生物质平台分子γ-戊内酯的研究进展
收稿日期: 2014-09-07
修回日期: 2014-11-09
网络出版日期: 2014-12-08
基金资助
国家重点基础研究发展计划(973计划, No. 2012CB215305)、国家自然科学基金(Nos. 21325208, 21172209)、教育部中央高校基本科研业务费(No. WK2060190025)、高等学校博士点基金(No. 20123402130008)和霍英东教育基金资助项目.
Recent Progress in the Studies of Biomass Platform Molecule γ-Velerolactone
Received date: 2014-09-07
Revised date: 2014-11-09
Online published: 2014-12-08
Supported by
Project supported by the National Basic Research Program of China (973 Program, No. 2012CB215305), the National Natural Science Foundation of China (Nos. 21325208, 21121172209), the Foundational Research Funds for the Central Universities (No. WK2060190025), the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20123402130008) and the Fok Ying Tung Education Foundation.
生物质是自然界存量丰富的可再生资源. 随着化石资源的日渐枯竭, 由生物质制备燃料和化学品引起人们关注. 把生物质转化为燃料和化学品通常经过生物质平台分子步骤. 在众多生物质平台分子中, γ-戊内酯(GVL)具有广泛的用途, 有关γ-戊内酯的合成和转化的研究成为一个热点课题. 由木质纤维素制备GVL已经开发出多种催化体系, 将GVL转化为燃料、化学品以及高分子材料也有大量文献报道. 着重从不同的原料、催化体系归纳GVL的合成路线和方法, 为探索高效、经济、绿色、可持续的GVL合成途径提供思路, 并对GVL的高效转化的研究加以总结, 为发展新的转化技术, 拓展应用范围提供参考.
杨珍 , 傅尧 , 郭庆祥 . 生物质平台分子γ-戊内酯的研究进展[J]. 有机化学, 2015 , 35(2) : 273 -283 . DOI: 10.6023/cjoc201409012
Lignocellulosic biomass is an abundant and renewable resource of carbon that allows the production of versatile and viable chemicals and fuels. Various processes have been developed for the conversion of biomass and its derivatives into platform molecules. Among these molecules, γ-valerolactone (GVL) is widely used because of its high stability, low toxicity and low volatility. GVL is an ideal precursor for the production of fuels and value-added chemicals. Up to now, various catalysts and reaction systems have been developed for the production of GVL from biomass, and many processes for the conversion GVL into fuels and chemicals have also been reported. In this paper, the different feedstocks including levulinic acid (LA), levulinate esters and other compounds for the production of GVL, as well as the catalytic systems including homogeneous and heterogeneous catalysts for the hydrogenation of LA to GVL using H2 gas or formic acid (FA) as hydrogen source are summarized. The conversion of GVL into fuels, chemicals and polymers is reviewed.
Key words： lignocellulosic biomass; γ-valerolactone; catalytic system; fuels; chemicals; polymers
[1] For insight into humanities relience on fossil resources for the manufacture of fuels and materials see: BP Energy Outlook 2030, http://www.bp.com/sectionbodycopy.do?categoryId=7500&content Id=7068481; http://www.plasticseurope.org/.
[2] (a) Tilman, D.; Socolow, R.; Foley, J. A.; Hill, J.; Larson, E.; Pacala, L. L. S.; Reilly, J.; Searchinger, T.; Somerville, C.; Williams, R. Science 2009, 325, 270.
(b) Wright, W. R. H.; Palkovits, R. ChemSusChem 2012, 5, 1657.
[3] Cheng, S.; Zhu, S. BioResources 2009, 4, 456.
[4] Wyman, C. E.; Dale, B. E.; Elander, R. T.; Holtzapple, M.; Ladisch, M. R.; Lee, Y. Y. Bioresour. Technol. 2005, 96, 1959.
[5] (a) Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
(b) Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044.
[6] (a) Huber, G. W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A. Science 2005, 308, 1446.
(b) Zhao, H. B.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Science 2007, 316, 1597.
(c) Leshkov, Y. R.; Chheda, J. N.; Dumesic, J. A. Science 2006, 312, 1933.
