Citation: CONG Xing-shun, ZONG Zhi-min, ZHOU Yin, LI Min, ZHAO Yun-peng, FAN Xing, WEI Xian-yong. Enrichment and analysis of long-chain normal alkanals from Zhundong subbituminous coal[J]. Journal of Fuel Chemistry and Technology, ;2014, 42(3): 257-261. shu

Enrichment and analysis of long-chain normal alkanals from Zhundong subbituminous coal

1.
1. Key Laboratory of Coal Processing and Efficient Utilization (Ministry of Education), China University of Mining & Technology, Xuzhou 221116, China;

Corresponding author: ZONG Zhi-min,
Received Date: 11 November 2013
Available Online: 3 January 2014
Fund Project: National Basic Research Program of China (973 Program, 2011CB201302) (973 Program, 2011CB201302) the Key Project of Natural Science Foundation of China (20936007) (20936007) the Fund from Natural Science Foundation of China for Innovative Research Group (51221462) (51221462) the Key Project of Coal Joint Fund from Natural Science Foundation of China and Shenhua Group Corporation Limited (51134021) (51134021) The Strategic Chinese-Japanese Joint Research Program (2013DFG60060) (2013DFG60060) National Natural Science Foundation of China (51074153) (51074153) National Natural Science Foundation of China for Young Researchers (21206187 and 21206188) (21206187 and 21206188)

