IP Library Granted Patent US 7,951,745
Granted Patent B2
US 7,951,745 · App. 11/968,861 · Granted May 31, 2011

Catalyst for hydrocracking hydrocarbons containing polynuclear aromatic compounds

Assignee: Wilmington Trust FSB
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Quick Facts
Patent No.
US 7,951,745
App. No.
11/968,861
Granted
May 31, 2011
Kind
B2
Abstract

Oil soluble catalysts are used to convert polynuclear aromatic compounds in a hydrocarbon feedstock to higher value mono-aromatic compounds. The catalyst complex includes a catalytic metal center that is bonded to a plurality of organic ligands that make the catalyst complex oil-soluble. The ligands include an aromatic ring and a ligand spacer group. The ligand spacer group provides spacing of 2-6 atoms between the metal center and the aromatic ring. The spacing between the aromatic group and the catalytic metal center advantageously allows the catalyst to selectively crack polynuclear aromatic rings while preserving one of the aromatic rings, thereby increasing the content of mono-aromatic compounds in the hydrocarbon feedstock.

Claims (44)

1. An oil-soluble catalyst for hydrocracking a hydrocarbon feedstock containing polynuclear-aromatics, comprising:

an oil-soluble catalyst complex comprised of:

a first catalytic metal atom selected from the group consisting of group VIB metals, group VIIIB metals, and combinations thereof;

a second catalytic metal atom selected from the group consisting of group VIB metals, group VIIIB metals, and combinations thereof; and

an organic ligand bonded with the first and second catalytic metal atoms, wherein the organic ligand is comprised of:

an aromatic group;

a first ligand spacing group bonded to the aromatic group, the ligand spacing group having an atom bonded to the first metal atom and another atom bonded to the aromatic group and providing separation of 2-6 atoms between the first metal atom and the aromatic group; and

a second ligand spacing group bonded to the aromatic group, the ligand spacing group having an atom bonded to the second metal atom and another atom bonded to the aromatic group and providing separation of 2-6 atoms between the second metal atom and the aromatic group.

2. A catalyst as in claim 1 , wherein the first ligand spacing group comprises an acid residue group.

3. A catalyst as in claim 2 , wherein the acid residue comprises B, N, P, S, or C.

4. A catalyst as in claim 1 , wherein the first ligand spacing group comprises at least one side group.

5. A catalyst as in claim 4 , wherein the side group comprises an oxygen or an alkoxy group.

6. A catalyst as in claim 1 , wherein the aromatic group comprises a five member or six member ring.

7. A catalyst as in claim 1 , wherein the aromatic group is alkylated.

8. A catalyst as in claim 1 , wherein at least one of the first or second catalytic metal atoms is selected from the group consisting of tungsten (W), molybdenum (Mo), chromium (Cr), nickel (Ni), cobalt (Co), iron (Fe), vanadium (V), titanium (Ti), manganese (Mn), and combinations thereof.

9. A catalyst as in claim 1 , wherein the catalyst complex comprises at least two different types of catalytic metal atoms.

10. A catalyst as in claim 9 , wherein the metal atoms comprise Mo and at least one other Group VIB or Group VIIIB metal.

11. A catalyst as in claim 1 , wherein the catalyst includes a plurality of oil-soluble catalyst complexes and wherein at least some of the oil-soluble catalyst complexes are linked together so as to form an extended network of intercomplexed ligands and metal atoms.

12. A catalyst as in claim 1 , wherein the aromatic group includes a benzene ring.

13. A method for increasing the monoaromatic content of a hydrocarbon material containing polynuclear aromatic compounds comprising hydrocracking the hydrocarbon material in the presence of the catalyst of claim 1 or a derivative thereof.

14. A method as in claim 13 , wherein the concentration of catalyst in the hydrocarbon material during hydrocracking is in a range from about 1 ppm to about 1,000 ppm.

15. An oil soluble catalyst comprising a complex according to the following structure:

wherein,

M is a group VIB metal, a group VIIIB metal, or a base transition metal;

R 1 -R 10 are independently a hydrogen, an alkyl group, or a bond to a ligand spacing group that is bonded to another metal atom;

A 1 and A 2 comprise a single atom or a chain of atoms, at least one of the atoms being selected from the group consisting of B, N, P, S, group IIIA elements, group IVA elements, group VA elements, and group VIA elements;

R 11 -R 14 are independently a single bonded oxygen, a double bonded oxygen, or an alkoxide; and

X 1 -X 4 are optional ligands bonded to the catalytic metal.

