Citation: DENG Tian-yin, GAO Li-juan, MA Lin-ge, CHEN Jing-yun, LI Jing, GUO Xiao-fen. Phenol etherification with methanol to anisole over supported Cs catalysts[J]. Journal of Fuel Chemistry and Technology, ;2016, 44(9): 1138-1144. shu

Phenol etherification with methanol to anisole over supported Cs catalysts

National Institute of Clean-and-Low-Carbon Energy, Shenhua Group, Beijing 102209, China

Corresponding author: GUO Xiao-fen, guoxiaofen@nicenergy.com
Received Date: 26 February 2016
Revised Date: 12 June 2016

Fund Project: National High Technology Research and Development Program of China 2011AA05A202National High Technology Research and Development Program of China 863 programShenhua Group Foundation CF9300140004

Figures(8)

The effect of acid and basic sites, support, cesium precursor and cesium loading on the performance of supported Cs catalysts in the etherification of phenol with methanol to anisole was investigated. The results illustrate that the cations of basic sites play an important role in the selective conversion of phenol to anisole; the basic sites give higher selectivity to anisole than the acid sites. The catalytic activity in phenol etherification decreases with the increase of the cesium ion binding energy, which is related to the support used. Moreover, the support also has an influence on the amount of strong basic sites, which is related to the selectivity to anisole; high amount of strong basic sites may promote the side reaction and decrease the selectivity to anisole. Cs/SiO₂ catalysts prepared with various precursors are different in the surface Cs/Si atomic ratio, which may also influence the catalytic activity in phenol etherification; if the cesium loading exceeds the monolayer dispersion of cesium on SiO₂, which is nearly 1.0 mmol/g, the average activity of Cs/SiO₂ in phenol etherification decreases greatly.
- supported Cs catalyst,
- activity,
- selectivity,
- phenol,
- anisol,
- etherification
1. [1]
  WANG Ru-cheng, SUN Ming, LIU Qiao-xia, MA Yan-xing, FENG Guang, XU Long, MA Xiao-xun. Extraction and GC/MS analysis of phenolic compounds in low temperature coal tar from Northern Shaanxi[J]. J China Coal Soc, 2011,36(4):664-669.
2. [2]
  MA Bao-qi, REN Pei-jian, YANG Zhan-biao, WANG Shu-kuan. Preparation of Fuel Oil From Coal Tar[M]. Beijing: Chemical Industry Press, 2011.
3. [3]
  HAN Lei, HUANG Chuan-feng, YANG Tian, YANG Yong-jia, LI Wei, WANG Meng-yan, JIAO You-jun, REN Cai-ling, YANG Fan, WANG Yong-juan. A combined device for coal tar processing and coal liquefaction: CN, 201520459906.X[P]. 2015-11-18.
4. [4]
  MORGAN J J, MEIGHAN M H. Extraction of phenols from tar oils by the caustic soda process[J]. Ind Eng Chem, 1925,17:696-700. doi: 10.1021/ie50187a018
5. [5]
  BERGERON P, HINMAN N. Technical and economic analysis of lignin conversion to methyl aryl ethers[J]. Appl Biochem Biotechnol, 1990,24-25(1):15-29. doi: 10.1007/BF02920230
6. [6]
  FARCASIU D, PRINCETON N J. Etherification catalyst: US, 4406821[P]. 1982-08-30.
7. [7]
  DOLHYJ S R, PAPARIZOS C. Motor fuel additives derived from shale oil: US, 4407661[P]. 1983-10-4.
8. [8]
  WANG Ze, DANG Dan, SONG Wen-li, LIN Wei-gang, LI Song-geng. Catalyst and treatment method for upgrading tar by using catalyst: CN, 201310342276.3[P]. 2013-08-07.
9. [9]
  WANG Li-jun, TANG Xiang-hai, ZHU Rui-zhi, PAN Lü-rang. Research on zeolite catalyst for synthesis of methyl phenyl ether with phenol and methanol[J]. Acta Pet Sin (Pet Process Sect), 1998,14:45-49.
10. [10]
  ZHOU Xiu-jing, ZHU Xiao-mei, LI Xue-mei, WANG Zhen-lü, LIU Gang, JIA Ming-jun, ZHANG Wen-xiang. Vapour-phase O-methylation of catechol with methanol on SiO₂-supported ammonium metatungstate catalysts[J]. Chin J Catal, 2008,29(7):671-676.
11. [11]
  SAMOLADA M C, GRIGORIADOU E, KIPARISSIDES Z, VASALOS I A. Selective O-alkylation of phenol with methanol over sulfates supported onγ-Al₂O₃[J]. J Catal, 1995,152(1):52-62. doi: 10.1006/jcat.1995.1059
12. [12]
  VELU S, SWAMY C S. Alkylation of phenol with methanol over magnesium-aluminium calcined hydrotalcites[J]. Appl Catal A: Gen, 1994,119(2):241-252. doi: 10.1016/0926-860X(94)85194-8
13. [13]
  SARALA DEVI G, GIRIDHAR D, REDDY B M. Vapour phase O-alkylation of phenol over alkali promoted rare earth metal phosphates[J]. J Mol Catal A: Chem, 2002,181(1/2):173-8.
14. [14]
  WANG Yan-Li, ZHOU Zhou, WU Shu-jie. Phenol etherification with methanol on SiO₂ supported K catalyst[J]. Petrkchem Technol, 2004,33:170-171.
15. [15]
  BAL R, SIVASANKER S. Vapour phase selective O-alkylation of phenol over alkali loaded silica[J]. Appl Catal A: Gen, 2003,246(2):373-82. doi: 10.1016/S0926-860X(03)00082-6
16. [16]
  AZZOUZ A, NISTOR D, MIRON D, URSU A V, SAJIN T, MONETTE F, NIQUETTE P, HAUSLER R. Assessment of acid-base strength distribution of ion-exchanged montmorillonites through NH₃ and CO₂-TPD measurements[J]. Thermochim Acta, 2006,449(1/2):27-34.
17. [17]
  XIN Qin, LUO Meng-fei. Modern Catalytic Research Methods[M]. Beijing: Science Press, 2009.
18. [18]
  WU Juan-xia, XU Hua, ZHANG Jin. Raman spectroscopy of graphene[J]. Acta Chim Sin, 2014,72:301-318. doi: 10.6023/A13090936
19. [19]
  DAVIS Z D, TATARCHUK B J. Understanding the dispersion of Ag on high surface area TiO₂ supports using XPS intensity ratios[J]. Appl Surf Sci, 2015,353:679-85. doi: 10.1016/j.apsusc.2015.06.086
20. [20]
  LIU Ying-jun, ZHAO Ming, GUO Qin-lin, GUI Lin-lin, XIE You-chang, TANG You-qi. Determination of the maximum monolayer dispersion and dispersed state for WO₃ onγ-Al₂O₃[J]. Acta Chim Sin, 1985,43:728-732.
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