Citation: LIU Min, WANG Yong-gang, ZHAO Peng, QU Si-jian, CHEN Gui-feng. Molecular characterization of sulfur and nitrogen compounds in THF extract of Baishihu lignite[J]. Journal of Fuel Chemistry and Technology, ;2019, 47(3): 257-262. shu

Molecular characterization of sulfur and nitrogen compounds in THF extract of Baishihu lignite

LIU Min ^1,2,3,, ,
WANG Yong-gang ¹ ,
ZHAO Peng ^2,3 ,
QU Si-jian ^2,3 ,
CHEN Gui-feng ^2,3

1.
China University of Mining and Technology(Beijing), Beijing 100083, China
2.
China Coal Research Institute, Beijing 100013, China
3.
State Key Laboratory of Coal Mining and Clean Utilization, Beijing 100013, China

Corresponding author: LIU Min, 78562115@qq.com
Received Date: 19 October 2018
Revised Date: 2 December 2018

Fund Project: This project was supported by the Beijing Natural Science Foundation (BJNSF2182090) and Science and Technology Innovation Fund of China Coal Research Institute(2017JC01)the Beijing Natural Science Foundation BJNSF2182090Science and Technology Innovation Fund of China Coal Research Institute 2017JC01

Figures(6)

Baishihu lignite was subjected to Soxhlet extraction by tetrahydrofuran (THF). The extract was reacted with iodomethane in the presence of silver tetrafluoroborate and converted to methylsulfonium salts. The methylsulfonium salts and nitrogen compounds were characterized by electrospray ionization (ESI) and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). Combined with sulfur and nitrogen chemiluminescence detectors (GC-SCD and GC-NCD), the forms of sulfur and nitrogen compounds in THF extracts were studied. The results showed that S₁, S₂, N₁ and N₁O₁ class species were identified in THF extract. The sulfur and nitrogen compounds were mostly dibenzothiophene and carbazole compounds.
- low rank coal,
- extraction,
- sulfide,
- nitride,
- methyl derivatization,
- ion cyclotron resonance mass spectrometry
1. [1]
  SHU Ge-ping, SHI Shi-dong, LI Ke-jian. Direct Coal Liquefaction[M]. Beijing:Coal Industry Press, 2003.
2. [2]
  SHI Shi-dong. Engineering Basis of Coal Hydro-Liquefaction[M]. Beijing:Chemical Industry Press, 2003.
3. [3]
  HAENEL M W. Recent progress in coal structure research[J]. Fuel, 1992,71(11):1211-1223. doi: 10.1016/0016-2361(92)90046-Q
4. [4]
  LIU Min, SHI Shi-dong, QU Si-Jian, LIU Li-lin, SHENG Ming, MAO Xue-feng. Progress in theoretical research on reaction mechanism of coal direct liquefaction[J]. Clean Coal Technol, 2015,21(4):49-54.
5. [5]
  NEAVEL R. Liquefaction of coal in hydrogen-donor and non-donor vehicles[J]. Fuel, 1976,55(3):237-242.
6. [6]
  JIA Wei. Effect of small molecular compounds in coal on rapid liquefaction of coal at high temperature[D]. Shanxi: Taiyuan University of Technology, 2010.
7. [7]
  NI H X, YAN L L, MA C, SHI Q. Molecular composition of soxhlet n-methyl-2-pyrrolidinone extracts from a lignite[J]. Energy Fuels, 2016,30(11):9285-9292. doi: 10.1021/acs.energyfuels.6b01990
8. [8]
  ⅡON M, TAKANOHASHI T, OHSUGA H. Extraction of coals with CS₂-N-methyl-2-pyrrolidinone mixed solvent at room temperature[J]. Fuel, 1988,67(12):1639-1647. doi: 10.1016/0016-2361(88)90208-6
9. [9]
  MATHEWS J P, BURGESS C, PAINTER P. Interactions of illinois No.6 bituminous coal with solvents:A review of solvent swelling and extraction literature[J]. Energy Fuels, 2015,29(3):1279-1294. doi: 10.1021/ef502548x
10. [10]
  FACRIS L, FLORES J. Sorption of heavy metals on a coal beneficiation tailing material:Ⅱ.Adsorptive particulate flotation[J]. Coal Prep, 2002,22(5):234-248.
11. [11]