Zhundong subbituminous coal was exhaustively extracted with isometric carbon disulfide (CDS) and acetone mixed solvent. The extract was fractionated with petroleum ether (PE) and CDS into PE-extractable portion (E₁) and CDS-extractable portion (E₂). E₂ was sequentially eluted with PE and 30% CDS/PE mixed solvent through a silica gel-packed column. A series of long-chain normal alkanals (LCNAs, C_18~27) were enriched from E₂ and identified with a gas chromatography/mass spectrometer. The fractional extraction and subsequent column chromatography provide an effective approach for enriching LCNAs from middle-and low-rank coals. LCNAs could be a class of important biomarkers.
- long-chain normal alkanals,
- Zhundong subbituminous coal,
- fractional extraction,
- column chromatography
1. [1]
  [1] WEI X Y, WANG X H, ZONG Z M, NI Z H, ZHANG L F, JI Y F, XIE K C, WEE LEE C, LIU Z X, CHU N B, CUI J Y. Identification of organochlorines and organobromines in coals[J]. Fuel, 2004, 83(17/18): 2435-2438.
2. [2]
  [2] SUN L B, ZONG Z M, KOU J H, CAO J P, YU G Y, ZHAO W, LI B M, LEE C W, XIE K C, WEI X Y. Identification of organic chlorines and iodines in the extracts from hydrotreated Argonne Premium coal residues[J]. Energy Fuels, 2007, 21(4): 2238-2239.
3. [3]
  [3] DING M J, ZONG Z M, ZONG Y, OU-YANG X D, HUANG Y G, ZHOU L, WANG F, CAO J P, WEI X Y. Isolation and identification of fatty acid amides from Shengli coal[J]. Energy Fuels, 2008, 22(4): 2419-2421.
4. [4]
  [4] DING M J, LI W D, XIE R L, ZONG Y, CAI K Y, PENG Y L, ZONG Z M, WEI X Y. Separation and analysis of aromatic hydrocarbons from two Chinese coals[J]. J China Univ Min Technol, 2008, 18(3): 432-436.
5. [5]
  [5] ZONG Y, ZONG Z M, DING M J, ZHOU L, HUANG Y G, ZHENG Y X, JIN X, MA Y M, WEI X Y. Separation and analysis of organic compounds in an Erdos coal[J]. Fuel, 2009, 88(3): 469-474.
6. [6]
  [6] CHAFFEE A L, FOOKES C J R. Polycyclic aromatic hydrocarbons in Australian coals—Ⅲ. Structural elucidation by proton nuclear magnetic resonance spectroscopy[J]. Org Geochem, 1988, 12(3): 261-271.
7. [7]
  [7] CHANG H-C K, NISHIOKA M, BARTLE K D, WISE S A, BAYONA J M, MARKIDES K E, LEE M L. Identification and comparison of low-molecular-weight neutral constituents in two different coal extracts[J]. Fuel, 1988, 67(1): 45-57.
8. [8]
  [8] WEI X Y, WANG X H, ZONG Z M. Extraction of organonitrogen compounds from five Chinese coals with methanol[J]. Energy Fuels, 2009, 23(10): 4848-4851.
9. [9]
  [9] HAZAI I, ALEXANDER G, SZ KELY T, ESSIGER B, RADEK D. Investigation of hydrocarbon constituents of a young sub-bituminous coal by gas chromatography-mass spectrometry[J]. J Chromatogr A, 1986, 367: 117-133.
10. [10]
  [10] HAYATSU R, MCBETH R L, NEILL P H, XIA Y, WINANS R E. Terpenoid biomarkers in Argonne Premium coal samples and their role during coalification[J]. Energy Fuels, 1990, 4(5): 456-463.
11. [11]
  [11] WANG T G, SIMONEIT B R T, PHILP R P, YU C P. Extended 8β(H)-drimane and 8,14-secohopane series in a Chinese boghead coal[J]. Energy Fuels, 1990, 4(2): 177-183.
12. [12]
  [12] ZHOU J, ZONG Z M, CHEN B, YANG Z S, LI P, LU Y, YUE X M, CONG X S, WEI Y B, WANG Y G, FAN X, ZHAO Y P, WEI X Y. The enrichment and identification of methyl alkanones from thermally soluble Shengli lignite[J]. Energy Sources, Part A, 2013, 35(23): 2218-2224.
13. [13]
  [13] LIU Z W, ZONG Z M, LI J N, CHEN C F, JIANG H, PENG Y L, XUE J Q, YANG X L, ZHENG Y X, ZHOU X, XIE R L, WEI X Y. Isolation and identification of two bis(2-ethylheptyl) benzenedicarboxylates from Lingwu coal[J]. Energy Fuels, 2008, 23(1): 588-590.
14. [14]
  [14] LIU Z W, WEI X Y, ZONG Z M, LI J N, XUE J Q, CHEN X F, CHEN F J. Isolation and identification of methyl alkanoates from Lingwu coal[J]. Energy Fuels, 2010, 24(4): 2784-2786.
15. [15]
  [15] SHI D L, WEI X Y, CHEN B, ZONG Z M, ZHAO Y P, FAN X, HOU J N. The enrichment of condensed arenes in Geting bituminous coal[J]. Energy Sources, Part A, 2013, 35(20): 1898-1904.
16. [16]
  [16] SHI D L, WEI X Y, FAN X, ZONG Z M, CHEN B, ZHAO Y P, WANG Y G, CAO J P. Characterizations of the extracts from Geting bituminous coal by spectrometries[J]. Energy Fuels, 2013, 27(7): 3709-3717.
17. [17]
