A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of <i>S</i>-Alkylsulfonium Salts. 5. Denitrogenation Reactivity of Basic and Neutral Nitrogen Compounds

Shiraishi, Yasuhiro; Tachibana, Kenya; Hirai, Takayuki; Komasawa, Isao

doi:10.1021/ie0104565

Cited by 13 publications

(8 citation statements)

References 10 publications

(38 reference statements)

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“…Their possible core structures are indole, carbazole, acridine, and their derivatives (see Figure e). Literature studies show that indole, carbazole, and their derivatives are difficult to be removed by HDN for their basicity lower than basic nitrogen species, such as quinoline. − Although acridine belongs to basic nitrogen species, hydrodeoxygenation (HDO) of N 1 O 1 (DBE of 12) may contribute to its high content in hydrotreated shale oil.…”

Section: Resultsmentioning

confidence: 99%

Understanding Shale Oil Hydrotreatment with Composition Analysis Using Positive-Ion Mode Atmospheric Pressure Photoionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry

Zhang

Gao

et al. 2017

Energy Fuels

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Positive-ion mode of atmospheric pressure photoionization (APPI) coupled with a 9.4 T Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer has been applied to the characterization of shale oil from pyrolysis and its hydrotreatment. The hydrotreated shale oil was obtained through reactions over catalysts Ni−Mo, Ni−W, or Co−Mo. It was found that N 1 and N 1 O 1 species are the dominant N compounds and S 1 species is the dominant S compound in shale oil from pyrolyzing Huadian oil shale. The primary aromatic hydrocarbons (AHCs) are mono-and double-ring aromatics. After hydrotreatment, both S and N compounds are effectively removed and the catalyst Ni−Mo shows the best performance in hydrodesulfurization (HDS) and hydrodenitrogenation (HDN). The AHC species, especially the mono-ring aromatics, increases as a result of the transformation of N 1 , N 1 O 1 , and S 1 species into AHC species through hydrotreatment. Indole, carbazole, acridine, and their derivatives are preserved as N 1 species. The reactions of HDN for shale oil were further analyzed by considering the transformation between N 1 O 1 and N 1 species.

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Section: Resultsmentioning

confidence: 99%

Understanding Shale Oil Hydrotreatment with Composition Analysis Using Positive-Ion Mode Atmospheric Pressure Photoionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry

Zhang

Gao

et al. 2017

Energy Fuels

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“…Nitrogen compounds are then precipitated as N-methylated tetrafluoroborates. Denitrogenation of light oils and vacuum gas oil was successfully achieved by this method (Table ), and it was accompanied by alkylation of sulfur and aromatics. , Studies with model compounds revealed that aniline, pyridine, quinoline, and carbazole were removed as precipitates of their corresponding methylated products, while indole and pyrrole were removed as insoluble polymerized materials. In addition, denitrogenation of basic nitrogen compounds and compounds containing alkyl substituents was more effective than that of nonbasic nitrogen compounds.…”

Section: Chemical Conversion Followed By Separationmentioning

confidence: 99%

“…Alkylation as a reaction has been investigated for denitrogenation of light oils 131 and vacuum gas oil. 132 The nitrogen compounds are methylated and then removed by precipitation. The alkylating agents used were CH 3 I and AgBF 4 .…”

Section: Energy and Fuelsmentioning

confidence: 99%

Nitrogen Removal from Oil: A Review

2016

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The selective removal of nitrogen-containing compounds from oil and oil fractions is of interest because of the potential deleterious impact of such compounds on products and processes. Problems caused by nitrogen-containing compounds include gum formation, acid catalyst inhibition and deactivation, acid−base pair-related corrosion, and metal complexation. A brief overview of the classes of nitrogen compounds found in oil is provided. The review of processes to remove nitrogen from oil emphasizes studies that investigated denitrogenation of industrial feedstocks, such as refinery fractions, heavy oils, and bitumens. The main topics covered are hydrotreating, liquid−liquid phase partitioning, solvent deasphalting, adsorption, chemical conversion followed by separation, and microbial conversion. Chemical conversion processes include oxidative denitrogenation, N-alkylation, complexation with metal salts, and conversion in high-temperature water. There are many processes for denitrogenation by separation of the nitrogen-rich products from oil without removing the nitrogen group from the nitrogencontaining compounds. As a consequence, most of these processes are viable mainly for removal of nitrogen from low-nitrogencontent oils, typically with <0.1 wt % N. At present, hydrodenitrogenation appears to be the only industrially viable process for nitrogen removal from oils with high nitrogen content.

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“…Basic nitrogen compounds can be removed using an ion-exchange resin, ,− by liquid/liquid extraction using volatile carboxylic acid, and by metal complexation . The simultaneous removal of sulfur- and nitrogen-containing compounds has been studied by alkylation and subsequent precipitation method using excess alkylating agents (CH 3 I and AgBF 4 ), − and by combination of UV irradiation , or chemical oxidation with subsequent liquid−liquid extraction using an oil/acetonitrile two-phase system liquid/liquid extraction. One alternate approach to remove unwanted heterocyclic compounds is to use bacterial cells or enzymes as biocatalysts .…”

Section: Introductionmentioning

confidence: 99%

Novel Methodology toward Deep Desulfurization of Diesel Feed Based on the Selective Elimination of Nitrogen Compounds

Macaud

Sévignon

Favre‐Réguillon

et al. 2004

Ind. Eng. Chem. Res.

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π-Acceptor molecules covalently attached on hydrophilic support were used to selectively remove neutral nitrogen heterocyclic compounds from diesel feed by a charge transfer mechanism. Functionalized hydrophilic polymers can effectively adsorb nitrogen heterocyclic compounds with a high selectivity toward sulfur heterocyclic compounds from model and real feed. The results showed that charge transfer processes coupled with an ion-exchange process to selectively remove basic nitrogen compounds are efficient enough to produce denitrogenated feed in high yield. This study was conducted to determine whether trends in hydrodesulfurization (HDS) activity with lower sulfur content were mainly the result of lower reactivity of hindered sulfur compounds or due to nitrogen species inhibition. The inhibition effects of nitrogen compounds on HDS at conditions commonly used in the hydrotreatment of gas oil feedstocks has been experimentally determined. This study suggests that the selective removal of nitrogen compounds from gas oil strongly enhanced the deep desulfurization.

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A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 5. Denitrogenation Reactivity of Basic and Neutral Nitrogen Compounds

Cited by 13 publications

References 10 publications

Understanding Shale Oil Hydrotreatment with Composition Analysis Using Positive-Ion Mode Atmospheric Pressure Photoionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry

Understanding Shale Oil Hydrotreatment with Composition Analysis Using Positive-Ion Mode Atmospheric Pressure Photoionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry

Nitrogen Removal from Oil: A Review

Novel Methodology toward Deep Desulfurization of Diesel Feed Based on the Selective Elimination of Nitrogen Compounds

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