Citation: ZHAO Yun-peng, ZHAO Wei, SI Xing-gang, CAO Jin-pei, WEI Xian-yong. Hydrogenation of lignin-derived phenolic compounds over Co@C catalysts[J]. Journal of Fuel Chemistry and Technology, ;2021, 49(1): 55-62. doi: 10.19906/j.cnki.JFCT.2021004 shu

Hydrogenation of lignin-derived phenolic compounds over Co@C catalysts

ZHAO Yun-peng ^1,2,, ,
ZHAO Wei ¹ ,
SI Xing-gang ¹ ,
CAO Jin-pei ^1,, ,
WEI Xian-yong ^1,2

1.
Key Laboratory of Coal Processing and Efficient Utilization, Ministry of Education, China University of Mining & Technology, Xuzhou 221116, China
2.
School of Chemical Engineering and Technology, Xinjiang University, Urumqi 830046, China

Corresponding author: ZHAO Yun-peng, zhaoyp@cumt.edu.cn CAO Jin-pei, caojingpei@cumt.edu.cn
Received Date: 9 September 2020
Revised Date: 10 October 2020

Fund Project: The project was supported by the National Natural Science Foundation of China (21878325), the Fundamental Research Funds for the Central Universities (China University of Mining and Technology, 2019XKQYMS49), and the Priority Academic Program Development of Jiangsu Higher Education Institutions

Figures(10)

