催化选择转化多羟基化合物制备高附加值化学品研究进展

doi:10.1016/S1872-2067(11)60501-9

摘要/Abstract

摘要：

对近年来催化转化多羟基化合物制备5-羟甲基糠醛、乙二醇、1,2-丙二醇、1,3-丙二醇等高附加值化学品进行了综述. 分析了果糖、葡萄糖、纤维素等不同结构的碳水化合物制5-羟甲基糠醛存在的挑战, 并对相应的解决方法进行了总结. 对于5-羟甲基糠醛的转化, 我们重点讨论了5-羟甲基糠醛选择性氧化制备2,5-二甲酰基呋喃和2,5-呋喃二甲酸以及它们作为聚合单体的潜在应用. 概述了催化氢解纤维素、糖醇、甘油等多羟基化合物制备乙二醇、1,2-丙二醇、1,3-丙二醇等二元醇的方法, 并对可能的机理进行了讨论. 依据近年来多羟基化合物催化选择性转化制备高附加值化学品的研究现状, 对今后的研究热点进行了展望.

关键词: 生物质, 催化, 呋喃衍生物, 多羟基化合物, 可再生资源

Abstract:

In this review, we discuss recent progress in the catalytic transformation of polyols to value-added chemicals, including 5-hydroxymethylfurfural (HMF), ethylene glycol (EG), 1,2-propylene glycol (1,2-PG) and 1,3-propylene glycol (1,3-PG). The challenges and solving of the synthesis of HMF from different carbohydrates, such as fructose, glucose and cellulose are analyzed. For the conversion of HMF, we focus on the catalytic oxidation of HMF to 2,5-diformylfuran and 2,5-furandicarboxylic acid and their applications to polymers. Advances in thecatalytic hydrogenolysis of polyols including cellulose, sugar alcohols and glycerol to diols such as EG, 1,2-PG and 1,3-PG are reviewed, and the reaction mechanismswere discussed. Research topics are suggested for future research from this review onthe selective catalytic transformation of ployols to value-added chemicals.

Key words: Biomass, Catalysis, Furan derivative, Polyol, Renewable resource

马继平, 于维强, 王敏, 贾秀全, 路芳, 徐杰. 催化选择转化多羟基化合物制备高附加值化学品研究进展[J]. 催化学报, 2013, 34(3): 492-507.

MA Jiping, YU Weiqiang, WANG Min, JIA Xiuquan, LU Fang, XU Jie. Advances in selective catalytic transformation of ployols to value-added chemicals[J]. Chinese Journal of Catalysis, 2013, 34(3): 492-507.

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参考文献

[1] Gallezot P. Chem Soc Rev, 2012, 41: 1538

[2] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588

[3] Corma A, Iborra S, Velty A. Chem Rev, 2007, 107: 2411

[4] Serrano-Ruiz J C, Luque R, Sepulveda-Escribano A. Chem Soc Rev, 2011, 40: 5266

[5] Song Q, Wang F, Xu J. Chem Commun, 2012, 48: 7019

[6] Che P H, Lu F, Zhang J J, Huang Y Z, Nie X, Gao J, Xu J. Bioresour Technol, 2012, 119: 433

[7] Ma H, Nie X, Cai J Y, Chen C, Gao J, Miao H, Xu J. Sci ChinaChem, 2010, 53: 1497

[8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554

[9] Wang F, Xu J, Dubois J L, Ueda W. ChemSusChem, 2010, 3: 1383

[10] Liu J X, Du Z T, Yang Y L, Lu T L, Lu F, Xu J. ChemSusChem, 2012, 5: 2151

[11] Shuttleworth P, Budarin V, Gronnow M, Clark J H, Luque R. J Nat Gas Chem, 2012, 21: 270

[12] Luque R, Pineda A, Colmenares J C, Campelo J M, Romero A A, Serrano-Ruiz J C, Cabeza L F, Cot-Gores J. J Nat Gas Chem, 2012, 21: 246