[7] (a) Yan, N.; Zhao, C.; Luo, C.; Dyson, P. J.; Liu, H. C.; Kou, Y. J. Am. Chem. Soc. 2006, 128, 8714.
(b) Hu, X.; Li, C. Z. Green Chem. 2011, 13, 1676.
(c) Leshkov, Y. R.; Barrett, C. J.; Liu, Z. Y.; Dumesic, J. A. Nature 2007, 447, 982.
(d) Thananatthanachon, T.; Rauchfuss, T. B. Angew. Chem., Int. Ed. 2010, 49, 6616.
[8] Melero, J. A.; Iglesias, J.; Garcia, A. Energy Environ. Sci. 2012, 5, 7393.
[9] (a) Serrano-Ruiz, J. C.; Luque, R.; Sepulveda-Escribano, A. Chem. Soc. Rev. 2011, 40, 5266.
(b) Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Green Chem. 2010, 12, 1493.
(c) Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538.
[10] Alonso, D. M.; Wettstein, S. G.; Dumesic, J. A. Green Chem. 2013, 15, 584.
[11] Horváth, I. T.; Mehdi, H.; Fabos, V.; Boda, L.; Mika, L. T. Green Chem. 2008, 10, 238.
[12] (a) Serrano-Ruiz, J. C.; Braden, D. J.; West, R. M.; Dumesic, J. A. Appl. Catal. B: Environ. 2010, 100, 184.
(b) Bond, J. Q.; Alonso, D. M.; Wang, D.; West, R. M.; Dumesic, J. A. Science 2010, 327, 1110.
(c) Lange, J. P.; Price, R.; Ayoub, P. M.; Louis, J.; Petrus, L.; Clarke, L.; Gosselink, H. Angew. Chem. 2010, 122, 4581.
(d) Palkovits, R. Angew. Chem., Int. Ed. 2010, 49, 4336.
[13] (a) Manzer, L. E. Appl. Catal. A: Gen. 2004, 272, 249.
(b) Ma, Z.; Hong, Y.; Nelson, D. M.; Pichamuthu, J. E.; Leeson, C. E.; Wagner, W. R. Biomacromolecules 2011, 12, 3265.
(c) Meulen, I. V.; Gubbels, E.; Huijser, S.; Sablong, R.; Koning, C. E.; Heise, A.; Duchateau, R. Macromolecules 2011, 44, 4301.
(d) Cerniauskaite, D.; Rousseau, J.; Sackus, A.; Rollin, P.; Tatibouet, A. Eur. J. Org. Chem. 2011, 2293.
(e) Guo, R.-H.; Zhang, Q.; Ma, Y.-B.; Huang, X.-Y.; Luo, J.; Wang, L.-J.; Geng, C.-A.; Zhan, X.-M.; Zhou, J.; Jiang, Z.-Y.; Chen, J.-J. Bioorg. Med. Chem. 2011, 19, 1400.
[14] (a) Jessop, P. G. Green Chem. 2011, 13, 1391.
(b) Fegyverneki, D.; Orha, L.; Horváth, I. T. Tetrahedron 2010, 66, 1078.
(c) Horváth, I. T. Green Chem. 2008, 10, 1024.
[15] (a) Christian, R. V.; Brown, H. D.; Hixon, R. M. J. Am. Chem. Soc. 1947, 69, 1961.
(b) Elliott, D. C.; Frye, J. G. US 5883266, 1999 [Chem. Abstr. 1999, 130, 211627].
[16] (a) Rose, M.; Palkovits, R. Macromol. Rapid Commun. 2011, 32, 1299.
[17] Osakada, K.; Yoshikawa, S.; Ikariya, T. J. Organomet. Chem. 1982, 231, 79.
[18] (a) Ohkkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509.
(b) Starodubtseva, E. V.; Ferapontov, V. A. Russ. Chem. Bull. 2005, 54, 2374.
[19] (a) Mehdi, H.; Bodor, A.; Tuba, R.; Horváth, I. T. Abstr. Papers Am. Chem. Soc. 2003, 226, U721.
(b) Delhomme, C.; Schaper, L. A. J. Organomet. Chem. 2013, 724, 297.
