IP Library › Granted Patent US 12,435,279
Granted Patent B2
US 12,435,279 · App. 17/850,158 · Granted Oct 7, 2025

pH-modified water-soluble oxidized disulfide oil compositions

Inventors: Robert P. Hodgkins (Dhahran, SA); Omer Refa Koseoglu (Dhahran, SA)
Assignee: Saudi Arabian Oil Company
C10G19/02C10G2300/202C10G2300/207
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,435,279
App. No.
17/850,158
Granted
Oct 7, 2025
Kind
B2
Abstract

A composition of matter is provided including one or more water-soluble oxidized disulfide oil (WS-ODSO) compounds or mixture of compounds, and an effective amount of an alkaline agent. The composition is a pH-modified, that is, deacidified, neutralized or basified, WS-ODSO composition. The pH-modified WS-ODSO composition can be used as a component in synthesis of materials such as zeolitic materials.

Claims (22)

1. A composition comprising an aqueous mixture of one or more water-soluble oxidized disulfide oil (WS-ODSO) compounds and an effective amount of an alkaline agent, wherein the composition is a pH-modified WS-ODSO composition having a pH that is higher than a pH of the one or more WS-ODSO compounds.

2. The composition of claim 1 , wherein the one or more WS-ODSO compounds is selected from the group consisting of compounds having the general formula (R—SOO—SO—R′), (R—SOO—SOO—R′), (R—SO—SOO—OH), (R—SOO—SOO—OH), (R—SOO—SO—OH), (R′—SO—SO—OR), (R′—SOO—SO—OR), (R′—SO—SOO—OR) and (R′—SOO—SOO—OR), wherein R and R′ can be the same or different C1-C10 alkyl or C6-C10 aryl.

3. The composition of claim 1 , wherein the one or more WS-ODSO compounds is selected from the group consisting of compounds having the general formula (R—SOO—SO—R′), (R—SOO—SOO—R′), (R—SO—SOO—OH), (R—SOO—SOO—OH), (R—SO—SO—OH), (R—SOO—SO—OH), and mixtures thereof, where R and R′ are alkyl or aryl groups comprising 1-10 carbon atoms.

4. The composition of claim 1 , wherein the one or more WS-ODSO compounds comprises a mixture of two or more types of WS-ODSO compounds selected from the group consisting of compounds having the general formula (R—SOO—SO—R′), (R—SOO—SOO—R′), (R—SO—SOO—OH), (R—SOO—SOO—OH), (R—SOO—SO—OH), (R′—SO—SO—OR), (R′—SOO—SO—OR), (R′—SO—SOO—OR) and (R′—SOO—SOO—OR), wherein R and R′ can be the same or different C1-C10 alkyl or C6-C10 aryl.

5. The composition of claim 1 , wherein the one or more WS-ODSO compounds comprises a mixture of two or more types of WS-ODSO compounds selected from the group consisting of compounds having the general formula (R—SOO—SO—R′), (R—SOO—SOO—R′), (R—SO—SOO—OH), (R—SOO—SOO—OH), (R—SO—SO—OH), (R—SOO—SO—OH), and mixtures thereof, where R and R′ are alkyl or aryl groups comprising 1-10 carbon atoms.

6. The composition as in claim 4 , wherein the mixture is derived from oxidation of disulfide oil compounds present in an effluent refinery hydrocarbon stream recovered following catalytic oxidation of mercaptans present in a mercaptan-containing hydrocarbon stream.

7. The composition as in claim 1 , wherein the alkaline agent has a pH of greater than 7, and less than or equal to 14, and wherein the one or more WS-ODSO compounds have a pH of less than about 7.

8. The composition as in claim 1 , wherein the alkaline agent is selected from the group consisting of sodium hydroxide, calcium hydroxide, lithium hydroxide, strontium hydroxide, barium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, ammonia, ammonium hydroxide, zinc hydroxide, trimethylamine, pyridine, beryllium hydroxide, magnesium hydroxide, and mixtures comprising two or more of the foregoing.

9. The composition as in claim 1 , wherein the alkaline agent is sodium hydroxide.

10. The composition as in claim 1 that is a neutralized WS-ODSO composition having a pH in the range of about 6-8.

11. The composition as in claim 1 , wherein the effective amount of the alkaline agent is on a molar equivalent or approximately molar equivalent basis relative to the number of acid sites of the WS-ODSO compounds, and wherein the pH-modified WS-ODSO composition is a neutralized WS-ODSO composition.

12. The composition as in claim 1 , wherein the effective amount of the alkaline agent is greater than a molar equivalent relative to the number of acid sites of the WS-ODSO compounds, and wherein the pH-modified WS-ODSO composition is a basified WS-ODSO composition having a pH greater than 7.

13. The composition as in claim 1 , wherein the effective amount of the alkaline agent is less than a molar equivalent relative to the number of acid sites of the WS-ODSO compounds, and wherein the pH-modified WS-ODSO composition is a deacidified WS-ODSO composition having a pH less than 7.

14. The composition as in claim 1 , wherein all or a portion of water in the aqueous mixture is generated in-situ by reaction of WS-ODSO and alkaline agent.

