IP Library Granted Patent US 7,790,919
Granted Patent B2
US 7,790,919 · App. 12/077,098 · Granted Sep 7, 2010

Removing hydrocarbon impurities from acetic acid production process

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,790,919
App. No.
12/077,098
Granted
Sep 7, 2010
Kind
B2
Abstract

A method for removing hydrocarbon impurities from an acetic acid production process is disclosed. The method comprises distilling at least a portion of the heavy organic phase from the decanter of the acetic acid production process into a vapor stream comprising the majority of methyl iodide (i.e., over 50% of the methyl iodide from the heavy organic phase) and a bottoms stream comprising the majority of acetic acid, methyl acetate, methyl iodide and the hydrocarbon impurity (i.e., over 50% of each of the components from the heavy organic phase); extracting the bottoms stream with water, an acetic acid aqueous solution, or with a methanol aqueous solution to form an organic phase comprising the majority of the hydrocarbon impurity (over 50% of the hydrocarbon impurity from the bottom stream) and an aqueous phase comprising the majority of methyl iodide (over 50% of the methyl iodide from the bottoms stream); and recycling the aqueous phase to the carbonylation reaction.

Claims (22)

1. A method for removing a hydrocarbon impurity from an acetic acid production process, 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 a hydrocarbon impurity;

(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 hydrocarbon impurity, and a liquid stream comprising the catalyst and the catalyst stabilizer;

(c) separating the vapor stream from step (b) by distillation into a product stream comprising acetic acid and a minor amount of water, and an overhead stream comprising methyl iodide, water, methyl acetate, acetic acid and the hydrocarbon impurity;

(d) condensing and separating the overhead stream from step (c) into a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide, acetic acid, methyl acetate, and the hydrocarbon impurity; and

(e) distilling at least a portion of the heavy, organic phase from step (d) into a vapor stream comprising the majority of methyl iodide and a bottoms stream comprising the majority of acetic acid, methyl acetate, methyl iodide, and the hydrocarbon impurity;

(f) extracting the bottoms stream from step (e) with water, an acetic acid aqueous solution, or with a methanol aqueous solution, and forming an organic phase comprising the majority of the hydrocarbon impurity and an aqueous phase comprising the majority of water, acetic acid, methyl iodide, and optional methanol; and

(g) recycling the aqueous phase from step (f) to the carbonylation reaction of step (a).

2. The method of claim 1 , wherein the catalyst is a rhodium catalyst.

3. The method of claim 1 , wherein the catalyst stabilizer is triphenylphosphine oxide.

4. The method of claim 1 , wherein the concentration of water in step (a) is within the range of about 2 wt % to about 10 wt % of the reaction mixture.

5. The method of claim 1 , wherein the hydrocarbon impurity is selected from the group consisting of alkanes, alkenes, aromatics, and mixtures thereof.

6. The method of claim 1 , wherein the heavy, organic phase of step (d) comprises from about 60 wt % to about 90 wt % of methyl iodide, about 1 wt % to about 10 wt % of acetic acid, about 2 wt % to about 15 wt % of methyl acetate, about 1 wt % to about 10 wt % of the hydrocarbon impurity, and about 0.01 wt % to about 1 wt % of water.

7. The method of claim 1 , the distillation of step (e) is conducted at an overhead temperature less than 75° C.

8. The method of claim 1 , wherein the distillation of step (e) is conducted at an overhead temperature within the range of about 43° C. to about 75° C.

9. The method of claim 1 , wherein the distillation of step (e) is conducted at an overhead temperature within the range of about 43° C. to about 60° C.

10. The method of claim 1 , wherein the distillation of step (e) is conducted at an overhead temperature within the range of about 43° C. to about 45° C.

11. A method for separating methyl iodide and hydrocarbon, said method comprising extracting a mixture comprising methyl iodide and a hydrocarbon with an extracting solution selected from the group consisting of water, acetic acid aqueous solutions, and ethanol aqueous solutions, and forming an organic phase comprising the hydrocarbon and an aqueous phase comprising methyl iodide, wherein the hydrocarbon is selected from the group consisting of alkanes, alkene, aromatics, and mixtures thereof.

12. The method of claim 11 , wherein the hydrocarbon is a C3-C12 alkane or a mixture thereof.

13. The method of claim 11 , wherein the extracting solution is an acetic acid aqueous solution.

14. The method of claim 11 , wherein the extracting solution is a methanol aqueous solution.

15. The method of claim 11 , wherein the aqueous phase is introduced to a methanol carbonylation reaction.

Assignments (16)
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 →
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, LP
Reel/Frame 024337/0020 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2008
From: HALLINAN, NOEL C.; SALISBURY, BRIAN A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 020813/0991 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2008
From: HALLINAN, NOEL C.; SALISBURY, BRIAN A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 020717/0273 →