[20] Haan, R. J.; Lange, J.-P.; Petrus, L.; Petrus-Hoogenbosch, C. J. M. US 20070208183, 2007 [Chem. Abstr. 2007, 147, 323454].
[21] (a) Kawasaki, I.; Tsunoda, K.; Tsuji, T.; Yamaguchi, T.; Shibuta, H.; Uchida, N.; Yamashita, M.; Ohta, S. Chem. Commun. 2005, 2134.
(b) Cheung, F. K.; Clarke, A. J.; Clarkson, G. J.; Fox, D. J.; Graham, M. A.; Lin, C. X.; Crivill, A. L.; Wills, M. Dalton Trans. 2010, 39, 1395.
[22] (a) Mehdi, H.; Fabos, V.; Tuba, R.; Bodor, A.; Mika, L. T.; Horváth, I. T. Top. Catal. 2008, 48, 49.
(b) Tukacs, J. M.; Király, D.; Dibó, G. Green Chem. 2012, 14, 2057.
[23] Deng, L.; Li, J.; Lai, D.-M.; Fu, Y.; Guo, Q.-X. Angew. Chem., Int. Ed. 2009, 121, 6651.
[24] Chalid, M.; Broekhuis, A. A.; Heeres, H. J. J. Mol. Catal. A: Chem. 2011, 341, 14.
[25] Li, W.; Xie, J.-H.; Lin, H.; Zhou, Q.-L. Green Chem. 2012, 14, 2388.
[26] Deng, J.; Wang, Y.; Pan, T.; Xu, Q.; Guo, Q.-X.; Fu, Y. ChemSusChem 2013, 6, 1163.
[27] Dunlop, A. P.; Madden, J. W. US 2786852, 1957 [Chem. Abstr. 1957, 51, 48740].
[28] 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.
[29] Schuette, H. A.; Thomas, R. W. J. Am. Chem. Soc. 1930, 52, 3010.
[30] (a) Kyrides, L. P.; Craver, J. K. US 2368366, 1945 [Chem. Abstr. 1945, 39, 28552].
(b) Christian, R. V.; Brown, H. D.; Hixon, R. M. J. Am. Chem. Soc. 1947, 69, 1961.
[31] Broadbent, H. S.; Campbell, G. C.; Bartley, W. J.; Johnson, J. H. J. Org. Chem. 1959, 24, 1847.
[32] Manzer, L. E. Appl. Catal. A: Gen. 2004, 272, 249.
[33] Yan, Z.-P.; Lin, L.; Liu, S.-J. Energy Fuels 2009, 23, 3853.
[34] Primo, A.; Concepcion, P.; Corma, A. Chem. Commun. 2011, 47, 3613.
[35] Cervantes, C. O.; García, J. J. Inorg. Chim. Acta 2013, 397, 124.
[36] Du, X.-L.; Liu, Y.-M.; Wang, J.-Q.; Cao, Y.; Fan, K.-N. Chin. J. Catal. 2013, 34, 993.
[37] Yan, K.; Lafleur, T.; Wu, G.-S.; Liao, J.-Y.; Ceng, C.; Xie, X.-M. Appl. Catal. A: Gen. 2013, 468, 52.
[38] Serrano-Ruiz, J. C.; Wang. D.; Dumesic, J. A. Green Chem. 2010, 12, 574.
[39] Ayoub, P. M.; Lange, J. P. WO 2008142127, 2008 [Chem. Abstr. 2008, 150, 7250].
[40] Lange, J. P.; Price. R, Ayoub, P. M.; Louis, J.; Petrus, L.; Clarke, L.; Gosselink, H. Angew. Chem. 2010, 122, 4581.
[41] Skerget, M.; Knez, Z.; Knez-Hrncic, M. J. Chem. Eng. Data 2011, 56, 694.
[42] Han, X.; Poliakoff, M. Chem. Soc. Rev. 2012, 41, 1428.
[43] McHugh, M.; Krukonis, V. Supercritical Fluid Extraction Principle and Practice, Butterworth-Hernemann, Boston, 1994.
