Methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in hydroformylation processes

Patent metadata

Field	Value
Publication number	US-2021114961-A1
Application number	US-201917040287-A
Country	US
Kind code	A1
Filing date	May 3, 2019
Priority date	May 30, 2018
Publication date	Apr 22, 2021
Grant date	—

Abstract

The present invention relates to methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in a hydroformylation process. In one aspect, a method comprises (a) contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a tetraphosphine having the structure described herein, and, optionally, (C) a monophosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions; and (b) adding additional monophosphine having the structure described herein to a reaction zone.

First claim

1 . A method for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in a hydroformylation process, the method comprising:
(a) contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) 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, and, optionally, (C) a monophosphine having the following structure:

wherein P is a phosphorous atom, and each of Y 1 -Y 3 are independently an aryl group, an alkaryl group, a cycloalkyl group, a benzyl group, a C3 to C8 alkyl group, an alkoxyl group of 1-8 carbons, an aryloxy group, or a halogen, the contacting conducted in one or more reaction zones and at hydroformylation conditions; and
(b) adding additional monophosphine having the above structure to a reaction zone.

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

3 . The method of claim 1 , wherein the monophosphine is a bulky monophosphine.

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

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

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

7 . The method of claim 1 , wherein the decline in hydroformylation rate over time is less than in a process under identical conditions, with the exception of the absence of monophosphine.

8 . The method of claim 1 , wherein the rate of tetraphosphine ligand usage in the hydroformylation process is less than in a hydroformylation process under identical conditions, with the exception of the absence of monophosphine.

9 . The method of claim 1 , wherein the amount of monophosphine added is at least 40 moles of phosphine per mole of transition metal.

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

Assignees

• Dow Technology Investments Llc

Inventors

• Brammer Michael A
• Becker Michael C
• Felsted Ii William N

Classifications

• B01J2531/822

  Rhodium · CPC title

• B01J31/2409 Primary

  with more than one complexing phosphine-P atom · CPC title

• C07C45/50 Primary

  by oxo-reactions · 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

• C07C45/505 Primary

  Asymmetric hydroformylation · CPC title