# US 2013/0158289 A1 · Production of diacetoxyethylene by direct acetoxylation

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- Number: US 2013/0158289 A1
- Document ID: US20130158289A1
- Status: Published application
- Kind: A1
- Application number: 13/327,401
- Filed: 2011-12-15
- Published: 2013-06-20
- Earliest claimed: 2011-12-15
- Assignees: Celanese International Corporation
- Inventors: Joseph G. Duff; Stephen Kerlegon; Kien V. Phung; Daniel Rangel-Osalde; Tatiana H. Sonnenberg; Cathy L. Tway; Hang Wang
- Web page: https://patentgrep.com/patent/US20130158289A1

## CPC

- C07C 67/05: with oxidation
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

In one embodiment, the invention is to a process for producing a vinyl acetate composition by contacting a vinyl acetate stream with acetic acid, ethylene, and oxygen to form a reaction mixture and reacting the reaction mixture in a reactor under conditions effective to form a crude vinyl acetate composition comprising vinyl acetate, water, acetic acid and at least 0.1 wt % diacetoxyethylene.

## Claims

### Claim 1

A process for producing a vinyl acetate composition, the process comprising the steps of:
(a) contacting a vinyl acetate stream with acetic acid, ethylene, and oxygen to form a reaction mixture; and
(b) reacting the reaction mixture in a reactor under conditions effective to form a crude vinyl acetate composition comprising vinyl acetate, water, acetic acid and at least 0.1 wt % diacetoxyethylenes.

### Claim 2 (depends on 1)

The process of claim 1, wherein a ratio of vinyl acetate to acetic acid in the reaction mixture is at least 1:3.

### Claim 3 (depends on 1)

The process of claim 1, wherein the reaction in step (b) has an ethylene conversion less than 5%.

### Claim 4 (depends on 1)

The process of claim 1, further comprising the step of:
(c) separating the crude vinyl acetate composition to form a purified vinyl acetate stream comprising vinyl acetate and a by-product stream comprising diacetoxyethylene.

### Claim 5 (depends on 4)

The process of claim 4, further comprising the step of:
(d) directing at least a portion of the purified vinyl acetate stream to the reactor.

### Claim 6 (depends on 1)

The process of claim 1, wherein the vinyl acetate stream comprises at least a portion of a purified vinyl acetate stream.

### Claim 7 (depends on 4)

The process of claim 4, wherein step (c) is performed via at least one distillation column.

### Claim 8 (depends on 1)

The process of claim 1, wherein the diacetoxyethylene in the crude vinyl acetate composition comprises an isomeric mixture comprising cis-diacetoxyethylene and trans-diacetoxyethylene.

### Claim 9 (depends on 8)

The process of claim 8, wherein the diacetoxyethylene in the crude vinyl acetate composition comprises at least about 0.025 wt % cis-diacetoxyethylene, and at least about 0.075 wt % trans-diacetoxyethylene.

### Claim 10 (depends on 8)

The process of claim 8, wherein the ratio of cis-/trans-diacetoxyethylene in the crude vinyl acetate composition comprises from about 1:3 to about 1:1.

### Claim 11 (depends on 8)

The process of claim 8, wherein the concentration of mixed diacetoxyethylenes in the crude vinyl acetate stream comprises between about 0.3 and 1 wt %.

### Claim 12 (depends on 8)

The process of claim 8, wherein the concentration of mixed diacetoxyethylenes in the crude vinyl acetate stream comprises at least 0.5 wt %.

### Claim 13

A vinyl acetate composition comprising vinyl acetate and at least 0.1 wt % diacetoxyethylene.

### Claim 14 (depends on 13)

The vinyl acetate composition of claim 13, wherein the diacetoxyethylene in the crude vinyl acetate composition comprises an isomeric mixture comprising cis-diacetoxyethylene and trans-diacetoxyethylene.

### Claim 15 (depends on 14)

The vinyl acetate composition of claim 14, which comprises at least about 0.025 wt % cis-diacetoxyethylene, and at least about 0.075 wt % trans-diacetoxyethylene.

### Claim 16 (depends on 14)

The vinyl acetate composition of claim 14, wherein the ratio of cis-/trans-diacetoxyethylene in the crude vinyl acetate composition comprises from about 1:3 to about 1:1.

### Claim 17 (depends on 14)

The vinyl acetate composition of claim 14, wherein the concentration of mixed diacetoxyethylenes in the crude vinyl acetate stream comprises between about 0.3 and 1 wt %.

### Claim 18 (depends on 17)

The vinyl acetate composition of claim 17, wherein the concentration of mixed diacetoxyethylenes in the crude vinyl acetate stream comprises at least 0.5 wt %.