[13] Yang P F, Kobayashi H, Fukuoka A. Chin J Catal(催化学报), 2011, 32: 716

[14] Zhang Y M, Degirmenci V, Li C, Hensen E J M. ChemSusChem, 2011, 4: 59

[15] Zhang J, Wu S B, Li B, Zhang H D. ChemCatChem, 2012, 4: 1230

[16] Roman-Leshkov Y, Barrett C J, Liu Z Y, Dumesic J A. Nature, 2007, 447: 982

[17] Hu L, Sun Y, Lin L. Prog Chem (胡磊, 孙勇, 林鹿. 化学进展), 2011, 23: 2079

[18] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754

[19] Tong X L, Ma Y, Li Y D. Appl Catal A, 2010, 385: 1

[20] Lewkowski J. Arkivoc, 2001, 2: 17

[21] Shimizu K, Satsuma A. Energy Environ Sci, 2011, 4: 3140

[22] Shi N, Liu Q Y, Wang T J, Zhang Q, Ma L L. Chem Ind Eng Pro(石宁, 刘琪英, 王铁军, 张琦, 马隆龙. 化工进展), 2012, 31: 792

[23] Chen W W, Li C X.[MSDissertation]. Beijing: Beijing Univ Chem Technol(陈文文, 李春喜.[硕士论文]. 北京: 北京化工大学), 2012

[24] An S Y, Jin L H, Hu D Y, Zhang Y P, Xue W, Yang S. Chem World (安士云, 金林红, 胡德禹, 张钰萍, 薛伟, 杨松. 化学世界), 2012, (7): 441

[25] Jiang N, Qi W, Huang R L, Su X R, He Z M. Chem Ind Eng Pro(姜楠, 齐葳, 黄仁亮, 苏欣荣, 何志敏. 化工进展), 2011, 30: 1937

[26] Hu L, Sun Y, Lin L. Chem Ind Eng Pro(胡磊, 孙勇, 林鹿. 化工进展), 2011, 30: 1711

[27] Zhang Z Y, Zhang Z C, Li J, Dai H, Li L X. Chem Res Appl(张正源, 张宗才, 李洁, 戴红, 李立新. 化学研究与应用), 2010, 22: 257

[28] Yang F L, Liu Q S, Bai X F, Du Y G. Modern Chem Ind(杨凤丽, 刘启顺, 白雪芳, 杜昱光. 现代化工), 2009, 29: 18

[29] Wang J, Zhang C P, Ouyang P K. Chem Ind Eng Pro(王军, 张春鹏, 欧阳平凯. 化工进展), 2008, 28: 702

[30] Wang J J, Xu W J, Ren J W, Liu X H, Lu G Z, Wang Y Q. Green Chem, 2011, 13: 2678

[31] Yang F L, Liu Q S, Yue M, Bai X F, Du Y G. Chem Commun, 2011, 47: 4469

[32] Bicker M, Kaiser D, Ott L, Vogel H. J Supercrit Fluid, 2005, 36: 118

[33] Moreau C, Finiels A, Vanoye L. J Mol Catal A, 2006, 253: 165

[34] Li C Z, Zhao Z K, Wang A Q, Zheng M Y, Zhang T. Carbohydr Res, 2010, 345: 1846

[35] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2009, 11: 1327

[36] Lai D M, Deng L, Li J A, Liao B, Guo Q X, Fu Y. ChemSusChem, 2011, 4: 55

[37] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933

[38] Roman-Leshkov Y, Dumesic J A. Top Catal, 2009, 52: 297

[39] Shimizu K, Uozumi R, Satsuma A. Catal Commun, 2009, 10: 1849

[40] Tuercke T, Panic S, Loebbecke S. Chem Eng Technol, 2009, 32: 1815

[41] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2008, 10: 799

[42] Li C Z, Zhao Z B K, Cai H L, Wang A Q, Zhang T. Biomass Bioenerg, 2011, 35: 2013

[43] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597

[44] Yong G, Zhang Y G, Ying J Y. Angew Chem, Int Ed, 2008, 47: 9345

[45] Zhang Y M, Pidko E A, Hensen E J M. Chem-Eur J, 2011, 17: 5281

[46] Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, Konig B. Green Chem, 2009, 11: 1948

