Fundamental Study on Desulfurization of Petroleum Using Synthesized Novel Ionicliquid and Betaines Moieties

Additional Funding Sources

The project described was supported by the 2019 Internal Seed Grant through ISU.

Abstract

With conventional light and middle crude oil production in decline, efforts have increasingly turned to heavy and extra heavy crude oils production. However, these oils contain a much greater proportion of sulfur- and nitrogen-containing heterocycles than lighter crude, which is resistant to current desulfurization and denitrogenation processes. These compounds not only contribute to emission of SOx and NOx pollutants upon combustion, but also create difficulties in crude oil production, transport, refinery and its conversion to useful petrochemicals.

This research will alleviate that problem by focusing on the ionic liquid extraction of five of the most prevalent heterocyclic compounds - thiophene, dibenzothiophene, alkyldibenzothiophenes, dibenzopyrrole (carbazole), and alkyldibenzopyrroles. By using a two-stage process that first separates the nitrogen-containing pyrroles from the sulfur heterocycles we hope to simplify the purification of individual components for later resale.

Our strategy is to use glycine-derived, tetraalkylammonium carboxylate betaines for the selective extraction of pyrroles taking advantage of the hydrogen bonding affinity of the pyrrole N-H to carboxylates. Subsequently, thiophenes will be extracted from the remaining crude using imidazolium ionic liquids. These ionic liquids will bear a tethered electron poor aromatic ring, which will act in tandem with the electron poor imidazolium core to π-stack with the electron rich thiophene core. The selectivity and extractive efficiency of each ionic liquid will be determined using a dodecane model system containing all five components and measuring the extraction content by spectroscopic means, primarily Nuclear Magnetic Resonance spectroscopy.

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Fundamental Study on Desulfurization of Petroleum Using Synthesized Novel Ionicliquid and Betaines Moieties

With conventional light and middle crude oil production in decline, efforts have increasingly turned to heavy and extra heavy crude oils production. However, these oils contain a much greater proportion of sulfur- and nitrogen-containing heterocycles than lighter crude, which is resistant to current desulfurization and denitrogenation processes. These compounds not only contribute to emission of SOx and NOx pollutants upon combustion, but also create difficulties in crude oil production, transport, refinery and its conversion to useful petrochemicals.

This research will alleviate that problem by focusing on the ionic liquid extraction of five of the most prevalent heterocyclic compounds - thiophene, dibenzothiophene, alkyldibenzothiophenes, dibenzopyrrole (carbazole), and alkyldibenzopyrroles. By using a two-stage process that first separates the nitrogen-containing pyrroles from the sulfur heterocycles we hope to simplify the purification of individual components for later resale.

Our strategy is to use glycine-derived, tetraalkylammonium carboxylate betaines for the selective extraction of pyrroles taking advantage of the hydrogen bonding affinity of the pyrrole N-H to carboxylates. Subsequently, thiophenes will be extracted from the remaining crude using imidazolium ionic liquids. These ionic liquids will bear a tethered electron poor aromatic ring, which will act in tandem with the electron poor imidazolium core to π-stack with the electron rich thiophene core. The selectivity and extractive efficiency of each ionic liquid will be determined using a dodecane model system containing all five components and measuring the extraction content by spectroscopic means, primarily Nuclear Magnetic Resonance spectroscopy.