Citation: YU Yu-xiao, XU Ying, WANG Tie-jun, MA Long-long, ZHANG Qi, ZHANG Xing-hua, ZHANG Xue. In-situ hydrogenation of lignin depolymerization model compounds to cyclohexanol[J]. Journal of Fuel Chemistry and Technology, ;2013, 41(4): 443-448. shu

In-situ hydrogenation of lignin depolymerization model compounds to cyclohexanol

YU Yu-xiao ^1,2 ,
XU Ying ¹ ,
WANG Tie-jun ^1,, ,
MA Long-long ¹ ,
ZHANG Qi ¹ ,
ZHANG Xing-hua ^1,2 ,
ZHANG Xue ^1,2

1.
1. Key Laboratory of Renewable Energy and Gas Hydrate, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China;

Corresponding author: WANG Tie-jun,
Received Date: 13 November 2012
Available Online: 19 January 2013
Fund Project: 国家自然科学基金(51106108, 51106167) (51106108, 51106167) 国家高技术研究发展计划(863计划, 2012AA051801). (863计划, 2012AA051801)

The integrated process of aqueous phase reforming of methanol for hydrogen and hydrogenation of phenol and guaiacol, two lignin model compounds, was conducted with Raney Ni catalyst in this work. The effects of pressure, temperature, reaction time and mixture ratio of reactants on the performance of in-situ hydrogenation of lignin depolymerization model compounds were investigated. The mechanism was also discussed. Results showed that the guaiacol conversion and cyclohexanol selectivity reached 99.00% and 93.74% with time-on-stream of 7 h, while the phenol conversion and cyclohexanol selectivity were 90.50% and 99.29% with time-on-stream of 12 h under the optimal conditions of 220 ℃, initial pressure of 0 MPa(gauge pressure) and mole ratio of water/methanol/feedstock=20/5/0.8. The in-situ hydrogenation of phenolic compounds was also proved to be superior to the hydrogenation system of phenols with external hydrogen supply. This work provides a new alternative for production of chemicals from the depolymerization products of lignin.
- guaiacol,
- phenol,
- Raney Ni,
- in-situ hydrogenation,
- cyclohexanol
1. [1]
  [1] KLEINERT M, BARTH T. Phenols from lignin[J]. Chem Eng Technol, 2008, 31(5): 736-745.
2. [2]
  [2] 朱清时. 化学的绿色化和绿色植的化学转化[J]. 世界科技研究与发展, 1998, 20(2): 12-17. (ZHU Qing-shi. Greenization of chemistry and chemical transformation of green plants[J]. Research and Development of the World Science and Technology, 1998, 20(2): 12-17.)
3. [3]
  [3] 蒋挺大. 木质素[M]. 2版. 北京: 化学工业出版社, 2008. (JIANG Ting-da. Lignin[M]. Version 2, Beijing: Chemical Industry Press, 2008.)
4. [4]
  [4] ZAKZESKI J, BRUIJNINCXP C A, JONGERIUS A L, WECKHUYSEN B M. The catalytic valorization of lignin for the production of renewable chemicals[J]. Chem Rev, 2010, 110(6): 3552-3599.
5. [5]
  [5] SAISU M, SATO T, WATANABE M, ADSCHIRI T, ARAI K. Conversion of lignin with supercritical water-phenol mixtures[J]. Energy Fuels, 2003, 17(4): 922-928.
6. [6]
  [6] SHABTAI J S, ZMIERCZAK W W, CHORNET E. Process for conversion of lignin to reformulated hydrocarbon gasoline: US, 5959167A. 1999-09-28.
7. [7]
  [7] BUI V N, LAURENTI D, AFANASIEV P, GEANTET C. Hydrodeoxygenation of guaiacol with CoMo catalysts. Part I: Promoting effect of cobalt on HDO selectivity and activity[J]. Appl Catal B, 2011, 101(3): 239-245.
8. [8]
  [8] YAN N, ZHAO C, DYSON P J, WANG C, LIU L, KOU Y. Selective degradation of wood lignin over noble-metal catalysts in a two-step process[J]. ChemSusChem, 2008, 1(7): 626-629.
9. [9]
  [9] CHO R L, JI S Y, YOUNG W S, JAE W C, JEONG M H, DONG J S, YOUNG K P. Catalytic roles of metals and supports on hydrodeoxygenation of lignin monomer guaiacol[J]. Catal Commun, 2012, 17: 54-58.
10. [10]
  [10] 王威燕, 张小哲, 杨运泉, 杨彦松, 彭会左, 罗和安. La-Ni-Mo-B非晶态催化剂的制备及其苯酚加氢脱氧催化性能[J]. 物理化学学报, 2012, 28(5): 1243-1251. (WANG Wei-yan, ZHANG Xiao-zhe, YANG Yun-quan, YANG Yan-song, PENG Hui-zuo,LUO He-An. Preparation of La-Ni-Mo-B amorphous catalyst and its catalytic properties for hydrodeoxygenation of phenol[J]. Acta Physico-Chimica sinica, 2012, 28(5): 1243-1251.)
11. [11]
  [11] 李小年, 项益智. 一类新的液相催化氢化反应体系[J]. 中国科学B辑: 化学, 2007, 37(2): 136-142. (LI Xiao-nian, XIANG Yi-zhi. A new liquid phase catalytic hydrogenation reaction system[J].Science China Chemistry, 2007, 37(2): 136-142.)
12. [12]
  [12] 曹晓霞, 项益智, 卢春山, 马磊, 张群峰, 李小年. 甲醇水相重整制氢原位还原糠醛制备糠醇[J]. 稀有金属材料与工程, 2010, 39(S2): 516-520. (CAO Xiao-xia, XIANG Yi-zhi, LU Chun-shan, MA Lei, ZHANG Qun-feng, LI Xiao-nian. In-situ reduction of furfural to furfuryl alcohol with hydrogen derived from aqueous-phase reforming of methanol[J]. Rare Metal Materials and Engineering, 2010, 39(S2): 516-520)
13. [13]
  [13] XIANG Y Z, KONG L N, LU C S, MA L, LI X N. Lanthanum-promoted Pd／Al₂O₃ catalysts for liquid phase in situ hydrogenation of phenol to cyclohexanone[J]. Reac Kinet, Mech and Catal, 2010, 100(1): 227-235.
14. [14]
  [14] HUBER G W, SHABAKER J W, DUMESIC J A. Raney Ni-Sn catalyst for H₂ production from biomass-derived hydrocarbons[J]. Science, 2003, 300: 2074-2077.
15. [15]
  [15] DAVDA R R, SHABAKER J W, HUBER G W, CORTRIGHT R D, DUMESIC J A. A review of catalytic issues and process conditions for renewable hydrogen and alkanes by aqueous-phase reforming of oxygenated hydrocarbons over supported metal catalysts[J]. Appl Catal B, 2005(56): 171-186.
16. [16]
  [16] 白赢, 卢春山, 马磊, 陈萍, 郑遗凡, 李小年. Ce和Mg改性的γ-Al₂O₃负载Pt催化剂催化乙二醇水相重整制氢[J]. 催化学报, 2006, 27(3): 275-280. (BAI Ying, LU Chun-shan, MA Lei, CHEN Ping, ZHENG Yi-fan, LI Xiao-nian. Hydrogen Production by Aqueous-Phase Reforming of Ethylene Glycol over Pt Catalysts Supported on γ-A1₂O₃ Modified with Ce and Mg[J]. Chinese Journal of Catalysis, 2006, 27(3): 275-280.)
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