Study of hydroxyaromatic compounds from coal derived liquids : global characterization by distillation, anion exchange separation, titration, 1H NMR, mass spectrometry and functional group determination

Zanella, Igor Giacomelli; Weber, JH; Grüber, R.; Cagniant, D.

doi:10.1016/0378-3820(88)90005-7

Cited by 3 publications

(1 citation statement)

References 10 publications

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“…Phenolics are the major oxygen-containing compounds in coal tar and brown-coal-derived liquids . Of those, the alkyl phenols are dominant. , Other oxygen-containing compounds that have been found include tetralinol, indanol, hexahydrofluorenol, fluorenol, hydroxybiphenyl, and dihydroxybenzene. ,,, The high viscosity of coal-derived asphaltenes is likely due to intermolecular aggregation from hydrogen bonding of phenolic compounds. Therefore, when the phenol content in the asphaltenes fraction is decreased, the viscosity of coal-derived liquids will also be reduced …”

Section: Introductionmentioning

confidence: 99%

Identification of Dihydroxy Aromatic Compounds in a Low-Temperature Pyrolysis Coal Tar by Gas Chromatography−Mass Spectrometry (GC−MS) and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)

Shi

Yan

et al. 2010

Energy Fuels

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Dihydroxy aromatics in coal tar undergo rapid coupling reactions with each other and with some coalderived species during coal pyrolysis and liquefaction. However, only limited information on the structure of dihydroxy aromatics is known. In this study, Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) and gas chromatography-mass spectrometry (GC-MS) were used to characterize the dihydroxy aromatics in a low-temperature pyrolyzed coal tar and its distillate and residue fractions. Negative-ion electrospray ionization (ESI) FT-ICR MS spectra of coal-tar-derived samples had low molecular masses and narrow mass ranges. Negative-ion ESI is extremely selective for the dihydroxy aromatics present in coal tar. The O 2 class species had the highest ion intensity among the species in the negative-ion FT-ICR mass spectrum for each sample. Dihydroxy compounds with an aromatic core structure of benzene, indan, biphenyl (and/or acenaphthene), and naphthalene were identified in the distillate fractions. Dihydroxy compounds in the residue fraction were dihydroxy fluorenes and phenanthrenes (and/or anthracenes). The O 2 class species with relatively high molecular masses were likely dihydroxy acenaphthylenes and/or hydroxy dibenzofurans but could not be distinguished from each other because these compounds have the same molecular mass.

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Section: Introductionmentioning

confidence: 99%

Identification of Dihydroxy Aromatic Compounds in a Low-Temperature Pyrolysis Coal Tar by Gas Chromatography−Mass Spectrometry (GC−MS) and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)

Shi

Yan

et al. 2010

Energy Fuels

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GC–MS analysis of phenolic compounds in fuels after conversion to trifluoroacetate esters

Green

Vrana

1994

J. High Resol. Chromatogr.

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The GC-MS characteristics of trifluoroacetate esters of phenolic compounds are discussed. Linear temperature programmed retention indices and total ion current MS response factors of over 120 phenolic esters are reported.The main GC advantages from analysis of trifluoroacetate esters as compared to plain phenols are enhanced volatility and improved resolution. For example, the elution temperature of a given phenol is typically 50 "C greater than that of the corresponding trifluoroacetate ester. Also, while retention of compounds with two trifluoroacetate groups is only moderately greater than mono esters, underivatized dihydroxy compounds are very difficult to elute from any GC column. Complete resolution of isomeric Co-, Ci-and Cn-alkylphenol esters is readily achieved on conventional fused silica GC columns; resolution of the corresponding underivatized compounds requires specialized GC columns with low temperature limits.In general, mass spectra of trifluoroacetate esters are more characteristic of a given structure than those of the corresponding phenols and may be more rigorously interpreted towards structural elucidation. A table in the report summarizes some of the more important spectral features used in compound identification.Example applications in analysis of coal-, shale-and petroleum-derived materials are presented. Selected ion monitoring is used to determine individual phenolic components in whole distillates; reconstructed ion chromatograms are used to illustrate distributions of selected species as a function of fuel storage and thermal stress.

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Extraction of tar acids with glycols

Tiwari

1991

Fuel Processing Technology

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Study of hydroxyaromatic compounds from coal derived liquids : global characterization by distillation, anion exchange separation, titration, 1H NMR, mass spectrometry and functional group determination

Cited by 3 publications

References 10 publications

Identification of Dihydroxy Aromatic Compounds in a Low-Temperature Pyrolysis Coal Tar by Gas Chromatography−Mass Spectrometry (GC−MS) and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)

Identification of Dihydroxy Aromatic Compounds in a Low-Temperature Pyrolysis Coal Tar by Gas Chromatography−Mass Spectrometry (GC−MS) and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)

GC–MS analysis of phenolic compounds in fuels after conversion to trifluoroacetate esters

Extraction of tar acids with glycols

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