Monophosphites comprising an anthrol

Patent metadata

Field	Value
Publication number	US-2016159718-A1
Application number	US-201514953210-A
Country	US
Kind code	A1
Filing date	Nov 27, 2015
Priority date	Dec 4, 2014
Publication date	Jun 9, 2016
Grant date	—

Abstract

Monophosphites comprising an anthrol are useful for catalyzing hydroformylation of an olefin to an aldehyde.

First claim

1 . A compound having one of the structures I or 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 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 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.

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, —(C 6 -C 20 )-aryl, —S-alkyl, —S-aryl, halogen, —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, and —N[(C 1 -C 12 )-alkyl] 2 .

3 . The compound according to claim 1 ,
wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 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, —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, and —N[(C 1 -C 12 )-alkyl] 2 .

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, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, —S-alkyl, -S-aryl, and halogen.

5 . The compound according to claim 1 ,
wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 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, and halogen.

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 1 ,
wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 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 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, and —O—(C 1 -C 12 )-alkyl.

9 . The compound according to claim 1 ,
wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 are each independently selected from the group consisting of: —H, —(C 1 -C 12 )-alkyl, and —O—(C 1 -C 12 )-alkyl.

10 . The compound according to claim 1 ,
having a structure selected from the group consisting of the following structures 1 to 10:

11 . The compound according to claim 1 ,
wherein the compound has the structure I.

12 . The compound according to claim 1 ,
wherein the compound has 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
• Geilen Frank
• Fridag Dirk
• Hess Dieter
• Selent Detlef
• Boerner Armin
• Evonik Degussa Gmbh

Inventors

• Dyballa Katrin Marie
• Franke Robert
• Geilen Frank
• Fridag Dirk
• Hess Dieter
• Selent Detlef
• Boerner Armin

Classifications

• C07B41/06

  of carbonyl groups · CPC title

• C07F9/65744

  condensed with carbocyclic or heterocyclic rings or ring systems · CPC title

• B01J31/185

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

• B01J2531/822

  Rhodium · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title