  [17] WILS E R J, HULST A G, DEN HARTOG J C. The occurrence of plant wax constituents in airborne particulate matter in an urbanized area[J]. Chemosphere, 1982, 11(11): 1087-1096.
18. [18]
  [18] GILPIN J A, MCLAFFERTY F W. Mass spectrometric analysis aliphatic aldehydes[J]. Anal Chem, 1957, 29(7): 990-994.
19. [19]
  [19] CHRISTIANSEN K, MAHADEVAN V, VISWANATHAN C V, HOLMAN R T. Mass spectrometry of long-chain aliphatic aldehydes, dimethyl acetals and alk-1-enyl ethers[J]. Lipids, 1969, 4(6): 421-427.
20. [20]
  [20] 葛岭梅, 薛韩玲, 徐精彩, 邓军, 张辛亥. 对煤分子中活性基团氧化机理的分析[J]. 煤炭转化, 2001, 24(3): 23-28.
21. [21]
  (GE Ling-mei, XUE Han-ling, XU Jing-cai, DENG Jun, ZHANG Xin-hai. Study on the oxidation mechanism of active groups of coal[J]. Coal Conversion, 2001, 24(3): 23-28.)
22. [22]
  [21] LAMBERTON J. The long-chain aldehydes of sugar-cane wax[J]. Aust J Chem, 1965, 18(6): 911-913.
23. [23]
  [22] KRANZ Z, LAMBERTON J, MURRAY K, REDCLIFFE A. Sugar-cane wax. Ⅱ. An examination of the constituents of sugar-cane cuticle wax by gas chromatography[J]. Aust J Chem, 1960, 13(4): 498-505.
24. [24]
  [23] CORMIER M J, STREHLER B L. The identification of KCF: Requirement of long-chain aldehydes for bacterial extract luminescence[J]. J Am Chem Soc, 1953, 75(19): 4864-4865.
25. [25]
  [24] STREHLER B L, CORMIER M J. Isolation, identification, and function of long chain fatty aldehydes affecting the bacterial luciferin-luciferase reaction[J]. J Biol Chem, 1954, 211(1): 213-225.
26. [26]
  [25] GRAY G M. The separation of the long chain fatty aldehydes by gas-liquid chromatography[J]. J Chromatogr A, 1960, 4: 52-59.
27. [27]
  [26] O'BRIEN J S, SAMPSON E L. Fatty acid and fatty aldehyde composition of the major brain lipids in normal human gray matter, white matter, and myelin[J]. J Lipid Res, 1965, 6(4): 545-551.
28. [28]
  [27] PRAHL F G, PINTO L A. A geochemical study of long-chain n-aldehydes in Washington coastal sediments[J]. Geochim Cosmochim Acta, 1987, 51(6): 1573-1582.
29. [29]
  [28] ALBAIG S J, ALGABA J, GRIMALT J. Extractable and bound neutral lipids in some lacustrine sediments[J]. Org Geochem, 1984, 6: 223-236.
30. [30]
  [29] GSCHWEND P M, ZAFIRIOU O C, MANTOURA R F C, SCHWARZENBACH R P, GAGOSIAN R B. Volatile organic compounds at a coastal site. 1. Seasonal variations[J]. Environ Sci Technol, 1982, 16(1): 31-38.
31. [31]
  [30] IINO M, KUMAGAI J, ITO O. Coal extractions with carbon disulfide-N-methyl-2-pyrrolidone mixture at room temperature[J]. J Fuel Soc of Jpn, 1985, 64(3): 210-212.
32. [32]
  [31] ZONG Z M, PENG Y L, QIN Z H, LIU J Z, WU L, WANG X H, LIU Z G, ZHOU S L, WEI X Y. Reaction of N-methyl-2-pyrrolidinone with carbon disulfide[J]. Energy Fuels, 2000, 14(3): 734-735.
1. [1]
  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
2. [2]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
3. [3]
  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
4. [4]
  Qilong Fang , Yiqi Li , Jiangyihui Sheng , Quan Yuan , Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004
5. [5]
  Chenye An , Abiduweili Sikandaier , Xue Guo , Yukun Zhu , Hua Tang , Dongjiang Yang . 红磷纳米颗粒嵌入花状CeO₂分级S型异质结高效光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2405019-. doi: 10.3866/PKU.WHXB202405019
6. [6]
  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
7. [7]
  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
8. [8]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
9. [9]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
10. [10]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
11. [11]
  Yingying Chen , Di Xu , Congmin Wang . Exploration and Practice of the “Four-Level, Three-Linkage” General Chemistry Course System. University Chemistry, 2024, 39(8): 119-125. doi: 10.3866/PKU.DXHX202401057
12. [12]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
13. [13]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
14. [14]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
15. [15]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
16. [16]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
17. [17]
  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
18. [18]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1237)
HTML views(150)

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