Process for preparing dialkyl carbonate and alkanediol

Patent metadata

Field	Value
Publication number	US-2022017450-A1
Application number	US-201917311826-A
Country	US
Kind code	A1
Filing date	Dec 16, 2019
Priority date	Dec 18, 2018
Publication date	Jan 20, 2022
Grant date	—

Abstract

The invention relates to a process wherein a dialkyl carbonate stream containing an ether alkanol impurity is subjected to extractive distillation using an extraction solvent to obtain a top stream comprising dialkyl carbonate and a bottom stream comprising the extraction solvent and the ether alkanol impurity, wherein the extraction solvent is an organic compound containing one or more hydroxyl groups and one or more ester moieties and/or ether moieties. Further, the invention relates to a process for making a diaryl carbonate, comprising reacting an aryl alcohol with a stream containing a dialkyl carbonate from which stream an ether alkanol impurity has been removed in accordance with the above-described process.

First claim

1 . A process for the preparation of a dialkyl carbonate and an alkanediol, comprising:
(a) reacting an alkylene carbonate and an alkanol to obtain a product mixture containing unconverted alkylene carbonate, unconverted alkanol, dialkyl carbonate, alkanediol and an ether 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 ether alkanol impurity; (c) recovering the alkanediol; (d) separating unconverted alkanol from the top stream obtained in step (b) to obtain a bottom stream containing dialkyl carbonate and the ether alkanol impurity; and (e) subjecting the bottom stream obtained in step (d) to extractive distillation using an extraction solvent to obtain a top stream comprising dialkyl carbonate and a bottom stream comprising the extraction solvent and the ether alkanol impurity, wherein the extraction solvent is an organic compound containing one or more hydroxyl groups and one or more ester moieties and/or ether moieties; and (f) removing the ether alkanol impurity from the bottom stream obtained in step (e) and recycling the extraction solvent to step (e).

2 . The process according to claim 1 , wherein the alkylene carbonate is a C2-C6 alkylene carbonate, and the alkanol is a C1-C4 alkanol.

3 . The process according to claim 2 , wherein the alkylene carbonate is ethylene carbonate or propylene carbonate, the alkanol is ethanol and the dialkyl carbonate is diethyl carbonate.

4 . The process according to claim 1 , wherein the extraction solvent is an ester of formula R i X(C=0) 0R 2 wherein X is absent or is an oxygen atom and Ri and R2 comprise a total of 2 to 20 carbon atoms and contain a total of one or more hydroxyl groups.

5 . The process according to claim 4 , wherein the ester of formula RIX(C=0)0R 2 is:
an ester wherein X is absent which originates from reacting an alkanol of formula R2OH containing 2 or more hydroxyl groups with a carboxylic acid of formula Ri(C=0)0H, wherein at least one of the hydroxyl groups of the alkanol is not esterified and one of the hydroxyl groups of the alkanol is esterified; or an ester wherein X is absent, and Ri contains one or more hydroxyl groups which originates from reacting an alkanol of formula R2OH containing 1 or more hydroxyl groups with a carboxylic acid of formula Ri(C=0)0H wherein Ri contains one or more hydroxyl groups; or an alkylene carbonate wherein X is an oxygen atom and Ri and R2 are connected to form a ring; or a carbonate wherein X is an oxygen atom and Ri and R2 are not connected to form a ring.

6 . The process according to claim 1 , wherein the extraction solvent is an ether of formula R4-O—R5 and R4 and R5 comprise a total of 2 to 20 carbon atoms and contain a total of one or more hydroxyl groups.

7 . The process according to claim 6 , wherein the ether of formula R4-O—R5 is:
a polyalkylene glycol and R4 and R5 contain a total of two hydroxyl groups; or
an ether of an alkanol of formula R4OH containing 2 or more hydroxyl groups, wherein at least one of the hydroxyl groups of the alkanol is not etherified and at least one of the hydroxyl groups of the alkanol is etherified, and an alkanol of formula R5OH containing 1 or more hydroxyl groups; or an acetal or a ketal.

8 . A process for removing an ether alkanol impurity from a stream containing a dialkyl carbonate and the ether alkanol impurity, comprising:
(e) subjecting the stream containing a dialkyl carbonate and the ether alkanol impurity to extractive distillation using an extraction solvent to obtain a top stream comprising dialkyl carbonate and a bottom stream comprising the extraction solvent and the ether alkanol impurity, wherein the extraction solvent is an organic compound containing one or more hydroxyl groups and one or more ester moieties and/or ether moieties; and (f) removing the ether alkanol impurity from the bottom stream obtained in step (e) and recycling the extraction solvent to step (e).

9 . The process for making a diaryl carbonate, comprising contacting, in the presence of a transesterification catalyst, an aryl alcohol with a stream containing a dialkyl carbonate from which stream an ether alkanol impurity has been removed in accordance with the process of claim 1 .

10 . The process for making a diaryl carbonate, comprising removing an ether alkanol impurity from a stream containing a dialkyl carbonate and the ether alkanol impurity 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.

Assignees

• Shell Oil Co

Inventors

• Fischer Kai Jürgen
• Van Der Heide Evert

Classifications

• C07C68/08

  Purification; Separation; Stabilisation · CPC title

• C07C68/065 Primary

  from alkylene carbonates · CPC title

• C07C69/96

  Esters of carbonic or haloformic acids · CPC title