Renewable N-Heterocycles Production by Thermocatalytic Conversion and Ammonization of Biomass over ZSM-5

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 11, 2015, Pages 2890-2899

  Xu, Lujiang ^a   Yao, Qian ^a   Deng, Jin ^a   Han, Zheng ^a   Zhang, Ying ^a   Fu, Yao ^a   Huber, George W ^b   Guo, Qingxiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Wisconsin Electric Machines and Power Electronics Consortium   (United States)

Author keywords

Biomass; N Heterocycles; Reaction pathway; Thermocatalytic conversion and ammonization; Zeolites

Indexed keywords

AGRICULTURAL CHEMICALS; CELLULOSE; CHEMICAL INDUSTRY; CRUDE OIL; FUNCTIONAL MATERIALS; INDUSTRIAL CHEMICALS; PYRIDINE; ZEOLITES;

BIOMASS PRE TREATMENTS; CHEMICAL CONVERSIONS; ENVIRONMENTAL PROBLEMS; N-HETEROCYCLES; REACTION CONDITIONS; REACTION PATHWAYS; THERMOCATALYTIC CONVERSION AND AMMONIZATION; VALUE ADDED PRODUCTS;

BIOMASS;

BIOMASS; CHITOSAN; FOSSIL FUELS; FUNCTIONAL GROUPS; PRETREATMENT; RENEWABLE RESOURCES; SUSTAINABLE FOREST MANAGEMENT; SYNTHESIS;

EID: 84946426465     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00841     Document Type: Article

References (57)

1. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. The path forward for biofuels and biomaterials Science 2006, 311, 484-489 10.1126/science.1114736
2. Luterbacher, J. S.; Alonsoa, M. D.; Dumesic, J. A. Targeted chemical upgrading of lignocellulosic biomass to platform molecules Green Chem. 2014, 16, 4816-4838 10.1039/C4GC01160K
3. Zhou, C. H.; Xia, X.; Lin, C. X.; Tong, D. S.; Beltramini, J. Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels Chem. Soc. Rev. 2011, 40, 5588-5617 10.1039/c1cs15124j
4. Huber, G. W.; Iborra, S.; Corma, A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering Chem. Rev. 2006, 106, 4044-4098 10.1021/cr068360d
5. Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings Chem. Rev. 2014, 114, 2942-2977 10.1021/cr300122t
6. Nakamura, I.; Yamamoto, Y. Transition-metal-catalyzed reactions in heterocyclic synthesis Chem. Rev. 2004, 104, 2127-2198 10.1021/cr020095i
7. Stephen, A. L. Amines: Synthesis, Properties and Applications; Cambridge University Press, 2006.
8. Arpe, H.; Hawkins, S. Industrial Organic Chemistry, 5 th ed.; Wiley-VCH Press, 2010.
9. Soetaert, W.; Vandamme, E. J. Industrial Biotechnology: Sustainable Growth and Economic Success; Wiley-VCH Press, 2010.
10. Richard, A.; Jones, R. A. The Chemistry of Heterocyclic Compounds, pyrroles; Wiley-VCH Press, 2008.
11. Lee, S. Y.; Papoutsakis, E. T. Metabolic Engineering; Marcel Dekker Inc, 1999.
12. Bishop, R. B.; Denton, W. I. Production of pyrrole. US Patent 2478452, 1949.
13. Reddy, K. S. K.; Srinivasakannan, C.; Raghavan, K. V. Catalytic Vapor Phase Pyridine Synthesis: A Process Review Catal. Surv. Asia 2012, 16, 28-35 10.1007/s10563-011-9129-5
14. Shimizu, S.; Abe, N.; Iguchi, A.; Dohba, M.; Sato, H.; Hirose, K. I. Synthesis of pyridine bases on zeolite catalyst Microporous Mesoporous Mater. 1998, 21, 447-451 10.1016/S1387-1811(98)00052-3
15. Campanati, M.; Franceschini, S.; Piccolo, O.; Vaccari, A. Reaction pathway in the vapour-phase synthesis of indole and alkylindoles J. Catal. 2005, 232, 1-9 10.1016/j.jcat.2005.02.014
16. Shimizu, S.; Abe, N.; Iguchi, A.; Sato, H. Synthesis of pyridine bases: general methods and recent advances in gas phase synthesis over ZSM-5 zeolite Catal. Surv. Jpn. 1998, 2, 71-76 10.1023/A:1019057820543
17. Shiri, M. Indoles in multicomponent processes (MCPs) Chem. Rev. 2012, 112, 3508-3549 10.1021/cr2003954
18. Humphrey, G. R.; Kuethe, J. T. Practical methodologies for the synthesis of indoles Chem. Rev. 2006, 106, 2875-2911 10.1021/cr0505270
19. Inman, M.; Moody, C. J. Indole synthesis-something old, something new Chem. Sci. 2013, 4, 29-41 10.1039/C2SC21185H
20. Higashio, C. J.; Shoji, T. Heterocyclic compounds such as pyrrole, pyridines, pyrrolidine, piperidine, indole, imidazol and pyrazines Appl. Catal., A 2004, 260, 251-259 10.1016/S0926-860X(03)00197-2
21. Xu, L. J.; Jiang, Y. Y.; Yao, Q.; Han, Z.; Zhang, Y.; Fu, Y.; Huber, G. W.; Guo, Q. X. Direct production of indoles via thermo-catalytic conversion of bio-derived furans with ammonia over zeolites Green Chem. 2015, 17, 1281-1290 10.1039/C4GC02250E
22. Yao, Q.; Xu, L. J.; Han, Z.; Zhang, Y. Production of indoles via thermo-catalytic conversion and ammonization of bio-derived furfural Chem. Eng. J. 2015, 280, 74-81 10.1016/j.cej.2015.05.094
23. Xu, L. J.; Han, Z.; Yao, Q.; Zhang, Y.; Fu, Y.; Guo, Q. X. Towards the sustainable production of pyridines via thermo-catalytic conversion of glycerol with ammonia over zeolite catalysts Green Chem. 2015, 17, 2426-2435 10.1039/C4GC02235A
