Citation:
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.
doi:
10.1016/S1872-2067(11)60501-9
-
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.
-
Keywords:
- Biomass,
- Catalysis,
- Furan derivative,
- Polyol,
- Renewable resource
-
-
-
[1]
[1] Gallezot P. Chem Soc Rev, 2012, 41: 1538
-
[2]
[2] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588
-
[3]
[3] Corma A, Iborra S, Velty A. Chem Rev, 2007, 107: 2411
-
[4]
[4] Serrano-Ruiz J C, Luque R, Sepulveda-Escribano A. Chem Soc Rev, 2011, 40: 5266
-
[5]
[5] Song Q, Wang F, Xu J. Chem Commun, 2012, 48: 7019
-
[6]
[6] Che P H, Lu F, Zhang J J, Huang Y Z, Nie X, Gao J, Xu J. Bioresour Technol, 2012, 119: 433
-
[7]
[7] Ma H, Nie X, Cai J Y, Chen C, Gao J, Miao H, Xu J. Sci ChinaChem, 2010, 53: 1497
-
[8]
[8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554
-
[9]
[9] Wang F, Xu J, Dubois J L, Ueda W. ChemSusChem, 2010, 3: 1383
-
[10]
[10] Liu J X, Du Z T, Yang Y L, Lu T L, Lu F, Xu J. ChemSusChem, 2012, 5: 2151
-
[11]
[11] Shuttleworth P, Budarin V, Gronnow M, Clark J H, Luque R. J Nat Gas Chem, 2012, 21: 270
-
[12]
[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]
[13] Yang P F, Kobayashi H, Fukuoka A. Chin J Catal(催化学报), 2011, 32: 716
-
[14]
[14] Zhang Y M, Degirmenci V, Li C, Hensen E J M. ChemSusChem, 2011, 4: 59
-
[15]
[15] Zhang J, Wu S B, Li B, Zhang H D. ChemCatChem, 2012, 4: 1230
-
[16]
[16] Roman-Leshkov Y, Barrett C J, Liu Z Y, Dumesic J A. Nature, 2007, 447: 982
-
[17]
[17] Hu L, Sun Y, Lin L. Prog Chem (胡磊, 孙勇, 林鹿. 化学进展), 2011, 23: 2079
-
[18]
[18] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754
-
[19]
[19] Tong X L, Ma Y, Li Y D. Appl Catal A, 2010, 385: 1
-
[20]
[20] Lewkowski J. Arkivoc, 2001, 2: 17
-
[21]
[21] Shimizu K, Satsuma A. Energy Environ Sci, 2011, 4: 3140
-
[22]
[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]
[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]
[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]
[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]
[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]
[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]
[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]
[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]
[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]
[31] Yang F L, Liu Q S, Yue M, Bai X F, Du Y G. Chem Commun, 2011, 47: 4469
-
[32]
[32] Bicker M, Kaiser D, Ott L, Vogel H. J Supercrit Fluid, 2005, 36: 118
-
[33]
[33] Moreau C, Finiels A, Vanoye L. J Mol Catal A, 2006, 253: 165
-
[34]
[34] Li C Z, Zhao Z K, Wang A Q, Zheng M Y, Zhang T. Carbohydr Res, 2010, 345: 1846
-
[35]
[35] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2009, 11: 1327
-
[36]
[36] Lai D M, Deng L, Li J A, Liao B, Guo Q X, Fu Y. ChemSusChem, 2011, 4: 55
-
[37]
[37] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933
-
[38]
[38] Roman-Leshkov Y, Dumesic J A. Top Catal, 2009, 52: 297
-
[39]
[39] Shimizu K, Uozumi R, Satsuma A. Catal Commun, 2009, 10: 1849
-
[40]
[40] Tuercke T, Panic S, Loebbecke S. Chem Eng Technol, 2009, 32: 1815
-
[41]
[41] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2008, 10: 799
-
[42]
[42] Li C Z, Zhao Z B K, Cai H L, Wang A Q, Zhang T. Biomass Bioenerg, 2011, 35: 2013
-
[43]
[43] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597
-
[44]
