Molecular-level characterization of crude oil compounds combining reversed-phase high-performance liquid chromatography with off-line high-resolution mass spectrometry

Sim, Arum; Cho, Yunju; Kim, Daae; Witt, Matthias; Birdwell, Justin E.; Kim, Byung Ju; Kim, Sunghwan

doi:10.1016/j.fuel.2014.10.019

Cited by 36 publications

(37 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The double‐bond equivalence (DBE) number is widely used in petroleum analysis to reflect the unsaturation degree of each chemical compound. The index of the molecule C c H h O o N n is defined as:

DBE = c + 1 - h / 2 + n / 2

…”

Section: Methodsmentioning

confidence: 50%

Analyzing the solid soot particulates formed in a fuel‐rich flame by solvent‐free matrix‐assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry

Zhang

Shao

Sarathy

2020

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale:The compositional and structural information of soot particles is essential for a better understanding of the chemistry and mechanism during the combustion. The aim of the present study was to develop a method to analyze such soot particulate samples with high complexity and poor solubility. Methods:The solvent-free sample preparation matrix-assisted laser desorption/ ionization (MALDI) technique was combined with the ultrahigh-resolution Fourier transform ion cyclotron resonance (FTICR) mass spectrometry (MS) for the characterization of solid soot particulates. Moreover, a modified iso-abundance plot (Carbon Number vs. Hydrogen Number vs. Abundance) was introduced to visualize the distributions of various chemical species, and to examine the agreement between the hydrogen-abstraction-carbon-addition (HACA) mechanism and the polycyclic aromatic hydrocarbon growth in the investigated flame system. Results:This solvent-free MALDI method enabled the effective ionization of the solid soot particulates without any dissolving procedure. With the accurate m/z ratios from FTICR-MS, a unique chemical formula was assigned to each of the recorded mass signals. The combustion products were proven to be mainly large polycyclic aromatic hydrocarbons (PAHs), together with a small amount (<5%) of oxidized hydrocarbons. Conclusions:The developed method provides a new approach for the molecular characterization of soot particulates like carbonaceous materials. The investigated soot particulates are mainly PAHs with no or very short aliphatic chains. The growth mechanism of PAHs during combustion can be examined against the classic HACA mechanism.

show abstract

DBE = c + 1 - h / 2 + n / 2

…”

Section: Methodsmentioning

confidence: 50%

Analyzing the solid soot particulates formed in a fuel‐rich flame by solvent‐free matrix‐assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry

Zhang

Shao

Sarathy

2020

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…In comparison, the separation achieved with reversed phase HPLC in previous studies depended on DBE and alkylation, whilst heteroatom content did not influence the elution order. 11 Extracted ion chromatograms of selected negative quasi-molecular ions are shown in Figure 5.…”

Section: Hplc-esci-tofmsmentioning

confidence: 99%

“…Literature indicates that reverse phase HPLC has been used for the analysis of diesel, 9 jet fuel 10 and crude-oil, 11 but group-type separations are most often achieved with normal phase liquid chromatography. 8,12 Standard methods, i.e.…”

Section: Introductionmentioning

confidence: 99%

Class Separation of the Trace Polar Species Present in Diesel Using Hydrophilic Interaction Chromatography and High Resolution Mass Spectrometry

2018

View full text Add to dashboard Cite

The analysis of fuels is not straightforward, due to its complex nature, and many different techniques have been developed to address this complexity. This paper reports on the use of hydrophilic interaction liquid chromatography (HILIC) as a complementary and green method for classifying diesel fuel composition. For comparative reasons, analyses with and without chromatographic pre-separation were performed. Selective ionization of polar species was achieved with electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI). High resolution time of flight mass spectrometry (TOFMS) was used to summarize the fuel composition in terms of compound classes based on accurate mass based elemental compositions. These compound classes showed different retention characteristics and were separated to a certain extent under hydrophilic interaction conditions. In normal phase liquid chromatography, the separation is based on heteroatom content, whereas alkylation (chain length) and degree of unsaturation (or double bond equivalents, DBE) play an important role in reversed phase liquid chromatography. The separation achieved with the proposed HILIC method depended on heteroatom content, DBE as well as hydrogen bonding, whilst alkylation did not influence retention significantly. This work therefore presents an alternative and complementary method for fuel analysis, compared to traditional reverse and normal phase liquid chromatography, by considering specific advantages and limitations.

