# US 11,027,266 B2 · Phosphorous acid P,P′-[5,5′,6,6′-tetramethyl-3,3′-bis(l- methylethyl)[1,1′-biphenyl]-2,2′-diyl] P,P,P′,P'-tetrakis(2,4-dimethylphenyl) ester in hydroformylation

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- Number: US 11,027,266 B2
- Document ID: US11027266B2
- Status: Granted
- Kind: B2
- Application number: 15/805,372
- Filed: 2017-11-07
- Published: 2018-05-10
- Granted: 2021-06-08
- Earliest claimed: 2016-11-08
- Assignees: Evonik Operations GmbH
- Applicants: Evonik Degussa GmbH
- Inventors: Robert Franke
- Web page: https://patentgrep.com/patent/US11027266B2

## CPC

- B01J 31/0259: {comprising phosphorous acid (-ester) groups ((RO)P(OR')2) or the isomeric phosphonic acid (-ester) groups (R(R'O)2P=O), i.e. R= C, R'= C, H}
- B01J 31/28: of the platinum group metals, iron group metals or copper
- C07C 45/505: {Asymmetric hydroformylation}
- C07C 45/62: by hydrogenation of carbon-to-carbon double or triple bonds
- C07F 9/145: with hydroxyaryl compounds
- C07F 15/0006: {compounds of the platinum group}
- C07F 15/0073: {Rhodium compounds}
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The compound of the formula (1) and its complexes with metal cations are used for catalysis in hydroformylation processes.

## Claims

### Claim 1

A symmetric bidentate metal ligand complex mixture comprising a compound represented by formula (2):
and a metal atom selected from the group consisting of Rh, Ru, Co and Ir, wherein the symmetric bidentate metal ligand complex mixture has a chlorine value according to Wickhold below 10,000 ppm.

### Claim 2 (depends on 1)

The bidentate metal ligand complex mixture according to claim 1, wherein M is Rh.

### Claim 3 (depends on 1)

A process for converting an olefin to an aldehyde comprising the process steps of:
a1) initially charging an olefin having 2 to 24 carbon atoms,
b1) adding
the symmetric bidentate metal ligand complex mixture according to claim 1,
c1) feeding in H2 and CO,
d1) heating the reaction mixture, with conversion of the olefin to an aldehyde.

### Claim 4 (depends on 3)

The process according to claim 3, characterized in that the metal atom is Rh.

### Claim 5 (depends on 3)

The process according to claim 3, wherein the olefin having 2 to 24 carbon atoms is selected from ethene, propene butene, 1-butene or 2-butene.

### Claim 6 (depends on 3)

The process according to claim 3, characterized in that, in step a1), wherein the olefin having 2 to 24 carbon atoms is selected from 1-butene or 2-butene.

### Claim 7 (depends on 1)

A catalytic hydroformylation process comprising contacting an olefin with
the symmetric bidentate metal ligand complex mixture according to claim 1.

### Claim 8 (depends on 7)

The process according to claim 7, wherein the hydroformylation process converts the olefin to substituted or unsubstituted aldehydes having 3 to 20 carbon atoms, including substituted or unsubstituted propenals, butanals, pentanals, nonanals, tridecanals, substituted or unsubstituted propenals, butanals or pentanals.

### Claim 9 (depends on 7)

The process according to claim 7, wherein the substituted or unsubstituted aldehydes having 3 to 20 carbon atoms include substituted or unsubstituted propenals, butanals or pentanals.