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Progress in Chemistry 2013, Vol. 25 Issue (11): 1906-1914 DOI: 10.7536/PC130332 Previous Articles   Next Articles

• Review •

Conversion of Biomass to Novel Platform Chemical γ-Valerolactone by Selective Reduction of Levulinic Acid

Tang Xing, Hu Lei, Sun Yong*, Zeng Xianhai, Lin Lu*   

  1. School of Energy Research, Xiamen University, Xiamen 361005, China
  • Received: Revised: Online: Published:
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Biomass is the only renewable resources on the earth that can be converted to liquid fuels and chemicals to replace fossil resources. Recently, the catalytic conversion of biomass to platform molecules has attracted more and more attentions from the researchers worldwide. γ-Valerolactone (GVL) is regarded as a platform molecule that has extensive application potential, similar to levulinic acid (LA). Up to now, various of catalysts and reaction systems were developed and applied to the selective reduction of biomass-derived LA to GVL, and the hydrogenation of LA can be driven by various hydrogen sources, including molecule H2, formic acid (FA), syngas and alcohols. In this review, the catalytic hydrogenation routes and recent research progress for the reduction of LA are systematically summarized in view of the diversity of hydrogen sources. The future research trends of the selective reduction of LA to GVL are suggested.

Contents
1 Introduction
2 Catalytic hydrogenation mechanism of LA to GVL
3 Production of GVL using external molecule H2 as a hydrogen source
3.1 Heterogeneous catalytic systems
3.2 Homogeneous catalytic systems
4 Production of GVL using FA as a hydrogen source
5 Production of GVL using syngas as a hydrogen source
6 Production of GVL using alcohols as a hydrogen donor
7 Conclusion and outlook

Key words: levulinic acid, γ-valerolactone, catalytic hydrogenation, biomass, platform chemicals

CLC Number: 