[44] Yong G, Zhang Y G, Ying J Y. Angew Chem, Int Ed, 2008, 47: 9345
-
[45]
[45] Zhang Y M, Pidko E A, Hensen E J M. Chem-Eur J, 2011, 17: 5281
-
[46]
[46] Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, Konig B. Green Chem, 2009, 11: 1948
-
[47]
[47] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Angew Chem, Int Ed, 2010, 49: 2530
-
[48]
[48] Zhang Z H, Zhao Z B. Bioresour Technol, 2011, 102: 3970
-
[49]
[49] Li C Z, Zhang Z H, Zhao Z B K. Tetrahedron Lett, 2009, 50: 5403
-
[50]
[50] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746
-
[51]
[51] Chen T M, Lin L. Chin J Chem, 2010, 28: 1773
-
[52]
[52] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131
-
[53]
[53] Pagan-Torres Y J, Wang T F, Gallo J M R, Shanks B H, Dumesic J A. ACS Catal, 2012, 2: 930
-
[54]
[54] Nikolla E, Roman-Leshkov Y, Moliner M, Davis M E. ACS Catal, 2011, 1: 408
-
[55]
[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]
[56] Yasuda M, Nakamura Y, Matsumoto J, Yokoi H, Shiragami T. Bull Chem Soc Jpn, 2011, 84: 416
-
[57]
[57] Wang T F, Pagan-Torres Y J, Combs E J, Dumesic J A, Shanks B H. Top Catal, 2012, 55: 657
-
[58]
[58] Stahlberg T, Sorensen M G, Riisager A. Green Chem, 2010, 12: 321
-
[59]
[59] Takagaki A, Ohara M, Nishimura S, Ebitani K. Chem Commun, 2009: 6276
-
[60]
[60] Watanabe M, Aizawa Y, Iida T, Nishimura R, Inomata H. Appl Catal A, 2005, 295: 150
-
[61]
[61] Watanabe M, Aizawa Y, Iida T, Aida T M, Levy C, Sue K, Inomata H. Carbohydr Res, 2005, 340: 1925
-
[62]
[62] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558
-
[63]
[63] Huang R L, Qi W, Su R X, He Z M. Chem Commun, 2010, 46: 1115
-
[64]
[64] Stahlberg T, Rodriguez-Rodriguez S, Fristrup P, Riisager A. Chem-Eur J, 2011, 17: 1456
-
[65]
[65] Sheldon R. Chem Commun, 2001: 2399
-
[66]
[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]
[67] Zhang Z H, Zhao Z B K. Bioresour Technol, 2010, 101: 1111
-
[68]
[68] Zhang Z H, Zhao Z B K. Carbohydr Res, 2009, 344: 2069
-
[69]
[69] Li C Z, Wang Q, Zhao Z B K. Green Chem, 2008, 10: 177
-
[70]
[70] Li C Z, Zhao Z K B. Adv Synth Catal, 2007, 349: 1847
-
[71]
[71] Swatloski R P, Spear S K, Holbrey J D, Rogers R D. J Am Chem Soc, 2002, 124: 4974
-
[72]
[72] Rinaldi R, Palkovits R, Schuth F. Angew Chem, Int Ed, 2008, 47: 8047
-
[73]
[73] Su Y, Brown H M, Huang X, Zhou X-D, Amonette J E, Zhang Z C. Appl Catal A, 2009, 361: 117
-
[74]
[74] Qi X H, Watanabe M, Aida T M, Smith R L. Cellulose, 2011, 18: 1327
-
[75]
[75] Zhang Y T, Du H B, Qian X H, Chen E Y X. Energy Fuel, 2010, 24: 2410
-
[76]
[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]
[77] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979
-
[78]
[78] Haworth W N, Jones W G M. J Chem Soc, 1944: 667
-
[79]
[79] Antal M J, Mok W S L, Richards G N. Carbohydr Res, 1990, 199: 111
-
[80]
[80] Newth F H. Adv Carbohydr Chem, 1951, 6: 83
-
[81]
[81] Amarasekara A S, Williams L D, Ebede C C. Carbohydr Res, 2008, 343: 3021
-
[82]
[82] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Inorg Chem, 2010, 49: 10081
-
[83]
[83] Roman-Leshkov Y, Moliner M, Labinger J A, Davis M E. Angew Chem, Int Ed, 2010, 49: 8954
-
[84]
[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]
[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]
[86] Howarth O W, Morgan G G, Mckee V, Nelson J. J Chem Soc, Dalton Trans, 1999: 2097
-
[87]
[87] Richter D T, Lash T D. Tetrahedron Lett, 1999, 40: 6735