show abstract

“…Ion mobility spectrometry‐mass spectrometry (IMS‐MS) is another important method to study chemical structures and it is reported to be a promising research to study proteins, metabolites, and aromatic compounds in crude oil . Gas‐phase separation achieved by IM can add another level of chromatography to the commonly used liquid phase separation . In addition, IM can be used to identify isomers.…”

Section: Comparison Between Experimental and Theoretical Ccs Values Omentioning

confidence: 99%

Comparison of Theoretical Calculation Methods for Obtaining Collisional Cross‐Section of Aromatic Compounds

Lim

Ahmed

Kim

2018

Bulletin Korean Chem Soc

Self Cite

View full text Add to dashboard Cite

Mass spectrometry (MS) has emerged as one of the most important tools for chemical and biochemical analysis. 1 MS is widely used for the analysis of proteins, drugs, metabolites, petroleum products, environmental chemicals, and foods. In such studies, MS is used to measure the molecular weight of the compounds, which helps in identifying the molecules. In particular, ultrahigh resolution MS has been used to obtain accurate molecular weight. MS can also be used to elucidate chemical structures. In those application, tandem MS 2 and hydrogen-deuterium exchange MS have been used. 3-5 Ion mobility spectrometry-mass spectrometry (IMS-MS) 6-8 is another important method to study chemical structures and it is reported to be a promising research to study proteins, 9,10 metabolites, 11,12 and aromatic compounds in crude oil. 13 Gas-phase separation achieved by IM can add another level of chromatography to the commonly used liquid phase separation. 14-17 In addition, IM can be used to identify isomers.Despite its potential, the application of IM-MS has been limited in the MS community. There are two critical limitations of IM-MS analysis: (1) the limited resolving power for gas-phase separation; (2) the need for combining theoretical calculations. The former can be overcome by the development of suitable instruments and data interpretation methods. In the case of second limitation, it has been widely accepted that combining theoretical collisional cross-section (CCS) calculation with experimental determination of CCS is necessary to fully utilize the IM-MS data.The theoretical CCS calculation includes two steps: in the first step, the structures are calculated and optimized, and in the second step, the CCS was calculated based on the optimized structure. For structural optimization, quantum chemical approaches, including the density functional theory (DFT) 18 have been widely used. However, quantum mechanical calculations are computationally expensive and not suitable for regular users of IM-MS. Therefore, it will be advantageous for the IM-MS community if a less computationally expensive and more easily accessible classical method would be as effective as the quantum mechanical approach. However, the effectiveness of lower-level CCS calculation has not been evaluated.In this study, the theoretical CCS values determined by various theoretical calculations were compared with the experimentally determined CCS values. The overall work flow for a comparative study of the CCS values obtained by computational chemistry and MS measurement is presented in a previous study. Briefly, the CCS values of molecules are experimentally determined by IM-MS and then compared with the theoretically calculated CCS values to find structures that can best explain the obtained IM-MS spectra.The experimental CCS values were obtained from a previous work. 19 The list of compounds is provided in the Table S1 (Supporting Information). Briefly, the drift time is converted into the CCS based on the previously reported CCS values of poly-DL-alanine. 19...

show abstract

Molecular-level characterization of crude oil compounds combining reversed-phase high-performance liquid chromatography with off-line high-resolution mass spectrometry

Cited by 36 publications

References 47 publications

Analyzing the solid soot particulates formed in a fuel‐rich flame by solvent‐free matrix‐assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry

Analyzing the solid soot particulates formed in a fuel‐rich flame by solvent‐free matrix‐assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry

Class Separation of the Trace Polar Species Present in Diesel Using Hydrophilic Interaction Chromatography and High Resolution Mass Spectrometry

Comparison of Theoretical Calculation Methods for Obtaining Collisional Cross‐Section of Aromatic Compounds

Contact Info

Product

Resources

About