[1] 袁振宏 (Yuan Z H), 罗文 (Luo W), 吕鹏梅 (Lv P M), 王忠铭 (Wang Z M), 李惠文 (Li H W). 化工进展 (Chemical Industry and Engineering Progress), 2009, 28 (10): 1687—1692
[2] Field C B, Campbell J E, Lobell D B. Trends Ecol. Evol., 2008, 23: 65—72
[3] 方向晨 (Fang X C). 化工进展 (Chemical Industry and Engineering Progress), 2011, 30 (11): 2333—2339
[4] Fischer G, Schrattenholzer L. Biomass Bioenergy, 2001, 20: 151—159
[5] Huber G W, Iborra S, Corma A. Chem. Rev., 2006, 106: 4044—4098
[6] Corma A, Iborra S, Velty A. Chem. Rev., 2007, 107: 2411—2502
[7] 林鹿 (Lin L), 何北海 (He B H), 孙润仓 (Sun R C), 胡若飞 (Hu R F). 化学进展 (Progress in Chemistry), 2007, 19 (7/8): 1206—1216
[8] 王泽 (Wang Z), 林伟刚 (Lin W G), 宋文立 (Song W L), 姚建中 (Yao J Z), 鲁长波 (Lu C B), 都林 (Du L). 化学进展 (Progress in Chemistry), 2007, 19 (7/8): 1190—1197
[9] 余强 (Yu Q), 庄新姝 (Zhuang X S), 袁振宏 (Yuan Z H), 亓伟 (Qi W), 王琼 (Wang Q), 谭雪松 (Tan X S), 许敬亮 (Xu J L), 张宇 (Zhang Y), 徐慧娟 (Xu H J), 马隆龙 (Ma L L). 化工进展 (Chemical Industry and Engineering Progress), 2012, 31 (4): 784—791
[10] Rackemann D W, Doherty W O S. Biofuels, Bioprod. Biorefin., 2011, 5: 198—214
[11] 彭红 (Peng H), 刘玉环 (Liu Y H), 张锦胜 (Zhang J S), 阮榕生 (Ruan R S). 化工进展 (Chemical Industry and Engineering Progress), 2009, 28 (12): 2237—2241
[12] 彭林才 (Peng L C), 林鹿 (Lin L), 李辉 (Li H). 化学进展 (Progress in Chemistry), 2012, 24 (5): 801—809
[13] Hu L, Zhao G, Hao W, Tang X, Sun Y, Lin L, Liu S J. RSC Advances, 2012, 2: 11184—11206
[14] 胡磊 (Hu L), 孙勇 (Sun Y), 林鹿 (Lin L). 化学进展 (Progress in Chemistry), 2012, 24 (4): 483—491
[15] Horváth I T, Mehdi H, Fábos V, Boda L, Mika L T. Green Chem., 2008, 10: 238—242
[16] Kamm B. Angew. Chem. Int. Ed., 2007, 46: 5056—5058
[17] Oser B L, Carson S, Oser M. Food Cosmet. Toxicol., 1965, 3: 563—569
[18] Cannon G W, Casler J J Jr, Gaines W A. J. Org. Chem., 1952, 17: 1245—1251
[19] Bond J Q, Alonso D M, West R M, Dumesic J A. Langmuir, 2010, 26: 16291-16298
[20] Fegyverneki D, Orha L, Láng G, Horváth I T. Tetrahedron, 2010, 66: 1078—1081
[21] Chalid M, Heeres H J, Broekhuis A A. J. Appl. Polym. Sci., 2012, 123: 3556—3564
[22] Bruno T J, Wolk A, Naydich A. Energy Fuels, 2010, 24: 2758—2767
[23] Alonso D M, Bond J Q, Serrano-Ruiz J C, Dumesic J A. Green Chem., 2010, 12: 992—999
[24] Bond J Q, Alonso D M, Wang D, West R M, Dumesic J A. Science, 2010, 327: 1110—1114
[25] Mosby W L. J. Am. Chem. Soc., 1952, 74: 2564—2569
[26] Mosby W L. J. Org. Chem., 1953, 18: 964—970
[27] Mosby W L. J. Org. Chem., 1954, 19: 294—304
[28] Lee C W, Urakawa R, Kimura Y. Eur. Polym. J., 1998, 34: 117—122
[29] Manzer L E. Appl. Catal. A, 2004, 272: 249—256
[30] Lange J P, Vestering J Z, Haan R J. Chem. Commun., 2007, 3488—3490
[31] Schuette H A, Thomas R W. J. Am. Chem. Soc., 1930, 52: 3010—3012
[32] Kyrides L P, Craver J K. US 2368366, 1945
[33] Christian R V Jr, Brown H D, Hixon R M. J. Am. Chem. Soc., 1947, 69: 1961—1963
[34] Dunlop A P, Madden J W. US 2786852, 1957
[35] Broadbent H S, Campbell G C, Bartley W J, Johnson J H. J. Org. Chem., 1959, 24: 1847—1854
[36] Yan Z P, Lin L, Liu S. Energy Fuels, 2009, 23: 3853—3858
[37] Al-Shaal M G, Wright W R H, Palkovits R. Green Chem., 2012, 14: 1260—1263
[38] Primo A, Concepcion P, Corma A. Chem. Commun., 2011, 47: 3613—3615
[39] Ortiz-Cervantes C, García J J. Inorg. Chim. Acta, 2013, 397: 124—128
[40] Raspolli-Galletti A M, Antonetti C, De Luise V, Martinelli M. Green Chem., 2012, 14: 688—694
[41] Raspolli-Galletti A M, Antonetti C, Ribechini E, Colombini M P, Di Nasso N D O, Bonari E. Appl. Energy, 2013, 102: 157—162
