Bisphosphites having an unsymmetric outer biphenol unit
View Patent ↗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 ′.
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.