Terpenoid‐Derived Sulfides as Ultimate Organic Sulfur Compounds in Extensively Desulfurized Fuels

Charrié-Duhaut, Armelle; Schaeffer, Christine; Adam, Pierre; Manuelli, Pascal; Scherrer, Pierre; Albrecht, Pierre

doi:10.1002/anie.200351426

Cited by 18 publications

(28 citation statements)

References 21 publications

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“…The thiapolycyclanes were derivates of thiophane condensed mainly with 5-membered rings. A series of novel, terpenoidderived polycyclic sulfides were identified by Charrié-Duhaut et al (2003) in highly desulfurized diesel oils and identified as 1,1,4a,6-tetramethyl-9-alkyl-1,2,3,4,4a,9b-hexahydrodibenzothiophenes.…”

Section: Sulfur Compounds In Crude Oil and Petroleum Productsmentioning

confidence: 99%

Characterization of polycyclic aromatic sulfur heterocycles for source identification

Hegazi

Andersson

2007

Oil Spill Environmental Forensics

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Section: Sulfur Compounds In Crude Oil and Petroleum Productsmentioning

confidence: 99%

Characterization of polycyclic aromatic sulfur heterocycles for source identification

Hegazi

Andersson

2007

Oil Spill Environmental Forensics

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“…Refractory sulfur compounds are mainly DBTs with shielding structures, such as 4-DBT and 4,6-DBT, which are usually the dominant sulfur compounds in hydrogenated diesel and recognized as the most resistant sulfur compounds for hydroprocessing . In recent years, some sulfides have been found in crude oil with a stronger steric hindrance effect and are more difficult to hydrodesulfurize than 4,6-DBT . These compounds have characteristic biomarker skeletons and are considered to be the products of isoprenoids via sulfurization in early diagenesis. ,− The content of these compounds may vary greatly in crude oil.…”

Section: Conversion and Transformation Of Sulfur Compounds In Petrole...mentioning

confidence: 99%

“…In recent years, some sulfides have been found in crude oil with a stronger steric hindrance effect and are more difficult to hydrodesulfurize than 4,6-DBT . These compounds have characteristic biomarker skeletons and are considered to be the products of isoprenoids via sulfurization in early diagenesis. ,− The content of these compounds may vary greatly in crude oil. Therefore, it will be difficult to achieve ultradeep desulfurization if the feedstock contains a large proportion of straight-run diesel oil, which is traditionally considered to be a high-quality blending material for diesel production.…”

Section: Conversion and Transformation Of Sulfur Compounds In Petrole...mentioning

confidence: 99%

“…153 In recent years, some sulfides have been found in crude oil with a stronger steric hindrance effect and are more difficult to hydrodesulfurize than 4,6-DBT. 154 These compounds have characteristic biomarker skeletons and are considered to be the products of isoprenoids via sulfurization in early diagenesis. 77,154−156 The content of these compounds may vary greatly in crude oil.…”

Section: Conversion and Transformation Of Sulfur Compounds In Petrole...mentioning

confidence: 99%

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Review on Sulfur Compounds in Petroleum and Its Products: State-of-the-Art and Perspectives