  TAKANOHASHI T, OHKAW T, YANAGIDA T. Effect of maceral composition on the extraction of bituminous coals with carbon disulphide-n-methyl-2-pyrridinone mixed solvent at room temperature[J]. Fuel, 1993,72(1):51-55.
12. [12]
  CAI M, SMART R. Quantitative analysis of N-methyl-2-pyroolidinone in coal extracts by TGA-FTIR[J]. Energy Fuels, 1993,7(1):52-56. doi: 10.1021/ef00037a010
13. [13]
  GAO H, NOMURA M, SATORU M A. Statistical distribution characteristics of pyridine transport in coal particles and a series of new phenomenological models for overshoot and nonovershoot solvent swelling of coal particles[J]. Energy Fuel, 1999,13(2):518-528. doi: 10.1021/ef980210l
14. [14]
  CHEN Chong, GAO Jin-sheng, YAN Jie. Study on Extraction of coal with cyclohexanone[J]. J Fuel Chem Technol, 1997,25(1):60-64.
15. [15]
  LIY F, WEI X Y, GUI J, WANG Y G, LI P, ZONG Z M. Characterization of biomarkers and structural features of condensed aromatics in xianfeng lignite[J]. Energy Fuels, 2013,27(12):7369-7378. doi: 10.1021/ef402027g
16. [16]
  RANMAN M, SAMANTA A, GUPTA R. Production and characterization of ash-free coal from low-Rank canadian coal by solvent extraction[J]. Fuel Process Technol, 2013,115(11):88-98.
17. [17]
  STOCK L M, OBENG M. Oxidation and carboxylation:a reaction sequence for the study of aromatic structural elements in pocahontas no.3 coal[J]. Energy Fuels, 1997,11(5):987-997. doi: 10.1021/ef960229t
18. [18]
  SHI Quan, ZHAO Suo-qi, XU Chun-ming, Hou Du-jie. Application of fourier transform ion cyclotron resonance mass spectrometer in petroleum composition analysis[J]. J Mass Spectr, 2008,29(6):367-378.
19. [19]
  WU Z, RODEGERS R P, MARSHALL A G. Compositional determination of acidic species in illinois no. 6 coal extracts by electrospray ionization fourier transform ion cyclotron resonance mass spectrometry[J]. Energy Fuels, 2004,18(5):1424-1428. doi: 10.1021/ef049933x
20. [20]
  WU Z, RODGERS R P, MARSHALL A G. Two-and three-dimensional van krevelen diagrams:A graphical analysis complementary to the kendrick mass plot for sorting elemental compositions of complex organic mixtures based on ultrahigh-resolution broadband fourier transform ion cyclotron resonance mass measurements[J]. Anal Chem, 2004,76(9):2511-2516. doi: 10.1021/ac0355449
21. [21]
  SHI Q, PAN N, LONG H, CUI D, GUO X, LONG Y, CHUNG K H, ZHAO S, XU C, HSU C S. Characterization of middle-temperature gasification coal tar. part 3:Molecular composition of acidic compounds[J]. Energy Fuels, 2013,27(1):108-117. doi: 10.1021/ef301431y
22. [22]
  KONG J, WEI X Y, YA H L, LI Z K, ZHAO M X, LI Y, ZONG Z M. Analysis of extractable basic nitrogen compounds in buliangou subbituminous coal by positive-ion ESI FT-ICR MS[J]. Fuel, 2015,159:385-391. doi: 10.1016/j.fuel.2015.06.091
23. [23]
  SHI Q, HOU D, CHUNG K H, XU C, ZHAO S, ZHANG Y. Characterization of heteroatom compounds in a crude oil and its saturates, aromatics, resins and asphaltenes (sara) and non-basic nitrogen fractions analyzed by negative-ion electrospray ionization fourier transform ion cyclotron resonance mass spectrometry[J]. Energy Fuels, 2010,24(4):2545-2553. doi: 10.1021/ef901564e
24. [24]
  BRADLEY C, SCHILLER D J. Determination of sulfur compound distribution in petroleum by gas chromatography with a flame photometric detector[J]. Anal Chem, 1986,58(14):3017-3021. doi: 10.1021/ac00127a026
25. [25]
  GARCIA C L, BECCHI M, GRENIER M F, PAISSE O, SZYMANSKIT R. Analysis of aromatic sulfur compounds in gas oils using gc with sulfur chemiluminescence detection and high-resolution ms[J]. Anal Chem, 2002,74(15):3849-3857. doi: 10.1021/ac011190e
