Process for reducing the chlorine content of organotetraphosphites

Patent metadata

Field	Value
Publication number	US-10011619-B2
Application number	US-201615363746-A
Country	US
Kind code	B2
Filing date	Nov 29, 2016
Priority date	Dec 3, 2015
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

Universally usable process for reducing the chlorine content of organotetraphosphites.

First claim

The invention claimed is:

1. Process for reducing the chlorine content in an organotetraphosphite of one of the general formulae I and II:

where
R 1 , R 2 , R 3 , R 4 are each independently selected from: —H, —(C 1 -C 12 )-alkyl;
V and W are each independently selected from:
—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-heteroalkyl, —(C 4 -C 20 )-aryl, —(C 4 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-alkyl-(C 4 -C 20 )-aryl, —(C 4 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl-CONH—(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , -(C 4 -C 20 -heteroaryl, —(C 4 -C 20 )-heteroaryl-(C 1 -C 12 )-alkyl, —(C 3 -C 12 )-cycloalkyl, —(C 3 -C 12 )-cycloalkyl-(C 1 -C 12 )-alkyl, —(C 3 -C 12 )-heterocycloalkyl, —(C 3 -C 12 )-heterocycloalkyl-(C 1 -C 12 )-alkyl, —CO—(C 1 -C 12 )-alkyl, —CO—(C 4 -C 20 )-aryl, —CO—(C 4 -C 20 )-heteroalkyl, —(C 4 -C 20 )-aryl-CO—(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl-CO—(C 4 -C 20 )-aryl;
X and Y are each independently selected from O and N;
where, in the case that X is O, n=1,
and, in the case that Y is O, m=1,
and, in the case that X is N, n=1 or 2,
and, in the case that Y is N, m=1 or 2;
Z is selected from:
—(C 1 -C 14 )-alkyl- , —(C 4 -C 20 )-aryl-, —(C 4 -C 20 )-aryl-(C 1 -C 12 )- alkyl-, —(C 1 -C 14 )-heteroalkyl-, —(C 4 -C 20 )-heteroaryl-, —CO—(C 4 -C 14 )-heteroaryl-, —CO—(C 4 -C 20 )-aryl-, —(C 3 -C 12 )-cycloalkyl-, —(C 3 -C 12 )-heterocycloalkyl-, —(C 4 -C 20 )-aryl-CO—(C 4 -C 20 )-aryl-, —(C 1 -C 14 )-alkyl-O—(C 1 -C 14 )-alkyl-;
where the alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups mentioned are optionally mono- or polysubstituted;
comprising the following process steps:
a) contacting the organotetraphosphite with a solution comprising at least one solvent and at least one base, where the at least one solvent is selected from aromatics, alcohols, acetone, ethyl acetate, acetonitrile and ethers, and where the at least one base is selected from amine bases, alkoxides, pyridine, pyridine derivatives, N-methyl-2-pyrrolidone, triethylamine and triethanolamine,
b) adjusting the temperature to a value in the range from −20° C. to +15° C.,
c) removing the purified organotetraphosphite.

2. Process according to claim 1 ,
wherein the at least one solvent is selected from acetonitrile, ethyl acetate, ethanol, propanol, toluene.

3. Process according to claim 1 ,
wherein the solution with which the organotetraphosphite is contacted in step a) contains, as well as the at least one solvent and the at least one base, also max. 5% water based on the solvent content.

4. Process according to claim 1 ,
wherein the at least one base is selected from triethylamine and dimethylaininobutane.

5. Process according to claim 1 ,
where X and Y are O.

6. Process according to claim 1 ,
where X and Y are N.

7. Process according to claim 1 ,
where V and W are each independently selected from:
—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl, —(C 4 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 4 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-alkyl-(C 4 -C 20 )-aryl, —(C 4 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl.

8. Process according to claim 1 ,
where V and W are, or just one of the substituents V and W is,

where R 5 , R 6 , R 7 , R 8 , R 9 are independently selected from —H, —(C 1 -C 12 )-alkyl,
—O—(C 1 -C 12 )-alkyl, -phenyl, —COO—(C 1 -C 12 )-alkyl.

9. Process according to claim 1 ,
where Z is selected from:

where R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 are each independently selected from:
—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen (such as Cl, F, Br, I), COO—(C 1 -C 12 )-alkyl, CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , —N[(C 1 -C 12 )-alkyl] 2 .

10. Process according to claim 1 ,
wherein the organotetraphosphite used in process step a) has a chlorine content of 1500 ppm to 100 000 ppm.

11. Process according to claim 1 ,
wherein the purified organotetraphosphite has a chlorine content of <1000 ppm.

12. Process according to claim 1 ,
where R 1 , R 3 , R 4 are —H.

13. Process according to claim 1 ,
where R 2 is tert-butyl.

14. Process according to claim 1 ,
where the organotetraphosphite has one of the structural formulae III, IV, V, VI, VII, VIII, IX, X, XI, XII, XIII, XIV and XV:

Assignees

• Evonik Degussa Gmbh

Inventors

• Dyballa Katrin Marie
• Franke Robert

Classifications

• C07F9/65744 Primary

  condensed with carbocyclic or heterocyclic rings or ring systems · CPC title

• C07F9/65848

  Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring · CPC title

• C07F9/65746 Primary

  the molecule containing more than one cyclic phosphorus atom · CPC title

• C07F9/222

  Amides of phosphoric acids · CPC title

• C07F9/145

  with hydroxyaryl compounds · CPC title