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

Patent metadata

Field	Value
Publication number	US-9688604-B2
Application number	US-201615213435-A
Country	US
Kind code	B2
Filing date	Jul 19, 2016
Priority date	Jul 23, 2015
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

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.

First claim

The invention claimed is:

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).

Assignees

• Evonik Degussa Gmbh

Inventors

• Jennerjahn Reiko
• Gülak Samet
• Fang Xiangjie
• Dong Kaiwu
• Neumann Helfried
• Jackstell Ralf
• Beller Matthias
• Franke Robert
• Hess Dieter
• Dyballa Katrin Marie
• Fridag Dirk
• Geilen Frank

Classifications

• C07F9/58 Primary

  Pyridine rings · CPC title

• B01J31/2404

  Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring · CPC title

• C07F9/65515

  the oxygen atom being part of a five-membered ring · CPC title

• C07F9/5045

  Complexes or chelates of phosphines with metallic compounds or metals · CPC title

• B01J31/2409

  with more than one complexing phosphine-P atom · CPC title