IP Library Granted Patent US 8,907,116
Granted Patent B2
US 8,907,116 · App. 13/390,124 · Granted Dec 9, 2014

Process for removing an alkanol impurity from a dialkyl carbonate stream

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Quick Facts
Patent No.
US 8,907,116
App. No.
13/390,124
Granted
Dec 9, 2014
Kind
B2
Abstract

The invention relates to a process for removing an alkanol impurity from a stream containing a dialkyl carbonate and the alkanol impurity, comprising contacting the stream with an aryl group containing ester and a catalyst to effect reaction of the alkanol impurity with the aryl group containing ester.

Claims (27)

1. A process for removing an alkanol impurity from a stream containing a dialkyl carbonate and the alkanol impurity, comprising contacting the stream with an aryl group containing ester and a transesterification catalyst such that the alkanol impurity reacts with the aryl group containing ester, wherein the dialkyl carbonate is a di(C 1 -C 5 )alkyl carbonate and the alkanol impurity is an ether alkanol.

2. A process according to claim 1 , wherein the aryl group containing ester is diphenyl carbonate.

3. A process according to claim 2 , wherein the dialkyl carbonate is a diethyl carbonate.

4. A process according to claim 1 , wherein the alkanol impurity is an alkoxy alkanol.

5. A process according to claim 4 , wherein the dialkyl carbonate is diethyl carbonate and the alkanol impurity is 2-ethoxyethanol.

6. A process according to claim 1 , wherein the alkanol impurity is 2-ethoxyethanol.

7. A process according to claim 1 , wherein the stream containing the dialkyl carbonate and the alkanol impurity is contacted with a stream originating from a process for producing diphenyl carbonate from a dialkyl carbonate and phenol and/or purifying crude diphenyl carbonate, the latter stream containing a catalyst, and an aryl group containing ester.

8. A process according to claim 7 wherein the transesterification catalyst is a titanium containing catalyst.

9. A process according to claim 7 wherein the aryl group containing ester is selected from the group consisting of diphenyl carbonate and derivatives of diphenyl carbonate.

10. A process according to claim 9 wherein the derivatives of diphenyl carbonate are selected from the group consisting of phenyl salicylate and derivatives of phenyl salicylate.

11. A process according to claim 1 , wherein the stream containing a dialkyl carbonate and the alkanol impurity is obtained by a process for the preparation of a dialkyl carbonate and an alkanediol comprising:

(a) reacting an alkylene carbonate and an alkanol in the presence of a transesterification catalyst to obtain a product mixture containing unconverted alkylene carbonate, unconverted alkanol, dialkyl carbonate, alkanediol and an alkanol impurity;

(b) separating unconverted alkylene carbonate and alkanediol from the product mixture to obtain a top stream containing unconverted alkanol, dialkyl carbonate and the alkanol impurity;

(c) recovering the alkanediol; and

(d) separating unconverted alkanol from the top stream containing unconverted alkanol, dialkyl carbonate and the alkanol impurity obtained in step (b) to obtain a bottom stream containing dialkyl carbonate and the alkanol impurity,

which process further comprises

(e) contacting the bottom stream containing dialkyl carbonate and the alkanol impurity obtained in step (d) with an aryl group containing ester and a catalyst to effect reaction of the alkanol impurity with the aryl group containing ester.

12. A process according to claim 11 , wherein the alkylene carbonate is ethylene carbonate, the unconverted alkanol is ethanol, the dialkyl carbonate is diethyl carbonate, the alkanediol is monoethylene glycol and the alkanol impurity is 2-ethoxyethanol.

13. A process according to claim 1 , wherein the stream containing a dialkyl carbonate and the alkanol impurity is obtained by a process for the preparation of a dialkyl carbonate and an alkanediol comprising:

(a) reacting an alkylene carbonate and an alkanol in the presence of a transesterification catalyst to obtain a product mixture containing unconverted alkylene carbonate, unconverted alkanol, dialkyl carbonate, alkanediol and an alkanol impurity;

(b) separating unconverted alkylene carbonate and alkanediol from the product mixture to obtain a top stream containing unconverted alkanol, dialkyl carbonate and the alkanol impurity;

(c) recovering the alkanediol; and

(d) contacting the top stream containing unconverted alkanol, dialkyl carbonate and the alkanol impurity obtained in step (b) with an aryl group containing ester and a catalyst to effect reaction of the alkanol impurity with the aryl group containing ester, and separating unconverted alkanol to obtain a bottom stream containing dialkyl carbonate.

14. A process according to claim 13 , wherein the alkylene carbonate is ethylene carbonate, the unconverted alkanol is ethanol, the dialkyl carbonate is diethyl carbonate, the alkanediol is monoethylene glycol and the alkanol impurity is 2-ethoxyethanol.

15. A process according to claim 1 , further comprising the step of removing impurities resulting from the reaction of the alkanol impurity with the aryl group containing ester, from the stream containing the dialkyl carbonate.

16. A process for making a diaryl carbonate, comprising contacting a stream containing a dialkyl carbonate and an alkanol impurity with an aryl group containing ester and a catalyst to effect reaction of the alkanol impurity with the aryl group containing ester in accordance with the process of claim 1 , and then contacting, in the presence of a transesterification catalyst, an aryl alcohol with the stream containing the dialkyl carbonate.

17. A process according to claim 16 , wherein the diaryl carbonate is diphenyl carbonate and the aryl alcohol is phenol.

Assignments (2)
CHANGE OF NAME Recorded Mar 7, 2022
From: SHELL OIL COMPANY
To: SHELL USA, INC.
Reel/Frame 059694/0819 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2012
From: ALLAIS, CYRILLE PAUL; VAPORCIYAN, GARO GARBIS
To: SHELL OIL COMPANY
Reel/Frame 028155/0768 →