Platinum complexes having ferrocene diphosphine ligands for catalysis of the hydroxycarbonylation of ethylenically unsaturated compounds

Patent metadata

Field	Value
Publication number	US-11925926-B2
Application number	US-202117544144-A
Country	US
Kind code	B2
Filing date	Dec 7, 2021
Priority date	Dec 9, 2020
Publication date	Mar 12, 2024
Grant date	Mar 12, 2024

Abstract

Platinum complexes having ferrocene-diphosphine ligands for catalysis of the hydroxycarbonylation of ethylenically unsaturated compounds.

First claim

The invention claimed is:

1. A process comprising:
a) adding an ethylenically unsaturated compound to form a reaction mixture;
b) adding to the reaction mixture a platinum complex having a ferrocene-diphosphine ligand of formula (I)

where
R 1 , R 2 , R, and R 4 are each independently selected from —(C 1 -C 12 )-alkyl, —(C 6 -C 20 )— or heteroaryl or
adding to the reaction mixture the ligand of formula (I) and a Pt compound;

c) adding to the reaction mixture an acid;
d) feeding into the reaction mixture CO;
e) heating the reaction mixture formed from a) to d), to convert the ethylenically unsaturated compound to a carboxylic acid.

2. The 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.

3. The process according to claim 1 ,
wherein the acid is selected from: acetic acid, perchloric acid, sulfuric acid, phosphoric acid, methylphosphonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, tert-butanesulfonic acid, p-toluenesulfonic acid, 2-hydroxypropane-2-sulfonic acid, 2,4,6-trimethylbenzenesulfonic acid, dodecylsulfonic acid or camphorsulfonic acid.

4. The process according to claim 1 ,
wherein the acid is acetic acid.

5. The process according to claim 1 ,
wherein the Pt compound is selected from: platinum dichloride (PtCl 2 ), platinum(II) acetylacetonate [Pt(acac) 2 ], platinum(II) acetate [Pt(OAc) 2 ], dichloro(1,5-cyclooctadiene)platinum(II) [Pt(cod) 2 Cl 2 ], bis(dibenzylideneacetone)platinum[Pt(dba) 2 ], bis(acetonitrile)dichloroplatinum(II) [Pt(CH 3 CN) 2 Cl 2 ] or (cinnamyl)platinum dichloride [Pt(cinnamyl)Cl 2 ].

6. The process according to claim 1 ,
wherein the Pt compound is selected from: platinum dichloride (PtCl 2 ), platinum(II) acetylacetonate [Pt(acac) 2 ] or platinum(II) acetate [Pt(OAc) 2 ].

7. The process according to claim 1 ,
wherein the R 1 and R 3 radicals are each 2-pyridyl.

8. The process according to claim 7 ,
wherein R 2 and R 3 are —(C 1 -C 12 )-alkyl.

9. The process according to claim 8 ,
wherein R 2 and R 4 are tert-butyl.

Assignees

• Evonik Operations Gmbh
• Evonik Oxeno Gmbh & Co Kg

Inventors

• Schneider Carolin
• Jackstell Ralf
• Beller Matthias
• Franke Robert

Classifications

• B01J31/1616 Primary

  Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts (catalysts comprising molecular sieves B01J29/00) · CPC title

• C07C51/00

  Preparation of carboxylic acids or their salts, halides or anhydrides (of acids by hydrolysis of oils, fats or waxes C11C) · CPC title

• C07C2531/22

  Organic complexes · CPC title

• C07F17/02 Primary

  of metals of Groups 8, 9 or 10 of the Periodic Table · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title