# US 2013/0158288 A1 · Process For Producing Acrylic Acids and Acrylates

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- Number: US 2013/0158288 A1
- Document ID: US20130158288A1
- Status: Published application
- Kind: A1
- Application number: 13/327,888
- Filed: 2011-12-16
- Published: 2013-06-20
- Earliest claimed: 2011-12-16
- Assignees: Celanese International Corporation
- Inventors: Craig J. Peterson; R. Jay Warner; Josefina T. Chapman
- Web page: https://patentgrep.com/patent/US20130158288A1

## CPC

- C07C 51/42: Separation; Purification; Stabilisation; Use of additives
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

In one embodiment, the invention is to process for producing acrylics. The process includes the steps of contacting a crude product stream with an extraction agent mixture at a temperature less than 50° C.

## Claims

### Claim 1

A process for producing an acrylate product, the process comprising the steps of:
(a) providing a crude product stream comprising acrylate product, alkylenating agent and water;
(b) contacting a portion of the crude product stream or a derivative stream thereof with at least one extraction agent to form an extract stream comprising acrylate product and extraction agent and a raffinate stream comprising alkylenating agent and water, wherein step (b) is carried out at a temperature less than 50° C.; and
(c) recovering acrylate product.

### Claim 2 (depends on 1)

The process of claim 1, wherein the extract stream comprises less than 10 wt. % alkylenating agent.

### Claim 3 (depends on 1)

The process of claim 1, wherein the extract stream comprises at least 1 wt. % acrylate product.

### Claim 4 (depends on 1)

The process of claim 1, wherein the extract stream comprises at least 10 wt. % acrylate product.

### Claim 5 (depends on 1)

The process of claim 1, wherein the extract stream comprises at least 1 wt. % acetic acid.

### Claim 6 (depends on 1)

The process of claim 1, wherein the extract stream comprises at least 2 wt. % acrylate product and acetic acid combined.

### Claim 7 (depends on 1)

The process of claim 1, wherein the extract stream comprises at least 20 wt. % acrylate product and acetic acid combined.

### Claim 8 (depends on 1)

The process of claim 1, wherein the extract stream comprises less than 7 wt. % water.

### Claim 9 (depends on 1)

The process of claim 1, wherein the extraction selectivity to acrylate product is at least 10%.

### Claim 10 (depends on 1)

The process of claim 1, wherein the acrylate product in the extract stream comprises at least 50% of the acrylate in the crude product stream.

### Claim 11 (depends on 1)

The process of claim 1, wherein the alkylenating agent in the extract stream comprises less than 50% of the alkylenating agent in the crude product stream.

### Claim 12 (depends on 1)

The process of claim 1, wherein the at least one extraction agent has a higher selectivity to acrylate product than the alkylenating agent.

### Claim 13 (depends on 1)

The process of claim 1, wherein the at least one extraction agent has a higher selectivity to acrylate product than acetic acid.

### Claim 14 (depends on 1)

The process of claim 1, wherein the raffinate stream comprises at least 1 wt. % alkylenating agent.

### Claim 15 (depends on 1)

The process of claim 1, wherein the raffinate stream comprises at least 10 wt. % alkylenating agent.

### Claim 16 (depends on 1)

The process of claim 1, wherein the raffinate stream comprises no more than 10 wt. % acrylate.

### Claim 17 (depends on 1)

The process of claim 1, wherein the raffinate stream comprises no more than 50 wt. % acetic acid.

### Claim 18 (depends on 1)

The process of claim 1, wherein the raffinate stream comprises no more than 60 wt. % acrylate product and acetic acid combined.

### Claim 19 (depends on 1)

The process of claim 1, wherein the acrylate product in the raffinate stream is no more than 50% of the acrylate product in the crude product stream.

### Claim 20 (depends on 1)

The process of claim 1, wherein the alkylenating agent in the raffinate stream at least 50% of the alkylenating agent in the crude product stream.

### Claim 21 (depends on 1)

The process of claim 1, wherein the alkylenating agent comprises formaldehyde.

### Claim 22 (depends on 1)

The process of claim 1, wherein the at least one extraction agent is selected from the group consisting of cyclohexane, toluene, isopropyl acetate, o-xylene, p-xylene, m-xylene, butyl acetate, butanol, methyl acetate, methyl acrylate, diphenyl ether, ethyl acrylate, isopropyl acetate, ethyl propionate, hexane, benzene, diisopropyl ether, n,n-dimethyl aniline, dibutyl ether, tetralin, butyl acrylate, 2-ethylhexyl alcohol, isophorone, ditolyl ether, dimethyl phthalate, 3,3 trimethyl-cyclohexanone, biphenyl, o-dichlorobenzene, and a mixture thereof.

### Claim 23 (depends on 1)

The process of claim 1, wherein the at least one extraction agent comprises diisobutyl ketone.

### Claim 24 (depends on 1)

The process of claim 1, wherein the relativity volatility of the at least one extraction agent to acrylate product is less than 1.

### Claim 25 (depends on 1)

The process of claim 1, wherein the mass ratio of acrylate product to alkylating agent in the extract stream is greater than 5:1.

### Claim 26 (depends on 1)

The process of claim 1, further comprising the step of separating at least a portion of the raffinate stream to form an alkylating agent stream and a first solvent stream comprising at least a portion of the at least one extraction agent.

### Claim 27 (depends on 26)

The process of claim 26, wherein step (b) is conducted in an extraction unit and wherein the first solvent stream is recycled to the extraction unit.

### Claim 28 (depends on 1)

The process of claim 1, further comprising the step of separating the extract stream to form a purified acrylic acid stream and a second solvent stream, comprising at least a portion of the at least one extraction agent.

### Claim 29 (depends on 28)

The process of claim 28, wherein step (b) is conducted in an extraction unit and wherein the second solvent stream is recycled to the extraction unit.

### Claim 30

A process for producing an acrylate product, the process comprising the steps of:
(a) providing a crude product stream comprising acrylate product, alkylenating agent, and water;
(b) contacting the crude product stream with an extraction agent stream comprising at least one extraction agent, wherein step (c) is conducted at a temperature less than 50° C.; and
(c) removing alkylenating agent from the crude product stream.
