IP Library Granted Patent US 7,390,919
Granted Patent B1
US 7,390,919 · App. 11/906,313 · Granted Jun 24, 2008

Methyl acetate purification and carbonylation

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Quick Facts
Patent No.
US 7,390,919
App. No.
11/906,313
Granted
Jun 24, 2008
Kind
B1
Abstract

Disclosed is a method for removing aldehyde impurities from a methyl acetate supply. The method comprises reacting the methyl acetate supply with a polyol and converting the aldehyde impurities to cyclic acetals. The acetals are subsequently removed from the methyl acetate supply by, e.g., distillation. The purified methyl acetate supply is used for carbonylation to produce acetic acid.

Claims (16)

1. A method for removing an aldehyde impurity from a methyl acetate supply, said method comprising reacting the supply with a polyol to convert the aldehyde to a cyclic acetal, and isolating the acetal from the methyl acetate supply.

2. The method of claim 1 , wherein the polyol is a C 2 -C 10 diol or triol.

3. The method of claim 1 , wherein the polyol is selected from the group consisting of ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, cyclohexane-1,4-dimethanol, glycerin and mixtures thereof.

4. The method of claim 1 , wherein the polyol is selected from the group consisting of 1,3-propanediol, 2-methyl-1,3-propanediol, and glycerin.

5. The method of claim 1 , wherein the methyl acetate supply is a mixture of methyl acetate and methanol.

6. The method of claim 1 , wherein the aldehyde impurity comprises acetaldehyde.

7. The method of claim 6 , wherein the methyl acetate supply contains from about 50 ppm to about 50,000 ppm acetaldehyde.

8. The method of claim 7 , wherein the methyl acetate supply contains from about 50 ppm to about 1000 ppm acetaldehyde.

9. The method of claim 1 , wherein the reaction is performed in the presence of an acidic catalyst.

10. The method of claim 9 , wherein the catalyst is an ion exchange resin.

11. The method of claim 1 , wherein the acetal is isolated from the methyl acetate supply by distillation.

12. A methanol carbonylation process comprising carbonylating methanol in the presence of a carbonylation catalyst, a catalyst stabilizer, and a methyl acetate supply purified by the method of claim 1 .

13. The process of claim 12 , wherein the carbonylation catalyst is selected from the group consisting of rhodium catalysts and iridium catalysts.

14. The process of claim 12 , wherein the catalyst stabilizer is a phosphine oxide.

15. The method of claim 12 , wherein the catalyst stabilizer is triphenylphosphine oxide.

16. The method of claim 12 , wherein the catalyst stabilizer is lithium iodide.

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 Nov 7, 2007
From: SALISBURY, BRIAN A.; HANES, RONNIE M.; HALLINAN, NOEL C.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 020089/0731 →