Organosulfur oxidation process
View Patent ↗This invention is a method of purifying fuel streams containing organonitrogen and organosulfur impurities. The fuel stream is first treated to extract organonitrogen impurities so that the nitrogen content of the fuel stream is reduced by at least 50 percent. After separation and recovery of the nitrogen-depleted fuel stream, the organosulfur impurities in the fuel stream are then oxidized with an organic hydroperoxide in the presence of a titanium-containing silicon oxide catalyst. The resulting sulfones may be more readily removed from the fuel stream than the non-oxidized organosulfur impurities.
1. A process comprising:
(a) extracting organonitrogen impurities from a fuel stream containing organonitrogen and organosulfur impurities whereby the nitrogen content of fuel stream is reduced by at least 50 percent to produce a fuel stream having a reduced amount of organonitrogen impurities;
(b) separating and recovering the fuel stream having a reduced amount of organonitrogen impurities; and
(c) contacting the separated fuel stream having a reduced amount of organonitrogen impurities with an organic hydroperoxide in the presence of a titanium-containing silicon oxide catalyst wherein a substantial portion of the organosulfur impurities are converted into sulfones.
2. The process of claim 1 wherein the organonitrogen impurities are extracted by solid-liquid extraction using at least one adsorbent.
3. The process of claim 2 wherein the adsorbent is selected from the group consisting of aluminum oxide, silicon oxide, silica-alumina, Y zeolite, Zeolite X, ZSM-5, and sulfonic acid resin.
4. The process of claim 3 wherein the adsorbent is selected from the group consisting of aluminum oxide, silica-alumina, and Y zeolite.
5. The process of claim 1 wherein the organonitrogen impurities are extracted by liquid-liquid extraction using at least one polar solvent.
6. The process of claim 5 wherein the polar solvent is selected from the group consisting of alcohol, ketone, water, and mixtures thereof.
7. The process of claim 6 wherein the ketone is a C 3 -C 8 aliphatic ketone.
8. The process of claim 7 wherein the ketone is acetone.
9. The process of claim 6 wherein the alcohol is a C 1 -C 4 alcohol.
10. The process of claim 9 wherein the alcohol is methanol.
11. The process of claim 5 wherein the polar solvent is a mixture of methanol and water.
12. The process of claim 1 wherein the organic hydroperoxide is t-butyl hydroperoxide.
13. The process of claim 1 wherein the titanium-containing silicon oxide catalyst is titania-on-silica.
14. The process of claim 1 comprising an additional step after step (c) of removing the sulfones from the fuel stream by solid-liquid or liquid-liquid extraction.
15. A process comprising:
(a) extracting organonitrogen impurities from a diesel fuel stream containing organonitrogen and organosulfur impurities whereby the nitrogen content of fuel stream is reduced by at least 50 percent to produce a fuel stream having a reduced amount of organonitrogen impurities;
(b) separating and recovering the diesel fuel stream having a reduced amount of organonitrogen impurities; and
(c) contacting the separated diesel fuel stream having a reduced amount of organonitrogen impurities with t-butyl hydroperoxide in the presence of a titania-on-silica catalyst wherein a substantial portion of the organosulfur impurities are converted into sulfones.
16. The process of claim 15 wherein the organonitrogen impurities are extracted by solid-liquid extraction using at least one adsorbent selected from the group consisting of aluminum oxide, silica-alumina and Y zeolite.
17. The process of claim 15 wherein the organonitrogen impurities are extracted by liquid-liquid extraction using at least one polar solvent selected from the group consisting of C 1 -C 4 alcohol, C 3 -C 8 aliphatic ketone, water, and mixtures thereof.
18. The process of claim 17 wherein the ketone is acetone.
19. The process of claim 17 wherein the alcohol is methanol.
20. The process of claim 17 wherein the polar solvent is a mixture of methanol and water.
21. The process of claim 15 comprising an additional step after step (c) of removing the sulfones from the diesel fuel stream by solid-liquid or liquid-liquid extraction.