# US 2023/0406801 A1 · Processes to improve catalytic metal accountability in hydroformylation processes

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- Number: US 2023/0406801 A1
- Document ID: US20230406801A1
- Status: Published application
- Kind: A1
- Application number: 18/251,009
- Filed: 2021-11-18
- Published: 2023-12-21
- Earliest claimed: 2020-12-14
- Assignees: Dow Technology Investments LLC
- Applicants: Dow Technology Investments LLC
- Inventors: Michael A. Brammer; Jason F. Giles; Glenn A. Miller
- Web page: https://patentgrep.com/patent/US20230406801A1

## CPC

- C07C 45/50: by oxo-reactions
- C07C 45/505: {Asymmetric hydroformylation}
- B01J 31/185: {Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof}
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising C7-C20 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the feed rate of olefins to the reaction zone is greater than 100 kilograms/hour; providing the reaction fluid to a strip gas vaporizer to produce a product stream and a vaporizer tails stream; measuring the C7-C20 olefin content in the vaporizer tails stream; and adding a C7-C20 olefins stream comprising at least 50 weight percent C7-C20 olefins to the vaporizer tails stream to maintain the C7-C20 content in vaporizer tails stream above 2 percent by weight.

## Claims

### Claim 1

A process to improve rhodium accountability in a continuous liquid recycle hydroformylation process, the process comprising:
contacting in a reaction zone reactants comprising C7-C20 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the feed rate of olefins to the reaction zone is greater than 100 kilograms/hour;
providing the reaction fluid to a strip gas vaporizer to produce a product stream and a vaporizer tails stream;
measuring the C7-C20 olefin content in the vaporizer tails stream; and
adding a C7-C20 olefins stream comprising at least 50 weight percent C7-C20 olefins to the vaporizer tails stream to maintain the C7-C20 content in vaporizer tails stream above 2 percent by weight.

### Claim 2 (depends on 1)

The process of claim 1, wherein the stream comprising at least 50 weight percent C7-C20 olefins is added to the vaporizer tails stream by one or more of:
(a) adding the C7-C20 olefins stream to the vaporizer catchpot bottom liquid layer;
or
(b) adding C7-C20 olefins stream to the vaporizer tail cooler; or
(c) adding C7-C20 olefins stream immediately before the vaporizer bottoms pump; or
(d) adding C7-C20 olefins stream immediately after the vaporizer bottoms pump.

### Claim 3 (depends on 1)

The process of claim 1, further comprising removing olefins from the product stream and returning a portion of the removed olefins as part of the C7-C20
olefins stream added to the vaporizer tails stream.

### Claim 4 (depends on 3)

The process of claim 3, wherein a majority of the C7-C20 olefins in the C7-C20 olefins stream added to the vaporizer tails stream are removed olefins from the product stream.

### Claim 5 (depends on 1)

The process of claim 1, wherein a majority of the olefins contacted in the reaction zone are C8 olefins.

### Claim 6 (depends on 5)

The process of claim 5, wherein the product stream comprises isononyl aldehyde.

### Claim 7 (depends on 1)

The process of claim 1, wherein the solubility of the catalyst and catalyst components is increased by the addition of the C7-C20 olefins stream to the vaporizer tails stream.