Bisphosphites having a central 2,3'-biphenol unit

Patent metadata

Field	Value
Publication number	US-2016185685-A1
Application number	US-201514953152-A
Country	US
Kind code	A1
Filing date	Nov 27, 2015
Priority date	Dec 4, 2014
Publication date	Jun 30, 2016
Grant date	—

Abstract

Bisphosphites having a central 2,3′-biphenol unit are useful for catalyzing hydroformylation.

First claim

1 . A compound having one of the two structures I and II:

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 ;
R 9 ′, R 10 ′, R 11 ′, R 12 ′, R 9 ″, R 10 ″, R 11 ″, R 12 ″ are each independently selected from the group consisting of:
—H, and —(C 6 -C 20 )-aryl;
wherein the alkyl and aryl groups may be substituted.

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 of: —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 selected from the group consisting of: —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 2 )-alkyl, and —O—(C 6 -C 20 )-aryl.

4 . The compound according to claim 1 ,
wherein R 4 and R 5 are each —H.

5 . The compound according to claim 1 ,
wherein 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, —S-alkyl, and —S-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 ′, 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 2 )-alkyl, —O—(C 1 -C 12 )-alkyl, and —O—(C 6 -C 20 )-aryl.

7 . The compound according to claim 1 ,
wherein 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 —H.

8 . The compound according to claim 1 ,
wherein R 9 ′, R 10 ′, R 11 ′, R 12 ′, R 9 ″, R 10 ″, R 11 ″, R 2 ″ are each —(C 6 -C 20 )-aryl.

9 . The compound according to claim 1 ,
wherein R 9 ′, R 10 ′, R 11 ′, R 12 ′, R 9 ″, R 10 ″, R 11 ″, R 12 ″ are each phenyl.

10 . The compound according to claim 1 ,
wherein R 9 ′, R 10 ′, R 11 ′, R 12 ′, R 9 ″, R 10 ″, R 11 ″, R 12 ″ are each the same radical.

11 . The compound according to claim 1 ,
having the structure (I).

12 . The compound according to claim 1 ,
having the structure (II).

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

14 . The complex according to claim 13 ,
wherein said compound has the structure (I).

15 . The complex according to claim 13 ,
wherein said compound has the structure (II).

16 . A catalyst for catalyzing a hydroformylation reaction, comprising: the compound according to claim 1 .

17 . The catalyst according to claim 16 ,
wherein said compound has the structure (I).

18 . The catalyst according to claim 16 ,
wherein said compound has the structure (II).

19 . A process for hydroformylation of an olefin, comprising:
a) initially charging an olefin into a reactor; b) adding
i) a complex according to claim 13 ;
or
ii) a compound according to claim 1 and a substance having a metal atom selected from the group consisting of: Rh, Ru, Co, and Ir;
c) feeding into said reactor H 2 and CO, to obtain a reaction mixture; d) heating the reaction mixture, to obtain conversion of the olefin to an aldehyde.

Assignees

• Dyballa Katrin Marie
• Franke Robert
• Boerner Armin
• Selent Detlef
• Evonik Degussa Gmbh

Inventors

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

Classifications

• B01J2531/0241

  Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution · CPC title

• B01J31/185

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

• C07C45/50

  by oxo-reactions · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• B01J31/2221

  At least one oxygen and one phosphorous atom present as complexing atoms in an at least bidentate or bridging ligand · CPC title