Über die Kontakt‐Kondensation des Acetylens

Zelinsky, N. D.

doi:10.1002/cber.19240570219

Cited by 15 publications

(3 citation statements)

References 8 publications

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“…Carboxyl groups were converted to methyl groups to facilitate separation and identification. Different methods for this conversion involving rather harsh conditions have been described in the past (36)(37)(38)(39)(40)(41)(42)(43). To minimize structural rearrangements while obtaining nearly quantitative conversions, the three-step transformation (44, 45) outlined in Figure 2 was developed for a mixture of crude oil carboxylic acids.…”

Section: Sulfur Compounds Benzdinaphthenesmentioning

confidence: 99%

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

Seifert¹,

Teeter²,

Howells³

et al. 1969

Anal. Chem.

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A new and comprehensive approach has been developed for the identification of carboxylic acids in virgin crude oil. Knowledge of the structures of these acids is relevant to questions concerning the origin of petroleum and the origin of life. The identification involves initial conversion of acids, via the corresponding alcohols and their p-toluene sulfonate esters, to hydrocarbons. The hydrocarbons are separated by a combination of silica gel and gel permeation chromatography and identified by ultraviolet, infrared, and high resolution mass spectrometry. For the acidhydrocarbon conversion, proof was obtained for the maintenance, on an average statistical basis, of most of the carbon skeletal structures of the original acids. The structure determination of the hydrocarbons and the retention of carbon skeleton during conversion permits identification of many classes of carboxylic acids not previously discovered in virgin crude oil. These classes include polycyclic naphthenic, mono-, di-, and polynuclear aromatic, mono-and dibenzthiophenic, carbazolic, and phenolic types. This identification procedure affords the first semiquantitative assessment of carboxylic acid classes in a crude oil relative to all of the acids present.

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Section: Sulfur Compounds Benzdinaphthenesmentioning

confidence: 99%

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

Seifert¹,

Teeter²,

Howells³

et al. 1969

Anal. Chem.

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“…Previous work has shown that it is possible to produce benzene from acetylene on a variety of metal surfaces under both ultra-high vacuum (UHV) and reaction conditions. 9–35 For example, Tysoe et al showed acetylene forms benzene and ethylene on a Pd(111) surface and that increasing the surface acetylene coverage increased the yield of benzene. 36 In addition, the authors observed a threshold acetylene coverage of 0.3 ML, below which benzene formation does not occur.…”

Section: Introductionmentioning

confidence: 99%

100% selective cyclotrimerization of acetylene to benzene on Ag(111)

Çınar,

Zhang,

Happel

et al. 2024

Chem. Sci.

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“…Although carbon materials are usually considered as nonreactive supports for metal particles, increasing evidence suggests the inherent catalytic activity of carbon materials themselvesa phenomenon known as carbocatalysis. − As early as in 1866, Berthelot reported carbocatalytic pyrolysis of acetylene, which he applied to synthesize benzene in the presence of carbon . Later, in the 1920s, the synthesis of benzene by acetylene condensation on charcoal was carried out by Zelinsky. − From 1925–1930, activated charcoal was shown to mediate aerobic oxidation reactions. − In spite of the long history of carbocatalytic transformations, their mechanisms remained largely incomprehensible due to the extraordinary complexity of the catalytic processes involving fluxional (metastable) active centers at the carbon surface. − , …”

Section: Introductionmentioning

confidence: 99%

Carbocatalytic Acetylene Cyclotrimerization: A Key Role of Unpaired Electron Delocalization

2020

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Development of sustainable catalysts for synthetic transformations is one of the most challenging and demanding goals. The high prices of precious metals and the unavoidable leaching of toxic metal species leading to environmental contamination make the transition metal-free catalytic systems especially important. Here we demonstrate that carbene active centers localized on carbon atoms at the zigzag edge of graphene represent an alternative platform for efficient catalytic carbon− carbon bond formation in the synthesis of benzene. The studied acetylene trimerization reaction is an efficient atom-economic route to build an aromatic ringa step ubiquitously important in organic synthesis and industrial applications. Computational modeling of the reaction mechanism reveals a principal role of the reversible spin density oscillations that govern the overall catalytic cycle, facilitate the product formation, and regenerate the catalytically active centers. Dynamic π-electron interactions in 2D carbon systems open new opportunities in the field of carbocatalysis, unachievable by means of transition metal-catalyzed transformations. The theoretical findings are confirmed experimentally by generating key moieties of the carbon catalyst and performing the acetylene conversion to benzene.

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Über die Kontakt‐Kondensation des Acetylens

Cited by 15 publications

References 8 publications

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

100% selective cyclotrimerization of acetylene to benzene on Ag(111)

Carbocatalytic Acetylene Cyclotrimerization: A Key Role of Unpaired Electron Delocalization

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