[47] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Angew Chem, Int Ed, 2010, 49: 2530

[48] Zhang Z H, Zhao Z B. Bioresour Technol, 2011, 102: 3970

[49] Li C Z, Zhang Z H, Zhao Z B K. Tetrahedron Lett, 2009, 50: 5403

[50] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746

[51] Chen T M, Lin L. Chin J Chem, 2010, 28: 1773

[52] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131

[53] Pagan-Torres Y J, Wang T F, Gallo J M R, Shanks B H, Dumesic J A. ACS Catal, 2012, 2: 930

[54] Nikolla E, Roman-Leshkov Y, Moliner M, Davis M E. ACS Catal, 2011, 1: 408

[55] Wang J J, Ren J W, Liu X H, Xi J X, Xia Q N, Zu Y H, Lu G Z, Wang Y Q. Green Chem, 2012, 14: 2506

[56] Yasuda M, Nakamura Y, Matsumoto J, Yokoi H, Shiragami T. Bull Chem Soc Jpn, 2011, 84: 416

[57] Wang T F, Pagan-Torres Y J, Combs E J, Dumesic J A, Shanks B H. Top Catal, 2012, 55: 657

[58] Stahlberg T, Sorensen M G, Riisager A. Green Chem, 2010, 12: 321

[59] Takagaki A, Ohara M, Nishimura S, Ebitani K. Chem Commun, 2009: 6276

[60] Watanabe M, Aizawa Y, Iida T, Nishimura R, Inomata H. Appl Catal A, 2005, 295: 150

[61] Watanabe M, Aizawa Y, Iida T, Aida T M, Levy C, Sue K, Inomata H. Carbohydr Res, 2005, 340: 1925

[62] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558

[63] Huang R L, Qi W, Su R X, He Z M. Chem Commun, 2010, 46: 1115

[64] Stahlberg T, Rodriguez-Rodriguez S, Fristrup P, Riisager A. Chem-Eur J, 2011, 17: 1456

[65] Sheldon R. Chem Commun, 2001: 2399

[66] Zhang Z H, Wang W Q, Liu X Y, Wang Q, Li W X, Xie H B, Zhao Z B K. Bioresour Technol, 2012, 112: 151

[67] Zhang Z H, Zhao Z B K. Bioresour Technol, 2010, 101: 1111

[68] Zhang Z H, Zhao Z B K. Carbohydr Res, 2009, 344: 2069

[69] Li C Z, Wang Q, Zhao Z B K. Green Chem, 2008, 10: 177

[70] Li C Z, Zhao Z K B. Adv Synth Catal, 2007, 349: 1847

[71] Swatloski R P, Spear S K, Holbrey J D, Rogers R D. J Am Chem Soc, 2002, 124: 4974

[72] Rinaldi R, Palkovits R, Schuth F. Angew Chem, Int Ed, 2008, 47: 8047

[73] Su Y, Brown H M, Huang X, Zhou X-D, Amonette J E, Zhang Z C. Appl Catal A, 2009, 361: 117

[74] Qi X H, Watanabe M, Aida T M, Smith R L. Cellulose, 2011, 18: 1327

[75] Zhang Y T, Du H B, Qian X H, Chen E Y X. Energy Fuel, 2010, 24: 2410

[76] Wu S C, Wang C L, Gao Y J, Zhang S C, Ma D, Zhao Z B. Chin J Cat-al(吴树昌, 王春雷, 高勇军, 张少春, 马丁, 赵宗保. 催化学报), 2010, 31: 1157

[77] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979

[78] Haworth W N, Jones W G M. J Chem Soc, 1944: 667

[79] Antal M J, Mok W S L, Richards G N. Carbohydr Res, 1990, 199: 111

[80] Newth F H. Adv Carbohydr Chem, 1951, 6: 83

[81] Amarasekara A S, Williams L D, Ebede C C. Carbohydr Res, 2008, 343: 3021

[82] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Inorg Chem, 2010, 49: 10081