-
[88]
[88] Benahmed-Gasmi A S, Frere P, Jubault M, Gorgues A, Cousseau J, Garrigues B. Synth Met, 1993, 56: 1751
-
[89]
[89] Hui Z, Gandini A. Eur Polym J, 1992, 28: 1461
-
[90]
[90] Amarasekara A S, Green D, Williams L D. Eur Polym J, 2009, 45: 595
-
[91]
[91] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51
-
[92]
[92] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346
-
[93]
[93] Mehdi H, Bodor A, Lantos D, Horvath I T, De Vos D E, Binnemans K. J Org Chem, 2007, 72: 517
-
[94]
[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]
[95] Cottier L, Descotes G, Lewkowski J, Skowronski R, Viollet E. J Heterocycl Chem, 1995, 32: 927
-
[96]
[96] Sheldon R A. Stud Surf Sci Catal, 1991, 59: 33
-
[97]
[97] Van Deurzen M P J, Van Rantwijk F, Sheldon R A. J Carbohydr Chem, 1997, 16: 299
-
[98]
[98] Amarasekara A S, Green D, Mcmillan E. Catal Commun, 2008, 9: 286
-
[99]
[99] Verdeguer P, Merat N, Gaset A. J Mol Catal, 1993, 85: 327
-
[100]
[100] Partenheimer W, Grushin V V. Adv Synth Catal, 2001, 343: 102
-
[101]
[101] Moreau C, Durand R, Pourcheron C, Tichit D. Stud Surf Sci Catal, 1997, 108: 399
-
[102]
[102] Carlini C, Patrono P, Galletti A M R, Sbrana G, Zima V. Appl Catal A, 2005, 289: 197
-
[103]
[103] Navarro O C, Canos A C, Chornet S I. Top Catal, 2009, 52: 304
-
[1]
-
-
-
[1]
Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H3PW12O40 on Hydrogen Storage of MgH2. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
-
[2]
Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
-
[3]
Zhonghan Xu , Yuejia Li , Kin Shing Chan . 碳中和新旅程. University Chemistry, 2025, 40(6): 167-171. doi: 10.12461/PKU.DXHX202407075
-
[4]
Qianqian ZHU , Lihui XU , Hong PAN , Chengjian YAO , Hong ZHAO , Nan MA , Xiaolin SHI , Zihan SHEN , Weijun ZHANG , Zhongjian WANG . Waste cotton fabric-ased porous carbon materials: Preparation and wave-absorbing properties. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1555-1564. doi: 10.11862/CJIC.20250040
-
[5]
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
-
[6]
Xinlong XU , Chunxue JING , Yuzhen CHEN . Bimetallic MOF-74 and derivatives: Fabrication and efficient electrocatalytic biomass conversion. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1545-1554. doi: 10.11862/CJIC.20250046
-
[7]
Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
-
[8]
Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
-
[9]
Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
-
[10]
Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
-
[11]
Kuaibing Wang , Feifei Mao , Weihua Zhang , Bo Lv . Design and Practice of a Comprehensive Teaching Experiment for Preparing Biomass Carbon Dots from Rice Husk. University Chemistry, 2025, 40(5): 342-350. doi: 10.12461/PKU.DXHX202407042
-
[12]
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
-
[13]
Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
-
[14]
Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
-
[15]
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
-
[16]
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
-
[17]
Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
-
[18]
Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
-
[19]
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
-
[20]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(339)
- HTML views(11)