Citation: Jie Li, Lin-Ping Qian, Li-Ya Hu, Bin Yue, He-Yong He. Low-temperature hydrogenation of maleic anhydride to succinic anhydride and γ-butyrolactone over pseudo-boehmite derived alumina supported metal (metal = Cu, Co and Ni) catalysts[J]. Chinese Chemical Letters, ;2016, 27(7): 1004-1008. doi: 10.1016/j.cclet.2016.03.021 shu

Low-temperature hydrogenation of maleic anhydride to succinic anhydride and γ-butyrolactone over pseudo-boehmite derived alumina supported metal (metal = Cu, Co and Ni) catalysts

Department of Chemistry and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, Shanghai 200433, China

Corresponding author: Bin Yue, yuebin@fudan.edu.cn He-Yong He, heyonghe@fudan.edu.cn
Received Date: 15 February 2016
Revised Date: 8 March 2016
Accepted Date: 11 March 2016
Available Online: 19 July 2016

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The pseudo-boehmite derived alumina supported metal (Cu, Co and Ni) catalysts prepared by the impregnation method were investigated in hydrogenation of maleic anhydride (MA) to succinic anhydride (SA) and γ-butyrolactone. The catalysts were characterized by ICP-AES, N₂ adsorption-desorption, XRD, H₂-TPR, CO-TPD, dissociative N₂O adsorption and TEM and the results showed that the alumina possessed mesoporous feature and the metal species were well dispersed on the support. Compared to Cu/Al₂O₃ and Co/Al₂O₃, Ni/Al₂O₃ exhibited higher catalytic activity in the MA hydrogenation with 92% selectivity to SA and nearly 100% conversion of MA at 140 ℃ under 0.5 MPa of H₂ with a weighted hourly space velocity of 2 h^-1 (MA). The stability of Ni/Al₂O₃ catalyst was also investigated.
- Maleic anhydride,
- Hydrogenation,
- Succinic anhydride,
- Nickel
1. [1]
  Q. Wang, H.Y. Cheng, R.X. Liu. Selective hydrogenation of maleic anhydride to γ-butyrolactone in supercritical carbon dioxide[J]. Catal. Commun., 2009,10:592-595. doi: 10.1016/j.catcom.2008.10.042
2. [2]
  Y. Ma, Y.Q. Huang, Y.W. Cheng, L.J. Wang, X. Li. Selective liquid-phase hydrogenation of maleic anhydride to succinic anhydride on biosynthesized Ru-based catalysts[J]. Catal. Commun., 2014,57:40-44. doi: 10.1016/j.catcom.2014.08.001
3. [3]
  S.A. Regenhardt, A.F. Trasarti, C.I. Meyer, T.F. Garetto, A.J. Marchi. Selective gasphase conversion of maleic anhydride to propionic acid on Pt-based catalysts[J]. Catal. Commun., 2013,35:59-63. doi: 10.1016/j.catcom.2013.02.015
4. [4]
  S.M. Jung, E. Godard, S.Y. Jung, K.C. Park, J.U. Choi. Liquid-phase hydrogenation of maleic anhydride over Pd/SiO₂: effect of tin on catalytic activity and deactivation[J]. J. Mol. Catal. A Chem., 2003,198:297-302. doi: 10.1016/S1381-1169(02)00686-6
5. [5]
  H.J. Yuan, C.L. Zhang, W.T. Huo. Selective hydrogenation of maleic anhydride over Pd/Al₂O₃ catalysts prepared via colloid deposition[J]. J. Chem. Sci., 2014,126:141-145. doi: 10.1007/s12039-013-0542-3
6. [6]
  C.I. Meyer, A.J. Marchi, A. Monzon, T.F. Garetto. Deactivation and regeneration of Cu/SiO₂ catalyst in the hydrogenation of maleic anhydride. Kinetic modeling[J]. Appl. Catal. A General, 2009,367:122-129. doi: 10.1016/j.apcata.2009.07.041
