Methods of controlling hydroformylation processes

Patent metadata

Field	Value
Publication number	US-11344869-B2
Application number	US-201917040305-A
Country	US
Kind code	B2
Filing date	May 3, 2019
Priority date	May 30, 2018
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

The present invention relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

First claim

What is claimed is:

1. A method of controlling a hydroformylation process for producing aldehydes, the process comprising contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the following structure:

wherein each P is a phosphorous atom, and each of R 1 -R 46 are independently hydrogen, a C1 to C8 alkyl group, an aryl group, an alkaryl group, or a halogen, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of:
(1) increasing the N:I ratio by adding additional tetraphosphine to a reaction zone;
(2) decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or
(3) increasing the N:I ratio by volatilization of the free monophosphine.

2. The method of claim 1 , wherein the monophosphine is triphenylphosphine.

3. The method of claim 1 , wherein the transition metal comprises rhodium.

4. The method of claim 1 , wherein each R 1 -R 46 are hydrogen.

5. The method of claim 1 , wherein the olefin is propylene.

6. The method of claim 1 , wherein the amount of monophosphine in the reaction zone is greater than or equal to 1.5 weight percent based on the total weight of reaction fluid in the reaction zone.

7. The method of claim 1 , wherein the amount of monophosphine in the reaction zone is from 1.5 to 13 weight percent based on the total weight of reaction fluid in the reaction zone.

8. The method of claim 1 , wherein the amount of tetraphosphine in the reaction zone is greater than or equal to 0.06 weight percent based on the total weight of reaction fluid in the reaction zone.

9. The method of claim 1 , wherein the amount of tetraphosphine in the reaction zone is from 0.1 to 9 weight percent based on the total weight of reaction fluid in the reaction zone.

Assignees

• Dow Technology Investments Llc

Inventors

• Brammer Michael A
• Qian Huifeng

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C17/16 Primary

  of hydroxyl groups · CPC title

• C07C29/147

  of carboxylic acids or derivatives thereof · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• B01J31/0267 Primary

  Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen · CPC title