Citation: HUANG Peng, ZHANG Xiao-jing, MAO Xue-feng, LI Wei-lin. Change of sulfur and nitrogen compounds in the direct liquefaction oil from Shenfu coal upon the hydrofining process[J]. Journal of Fuel Chemistry and Technology, ;2016, 44(1): 37-43. shu

Change of sulfur and nitrogen compounds in the direct liquefaction oil from Shenfu coal upon the hydrofining process

HUANG Peng ^1,2,*,, ,
ZHANG Xiao-jing ^1,2 ,
MAO Xue-feng ^1,2 ,
LI Wei-lin ^1,2

1.
Beijing Coal Chemistry Research Institute, China Coal Research Institute, Beijing 100013, China
2.
State Key Laboratory of Coal Mining and Clean Utilization, Beijing 100013, China

Corresponding author: HUANG Peng, squallok@qq.com
Received Date: 28 July 2015
Revised Date: 8 September 2015

Fund Project: the National Key Technology R & D Program 2012BAA04B04the International S & T Cooperation Program of China 2013DFA61660The project was supported by the National Science Foundation of China U1261117

Figures(10)

The direct liquefaction oil from Shenfu coal and the refined oil through hydrofining were cut into different fractions by true boiling point distillation and the sulfur and nitrogen compounds in each fraction were analyzed by GC-PFPD and GC-NCD; the change in the sulfur and nitrogen compounds in the direct liquefaction oil upon the hydrofining process was then investigated. The results illustrated that the sulfur content in the direct liquefaction oil takes a 'U' type distribution with the distillation range from low to high boiling point, whereas the content of nitrogen is far higher than that of sulfur, which increases with the rising of the fraction boiling point. After hydrofining, the sulfur and nitrogen contents are removed by 97% and 98.9%, respectively. Bicyclic and tricyclic compounds such as benzothiophene and dibenzothiophene account for 93.25% of the sulfur compounds in the coal liquefaction oil; after the hydrofining, low boiling point sulfur compounds such as mercaptan, sulfoether and thiophene almost disappear, with benzothiophene and dibenzothiophene as the main sulfur compounds that are difficult to remove. In the coal liquefaction oil, five-membered heterocycle neutral compounds account for 54.96% nitrogen and the portion of basic nitrogen compounds, including mainly anilines with a relatively small amount of quinolones, is 23.22%. After hydrofining, fatty amines are removed completely and the residual nitrogen in the refined oil exists mainly as the basic nitrogen compounds such as quinolones and anilines.
- direct coal liquefaction oil,
- sulfur compounds,
- nitrogen compounds,
- narrow fractions,
- hydrofining
1. [1]
  ZHU Ji-sheng, NORCIO L P, KUGLER E L, DADYBURJOR D B, YANG Jian-li, LIU Zhen-yu, ZHONG Bing. Characterization of hexane soluble oils from liquefaction of two bituminous coals[J]. J Fuel Chem Technol, 2001,29(3):214-218.
2. [2]
  WANG Yong-gang, WANG Cai-hong, YANG Zheng-wei, DONG Min. Characterization of direct liquefied oils from three typical chinese coals[J]. J China Univ Min Technol, 2009,38(1):96-100.
3. [3]
  HUANG P, ZHANG X J, MAO X F. Research on the production of aromatic hydrocarbon via hydroreforming a light fraction in direct coal liquefaction oil[J]. Energy Fuels, 2015,29(1):86-90. doi: 10.1021/ef502146a
4. [4]
  OMAIS B, COURTIADE M, CHARON N, ROULLET C, PONTHUS J, THIÉBAUT D. Using gas chromatography to characterize a direct coal liquefaction naphtha[J]. J Chromatogr A, 2012,1226(4):61-70.
5. [5]
