IP Library Granted Patent US 9,688,604
Granted Patent B2
US 9,688,604 · App. 15/213,435 · Granted Jun 27, 2017

Phosphine ligand and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds

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Quick Facts
Patent No.
US 9,688,604
App. No.
15/213,435
Granted
Jun 27, 2017
Kind
B2
Abstract

The invention relates to a compound of formula (1) The invention further relates to Pd complexes comprising the compound according to the invention and to the use thereof in alkoxycarbonylation.

Claims (19)

1. Process comprising the following process steps:

a) initially charging an ethylenically unsaturated compound;

b) adding a compound of formula (1)

 and a compound comprising Pd,

 or adding a complex comprising Pd and the compound of formula (1);

c) adding an alcohol;

d) feeding in CO;

e) heating the reaction mixture, with conversion of the ethylenically unsaturated compound to an ester.

2. The process of claim 1 , wherein the complex is selected from one of the following K1 to K3:

3. Process according to claim 1 ,

wherein the ethylenically unsaturated compound is selected from ethene, propene, 1-butene, cis- and/or trans-2-butene, isobutene, 1,3-butadiene, 1-pentene, cis- and/or trans-2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, hexene, tetramethylethylene, heptene, 1-octene, 2-octene, di-n-butene, or mixtures thereof.

4. Process according to claim 1 ,

wherein the ethylenically unsaturated compound comprises 8 to 22 carbon atoms.

5. Process according to claim 1 ,

wherein the compound comprising Pd in process step b) is selected from palladium dichloride, palladium(II) acetylacetonate, palladium(II) acetate, dichloro(1,5-cyclooctadiene)palladium(II), bis(dibenzylideneacetone)palladium, bis(acetonitrile)dichloropailadium(II), palladium(cinnamyl) dichloride.

6. Process according to claim 1 ,

wherein the alcohol in process step c) is selected from methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol, or mixtures thereof.

7. A process for catalysis of an alkoxycarbonylation reaction, comprising: introducing a compound of formula (1)

 or a complex comprising Pd and the compound of formula (1).

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2024
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 066242/0585 →
CHANGE OF NAME Recorded Mar 29, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052254/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 19, 2017
From: JENNERJAHN, REIKO; GULAK, SAMET, DR.; FANG, XIANGJIE, DR.; DONG, KAIWU, DR.; NEUMANN, HELFRIED, DR.; JACKSTELL, RALF, DR.; BELLER, MATTHIAS, DR.; FRANKE, ROBERT, DR.; HESS, DIETER, DR.; DYBALLA, KATRIN MARIE, DR.; FRIDAG, DIRK; GEILEN, FRANK, DR.
To: EVONIK DEGUSSA GMBH
Reel/Frame 042504/0072 →