Bisphosphites having an unsymmetric outer biphenol unit

Patent metadata

Field	Value
Publication number	US-10214550-B2
Application number	US-201715620204-A
Country	US
Kind code	B2
Filing date	Jun 12, 2017
Priority date	Dec 4, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

Disclosed herein are compounds of formula (I):

wherein:
the groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 1 ′, R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 1 ″, R 2 ″, R 3 ″, R 4 ″, R 5 ″, R 6 ″, R 7 ″, R 8 ″ are defined herein; and
at least one of the following conditions is satisfied:
two radicals from at least one of the four following pairs of radicals are not the same radical: R 1 ′ and R 8 ′, R 2 ′ and R 7 ′, R 3 ′ and R 6 ′, R 4 ′ and R 5 ′, and two radicals from at least one of the four following pairs of radicals are not the same radical: R 1 ″ and R 8 ″, R 2 ″ and R 7 ″, R 3 ″ and R 6 ″, R 4 ″ and R 5 ′.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, —S-alkyl, —S-aryl, halogen, COO—(C 1 -C 12 )-alkyl, CONH—(C 1 -C 12 )-alkyl, —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 ;
R 1 ′, R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 1 ″, R 2 ″, R 3 ″, R 4 ″, R 5 ″, R 6 ″, R 7 ″, R 8 ″ are each independently selected from the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, —S-alkyl, —S-aryl, halogen, COO—(C 1 -C 12 )-alkyl, CONH—(C 1 -C 12 )-alkyl, —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 ; wherein
the alkyl and aryl groups may be substituted;
R 1 ′ and R 8 ′ are not the same radical; and
R 1 ″ and R 8 ″ are not the same radical.

2. The compound 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 the group consisting —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —S-alkyl, and —S-aryl.

3. The compound 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 the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

4. The compound 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 the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

5. The compound according to claim 4 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

6. The compound 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 the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

7. The compound according to claim 2 , wherein R 1 ″, R 2 ″, R 3 ″, R 4 ″, R 5 ″, R 6 ″, R 7 ″, R 8 ″ are each independently selected from the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

8. The compound according to claim 1 , wherein:
R 1 , R 1 ′ and R 1 ″ are the same radical; and
R 8 , R 8 ′ and R 8 ″ are the same radical.

9. The compound according to claim 1 , wherein:
two radicals from at least one of the three following pairs of radicals are not the same radical: R 2 ′ and R 7 ′, R 3 ′ and R 6 ′, R 4 ′ and R 5 ′; and
two radicals from at least one of the three following pairs of radicals are not the same radical: R 2 ″ and R 7 ″, R 3 ″ and R 6 ″, R 4 ″ and R 5 ″.

10. The compound according to claim 2 , wherein:
two radicals from at least one of the three following pairs of radicals are not the same radical: R 2 ′ and R 7 ′, R 3 ′ and R 6 ′, R 4 ′ and R 5 ′; and
two radicals from at least one of the three following pairs of radicals are the same radical: R 2 ″ and R 7 ″, R 3 ″ and R 6 ″, R 4 ″ and R 5 ″.

11. A complex, comprising:
a compound according to claim 1 ; and
a metal atom selected from the group consisting of: Rh, Ru, Co, and Ir.

12. A catalyst for catalyzing a hydroformylation reaction, the catalyst comprising the compound according to claim 1 complexed to a metal.

13. A process for hydroformylation of an olefin, the process comprising:
a) initially charging an olefin into a reactor;
b) adding the complex according to claim 11 to the reactor;
c) feeding H 2 and CO into the reactor, to obtain a reaction mixture; and
d) heating the reaction mixture, to convert the olefin to an aldehyde by hydroformylation.

14. A process for hydrofomrylation of an olefin, the process comprising:
a) initially charging an olefin into a reactor;
b) adding the compound according to claim 1 and a substance having a metal atom selected from the group consisting of Rh, Ru, Co, and Ir to the reactor;
c) feeding H 2 and CO into the reactor, to obtain a reaction mixture; and
d) heating the reaction mixture, to convert the olefin to an aldehyde by hydroformylation.

Assignees

• Evonik Degussa Gmbh

Inventors

• Dyballa Katrin Marie
• Franke Robert
• Fridag Dirk
• Boerner Armin
• Selent Detlef

Classifications

• C07B41/06

  of carbonyl groups · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• B01J2531/822

  Rhodium · CPC title

• B01J31/185

  Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof · CPC title