# US 12,595,221 B1 · Hydroformylation processes

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- Number: US 12,595,221 B1
- Document ID: US12595221B1
- Status: Granted
- Kind: B1
- Application number: 18/261,417
- Filed: 2022-02-23
- Granted: 2026-04-07
- Earliest claimed: 2021-03-31
- Assignees: Dow Technology Investments LLC
- Applicants: Dow Technology Investments LLC
- Inventors: Jason F. Giles; Glenn A. Miller
- Web page: https://patentgrep.com/patent/US12595221B1

## CPC

- C07C 45/50: by oxo-reactions
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

This disclosure relates to continuous hydroformylation processes. In one aspect, a continuous hydroformylation process comprises: (a) contacting CO, H2, and at least one olefin in the presence of a hydroformylation catalyst in a reaction fluid in at least two reaction zones under hydroformylation conditions sufficient to form at least one aldehyde product, wherein the hydroformylation catalyst comprises a catalytic metal and a ligand and wherein a reaction temperature in the first reaction zone is controlled using a first heat exchanger; and (b) recovering at least a portion of the hydroformylation catalyst from a product stream and recycling at least a portion of the recovered hydroformylation catalyst through the first reaction zone. The heat evolution in the first reaction zone is reduced by reducing the reaction rate in the first reaction zone and increasing the reaction rate in a downstream reaction zone to insure sufficient heat removal capacity remains on the heat exchanger in the first reaction zone to insure stable control of the reaction at a target reaction temperature.

## Claims

### Claim 1

A continuous hydroformylation process comprising
(a) contacting CO, H2, and at least one olefin in the presence of a hydroformylation catalyst in a reaction fluid in at least two reaction zones under hydroformylation conditions sufficient to form at least one aldehyde product, wherein the hydroformylation catalyst comprises a catalytic metal and a ligand and wherein a reaction temperature in the first reaction zone is controlled using a first heat exchanger; and
(b) recovering at least a portion of the hydroformylation catalyst from a product stream and recycling at least a portion of the recovered hydroformylation catalyst through the first reaction zone;
wherein the heat evolution in the first reaction zone is reduced by reducing the reaction rate in the first reaction zone and increasing the reaction rate in a downstream reaction zone to insure sufficient heat removal capacity remains on the heat exchanger in the first reaction zone to insure stable control of the reaction at a target reaction temperature by: (1) diverting a portion of an olefin feed stream to a reaction zone downstream from the first reaction zone and changing the olefin partial pressure pressure in the first reaction zone by adjusting the amount of the olefin feed stream that is diverted; and/or (2) diverting a portion of the recycled hydroformylation catalyst to a reaction zone downstream from the first reaction zone and changing the concentration of the catalytic metal in the first reaction zone by adjusting the amount of the recycled hydroformylation catalyst that is diverted.

### Claim 2 (depends on 1)

The process of claim 1, wherein the reaction temperature in the first reaction zone is maintained within 1° C. of the target reaction temperature.

### Claim 3 (depends on 1)

The process of claim 1, further comprising measuring the olefin concentration in a headspace of the first reaction zone and adjusting the amount of the olefin feed stream diverted to the downstream reaction zone based on the measurement.

### Claim 4 (depends on 1)

The process of claim 1 wherein the reaction rate in the first reaction zone is greater than 1.5 gmoles aldehyde/liter reactor volume/hour.

### Claim 5 (depends on 1)

The process of claim 1 wherein the ligand is a hydrolyzlable organophosphorus ligand.

### Claim 6 (depends on 1)

The process of claim 1 wherein the catalytic metal is rhodium.

### Claim 7 (depends on 1)

The process of claim 1, wherein the reaction temperature is 100° C. or less.

### Claim 8 (depends on 1)

The process of claim 1 wherein at least one Advanced Process Control technique is employed to control the hydroformylation process.