Coal desulfurization by single electron transfer reactions

Chatterjee, Kuntal; Wolny, Ryszard; Stock, Leon M.

doi:10.1021/ef00022a012

Cited by 18 publications

(13 citation statements)

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“…However, by raising the reaction temperature well above the melting point of the metals (Table ), biphenyl was formed in essentially quantitative yield. A plausible reaction pathway is shown in Scheme in which intermediate A has been shown to form when DBT is treated with Li at 0 °C in THF . The detection of a trace amount of o -mercaptobiphenyl ( 10 ) in the quenched reaction mixture indicates that A is an intermediate that easily loses M 2 S in the presence of excess alkali metal to form B , which in turn produces biphenyl upon solvolysis.…”

Section: Resultsmentioning

confidence: 99%

Desulfurization of Organosulfur Compounds with Lithium and Sodium

Verkade

1998

Energy Fuels

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Section: Resultsmentioning

confidence: 99%

Desulfurization of Organosulfur Compounds with Lithium and Sodium

Verkade

1998

Energy Fuels

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“…However, lt is pertinent that the mass spectroscopic work on this coal has not provided evidence for aliphatic sulfur compounds (8,9,10 (11,12,13). The product, which was recovered after acid hydrolysis, had less than 0.1% iron, and there were no pyrite reflections in the powder diffraction X-ray spectrum (13). Furthermore, pyrite is absent in the XANES spectrum of this material (3,4).…”

Section: The Sulfur Compoundsmentioning

confidence: 93%

“…6 coals have also concluded that they are relatively rich in aliphatic, sulfidic organic compounds (5,6,7). However, lt is pertinent that the mass spectroscopic work on this coal has not provided evidence for aliphatic sulfur compounds (8,9,10 (11,12,13). The product, which was recovered after acid hydrolysis, had less than 0.1% iron, and there were no pyrite reflections in the powder diffraction X-ray spectrum (13).…”

Section: The Sulfur Compoundsmentioning

confidence: 97%

Organic Desulfurization of Illinois NO. 6 Coal

Stock

Chatterjee

1993

Coal Science and Technology

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This report was prepared as an account of work sponsoredby an agency of the United States Government. Neither the United States Government nor any agency th,_reof,nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise dots not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof.

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“…A MeOH/t-BuLi mixture has been shown to be effective in desulfurizing trienyl and allenyl phenyl sulfoxides. 51 We have found 52 that reactions of polycyclic aromatic sulfur compounds (including BT and DBT) as well as a variety of acyclic organosulfur compounds with lithium or sodium in a hydrocarbon solvent at the comparatively low temperature of 254 and 150 °C, respectively, lead to remarkably effective desulfurization without requiring added hydrogen gas.…”

Section: R10mentioning

confidence: 99%

“…53 It is also known that phenyl benzyl sulfide can be desulfurized to form benzene, toluene and bibenzyl, as well as thiophenol as C-S cleavage products. 51 It is reasonable to suppose that the phenyl anion of PhM formed by cleavage of the aromatic carbon-sulfur bond of Ph 2 S nucleophilically attacks PhSM to eliminate M 2 S and form biphenyl (Scheme 4). If such a nucleophilic reaction is quenched before completion, thiophenol and benzene would be obtained as observed.…”

Section: R10mentioning

confidence: 99%

A Novel Approach to Catalytic Desulfurization of Coal

Verkade¹

2001

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Column chromatographic separation of the S=PBu 3 /PBu 3 product mixture followed by weighing the S=PBu 3 , and by vacuum distillation of S=PBu 3 /PBu 3 mixture followed by gas chromatographic analysis are described. Effects of coal mesh size, pre-treatment with methanol Coal (S) + excess PR 3 Coal + S=PR 3 /PBu 3 and sonication on sulfur removal by PBu 3 revealed that particle size was not observed to affect desulfurization efficiency in a consistent manner. Coal pretreatment with methanol to induce swelling or the addition of a filter aid such as Celite reduced desulfurization efficiency of the PBu 3 and sonication was no more effective than heating. A rationale is put forth for the lack of efficacy of methanol pretreatment of the coal in desulfurization runs with PBu 3 . Coal desulfurization with PBu 3 was not improved in the presence of miniscule beads of molten lithium or sodium as a desulfurizing reagent for SPBu 3 in a strategy aimed at regenerating PBu 3 inside coal pores. Although desulfurization of coals did occur in sodium solutions in liquid ammonia, substantial loss of coal mass was also observed.Of particular concern is the mass balance in the above reaction, a problem which is described in some detail. In an effort to solve this difficulty, a specially designed apparatus is described which we believe can solve this problem reasonably effectively.Elemental sodium was found to remove sulfur quantitatively from a variety of polycyclic organosulfur compounds including dibenzothiophene and benzothiophene under relatively mild conditions (150 0 C) in a hydrocarbon solvent without requiring the addition of a hydrogen donor. Lithium facilitates the same reaction at a higher temperature (254 0 C). Mechanistic pathways are proposed for these transformations. Curiously, dibenzothiophene and its corresponding sulfone was virtually quantitatively desulfurized in sodium solutions in liquid ammonia at -33 0 C, although the yield of biphenyl was only about 20 to 30%. On the other hand, benzothiophene gave a high yield of 2-ethylthiophenol under these conditions. Although our superbase P(MeNCH 2 CH 2 ) 3 N, which is now commercially available, is a more effective desulfurizing agent for a variety of organophosphorus compounds than PPh 3 or its acyclic analogue P(NMe) 3 , it does not desulfurize benzothiophene or dibenzothiophene.ii 95208R10

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Coal desulfurization by single electron transfer reactions

Cited by 18 publications

References 0 publications

Desulfurization of Organosulfur Compounds with Lithium and Sodium

Desulfurization of Organosulfur Compounds with Lithium and Sodium

Organic Desulfurization of Illinois NO. 6 Coal

A Novel Approach to Catalytic Desulfurization of Coal

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