  WANG Yong-gang, ZHOU Jian-ming, WANG Cai-hong, YANG Zheng-wei. Direct liquefaction oil products distribution of Xianfeng and Shenhua coals[J]. J China Coal Soc, 2006,31(1):81-84.
6. [6]
  YIN Chang-long, XIA Dao-hong. Distribution of sulfur compounds in the full-range fcc and rfcc gasoline[J]. J Fuel Chem Technol, 2001,29(3):256-258.
7. [7]
  LING Feng-xiang, YAO Yin-tang, MA Bo, WANG Shao-jun. Study of sulfur compounds in diesel oil by GC-atomic emission detection[J]. J Fuel Chem Technol, 2002,30(6):535-539.
8. [8]
  WANG Shao-jun, LING Feng-xiang, WANG An-jie. Testing sample choice for non-hydrodesulfurization of diesels[J]. J Fuel Chem Technol, 2005,33(2):171-174.
9. [9]
  SHAN Hong-hong, LI Chun-yi. Distribution of sulfur in FCC gasoline and desulfurization with catalytic cracking[J]. J China Univ Pet (Nat Sci), 2001,25(6):78-80.
10. [10]
  ZHANG Yue-qin. Characterizations of nitrogen compounds in coker gas oil and straight run diesel oil[J]. Petrol Process Petrochem, 2013,44(1):41-45.
11. [11]
  ZHANG Yue-qin. Characterization of nitrogen compounds in fcc diesel fraction[J]. Petrol Process Petrochem, 2013,44(1):87-91.
12. [12]
  MURTI S D S, SAKANISHI K, OKUMA O, KORAI Y, MOCHIDA I. Detailed characterization of heteroatom-containing molecules in light distillates derived from Tanito Harum coal and its hydrotreated oil[J]. Fuel, 2002,81(17):2241-2248. doi: 10.1016/S0016-2361(02)00159-X
13. [13]
  MURTI S D S, CHOI K H, SAKANISHI K, OKUMA O, KORAI Y, MOCHIDA I. Analysis and removal of heteroatom containing species in coal liquid distillate over NiMo catalysts[J]. Fuel, 2005,84(2):135-142.
14. [14]
  GU X, MAO X F, ZHAO Y, LI W B, ZHANG X J. Study on the basic nitrogen compounds from coal-derived oil[J]. J Coal Sci Eng (China), 2013,19(1):83-89. doi: 10.1007/s12404-013-0114-7
15. [15]
  GU Xiao-hui, HUANG Peng, LI Wen-bo, AI Jun. Study on the nitrogen compounds in liquefaction oil[J]. Clean Coal Technol, 2011,17(4):38-40.
16. [16]
  KIM K H. Performance characterization of the GC/PFPD for H₂S, CH₃SH, DMS, and DMDS in air[J]. Atmos Environ, 2005,39(12):2235-2242. doi: 10.1016/j.atmosenv.2004.12.039
17. [17]
  OA M A, FLORESB M, PARRAA S, QUIROZA W, MAXWELLC P, MESTERC Z. Chemometric optimization of an extraction procedure using tartaric acid for butyltin compounds from sediment samples by GC-PFPD[J]. J Chil Chem Soc, 2015,60:2803-2806. doi: 10.4067/S0717-97072015000100006
18. [18]
  WANG F C, ROBBINS WK, GREANEY MA. Speciation of nitrogen-containing compounds in diesel fuel by comprehensive two-dimensional gas chromatography[J]. J Sep Sci, 2004,27(5/6):468-472.
19. [19]
  XIANG Zhang-min, SHANG Sheng-hua, CAI Kai, GENG Zhao-liang, CHEN Xing-jiang. Determination and decline study of matrine residue in tobacco by gas chromatography-nitrogen chemiluminessence detector[J]. Chin J Pestic Sci, 2012,14(2):198-202.
20. [20]
  YAN Jia-bao, ZOU Xiong, XIA Ming-gui. Removing basic nitrogen compounds from fcc lco[J]. Petrol Process Petrochem, 2005,36(3):25-28.
21. [21]
  LI Li-quan. Process calculation and technical analysis of hydro cracking unit[M]. Beijing: China Petrochemical Press, 2009.
22. [22]
  BEJ S K, MAITY S K, TURAGA U T. Search for an efficient 4, 6-DMDBT hydrodesulfurization catalyst: A review of recent studies[J]. Energy Fuels, 2004,18(5):1227-1237. doi: 10.1021/ef030179+
23. [23]
  GARCÍA-MARTÍNEZ J C, CASTILLO-ARAIZA C O, HEREDIA J A D L R, TREJO E, MONTESINOS A. Kinetics of HDS and of the inhibitory effect of quinoline on HDS of 4, 6-DMDBT over a Ni-Mo-P/Al₂O₃ catalyst: Part Ⅰ[J]. Chem Eng J, 2012,210(6):53-62.
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