24. Bridgwater, A. V.; Peacocke, G. V. C. Fast pyrolysis processes for biomass Renewable Sustainable Energy Rev. 2000, 4, 1-73 10.1016/S1364-0321(99)00007-6
25. Anand, R.; Hegde, S. G.; Rao, B. S.; Gopinath, C. S. Catalytic synthesis of 2-methyl pyrazine over Zn-modified zeolites Catal. Lett. 2002, 84, 265-272 10.1023/A:1021400624969
26. 2 Res. Chem. Intermed. 2012, 38, 1743-1750 10.1007/s11164-012-0499-8
27. Vitolo, S.; Bresci, B.; Seggiani, M.; Gallo, M. G. Catalytic upgrading of pyrolytic oils over HZSM-5 zeolite: behaviour of the catalyst when used in repeated upgrading-regenerating cycles Fuel 2001, 80, 17-26 10.1016/S0016-2361(00)00063-6
28. Murata, K.; Liu, Y.; Inaba, M.; Takahara, I. Catalytic fast pyrolysis of jatropha wastes J. Anal. Appl. Pyrolysis 2012, 94, 75-82 10.1016/j.jaap.2011.11.008
29. Li, X.; Su, L.; Wang, Y.; Yu, Y.; Wang, C.; Li, X.; Wang, Z. Catalytic fast pyrolysis of Kraft lignin with HZSM-5 zeolite for producing aromatic hydrocarbons Front. Environ. Sci. Eng. 2012, 6, 295-303 10.1007/s11783-012-0410-2
30. Foster, A. J.; Jae, J.; Cheng, Y. T.; Huber, G. W.; Lobo, R. F. Optimizing the aromatic yield and distribution from catalytic fast pyrolysis of biomass over ZSM-5 Appl. Catal., A 2012, 423, 154-161 10.1016/j.apcata.2012.02.030
31. Lu, Q.; Yang, X. C.; Dong, C. Q.; Zhang, Z. F.; Zhang, X. M.; Zhu, X. F. Influence of pyrolysis temperature and time on the cellulose fast pyrolysis products: Analytical Py-GC/MS study J. Anal. Appl. Pyrolysis 2011, 92, 430-438 10.1016/j.jaap.2011.08.006
32. Yang, L. R.; Tsai, D. S.; Chao, Y. S.; Chung, W. H.; Wilkinson, D. P. Enhance the oxygen reduction activity of ruthenium selenide pyrite catalyst with nitrogen-doped carbon Int. J. Hydrogen Energy 2011, 36, 7381-7390 10.1016/j.ijhydene.2011.03.113
33. Kim, W.; Joo, J. B.; Kim, N.; Oh, S.; Kim, P.; Yi, J. Preparation of nitrogen-doped mesoporous carbon nanopipes for the electrochemical double layer capacitor Carbon 2009, 47, 1407-1411 10.1016/j.carbon.2009.01.043
34. Luo, W.; Wang, B.; Heron, C. G.; Allen, M. J.; Morre, J.; Maier, C. S.; Stickle, W. F.; Ji, X. Pyrolysis of cellulose under ammonia leads to nitrogen-doped nanoporous carbon generated through methane formation Nano Lett. 2014, 14, 2225-2229 10.1021/nl500859p
35. Li, Y.; Zhu, S. M.; Liu, Q. L.; Chen, Z. X.; Gu, J. J.; Zhu, C. L.; Lu, T.; Zhang, D.; Ma, J. N-doped porous carbon with magnetic particles formed in situ for enhanced Cr (VI) removal Water Res. 2013, 47, 4188-4197 10.1016/j.watres.2012.10.056
36. Wang, X.; Li, X.; Zhang, L.; Yoon, Y.; Weber, P. K.; Wang, H.; Guo, J.; Dai, H. N-doping of graphene through electrothermal reactions with ammonia Science 2009, 324, 768-771 10.1126/science.1170335
37. Gong, K.; Du, F.; Xia, Z.; Durstock, M.; Dai, L. Nitrogen-doped carbon nanotube arrays with high electrocatalytic activity for oxygen reduction Science 2009, 323, 760-764 10.1126/science.1168049
38. Maldonado, S.; Stevenson, K. J. Influence of nitrogen doping on oxygen reduction electrocatalysis at carbon nanofiber electrodes J. Phys. Chem. B 2005, 109, 4707-4716 10.1021/jp044442z
39. 2 uptake over highly porous N-doped activated carbon monoliths prepared by physical activation Chem. Commun. 2012, 48, 10283-10285 10.1039/c2cc35334b