7. [7]
  C.I. Meyer, S.A. Regenhardt, A.J. Marchi, T.F. Garetto. Gas phase hydrogenation of maleic anhydride at low pressure over silic α-supported cobalt and nickel catalysts[J]. Appl. Catal. A General, 2012,417-418:59-65. doi: 10.1016/j.apcata.2011.12.026
8. [8]
  J. Li, W.P. Tian, L. Shi. Hydrogenation of maleic anhydride to succinic anhydride over Ni/HY-Al₂O₃[J]. Ind. Eng. Chem. Res., 2010,49:11837-11840. doi: 10.1021/ie101072v
9. [9]
  X. Liao, Y. Zhang, M. Hill. Highly efficient Ni/CeO₂ catalyst for the liquid phase hydrogenation of maleic anhydride[J]. Appl. Catal. A General, 2014,488:256-264. doi: 10.1016/j.apcata.2014.09.042
10. [10]
  K. Keyvanloo, W.C. Hecker, B.F. Woodfield, C.H. Bartholomew. Highly active and stable supported iron Fischer-Tropsch catalysts: effects of support properties and SiO₂ stabilizer on catalyst performance[J]. J. Catal., 2014,319:220-231. doi: 10.1016/j.jcat.2014.08.015
11. [11]
  D.Z. Gao, H.B. Yin, A.L. Wang, L.Q. Shen, S.X. Liu. Gas phase dehydrogenation of ethanol using maleic anhydride as hydrogen acceptor over Cu/hydroxylapatite, Cu/SBA-15, and Cu/MCM-41 catalysts[J]. J. Ind. Eng. Chem., 2015,26:322-332. doi: 10.1016/j.jiec.2014.12.004
12. [12]
  W.T. Huo, C.L. Zhang, H.J. Yuan. Vapor-phase selective hydrogenation of maleic anhydride to succinic anhydride over Ni/TiO₂ catalysts[J]. J. Ind. Eng. Chem., 2014,20:4140-4145. doi: 10.1016/j.jiec.2014.01.012
13. [13]
  U.R. Pillai, E. Sahle-Demessie. Selective hydrogenation of maleic anhydride to gbutyrolactone over Pd/Al₂O₃ catalyst using supercritical CO₂ as solvent[J]. Chem. Commun., 2002,5:422-423.
14. [14]
  U.R. Pillai, E. Sahle-Demessie, D. Young. Maleic anhydride hydrogenation over Pd/Al₂O₃ catalyst under supercritical CO₂ medium[J]. Appl. Catal. B Environ., 2003,43:131-138. doi: 10.1016/S0926-3373(02)00305-3
15. [15]
  D.Z. Gao, Y.H. Feng, H.B. Yin, A.L. Wang, T.S. Jiang. Coupling reaction between ethanol dehydrogenation and maleic anhydride hydrogenation catalyzed by Cu/Al₂O₃, Cu/ZrO₂, and Cu/ZnO catalysts[J]. Chem. Eng. J., 2013,233:349-359. doi: 10.1016/j.cej.2013.08.058
16. [16]
  J. Li, W.P. Tian, X. Wang, L. Shi. Nickel and nickel-platinum as active and selective catalyst for the maleic anhydride hydrogenation to succinic anhydride[J]. Chem. Eng. J., 2011,175:417-422. doi: 10.1016/j.cej.2011.09.023
17. [17]
  P.G. Tang, Y.Y. Chai, J.T. Feng. Highly dispersed Pd catalyst for anthraquinone hydrogenation supported on alumina derived from a pseudoboehmite precursor[J]. Appl. Catal. A General, 2014,469:312-319. doi: 10.1016/j.apcata.2013.10.008
18. [18]
  Z.W. Huang, J. Chen, Y.Q. Jia. Selective hydrogenolysis of xylitol to ethylene glycol and propylene glycol over copper catalysts[J]. Appl. Catal. B Environ., 2014,147:377-386. doi: 10.1016/j.apcatb.2013.09.014
19. [19]
