IP Library Granted Patent US 8,927,762
Granted Patent B2
US 8,927,762 · App. 13/669,543 · Granted Jan 6, 2015

Production of oxygenated compounds from carbon monoxide and dimethyl carbonate

Inventors: Stephane Marie-Rose (Sherbrooke, CA); Esteban Chornet (Sherbrooke, CA)
Assignee: Enerkem, Inc.
C07C67/36C07C41/01C07C45/49
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Quick Facts
Patent No.
US 8,927,762
App. No.
13/669,543
Granted
Jan 6, 2015
Kind
B2
Abstract

A method of producing at least one oxygenated compound, such as methyl acetate, dimethyl ether, and formaldehyde, by reacting dimethyl carbonate and carbon monoxide in the presence of a faujasite zeolite, zeolite Beta, Linde Type L (LTL) zeolite, or MCM-41 zeolite.

Claims (22)

1. A method of producing at least one oxygenated compound selected from the group consisting of methyl acetate, dimethyl ether, formaldehyde, and mixtures thereof, comprising:

reacting dimethyl carbonate with carbon monoxide under conditions which convert at least a portion of said dimethyl carbonate and at least a portion of said carbon monoxide to said at least one oxygenated compound, wherein said dimethyl carbonate and said carbon monoxide are reacted in the presence of at least one zeolite catalyst selected from the group consisting of faujasite zeolites, zeolite Beta, Linde Type L (LTL) zeolite, MCM-41, and mixtures thereof.

2. The method of claim 1 wherein said at least one zeolite is a faujasite zeolite.

3. The method of claim 1 wherein said at least one zeolite is zeolite Beta.

4. The method of claim 1 wherein said at least one zeolite is LTL zeolite.

5. The method of claim 1 wherein said at least one zeolite is MCM-41.

6. The method of claim 1 wherein said at least one oxygenated compound is methyl acetate.

7. The method of claim 1 wherein said carbon monoxide is obtained from synthesis gas.

8. The method of claim 1 wherein said dimethyl carbonate is reacted with said carbon monoxide at a temperature of from about 100° C. to about 600° C.

9. The method of claim 8 wherein said dimethyl carbonate is reacted with said carbon monoxide at a temperature of from about 100° C. to about 400° C.

10. The method of claim 1 wherein said dimethyl carbonate is reacted with said carbon monoxide at a pressure of from about 14 psi to about 900 psi.

11. The method of claim 1 wherein said dimethyl carbonate is reacted with said carbon monoxide at a molar ratio of dimethyl carbonate to carbon monoxide of from about 0.25:1 to about 10:1.

12. The method of claim 11 wherein said dimethyl carbonate is reacted with said carbon monoxide at a molar ratio of dimethyl carbonate to carbon monoxide of from about 0.25:1 to about 2:1.

13. The method of claim 12 wherein said dimethyl carbonate is reacted with said carbon monoxide at a molar ratio of dimethyl carbonate to carbon monoxide of from about 0.5:1 to about 1:1.

14. The method of claim 1 wherein said dimethyl carbonate is reacted with said carbon monoxide in a three-phase reactor, wherein said at least one zeolite catalyst is suspended in inert liquid.

15. The method of claim 14 wherein said inert liquid is an inert oil.

16. The method of claim 1 wherein said dimethyl carbonate is reacted with said carbon monoxide in a fixed bed reactor containing said at least one zeolite catalyst.

17. A method of producing methyl acetate, comprising:

(a) reacting dimethyl carbonate with synthesis gas in the presence of at least one zeolite catalyst, said synthesis gas containing carbon monoxide, under conditions which convert at least a portion of said dimethyl carbonate at least a portion of said carbon monoxide to a product comprising methyl acetate, dimethyl ether, formaldehyde, carbon dioxide, and unreacted synthesis gas, wherein said at least one zeolite catalyst is selected from the group consisting of faujasite zeolites, zeolite Beta, Linde Type L (LTL) zeolite, MCM-41, and mixtures thereof;

(b) separating said methyl acetate from said dimethyl ether, said formaldehyde, said carbon dioxide, and said unreacted synthesis gas;

(c) subjecting said dimethyl ether, said formaldehyde, said carbon dioxide, and said unreacted synthesis gas to catalytic reforming to produce additional synthesis gas; and

(d) reacting said unreacted synthesis gas and said additional synthesis gas of step (c) with said dimethyl carbonate in step (a).

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Apr 5, 2022
From: GLAS AMERICAS LLC
To: ENERKEM INC.
Reel/Frame 059506/0878 →
SECURITY INTEREST Recorded Apr 1, 2022
From: ENERKEM INC.
To: COMPUTERSHARE TRUST COMPANY OF CANADA, AS COLLATERAL AGENT FOR THE SECURED PARTIES
Reel/Frame 059477/0253 →
SECURITY INTEREST Recorded Jan 17, 2018
From: ENERKEM INC.
To: GLAS AMERICAS LLC
Reel/Frame 044641/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 19, 2014
From: LYNCH, DAVID
To: ENERKEM, INC.
Reel/Frame 034207/0087 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2014
From: LAVOIE, JEAN-MICHEL; UNIVERSITE DE SHERBROOKE
To: ENERKEM, INC.
Reel/Frame 034083/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2012
From: MARIE-ROSE, STEPHANE; CHORNET, ESTEBAN
To: ENERKEM INC.
Reel/Frame 029506/0887 →
Continuity (2)
Provisional Application 61560570 · Nov 16, 2011
Related Publication 20130123533A1 · May 16, 2013