Constitution of Illinois No. 6 Argonne Premium Coal: A Review

Castro-Marcano, Fidel; Mathews, Jonathan P.

doi:10.1021/ef1015846

Cited by 35 publications

(17 citation statements)

References 83 publications

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“…6 coal and Pocahontas No. 3 coal by (−) ESI FT-ICR MS. 18,19 Comparison of these two coal extracts revealed higher levels of O 2 and NO 2 species in both coal samples and showed different degrees of alkylation between coal compounds from different geological origins. 18 The Illinois coal No.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Previous reports suggest that the heptane-insoluble/toluene-soluble compounds (asphaltene fraction) from coal-derived liquids are smaller in size, with fewer fused aromatic rings than petroleum asphaltenes. 5,6 Others claim that island structures are the sole motif in coalderived asphaltenes, regardless of their molecular weight, heteroatom content, and/or geological origin. 6 studies report that the most abundant species from coalderived and petroleum asphaltenes contain a similarly sized aromatic core; however, coal-derived asphaltenes generally exhibit shorter alkyl side chains, accounting for the discrepancy between coal and petroleum asphaltene molecular sizes.…”

Section: ■ Introductionmentioning

confidence: 99%

“…5,6 Others claim that island structures are the sole motif in coalderived asphaltenes, regardless of their molecular weight, heteroatom content, and/or geological origin. 6 studies report that the most abundant species from coalderived and petroleum asphaltenes contain a similarly sized aromatic core; however, coal-derived asphaltenes generally exhibit shorter alkyl side chains, accounting for the discrepancy between coal and petroleum asphaltene molecular sizes. 8,9 Prior research also suggests that coal-derived asphaltenes are enriched in more cata-condensed structures than pericondensed cores, compared with petroleum asphaltenes.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The Illinois coal No. 6 sample has previously been demonstrated to be the most chemically diverse coal sample from the Argonne coal supply and thus is widely used as a coal standard. − ,− However, much remains unknown about the asphaltene fraction of unmodified coal extracts and whether they contain archipelago asphaltenes similar to those in petroleum. It is important to point out that the molecular-level characterization of coal is difficult because of its high oxygen content, even for maltenes ( n -heptane/toluene-soluble).…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive Compositional and Structural Comparison of Coal and Petroleum Asphaltenes Based on Extrography Fractionation Coupled with Fourier Transform Ion Cyclotron Resonance MS and MS/MS Analysis

et al. 2020

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A recently developed extrography separation method fractionates petroleum asphaltenes based on their ionization efficiency, which correlates with polarity, aggregation tendency, and asphaltene structure (single-core or island versus multicore or archipelago). Archipelago asphaltenes were recently demonstrated to coexist with island structures in a variety of petroleum samples; however, archipelago compounds ionize much less efficiently than island compounds, making the former difficult to observe by mass spectrometry without prior separation. Highly processed coal-derived asphaltenes have been studied previously to reveal only small, single-core structure asphaltenes; however, the structure(s) of asphaltenes from unaltered coal extracts has not been extensively studied. Thus, this work focuses on the application of the extrography separation to an unaltered Illinois coal No. 6 asphaltene extract to reveal the coexistence of island and archipelago structural motifs by positive-ion (+) atmospheric pressure photoionization (APPI) Fourier transform ion cyclotron resonance mass spectrometry. Asphaltenes from a Wyoming crude oil sample are also characterized for comparison with coal asphaltenes. The results reveal that Wyoming crude oil asphaltenes contain mainly island species, whereas coal asphaltenes contain archipelago and island compounds with high oxygen content. The structural analysis is enabled by a new "multinotch" stored-waveform inverse Fourier transform isolation, which selectively isolates high-aromaticity precursor ions at each of several nominal mass ranges prior to fragmentation by infrared multiphoton dissociation, and enables unambiguous determination of island versus archipelago species in samples that contain compounds with high and low aromaticity. The more polarizable fractions from each asphaltene sample reveal low-aromaticity polyfunctional oxygenated species, with a solubility behavior consistent with asphaltenes but a compositional range typical of maltenes. These atypical asphaltene species, which ionize poorly, are hypothesized to participate in multiple hydrogen bonding interactions and thus exhibit strong adsorption on polar stationary phases such as SiO 2 . Furthermore, these polarizable polyfunctional species ionize preferentially as protonated cations by (+) APPI, accounting for their capability to hydrogen-bond in solution. Collectively, the results demonstrate the existence of archipelago structures in both coal and petroleum asphaltenes, along with polyoxygenated species with low aromaticity that behave like asphaltenes in terms of solubility, because they can establish stronger intermolecular forces such as hydrogen bonding.

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Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Comprehensive Compositional and Structural Comparison of Coal and Petroleum Asphaltenes Based on Extrography Fractionation Coupled with Fourier Transform Ion Cyclotron Resonance MS and MS/MS Analysis

et al. 2020

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“…Natural abundance 15 N and 13 C NMR spectra of the IHSS samples, including 13 C aromaticities (f a ’s), have been reported [ 26 , 27 ]. Illinois #6 coal (high volume bituminous) was purchased as the powder from the Argonne Premium Coal Samples collection at Argonne National Laboratory [ 28 , 29 ]. Natural abundance 15 N and 13 C NMR spectra of the coal, including the 13 C aromaticity, have also been reported [ 30 , 31 ].…”

Section: Methodsmentioning

confidence: 99%

Nitrosation and Nitration of Fulvic Acid, Peat and Coal with Nitric Acid

Thorn

Cox

2016

PLoS ONE

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Nitrohumic acids, produced from base extraction of coals and peats oxidized with nitric acid, have received considerable attention as soil ammendments in agriculture. The nitration chemistry however is incompletely understood. Moreover, there is a need to understand the reaction of nitric acid with natural organic matter (NOM) in general, in the context of a variety of environmental and biogeochemical processes. Suwannee River NOM, Suwannee River fulvic acid, and Pahokee Peat fulvic acid were treated with 15N-labeled nitric acid at concentrations ranging from 15% to 22% and analyzed by liquid and solid state 15N NMR spectroscopy. Bulk Pahokee peat and Illinois #6 coal were also treated with nitric acid, at 29% and 40% respectively, and analyzed by solid state 15N NMR spectroscopy. In addition to nitro groups from nitration of aromatic carbon, the 15N NMR spectra of all five samples exhibited peaks attributable to nitrosation reactions. These include nitrosophenol peaks in the peat fulvic acid and Suwannee River samples, from nitrosation of phenolic rings, and N-nitroso groups in the peat samples, from nitrosation of secondary amides or amines, the latter consistent with the peat samples having the highest naturally abundant nitrogen contents. Peaks attributable to Beckmann and secondary reactions of the initially formed oximes were present in all spectra, including primary amide, secondary amide, lactam, and nitrile nitrogens. The degree of secondary reaction product formation resulting from nitrosation reactions appeared to correlate inversely with the 13C aromaticities of the samples. The nitrosation reactions are most plausibly effected by nitrous acid formed from the reduction of nitric acid by oxidizable substrates in the NOM and coal samples.

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