Chromatographic isolation of vanadyl porphyrins from heavy oil resins

Mironov, N. A.; Sinyashin, Kirill; Abilova, G. R.; Tazeeva, E. G.; Milordov, D. V.; Yakubova, S. G.; Borisov, D. N.; Gryaznov, P. I.; Borisova, Yu. Yu.; Yakubov, M. R.

doi:10.1007/s11172-017-1907-4

Cited by 14 publications

(13 citation statements)

References 17 publications

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“…However, this multistep chromatographic method suffers from high time and eluent consumption. In our recent works, , we proposed a more simple approach based on application of sulfocationites as adsorbents for isolation of spectrally pure VPs from primary concentrates derived in one stage on a SiO 2 column from heavy oil resins and DMF extracts of asphaltenes. Our approach is a further development of the method of Barwise and Whitehead, who discovered that silica gel modified with propylsulfonic acid can be successfully employed for separation of VPs from polar petroleum components bearing basic nitrogen.…”

Section: Introductionmentioning

confidence: 99%

“…Our approach is a further development of the method of Barwise and Whitehead, who discovered that silica gel modified with propylsulfonic acid can be successfully employed for separation of VPs from polar petroleum components bearing basic nitrogen. Our study of the elution behavior of VPs and nonporphyrin impurities in a sulfocationite column revealed optimal chromatographic conditions providing maximization of the yield and spectral purity of recovered VPs. , Also, we adapted this method for much less expensive sulfocationites such as cation exchange resin QU-2-8 , (domestic analog of Amberlite IR120) and asphaltenic sulfocationite created and patented by our group. This makes the sulfocationite-based method more suitable for preparative-scale purification of petroporphyrins.…”

Section: Introductionmentioning

confidence: 99%

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Comparative Study of Resins and Asphaltenes of Heavy Oils as Sources for Obtaining Pure Vanadyl Porphyrins by the Sulfocationite-Based Chromatographic Method

et al. 2018

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The resins and asphaltenes of three heavy oils differing in origin (Permian and Carboniferous) and vanadium content (0.025–0.165 wt %) have been studied as sources for isolation of spectrally pure vanadyl porphyrins by sulfocationite-based chromatographic method developed by us recently. This method consists of removing the low polar nonporphyrin components from the resins or DMF extract of asphaltenes on SiO2-column followed by chromatographic isolation of vanadyl porphyrins on the sulfocationite. The asphaltenes were revealed to be a more promising source of vanadyl porphyrins because they possess ≥5 times higher content of vanadium, provide better accumulation of vanadyl porphyrins during deposition extraction by N,N-dimethylformamide, and are less contaminated by low polar nonporphyrin compounds capable of coeluting with vanadyl porphyrins through the sulfocationite column. According to matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy, DPEP vanadyl porphyrins were found to be the most abundant type for all studied samples (34.1–54.5%). Rhodo vanadyl porphyrins belong to minor components (3.3–8.7% for each subtype) while Etio and Di-DPEP types take the intermediate position (9.8–28.7%). The resins and asphaltenes of the same oil showed significant difference in the group composition of purified vanadyl porphyrins. For the resins, a ∼1.3-fold decreased content of DPEP vanadyl porphyrins was found, which was compensated by a ∼1.5- and/or ∼1.8-fold increase in the content of Etio and Rhodo vanadyl porphyrins, respectively. However, this change in the composition of vanadyl porphyrins is not accompanied by a notable change of their average molecular weight despite the fact that increased concentration of more substituted (i.e., more hydrophobic) vanadyl porphyrins could be expected for less polar resins. This fact was interpreted in favor of association of vanadyl porphyrins with nonporphyrin components of the oil.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comparative Study of Resins and Asphaltenes of Heavy Oils as Sources for Obtaining Pure Vanadyl Porphyrins by the Sulfocationite-Based Chromatographic Method

et al. 2018

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“…Moreover, a different porphyrin ligand structure demonstrates varied retention time, which subsequently increases the analysis complexity. Furthermore, some metallic porphyrins tend to be adsorbed on the stationary phase and consequently poison the column used [45].…”

