Oxidized disulfide oil solvent compositions

Patent metadata

Field	Value
Publication number	US-11111212-B2
Application number	US-202016995048-A
Country	US
Kind code	B2
Filing date	Aug 17, 2020
Priority date	Dec 5, 2018
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

Oxidized disulfide oil (ODSO) solvent compositions are derived from by-product disulfide oil (DSO) compounds produced as by-products from the generalized mercaptan oxidation (MEROX) processing of a refinery feedstock. The oxidized disulfide oil (ODSO) solvent compositions comprise at least a primary oxidized disulfide oil (ODSO) compound selected from either water soluble or water insoluble oxidized disulfide oil (ODSO) compounds and in some embodiments at least 0.1 ppmw of a secondary oxidized disulfide oil (ODSO) compound that is a water soluble oxidized disulfide oil (ODSO) compound.

First claim

We claim:

1. An oxidized disulfide oil (ODSO) mixture consisting of two or more primary oxidized disulfide oil (ODSO) compounds selected from the group consisting of
(R—SO—S—R′), (R—SOO—S—R′), (R—SOO—SO—R′),
(R—SOO—SOO—R′), (R—SO—SO—R′), (R—SO—SOO—OH),
(R—SOO—SOO—OH), (R—SO—SO—OH), and (R—SOO—SO—OH), and mixtures thereof, and
at least one of a secondary oxidized disulfide oil (ODSO) compound selected from the group consisting of
(R—SOO—SO—R′),
(R—SOO—SOO—R′), (R—SO—SO—OH),
(R—SOO—SOO—OH), (R—SO—SO—OH), and (R—SOO—SO—OH), and mixtures thereof,
where R and R′ are alkyl groups each of which comprises from 1-10 carbon atoms,
and wherein the ODSO compounds in the mixture correspond to oxidized disulfide oils present in an effluent refinery hydrocarbon stream recovered following the catalytic oxidation of mercaptans present in the hydrocarbon stream.

2. The ODSO mixture of claim 1 , wherein the at least one secondary ODSO compound is present at a concentration of at least 0.1 ppmw.

3. The ODSO mixture of claim 1 , wherein the mixture comprises water soluble and water insoluble compounds.

4. The ODSO mixture of claim 1 , wherein the mixture has a dielectric constant that is less than or equal to 100 at 0° C.

5. The ODSO mixture of claim 1 , wherein the number of oxygen atoms in the two or more primary ODSO compound is in the range of from 1 to 5.

6. The ODSO mixture of claim 1 , wherein the disulfide oils are oxidized in the presence of a catalyst.

7. The ODSO mixture of claim 6 , wherein the catalyzed oxidation of the disulfide oils utilizes one or more heterogeneous or homogeneous catalysts comprising metals from IUPAC Groups 4-12 of the Periodic Table.

8. The ODSO mixture of claim 1 , wherein the catalyst is sodium tungstate.

9. The ODSO solvent composition of claim 1 , wherein the oxidation of the disulfide oils is carried out in an oxidation vessel selected from one or more of fixed-bed reactors, ebullated bed reactors, slurry bed reactors, moving bed reactors, continuous stirred tank reactors, and tubular reactors.

10. The ODSO mixture of claim 1 , wherein the oxidation of the disulfide oils is carried out at a pressure in the range of from about 1 bar to 30 bars.

11. The ODSO mixture of claim 1 , wherein the oxidation of the disulfide oils is carried out at a temperature in the range of from about 20° C. to 300° C.

12. The ODSO mixture of claim 1 , wherein the oxidation of the disulfide oils is carried out at a molar feed ratio of oxidizing agent-to-mono-sulfur in the range of from about 1:1 to about 100:1.

13. The ODSO mixture of claim 1 , wherein the oxidation of the disulfide oils is carried out in a residence time of about 5 to 180 minutes.

14. The ODSO mixture of claim 1 , wherein the at least one secondary ODSO compounds are present in an amount in the range of from 0.1 ppmw to 10 ppmw.

Assignees

• Saudi Arabian Oil Co

Inventors

• Koseoglu Omer Refa
• Hodgkins Robert Peter
• Al-Hajji Adnan
• Muller Hendrik
• Al-Awani Nadrah
• Adam Frederick Marie
• Saleem Qasim

Classifications

• C07C2531/34

  of chromium, molybdenum or tungsten · CPC title

• C07C327/60 Primary

  Thiocarboxylic acids having sulfur atoms of thiocarboxyl groups further doubly-bound to oxygen atoms · CPC title

• C07C327/22

  having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C381/02

  Thiosulfates · CPC title

• C07C381/04

  Thiosulfonates · CPC title