[83] Roman-Leshkov Y, Moliner M, Labinger J A, Davis M E. Angew Chem, Int Ed, 2010, 49: 8954

[84] Hopkins K T, Wilson W D, Bender B C, Mccurdy D R, Hall J E, Tidwell R R, Kumar A, Bajic M, Boykin D W. J Med Chem, 1998, 41: 3872

[85] Del Poeta M, Schell W A, Dykstra C C, Jones S, Tidwell R R, Czarny A, Bajic M, Kumar A, Boykin D, Perfect J R. Antimicrob Agents Ch, 1998, 42: 2495

[86] Howarth O W, Morgan G G, Mckee V, Nelson J. J Chem Soc, Dalton Trans, 1999: 2097

[87] Richter D T, Lash T D. Tetrahedron Lett, 1999, 40: 6735

[88] Benahmed-Gasmi A S, Frere P, Jubault M, Gorgues A, Cousseau J, Garrigues B. Synth Met, 1993, 56: 1751

[89] Hui Z, Gandini A. Eur Polym J, 1992, 28: 1461

[90] Amarasekara A S, Green D, Williams L D. Eur Polym J, 2009, 45: 595

[91] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51

[92] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346

[93] Mehdi H, Bodor A, Lantos D, Horvath I T, De Vos D E, Binnemans K. J Org Chem, 2007, 72: 517

[94] Yoon H J, Choi J W, Jang H S, Cho J K, Byun J W, Chung W J, Lee S M, Lee Y S. Synlett, 2011: 165

[95] Cottier L, Descotes G, Lewkowski J, Skowronski R, Viollet E. J Heterocycl Chem, 1995, 32: 927

[96] Sheldon R A. Stud Surf Sci Catal, 1991, 59: 33

[97] Van Deurzen M P J, Van Rantwijk F, Sheldon R A. J Carbohydr Chem, 1997, 16: 299

[98] Amarasekara A S, Green D, Mcmillan E. Catal Commun, 2008, 9: 286

[99] Verdeguer P, Merat N, Gaset A. J Mol Catal, 1993, 85: 327

[100] Partenheimer W, Grushin V V. Adv Synth Catal, 2001, 343: 102

[101] Moreau C, Durand R, Pourcheron C, Tichit D. Stud Surf Sci Catal, 1997, 108: 399

[102] Carlini C, Patrono P, Galletti A M R, Sbrana G, Zima V. Appl Catal A, 2005, 289: 197

[103] Navarro O C, Canos A C, Chornet S I. Top Catal, 2009, 52: 304

[104] Nie J F, Liu H C. Pure Appl Chem, 2012, 84: 765

[105] Halliday G A, Young R J, Grushin V V. Org Lett, 2003, 5: 2003

[106] Takagaki A, Takahashi M, Nishimura S, Ebitani K. ACS Catal, 2011, 1: 1562

[107] Xiang X, He L, Yang Y, Guo B, Tong D M, Hu C W. Catal Lett, 2011, 141: 735

[108] Yang Z Z, Deng J, Pan T, Guo Q X, Fu Y. Green Chem, 2012, 14: 2986

[109] Moore J A, Kelly J E. Macromolecules, 1978, 11: 568

[110] Moore J A, Kelly J E. J Polym Sci Pol Chem, 1978, 16: 2407

[111] Moore J A, Kelly J E. Polymer, 1979, 20: 627

[112] Moore J A, Kelly J E. J Polym Sci Pol Chem, 1984, 22: 863

[113] Gandini A, Silvestre A J D, Pascoal Neto C, Sousa A F, Gomes M. J Polym Sci Pol Chem, 2009, 47: 295

[114] Gomes M, Gandini A, Silvestre A J D, Reis B. J Polym Sci Pol Chem, 2011, 49: 3759

[115] Jiang M, Liu Q, Zhang Q, Ye C, Zhou G Y. J Polym Sci Pol Chem, 2012, 50: 1026

[116] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. J Mater Chem, 2012, 22: 3457

