IP Library Granted Patent US 8,519,181
Granted Patent B2
US 8,519,181 · App. 12/798,598 · Granted Aug 27, 2013

Preparation of acetic acid

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Quick Facts
Patent No.
US 8,519,181
App. No.
12/798,598
Granted
Aug 27, 2013
Kind
B2
Abstract

The disclosure relates to a process for the preparation of acetic acid. The process comprises reacting a decanter heavy, organic phase of an acetic acid production process with acetic anhydride to convert acetaldehyde in the decanter heavy, organic phase to ethylidene diacetate and separating it from the decanter heavy, organic phase. Ethylidene diacetate can be hydrolyzed to recover acetic acid.

Claims (19)

1. A process comprising reacting a stream of an acetic acid production process, which comprises methyl iodide and acetaldehyde, with acetic anhydride in the presence of an acid catalyst comprising an ion exchange resin to convert acetaldehyde to ethylidene diacetate, and separating the ethylidene diacetate from the stream.

2. The process of claim 1 , wherein the stream of the acetic acid production process is a decanter heavy, organic phase.

3. The process of claim 2 , wherein the separation of the ethylidene diacetate from the decanter heavy, organic phase is by distillation.

4. The process of claim 3 , comprising hydrolyzing the separated ethylidene diacetate to recover acetic acid.

5. A process for producing acetic acid, said process comprising:

(a) reacting methanol and carbon monoxide in the presence of a carbonylation catalyst, a catalyst stabilizer, methyl iodide, water and methyl acetate to produce an acetic acid stream comprising the catalyst, the catalyst stabilizer, methyl iodide, methyl acetate, water, acetic acid, and acetaldehyde;

(b) flashing at least a portion of the acetic acid stream to produce a vapor stream comprising acetic acid, water, methyl acetate, methyl iodide and acetaldehyde, and a liquid stream comprising the catalyst and the catalyst stabilizer;

(c) separating the vapor stream by distillation into an acetic acid product stream comprising acetic acid and water, and an overhead stream comprising methyl iodide, water, methyl acetate, acetic acid, and acetaldehyde;

(d) condensing the overhead stream to produce a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide and acetaldehyde;

(e) reacting at least a portion of the heavy, organic phase with acetic anhydride in the presence of an acid catalyst comprising an ion exchange resin to convert acetaldehyde to ethylidene diacetate; and

(f) separating the ethylidene diacetate from the heavy, organic phase by distillation.

6. The process of claim 5 , comprising hydrolyzing the ethylidene diacetate to recover acetic acid.

7. The process of claim 6 , comprising recycling the recovered acetic acid to step (d).

8. The process of claim 5 , wherein the carbonylation catalyst is a rhodium catalyst.

9. The process of claim 5 , wherein the catalyst stabilizer is selected from the group consisting of pentavalent Group VA oxides, metal iodide salts, and mixtures thereof.

10. The process of claim 9 , wherein the catalyst stabilizer is a phosphine oxide.

11. The process of claim 10 , wherein the catalyst stabilizer is triphenylphosphine oxide.

12. The process of claim 5 , wherein the water concentration of step (a) is 6wt % or less based on the total weight of the acetic acid stream.

13. The process of claim 5 , wherein step (e) occurs at a temperature of from about 20° C. to about 50° C.

Assignments (11)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2014
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: LYONDELLBASELL ACETYLS, LLC
Reel/Frame 033182/0019 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: CITIBANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032125/0296 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032137/0156 →
APPOINTMENT OF SUCCESSOR ADMINISTRATIVE AGENT Recorded Jan 23, 2014
From: UBS AG, STAMFORD BRANCH
To: BANK OF AMERICA, N.A.
Reel/Frame 032137/0639 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: BANK OF AMERICA, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032138/0134 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032123/0799 →
SECURITY AGREEMENT Recorded May 19, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 024402/0681 →
SECURITY AGREEMENT Recorded May 18, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024397/0818 →
SECURITY AGREEMENT Recorded May 7, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 024342/0801 →
SECURITY AGREEMENT Recorded May 6, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 024342/0421 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2010
From: SALISBURY, BRIAN A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 024235/0702 →