# US 2010/0099550 A1 · Homogeneous Process for the Hydrogenation of Carboxylic Acids and Derivatives Thereof

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- Number: US 2010/0099550 A1
- Document ID: US20100099550A1
- Status: Published application
- Kind: A1
- Application number: 12/546,187
- Filed: 2009-08-24
- Published: 2010-04-22
- Earliest claimed: 2002-05-02
- Assignees: Davy Process Technology Limited
- Inventors: Melvyn Kilner; Derek Vincent Tyers; Simon Peter Crabtree; Michael Anthony Wood
- Web page: https://patentgrep.com/patent/US20100099550A1

## CPC

- B01J 31/2409: {with more than one complexing phosphine-P atom}
- B01J 31/24: 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}
- B01J 31/4023: {containing iron group metals, noble metals or copper}
- B01J 31/4046: {containing rhodium}
- B01J 31/4053: {with recovery of phosphorous catalyst system constituents}
- C07C 27/04: by reduction of oxygen-containing compounds (C07C29/14 takes precedence)
- C07C 29/149: with hydrogen or hydrogen-containing gases
- B01J 2231/641: Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J 2531/0258: Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane
- B01J 2531/821: Ruthenium
- B01J 2531/822: Rhodium
- B01J 2531/824: Palladium
- B01J 2531/825: Osmium
- B01J 2531/842: Iron
- B01J 2531/96: Water
- Y02P 20/52: using catalysts, e.g. selective catalysts
- Y02P 20/584: Recycling of catalysts
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A homogenous process for the hydrogenation of the carboxylic acids and/or derivatives thereof in the presence of a catalyst comprising ruthenium, rhodium, iron, osmium or palladium, and an organic phosphine is described in which the hydrogenation is carried out in the presence of at least about 1% by weight water. A process for regenerating a catalyst comprising ruthenium, rhodium, iron, osmium or palladium and an organic phosphine is also described in which the regeneration is carried out in the presence of hydrogen and water.

## Claims

### Claim 1

A homogeneous process for the hydrogenation of carboxylic acids and/or derivatives thereof in the presence of a catalyst comprising:
(a) ruthenium, rhodium, iron, osmium or palladium; and
(b) an organic phosphine;
wherein the hydrogenation is carried out in the presence of more than 1% by weight water.

### Claim 2 (depends on 1)

A homogeneous process according to claim 1 wherein the carboxylic acids and/or derivatives thereof are present as solvent.

### Claim 3 (depends on 1)

A homogeneous process according to claim 1 wherein a solvent is present and the water is present as an additive therein.

### Claim 4 (depends on 3)

A homogeneous process according to claim 3 wherein the water is present in an amount of more than 1% to the solubility limit of the water in the solvent.

### Claim 5 (depends on 3)

A homogeneous process according to claim 3 wherein the water is present in an amount greater than the solubility limit of the water in the solvent and the excess water forms an aqueous phase.

### Claim 6 (depends on 1)

A homogeneous process according to claim 1 wherein water is generated in situ.

### Claim 7 (depends on 2)

A homogeneous process according to claim 2 wherein the product of the reaction forms the solvent.

### Claim 8 (depends on 1)

A homogeneous process according to claim 1 wherein the water is a solvent for the reaction.

### Claim 9 (depends on 1)

A homogeneous process according to claim 1 wherein the catalyst is a ruthenium/phosphine catalyst system

### Claim 10 (depends on 9)

A homogeneous process according to claim 9 wherein the phosphine component of the catalyst system is a tridentate phosphine.

### Claim 11 (depends on 9)

A homogeneous process according to claim 9 wherein the phosphine component of the catalyst system is tris-1,1,1-(diphenyl-phosphinomethyl)ethane.

### Claim 12 (depends on 1)

A homogeneous process according to claim 1 wherein the reaction is carried out in the absence of a promotor for the catalyst.

### Claim 13 (depends on 1)

A homogeneous process according to claim 1 wherein the reaction is carried out in the absence of halide.

### Claim 14 (depends on 1)

A homogeneous process according to claim 1 wherein the reaction temperature is in the range of from about 150° C. to about 350° C.

### Claim 15 (depends on 1)

A homogeneous process according to claim 1 wherein the reaction pressure is in the range of from about 250 psig to about 2000 psig.

### Claim 16 (depends on 10)

A homogeneous process according to claim 10 wherein the pressure is from about 800 psig to about 1200 psig.

### Claim 17 (depends on 1)

A homogeneous process according to claim 1 wherein the catalyst is regenerated in the presence of the water and hydrogen.

### Claim 18

A process for regenerating a catalyst comprising:
(a) ruthenium, rhodium, iron, osmium or palladium; and
(b) an organic phosphine;
wherein the regeneration is carried out in the presence of hydrogen and water.

### Claim 19 (depends on 18)

A process according to claim 18 wherein the regeneration is carried out at a temperature of from about 150° C. to about 350° C.