[117] Ma J P, Yu X F, Xu J, Pang Y. Polymer, 2012, 53: 4145

[118] Wu L B, Mincheva R, Xu Y T, Raquez J M, Dubois P. Biomacromolecules, 2012, 13: 2973

[119] Eerhart A J J E, Faaij A P C, Patel M K. Energy Environ Sci, 2012, 5: 6407

[120] Gandini A. Polym Chem, 2010, 1: 245

[121] Gandini A, Coelho D, Gomes M, Reis B, Silvestre A. J Mater Chem, 2009, 19: 8656

[122] Gandini A. Macromolecules, 2008, 41: 9491

[123] Moreau C, Belgacem M N, Gandini A. Top Catal, 2004, 27: 11

[124] Werpy T, Petersen G. In: Top Value Added Chemicals from Biomass. Volume I: Results of Screening for Potential Candidates from Sugars and Synthesis Gas. Top 12 Candidate Summary Bios. Oak Ridge: US Department of Energy Report, 2004. 21

[125] Saha B, Dutta S, Abu-Omar M M. Catal Sci Technol, 2012, 2: 79

[126] Vinke P, Van Dam H E, Van Bekkum H, Centi G, Trifiro F. Stud Surf Sci Catal, 1990, 55: 147

[127] Hughes M D, Xu Y J, Jenkins P, Mcmorn P, Landon P, Enache D I, Carley a F, Attard G A, Hutchings G J, King F, Stitt E H, Johnston P, Griffin K, Kiely C J. Nature, 2005, 437: 1132

[128] Hashmi A S K, Hutchings G J. Angew Chem, Int Ed, 2006, 45: 7896

[129] Taarning E, Nielsen I S, Egeblad K, Madsen R, Christensen C H. ChemSusChem, 2008, 1: 75

[130] Gorbanev Y Y, Klitgaard S K, Woodley J M, Christensen C H, Rii-sager A. ChemSusChem, 2009, 2: 672

[131] Casanova O, Iborra S, Corma A. ChemSusChem, 2009, 2: 1138

[132] Casanova O, Iborra S, Corma A. J Catal, 2009, 265: 109

[133] Pasini T, Piccinini M, Blosi M, Bonelli R, Albonetti S, Dimitratos N, Lopez-Sanchez J A, Sankar M, He Q, Kiely C J, Hutchings G J, Cavani F. Green Chem, 2011, 13: 2091

[134] Gupta N K, Nishimura S, Takagaki A, Ebitani K. Green Chem, 2011, 13: 824

[135] Gorbanev Y, Kegnæs S, Riisager A. Top Catal, 2011, 54: 1318

[136] Gorbanev Y Y, Kegnæs S, Riisager A. Catal Lett, 2011, 141: 1752

[137] Davis S E, Houk L R, Tamargo E C, Datye A K, Davis R J. Catal To-day, 2011, 160: 55

[138] Kroger M, Prusse U, Vorlop K D. Top Catal, 2000, 13: 237

[139] Ribeiro M L, Schuchardt U. Catal Commun, 2003, 4: 83

[140] Fukuoka A, Dhepe P L. Angew Chem, Int Ed, 2006, 45: 5161

[141] Yan N, Zhao C, Luo C, Dyson P J, Liu H C, Kou Y. J Am Chem Soc, 2006, 128: 8714

[142] Luo C, Wang S, Liu H C. Angew Chem, Int Ed, 2007, 46: 7636

[143] Deng W P, Tan X S, Fang W H, Zhang Q H, Wang Y. Catal Lett, 2009, 133: 167

[144] Van De Vyver S, Geboers J, Dusselier M, Schepers H, Vosch T, Zhang L, Van Tendeloo G, Jacobs P A, Sels B F. ChemSusChem, 2010, 3: 698

[145] Ding L N, Wang A Q, Zheng M Y, Zhang T. ChemSusChem, 2010, 3: 818

[146] Geboers J, Van De Vyver S, Carpentier K, De Blochouse K, Jacobs P, Sels B. Chem Commun, 2010, 46: 3577

