Citation: LIU Zhen-zhen, LUO Zhong-yang, MA Shuai, FANG Meng-xiang. Influence of phenolics on hydrodenitrogenation, hydrodesulfurization and hyrodearomatization of coal tar components[J]. Journal of Fuel Chemistry and Technology, ;2015, 43(11): 1327-1333. shu

Influence of phenolics on hydrodenitrogenation, hydrodesulfurization and hyrodearomatization of coal tar components

1.
State Key Laboratory of Clean Energy Utilization, Zhejiang University, Hangzhou 310027, China

Corresponding author: LUO Zhong-yang,
Received Date: 27 May 2015
Available Online: 14 August 2015
Fund Project: 国家高技术研究发展计划(863计划,2013AA051203) (863计划,2013AA051203)国际合作项目(2011DFR60190,2010DFA72730) (2011DFR60190,2010DFA72730)

The influence of o-cresol on HDN of quinoline, HDS of DBT and HDA of 1-methylnaphthalene were investigated over a commercial catalyst in a fixed bed micro-reactor. The results suggest that o-cresol could strongly inhibit the HDN reaction of quinoline, HDS of DBT and HDA of 1-methylnaphthalene. The inhibition effect increases with the increasing content of o-cresol, which is resulted from the competitive adsorption between o-cresol and quinoline, DBT, and 1-methylnaphthalene. The presence of o-cresol has little effect on product selectivity. The hydrogenation is favored for aromatic ring without side chain, which is accounted for the steric effect.
- coal tar,
- o-cresol,
- HDN,
- HDS,
- HDA
1. [1]
  [1] 周同娜, 尹海亮, 韩妹娜, 柴永明, 柳云骐, 刘晨光. 不同磷含量对 NiMoP/Al₂O₃ 加氢处理催化剂的影响[J]. 燃料化学学报, 2009, 37(3): 330-334. (ZHOU Tong-na, YIN Hai-liang, HAN Mei-na, CHAI Yong-ming, LIU Yun-qi, LIU Chen-guang. Influences of different phosphorus contents on NiMoP/Al₂O₃ hydrotreating catalysts[J]. J Fuel Chem Technol, 2009, 37(3): 330-334.)
2. [2]
  [2] 宋华, 郭云涛, 李锋, 于洪坤. Ni₂P/TiO₂-Al₂O₃ 催化剂的制备及其加氢脱硫、脱氮性能[J]. 物理化学学报, 2010, 26(9): 2461-2467. (SONG Hua, GUO Yun-tao, LI Feng, YU Hong-kun. Preparation, hydrodesulfurization and hydrodenitrogenation performance of a Ni₂P/TiO₂-Al₂O₃ catalyst[J]. Acta Phys Chim Sin, 2010, 26(9): 2461-2467.)
3. [3]
  [3] 龚树文, 陈皓侃, 李文, 李保庆. 负载 β-Mo₂N_0.78 催化剂上加氢脱硫和加氢脱氮反应行为的研究[J]. 燃料化学学报, 2005, 33(1): 24-27. (GONG Shu-wen, CHEN Hao-kan, LI Wen, LI Bao-qin. Studies on hydrodesulfurization and hydrodenitrogenation with alumina supported β -Mo₂N_0.78 catalyst[J]. J Fuel Chem Technol, 2005, 33(1): 24-27.)
4. [4]
  [4] 张海永, 王永刚, 张培忠, 林雄超, 朱豫飞. NiW/Al₂O₃-Y 催化剂的制备及其对煤焦油加氢处理的研究[J]. 燃料化学学报, 2013, 41(9): 1085-1091. (ZHANG Hai-yong, WANG Yong-gang, ZHANG Pei-zhong, LIN Xiong-chao, ZHU Yu-fei. Preparation of NiW catalysts with alumina and zeolite Y for hydroprocessing of coal tar[J]. J Fuel Chem Technol, 2013, 41(9): 1085-1091.)
5. [5]
  [5] 石振晶, 方梦祥, 唐巍, 王勤辉, 骆仲泱. 多联产煤焦油加氢制取汽柴油试验研究[J]. 煤炭学报, 2014, 39(S1): 219-224. (SHI Zhen-jing, FANG Meng-xiang, TANG Wei, WANG Qin-hui, LUO Zhong-yang. Hydrofining of wide range distillate derived from muti-generation coal tar[J]. J Chin Coal Soc, 2014, 39(S1): 219-224.)
6. [6]
  [7] 石垒, 张增辉, 邱泽刚, 郭芳, 张伟, 赵亮富. P 改性对 Mo-Ni/Al₂O₃煤焦油加氢脱氮性能的影响[J]. 燃料化学学报, 2015, 43(1): 74-80. (SHI Lei, ZHANG Zeng-hui, QIU Ze-gang, GUO Fang, ZHANG Wei, ZHAO Liang-fu. Effect of phosphorus modification on the catalytic properties of Mo-Ni/Al₂O₃ in the hydrodenitrogenation of coal tar[J]. J Fuel Chem Technol, 2015, 43(1): 74-80.)
