US 11,773,049 B2
Ru-catalyzed domino hydroformylation/hydrogenation/esterification using phosphine ligands
Peter Kucmierczyk, Herne (DE); Robert Franke, Marl (DE); Matthias Beller, Ostseebad Nienhagen (DE); Ricarda Dühren, Rostock (DE); and Ralf Jackstell, Rostock (DE)
Assigned to EVONIK OPERATIONS GMBH, Essen (DE)
Filed by EVONIK OPERATIONS GMBH, Essen (DE)
Filed on Nov. 19, 2021, as Appl. No. 17/530,629.
Claims priority of application No. 20209161 (EP), filed on Nov. 23, 2020.
Prior Publication US 2022/0162147 A1, May 26, 2022
Int. Cl. C07C 67/04 (2006.01); C07C 67/36 (2006.01); C07C 67/38 (2006.01); B01J 31/22 (2006.01)
CPC C07C 67/04 (2013.01) [B01J 31/2234 (2013.01); C07C 67/36 (2013.01); C07C 67/38 (2013.01); B01J 2231/321 (2013.01); B01J 2231/645 (2013.01); B01J 2531/821 (2013.01)] 15 Claims
 
1. A process comprising the process steps of:
a) initially charging an ethylenically unsaturated compound;
b) adding a ligand of formula (I):

OG Complex Work Unit Chemistry
wherein
R1, R2 and R3 are selected from the group consisting of —(C1-C12)-alkyl, —(C6-C12)-cycloalkyl and —(C6-C20)-aryl,
wherein the —(C6-C12)-cycloalkyl radical and the —(C6-C20)-aryl radical may have substituents which are selected from the group consisting off —(C1-C12)-alkyl, —O—(C1-C12)-alkyl and —SO3Na;
and a compound comprising Ru;
c) adding an acid (II) having the formula (IIa) or (IIb):

OG Complex Work Unit Chemistry
wherein R4 is —(C1-C18)-alkyl;

OG Complex Work Unit Chemistry
wherein R5 is —(C1-C18)-alkyl;
d1) feeding in CO;
e) heating a mixture formed from a) to d1) to convert the ethylenically unsaturated compound directly into an ester or diester of acid (II) without isolation of intermediates.