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 shu

Advances in selective catalytic transformation of ployols to value-added chemicals

MA Jiping ^a ,
YU Weiqiang ^a ,
WANG Min ^a ,
JIA Xiuquan ^a,b ,
LU Fang ^a ,
XU Jie ^a,,

1.
a Dalian National Laboratory for Clean Energy, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: XU Jie,
Received Date: 2 November 2012
Available Online: 14 December 2012
Fund Project: 国家自然科学基金(21233008, 21203183和21103174). (21233008, 21203183和21103174)

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.
- Biomass,
- Catalysis,
- Furan derivative,
- Polyol,
- Renewable resource
1. [1]
  [1] Gallezot P. Chem Soc Rev, 2012, 41: 1538
2. [2]
  [2] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588
3. [3]
  [3] Corma A, Iborra S, Velty A. Chem Rev, 2007, 107: 2411
4. [4]
  [4] Serrano-Ruiz J C, Luque R, Sepulveda-Escribano A. Chem Soc Rev, 2011, 40: 5266
5. [5]
  [5] Song Q, Wang F, Xu J. Chem Commun, 2012, 48: 7019
6. [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]
  [7] Ma H, Nie X, Cai J Y, Chen C, Gao J, Miao H, Xu J. Sci ChinaChem, 2010, 53: 1497
8. [8]
  [8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554
9. [9]
  [9] Wang F, Xu J, Dubois J L, Ueda W. ChemSusChem, 2010, 3: 1383
10. [10]
  [10] Liu J X, Du Z T, Yang Y L, Lu T L, Lu F, Xu J. ChemSusChem, 2012, 5: 2151
11. [11]
  [11] Shuttleworth P, Budarin V, Gronnow M, Clark J H, Luque R. J Nat Gas Chem, 2012, 21: 270
12. [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]
  [13] Yang P F, Kobayashi H, Fukuoka A. Chin J Catal(催化学报), 2011, 32: 716
14. [14]
  [14] Zhang Y M, Degirmenci V, Li C, Hensen E J M. ChemSusChem, 2011, 4: 59
15. [15]
  [15] Zhang J, Wu S B, Li B, Zhang H D. ChemCatChem, 2012, 4: 1230
16. [16]
  [16] Roman-Leshkov Y, Barrett C J, Liu Z Y, Dumesic J A. Nature, 2007, 447: 982
17. [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]
  [18] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754
19. [19]
  [19] Tong X L, Ma Y, Li Y D. Appl Catal A, 2010, 385: 1
20. [20]
  [20] Lewkowski J. Arkivoc, 2001, 2: 17
21. [21]
  [21] Shimizu K, Satsuma A. Energy Environ Sci, 2011, 4: 3140
22. [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [31] Yang F L, Liu Q S, Yue M, Bai X F, Du Y G. Chem Commun, 2011, 47: 4469
32. [32]
  [32] Bicker M, Kaiser D, Ott L, Vogel H. J Supercrit Fluid, 2005, 36: 118
33. [33]
  [33] Moreau C, Finiels A, Vanoye L. J Mol Catal A, 2006, 253: 165
34. [34]
  [34] Li C Z, Zhao Z K, Wang A Q, Zheng M Y, Zhang T. Carbohydr Res, 2010, 345: 1846
35. [35]
  [35] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2009, 11: 1327
36. [36]
  [36] Lai D M, Deng L, Li J A, Liao B, Guo Q X, Fu Y. ChemSusChem, 2011, 4: 55
37. [37]
  [37] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933
38. [38]
  [38] Roman-Leshkov Y, Dumesic J A. Top Catal, 2009, 52: 297
39. [39]
  [39] Shimizu K, Uozumi R, Satsuma A. Catal Commun, 2009, 10: 1849
40. [40]
  [40] Tuercke T, Panic S, Loebbecke S. Chem Eng Technol, 2009, 32: 1815
41. [41]
  [41] Qi X H, Watanabe M, Aida T M, Smith R L. Green Chem, 2008, 10: 799
42. [42]
  [42] Li C Z, Zhao Z B K, Cai H L, Wang A Q, Zhang T. Biomass Bioenerg, 2011, 35: 2013
43. [43]
  [43] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597
44. [44]
  [44] Yong G, Zhang Y G, Ying J Y. Angew Chem, Int Ed, 2008, 47: 9345
45. [45]
  [45] Zhang Y M, Pidko E A, Hensen E J M. Chem-Eur J, 2011, 17: 5281
46. [46]
  [46] Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, Konig B. Green Chem, 2009, 11: 1948
47. [47]
  [47] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Angew Chem, Int Ed, 2010, 49: 2530
48. [48]
  [48] Zhang Z H, Zhao Z B. Bioresour Technol, 2011, 102: 3970
49. [49]
  [49] Li C Z, Zhang Z H, Zhao Z B K. Tetrahedron Lett, 2009, 50: 5403
50. [50]
  [50] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746
51. [51]
  [51] Chen T M, Lin L. Chin J Chem, 2010, 28: 1773
52. [52]
  [52] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131
53. [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]
  [54] Nikolla E, Roman-Leshkov Y, Moliner M, Davis M E. ACS Catal, 2011, 1: 408
55. [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]
  [56] Yasuda M, Nakamura Y, Matsumoto J, Yokoi H, Shiragami T. Bull Chem Soc Jpn, 2011, 84: 416
