IP Library Granted Patent US 9,840,524
Granted Patent B2
US 9,840,524 · App. 15/311,996 · Granted Dec 12, 2017

Process for reducing the chlorine content of organomonophosphites using two solutions

Inventors: Katrin Marie Dyballa (Recklinghausen, DE); Robert Franke (Marl, DE)
Assignee: EVONIK DEGUSSA GMBH
C07F9/062C07F9/025
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Quick Facts
Patent No.
US 9,840,524
App. No.
15/311,996
Granted
Dec 12, 2017
Kind
B2
Abstract

Process with universal usefulness for reducing the chlorine content of organomonophosphites, using two solutions.

Claims (55)

1. A process for reducing the chlorine content in an organomonophosphite of one of the general formulae I, II, III, IV, V, VI, VII, VIII, IX and X:

where the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 35 , R 41 , R 42 , R 43 , R 44 and R 45 are selected each independently from:

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl;

and R 10 is —(C 1 -C 12 )-alkyl;

and T is selected from:

—CH 3 , —CF 3 , —CH 2 C 6 H 5 ;

and Q is selected from:

—(C 1 -C 12 )-alkyl-, —C(CH 3 ) 3 ;

and V is selected from:

—CH 2 CH 2 COCH 3 , —C(CH 3 ) 3 , —C 6 H 5 ;

and W is selected from:

-Me, —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 -cyclo-C 3 H 5 , —CH(CH 3 ) 2 , -cyclo-C 6 H 11 , —C(CH 3 ) 3 , —CH 2 C 6 H 5 , —CH 2 C 6 H 3 -2,4-(CH 3 ) 2 ;

and X and Y are each independently selected from:

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl;

and Z is selected from:

—(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-, —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl-;

and the alkyl, cycloalkyl, and aryl groups mentioned may be substituted;

comprising the process steps of:

a) partly or fully dissolving the organomonophosphite in a first solution comprising a first solvent selected from the group consisting of aromatics, alcohols, acetone, ethyl acetate, acetonitrile, and ether;

b) introducing the first solution into a second solution comprising a second solvent selected from the group consisting of aromatics, C 5 -C 10 -alkanes, alcohols, acetone, ethyl acetate, acetonitrile, and ether,

where at least one of the two solutions comprises dimethylaminobutane or triethylamine or triethanolamine in addition to the respective first solvent and/or second solvent;

c) precipitating the purified organomonophosphite, wherein steps a), b), and c) are performed without water.

2. The 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. The process according to claim 1 ,

wherein the first solvent is toluene.

4. The 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, C 5 -C 10 -alkanes.

5. The process according to claim 1 ,

wherein the second solvent is acetonitrile or methanol.

6. The process according to claim 1 ,

wherein the second solution comprises a third solvent.

7. The process according to claim 1 ,

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

8. The process according to claim 1 ,

wherein the purified organomonophosphite has a chlorine content of <1000 ppm.

9. The process according to claim 1 ,

wherein the purified organomonophosphite has a chlorine content of <200 ppm.

10. The process according to claim 1 ,

wherein, following the introduction of the first solution into the second solution, the temperature is lowered to −20 to +10° C. in order to increase the degree of precipitation.

11. The process according to claim 1 ,

wherein the organomonophosphite has one of the general formulae I, II, III and IV:

12. The process according to claim 1 ,

wherein

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;

and W is —CH 3 ;

and Q is —C(CH 3 ) 3 .

13. The process according to claim 1 ,

where Z is:

and

where R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 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 .

14. The process of claim 1 , wherein at least one of the two solutions comprises dimethylaminobutane.

15. The process of claim 1 , wherein at least one of the two solutions comprises triethylamine.

16. The process of claim 1 , wherein at least one of the two solutions comprises triethanolamine.

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 Nov 6, 2017
From: DYBALLA, KATRIN MARIE; FRANKE, ROBERT
To: EVONIK DEGUSSA GMBH
Reel/Frame 044040/0187 →
Priority Claims (6)
DE 10 2014 209 532 · May 20, 2014 · national
DE 10 2014 209 533 · May 20, 2014 · national
DE 10 2014 209 534 · May 20, 2014 · national
DE 10 2014 209 535 · May 20, 2014 · national
DE 10 2014 209 536 · May 20, 2014 · national
DE 10 2015 202 722 · Feb 16, 2015 · national
Continuity (1)
Related Publication 20170121355A1 · May 4, 2017