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

LIU Min; WANG Yong-gang; ZHAO Peng; QU Si-jian; CHEN Gui-feng

Volume 47 Issue 3

Mar. 2019

Turn off MathJax

Article Contents

Article Navigation > Journal of Fuel Chemistry and Technology > 2019 > 47(3): 257-262

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.

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.

Citation:

PDF( 831 KB)

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

LIU Min^{1, 2, 3
,
,},
WANG Yong-gang¹,
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

Funds:

the Beijing Natural Science Foundation BJNSF2182090

Science and Technology Innovation Fund of China Coal Research Institute 2017JC01

More Information

Corresponding author: LIU Min, E-mail: 78562115@qq.com
Received Date: 2018-10-19
Rev Recd Date: 2018-12-02

Available Online: 2021-01-23

Publish Date: 2019-03-10

Abstract

Abstract

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

FullText(HTML)

References(31)

References

[1]	舒歌平, 史士东, 李克健.煤炭液化技术[M].北京:煤炭工业出版社, 2003. SHU Ge-ping, SHI Shi-dong, LI Ke-jian. Direct Coal Liquefaction[M]. Beijing:Coal Industry Press, 2003.
[2]	史士东.煤加氢液化工程学基础[M].北京:化学工业出版社, 2012. SHI Shi-dong. Engineering Basis of Coal Hydro-Liquefaction[M]. Beijing:Chemical Industry Press, 2003.
[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]	刘敏, 史士东, 曲思建, 刘立麟, 盛明, 毛学锋.煤炭直接液化反应机理理论研究进展[J].洁净煤技术, 2015, 21(4):49-54. http://d.wanfangdata.com.cn/Periodical/jjmjs201504015 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. http://d.wanfangdata.com.cn/Periodical/jjmjs201504015
[5]	NEAVEL R. Liquefaction of coal in hydrogen-donor and non-donor vehicles[J]. Fuel, 1976, 55(3):237-242. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=J-STAGE_342644
[6]	贾伟.煤中小分子化合物对煤高温快速液化的影响[D].山西: 太原理工大学, 2010. 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]	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]	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]	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]	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. doi: 10.1080/07349340215011
[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. http://www.sciencedirect.com/science/article/pii/001623619390374B
[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]	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]	陈茺, 高晋生, 颜捷.环己酮抽提煤的研究[J].燃料化学学报, 1997, 25(1):60-64. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=QK199700446117 CHEN Chong, GAO Jin-sheng, YAN Jie. Study on Extraction of coal with cyclohexanone[J]. J Fuel Chem Technol, 1997, 25(1):60-64. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=QK199700446117
[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]	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. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=69c1c1c5829ed2e95e7579e6b391665f
[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]	史权, 赵锁奇, 徐春明, 侯读杰.傅立叶变换离子回旋共振质谱仪在石油组成分析中的应用[J].质谱学报, 2008, 29(6):367-378. http://d.old.wanfangdata.com.cn/Periodical/zpxb200806010 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. http://d.old.wanfangdata.com.cn/Periodical/zpxb200806010
[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]	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]	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]	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]	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]	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]	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]	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. http://www.sciencedirect.com/science/article/pii/002196739280032P
[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. doi: 10.1021/ef9008983
[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]	吴梅, 史军歌, 田松柏.汽油中元素硫的GC-SCD分析方法[J].石油学报(石油加工), 2008, 33(2):320-325. http://d.old.wanfangdata.com.cn/Periodical/syxb-syjg201702017 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. http://d.old.wanfangdata.com.cn/Periodical/syxb-syjg201702017
[30]	黄澎, 张晓静, 毛学锋, 李伟林.神府煤液化油加氢精制过程中硫氮化合物分布的变化[J].燃料化学学报, 2015, 43(12):37-43. http://d.old.wanfangdata.com.cn/Periodical/rlhxxb201601006 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. http://d.old.wanfangdata.com.cn/Periodical/rlhxxb201601006
[31]	李延红.煤液化油中含氮化合物存在形式及分布的研究[D].上海: 华东理工大学, 2014. 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.