[147] Palkovits R, Tajvidi K, Ruppert A M, Procelewska J. Chem Commun, 2011, 47: 576

[148] Miyazawa T, Koso S, Kunimori K, Tomishige K. Appl Catal A, 2007, 318: 244

[149] Balaraju M, Rekha V, Prasad P S S, Devi B L A P, Prasad R B N, Lingaiah N. Appl Catal A, 2009, 354: 82

[150] Alhanash A, Kozhevnikova E F, Kozhevnikov I V. Catal Lett, 2008, 120: 307

[151] Hamzah N, Nordin N M, Nadzri A H A, Nik Y A, Kassim M B, Yarmo M A. Appl Catal A, 2012, 419: 133

[152] Ma L, He D H. Chin J Catal(马兰, 贺德华. 催化学报), 2009, 30: 471

[153] Yuan Z L, Wu P, Gao J, Lu X Y, Hou Z Y, Zheng X M. Catal Lett, 2009, 130: 261

[154] Furikado I, Miyazawa T, Koso S, Shimao A, Kunimori K, Tomi-shige K. Green Chem, 2007, 9: 582

[155] Musolino M G, Scarpino L A, Mauriello F, Pietropaolo R. ChemSusChem, 2011, 4: 1143

[156] Yin A Y, Guo X Y, Dai W L, Fan K N. Green Chem, 2009, 11: 1514

[157] Yu W Q, Zhao J, Ma H, Miao H, Song Q, Xu J. Appl Catal A, 2010, 383: 73

[158] Zhao J, Yu W Q, Chen C, Miao H, Ma H, Xu J. Catal Lett, 2010, 134: 184

[159] Dasari M A, Kiatsimkul P P, Sutterlin W R, Suppes G J. Appl Catal A, 2005, 281: 225

[160] Huang Z W, Cui F, Kang H X, Chen J, Zhang X Z, Xia C G. Chem Ma-ter, 2008, 20: 5090

[161] Chaminand J, Djakovitch L, Gallezot P, Marion P, Pinel C, Rosier C. Green Chem, 2004, 6: 359

[162] Wang S, Liu H C. Catal Lett, 2007, 117: 62

[163] Zhou J X, Zhang J, Guo X W, Mao J B, Zhang S G. Green Chem, 2012, 14: 156

[164] Miyazawa T, Koso S, Kunimori K, Tomishige K. Appl Catal A, 2007, 329: 30

[165] Maris E P, Ketchie W C, Murayama M, Davis R J. J Catal, 2007, 251: 281

[166] Maris E P, Davis R J. J Catal, 2007, 249: 328

[167] Jiang T, Zhou Y X, Liang S G, Liu H Z, Han B X. Green Chem, 2009, 11: 1000

[168] Feng J, Fu H Y, Wang J B, Li R X, Chen H, Li X J. Catal Commun, 2008, 9: 1458

[169] Feng J, Xiong W, Jia Y, Wang J, Liu D, Chen H, Li X. Chin J Catal (冯建, 熊伟, 贾云, 王金波, 刘德蓉, 陈华, 李贤均. 催化学报), 2011, 32: 1545

[170] Ma L, He D H, Li Z P. Catal Commun, 2008, 9: 2489

[171] Vasiliadou E S, Heracleous E, Vasalos I A, Lemonidou A A. Appl Catal B, 2009, 92: 90

[172] Musolino M G, Scarpino L A, Mauriello F, Pietropaolo R. Green Chem, 2009, 11: 1511

[173] Feng J, Wang J B, Zhou Y F, Fu H Y, Chen H, Li X J. Chem Lett, 2007, 36: 1274

[174] Xia S, Yuan Z, Wang L, Chen P, Hou Z. Appl Catal A, 2011, 403: 173

[175] Huang J H, Chen J X. Chin J Catal (黄金花, 陈吉祥. 催化学报), 2012, 33: 790

[176] Jimenez-Morales I, Vila F, Mariscal R, Jimenez-Lopez A. Appl Catal B, 2012, 117: 253

