Fundamental synthetic fuel stability study. Final report, May 1, 1979-June 30, 1981

Frankenfeld, John W.; Taylor, William F.

doi:10.2172/5371539

Cited by 4 publications

(17 citation statements)

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“…GC–MS followed by FCAST analysis of the BNC fraction determined that it was composed of various substituted alkylbenzamines, pyridines, and quinolines. Based on previous studies, the presence of alkylbenzamines in these fuels may be responsible for promoting the observed sediment formation in storage …”

Section: Resultsmentioning

confidence: 92%

“…Analysis of the GC–MS data from this BNC fraction revealed that it was composed mainly of benzamines, quinolines, and possibly pyridines. Pyridines are known to be relatively innocuous with respect to fuel stability; however, pyrroles, particularly when containing electron-releasing groups adjacent to the nitrogen, are particularly reactive and have the potential to degrade fuel stability. , …”

Section: Resultsmentioning

confidence: 99%

“…Pyridines are known to be relatively innocuous with respect to fuel stability; however, pyrroles, particularly when containing electron-releasing groups adjacent to the nitrogen, are particularly reactive and have the potential to degrade fuel stability. 8,9 The GC−MS TIC and the NPD chromatograms for the NBNC fraction obtained by the dichloromethane (DCM) extraction from the silica gel can be seen in Figure 6. The NPD shows that this fraction consists of the heavier nitrogen compounds (between 40 and 60 min of retention time), which was previously noted to be the region containing the majority of the nitrogen-containing compounds in the fuel.…”

Section: Energy and Fuelsmentioning

confidence: 99%

“…This deleterious impact will be determined by the structure of the compounds, with some being fairly innocuous while others are reactive. Acid- or base-catalyzed condensation reactions have been identified as a major pathway by which these heteroatomic compounds can form large insoluble reaction products. , As such, nitrogen compounds are generally classified as either nonbasic (NBNC) or basic (BNC), which are separated according to the nitrogen acid/base quality as defined by the relative availability of electrons on the nitrogen atom. − In the context of this work, the term “basic nitrogen” refers to the organonitrogen compounds that can be isolated by mild acid extraction. BNCs found in fuels generally consist of alkyl pyrroles, alkyl pyridines, benzoquinolines, benzamines, and quinolines, while NBNCs tend to be compounds such as indoles and carbazoles.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of Organic Nitrogen Compounds and Their Impact on the Stability of Marginally Stable Diesel Fuels

et al. 2019

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A set of low-sulfur diesel fuels from the Western Pacific region were found to be unstable during storage although they passed all standard specification tests. This sample set was found to have high nitrogen content. Initially, liquid–liquid extractions with a mild aqueous acid were performed to separate basic and nonbasic nitrogen groups in an attempt to determine if these organonitrogen classes were responsible for the poor stability. The findings of this study indicate that there may be a correlation between the acid-extractable nitrogen compounds in these fuels and the formation of high levels of particulates in storage. To develop a more comprehensive understanding of the classes and distributions of organonitrogen compounds in fuels, a novel analytical method was developed using two-dimensional gas chromatography with nitrogen chemiluminescence detection (GCxGC-NCD). The GCxGC-NCD analyses revealed the presence of three distinct groups of nitrogen compounds. One group corresponded to the acid-extractable basic nitrogen compounds, one with the nonbasic nitrogen compounds, and a third early-eluting lighter polar organonitrogen fraction that had previously not been observed. This light organonitrogen fraction was unique to these particularly unstable fuels. If this is found to be universally applicable, this light polar nitrogen fraction may serve as an indicator of potentially unstable diesel fuels. Overall, the GCxGC-NCD method has been shown to be a valuable tool to enhance our understanding of the chemistry of organonitrogen species and their impact on fuel stability.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Energy and Fuelsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Characterization of Organic Nitrogen Compounds and Their Impact on the Stability of Marginally Stable Diesel Fuels

et al. 2019

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“…Unsaturated, heterocyclic NCCs (e.g., pyrroles) with alkyl group(s) attached to the carbon adjacent to the nitrogen atom were shown to be especially reactive. [14][15][16]20 Alkylamines known to be inert were found to interact with isoquinoline to produce sediment in the presence of 2,5-dimethylpyrrole. 19 Beal et al 21 showed that the reactivities of NCCs are greatly influenced by the compounds present in the mixture.…”

