# US 5,347,067 A · Alkylation catalyst regeneration

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

- Number: US 5,347,067 A
- Document ID: US5347067A
- Status: Granted
- Kind: A
- Application number: 08/119,861
- Filed: 1993-08-24
- Granted: 1994-09-13
- Earliest claimed: 1992-06-26
- Assignees: Phillips Petroleum Company
- Inventors: Alan D. Eastman; Ronald G. Abbott
- Web page: https://patentgrep.com/patent/US5347067A

## CPC

- B01J 31/0222: {comprising sulfonyl groups}
- B01J 31/4092: {involving a stripping step, with stripping gas or solvent}
- B01J 38/50: using organic liquids
- C07C 2/62: with acids
- B01J 21/08: Silica
- B01J 21/18: Carbon
- B01J 27/12: Fluorides
- B01J 2231/4205: C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- C07C 2527/1206: Hydrogen fluoride
- Y02P 20/584: Recycling of catalysts
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Described is a novel acid-soluble oil composition produced as a by-product from an alkylation reaction catalyzed by a sulfone-containing catalyst. Also described is a novel process for regenerating an alkylation catalyst which contains a sulfone component. The regeneration process utilizes alumina adsorbent to remove a substantial portion of the hydrogen halide from the spent catalyst, thereby producing a neutralized stream, which is then treated with carbon to remove a substantial portion of the reaction by-product to produce a sulfone stream substantially free of reaction by-product and hydrogen halide.

## Claims

### Claim 1

An alkylation process, comprising the steps of:
(a) contacting a hydrocarbon mixture, comprising olefins and isoparaffins, with a catalyst mixture, comprising sulfolane and HF, within a reaction zone to thereby produce a reaction product and a reaction by-product;
(b) separating said reaction product from said catalyst mixture within a first separation zone to produce a separated reaction product and a separated catalyst mixture with said separated catalyst mixture containing a substantial amount of said reaction by-product;
(c) utilizing said separated catalyst mixture as at least a portion of said catalyst mixture;
(d) passing a portion of said separated catalyst mixture to a second separation zone to thereby separate said a portion of said separated catalyst mixture into a second separation zone overhead stream, comprising a major portion of the HF component of said a portion of said separated catalyst mixture, and a second separation zone bottoms stream comprising a major portion of the sulfolane component of said a portion of said separated catalyst mixture and a major portion of the reaction by-product component of said a portion of said separated catalyst mixture;
(e) utilizing said second separation zone overhead stream as at least a portion of the HF component of said catalyst mixture;
(f) contacting said second separation zone bottoms stream with alumina to thereby remove a substantial portion of the HF contained in said second separation zone bottoms stream to produce a neutralized second separation zone bottoms stream;
(g) contacting said neutralized second separation zone bottoms stream with carbon to thereby remove a substantial portion of said major portion of the reaction by-product to produce a sulfolane stream substantially free of said reaction by-product and HF; and
(h) utilizing said sulfolane stream as at least a portion of the sulfolane component of said catalyst mixture.

### Claim 2

An alkylation process comprising the steps of:
(a) contacting a hydrocarbon mixture, comprising olefins and isoparaffins, with a catalyst mixture, comprising a sulfone component and a hydrogen halide component, within a reaction zone to thereby produce a reaction product and a reaction by-product;
(b) separating said reaction product from said catalyst mixture within a first separation zone to produce a separated reaction product and a separated catalyst mixture with said separated catalyst mixture containing a substantial amount of said reaction by-product;
(c) passing said separated catalyst mixture to a second separation zone to thereby separate said separated catalyst mixture into a second separation zone overhead stream, comprising a major portion of the hydrogen halide component of said separated catalyst mixture, and a second separation zone bottoms stream, comprising a major portion of the sulfone component of said separated catalyst mixture and a major portion of the reaction by-product component of said separated catalyst mixture;
(d) contacting said second separation zone bottoms stream with alumina to thereby remove a substantial portion of the hydrogen halide contained in said second separation zone bottoms stream to produce a neutralized second separation zone bottoms stream; and
(e) contacting said neutralized second separation zone bottoms stream with carbon to thereby remove a substantial portion of said major portion of the reaction by-product to produce a sulfone stream substantially free of said reaction by-product and said hydrogen halide component.

### Claim 3 (depends on 1)

A process as recited in claim 1, further comprising: utilizing said separated catalyst mixture as at least a portion of said catalyst mixture.

### Claim 4 (depends on 2)

A process as recited in claim 2, further comprising: utilizing said second separation zone overhead stream as a portion of the hydrogen halide component of said catalyst mixture.

### Claim 5 (depends on 3)

A process as recited in claim 3, further comprising: utilizing said sulfone stream as at least a portion of the sulfone component of said catalyst mixture.

### Claim 6 (depends on 5)

A process as recited in claim 5, wherein the sulfone component of said catalyst mixture is sulfolane and the hydrogen halide component of said catalyst mixture is hydrogen fluoride.

### Claim 7 (depends on 6)

A process as recited in claim 6, wherein said reaction by-product comprises acid soluble oil.

### Claim 8 (depends on 7)

A process as recited in claim 7, wherein the weight ratio of hydrogen halide to sulfone in said catalyst mixture is in the range of from about 1:1 to about 40:1 wherein the acid soluble oil in said catalyst mixture is present in an amount no more than about 20 weight percent of said catalyst mixture.

### Claim 9 (depends on 8)

A process as recited in claim 8, wherein said sulfone stream contains acid soluble oil at a concentration less than about 2 weight percent of the total weight of the sulfone component.

### Claim 10 (depends on 1, 9)

A process as recited in claim 9, wherein the contact pressure of contacting steps (d) and (e) of claim 1 is in the range of from 0.5 atmospheres of absolute pressure to about 30 atmospheres of absolute pressure and the contact temperature of contacting steps (d) and (e) of claim 1 is in the range of from O.degree. F. to about 400.degree. F.