[177] Yu W Q, Xu J, Ma H, Chen C, Zhao J, Miao H, Song Q. Catal Commun, 2010, 11: 493

[178] Liang C H, Ma Z Q, Ding L, Qiu J S. Catal Lett, 2009, 130: 169

[179] Balaraju M, Rekha V, Prasad P S S, Prasad R B N, Lingaiah N. Catal Lett, 2008, 126: 119

[180] Wang S A, Zhang Y C, Liu H C. Chem-Asian J, 2010, 5: 1100

[181] Clark I. Ind Eng Chem, 1958, 50: 1125

[182] Tanikella M S S R. US Patent 4404411. 1983

[183] Werpy T A, Frye Jr. J G, Zacher A H, Miller D J. US Patent 6841085. 2005

[184] Banu M, Sivasanker S, Sankaranarayanan T M, Venuvanalingam P. Catal Commun, 2011, 12: 673

[185] Sun J, Liu H. Green Chem, 2011, 13: 135

[186] Zhou J H, Zhang M G, Zhao L, Li P, Zhou X G, Yuan W K. Catal To-day, 2009, 147: S225

[187] Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Chen J G. Angew Chem, Int Ed, 2008, 47: 8510

[188] Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Shu Y, Stottlemyer A L, Chen J G. Catal Today, 2009, 147: 77

[189] Zhang Y H, Wang A Q, Zhang T. Chem Commun, 2010, 46: 862

[190] Zheng M Y, Wang A Q, Ji N, Pang J F, Wang X D, Zhang T. Chem-SusChem, 2010, 3: 63

[191] Zhao G H, Zheng M Y, Wang A Q, Zhang T. Chin J Catal (赵冠鸿, 郑明远, 王爱琴, 张涛. 催化学报), 2010, 31: 928

[192] Liu Y, Luo C, Liu H C. Angew Chem, Int Ed, 2012, 51: 3249

[193] Pang J F, Zheng M Y, Wang A Q, Zhang T. Ind Eng Chem Res, 2011, 50: 6601

[194] Li C Z, Zheng M Y, Wang A Q, Zhang T. Energy Environ Sci, 2012, 5: 6383

[195] Zhou L K, Wang A Q, Li C Z, Zheng M Y, Zhang T. ChemSusChem, 2012, 5: 932

[196] Kurosaka T, Maruyama H, Naribayashi I, Sasaki Y. Catal Commun, 2008, 9: 1360

[197] Gong L F, Lu Y, Ding Y J, Lin R H, Li J W, Dong W D, Wang T, Chen W M. Chin J Catal (龚磊峰, 吕元, 丁云杰, 林荣和, 李经纬, 董文达, 王涛, 陈维苗. 催化学报), 2009, 30: 1189

[198] Qin L Z, Song M J, Chen C L. Green Chem, 2010, 12: 1466

[199] Gong L F, Lu Y A, Ding Y J, Lin R H, Li J W, Dong W D, Wang T, Chen W M. Appl Catal A, 2010, 390: 119

[200] Oh J, Dash S, Lee H. Green Chem, 2011, 13: 2004

[201] Nakagawa Y, Shinmi Y, Koso S, Tomishige K. J Catal, 2010, 272: 191

[202] Huang L, Zhu Y L, Zheng H Y, Ding G Q, Li Y W. Catal Lett, 2009, 131: 312

[203] Zhu S H, Zhu Y L, Hao S L, Chen L G, Zhang B, Li Y W. Catal Lett, 2012, 142: 267

[204] Amada Y, Shinmi Y, Koso S, Kubota T, Nakagawa Y, Tomishige K. Appl Catal B, 2011, 105: 117

[205] Chen Ch L, Song M J, Qin L Zh. J Nanjing Univ Technol (Natur Sci Ed)(陈长林,宋敏洁,秦丽珍. 南京工业大学学报 (自然科学版)), 2011, 33: 1

[206] Gallo J M R, Alonso D M, Mellmer M A, Dumesic J A. Green Chem, 2013, 15: 85