中文 |
English |
Email Alert
生物质基乙酰丙酸选择性还原制备新型平台化合物γ-戊内酯
Conversion of Biomass to Novel Platform Chemical γ-Valerolactone by Selective Reduction of Levulinic Acid
生物质是唯一能替代化石资源转化得到液体燃料及化学品的可再生资源,近年来,催化转化生物质制备各种平台化合物的研究受到了人们越来越广泛的关注。和乙酰丙酸(LA)一样,γ-戊内酯(GVL)也被认为是一种具有广泛应用潜能的新型生物质基平台化合物。目前,人们已经开发出多种催化剂和反应体系用于催化生物质基LA选择性还原制备GVL。根据氢源的不同可将LA制备GVL的途径概括为4种:分别以分子H2、甲酸(FA)、合成气和醇类作为氢源的途径。本文着重从氢源的差异来归纳和总结生物质基LA选择性还原制备GVL的途径及其研究进展,以期为寻找一种高效、经济、环保的GVL合成途径提供一些思路和参考。
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
乙酰丙酸
levulinic acid
[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-Pree 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] Miambres J F, Aramendía M A, Marinas A, Marinas J M, Urbano F J. J. Mol. Catal. A: Chem., 2011, 338: 121—129
/
| 〈 |
|
〉 |
PDF
(1036KB)