57. [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]
  [58] Stahlberg T, Sorensen M G, Riisager A. Green Chem, 2010, 12: 321
59. [59]
  [59] Takagaki A, Ohara M, Nishimura S, Ebitani K. Chem Commun, 2009: 6276
60. [60]
  [60] Watanabe M, Aizawa Y, Iida T, Nishimura R, Inomata H. Appl Catal A, 2005, 295: 150
61. [61]
  [61] Watanabe M, Aizawa Y, Iida T, Aida T M, Levy C, Sue K, Inomata H. Carbohydr Res, 2005, 340: 1925
62. [62]
  [62] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558
63. [63]
  [63] Huang R L, Qi W, Su R X, He Z M. Chem Commun, 2010, 46: 1115
64. [64]
  [64] Stahlberg T, Rodriguez-Rodriguez S, Fristrup P, Riisager A. Chem-Eur J, 2011, 17: 1456
65. [65]
  [65] Sheldon R. Chem Commun, 2001: 2399
66. [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]
  [67] Zhang Z H, Zhao Z B K. Bioresour Technol, 2010, 101: 1111
68. [68]
  [68] Zhang Z H, Zhao Z B K. Carbohydr Res, 2009, 344: 2069
69. [69]
  [69] Li C Z, Wang Q, Zhao Z B K. Green Chem, 2008, 10: 177
70. [70]
  [70] Li C Z, Zhao Z K B. Adv Synth Catal, 2007, 349: 1847
71. [71]
  [71] Swatloski R P, Spear S K, Holbrey J D, Rogers R D. J Am Chem Soc, 2002, 124: 4974
72. [72]
  [72] Rinaldi R, Palkovits R, Schuth F. Angew Chem, Int Ed, 2008, 47: 8047
73. [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]
  [74] Qi X H, Watanabe M, Aida T M, Smith R L. Cellulose, 2011, 18: 1327
75. [75]
  [75] Zhang Y T, Du H B, Qian X H, Chen E Y X. Energy Fuel, 2010, 24: 2410
76. [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]
  [77] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979
78. [78]
  [78] Haworth W N, Jones W G M. J Chem Soc, 1944: 667
79. [79]
  [79] Antal M J, Mok W S L, Richards G N. Carbohydr Res, 1990, 199: 111
80. [80]
  [80] Newth F H. Adv Carbohydr Chem, 1951, 6: 83
81. [81]
  [81] Amarasekara A S, Williams L D, Ebede C C. Carbohydr Res, 2008, 343: 3021
82. [82]
  [82] Pidko E A, Degirmenci V, Van Santen R A, Hensen E J M. Inorg Chem, 2010, 49: 10081
83. [83]
  [83] Roman-Leshkov Y, Moliner M, Labinger J A, Davis M E. Angew Chem, Int Ed, 2010, 49: 8954
84. [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]
  [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]
  [86] Howarth O W, Morgan G G, Mckee V, Nelson J. J Chem Soc, Dalton Trans, 1999: 2097
87. [87]
  [87] Richter D T, Lash T D. Tetrahedron Lett, 1999, 40: 6735
88. [88]
  [88] Benahmed-Gasmi A S, Frere P, Jubault M, Gorgues A, Cousseau J, Garrigues B. Synth Met, 1993, 56: 1751
89. [89]
  [89] Hui Z, Gandini A. Eur Polym J, 1992, 28: 1461
90. [90]
  [90] Amarasekara A S, Green D, Williams L D. Eur Polym J, 2009, 45: 595
91. [91]
  [91] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51
92. [92]
  [92] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346
93. [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]
  [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]
  [95] Cottier L, Descotes G, Lewkowski J, Skowronski R, Viollet E. J Heterocycl Chem, 1995, 32: 927
96. [96]
  [96] Sheldon R A. Stud Surf Sci Catal, 1991, 59: 33
97. [97]
  [97] Van Deurzen M P J, Van Rantwijk F, Sheldon R A. J Carbohydr Chem, 1997, 16: 299
98. [98]
  [98] Amarasekara A S, Green D, Mcmillan E. Catal Commun, 2008, 9: 286
99. [99]
  [99] Verdeguer P, Merat N, Gaset A. J Mol Catal, 1993, 85: 327
100. [100]
  [100] Partenheimer W, Grushin V V. Adv Synth Catal, 2001, 343: 102
101. [101]
  [101] Moreau C, Durand R, Pourcheron C, Tichit D. Stud Surf Sci Catal, 1997, 108: 399
102. [102]
  [102] Carlini C, Patrono P, Galletti A M R, Sbrana G, Zima V. Appl Catal A, 2005, 289: 197
103. [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 . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
14. [14]
  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
15. [15]
  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
16. [16]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
17. [17]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
18. [18]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
19. [19]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
20. [20]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(303)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142