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

Patent metadata

Field	Value
Publication number	US-11780786-B2
Application number	US-202117470066-A
Country	US
Kind code	B2
Filing date	Sep 9, 2021
Priority date	Sep 14, 2020
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

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.

First claim

We claim:

1. A process for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound, the process comprising:
(i) irradiating the hydrocarbon reactant and a supported transition metal catalyst comprising molybdenum, tungsten, vanadium, or a combination thereof, with a light beam at a wavelength in the UV-visible spectrum to reduce at least a portion of the supported transition metal catalyst to form a reduced transition metal catalyst; and
(ii) hydrolyzing the reduced transition metal catalyst to form a reaction product comprising the alcohol compound and/or the carbonyl compound.

2. The process of claim 1 , wherein step (i) comprises irradiating the hydrocarbon reactant and the supported transition metal catalyst in an oxidizing atmosphere.

3. The process of claim 1 , wherein the hydrocarbon reactant comprises a C 1 to C 36 linear, branched, or cyclic alkane compound.

4. The process of claim 1 , wherein the hydrocarbon reactant comprises a C 2 to C 36 olefin compound, a C 6 to C 36 aromatic compound, or any combination thereof.

5. The process of claim 1 , wherein the supported transition metal catalyst contains from 0.01 to 50 wt. % of molybdenum, tungsten, vanadium, or a combination thereof, based on the weight of the supported transition metal catalyst.

6. The process of claim 1 , wherein:
the supported transition metal catalyst comprises a solid oxide, a chemically-treated solid oxide, a zeolite, or a combination thereof;
the supported transition metal catalyst has a pore volume from 0.1 to 5 mL/g and a BET surface area from 50 to 2000 m 2 /g; and
the irradiating step is conducted at a temperature from −100° C. to 100° C.

7. The process of claim 1 , wherein;
the light beam is from a blue light source or a UV light source;
the light beam comprises wavelengths above 350 nm and below 500 nm;
the hydrocarbon reactant and the supported transition metal catalyst are irradiated with an illuminance of at least 5000 lux; or
any combination thereof.

8. The process of claim 1 , wherein the process comprises:
contacting the hydrocarbon reactant with a fluidized bed of the supported transition metal catalyst, and irradiating while contacting; or
contacting the hydrocarbon reactant with a fixed bed of the supported transition metal catalyst, and irradiating while contacting.

9. The process of claim 1 , wherein:
hydrolyzing is conducted at a temperature from 0° C. to 100° C.; and
hydrolyzing comprises contacting the reduced transition metal catalyst with a hydrolysis agent comprising water, steam, an alcohol agent, an acid agent, an alkaline agent, or any combination thereof.

10. The process of claim 1 , further comprising a step of separating at least a portion of the alcohol compound and/or the carbonyl compound from the reaction product after step (ii).

11. The process of claim 1 , further comprising a step of separating at least a portion of the hydrocarbon reactant from the reaction product after step (ii), and wherein the at least a portion of the hydrocarbon reactant is recycled and irradiated with the supported transition metal catalyst again.

12. The process of claim 1 , further comprising:
separating at least a portion of the reduced transition metal catalyst from the reaction product after step (ii); and
calcining the at least a portion of the reduced transition metal catalyst to regenerate the supported transition metal catalyst.

13. The process of claim 1 , wherein:
a conversion of the hydrocarbon reactant is at least 10 wt. %; and/or
a molar yield of the alcohol compound and/or the carbonyl compound is from 0.01 to 5 moles of the alcohol compound and/or the carbonyl compound per mole of transition metal in the supported transition metal catalyst.

14. The process of claim 1 , wherein the supported transition metal catalyst comprises vanadium.

15. A process for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound, the process comprising:
(I) irradiating the hydrocarbon reactant and a supported transition metal catalyst comprising molybdenum, tungsten, vanadium, or a combination thereof, with a light beam at a wavelength in the UV-visible spectrum to reduce at least a portion of the supported transition metal catalyst to form a reduced transition metal catalyst;
(II) subjecting the reduced transition metal catalyst to an oxidizing atmosphere; and
(III) hydrolyzing the reduced transition metal catalyst to form a reaction product comprising the alcohol compound and/or the carbonyl compound.

16. The process of claim 15 , wherein;
the light beam is from a blue light source or a UV light source;
the light beam comprises wavelengths above 350 nm and below 500 nm;
the hydrocarbon reactant and the supported transition metal catalyst are irradiated with an illuminance of at least 5000 lux; or
any combination thereof.

17. The process of claim 15 , wherein:
a conversion of the hydrocarbon reactant is at least 10 wt. %; and/or
a molar yield of the alcohol compound and/or the carbonyl compound is from 0.01 to 5 moles of the alcohol compound and/or the carbonyl compound per mole of transition metal in the supported transition metal catalyst.

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Monwar Masud M
• Barr Jared L
• Cruz Carlos A
• Clear Kathy S
• Mcdaniel Max P
• Ellis William Chad

Classifications

• B01J37/34

  Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves {; Ionic sputtering; Flame or plasma spraying; Particle radiation} · CPC title

• B01J37/16

  Reducing · CPC title

• C07C51/16

  by oxidation (C07C51/145 takes precedence) · CPC title

• C07C45/27

  by oxidation (with ozone C07C45/40) · CPC title

• C07C29/48

  by oxidation reactions with formation of hydroxy groups · CPC title