IP Library Granted Patent US 7,745,655
Granted Patent B1
US 7,745,655 · App. 10/505,879 · Granted Jun 29, 2010

Method for the preparation of biphosphites

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Quick Facts
Patent No.
US 7,745,655
App. No.
10/505,879
Granted
Jun 29, 2010
Kind
B1
Abstract

The present invention relates to a process for preparing bisphosphites which contain dioxaphosphorinone units.

Claims (27)

1. A process for preparing bisphosphites of the formula I

wherein R 1 , R 2 , R 3 , R 4 are independently selected from H, aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, aromatic-aromatic, aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms, F, Cl, Br, I, —CF 3 , —OR 7 , —COR 7 , —CO 2 R 7 , —CO 2 M, —SR 7 , —SO 2 R 7 , —SOR 7 , —SO 3 R 7 , —SO 3 M, —SO 2 NR 7 R 8 , NR 7 R 8 , N═CR 7 R 8 , or NH 2 , wherein R 1 to R 4 may be covalently linked to one another,

R 7 , R 8 are independently selected from H or a substituted or unsubstituted, aliphatic or aromatic hydrocarbon radical having from 1 to 25 carbon atoms, atoms,

M is an alkali metal ion, alkaline earth metal ion, ammonium ion, or phosphonium ion,

Q is a divalent aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, or aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms,

Z, Y are each Cl, Br, or I,

W, X are independently selected from an aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, aromatic-aromatic, or aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms and may be covalently linked to one another,

the process comprising carrying out the reaction sequence

wherein the reaction steps a), b) and c) are carried out in aprotic and nonpolar solvents,

the adduct base•HY or base•HZ is filtered off after at least one of the reaction steps a), b) and c) and

the end product is isolated and purified.

2. The process as claimed in claim 1 , wherein said base comprises tertiary amines.

3. The process as claimed in claim 1 , wherein said aprotic and nonpolar solvents are at least one selected from the group consisting of benzene, toluene, ethylbenzene, and cyclohexane.

4. The process as claimed in claim 1 , wherein W and X are an independently selected from aliphatic, alicyclic, aliphaticalicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, aromatic-aromatic, or aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms and are covalently linked as in the formula V

5. The process as claimed in claim 1 , wherein W and X are each an aromatic hydrocarbon radical having from 1 to 50 carbon atoms and are covalently linked as shown in the formula VI

wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are independently selected from H aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic-aromatic, aromatic, aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms, F, Cl, Br, I, —CF 3 , —OR 25 , —COR 25 , —CO 2 R 25 , —CO 2 M, —SR 25 , —SO 2 R 25 , —SOR 25 , —SO 3 R 25 , —SO 3 M, —SO 2 NR 25 R 26 , NR 25 R 26 , N═CR 25 R 26 , or NH 2 , wherein R 9 to R 14 may be covalently linked to one another;

R 25 and R 26 are independently selected from H or a substituted or unsubstituted, aliphatic or aromatic hydrocarbon radical having from 1 to 25 carbon atoms, and

M is an alkali metal ion, alkaline earth metal ion, ammonium ion, or phosphonium ion.

6. The process as claimed in claim 1 , wherein W and X are each an aromatic hydrocarbon radical having from 1 to 50 carbon atoms and are covalently linked as shown in the formula VII

wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 are independently selected from H, aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic-aromatic, aromatic, aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms, F, Cl, Br, I, —CF 3 , —OR 25 , —COR 25 , —CO 2 R 25 , —CO 2 M, —SR 25 , —SO 2 R 25 , —SOR 25 , —SO 3 R 25 , —SO 3 M, —SO 2 NR 25 R 26 , NR 25 R 26 , N═CR 25 R 26 , or NH 2 , wherein R 9 to R 16 may be covalently linked to one another,

R 25 and R 26 are independently selected from H or a substituted or unsubstituted, aliphatic or aromatic hydrocarbon radical having from 1 to 25 carbon atoms, and

M is an alkali metal ion, alkaline earth metal ion, ammonium ion, or phosphonium ion.

7. The process as claimed in claim 1 , wherein Q is a hydrocarbon radical of the formula VIII

wherein R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 are independently selected from H, aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic-aromatic, aromatic, aliphatic-aromatic hydrocarbon radical having from 1 to 50 carbon atoms, F, Cl, Br, I, —CF 3 , —OR 25 , —COR 25 , —CO 2 R 25 , —CO 2 M, —SR 25 , —SO 2 R 25 , —SOR 25 , —SO 3 R 25 , —SO 3 M, —SO 2 NR 25 R 26 , NR 25 R 26 , N═CR 25 R 26 , or NH 2 , wherein R 17 to R 24 may be covalently linked to one another,

R 25 and R 26 are independently selected from H or a substituted or unsubstituted, aliphatic or aromatic hydrocarbon radical having from 1 to 25 carbon atoms, and

M is an alkali metal ion, alkaline earth metal ion, ammonium ion, or phosphonium ion with the positions a and b serving as linkage points.

8. The process as claimed in claim 1 , wherein X and W are covalently linked and the corresponding starting material B used in reaction step c) is prepared according to reaction step d) in an aprotic and nonpolar solvent

Assignments (2)
CHANGE OF NAME Recorded Feb 25, 2010
From: OXENO OLEFINCHEMIE GMBH
To: EVONIK OXENO GMBH
Reel/Frame 024006/0287 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2004
From: BORGMANN, CORNELIA
To: OXENO OLEFINCHEMIE GMBH
Reel/Frame 015937/0858 →