[44] Manzer, L. E.; Hutchenson, K. W. US 20040254384, 2004 [Chem. Abstr. 2004, 142, 38134].
[45] Lazzaroni, M. J.; Bush, D.; Jones, R.; Hallett, J. P.; Liotta, C. L.; Eckert, C. A. Fluid Phase Equilib. 2004, 224, 143.
[46] Bourne, R. A.; Stevens, J. G.; Ke, J.; Poliakoff, M. Chem. Commun. 2007, 4632.
[47] Deng, L.; Zhao, Y.; Li, J.; Fu, Y.; Liao, B.; Guo, Q.-X. ChemSusChem 2010, 3, 1172.
[48] (a) Du, X.-L.; He, L.; Zhao, S.; Liu, Y.-M.; Cao, Y.; He, H.-J.; Fan.; K.-N. Angew. Chem., Int. Ed. 2011, 50, 7815.
[49] Yuan, J.; Li, S.-S.; Yu, L.; Liu, Y.-M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Energy Environ. Sci. 2013, 6, 3308.
[50] Alonso, D. M.; Wettstein, S. G.; Bond, J. Q.; Root, T. W.; Dumesic, J. A. ChemSusChem 2011, 4, 1078.
[51] Yan, K.; Chen, A.-C. Fuel 2014, 115, 101.
[52] Kopetzki, D.; Antonietti, M. Green Chem. 2010, 12, 656.
[53] Xin, L.; Zhang, Z.-Y.; Qi, J.; Chadderdon, D. J.; Qiu, Y.; Warsko, K. M.; Li, W.-Z. ChemSusChem 2013, 6, 674.
[54] (a) Al-Shaal, M. G.; Wright, W. R. H.; Palkovits, R. Green Chem. 2012, 14, 1260.
(b) Saravanamurugan, S.; Riisager, A. Catal. Commun. 2012, 17, 71.
(c) Saravanamurugan, S.; Van Buu, O. N.; Riisager, A. ChemSusChem 2011, 4, 723.
[55] Gürbüz, E. I.; Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. ChemSusChem 2011, 4, 357.
[56] Du, X.-L.; Bi, Q.-Y.; Liu, Y.-M.; Cao, Y.; Fan, K.-N. ChemSusChem 2011, 4, 1838.
[57] Hengne, A. M.; Rode, C. V. Green Chem. 2012, 14, 1064.
[58] (a) Chuah, G. K.; Jaenicke, S.; Zhu, Y.-Z.; Liu, S.-H. Curr. Org. Chem. 2006, 10, 1639.
(b) Tang, X.; Sun, Y.; Zeng, X.; Hao, W.; Lin, L.; Liu, S. Energy Fuels 2014, 28, 4251.
(c) Tang, X.; Hu, L.; Sun, Y.; Lin, L. RSC Adv, 2013, 3, 10277.
(d) Wang, J.; Jaenicke, S.; Chuah, G. K. RSC Adv. 2014, 4, 13481.
[59] Chia, M.; Dumesic, J. A. Chem. Commun. 2011, 47, 12233.
[60] Yang, Z.; Huang, Y.-B, Guo, Q.-X.; Fu, Y. Chem. Commun. 2013, 49, 5328.
[61] Tang, X.; Chen, H.-W.; Hu, L.; Hao, W.-W.; Sun, Y.; Zeng, X.-H.; Lin, L.; Liu, S.-J. Appl. Catal. B: Environ. 2014, 147, 82.
[62] Heeres, H.; Handana, R.; Chunai, D.; Rasrendra, C. B.; Girisuta, B.; Heeres, H. J. Green Chem. 2009, 11, 1247.
[63] Alonso, D. M.; Gallo, J. M. R.; Mellmer, M. A.; Wettstein, S. G.; Dumesic, J. A. Catal. Sci. Technol. 2013, 3, 927.
[64] Hengne, A. M.; Kamble, S. B.; Rode, C. V. Green Chem. 2013, 15, 2540.
[65] Bui, L.; Luo, H.; Gunther, W. R.; Román-Leshkov, Y. Angew. Chem., Int. Ed. 2013, 52, 8022.