40. Shao, Y.; Wang, X.; Engelhard, M.; Wang, C.; Dai, S.; Liu, J.; Yang, Z.; Lin, Y. Nitrogen-doped mesoporous carbon for energy storage in vanadium redox flow batteries J. Power Sources 2010, 195, 4375-4379 10.1016/j.jpowsour.2010.01.015
41. Li, Y.; Wang, J.; Li, X.; Liu, J.; Geng, D.; Yang, J.; Li, R.; Sun, X. Nitrogen-doped carbon nanotubes as cathode for lithium-air batteries Electrochem. Commun. 2011, 13, 668-672 10.1016/j.elecom.2011.04.004
42. Zhang, L. L.; Zhao, X.; Ji, H.; Stoller, M. D.; Lai, L.; Murali, S.; McDonnell, S.; Cleveger, B.; Wallace, R. M.; Ruoff, R. S. Nitrogen doping of graphene and its effect on quantum capacitance, and a new insight on the enhanced capacitance of N-doped carbon Energy Environ. Sci. 2012, 5, 9618-9625 10.1039/c2ee23442d
43. Chen, P.; Xiao, T. Y.; Qian, Y. H.; Li, S. S.; Yu, S. H. A Nitrogen-Doped Graphene/Carbon Nanotube Nanocomposite with Synergistically Enhanced Electrochemical Activity Adv. Mater. 2013, 25, 3192-3196 10.1002/adma.201300515
44. Cernansky, R. State of the art soil Nature 2015, 517, 258-260 10.1038/517258a
45. Zhao, L.; Baccile, N.; Gross, S.; Wei, W.; Sun, Y.; Antonietti, M. Sustainable nitrogen-doped carbonaceous materials from biomass derivatives Carbon 2010, 48, 3778-3787 10.1016/j.carbon.2010.06.040
46. Sohi, S. P. Carbon storage with benefits Science 2012, 338, 1034-1035 10.1126/science.1225987
47. Al-Wabel, M. I.; Al-Omran, A.; El-Naggar, A. H.; Nadeem, M.; Usman, A. R.Pyrolysis temperature induced changes in characteristics and chemical composition of biochar produced from conocarpus wastes Bioresour. Technol. 2013, 131, 374-379 10.1016/j.biortech.2012.12.165
48. Vispute, T. P.; Zhang, H.; Sanna, A.; Xiao, R.; Huber, G. W. Renewable chemical commodity feedstocks from integrated catalytic processing of pyrolysis oils Science 2010, 330, 1222-1227 10.1126/science.1194218
49. Carlson, T. R.; Cheng, Y. T.; Jae, J.; Huber, G. W. Production of green aromatics and olefins by catalytic fast pyrolysis of wood sawdust Energy Environ. Sci. 2011, 4, 145-161 10.1039/C0EE00341G
50. Cheng, Y. T.; Huber, G. W. Chemistry of furan conversion into aromatics and olefins over HZSM-5: a model biomass conversion reaction ACS Catal. 2011, 1, 611-628 10.1021/cs200103j
51. Vaitheeswaran, S.; Green, S. K.; Dauenhauer, P.; Auerbach, S. M. On the Way to Biofuels from Furan: Discriminating Diels-Alder and Ring-Opening Mechanisms ACS Catal. 2013, 3, 2012-2019 10.1021/cs4003904
52. Lifshitz, A.; Bidani, M.; Bidani, S. Thermal reactions of cyclic ethers at high temperatures. III. Pyrolysis of furan behind reflected shocks J. Phys. Chem. 1986, 90, 5373-5377 10.1021/j100412a096
53. Bacskay, G. B.; Martoprawiro, M.; Mackie, J. C. The thermal decomposition of pyrrole: an ab initio quantum chemical study of the potential energy surface associated with the hydrogen cyanide plus propyne channel Chem. Phys. Lett. 1999, 300, 321-330 10.1016/S0009-2614(98)01388-8
54. Marris, E. Putting the carbon back: Black is the new green Nature 2006, 442, 624-626 10.1038/442624a
55. Cheng, Y. T.; Wang, Z.; Gilbert, C. J.; Fan, W.; Huber, G. W. Production of p-Xylene from Biomass by Catalytic Fast Pyrolysis Using ZSM-5 Catalysts with Reduced Pore Openings Angew. Chem., Int. Ed. 2012, 51, 11097-11100 10.1002/anie.201205230
56. Liu, C.; Wang, H.; Karim, A. M.; Sun, J.; Wang, Y. Catalytic fast pyrolysis of lignocellulosic biomass Chem. Soc. Rev. 2014, 43, 7594-7623 10.1039/C3CS60414D
57. Henry, G. D. De novo synthesis of substituted pyridines Tetrahedron 2004, 60, 6043-6061 10.1016/j.tet.2004.04.043