Preparing cyclocarbonate-functionalized compounds

Patent metadata

Field	Value
Publication number	US-9079871-B2
Application number	US-201214368131-A
Country	US
Kind code	B2
Filing date	Nov 29, 2012
Priority date	Dec 29, 2011
Publication date	Jul 14, 2015
Grant date	Jul 14, 2015

Abstract

An improved process is proposed for preparing cyclocarbonate-functionalized compounds of the general formula (I)

where R 1 and R 2 in each occurrence are independently selected from hydrogen, methyl and ethyl, l in each occurrence independently is from 2 to 50, m in each occurrence independently is 0 or 1, and n is =3, subject to the proviso that the sum of all l values in the molecule is from 5 to 100, by reacting a chloroformate of formula (II)

with a trifunctional amine of the general formula (III)

characterized in that the reacting is carried out in an aqueous/organic two-phase system in the presence of an auxiliary base and of a phase transfer catalyst.

First claim

The invention claimed is:

1. A process for preparing cyclocarbonate-functionalized compounds of the general formula (I)

where R 1 and R 2 in each occurrence are independently selected from hydrogen, methyl and ethyl,
l in each occurrence independently is from 2 to 50,
m in each occurrence independently is 0 or 1, and
n is =3,
subject to the proviso that the sum of all l values in the molecule is from 5 to 100, by reacting a chloroformate of formula (II)

with a trifunctional amine of the general formula (III)

characterized in that
the reaction is carried out in an aqueous/organic two-phase system in the presence of an auxiliary base and of a phase transfer catalyst.

2. The process according to claim 1 , characterized in that the organic solvent is selected from tetrahydrofuran, diethyl ether, chloroform, methylene chloride and mixtures thereof.

3. The process according to claim 1 , characterized in that the auxiliary base is selected from sodium bicarbonate, pyridine, triethylamine and mixtures thereof.

4. The process according to claim 1 , characterized in that the phase transfer catalyst is selected from quaternary ammonium salts.

5. The process according to claim 1 , characterized in that 0.1% to 10% by weight of phase transfer catalyst is used, based on the total amount of substance.

6. The process according to claim 1 , characterized in that it is carried out at room temperature.

7. The process according to claim 4 wherein the quaternary ammonium salt is tetrabutylammonium hydrogensulphate.

Assignees

• Basf S E
• Basf Se

Inventors

• Mezger Jochen
• Walther Burkhard
• Mecfel-Marczewski Joanna
• Klopsch Rainer

Classifications

• C07D407/14

  containing three or more hetero rings · CPC title

• C07D317/38

  Ethylene carbonate · CPC title

• C07D307/33

  in position 2, the oxygen atom being in its keto or unsubstituted enol form · CPC title

• C07D317/40

  Vinylene carbonate; Substituted vinylene carbonates · CPC title

• C07D317/36 Primary

  Alkylene carbonates; Substituted alkylene carbonates · CPC title