# US 7,612,241 B1 · Hydroformylation process

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- Number: US 7,612,241 B1
- Document ID: US7612241B1
- Status: Granted
- Kind: B1
- Application number: 12/383,294
- Filed: 2009-03-23
- Granted: 2009-11-03
- Earliest claimed: 2009-03-23
- Assignees: Lyondell Chemical Technology, L.P.
- Inventors: Daniel F. White; Wilfred P. Shum; David John Cole-Hamilton
- Web page: https://patentgrep.com/patent/US7612241B1

## CPC

- C07C 29/141: with hydrogen or hydrogen-containing gases
- C07C 45/50: by oxo-reactions
- C12C 11/02: Pitching yeast
- B01J 2231/321: Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
- B01J 2531/0238: Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J 2531/822: Rhodium
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12C: BEER; PREPARATION OF BEER BY FERMENTATION (ageing or ripening by storing C12H1/22; methods for reducing the alcohol content after fermentation C12H3/00; methods for increasing the alcohol content after fermentation C12H6/00; venting devices for casks, barrels or the like C12L9/00); PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted 4,5-bis(di-n-alkylphosphino)xanthene. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.

## Claims

### Claim 1

A process to produce 4-hydroxybutyraldehyde comprising reacting allyl alcohol with carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted 4,5-bis(di-n-alkylphosphino)xanthene.

### Claim 2 (depends on 1)

The process of claim 1 wherein the 4,5-bis(di-n-alkylphosphino)xanthene is 9,9-dimethyl-4,5-bis(dimethylphosphino)xanthene.

### Claim 3 (depends on 1)

The process of claim 1 wherein the 4,5-bis(di-n-alkylphosphino)xanthene is 9,9-dimethyl-4,5-bis(diethylphosphino)xanthene.

### Claim 4 (depends on 1)

The process of claim 1 wherein the solvent is selected from the group consisting of C5-C20 aliphatic hydrocarbons, C6-C12 aromatic hydrocarbons, ethers, alcohols, and mixtures thereof.

### Claim 5 (depends on 1)

The process of claim 1 wherein the solvent is selected from the group consisting of toluene, cyclohexane, methyl t-butyl ether, and mixtures thereof.

### Claim 6 (depends on 1)

The process of claim 1 wherein the rhodium complex comprises rhodium and ligands selected from the group consisting of hydride, carbonyl, trialkyl or triaryl phosphines, diphosphines, cyclopentadienyls, 2,4-alkanedionates, and mixtures thereof.

### Claim 7 (depends on 1)

The process of claim 1 wherein the reaction is performed at a temperature within the range of about 45° C. to about 85° C. and a pressure within the range of about 30 to about 400 psig.

### Claim 8 (depends on 1)

The process of claim 1 wherein the catalyst system further comprises a monophosphine compound.

### Claim 9 (depends on 8)

The process of claim 8 wherein the monophosphine compound is triphenylphosphine.

### Claim 10 (depends on 1)

The process of claim 1 further comprising hydrogenating the 4-hydroxybutyraldehyde in the presence of a hydrogenation catalyst to form 1,4-butanediol.

### Claim 11 (depends on 10)

The process of claim 10 wherein the hydrogenation catalyst is a nickel catalyst.

### Claim 12

A catalyst system comprising a rhodium complex and a substituted or unsubstituted 4,5-bis(di-n-alkylphosphino)xanthene.

### Claim 13 (depends on 12)

The catalyst system of claim 12 wherein the 4,5-bis(di-n-alkylphosphino)xanthene is 9,9-dimethyl-4,5-bis(dimethylphosphino)xanthene.

### Claim 14 (depends on 12)

The catalyst system of claim 12 wherein the 4,5-bis(di-n-alkylphosphino)xanthene is 9,9-dimethyl-4,5-bis(diethylphosphino)xanthene.

### Claim 15 (depends on 12)

The catalyst system of claim 12 wherein the rhodium complex comprises rhodium and ligands selected from the group consisting of hydride, carbonyl, trialkyl or triaryl phosphines, diphosphines, cyclopentadienyls, 2,4-alkanedionates, and mixtures thereof.