# US 10,246,647 B2 · Adsorbents and methods of use

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- Number: US 10,246,647 B2
- Document ID: US10246647B2
- Status: Granted
- Kind: B2
- Application number: 15/080,784
- Filed: 2016-03-25
- Published: 2016-09-29
- Granted: 2019-04-02
- Earliest claimed: 2015-03-26
- Assignees: Auterra, Inc.; Cenovus Energy Inc.
- Applicants: Auterra, Inc.; Cenovus Energy Inc.
- Inventors: Kyle E. Litz; Jonathan P. Rankin; Erica H. Shipley; Michael Scudder; Trent A. McCaskill
- Web page: https://patentgrep.com/patent/US10246647B2

## CPC

- C10G 25/003: {Specific sorbent material, not covered by C10G25/02 or C10G25/03}
- B01J 20/0211: {Compounds of Ti, Zr, Hf}
- C10G 25/12: Recovery of used adsorbent
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Systems, methods and compositions for reducing the heteroatom content of hydrocarbon feed using transition metal complexes and adsorption techniques. The transition metal complexes include titanyl, hafnyl and zirconyl complexes activated using one or more hydroperoxides or peracids. The activated adsorbents are incorporated into one or more vessels as an adsorption bed for adsorbing the heteroatoms present in hydrocarbon feeds. The systems, methods and compositions separate the heteroatoms passed through the system by contacting the adsorption compositions with the heteroatoms of the hydrocarbon feed, adsorbing the heteroatom to the adsorption material, further allowing for the retrieval of a hydrocarbon product having a reduced heteroatom content.

## Claims

### Claim 1

A method for reducing a heteroatom content of a hydrocarbon feed comprising the steps of:
providing an adsorbent having a metal complex bound to an inorganic oxide support, wherein the metal complex is a titanyl having a titanium molecule covalently bonded to an alcohol or polyol;
contacting the adsorbent with a hydroperoxide or a peracid, forming an activated adsorbent;
contacting the activated adsorbent with the hydrocarbon feed;
binding a heteroatom present in the hydrocarbon feed to the activated adsorbent, forming a heteroatom-bound adsorbent, leaving behind a hydrocarbon feed having a reduced heteroatom content; and
separating the hydrocarbon feed having the reduced heteroatom content from the heteroatom-bound adsorbent.

### Claim 2 (depends on 1)

The method of claim 1, further comprising the step:
contacting the heteroatom bound adsorbent with a solvent, the solvent removing the heteroatom from the heteroatom-bound adsorbent, forming a regenerated activated adsorbent.

### Claim 3 (depends on 2)

The method of claim 2, wherein the solvent is a hydroperoxide or peracid.

### Claim 4 (depends on 2)

The method of claim 2, further comprising the step of:
separating the heteroatom dissolved in the solvent from the regenerated activated adsorbent.

### Claim 5 (depends on 2)

The method of claim 2, further comprising the steps of:
contacting the regenerated activated adsorbent with a second hydrocarbon feed; and
binding a heteroatom of the second hydrocarbon feed to the regenerated activated adsorbent.

### Claim 6 (depends on 1)

The method of claim 1, wherein the metal complex is selected from the group consisting of bis(glycerolato)oxotitanium(IV), bis(sorbitolato)oxotitanium(iv), bis(erythritolato)oxotitanium (IV), bis(mannitolato)oxotitanium(IV) and combinations thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein hydroperoxide or peracid is selected from the group consisting of hydrogen peroxide, tert-butyl hydroperoxide, ethylbenzene hydroperoxide, cumyl hydroperoxide, tetrahydronaphthalene hydroperoxide, performic acid, peracetic acid and combinations thereof.

### Claim 8 (depends on 1)

The method of claim 1, wherein the metal complex of the activated adsorbent is bis(polyol)(tert-butyl hydroperoxo)oxotitanium(IV), bis(polyol)(ethylbenzene hydroperoxo)oxotitanium(IV), bis(polyol)(cumyl hydroperoxo)oxotitanium(IV) or bis(polyol)(tetrahydronaphthalene hydroperoxo)oxotitanium(IV).

### Claim 9 (depends on 1)

The method of claim 1, wherein heteroatom content of the hydrocarbon feed is reduced by at least 85%.