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

Patent metadata

Field	Value
Publication number	US-11655266-B2
Application number	US-202117544254-A
Country	US
Kind code	B2
Filing date	Dec 7, 2021
Priority date	Dec 9, 2020
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

Platinum complexes having binaphthyldiphosphine ligands for the catalysis of the hydroxycarbonylation of ethylenically unsaturated compounds.

First claim

The invention claimed is:

1. Complex comprising Pt and a compound of formula (I)

where
R 1 , R 2 , R 3 , R 4 are each independently selected from —(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-heteroaryl.

2. Complex according to claim 1 ,
wherein at least two of the R 1 , R 2 , R 3 , R 4 radicals are a —(C 6 -C 20 )-heteroaryl radical having at least six ring atoms.

3. Complex according to claim 1 ,
wherein the R 1 and R 3 radicals are each a —(C 6 -C 20 )-heteroaryl radical having at least six ring atoms.

4. Complex according to claim 1 ,
wherein the R 1 and R 3 radicals are each 2-pyridyl.

5. Complex according to claim 1 ,
wherein R 2 and R 4 are —(C 1 -C 12 )-alkyl.

6. Complex according to claim 1 ,
wherein R 2 and R 4 are tert-butyl.

7. Complex according to claim 1 ,
wherein the compound (I) has the structure (1):

8. Process comprising the process steps of:
a) initially charging an ethylenically unsaturated compound;
b) adding a complex according to claim 1 , or
a compound of formula (I)

where
R 1 , R 2 , R 3 , R 4 are each independently selected from —(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-heteroaryl
and
a substance comprising Pt;
c) adding an acid;
d) feeding in CO;
e) heating the reaction mixture from a) to d), with conversion of the ethylenically unsaturated compound to a carboxylic acid.

9. Process according to claim 8 ,
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.

10. Process according to claim 8 ,
wherein the acid in process step c) is selected from: acetic acid, perchloric acid, sulfuric acid, phosphoric acid, methylphosphonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, tert-butanesulfonic acid, p-toluenesulfonic acid (PTSA), 2-hydroxypropane-2-sulfonic acid, 2,4,6-trimethylbenzenesulfonic acid, dodecylsulfonic acid, camphorsulfonic acid.

11. Process according to claim 8 ,
wherein the acid in process step c) is acetic acid.

12. Process according to claim 8 ,
wherein the substance comprising Pt 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 ], (cinnamyl)platinum dichloride [Pt(cinnamyl)Cl 2 ].

13. Process according to claim 8 ,
wherein the substance comprising Pt is selected from: platinum dichloride (PtCl 2 ), platinum(II) acetylacetonate [Pt(acac) 2 ], platinum(II) acetate [Pt(OAc) 2 ].

Assignees

• Evonik Operations Gmbh

Inventors

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

Classifications

• B01J2531/0213

  Complexes without C-metal linkages · CPC title

• C07F15/0093 Primary

  without a metal-carbon linkage · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• B01J31/24

  Phosphines {, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands} · CPC title

• B01J31/2409

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