[66] Alonso, D. M.; Wettstein, S. G.; Mellmer, M. A.; Gurbuz, E. I.; Dumesic, J. A. Energy Environ. Sci. 2013, 6, 76.
[67] (a) Bereczky, Á.; Lukács, K.; Farkas, M.; Dóbé, S. Proceedings of the European Combustion Meeting, 2013, Paper P3-37. ISBN 978-91-637-2151-9. (b) Bruno, T. J.; Wolk, A.; Naydich, A. Energy Fuels 2010, 24, 2758.
[68] Dayma, G.; Halter, F.; Foucher, F.; Togbé, C.; Rousselle, C. M.; Dagaut, P. Energy Fuels 2012, 26, 4735.
[69] Ruiz, J. C. S.; Dumesic, J. A. Energy Environ. Sci. 2011, 4, 83.
[70] Duan, Z.Q.; Hu, F. Green Chem. 2012, 14, 1581.
[71] Gürbüz, E. I.; Gallo, J. M. R.; Alonso, D. M.; Wettstein, S. G.; Lim, W. Y.; Dumesic, J. A. Angew. Chem., Int. Ed. 2013, 52, 1270.
[72] Strádi, A.; Molnár, M.; Óvári, M.; Dibó, G.; Richterb, F. U.; Mika.; L. T. Green Chem. 2013, 15, 1857.
[73] (a) Balat, M. Energy Sources 2005, 27, 569.
(b) Pagliaro, M.; Ciriminna, R.; Kimura, H.; Rossi, M.; Pina, C. D. Angew. Chem., Int. Ed. 2007, 46, 4434.
[74] (a) Kar, Y.; Deveci, H. Energy Sources 2006, 28, 909.
(b) Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044.
(c) Alternative Fuel Transportation Program (DOE) (1998) P-series fuels (Proposed Rules). Fed Regist 63:40202. (d) Paul, S. F. WO 9743356, 1997 [Chem. Abstr. 1997, 128, 63757].
[75] (a) Geilen, F. M. A.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
(b) Du, X.-L.; Bi, Q.-Y.; Liu, Y.-M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Green Chem. 2012, 14, 935.
(c) Upare, P. P.; Lee, J.- M.; Hwang, Y. K.; Hwang, D. W.; Lee, J.-H.; Halligudi, S. B.; Hwang, J. S.; Chang, J.-S. ChemSusChem 2011, 4, 1.
(d) Al-Shaal, M. G.; Dzierbinski, A.; Palkovits, R. Green Chem. 2014, 16, 1358.
[76] Zhao, Y.; Fu, Y.; Guo, Q.-X. Bioresour. Technol. 2012, 114, 740.
[77] Dai, J.-J.; Huang, Y.-B.; Fang, C.; Guo, Q.-X.; Fu, Y. ChemSusChem 2012, 5,617.
[78] (a) Manzer, L. E. Appl. Catal. A 2004, 272, 249.
(b) Manzer, L. E. WO 2004007421, 2004 [Chem. Abstr. 2004, 140, 128809].
[79] (a) Beller, M.; Tafesh, A. M. In Applied Homogeneous Catalysis with Organometallic Compounds, Eds.: Cornils, B.; Herrmann, W. A., VCH, Weinheim, 1996, p. 187.
(b) Drent, E.; Ernst, R.; Jager, W. W.; Krom, C. A. WO 2006084890, 2006 [Chem. Abstr. 2006, 145, 210643].
[80] Lange, J. P.; Vestering, J. Z.; Haan, R. J. Chem. Commun. 2007, 3488.
[81] Zeng, F.-X.; Liu, H.-F.; Deng, L.; Liao, B.; Pang, H.; Guo, Q.-X. ChemSusChem 2013, 6, 600.
[82] (a) Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508.
(b) Gu,Y.-L.; Zhang, J.; Duan, Z.-Y.; Deng, Y.-Q. Adv. Synth. Catal. 2005, 347, 512.
[83] Chalid, M.; Heeres, H. J.; Broekhuis, A. A. J. Appl. Polym. Sci. 2012, 123, 3556.
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