[42] Hengne A M, Rode C V. Green Chem., 2012, 14: 1064—1072
[43] Heeres H, Handana R, Chunai D, Borromeus R C, Girisuta B, Heeres H J. Green Chem., 2009, 11: 1247—1255
[44] Bourne R A, Stevens J G, Ke J, Poliakoff M. Chem. Commun., 2007, 4632—4634
[45] Selva M, Gottardo M, Perosa A. ACS Sustainable Chem. Eng., 2013, 1: 180—189
[46] Alonso D M, Wettstein S G, Bond J Q, Root T W, Dumesic J A. ChemSusChem, 2011, 4: 1078—1081
[47] Wettstein S G, Bond J Q, Alonso D M, Pham H N, Datye A K, Dumesic J A. Appl. Catal. B, 2012, 117/118: 321—329
[48] Azadi P, Carrasquillo-Flores R, Pagán-Torres Y J, Gürbüz E I, Farnood R, Dumesic J A. Green Chem., 2012, 14: 1573—1576
[49] Upare P P, Lee J M, Hwang D W, Halligudi S B, Hwang Y K, Chang J S. J. Ind. Eng. Chem., 2011, 17: 287—292
[50] Braca G, Galletti A M R, Sbrana G. J. Organomet. Chem., 1991, 417: 41—49
[51] Starodubtseva E V, Turova O V, Vinogradov M G, Gorshkova L S, Ferapontov V A. Russ. Chem. Bull., 2005, 54: 2374—2378
[52] Mehdi H, Fábos V, Tuba R, Bodor A, Mika L T, Horváth I T. Top. Catal., 2008, 48: 49—54
[53] Delhomme C, Schaper L A, Zhang-Pree M, Raudaschl-Sieber G, Weuster-Botz D, Kühn F E. J. Organomet. Chem., 2013, 724: 297—299
[54] Tukacs J M, Király D, Strádi A, Novodárszki G, Eke Z, Dibó G, Kégl T, Mika L T. Green Chem., 2012, 14: 2057—2065
[55] Chalid M, Broekhuis A A, Heeres H J. J. Mol. Catal. A: Chem., 2011, 341: 14—21
[56] Li W, Xie J H, Lin H, Zhou Q L. Green Chem., 2012, 14: 2388—2390
[57] Laurenczy G, Grasemann M. Energy Environ. Sci., 2012, 5: 8171—8181
[58] Johnson T C, Morris D J, Wills M. Chem. Soc. Rev., 2010, 39: 81—88
[59] Gu X, Lu Z H, Jiang H L, Akita T, Xu Q. J. Am. Chem. Soc., 2011, 133: 11822—11825
[60] Girisuta B, Janssen L P B M, Heeres H J. Chem. Eng. Res. Des., 2006, 84: 339—349
[61] Weingarten R, Cho J, Xing R, Conner W C, Huber G W. ChemSusChem, 2012, 5: 1280—1290
[62] Deng L, Li J, Lai D M, Fu Y, Guo Q X. Angew. Chem. Int. Ed., 2009, 48: 6529—6532
[63] Du X L, He L, Zhao S, Liu Y M, Cao Y, He H Y, Fan K N. Angew. Chem. Int. Ed., 2011, 50: 7815—7819
[64] Deng L, Zhao Y, Li J, Fu Y, Liao B, Guo Q X. ChemSusChem, 2010, 3: 1172—1175
[65] Stratakis M, Garcia H. Chem. Rev., 2012, 112: 4469—4506
[66] Zhang Y, Cui X, Shi F, Deng Y. Chem. Rev., 2012, 112: 2467—2505
[67] Bi Q Y, Du X L, Liu Y M, Cao Y, He H Y, Fan K N. J. Am. Chem. Soc., 2012, 134: 8926—8933
[68] Du X L, Bi Q Y, Liu Y M, Cao Y, Fan K N. ChemSusChem, 2011, 4: 1838—1843
[69] Yu L, Du X L, Yuan J, Liu Y M, Cao Y, He H Y, Fan K N. ChemSusChem, 2013, 6: 42—46
[70] Kopetzki D, Antonietti M. Green Chem., 2010, 12: 656—660
[71] Pagliaro M, Ciriminna R, Kimura H, Rossi M, Pina C D. Angew. Chem. Int. Ed., 2007, 46: 4434—4440
[72] Yung M M, Jablonski W S, Magrini-Bair K A. Energy Fuels, 2009, 23: 1874—1887
[73] Ruiz J R, Jiménez-Sanchidrián C. Cur. Org. Chem., 2007, 11: 1113—1125
[74] Graauw C F D, Peters J A, Bekkum H V, Huskens J. Synthesis, 1994, 10: 1007—1017
[75] Chia M, Dumesic J A. Chem. Commun., 2011, 47: 12233—12235
[76] Tanabe K, Yamaguchi T. Catal. Today, 1994, 20: 185—198
[77] Liu S H, Jaenicke S, Chuah G K. J. Catal., 2002, 206: 321—330
[78] Zhu Y. J. Catal., 2003, 218: 396—404
[79] Zhu Y, Liu S, Jaenicke S, Chuah G. Catal. Today, 2004, 97: 249—255
[80] Miambres J F, Aramendía M A, Marinas A, Marinas J M, Urbano F J. J. Mol. Catal. A: Chem., 2011, 338: 121—129
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