  Y.H. Feng, H.B. Yin, A.L. Wang, T. Xie, T.S. Jiang. Selective hydrogenation of maleic anhydride to succinic anhydride catalyzed by metallic nickel catalysts[J]. Appl. Catal. A General, 2012,425-426:205-212. doi: 10.1016/j.apcata.2012.03.023
20. [20]
  B.C. Lippens, J.H. De Boer. Study of phase transformations during calcination of aluminum hydroxides by selected area electron diffraction[J]. Acta Crystallogr., 1964,17:1312-1322. doi: 10.1107/S0365110X64003267
21. [21]
  H.T. Li, Y.L. Xu, C.G. Gao, Y.X. Zhao. Structural and textural evolution of Ni/γ-Al₂O₃ catalyst under hydrothermal conditions[J]. Catal. Today, 2010,158:475-480. doi: 10.1016/j.cattod.2010.07.015
22. [22]
  G. Paglia, C.E. Buckley, A.L. Rohl. Boehmite derived γ'-alumina system., 1. Structural evolution with temperature, with the identification and structural determination of a new transition phase, γ'-alumina[J]. Chem. Mater., 2004,16:220-236. doi: 10.1021/cm034917j
23. [23]
  T. Pairojpiriyakul, E. Croiset, W. Kiatkittipong. Hydrogen production from catalytic supercritical water reforming of glycerol with cobalt-based catalysts[J]. Int. J. Hydrogen Energy, 2013,38:4368-4379. doi: 10.1016/j.ijhydene.2013.01.169
24. [24]
  B. Jongsomjit, J. Panpranot, J.G. Goodwin Jr.. Co-support compound formation in alumin α-supported cobalt catalysts[J]. J. Catal., 2001,204:98-109. doi: 10.1006/jcat.2001.3387
25. [25]
  P.X. Ling, D. Li, X.Y. Wang. Supported CuO/γ-Al₂O₃ as heterogeneous catalyst for synthesis of diaryl ether under ligand-free conditions[J]. J. Mol. Catal. A Chem., 2012,357:112-116. doi: 10.1016/j.molcata.2012.01.028
26. [26]
  Y.L. Zhang, D.G. Wei, S. Hammache, J.G. Goodwin Jr.. Effect of water vapor on the reduction of Ru-promoted Co/Al₂O₃[J]. J. Catal., 1999,188:281-290. doi: 10.1006/jcat.1999.2666
27. [27]
  B. Jongsomjit, J. Panpranot, J.G. Goodwin Jr.. Effect of zirconi α-modified alumina on the properties of Co/γ-Al₂O₃ catalysts[J]. J. Catal., 2003,215:66-77. doi: 10.1016/S0021-9517(02)00102-1
28. [28]
  L. De Rogatis, T. Montini, A. Cognigni, L. Olivi, P. Fornasiero. Methane partial oxidation on NiCu-based catalysts[J]. Catal. Today, 2009,145:176-185. doi: 10.1016/j.cattod.2008.04.019
29. [29]
  R Molina, G. Poncelet. α-Alumin α-supported nickel catalysts prepared from nickel acetylacetonate: a TPR study, Poncelet,[J]. J. Catal., 1998,173:257-267. doi: 10.1006/jcat.1997.1931
30. [30]
  Z.Y. Hou, O. Yokota, T. Tanaka, T. Yashima. Characterization of C α-promoted Ni/ α-Al₂O₃ catalyst for CH₄ reforming with CO₂[J]. Appl. Catal. A General, 2003,253:381-387. doi: 10.1016/S0926-860X(03)00543-X
31. [31]
  S.F. Guo, L. Shi. Synthesis of succinic anhydride from maleic anhydride on Ni/diatomite catalysts[J]. Catal. Today, 2013,212:137-141. doi: 10.1016/j.cattod.2012.10.004
32. [32]
  M. El Doukkali, A. Iriondo, J.F. Cambra. Deactivation study of the Pt and/or Ni-based γ-Al₂O₃ catalysts used in the aqueous phase reforming of glycerol for H₂ production[J]. Appl. Catal. A General, 2014,472:80-91. doi: 10.1016/j.apcata.2013.12.015
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