# US 10,501,388 B2 · Process for producing BTX from a C5—C12 hydrocarbon mixture

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- Number: US 10,501,388 B2
- Document ID: US10501388B2
- Status: Granted
- Kind: B2
- Application number: 15/749,240
- Filed: 2016-08-18
- Published: 2018-08-16
- Granted: 2019-12-10
- Earliest claimed: 2015-08-21
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Alla Khanmamedova; Scott A. Stevenson; Dustin Fickel
- Web page: https://patentgrep.com/patent/US10501388B2

## CPC

- C07C 4/18: Catalytic processes
- B01J 23/56: Platinum group metals
- B01J 29/44: Noble metals
- B01J 35/40: characterised by dimensions, e.g. grain size (in a colloidal state B01J35/23; crystallite size B01J35/77)
- C07C 4/06: Catalytic processes {(C07C4/025 takes precedence)}
- C07C 4/08: by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C 4/14: splitting taking place at an aromatic-aliphatic bond
- C07C 5/13: with simultaneous isomerisation
- C07C 5/41: Catalytic processes
- C07C 15/04: Benzene
- C07C 15/06: Toluene
- C07C 15/08: Xylenes
- C10G 35/085: containing platinum group metals or compounds thereof
- C10G 35/095: containing crystalline alumino-silicates, e.g. molecular sieves {(C10G35/065 takes precedence)}
- C10G 45/62: containing platinum group metals or compounds thereof
- C10G 45/64: containing crystalline alumino-silicates, e.g. molecular sieves
- C10G 45/70: with catalysts containing platinum group metals or compounds thereof
- C10G 47/18: the catalyst containing platinum group metals or compounds thereof
- B01J 2229/186: not in framework positions
- B01J 2229/20: to introduce other elements in the catalyst composition comprising the molecular sieve, but not specially in or on the molecular sieve itself
- B01J 2229/42: Addition of matrix or binder particles
- C10G 2300/1044: Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
- C10G 2400/30: Aromatics
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to a process for producing benzene comprising the steps of: (a) providing a hydrocracking feed stream comprising C5-C12 hydrocarbons, (b) contacting the hydrocracking feed stream in the presence of hydrogen with a hydrocracking catalyst under process conditions including a temperature of 425-580° C., a pressure of 300-5000 kPa gauge and a Weight Hourly Space Velocity of 3-30 h−1 to produce a hydrocracking product stream comprising BTX and (c) separating the BTX from the hydrocracking product stream, wherein the hydrocracking catalyst comprises a shaped body comprising a zeolite and a binder and a hydrogenation metal deposited on the shaped body, wherein the amount of the hydrogenation metal is 0.010-0.30 wt-% with respect to the total catalyst and wherein the zeolite is ZSM-5 having a silica (SiO2) to alumina (Al2O3) molar ratio of 25-75.

## Claims

### Claim 1

A process for producing benzene comprising the steps of:
(a) providing a hydrocracking feed stream comprising C5-C12 hydrocarbons,
(b) contacting the hydrocracking feed stream in the presence of hydrogen with a hydrocracking catalyst under process conditions including a temperature of 425-580° C., a pressure of 300-5000 kPa gauge and a Weight Hourly Space Velocity of 3-30 h−1 to produce a hydrocracking product stream comprising BTX, and
(c) separating the BTX from the hydrocracking product stream,
wherein the hydrocracking catalyst comprises a shaped body comprising a zeolite, a binder and a hydrogenation metal deposited on the shaped body,
wherein the amount of the hydrogenation metal is 0.035-0.080 wt % with respect to the total catalyst,
wherein the zeolite is ZSM-5 having a silica to alumina molar ratio of 25-75,
wherein the hydrogenation metal is platinum, and
wherein the hydrocracking catalyst comprises less than 0.01 parts tin, less than 0.02 parts lead, less than 0.01 parts bismuth and less than 0.01 parts molybdenum on the basis of 100 parts by weight of the total catalyst.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the zeolite has a silica to alumina molar ratio of 30-65.

### Claim 3 (depends on 2)

The process according to claim 2, wherein the silica to alumina molar ratio is 35-60.

### Claim 4 (depends on 3)

The process according to claim 3, wherein the silica to alumina molar ratio is 40-55.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the hydrocracking feed stream comprises a fresh feed stream which is first stage or multi-stage hydro-treated pyrolysis gasoline, straight run naphtha, hydrocracked gasoline, light coker naphtha and coke oven light oil, FCC gasoline, reformate or mixtures thereof.

### Claim 6 (depends on 5)

The process according to claim 5, wherein the fresh feed stream has been subjected to hydrogenation, enrichment of mono-aromatic compounds, and/or depentanisation.

### Claim 7 (depends on 5)

The process according to claim 5, wherein the hydrocracking feed stream comprises a stream recycled from the hydrocracking product stream.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the hydrocracking feed stream is provided by a process which does not involve the step of removing benzene.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the hydrocracking feed stream comprises 10-90 wt % of benzene.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the amount of the binder in the hydrocracking catalyst is 10-50 wt % with respect to the total catalyst.

### Claim 11 (depends on 1)

The process according to claim 1, wherein the hydrocracking catalyst is prepared by depositing the hydrogenation metal on the shaped body by impregnation or ion exchange.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the hydrocracking catalyst is an extrudate having an average diameter of 0.1-3 mm.

### Claim 13 (depends on 1)

The process according to claim 1, wherein the step (b) is performed at a Weight Hourly Space Velocity of at least 7 h−1.

### Claim 14 (depends on 1)

The process according to claim 1, wherein the silica to alumina molar ratio is 40-55.

### Claim 15

A process for producing benzene comprising the steps of:
(a) providing a hydrocracking feed stream comprising C5-C12 hydrocarbons,
(b) contacting the hydrocracking feed stream in the presence of hydrogen with a hydrocracking catalyst under process conditions including a temperature of 425-580° C., a pressure of 300-5000 kPa gauge and a Weight Hourly Space Velocity of 3-3010 to produce a hydrocracking product stream comprising BTX, and
(c) separating the BTX from the hydrocracking product stream,
wherein the hydrocracking catalyst comprises a shaped body comprising a zeolite, a binder and a hydrogenation metal deposited on the shaped body,
wherein the amount of the hydrogenation metal is 0.035-0.080 wt % with respect to the total catalyst,
wherein the zeolite is ZSM-5 having a silica to alumina molar ratio of 25-75,
wherein the hydrocracking catalyst comprises less than 0.01 parts molybdenum on the basis of 100 parts by weight of the total catalyst, and
wherein the hydrocracking catalyst comprises less than 0.01 parts tin, less than 0.02 parts lead, and less than 0.01 parts bismuth on the basis of 100 parts by weight of the total catalyst.

### Claim 16 (depends on 15)

The process according to claim 15, wherein the amount of the binder in the hydrocracking catalyst is 10-50 wt % with respect to the total catalyst.

### Claim 17 (depends on 15)

The process according to claim 15, wherein the zeolite has a silica to alumina molar ratio of 40-55.