Co-MOF was firstly prepared by solvothermal method, and then Co@C catalyst was prepared by one-step pyrolysis method from Co-MOF. The structure of Co@C catalyst was characterized by N₂ physical adsorption-desorption (BET), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Effects of Co-MOF pyrolysis temperature, reaction temperature, initial hydrogen pressure and reaction time on catalytic hydrogenation of guaiacol were investigated. The results show that both Co-MOF and Co@C are dominated by mesoporous. After pyrolysis, lamellar structure of Co-MOF changes into irregular sphericity. As raising pyrolysis temperature, specific surface area of Co@C decreases continuously. Under the conditions of reaction temperature 180 ℃, initial hydrogen pressure 2 MPa and reaction time 2 h, the guaiacol was completely transformed and selectivity of cyclohexanol was 92.8% using Co@C-600 as catalyst. The main reaction pathway of guaiacol hydrogenation catalyzed by Co@C is that guaiacol firstly forms phenol through removal of methoxyl group, and further is hydrogenated to cyclohexanol. In addition, Co@C-600 also has good catalytic activity for other phenolic monomers derived from lignin, such as phenol, p-methoxyphenol and 4-methyl guaiacol.
- lignin,
- guaiacol,
- cyclohexanol,
- hydrodeoxygenation,
- Co@C catalyst
1. [1]
  SHERWOOD J. The significance of biomass in a circular economy[J]. Bioresour Technol,2020,300:122755. doi: 10.1016/j.biortech.2020.122755
2. [2]
  YU Qiang, ZHUANG Xin-shu, YUAN Zhen-hong, QI Wei, WANG Qiong, TAN Xue-song, XU Jin-liang, ZHANG Yu, XU Hui-juan, MA Long-long. Research progress on fuel and chemicals production from lignocellulose biomass[J]. Chem Ind Eng Prog,2012,31(4):784−791.
3. [3]
  ZHU Chen-jie, ZHANG Hui-yan, XIAO Rui, CHEN Yong, LIU Dong, DU Feng-guang, YING Han-jie, OUYANG Ping-kai. Research progress of high value utilization of lignocellulose[J]. Sci Sin Chim,2015,45(5):454−478. doi: 10.1360/N032014-00280
4. [4]
  YUAN Zhen-qiu, LONG Jin-xing, ZHANG Xing-hua, XIA Ying, WANG Tie-jun, MA Long-long. Catalytic conversion of lignocellulose into energy platform chemicals[J]. Prog Chem,2016,28(1):103−110.
5. [5]
  UPTON B M, KASKO A M. Strategies for the conversion of lignin to high-value polymeric materials: review and perspective[J]. Chem Rev,2015,116(4):2275−2306.
6. [6]
  PEREZ J, MUNOZ-DORADO J, DE LA RUBIA T, MARTINEZ J. Biodegradation and biological treatments of cellulose, hemicellulose and lignin: An overview[J]. Int Microbiol,2002,5(2):53−63. doi: 10.1007/s10123-002-0062-3
7. [7]
  YUAN Liang. Application of lignosulfonate in concrete admixture[J]. Spec Steel Techonl,2012,18(2):58−61. doi: 10.3969/j.issn.1674-0971.2012.02.018
8. [8]
  TYMCHYSHYN M, YUAN Z, ZHANG Y, XU C C. Catalytic hydrodeoxygenation of guaiacol for organosolv lignin depolymerization-catalyst screening and experimental validation[J]. Fuel,2019,254:115664. doi: 10.1016/j.fuel.2019.115664
9. [9]
  VERMA S, NADAGOUDA MN, VARMA RS. Visible light-mediated and water-assisted selective hydrodeoxygenation of lignin-derived guaiacol to cyclohexanol[J]. Green Chem,2019,21(6):1253−1257. doi: 10.1039/C8GC03951H
10. [10]
  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]. J Fuel Chem Technol,2013,41(4):443−448. doi: 10.3969/j.issn.0253-2409.2013.04.009
11. [11]
  LUO Z C, ZHENG Z X, WANG Y C, SUN G, JIANG H, ZHAO C. Hydrothermally stable Ru/HZSM-5-catalyzed selective hydrogenolysis of lignin-derived substituted phenols to bio-arenes in water[J]. Green Chem,2016,18(21):5845−5858. doi: 10.1039/C6GC01971D
12. [12]
  WANG X, ZHU S, WANG S, HE Y, LIU Y, WANG J G, FAN W B, LV Y K. Low temperature hydrodeoxygenation of guaiacol into cyclohexane over Ni/SiO₂ catalyst combined with Hβ zeolite[J]. RSC Adv,2019,9(7):3868−3876. doi: 10.1039/C8RA09972C
13. [13]
  WANG X, ZHU S, WANG S, WANG J G, FAN W B, LV Y K. Ni nanoparticles entrapped in nickel phyllosilicate for selective hydrogenation of guaiacol to 2-methoxycyclohexanol[J]. Appl Catal A: Gen,2018,568:231−241. doi: 10.1016/j.apcata.2018.10.009
14. [14]
  LU J Q, LIU X, YU G Q, LV J K, RONG Z M, WANG M, WANG Y. Selective Hydrodeoxygenation of guaiacol to cyclohexanol catalyzed by nanoporous nickel[J]. Catal Lett,2019,150(3):837−848.
15. [15]
