuels, 2011, 25: 3417
[27] Bui V N, Laurenti D, Afanasiev P, Geantet C. Appl Catal B, 2011, 101: 239
[28] Deutsch K L, Shanks B H. Appl Catal A, 2012, 447-448: 144
[29] Olcese R, Bettahar M M, Malaman B, Ghanbaja J, Tibavizco L, Petitjean D, Dufour A. Appl Catal B, 2013, 129: 528
[30] Olcese R N, Bettahar M, Petitjean D, Malaman B, Giovanella F, Dufour A. Appl Catal B, 2012, 115-116: 63
[31] Nimmanwudipong T, Runnebaum R C, Block D E, Gates B C. Catal Lett, 2011, 141: 779
[32] Sasaki M, Goto M, Mater J. Cycles Waste Manag, 2011, 13: 68
[33] Kanetake T, Sasaki M, Goto M. Chem Eng Technol, 2007, 30: 1113
[34] Suzuki H, Cao J, Jin F, Kishita A, Enomoto H, Moriya T. J Mater Sci, 2006, 41: 1591
[35] Devlin H R, Harris I J. Ind Eng Chem Fundam, 1984, 23: 387
[36] Santos A, Yustos P, Quintanilla A, Ruiz G, Garcia-Ochoa F. Appl Catal B, 2005, 61: 323
[37] Santos A, Yustos P, Quintanilla A, García-Ochoa F, Casas J A, Rodríguez J J. Environ Sci Technol, 2004, 38: 133
[38] Santos A, Yustos P, Quintanilla A, Rodriguez S, Garcia-Ochoa F. Appl Catal B, 2002, 39: 97
[39] Wu Z C, Zhou M H. Environ Sci Technol, 2001, 35: 2698
[40] Zazo J A, Casas J A, Molina C B, Quintanilla A, Rodriguez J J. Environ Sci Technol, 2007, 41: 7164
[41] Felthouse T R, Burnett J C, Mitchell S F, Mummey M J. Van Nostrand's Encycl Chem, 2005: 1
[42] Lin H F, Strull J, Liu Y, Karmiol Z, Plank K, Miller G, Guo Z H, Yang L S. Energy Environ Sci, 2012, 5: 9773
[43] Thangaraj A, Sivasanker S. J Chem Soc, Chem Commun, 1992: 123
[44] Blanco-Brieva G, Capel-Sanchez M C, de Frutos M P, Padilla-Polo A, Campos-Martin J M, Fierro J L G. Ind Eng Chem Res, 2008, 47: 8011
[45] Clerici M G. Top Catal, 2001, 15: 257
[46] Klemm E, Dietzsch E, Schwarz T, Kruppa T, de Oliveira A L, Becker F, Markowz G, Schirrmeister S, Schütte R, Caspary K J, Schüth F, Hönicke D. Ind Eng Chem Res, 2008, 47: 2086
[47] Beziat J-C, Besson M, Gallezot P, Durecu S. J Catal, 1999, 182: 129
[48] Oliviero L, Barbier J Jr, Duprez D, Wahyu H, Ponton J W, Metcalfe I S, Mantzavinos D. Appl Catal B, 2001, 35: 1
[49] Hamoudi S, Larachi F, Sayari A. J Catal, 1998, 177: 247
[50] Akolekar D B, Bhargava S K, Shirgoankar I, Prasad J. Appl Catal A, 2002, 236: 255
[51] Gomes H T, Figueiredo J L, Faria J L. Appl Catal B, 2000, 27: L217
[52] Beziat J C, Besson M, Gallezot P, Durecu S. Ind Eng Chem Res, 1999, 38: 1310
[53] Pintar A, Besson M, Gallezot P. Appl Catal B, 2001, 30: 123
[54] Imamura S. Ind Eng Chem Res, 1999, 38: 1743
[55] Bhargava S, Jani H, Tardio J, Akolekar D, Hoang M. Ind Eng Chem Res, 2007, 46: 8652
[56] Luck F. Catal Today, 1999, 53: 81
[57] Doerge D R, Divi R L, Churchwell M I. Anal Biochem, 1997, 250: 10
[58] Taurog A, Dorris M L, Guziec F S Jr. Anal Biochem, 1992, 205: 271
[59] Mijangos F, Varona F, Villota N. Environ Sci Technol, 2006, 40: 5538
[60] Regeimbal J, Gleiter S, Trumpower B L, Yu C-A, Diwakar M, Ballou D P, Bardwell J C A. Proc Natl Acad Sci USA, 2003, 100: 13779
[61] Bonino F, Damin A, Ricchiardi G, Ricci M, Spano G, D'Aloisio R, Zecchina A, Lamberti C, Prestipino C, Bordiga S. J Phys Chem B, 2004, 108: 3573
[62] Chaudhari K, Srinivas D, Ratnasamy P. J Catal, 2001, 203: 25
[63] Shetti V N, Manikandan P, Srinivas D, Ratnasamy P. J Catal, 2003, 216: 461
[64] Srinivas D, Manikandan P, Laha S C, Kumar R, Ratnasamy P. J Catal, 2003, 217: 160
[65] Wang L L, Xiong G, Su J, Li P, Guo H C. J Phys Chem C, 2012, 116: 9122
[66] Gleeson D, Sankar G, Catlow C R A, Thomas J M, Spano G, Bordiga S, Zecchina A, Lamberti C. Phys Chem Chem Phys, 2000, 2: 4812
[67] Zhao Q, Bao X H, Wang Y, Lin L W, Li G, Guo X W, Wang X S. J Mol Catal A, 2000, 157: 265
[68] Shetti V N, Srinivas D, Ratnasamy P. J Mol Catal A, 2004, 210: 171

Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H₂O₂ solutions

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