Isolation and Identification of 3-Ethyl-8-methyl-2,3-dihydro-1<i>H</i>-cyclopenta[<i>a</i>]chrysene from Shengli Lignite

Cong, Xing‐Shun; Zong, Zhi‐Min; Zhou, Yin; Li, Min; Wang, Wanli; Li, Fenggang; Zhou, Jun; Fan, Xing; Zhao, Yun‐Peng; Wei, Xian‐Yong

doi:10.1021/ef402403y

Cited by 25 publications

(13 citation statements)

References 40 publications

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“…A deep insight into the chemical structures of coals is significantly important for efficient utilization of coals, especially for obtaining value-added chemicals from coals [3][4][5]. Coals are too complex to be elaboratively characterized.…”

Section: Introductionmentioning

confidence: 99%

Insight into the structural features of Zhaotong lignite using multiple techniques

Wei

Yan

et al. 2015

Fuel

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198

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Section: Introductionmentioning

confidence: 99%

Insight into the structural features of Zhaotong lignite using multiple techniques

Wei

Yan

et al. 2015

Fuel

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198

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“…The n ‐alkanes, arenes, and methyl alkanoates are detected in the extracts both from coal extraction and thermal dissolution, while most of the n ‐alkenes, phenols, methyl alkanones, ethyl alkanoates, dimethyl alkanedioates, and diethyl alkanedioates appear in the extracts from thermal dissolution. As shown in Table , some valuable chemicals with high purity (>90%) are separated from coals through low‐temperature extraction followed by column chromatography and/or medium pressure liquid chromatography (Liu et al, , ; Zong et al, ; Cong et al, ,c). Their molecular structures are determined by GC/MS combined with other analytical techniques.…”

Section: Small‐molecular Chemicals In Cdls Identified By Gc/msmentioning

confidence: 99%

Application of mass spectrometry in the characterization of chemicals in coal‐derived liquids

Liu

Fan

Wei

et al. 2016

Mass Spectrometry Reviews

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Coal-derived liquids (CDLs) are primarily generated from pyrolysis, carbonization, gasification, direct liquefaction, low-temperature extraction, thermal dissolution, and mild oxidation. CDLs are important feedstocks for producing value-added chemicals and clean liquid fuels as well as high performance carbon materials. Accordingly, the compositional characterization of chemicals in CDLs at the molecular level with advanced analytical techniques is significant for the efficient utilization of CDLs. Although reviews on advancements have been rarely reported, great progress has been achieved in this area by using gas chromatography/mass spectrometry (GC/MS), two-dimensional GC-time of flight mass spectrometry (GC × GC-TOFMS), and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). This review focuses on characterizing hydrocarbon, oxygen-containing, nitrogen-containing, sulfur-containing, and halogen-containing chemicals in various CDLs with these three mass spectrometry techniques. Small molecular (< 500 u), volatile and semi-volatile, and less polar chemicals in CDLs have been identified with GC/MS and GC × GC-TOFMS. By equipped with two-dimensional GC, GC × GC-TOFMS can achieve a clearly chromatographic separation of complex chemicals in CDLs without prior fractionation, and thus can overcome the disadvantages of co-elution and serious peak overlap in GC/MS analysis, providing much more compositional information. With ultrahigh resolving power and mass accuracy, FT-ICR MS reveals a huge number of compositionally distinct compounds assigned to various chemical classes in CDLs. It shows excellent performance in resolving and characterizing higher-molecular, less volatile, and polar chemicals that cannot be detected by GC/MS and GC × GC-TOFMS. The application of GC × GC-TOFMS and FT-ICR MS to chemical characterization of CDLs is not as prevalent as that of petroleum and largely remains to be developed in many respects. © 2016 Wiley Periodicals, Inc. Mass Spec Rev 36:543-579, 2017.

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“…Many traditional separation methods, including column chromatography, , solvent extraction, , and distillation, and recently developed techniques, such as supercritical CO 2 extraction, extraction with switchable hydrophilicity solvent, reactive extraction, molecular distillation, and phase separation by hydrophilic surfactants, were used to isolate pure organic compounds and/or group components from bio-oil . Among them, column chromatography is the most effective approach to isolate high-pure compounds and group components from extremely complex mixtures such as heavy oil, coal tar, crude bio-oil, and coal extract. − Using this method, many group components such as p -bis(2,6-dimethoxyphenol)yl compounds, ketones, long-chain fatty acid amides and arenes, and even some high-pure compounds including syringol and acetosyringone, and hazardous phthalate esters, were isolated from bio-oil. However, to the best of our knowledge, no report has been issued on the enrichment of difunctional ethyl esters (DFEEs, including dibasic acid diethyl esters and ω-hydroxy ethyl esters) from any bio-oils thus far.…”

Section: Introductionmentioning

confidence: 99%

Isolation and Identification of Six Difunctional Ethyl Esters from Bio-oil and Their Special Mass Spectral Fragmentation Pathways

Liu

Cong

et al. 2018

Energy Fuels

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Three difunctional ethyl esters (DFEEs), including ethyl 16-hydroxyhexadecanoate, ethyl (Z)-18-hydroxyoctadec-9-enoate, and diethyl (Z)-octadec-9-ene-1,18-dioate, were isolated as nearly pure compounds from sawdust-derived bio-oil. Their structures were tentatively identified by gas chromatography/mass spectrometry (GC/MS) and high-resolution mass spectrometry (HR-MS). Combination transesterification reaction of DFEEs to difunctional methyl esters (DFMEs) and determination of the GC/MS retention time differences of DFEEs and corresponding DFMEs is a simple method to determine the ester group number of unknown DFEEs. GC/MS results indicate that the fragment ions at mass-to-charge ratios (m/z) of 88 and 98 are typical ions for these DFEEs. The former ion is formed via well-known McLafferty rearrangement, whereas the formation pathway of the ion at m/z 98 is unreported before. HR-MS results show that the fragment ion at m/z 98 should be a cyclohexanone radical ion, which is possibly formed via a novel rearrangement initiated by remote hydrogen rearrangement. Besides long-chain DFEEs, long-chain difunctional carboxylic acids (including dicarboxylic acids, ω-hydroxy acids, diacid monomethyl ester, and diacid monoethyl ester) and DFMEs (including diacid dimethyl ester and ω-hydroxy methyl ester) are also typical of the fragment ion at m/z 98. Hence, it is a common characteristic to form the rearrangement ion at m/z 98 for long-chain difunctional carboxylic acids, DFEEs, and DFMEs, and this special mass spectral rearrangement could facilitate the identification of these classes of compounds. Using this rearrangement rule of DFEEs, three ω-hydroxy ethyl esters, including ethyl 22-hydroxydocosanoate, ethyl 24-hydroxytetracosanoate, and ethyl 26-hydroxyhexacosanoate, were tentatively identified by GC/MS.

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Isolation and Identification of 3-Ethyl-8-methyl-2,3-dihydro-1H-cyclopenta[a]chrysene from Shengli Lignite

Cited by 25 publications

References 40 publications

Insight into the structural features of Zhaotong lignite using multiple techniques

Insight into the structural features of Zhaotong lignite using multiple techniques

Application of mass spectrometry in the characterization of chemicals in coal‐derived liquids

Isolation and Identification of Six Difunctional Ethyl Esters from Bio-oil and Their Special Mass Spectral Fragmentation Pathways

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