IP Library Granted Patent US 9,650,401
Granted Patent B2
US 9,650,401 · App. 15/117,894 · Granted May 16, 2017

Method for reducing the chlorine content of organobisphosphites

Inventors: Katrin Marie Dyballa (Recklinghausen, DE); Robert Franke (Marl, DE)
Assignee: EVONIK DEGUSSA GMBH
C07F9/65746
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Quick Facts
Patent No.
US 9,650,401
App. No.
15/117,894
Granted
May 16, 2017
Kind
B2
Abstract

The invention relates to a universally usable process for reducing the chlorine content of organobisphosphites.

Claims (48)

1. Process for reducing the chlorine content in an organobisphosphite of one of the general formulae I, II, III, IV, V and VI:

where

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 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, —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 ;

and the four following pairs of radicals are not both the same radical in all four pairs:

R 1 and R 5 , R 2 and R 6 , R 3 and R 7 , R 4 and R 8 ;

comprising the process steps of:

a) partly or fully dissolving the organobisphosphite in a first solution,

b) introducing the first solution into a second solution, which results in precipitation of the purified organobisphosphite,

wherein

the first solution comprises a first solvent and a first base,

the second solution comprises a second solvent and a second base,

and

the first solvent is selected from:

aromatics, alcohols, acetone, ethyl acetate, acetonitrile, ethers,

the second solvent is selected from:

aromatics, C5-C10-alkanes, alcohols, acetone, ethyl acetate, acetonitrile, ethers,

the first base is selected from:

amine bases, alkoxides, pyridine, pyridine derivatives, N-methyl-2-pyrrolidone, triethanolamine,

the second base is selected from:

amine bases, alkoxides, pyridine, pyridine derivatives, N-methyl-2-pyrrolidone, triethanolamine, and the organobisphosphite has better solubility in the first solvent than in the second solvent.

2. Process according to claim 1 ,

wherein the first solvent is selected from: ethyl acetate, anisole, ortho-xylene, toluene, acetone, methanol, ethanol, propanol, isopropanol, acetonitrile.

3. Process according to claim 1 ,

wherein the second solvent is selected from: ethyl acetate, anisole, ortho-xylene, toluene, acetone, methanol, ethanol, propanol, isopropanol, acetonitrile, tetrahydrofuran, diethyl ether, glycol, C5-C10-alkanes.

4. Process according to claim 1 ,

wherein the first base is selected from: triethylamine, dimethylaminobutane, pentylamine, hexylamine, dibutylamine, N-methyl-2-pyrrolidone, triethanolamine, sodium methoxide, sodium ethoxide, pyridine, dimethylaminopyridine.

5. Process according to claim 1 ,

wherein the second base is selected from: triethylamine, dimethylaminobutane, pentylamine, hexylamine, dibutylamine, N-methyl-2-pyrrolidone, triethanolamine, sodium methoxide, sodium ethoxide, pyridine, dimethylaminopyridine.

6. Process according to claim 1 ,

wherein the second solution comprises a third solvent non-identical to the second solvent.

7. Process according to claim 6 ,

wherein the third solvent is selected from: aromatics, alcohols, acetone, ethyl acetate, acetonitrile, ethers.

8. Process according to claim 1 ,

wherein the organobisphosphite is dissolved fully in the first solution in process step a).

9. Process according to claim 1 ,

wherein the first base and the second base are not the same base.

10. Process according to claim 1 ,

wherein the organobisphosphite has a chlorine content of 1500 ppm to 100 000 ppm on introduction in process step b).

11. Process according to claim 1 ,

wherein the second solution is heated to a temperature in the range from −20° C. to 120° C. before the first solution is introduced into the second solution in process step b).

12. Process according to claim 1 ,

wherein the organobisphosphite has one of the general formulae I, II, IV and VI:

13. Process according to claim 1 ,

wherein the organobisphosphite has one of the general formulae I, II and VI:

14. Process according to claim 1 ,

wherein the organobisphosphite has one of the general formulae I, II and VI:

and where

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2024
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 066242/0585 →
CHANGE OF NAME Recorded Mar 29, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052254/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2017
From: DYBALLA, KATRIN MARIE; FRANKE, ROBERT
To: EVONIK DEGUSSA GMBH
Reel/Frame 041580/0719 →
Priority Claims (1)
DE 10 2014 202 500 · Feb 12, 2014 · national
Continuity (1)
Related Publication 20170057985A1 · Mar 2, 2017