# US 4,393,249 A · Process for removing alkynes from C.sub.4 hydrocarbon mixtures

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- Number: US 4,393,249 A
- Document ID: US4393249A
- Status: Granted
- Kind: A
- Application number: 06/314,288
- Filed: 1981-10-23
- Granted: 1983-07-12
- Earliest claimed: 1981-10-23
- Assignees: The Dow Chemical Company
- Inventors: Albert Heuvelsland; Fritz F. F. Jann; Greet de Block-Martens
- Web page: https://patentgrep.com/patent/US4393249A

## CPC

- C07C 41/08: to carbon-to-carbon triple bonds
- C07C 7/14891: {alcohols}
- C07C 41/06: by addition of organic compounds only
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for removing alkynes from hydrocarbon mixtures, particularly those containing butadiene by reacting the alkynes with hydroxyl group containing organic compounds in the presence of a silver exchanged ion-exchange resin and separating the products formed from the unreacted components of said mixture.

## Claims

### Claim 1

A process comprising contacting an alkyne with a C.sub.1 -C.sub.4 monohydric alcohol or mixture thereof under reaction conditions to form an ether, said reactive process occurring in the presence of a catalytic amount of a cation-exchange resin having a plurality of pendant sulfonate groups with silver metal counterions.

### Claim 2 (depends on 1)

A process as defined in claim 1 wherein said polymeric material is a styrene-divinylbenzene copolymer resin.

### Claim 3 (depends on 2)

A process as defined in claim 2 wherein said alcohol is methanol.

### Claim 4

A process for etherifying alkynes comprising contacting under conversion conditions an alkyne or mixture thereof with an organic compound containing at least one hydroxyl group in the presence of ion-exchange resin containing silver ions.

### Claim 5

A process for the removal of alkynes from inorganic or organic mixtures or combination mixtures thereof comprising contacting under reaction conditions said alkyne-containing mixture with an organic compound having at least one hydroxyl group in the presence of a catalytic amount of a silver exchanged ion-exchange resin and thereafter removing the oxygen-containing products from said mixture.

### Claim 6

A process for the removal of alkynes from fluid streams comprising contacting a fluid stream containing a plurality of alkynes with water, or an organic compound having at least one hydroxyl group or mixture thereof under conditions sufficient to convert said alkynes to oxygen-containing products and removing from the reaction mixture the products so formed, said reactive process occurring in the presence of a catalytic amount of a polymeric material having associated therewith silver ions.

### Claim 7 (depends on 6)

A process as defined in claim 6 wherein said fluid stream is a hydrocarbon stream.

### Claim 8 (depends on 7)

A process as defined in claim 7 wherein said hydroxyl compound is water or an organic compound having at least one hydroxyl group, said hydroxyl compound being of the formula R--OH wherein R is alkyl, acyl, aryl, cycloalkyl or combinations thereof or hydrogen.

### Claim 9 (depends on 8)

A process as defined in claim 8 wherein said hydroxyl compound is a C.sub.1 -C.sub.4 monohydric alcohol.

### Claim 10 (depends on 9)

A process as defined in claim 9 wherein said hydrocarbon stream is a C.sub.4 hydrocarbon stream.

### Claim 11 (depends on 10)

A process as defined in claim 10 wherein said alcohol is methanol.

### Claim 12 (depends on 10)

A process as defined in claim 10 wherein said oxygen-containing products are ethers.

### Claim 13 (depends on 12)

A process as defined in claim 12 wherein said polymeric material is a cation-exchange resin having a plurality of pendant sulfonate groups with silver metal counterions.

### Claim 14 (depends on 13)

A process as defined in claim 13 wherein said polymeric material is a styrene-divinylbenzene copolymer resin.

### Claim 15 (depends on 1)

The process of claim 1 wherein the reaction conditions include a temperature less than about 90.degree. C.

### Claim 16 (depends on 5)

The process of claim 5 wherein the reaction conditions include a temperature less than about 90.degree. C.

### Claim 17 (depends on 16)

The process of claim 16 wherein the reaction conditions include a temperature of from about 30.degree. C. to about 90.degree. C.

### Claim 18 (depends on 17)

The process of claim 17 wherein the reaction conditions include a temperature of from about 60.degree. C. to about 80.degree. C.

### Claim 19 (depends on 6)

The process of claim 6 wherein the conditions include a temperature of less than about 90.degree. C.

### Claim 20 (depends on 19)

The process of claim 19 wherein the conditions include a temperature from about 30.degree. C. to about 90.degree. C.

### Claim 21 (depends on 20)

The process of claim 20 wherein the conditions include a temperature from about 60.degree. C. to about 80.degree. C.