Desulfurization process

• US 7,144,499 B2
• Filed: 11/26/2003
• Issued: 12/05/2006
• Est. Priority Date: 11/26/2003
• Status: Expired due to Fees

• Current Assignee: Lyondell Chemical Technology LP (Lyondellbasell Industries NV)
• Original Assignee: Lyondell Chemical Technology LP (Lyondellbasell Industries NV)
• Inventors: Leyshon, David W., Han, Yuan-Zhang
• Primary Examiner(s): Nguyen, Tam M.
• Application Number:
  US10/723,870
• Publication Number:
  US 20050109677A1
• Time in Patent Office: 1,105 Days
• Field of Search: 208/208.R, 208/240, 208/196
• US Class Current: 208/208.00R
• CPC Class Codes: C10G 27/12 with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates plumbites or plumbates C10G19/06
• CPC Class Codes: C10G 53/14 including at least one oxidation step

Abstract

This invention is a method of purifying fuel streams containing organosulfur impurities. The fuel stream is oxidized with an organic hydroperoxide in the presence of an oxidation catalyst to form a sulfone product. The alcohol product of the organic hydroperoxide is then removed from the oxidized fuel stream, followed by extraction of the sulfone product by solid-liquid extraction using solid adsorbents. The alcohol removal step is found to improve the adsorption capacity of the solid adsorbents.

Claims

1. A process comprising:

(a) contacting a fuel stream containing organosulfur impurities with an organic hydroperoxide in the presence of an oxidation catalyst to form an oxidized fuel stream, wherein a substantial portion of the organosulfur impurities are converted into sulfones and a substantial portion of the organic hydroperoxide is converted into an alcohol;

(b) removing the alcohol from the oxidized fuel stream to form an alcohol-reduced oxidized fuel stream; and

(c) extracting the sulfones from the alcohol-reduced oxidized fuel stream by solid-liquid extraction using a sulfone adsorbent.

2. The process of claim 1 wherein the organic hydroperoxide is t-butyl hydroperoxide and the alcohol is t-butyl alcohol.

3. The process of claim 1 wherein the oxidation catalyst is a titanium-containing silicon oxide catalyst.

4. The process of claim 3 wherein the titanium-containing silicon oxide catalyst is titania-on-silica.

5. The process of claim 1 wherein the alcohol is removed by distillation.

6. The process of claim 1 wherein the sulfone adsorbent is selected from the group consisting of silicas, aluminas, and silica-aluminas.

16. The process of claim 1 wherein the sulfone adsorbent is selected from the group consisting of silicas, aluminas, and silica-aluminas.

7. 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;

(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 to form an oxidized fuel stream, wherein a substantial portion of the organosulfur impurities are converted into sulfones and a substantial portion of the organic hydroperoxide is converted into an alcohol;

(d) removing the alcohol from the oxidized fuel stream to form an alcohol-reduced oxidized fuel stream; and

(e) extracting the sulfones from the alcohol-reduced oxidized fuel stream by solid-liquid extraction using a sulfone adsorbent.

8. The process of claim 7 wherein the organonitrogen impurities are extracted by solid-liquid extraction using at least one organonitrogen adsorbent.

9. The process of claim 8 wherein the organonitrogen adsorbent is selected from the group consisting of aluminum oxide, silicon oxide, silica-alumina, zeolite Y, Zeolite X, ZSM-5, magnesium oxide, and sulfonic acid resin.

10. The process of claim 7 wherein the organonitrogen impurities are extracted by liquid-liquid extraction using at least one polar solvent.

11. The process of claim 10 wherein the polar solvent is selected from the group consisting of a C₁–

C₄ alcohol, a C₃–

C₈ ketone, water, and mixtures thereof.

12. The process of claim 10 wherein the polar solvent is a mixture of methanol and water.

13. The process of claim 7 wherein the organic hydroperoxide is t-butyl hydroperoxide and the alcohol is t-butyl alcohol.

14. The process of claim 7 wherein the titanium-containing silicon oxide catalyst is titania-on-silica.

15. The process of claim 7 wherein the alcohol is removed by distillation.