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US 10,947,461 B2Granted
Selective liquid-liquid extraction of oxidative desulfurization reaction products
AssigneeSaudi Arabian Oil Company
InventorsEmad Naji Al-Shafei, Esam Zaki Hamad
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Abstract
The present invention provides selective extraction of sulfoxides, or sulfoxides in combination with sulfones, from hydrocarbon mixtures containing these compounds. A significant advantage of the invention is that oxidation products resulting from oxidative desulfurization of hydrocarbon feedstocks are selectively extracted with minimum co-extraction of non-oxidized products such as valuable hydrocarbon fuel components.
Claims11
An oxidative desulfurization process comprising:
- reactively sulfoxidating a hydrocarbon fraction containing organosulfur compounds to produce a hydrocarbon mixture containing product components, and by-product sulfoxides or a combination of sulfoxides and sulfones;
- contacting the mixture with a selective solvent formulation at a temperature in the range of about 0° C. to about 40° C.;
- and
- recovering a hydrocarbon product of reduced sulfur content,
- wherein the selective solvent formulation is determined by
- qualitatively analyzing the hydrocarbon mixture to determine the composition including the type of sulfoxidation reaction products, the type of aromatic hydrocarbons and the type of non-aromatic hydrocarbons;
- selecting as target sulfoxidation reaction products one or more sulfoxides or a combination of one or more sulfoxides and one or more sulfones;
- determining the activity coefficient γ of a range of extraction solvent compositions for the target sulfoxidation reaction products and at least one type of aromatic or non-aromatic hydrocarbon in the hydrocarbon fraction, the extraction solvent compositions within the range of extraction solvent compositions comprising an aqueous solution having a concentration of about 2.5 weight % to about 70 weight % by weight polar organic solvent in water, the polar organic solvent selected from the group consisting of acetic acid, formic acid and combinations comprising acetic acid or formic acid;
- and
- selecting, as the selective solvent formulation, an extraction solvent composition having an activity coefficient of less than about 16.5 for the target sulfoxidation reaction products that maximizes extraction of the target sulfoxidation reaction product, and an activity coefficient equal to or greater than about 16.5 for the at least one type of aromatic or non-aromatic hydrocarbon that minimizes co-extraction of the at least one type of aromatic or non-aromatic hydrocarbon.
7 more elements
An oxidative desulfurization process comprising:
- reactively sulfoxidating a hydrocarbon fraction containing organosulfur compounds to produce a hydrocarbon mixture containing product components, and by-product sulfoxides or a combination of sulfoxides and sulfones;
- contacting the mixture with a selective solvent formulation at a temperature in the range of about 0° C. to about 40° C.;
- and
- recovering a hydrocarbon product of reduced sulfur content,
- wherein the selective solvent formulation is an aqueous solution determined by selecting as target sulfoxidation reaction products one or more sulfoxides or a combination of one or more sulfoxides and one or more sulfones, and wherein the aqueous solution is selected from the group consisting of
- about 2.5 weight % to about 20 weight % of acetic acid and wherein the target compounds for extraction are non-bulky sulfoxide products,
- about 20 weight % to about 40 weight % of acetic acid and wherein the target compounds for extraction are bulky sulfoxide products,
- about 5 weight % to about 20 weight % of formic acid, and wherein the target compounds for extraction are non-bulky sulfoxide products,
- about 5 weight % to about 30 weight % of acetonitrile and about 5 weight % to about 30 weight % of formic acid and wherein the target compounds for extraction are a combination of 1 or more sulfoxides and 1 or more sulfones,
- about 5 weight % to about 30 weight % of acetic acid and about 5 weight % to about 30 weight % of acetone and wherein the target compounds for extraction are a combination of 1 or more sulfoxides and 1 or more sulfones,
- about 20 weight % to about 40 weight % of formic acid and wherein the target compounds for extraction include 4,6-dimethyldibenzothiophene oxide,
- about 10 weight % to about 30 weight % of acetic acid and wherein the target compounds for extraction include thiophene sulfide and thiophene sulfone, and
- about 30 weight % to about 40 weight % of formic acid and wherein the target compounds for extraction include thiophene sulfide and thiophene sulfone.
10 more elements
Dependencies are inferred from the claim text.