IP Library › Granted Patent US 12,275,679
Granted Patent B2
US 12,275,679 · App. 18/659,092 · Granted Apr 15, 2025

Transition metal-catalyzed production of alcohol and carbonyl compounds from hydrocarbons

Inventors: Masud M. Monwar (Bartlesville, OK); Jared L. Barr (Bartlesville, OK); Carlos A. Cruz (Kingwood, TX); Kathy S. Clear (Bartlesville, OK); Max P. McDaniel (Bartlesville, OK); William C. Ellis (Bartlesville, OK)
Assignee: Chevron Phillips Chemical Company LP
C07B33/00B01J21/063B01J21/08B01J21/12B01J23/22B01J23/28B01J23/30B01J35/39B01J35/613B01J35/615B01J35/617B01J35/618B01J35/633B01J35/635B01J35/638B01J37/082B01J37/16B01J37/34B01J37/345B01J38/02C07C29/48C07C29/50C07C45/27C07C45/28C07C51/16C07C51/225
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Quick Facts
Patent No.
US 12,275,679
App. No.
18/659,092
Granted
Apr 15, 2025
Kind
B2
Abstract

Processes for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound are disclosed in which the hydrocarbon reactant and a supported transition metal catalyst—containing molybdenum, tungsten, or vanadium—are irradiated with a light beam at a wavelength in the UV-visible spectrum, optionally in an oxidizing atmosphere, to form a reduced transition metal catalyst, followed by hydrolyzing the reduced transition metal catalyst to form a reaction product containing the alcohol compound and/or the carbonyl compound.

Claims (41)

1. A supported transition metal catalyst comprising:

a solid support; and

from 0.01 to 50 wt. % of a transition metal comprising molybdenum, tungsten, vanadium, or a combination thereof, based on the weight of the catalyst; wherein:

at least one bonding site on the transition metal has a ligand characterized by the following formula: —O-Hydrocarbon group; and

a molar ratio of the hydrocarbon group to transition metal is in a range from 0.25:1 to 2:1.

2. The catalyst of claim 1 , wherein:

the supported transition metal catalyst comprises from 0.1 to 5 wt. % of transition metal, based on the weight of the supported transition metal catalyst.

3. The catalyst of claim 1 , wherein the solid support comprises a solid oxide, a chemically-treated solid oxide, a zeolite, or any combination thereof.

4. The catalyst of claim 1 , wherein the transition metal comprises molybdenum.

5. The catalyst of claim 1 , wherein the transition metal comprises tungsten.

6. The catalyst of claim 1 , wherein the transition metal comprises vanadium.

7. The catalyst of claim 1 , wherein the solid support is a silica, a silica-coated alumina, or a combination thereof.

8. The catalyst of claim 1 , wherein the supported transition metal catalyst comprises from 0.1 to 15 wt. % of transition metal, based on the weight of the supported transition metal catalyst.

9. The catalyst of claim 8 , wherein the molar ratio of the hydrocarbon group to transition metal is in a range from 0.5:1 to 1.5:1.

10. The catalyst of claim 9 , wherein the solid support comprises a silica, a silica-coated alumina, or a combination thereof.

11. The catalyst of claim 8 , wherein the solid support is a solid oxide, a chemically-treated solid oxide, a zeolite, or any combination thereof.

12. The catalyst of claim 11 , wherein the transition metal comprises molybdenum.

13. The catalyst of claim 11 , wherein the transition metal comprises tungsten.

14. The catalyst of claim 11 , wherein the transition metal comprises vanadium.

15. A supported transition metal catalyst comprising:

a solid support; and

from 0.1 to 5 wt. % of a transition metal comprising molybdenum, tungsten, vanadium, or a combination thereof, based on the weight of the catalyst; wherein:

at least one bonding site on the transition metal has a ligand characterized by one of the following formulas: —O-Hydrocarbon group or —O-Halogenated hydrocarbon group.

16. The catalyst of claim 15 , wherein the solid support comprises a solid oxide, a chemically-treated solid oxide, a zeolite, or any combination thereof.

17. The catalyst of claim 16 , wherein the transition metal comprises molybdenum.

18. The catalyst of claim 16 , wherein the transition metal comprises tungsten.

19. The catalyst of claim 16 , wherein the transition metal comprises vanadium.

20. The catalyst of claim 15 , wherein the solid support comprises a silica, a silica-coated alumina, or a combination thereof.

21. The catalyst of claim 20 , wherein the transition metal comprises molybdenum.

22. The catalyst of claim 20 , wherein the transition metal comprises tungsten.

23. The catalyst of claim 20 , wherein the transition metal comprises vanadium.

24. A supported transition metal catalyst comprising:

a solid support; and

from 0.01 to 50 wt. % of a transition metal comprising molybdenum, tungsten, vanadium, or a combination thereof, based on the weight of the catalyst; wherein:

at least one bonding site on the transition metal has a ligand characterized by the following formula: —O-Halogenated hydrocarbon group.

25. The catalyst of claim 24 , wherein the solid support comprises a solid oxide, a chemically-treated solid oxide, a zeolite, or any combination thereof.

26. The catalyst of claim 25 , wherein the transition metal comprises molybdenum.

27. The catalyst of claim 25 , wherein the transition metal comprises tungsten.

28. The catalyst of claim 25 , wherein the transition metal comprises vanadium.

29. The catalyst of claim 24 , wherein the supported transition metal catalyst comprises from 0.1 to 15 wt. % of transition metal, based on the weight of the supported transition metal catalyst.

30. The catalyst of claim 29 , wherein the solid support comprises a silica, a silica-coated alumina, or a combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2024
From: MONWAR, MASUD M.; BARR, JARED L.; CRUZ, CARLOS A.; CLEAR, KATHY S.; MCDANIEL, MAX P.
To: CHEVRON PHILLIPS CHEMICAL COMPANY LP
Reel/Frame 068341/0449 →
Continuity (4)
Division 18459534 · Sep 1, 2023
Division 17470066 · Sep 9, 2021
Provisional Application 63077761 · Sep 14, 2020
Related Publication 20240286973A1 · Aug 29, 2024
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