IP Library Granted Patent US 9,751,904
Granted Patent B2
US 9,751,904 · App. 15/312,024 · Granted Sep 5, 2017

Method for reducing the chlorine content of organomonophosphites using dimethylaminobutane, triethylamine or triethanolamine

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Quick Facts
Patent No.
US 9,751,904
App. No.
15/312,024
Granted
Sep 5, 2017
Kind
B2
Abstract

The invention relates to a universally applicable method for reducing the chlorine content of organomonophosphites using dimethylaminobutane or triethylamine.

Claims (54)

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 , —CH 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 aromatics, alcohols, acetone, ethyl acetate, acetonitrile, ether, water;

where the first solution comprises dimethylaminobutane or triethylamine or triethanolamine;

c) the purified organomonophosphite is precipitated.

2. The process as claimed in claim 1 ,

which comprises the additional process step of:

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

3. The process as claimed in claim 1 ,

wherein the first solution comprises dimethylaminobutane.

4. The process as claimed in claim 1 ,

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

5. The process as claimed in claim 1 ,

wherein the first solvent is toluene.

6. The process as claimed in claim 2 ,

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, water.

7. The process as claimed in claim 2 ,

wherein the second solvent is acetonitrile.

8. The process as claimed in claim 2 ,

wherein the second solution comprises dimethylaminobutane or triethylamine.

9. The process as claimed in claim 1 ,

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

10. The process as claimed in 1 ,

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

11. The process as claimed in claim 2 ,

wherein the second solution is brought to a temperature in the range from −10° C. to 80° C. before the first solution is introduced into the second solution in process step b).

12. The process as claimed in claim 1 ,

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

13. The process as claimed in 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 .

14. The process as claimed in 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, —COON, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , —N[(C 1 -C 12 )-alkyl] 2 .

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 Jul 5, 2017
From: DYBALLA, KATRIN MARIE; FRANKE, ROBERT
To: EVONIK DEGUSSA GMBH
Reel/Frame 043085/0423 →