Shi

2021

Energy Fuels

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Sulfur compounds have significant geochemical information, and the removal of sulfur from petroleum products is one of the most important tasks in petroleum refining. However, it is a challenging task to reveal the chemical composition of sulfide at the molecular level because of its complex composition. Unremitting efforts have been made to develop methods for the separation and characterization of sulfur compounds in petroleum and its products in order to understand the mechanisms of their geological origin and their transformation in petroleum processing. Sulfur compounds include thiophenes, sulfides, thiols, sulfoxides, and sulfones, etc. The sulfur element is mainly from sulfate in the sedimentary environment, but the combination of sulfur into hydrocarbons could occur in different ways. Most sulfur compounds are generated in the early diagenetic period through the reaction of unsaturated organic matter with H2S or elemental sulfur released from sulfate via bacterial sulfate reduction. The composition of the sulfur compound in petroleum could be largely altered by thermal maturation, leading to an increase in the relative abundance of highly condensed aromatic sulfur compounds. Another important pathway of sulfur addition is thermochemical reactions between sulfate and hydrocarbons at high temperatures. Some sulfur compounds have a relatively weak chemical stability and are easily decomposed into small-molecule sulfur compounds in petroleum processing. Removing sulfur from petroleum is an essential task for petroleum refinement and upgrading, in which the steric hindrance effect is the most important factor affecting the desulfurization activity of sulfur compounds via hydrotreating. Some polar sulfur compounds are difficult to hydrogenate to remove sulfur; however, the chemical structures of these compounds are unclear. High-resolution mass spectrometry has revealed the high complexity of the molecular composition of sulfur compounds in heavy oils and their polar fractions. However, understanding of their molecular structure is limited, and further research should focus on the formation and transformation mechanism of these polar sulfur compounds. This review will focus on the molecular composition of petroleum sulfur compounds with a collection of topics of sulfur compounds that covers the upstream and downstream petroleum industry, including separation and characterization methods, molecular and structural composition of various sulfur compounds, mechanisms of their geological origin, and their transformation during petroleum processing.

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“…Compounds with hexahydrodibenzothiophene (C 12 H 14 S) structures were reported in analyzed samples after a hydro-desulfurization process. 36 Hexahydrodibenzothiophenes (C 12 H 14 S) also have a DBE value of 6. If hexahydrodibenzothiophenes (C 12 H 14 S) were abundant, we would expect to see the product ions of dihydrobenzothiophene (C 8 H 8 S) as the saturated cyclic ring could be lost via molecular collision (refer to Figure 4).…”

Section: Energy and Fuelsmentioning

confidence: 99%

Interpreting Chemical Structures of Compounds in Crude Oil Based on the Tandem Mass Spectra of Standard Compounds Obtained at the Same Normalized Collision Energy

Cho

Kim

2017

Energy Fuels

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In this study, the tandem mass spectra of 25 standard compounds, obtained at a normalized collision energy of 50, were used to investigate the structures of crude oil. The product ion distributions of these standard compounds were dependent on the number and length of their alkyl side chains. Long alkyl side chains (C n H2n , n ≥ 5) were easily lost during molecular collision, leaving behind methyl groups on the aromatic cores. In contrast, compounds with short interlinking alkyl chains (C n H2n , n ≤ 1) were not significantly fragmented, and a decrease in the double bond equivalent (DBE) value was observed when compounds had saturated rings. Based on the derived observations, the possible structures of S1-class compounds with DBE values of 6, 7, 8, and 9 were suggested. It was also determined that, in the tandem mass spectra of crude oil fractions, (1) a series of peaks separated by CH2 groups were generated from isomers with different numbers of alky side chains, (2) the number of methyl groups left after molecular collision was positively correlated to the quantity of branched molecules, and (3) significant fragmentation did not occur for aromatic cores linked by short alkyl chains (C n H2n , n ≥ 2), and hence, archipelago structures with short alkyl linkage could not be excluded based solely on tandem mass spectra. This study clearly shows that a systematic analytical approach using a well-defined set of standard compounds combined with tandem mass spectrometry can significantly improve our understanding on the chemical structures of crude oil compounds.

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Terpenoid‐Derived Sulfides as Ultimate Organic Sulfur Compounds in Extensively Desulfurized Fuels

Cited by 18 publications

References 21 publications

Characterization of polycyclic aromatic sulfur heterocycles for source identification

Characterization of polycyclic aromatic sulfur heterocycles for source identification

Review on Sulfur Compounds in Petroleum and Its Products: State-of-the-Art and Perspectives

Interpreting Chemical Structures of Compounds in Crude Oil Based on the Tandem Mass Spectra of Standard Compounds Obtained at the Same Normalized Collision Energy

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