15. The composition as in claim 6 , wherein the oxidation of disulfide oil compounds occurs in the presence of a transition metal catalyst, and wherein the pH-modified WS-ODSO contains transition metal from the transition metal catalyst.

16. The composition as in claim 15 , wherein the transition metal catalyst is selected from the group consisting of Mo, W, V, Ti, and combinations thereof.

17. The composition as in claim 1 , further comprising one or more one or more metals or metal compounds selected from the Periodic Table of the Elements IUPAC Groups 4-12.

18. The composition as in claim 1 , wherein the WS-ODSO contains a first weight percent of atomic sulfur, and the pH-modified WS-ODSO composition contains a lesser weight percent of atomic sulfur than the first quantity of atomic sulfur.

19. The composition as in claim 1 , wherein the alkaline agent comprises an alkali metal, the WS-ODSO contains a first weight percent of atomic alkali metal, and the pH-modified WS-ODSO composition contains a greater weight percent of atomic alkali metal than the first quantity of atomic alkali metal.

20. The composition as in claim 1 , wherein the alkaline agent has a pH of greater than 7, and less than or equal to 14, and wherein the one or more WS-ODSO compounds have a pH of less than about 4.

21. The composition as in claim 1 , wherein the alkaline agent has a pH of greater than or equal to about 8, and less than or equal to 14, and wherein the one or more WS-ODSO compounds have a pH of less than about 7.

22. The composition as in claim 1 , wherein the alkaline agent has a pH of greater than or equal to about 8, and less than or equal to 14, and wherein the one or more WS-ODSO compounds have a pH of less than about 4.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2022
From: HODGKINS, ROBERT P.; KOSEOGLU, OMER REFA
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 060321/0139 →
Continuity (1)
Related Publication 20230416616A1 · Dec 28, 2023
References Cited (37)
US 3313594A · Wilson · 1967 [cited by applicant]
US 3516786A · Maher et al. · 1970 [cited by applicant]
US 3556725A · Chiola et al. · 1971 [cited by applicant]
US 5763720A · Buchanan et al. · 1998 [cited by applicant]
US 5951962A · Müller et al. · 1999 [cited by applicant]
US 6337063B1 · Rouleau et al. · 2002 [cited by applicant]
US 7923522B2 · Hamada et al. · 2011 [cited by applicant]
US 10781168B2 · Koseoglu et al. · 2020 [cited by applicant]
US 10793782B2 · Koseoglu et al. · 2020 [cited by applicant]
US 10807947B2 · Koseoglu et al. · 2020 [cited by applicant]
US 10927318B2 · Koseoglu et al. · 2021 [cited by applicant]
US 11111212B2 · Koseoglu et al. · 2021 [cited by applicant]
US 11649405B1 · Hodgkins et al. · 2023 [cited by applicant]
US 11883806B2 · Hodgkins et al. · 2024 [cited by applicant]
US 11958751B2 · Hodgkins et al. · 2024 [cited by applicant]
US 11970403B2 · Hodgkins et al. · 2024 [cited by applicant]
US 20060254930A1 · Martinie et al. · 2006 [cited by applicant]
US 20150048006A1 · Zhang et al. · 2015 [cited by applicant]
US 20170369790A1 · Gomach · 2017 [cited by applicant]
US 20180312762A1 · Gomach · 2018 [cited by applicant]
US 20200181073A1 · Koseoglu et al. · 2020 [cited by applicant]
US 20200332201A1 · Koseoglu et al. · 2020 [cited by applicant]
US 20200332202A1 · Hodgkins et al. · 2020 [cited by applicant]
US 20200354638A1 · Koseoglu et al. · 2020 [cited by applicant]
US 20200377451A1 · Koseoglu · 2020 [cited by examiner]
US 20210071092A1 · Koseoglu et al. · 2021 [cited by applicant]
US 20210171841A1 · Koseoglu et al. · 2021 [cited by applicant]
US 20230331668A1 · Koseoglu et al. · 2023 [cited by applicant]
CN 102452663A · 2012 [cited by applicant]
CN 103055933A · 2013 [cited by applicant]
CN 106145134A · 2016 [cited by applicant]
CN 107982540A · 2018 [cited by applicant]
EP 0999183B1 · 2003 [cited by applicant]
WO 2018202468A1 · 2018 [cited by applicant]
Grabicka et al. “Microwave-assisted synthesis of periodic mesoporous organosilicas with ethane and disulfide groups.” Microporous and Mesoporous Materials 119.1-3 (2009): 144-149. [cited by applicant]
Jin et al. “Gold nanoparticles stabilized in a novel periodic mesoporous organosilica of SBA-15 for styrene epoxidation.” Microporous and Mesoporous Materials 111.1-3 (2008): 569-576. [cited by applicant]
Jo et al. “Synthesis of Silicate Zeolite Analogues Using Organic Sulfonium Compounds as Structure-Directing Agents.” Angewandte Chemie International Edition 54.43 (2015). Wiley Online Library, 12996-12999. 14 total page… [cited by applicant]