Section: Introductionmentioning

confidence: 99%

Examination of Two-Dimensional Gas Chromatography with a Nitrogen Chemiluminescence Detector to Facilitate Quantitation and Characterization of Nitrogen-Containing Compounds in Petroleum-Derived Fuels

et al. 2021

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A semiqualitative and quantitative method was developed to classify and quantify nitrogen-containing compounds (NCCs) in aviation and diesel fuels and marine gas oils by using two-dimensional gas chromatography with a nitrogen chemiluminescence detector (GCxGC NCD) without the need for lengthy extractions. Homoscedasticity was evaluated for different forms of linear regression. The weighted (1/x) trend line was more accurate than the nonweighted and weighted (1/x2) trend lines when quantitating six mixtures composed of several NCCs ranging from 50 ppb to 50 ppm. The lower limits of detection and quantitation of nitrogen were 6 and 20 ppb, respectively, by using the weighted (1/x) trend line. Relative response factors (RRF) of nitrogen were measured for several compounds, which showed that several aromatic (aniline, quinoline, benzothiazole, o-anisidine, and carbazole) and nonaromatic (N,N-dimethyldecylamine and N,N-dimethyldodecylamine) compounds have similar responses. Conversely, pyridine and pyrrole have smaller RRF. Further, alkylated pyridine and pyrrole were shown to have greater RRF than pyridine and pyrrole. Hence, equimolar responses for different NCCs were not observed in this study. Small RRF were likely not the result of thermally-induced degradation of analytes upon entry into the GC inlet. The elution times of known compounds were repeatable, which enabled the production of a template composed of chromatographic bins that facilitated characterization and quantitation of unknown NCCs in fuel samples. The template advances the classification of unknown NCCs in fuels compared to simplified classifications as basic, nonbasic, and neutral. Clear differences were observed in the chemical composition and concentrations of NCCs when the disparate fuel types were compared and between the same type of fuels (i.e., aviation fuels). Interday quality control measurements demonstrated high repeatability. Overall, the GCxGC NCD method was shown to be robust, repeatable, facilitated high throughput chemical analysis without the need for extractions, and provided detailed compositional and quantifiable data. This information may aid in linking correlations between NCCs and fuel properties such as stability.

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Storage stability of synfuels from oil shale. 3. Studies with actual shale-derived middle distillates

Frankenfeld¹,

Taylor²,

Brinkman³

1983

Ind. Eng. Chem. Prod. Res. Dev.

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The storage stability of various middle distillate fuels derived from oil shale was investigated by means of an accelerated storage stability test. A variety of liquids were studied including crude shale oils boiling in the middle distillate range, partially upgraded shale oils, and severely refined fuels. Large amounts of sediment were obtained from liquids with high heteroatom content. However, no direct correlation between nitrogen, sulfur, no oxygen levels and sediment level was observed. The results of these studies are consistent with those from previous work with model fuel systems. The sediments produced by different liquids differed in heteroatom content and other characteristics. The nitrogen level of the original liquid was only one factor determining the amounts and types of sediments produced. Thus, studies with model compounds and with actual shale-derived liquids indicate that the total nitrogen content of a fuel per se is not a general predictor of fuel storage stability.

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Fundamental synthetic fuel stability study. Final report, May 1, 1979-June 30, 1981

Cited by 4 publications

References 0 publications

Characterization of Organic Nitrogen Compounds and Their Impact on the Stability of Marginally Stable Diesel Fuels

Characterization of Organic Nitrogen Compounds and Their Impact on the Stability of Marginally Stable Diesel Fuels

Examination of Two-Dimensional Gas Chromatography with a Nitrogen Chemiluminescence Detector to Facilitate Quantitation and Characterization of Nitrogen-Containing Compounds in Petroleum-Derived Fuels

Storage stability of synfuels from oil shale. 3. Studies with actual shale-derived middle distillates

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