# US 10,118,874 B2 · Process for producing benzene from a C5-C12 hydrocarbon mixture

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- Number: US 10,118,874 B2
- Document ID: US10118874B2
- Status: Granted
- Kind: B2
- Application number: 15/318,136
- Filed: 2015-06-01
- Published: 2017-05-11
- Granted: 2018-11-06
- Earliest claimed: 2014-06-13
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Andrew Davies; Dustin Fickel; Maikel Van Iersel
- Web page: https://patentgrep.com/patent/US10118874B2

## CPC

- C07C 4/06: Catalytic processes {(C07C4/025 takes precedence)}
- B01J 21/04: Alumina
- B01J 23/42: Platinum
- B01J 29/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J 29/44: Noble metals
- B01J 35/19: {Catalysts containing parts with different compositions}
- B01J 37/04: Mixing {(B01J37/0009, B01J37/0018 take 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 47/00: Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions (C10G15/00 takes precedence; destructive hydrogenation of non-melting solid carbonaceous or similar materials C10G1/06)
- C10G 47/14: the catalyst containing platinum group metals or compounds thereof
- C10G 47/18: the catalyst containing platinum group metals or compounds thereof
- C10G 63/00: Treatment of naphtha by at least one reforming process and at least one other conversion process (C10G59/00, C10G61/00 take precedence)
- C10G 63/08: including at least one cracking step
- C07C 2529/44: Noble metals
- C10G 2300/1044: Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
- C10G 2300/301: Boiling range
- C10G 2300/4056: Retrofitting operations
- C10G 2300/4081: Recycling aspects
- C10G 2300/708: Coking aspect, coke content and composition of deposits
- 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 comprising 0.01-1 wt-% hydrogenation metal in relation to the total catalyst weight and a zeolite having a pore size of 5-8 A and a silica (SiO2) to alumina (Al2O3) molar ratio of 5-200 under process conditions including a temperature of 425-580° C., a pressure of 300-5000 kPa gauge and a Weight Hourly Space Velocity of 0.1-15 h−1 to produce a hydrocracking product stream comprising benzene, toluene and C8+ hydrocarbons, (c) separating benzene, toluene and the C8+ hydrocarbons from the hydrocracking product stream and (d) selectively recycling back at least part of the toluene from the separated products of step (c) to be included in the hydrocracking feed stream process for producing benzene from a c5-c12 hydrocarbon mixture

## 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 comprising 0.01-1 wt-% hydrogenation metal in relation to the total catalyst weight and a zeolite having a pore size of 5-8 Å and a silica (SiO2) to alumina (Al2O3) molar ratio of 5-200 under process conditions including a temperature of 425-580° C., a pressure of 300-5000 kPa gauge and a Weight Hourly Space Velocity of 0.1-15 h−1 to produce a hydrocracking product stream comprising benzene, toluene and C8+ hydrocarbons,
(c) separating benzene, toluene and the C8+ hydrocarbons from the hydrocracking product stream, and
(d) selectively recycling at least part of the toluene from the separated products of step (c) to the hydrocracking feed stream,
wherein the amount of toluene to be recycled to the hydrocracking feed stream is set so that the ratio of [molar amount of benzene+molar amount of ethylbenzene]*[molar amount of xylene] divided by [molar amount of toluene]2 in the hydrocracking feed stream is 0.05 to 0.15.

### Claim 2 (depends on 1)

The process according to claim 1, wherein step (a) involves mixing a fresh feed stream and the recycled toluene, wherein the fresh feed stream comprises at least 10 wt % benzene.

### Claim 3 (depends on 2)

The process according to claim 2, wherein the fresh feed stream is pyrolysis gasoline, straight run naphtha, light coker naphtha, coke oven light oil or mixtures thereof, optionally after being hydrogenated in a hydrogenation reactor.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the hydrocracking feed stream has not been subjected to the step of removing benzene.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the hydrocracking feed stream comprises at least 1 wt % benzene.

### Claim 6 (depends on 1)

The process according to claim 1, 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 7 (depends on 1)

The process according to claim 1, wherein the amount of toluene to be recycled back to the hydrocracking feed stream is set so that the proportion of benzene in the hydrocracking product stream is 0-5 mol % higher than the proportion of benzene in the hydrocracking feed stream.

### Claim 8 (depends on 1)

The process according to claim 1, wherein xylene is separated from the hydrocracking product stream.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the zeolite is a ZSM-5 zeolite.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the hydrogenation metal is platinum.

### Claim 11 (depends on 1)

The process according to claim 1, wherein the hydrocracking catalyst comprises the hydrogenation metal on a zeolite-based support.

### Claim 12 (depends on 2)

The process according to claim 2, wherein the fresh feed stream comprises at least 20 wt % benzene.

### Claim 13 (depends on 12)

The process according to claim 12, wherein the fresh stream comprises at least 30 wt % benzene.