Comparison of methods for the isolation of basic nitrogen compounds from coal tars

Burchill, Paul; Herod, Alan A.; Mahon, Judith P.; Pritchard, Ernest

doi:10.1016/s0021-9673(01)96719-6

Cited by 38 publications

(17 citation statements)

References 14 publications

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“…The existence of isomers in the extracts was confirmed by the apparent difference in retention time shown in Supporting Information Table S2. Retention times of isomers are dependent on the strength of reversible intermolecular forces originated from the functional groups, the stereostructure of molecules, the nature of bonded stationary phase and the polarity of eluting solvent . Two chromatographic peaks of C 40 H 69 N are shown in Supporting Information Fig.…”

Section: Resultsmentioning

confidence: 99%

Sequential ultrasonic extraction of a Chinese coal and characterization of nitrogen‐containing compounds in the extracts using high‐performance liquid chromatography with mass spectrometry

Xia

Fan

You

et al. 2016

J of Separation Science

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Dongming lignite was sequentially extracted with petroleum ether, carbon disulfide, methanol, acetone, and isometric carbon disulfide/acetone mixed solvent at room temperature to afford extracts 1-5, respectively. High-performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry was used to separate and characterize heteroatomic species in the extracts at molecular level. Molecular mass of compounds in the extracts is mainly distributed from 300 to 800 u, and the relative abundance of compounds with molecular mass over 800 u in the carbon disulfide extract is 135 times of that in the petroleum ether extract. The acetone extract has the highest relative abundance for organonitrogen compounds. Double bond equivalence numbers of detected species indicate that most of the organonitrogen compounds contain N-heterocyclic aromatic rings, including pyridine, quinoline and pyrrole. Some organonitrogen isomers in Dongming lignite were separated and identified by high-performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry, and the corresponding structural information was proposed.

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Section: Resultsmentioning

confidence: 99%

Sequential ultrasonic extraction of a Chinese coal and characterization of nitrogen‐containing compounds in the extracts using high‐performance liquid chromatography with mass spectrometry

Xia

Fan

You

et al. 2016

J of Separation Science

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“…Figure S10A (supporting information) shows the extracted ion chromatogram of C 24 H 41 N 1 O 1 from SP 3 . The existence of two isomers of C 24 H 41 N 1 O 1 in SP 3 was confirmed by the obvious difference in retention time, which is related to the partition coefficient of compounds with different functional groups in the stationary phase and mobile phase, and also to the steric structure of molecules, the nature of the bonded stationary phase and the polarity of the mobile phase 42 . The DBE value of C 24 H 41 N 1 O 1 is 5, and the corresponding structure may be a pyridine ring with different alkyl groups, which may result in the difference in retention time.…”

Section: Resultsmentioning

confidence: 94%

Sequential thermal dissolution of two low‐rank coals and characterization of their structures by high‐performance liquid chromatography/time‐of‐flight mass spectrometry and gas chromatography/mass spectrometry

Cao

Fan

Xia

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Gas chromatography/mass spectrometry (GC/MS) and high‐performance liquid chromatography/time‐of‐flight mass spectrometry (HPLC/TOF‐MS) were used to separate and reveal the molecular characteristics of organic matter in low‐rank coals. Methods Six soluble portions (SPs) were obtained by sequential thermal dissolution (TD) of two low‐rank coals in the order of cyclohexane, acetone and methanol solvents at 300°C. Organic matter with different molecular characteristics were enriched in eachTD extract, which was further separated and analyzed by GC/MS and HPLC/TOF‐MS using an electrospray ionization source in positive mode to obtain a comprehensive understanding of the structural composition of coals. Results Low polarity compounds like alkanes and arenes have a better solubility in cyclohexane. Phorone has the highest relative abundance in the acetone SPs, and the main compounds detected in the methanol SPs are alcohols and phenols. According to the data from HPLC/TOF‐MS, most of the oxygen atoms are in the form of carbonyl and alkoxy groups. The nitrogen‐containing compounds in SPs are mainly saturated aliphatic amines and pyridines. The sulfur‐containing compounds mainly exist in the form of thioalkanes and thiophenes. Conclusions Non‐destructive methods were used to obtain soluble matter from coals, and different chromatographic and mass spectrometric techniques were used to separate and analyze the organic matter in coals. Detailed molecular structural information was obtained for the efficient and clean utilization of low‐rank coals.

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“…Nitrogen detection is subject to interference with the hydrocarbons of the matrix [91]. Therefore, different techniques of isolation of N-compounds from coal tar are traditionally carried out by aqueous acid extraction [49,50] precipitation with gaseous hydrogen chloride [117], solvent extraction with methanol [118], and cation-exchange chromatography [119,120].…”

Section: Nitrogen Containing Compounds In Coal Tarmentioning

confidence: 99%

Comprehensive Two-Dimensional Gas Chromatography and Its Application to the Investigation of Pyrolytic Liquids

Maciel¹,

Silva²,

Bispo³

et al. 2017

Pyrolysis

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The chapter presents basic principles of one-dimensional gas chromatography (1D-GC) and comprehensive two-dimensional gas chromatography (GC × GC) related to the main advantages of the two-dimensional technique, as well as its application to the study of organic compounds in liquids derived from coal, mainly through pyrolysis and extraction. It also shows the investigation of compounds contained in bio-oils obtained from biomass through pyrolysis, using GC × GC. Advances in scientific knowledge related to the composition of these complex matrices are shown through different examples of GC × GC analyses, such as the identification of trace compounds that would not be perceived by 1D-GC, organized patterns of elution of structurally related compounds that help their identification, etc. Examples shown make it clear that GC × GC is the technique of choice to elucidate composition of these complex matrices.

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Comparison of methods for the isolation of basic nitrogen compounds from coal tars

Cited by 38 publications

References 14 publications

Sequential ultrasonic extraction of a Chinese coal and characterization of nitrogen‐containing compounds in the extracts using high‐performance liquid chromatography with mass spectrometry

Sequential ultrasonic extraction of a Chinese coal and characterization of nitrogen‐containing compounds in the extracts using high‐performance liquid chromatography with mass spectrometry

Sequential thermal dissolution of two low‐rank coals and characterization of their structures by high‐performance liquid chromatography/time‐of‐flight mass spectrometry and gas chromatography/mass spectrometry

Comprehensive Two-Dimensional Gas Chromatography and Its Application to the Investigation of Pyrolytic Liquids

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