IP Library Granted Patent US 7,345,197
Granted Patent B1
US 7,345,197 · App. 11/810,167 · Granted Mar 18, 2008

Preparation of acetic acid

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Quick Facts
Patent No.
US 7,345,197
App. No.
11/810,167
Granted
Mar 18, 2008
Kind
B1
Abstract

A method for removing aldehyde impurities from acetic acid is disclosed. The method comprises extracting the aldehyde impurities from a methyl iodide solution such as the decanter heavy phase with a polyol. After the aldehyde impurities are removed, the methyl iodide heavy phase can be recycled to the carbonylation.

Claims (22)

1. A method for removing an aldehyde from a methyl iodide solution, said method comprising extracting the aldehyde from the solution with a polyol.

2. The method of claim 1 , wherein the polyol is a glycol.

3. The method of claim 1 , wherein the polyol is glycerol.

4. The method of claim 1 , wherein the aldehyde is acetaldehyde.

5. The method of claim 1 , wherein the methyl iodide solution is a decanter heavy phase from an acetic acid production process.

6. The method of claim 5 , wherein the decanter heavy phase comprises from 60 wt % to 90 wt % of methyl iodide, 1 wt % to 10 wt % of acetic acid, 2 wt % to 15 wt % of methyl acetate, 1 wt % to 10 wt % of an alkane, 0.01 wt % to 1 wt % of water, and 0.1 wt % to 5 wt % of the aldehyde.

7. The method of claim 1 , wherein the methyl iodide solution and the polyol are mixed in a volume ratio within the range of 0.1/1 to 10/1.

8. The method of claim 1 , where the methyl iodide solution and the polyol are mixed in a volume ratio within the range of 0.2/1 to 5/1.

9. A method for removing an aldehyde from acetic acid, said method 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 containing an aldehyde;

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

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

(d) condensing and separating the overhead stream in a decanter into a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide and the aldehyde; and

(e) extracting the aldehyde from the heavy, organic phase with a polyol.

10. The method of claim 9 , wherein the catalyst is a rhodium catalyst.

11. The method of claim 9 , wherein the catalyst stabilizer is triphenylphosphine oxide.

12. The method of claim 9 , wherein the concentration of water in step (a) is within the range of 4 wt % to 10 wt % of the reaction mixture.

13. The method of claim 9 , wherein the aldehyde is acetaldehyde.

14. The method of claim 9 , wherein the polyol is a glycol.

15. The method of claim 9 , wherein the polyol is glycerol.

16. The method of claim 9 , wherein the heavy, organic phase of step (d) comprises from 60 wt % to 90 wt % of methyl iodide, 1 wt % to 10 wt % of acetic acid, 2 wt % to 15 wt % of methyl acetate, 1 wt % to 10 wt % of an alkane, 0.01 wt % to 1 wt % of water, and 0.1 wt % to 5 wt % or less of the aldehyde.

17. The method of claim 9 , which comprises recycling the polyol-extracted heavy, organic phase from step (e) to the reaction of step (a).

Assignments (19)
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: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032123/0799 →
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: 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 →
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 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0856 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0020 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0285 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0705 →
SECURITY AGREEMENT Recorded Oct 30, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 023449/0138 →
SECURITY AGREEMENT Recorded Apr 9, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Reel/Frame 022708/0830 →
SECURITY AGREEMENT Recorded Aug 4, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; BASELL POLYOLEFIN GMBH; LYONDELL CHEMICAL COMPANY; EQUISTAR CHEMICALS, L.P.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021354/0708 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AND PATENT APPLICATIONS Recorded Mar 26, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; EQUISTAR CHEMICALS. LP.; LYONDELL CHEMICAL COMPANY; LYONDELL CHEMICAL TECHNOLOGY, L.P.; LYONDELL PETROCHEMICAL COMPANY; NATIONAL DISTILLERS AND CHEMICAL CORPORATION; OCCIDENTAL CHEMICAL CORPORATION; OLIN CORPORATION; QUANTUM CHEMICAL CORPORATION; BASELL POLYOLEFIN GMBH
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 020704/0562 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2007
From: HALLINAN, NOEL C.; SALISBURY, BRIAN A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 019435/0419 →