# US 11,439,994 B2 · Method for the hydrogenation of aromatics using a nickel-based catalyst

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,439,994 B2
- Document ID: US11439994B2
- Status: Granted
- Kind: B2
- Application number: 17/074,871
- Filed: 2020-10-20
- Published: 2021-02-04
- Granted: 2022-09-13
- Earliest claimed: 2016-12-22
- Assignees: Ifp Energies Nouvelles
- Applicants: IFP Energies Nouvelles
- Inventors: Anne-Claire Dubreuil; Agathe Martel
- Web page: https://patentgrep.com/patent/US11439994B2

## CPC

- B01J 37/0203: {the impregnation liquid containing organic compounds}
- B01J 21/04: Alumina
- B01J 23/755: Nickel
- B01J 35/393: {Metal or metal oxide crystallite size}
- B01J 37/0205: {in several steps}
- B01J 37/0236: {Drying, e.g. preparing a suspension, adding a soluble salt and drying}
- B01J 37/08: Heat treatment {(B01J37/0009, B01J37/0018 take precedence)}
- C07C 5/10: of aromatic six-membered rings
- C10G 45/48: containing nickel or cobalt metal, or compounds thereof
- B01J 2235/00: Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
- B01J 2235/15: X-ray diffraction
- C07C 2521/04: Alumina
- C07C 2523/755: Nickel
- C10G 2300/1096: Aromatics or polyaromatics
- C10G 2300/70: Catalyst aspects
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

## Abstract

Hydrogenation of at least one aromatic or polyaromatic compound contained in a hydrocarbon feedstock having a final boiling point below or equal to 650° C., at a temperature of between 30 and 350° C., at a pressure of between 0.1 and 20 MPa, at a hydrogen/(aromatic compounds to be hydrogenated) molar ratio between 0.1 and 10 and at an hourly space velocity HSV of between 0.05 and 50 h−1, in the presence of a catalyst comprising an alumina support and an active phase comprising nickel, prepared by i) contacting the support with a solution containing a nickel precursor; ii) bringing the support into contact with a solution containing an organic compound comprising a carboxylic acid, or alcohol, or ester, or amide function; iii) drying the impregnated support at a temperature below 250° C.; i) and ii) being carried out separately, in any order, or at the same time.

## Claims

### Claim 1

A process comprising hydrogenation of at least one aromatic or polyaromatic compound contained in a hydrocarbon feedstock having a final boiling point below or equal to 650° C., said process being carried out in gas phase or in liquid phase, at a temperature of 30 to 350° C., at a pressure of 0.1 to 20 MPa, at a hydrogen/(aromatic compounds to be hydrogenated) molar ratio of 0.1 to 10 and at an hourly space velocity HSV of 0.05 to 50 h−1, in the presence of a catalyst comprising an alumina support and an active phase comprising nickel, said active phase not comprising a metal from Group VIB, said process comprising:
a) first preparing said catalyst by at least:
i) bringing said alumina support into contact with at least one solution containing at least one nickel precursor,
ii) bringing said alumina support into contact with at least one solution containing at least one organic compound comprising at least one carboxylic acid functional group;
whereby after i) and ii) an impregnated support is produced,
iii) drying said impregnated support at a temperature below 180° C.;
i) and ii) being carried out separately, in any order, or at the same time, with the proviso that the catalyst is not calcined under a calcination temperature range of 250° C.-1000° C., thereby producing an uncalcined catalyst, and
b) hydrogenating the at least one aromatic or polyaromatic compound contained in the hydrocarbon feedstock with the uncalcined catalyst.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein i) and ii) are carried out at the same time.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein i) is carried out before ii).

### Claim 4 (depends on 1)

The process as claimed in claim 1 wherein ii) is carried out before i).

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein i) and/or ii) is (are) carried out by dry impregnation.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein a content of element nickel is 8 to 65% by weight relative to a total weight of the catalyst.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein said organic compound is at least one monocarboxylic acid, dicarboxylic acid, tricarboxylic acid or tetracarboxylic acid.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein said organic compound further comprises at least one alcohol functional group.

### Claim 9 (depends on 8)

The process as claimed in claim 8, wherein said organic compound further comprises:
organic compounds having a single alcohol functional group;
organic compounds having two alcohol functional groups;
diethylene glycol, triethylene glycol, tetraethylene glycol or a polyethylene glycol corresponding to the formula H(OC2H4)nOH with n greater than 4 and having an average molar mass of less than 20 000 g/mol;
monosaccharides of empirical formula Cn(H2O)n with n between 3 and 12; or
disaccharides, trisaccharides, or monosaccharide derivatives.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein said organic compound further comprises at least one ester functional group.

### Claim 11 (depends on 10)

The process as claimed in claim 10, wherein said organic compound further comprises:
carboxylic acid linear or cyclic or unsaturated cyclic esters;
organic compounds having at least two carboxylic acid ester functional groups;
organic compounds having at least one carboxylic acid ester functional group and at least one second functional group from alcohols, ethers, ketones or aldehydes;
carbonic acid cyclic or linear esters; or
carbonic acid linear diesters.

### Claim 12 (depends on 1)

The process as claimed in claim 1, wherein said organic compound further comprises at least one amide functional group.

### Claim 13 (depends on 12)

The process as claimed in claim 12, wherein said organic compound further comprises:
acyclic amides having one or two amide functional groups;
cyclic amides or lactams;
organic compounds having at least one amide functional group and a carboxylic acid functional group or an alcohol functional group; or
organic compounds having at least one amide functional group and an additional nitrogen heteroatom.

### Claim 14 (depends on 1)

The process as claimed in claim 1, comprising an aromatic hydrogenation of benzene at a temperature of 30 to 250° C., at a pressure of 0.1 to 10 MPa, at a hydrogen/(benzene) molar ratio of 0.1 to 10 and at an hourly space velocity HSV of 0.05 to 50 h−1.