7. [7]
  [7] 余盼龙. 多联产煤焦油的蒸馏和加氢研究[D]. 杭州: 浙江大学, 2013. (YU Pan-long. Studies for distilling and hydroprocessing on coal tar from polygeneration system[D]. Hangzhou: Zhejiang University, 2013.)
8. [8]
  [8] LU M, WANG A, LI X, DUAN X, TENG Y, WANG Y, SONG C, HU Y. Hydrodenitrogenation of quinoline catalyzed by MCM-41-supported nickel phosphides[J]. Energy Fuels, 2007, 21(2): 554-560.
9. [9]
  [9] SONG T, ZHANG Z, CHEN J, RING Z, YANG H, ZHENG Y. Effect of aromatics on deep hydrodesulfurization of dibenzothiophene and 4, 6-dimethyldibenzothiophene over NiMo/Al₂O₃ catalyst[J]. Energy Fuels, 2006, 20(6): 2344-2349.
10. [10]
  [10] ODEBUNMI E O, OLLIS D F. Catalytic hydrodeoxygenation: II. Interactions between catalytic hydrodeoxygenation of m-cresol and hydrodesulfurization of benzothiophene and dibenzothiophene[J]. J Catal, 1983, 80(1): 65-75.
11. [11]
  [11] ODEBUNMI E O, OLLIS D F. Catalytic hydrodeoxygenation: Ⅲ. Interactions between catalytic hydrodeoxygenation of m-cresol and hydrodenitrogenation of indole[J]. J Catal, 1983, 80(1): 76-89.
12. [12]
  [12] 相春娥, 柴永明, 柳云骐, 刘晨光. NiMoS/γ-Al₂O₃ 上二苯并噻吩加氢脱硫和喹啉加氢脱氮反应的相互影响[J]. 催化学报, 2008, 29(7): 595-601. (XIANG Chun-e, CHAI Yong-ming, LIU Yun-qi, LIU Chen-guang. Mutual influence of hydrodesulfurization of dibenzothiophene and hydrodenitrogenation of quinoline over NiMoS/γ-Al₂O₃ catalyst[J]. Chin J Catal, 2008, 29(7): 595-601.)
13. [13]
  [13] 相春娥, 柴永明, 柳云骐, 刘晨光. 二苯并噻吩和吲哚在 NiMoS/γ-Al₂O₃ 上加氢脱硫和加氢脱氮反应的相互影[J]. 燃料化学学报, 2009, 36(6): 684-690. (XIANG Chun-e, CHAI Yong-ming, LIU Yun-qi, LIU Chen-guang. Mutual influences of hydrodesulfurization of dibenzothiophene and hydrodenitrogenation of indole over NiMoS/γ-Al₂O₃ catalyst[J]. J Fuel Chem Technol, 2009, 36(6): 684-690.)
14. [14]
  [14] DING L, ZHENG Y, ZHANG Z, RING Z, CHEN J. HDS, HDN, HDA, and hydrocracking of model compounds over Mo-Ni catalysts with various acidities[J]. Appl Catal A: Gen, 2007, 319(1): 25-37.
15. [15]
  [15] DUAN X, TENG Y, WANG A, KOGAN V M, LI X, WANG Y. Role of sulfur in hydrotreating catalysis over nickel phosphide[J]. J Catal, 2009, 261(2): 232-240.
16. [16]
  [16] PHILIPPE M, RICHARD F, HUDEBINE D, BRUNET S. Inhibiting effect of oxygenated model compounds on the HDS of dibenzothiophenes over CoMoP/Al₂O₃ catalyst[J]. Appl Catal A: Gen, 2010, 383(1): 14-23.
17. [17]
  [17] 夏良燕.多联产中低温煤焦油加氢工艺及催化剂研究[D]. 杭州: 浙江大学, 2015. (XIA Liang-yan. Studies on hydroprocessing technology and catalysts of low-temperature coal tar from polygeneration[D]. Hangzhou: Zhejiang University, 2015.)
18. [18]
  [18] 唐巍.煤低温热解焦油加氢实验研究及工艺流程模拟[D]. 杭州: 浙江大学, 2014. (TANG Wei. Experimental study on the hydrogenation of low temperature coal tar and system simulation[D]. Hangzhou: Zhejiang University, 2014.)
19. [19]
  [19] 鞠雪艳, 张毓莹, 胡志海, 王丽新, 李大东. NiMo加氢催化剂上1-甲基萘的饱和反应规律[J]. 石油学报, 2012, 28(4): 538-543. (JU Xue-yan, ZHANG Yu-ying, HU Zhi-hai, WANG Li-xin, LI Da-dong. Hydrogenation saturation discipline of 1-methyl naphthalene over Ni-Mo catalyst[J]. Acta Pet Sin, 2012, 28(4): 538-543.)
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