# US 4,398,052 A · Separation of monoolefins from other monoolefins

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- Number: US 4,398,052 A
- Document ID: US4398052A
- Status: Granted
- Kind: A
- Application number: 06/140,282
- Filed: 1980-04-14
- Granted: 1983-08-09
- Earliest claimed: 1980-04-14
- Assignees: Phillips Petroleum Company
- Inventors: Donald C. Tabler; Marvin M. Johnson
- Web page: https://patentgrep.com/patent/US4398052A

## CPC

- C07C 7/156: with solutions of copper salts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process and apparatus for separating monoolefins from other monoolefins comprising contacting a mixture of different monoolefins with a complexing agent selected from the group consisting of copper (I) salts of sulfonic acids and copper (I) salts of dialkyl phosphates and a suitable hydrocarbon solvent for the complexing agent under such conditions that the monoolefins form different strength complexes with the complexing agent. The different strength of the complexes provides a mechanism by which even closely boiling monoolefin isomers may be separated.

## Claims

### Claim 1

A process for at least partially separating a first monoolefin from admixture with a second monoolefin, wherein said first monoolefin forms a stronger complex than said second monoolefin with a complexing agent selected from the group consisting of copper (I) salts of sulfonic acids and copper (I) salts of dialkyl phosphates, said process comprising the steps of:
contacting the mixture of said first monoolefin and said second monoolefin with said complexing agent and a suitable hydrocarbon solvent for said complexing agent under such conditions that said first monoolefin forms a stronger complex than said second monoolefin with said complexing agent; and
separating said first monoolefin from said second monoolefin based on the relative strengths of the first monoolefin complex and the second monoolefin complex.

### Claim 2 (depends on 1)

A method in accordance with claim 1 wherein said step of separating said first monoolefin from said second monoolefin based on the relative strengths of the first monoolefin complex and the second monoolefin complex comprises:
separating said second monoolefin from said complexing agent and from the mixture which contains the complexed first monoolefin and said suitable hydrocarbon solvent; and
separating said first monoolefin from said complexing agent and said suitable hydrocarbon solvent.

### Claim 3 (depends on 1)

A process in accordance with claim 1 wherein said complexing agent is selected from the group consisting of:
(a) the copper(I) salt of an alkane sulfonic acid having from 4 to 20 carbon atoms per molecule;
(b) the copper(I) salt of an aromatic sulfonic acid including alkylaromatic, hydroxyaromatic and haloaromatic sulfonic acids having from 6 to 22 carbon atoms per molecule;
(c) the copper (I) salt of a petroleum sulfonic acid; and
(d) the copper(I) salt of a dialkyl phosphate having from 1 to 12 carbon atoms per alkyl member.

### Claim 4 (depends on 1)

A process in accordance with claim 1 wherein said complexing agent is copper(I) dodecylbenzene sulfonate.

### Claim 5 (depends on 2)

A process in accordance with claim 2 wherein said second monoolefin is separated from said complexing agent and from the mixture which contains the complexed first monoolefin and said suitable hydrocarbon solvent by contacting the solution which results from the contacting of the mixture of said first monoolefin and said second monoolefin with said suitable hydrocarbon solvent and said complexing agent with an additional quantity of said first monoolefin, said additional quantity of said first monoolefin replacing said second monoolefin in the complexed second monoolefin to thereby separate said second monoolefin from said complexing agent and from the mixture which contains the complexed first monoolefin and said suitable hydrocarbon solvent.

### Claim 6 (depends on 5)

A process in accordance with claim 5 wherein said first monoolefin is separated from said complexing agent and said suitable hydrocarbon solvent by subjecting the mixture which contains the complexed first monoolefin and said suitable hydrocarbon solvent to heat.

### Claim 7 (depends on 1)

A process in accordance with claim 1 wherein said first monoolefin is butene-1 and said second monoolefin is isobutene.

### Claim 8 (depends on 1)

A process in accordance with claim 1 wherein said first monoolefin is cis-butene-2 and said second monoolefin is trans-butene-2.

### Claim 9 (depends on 1)

A process in accordance with claim 1 wherein said first monoolefin is cis-pentene-2 and said second monoolefin is trans-pentene-2.

### Claim 10 (depends on 1)

A process in accordance with claim 1 wherein said suitable hydrocarbon solvent is a paraffinic or aromatic hydrocarbon solvent having from 6 to 15 carbon atoms.

### Claim 11 (depends on 10)

A process in accordance with claim 10 wherein said suitable hydrocarbon solvent is a xylene.