  GUO M, PENG J, YANG Q H, LI C. Highly active and selective RuPd bmetallic NPs for the cleavage of the diphenyl ether C–O bond[J]. ACS Catal,2018,8(12):11174−11183. doi: 10.1021/acscatal.8b03253
16. [16]
  HUA M L, SONG J L, XIE C, WU H R, HU Y, HUANG X, HAN B X. Ru/hydroxyapatite as a dual-functional catalyst for efficient transfer hydrogenolytic cleavage of aromatic ether bonds without additional bases[J]. Green Chem,2019,21(18):5073−5079. doi: 10.1039/C9GC02336D
17. [17]
  YAN Long, PANG Huan, HUANG Yao-bing, FU Yao. Supported Pd catalysts for the C-O cleavage of the lignin derived model dimers through intramolecular hydrogenolysis reaction[J]. Acta Chim Sin,2014,72(9):1005−1011. doi: 10.6023/A14050397
18. [18]
  QIU Ze-gang, YIN Chan-juan, LI Zhi-qin, FENG Kuo-yue. Recent advances in hydrodeoxygenation catalysts for phenols[J]. Chem Ind Eng Prog,2019,38(8):3658−3669.
19. [19]
  YUAN S, FENG L, WANG K C, PANG J D, BOSCH M, LOLLAR C, SUN Y J, QIN J S, YANG X Y, ZHANG P, WANG Q, ZOU L F, ZHANG Y M, ZHANG L L, FANG Y, LI J L, ZHOU H C. Stable metal-organic frameworks: design, synthesis, and applications[J]. Adv Mater,2018,30(37):1704303. doi: 10.1002/adma.201704303
20. [20]
  HUANG Gang, CHEN Yu-zhen, JIANG Hai-long. Metal-organic frameworks for catalysis[J]. Acta Chim Sin,2016,74(2):113−129. doi: 10.6023/A15080547
21. [21]
  SHEN K, CHEN X D, CHEN J Y, LI Y W. Development of MOF-derived carbon-based nanomaterials for efficient catalysis[J]. ACS Catal,2016,6(9):5887−5903. doi: 10.1021/acscatal.6b01222
22. [22]
  WANG J, ZHONG Q, XIONG Y H, CHENG D Y, ZENG Y Q, BU Y F. Fabrication of 3D Co-doped Ni-based MOF hierarchical micro-flowers as a high-performance electrode material for supercapacitors[J]. Appl Surf Sci,2019,483:1158−1165. doi: 10.1016/j.apsusc.2019.03.340
23. [23]
  REZAEE S, SHAHROKHIAN S. Facile synthesis of petal-like NiCo/NiO-CoO/nanoporous carbon composite based on mixed-metallic MOFs and their application for electrocatalytic oxidation of methanol[J]. Appl Catal B: Environ,2019,244:802−813. doi: 10.1016/j.apcatb.2018.12.013
24. [24]
  CAI J Y, CHEN Y, SONG H T, HOU L X, LI Z H. MOF derived C/Co@C with a “one-way-valve”-like graphitic carbon layer for selective semi-hydrogenation of aromatic alkynes[J]. Carbon,2020,160:64−70. doi: 10.1016/j.carbon.2020.01.006
25. [25]
  LIU X H, XU L J, XU G Y, JIA W D, MA Y F, ZHANG Y. Selective hydrodeoxygenation of lignin-derived phenols to cyclohexanols or cyclohexanes over magnetic CoNx@NC catalysts under mild conditions[J]. ACS Catal,2016,6(11):7611−7620. doi: 10.1021/acscatal.6b01785
26. [26]
  ZHU J, CHEN F Q, ZHANG Z G, LI M, YANG Q W, YANG Y W, BAO Z B, REN Q L. M-gallate (M = Ni, Co) metal-organic framework-derived Ni/C and bimetallic Ni-Co/C catalysts for lignin conversion into monophenols[J]. ACS Sustainable Chem Eng,2019,7(15).
27. [27]
  DONG L, YIN L L, XIA Q E, LIU X H, GONG X Q, WANG Y Q. Size-dependent catalytic performance of ruthenium nanoparticles in the hydrogenolysis of a β-O-4 lignin model compound[J]. Catal Sci Technol,2018,8(3):735−745. doi: 10.1039/C7CY02014G
28. [28]
  SCHUTYSER W, VAN DEN BOSSCHE G, RAAFFELS A, VAN DEN BOSCH S, KOELEWIJN S F, RENDERS T, SELS B F. Selective conversion of lignin-derivable 4-alkylguaiacols to 4-alkylcyclohexanols over noble and non-noble-metal catalysts[J]. ACS Sustainable Chem Eng,2016,4(10):5336−5346. doi: 10.1021/acssuschemeng.6b01580
29. [29]
  NAKAGAWA Y, ISHIKAWA M, TAMURA M, TOMISHIGE K. Selective production of cyclohexanol and methanol from guaiacol over Ru catalyst combined with MgO[J]. Green Chem,2014,16(4):2197−2203. doi: 10.1039/C3GC42322K
30. [30]
  LONG J X, SHU S Y, WU Q Y, YUAN Z Q, WANG T J, XU Y, ZHANG X H, ZHANG Q, MA L L. Selective cyclohexanol production from the renewable lignin derived phenolic chemicals catalyzed by Ni/MgO[J]. Energy Convers Manage,2015,105:570−577. doi: 10.1016/j.enconman.2015.08.016
31. [31]
  ZHOU M H, WANG Y, WANG Y B, XIAO G M. Catalytic conversion of guaiacol to alcohols for bio-oil upgrading[J]. J Energy Chem,2015,24(4):425−431. doi: 10.1016/j.jechem.2015.06.012
32. [32]
  GUO He-min. The effects of substituent position and type on the chemical properties of aromatic compounds were explained by electron effect[J]. Univ Chem,2008,(5):54−57.
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