16. An oil soluble catalyst as in claim 15 , wherein M is W, Mo, Cr, Ni, Co, Fe, V, Ti, or Mn.

17. A catalyst as in claim 15 , wherein at least one of R 1 -R 6 and one R 7 -R 10 are an alkyl group having between 1 and 12 carbons.

18. A catalyst as in claim 15 , wherein the catalyst comprises a plurality of oil-soluble catalyst complexes linked together to form an extended network of intercomplexed ligands and metal atoms.

19. A method for increasing the mono-aromatic content of a hydrocarbon material containing polynuclear aromatics, comprising hydrocracking the hydrocarbon material in the presence of the catalyst of claim 15 .

20. A method as in claim 19 , wherein the concentration of catalyst in the hydrocarbon material during hydrocracking is in a range from about 1 ppm to about 1,000 ppm.

21. A catalyst for hydrocracking a hydrocarbon feedstock containing polynuclear-aromatics, comprising:

a plurality of oil soluble catalyst complexes comprised of,

a plurality of catalytic metal atoms comprising Mo and at least one other Group VIB or Group VIIIB metal;

a plurality of organic ligands complexed with each of the metal atoms, each organic ligand comprising,

an aromatic group; and

at least one ligand spacer group bonded to the aromatic group, wherein the ligand spacer group is comprised of an acid residue that is bonded to the aromatic group and to the metal atom and wherein the spacer group provides separation of 2-4 atoms between the metal atom and the aromatic group,

wherein at least some of the oil-soluble catalyst complexes are linked together to form an extended network of intercomplexed ligands and metal atoms.

22. A catalyst as in claim 21 , wherein the acid residue comprises a side chain group.

23. A catalyst as in claim 21 , wherein a molar ratio of the Mo to the at least one other Group VIB or Group VIIIB metal is in a range from about 50:1 to about 1:20.

24. A catalyst as in claim 21 , wherein the aromatic group includes a benzene ring.

25. A method for increasing the monoaromatic content of a hydrocarbon material containing polynuclear aromatics, comprising hydrocracking the hydrocarbon material in the presence of the catalyst of claim 21 .

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2018
From: HEADWATERS TECHNOLOGY INNOVATION GROUP, INC.
To: HYDROCARBON TECHNOLOGY & INNOVATION, LLC
Reel/Frame 045190/0167 →
RELEASE OF SECURITY INTEREST Recorded May 8, 2017
From: DEUTSCHE BANK AG NEW YORK BRANCH
To: HEADWATERS TECHNOLOGY INNOVATION GROUP, INC.; HEADWATERS HEAVY OIL, LLC
Reel/Frame 042422/0740 →
SECURITY AGREEMENT Recorded Sep 17, 2015
From: HEADWATERS TECHNOLOGY INNOVATION GROUP, INC.
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 036628/0277 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2015
From: HEADWATERS TECHNOLOGY INNOVATION, LLC
To: HEADWATERS TECHNOLOGY INNOVATION GROUP, INC.
Reel/Frame 035492/0219 →
PATENT RELEASE (REEL:23699/FRAME:0452) Recorded Mar 26, 2015
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: HEADWATERS INCORPORATED, AS GRANTOR; HEADWATERS RESOURCES, INC., A UTAH CORPORATION; HEADWATERS TECHNOLOGY INNOVATION GROUP, INC., A UTAH CORPORATION; HEADWATERS HEAVY OIL, LLC, A UTAH CORPORATION; TAPCO INTERNATIONAL CORPORATION, A MICHIGAN CORPORATION
Reel/Frame 035306/0558 →
SECURITY AGREEMENT Recorded Nov 20, 2009
From: HEADWATERS INCORPORATED, A DELAWARE CORPORATION; HEADWATERS CTL, LLC, A UTAH LIMITED LIABILITY COMPANY, USA; HEADWATERS HEAVY OIL, LLC, A UTAH LIMITED LIABILITY COMPANY, USA; HEADWATERS RESOURCES, INC., A UTAH CORPORATION, USA; HEADWATERS TECHNOLOGY INNOVATION GROUP, INC., A UTAH CORPORATION, USA; TAPCO INTERNATIONAL CORPORATION, A MICHIGAN CORPORATION, USA
To: WILMINGTON TRUST FSB, AS COLLATERAL AGENT
Reel/Frame 023699/0452 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2008
From: ZHOU, BING; ZHOU, ZHENHUA; WU, ZHIHUA
To: HEADWATERS TECHNOLOGY INNOVATION LLC
Reel/Frame 020340/0926 →
Continuity (1)
Related Publication 20090173665A1 · Jul 9, 2009