Section: ■ Detection and Quantification Of Metallic Porphyrins In Crude Oilsmentioning

confidence: 99%

The Origin, Physicochemical Properties, and Removal Technology of Metallic Porphyrins from Crude Oils

et al. 2021

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Crude oil is an indispensable energy feedstock for daily activities, although some amounts of metallic porphyrins components with undesired characteristics have been identified. These constituents are assumed to originate from the geochemical process of chlorophyll and heme derivatives. In addition, their chemical structures have been thoroughly characterized using spectroscopy techniques, while several analytical methods were adopted in the detection and concentration quantification in the crude oils. The metallic porphyrins have several demerits, including the deactivation of used catalysts, contamination of the treated petrochemical products, and corrosion of the industrial equipment. Also, the removal process is considered challenging due to the strong interaction with the asphaltene fraction of crude oil. This review article, therefore, provides brief information on the origin, physicochemical properties, and possible removal technology of metallic porphyrins from crude oil samples. Besides, a better understanding of chemistry contributes a useful insight towards the development and establishment of better futuristic processing technology.

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“…Various analytical techniques have been developed for the characterization of metalloporphyrins, including ultraviolet–visible spectroscopy, − X-ray absorption methods, , atomic force microscopy, high-performance liquid chromatography, − gas chromatography, − and mass spectrometry (MS) with different ion source and mass analyzer. ,− Among them, high-resolution MS, such as Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS), can provide elemental composition information on detected ions and had become a common technique for metalloporphyrin molecular composition analysis. Because of the low concentration of metalloporphyrins, it is always necessary to separate and concentrate metalloporphyrins from petroleum matrices before MS analysis.…”

Section: Introductionmentioning

confidence: 99%

Direct Nickel Petroporphyrin Analysis through Electrochemical Oxidation in Electrospray Ionization Ultrahigh-Resolution Mass Spectrometry

et al. 2021

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The compositional analysis of heavy petroleum nickel porphyrins by electrospray ionization (ESI) is challenged by their trace amount and relatively low response. In the presented study, we developed a method to enhance the response of nickel porphyrins in ESI by introducing the electrochemical oxidation reaction. The effect of ESI type, solvent, and additives were investigated for standard compounds and heavy oils. The results showed that the ESI source with high positive needle voltage is suitable for nickel porphyrins analysis using dichloromethane as the solvent and trifluoroacetic acid as the ionization promoter. Under the optimized conditions, nickel and vanadyl porphyrins can be directly ionized as molecular radical cations ([M]+•) via electrochemical oxidation due to their low oxidation potential and gas-phase ionization energy. The method is capable of direct analysis of both nickel and vanadyl porphyrins in a vacuum residue without any prior preparation. We also observed the molecular radical cations of other compounds with high aromaticity and short side chains (such as hydrocarbons, nitrogen- and sulfur-containing species), which indicate that the electrochemical oxidation reaction can be used for nonpolar compounds ESI analysis.

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Chromatographic isolation of vanadyl porphyrins from heavy oil resins

Cited by 14 publications

References 17 publications

Comparative Study of Resins and Asphaltenes of Heavy Oils as Sources for Obtaining Pure Vanadyl Porphyrins by the Sulfocationite-Based Chromatographic Method

Comparative Study of Resins and Asphaltenes of Heavy Oils as Sources for Obtaining Pure Vanadyl Porphyrins by the Sulfocationite-Based Chromatographic Method

The Origin, Physicochemical Properties, and Removal Technology of Metallic Porphyrins from Crude Oils

Direct Nickel Petroporphyrin Analysis through Electrochemical Oxidation in Electrospray Ionization Ultrahigh-Resolution Mass Spectrometry

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