26. [26]
  CHAWLA B, SANZO F D. Determination of sulfur components in light petroleum streams by high-resolution gas chromatography with chemiluminescence detection[J]. J Chromatography, 1992,589(1/2):271-279.
27. [27]
  SHI Q, XU C, ZHAO S, CHUNG K H, ZHANG Y. Characterization of basic nitrogen species in coker gas oils by positive-ion electrospray ionization fourier transform ion cyclotron resonance mass spectrom[J]. Energy Fuels, 2009,24(1):563-569.
28. [28]
  LIU P, SHI Q, CHUNG K H, ZHANG Y, PAN N. Molecular characterization of sulfur compounds in venezuela crude oil and its sara fractions by electrospray ionization fourier transform ion cyclotron resonance mass spectrom[J]. Energy Fuels, 2010,24(9):5089-5096. doi: 10.1021/ef100904k
29. [29]
  WU Mei, SHI Jun-ge, TIAN Song-bai. Analysis of elemental sulfur in gasoline by GC-SCD[J]. Acta Pet Sin(Pet Process Sect), 2008,33(2):320-325.
30. [30]
  HUANG Peng, ZHANG Xiao-jing, MAO Xue-feng, LI Wei-ling. Distribution of sulfur and nitrogen compounds in shenfu coal liquefied oil hydrorefining process[J]. J Fuel Chem Technol, 2015,43(12):37-43.
31. [31]
  LI Yan-hong. Study on the existence and distribution of nitrogen-containing compounds in coal liquefied oil[D]. Shanghai: East China University of Science and Technology, 2014.
1. [1]
  Zhanxiang Liu , Chengshan Yuan , Jie Han , Shuanglian Cai , Qihan Zhang , Lin Wu , Yuan Zheng , Xingwen Sun , Qingwen Liu , Ying Xiong , Guangao Yu , Xin Du , Houjin Li , Jianrong Zhang , Shuyong Zhang . Recommendations for Basic Operations and Standards for Organic Chemical Extraction and Washing Experiments. University Chemistry, 2025, 40(5): 55-65. doi: 10.12461/PKU.DXHX202410039
2. [2]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
3. [3]
  Jiahong ZHENG , Jiajun SHEN , Xin BAI . Preparation and electrochemical properties of nickel foam loaded NiMoO₄/NiMoS₄ composites. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 581-590. doi: 10.11862/CJIC.20230253
4. [4]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
5. [5]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
6. [6]
  Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
7. [7]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
8. [8]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
9. [9]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
10. [10]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
11. [11]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
12. [12]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
13. [13]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
14. [14]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
15. [15]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . 卤化物钙钛矿的单双向离子迁移. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-. doi: 10.3866/PKU.WHXB202311011
16. [16]
  Xiaotian ZHU , Fangding HUANG , Wenchang ZHU , Jianqing ZHAO . Layered oxide cathode for sodium-ion batteries: Surface and interface modification and suppressed gas generation effect. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 254-266. doi: 10.11862/CJIC.20240260
17. [17]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
18. [18]
  Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
19. [19]
  Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
20. [20]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1123)
HTML views(209)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142