Method for the preparation of a stabilized organophosphorous compound solution

Patent metadata

Field	Value
Publication number	US-10487020-B2
Application number	US-201615574322-A
Country	US
Kind code	B2
Filing date	Jul 5, 2016
Priority date	Jul 28, 2015
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions.

First claim

What is claimed is:

1. A process comprising: preparing a solution from raw materials comprising a solvent, an alkanolamine and a ligand raw material comprising a hydrolyzable organophosphorus ligand, wherein degradation by-products in the solution have a total acidity equivalent to at least 200 ppmw phosphorous acid, based on the weight of the ligand, wherein the concentration of alkanolamine in the solution is from 0.025 to 1 wt % based on the total weight of the solution, and wherein the solvent is an aromatic hydrocarbon, an ether, an ester, an aldehyde, and/or an alcohol.

2. The process of claim 1 wherein the ligand raw material is a solid ligand, and comprises greater than 200 ppmw phosphorous acid.

3. The process of claim 1 wherein the solvent comprises an alcohol and/or aldehyde.

4. The process of claim 1 wherein the concentration of the alkanolamine is from 0.2 to 0.7 wt % based on the total weight of the solution.

5. The process of claim 1 wherein the alkanolamine includes at least one compound selected from triethanolamine, triisopropanolamine, methyldiethanolamine, dimethylethanolamine and ethyldiethanolamine.

6. The process of claim 1 wherein the alkanolamine includes at least one compound selected from triethanolamine and triisopropanolamine.

7. The process of claim 1 wherein the alkanolamine is triethanolamine.

8. The process of claim 1 further comprising feeding the ligand solution to a hydroformylation process.

9. The process of claim 8 wherein the hydroformylation process comprises a reaction zone and an extraction zone, and wherein at least a portion of the solution is fed from a mix tank to the reaction zone and/or the extraction zone of the hydroformylation process.

10. The process of claim 8 wherein the solution is fed to the extraction zone.

11. The process of claim 8 wherein the hydroformylation process comprises contacting CO, H 2 , and at least one olefin under hydroformylation conditions sufficient to form at least one aldehyde product in the presence of a catalyst comprising, as components, a transition metal and the hydrolyzable ligand.

12. The process of claim 8 wherein the solution is stored for more than a day before being used in an end use application.

13. The process of claim 8 wherein the solution is stored for more than 3 days before being used in an end use application.

14. The process of claim 8 wherein the solution is stored for a period of at least 30 days before being used in an end use application.

15. The process of claim 1 wherein the solvent has a carboxylic acid content of from 0.02 to 1 weight percent, based on the weight of the solvent.

16. The process of claim 1 , wherein the solution is free of transition metals.

17. A process comprising: preparing a solution from raw materials comprising a solvent, an alkanolamine and a ligand raw material comprising a hydrolyzable organophosphorus ligand, wherein degradation by-products in the solution have a total acidity equivalent to at least 200 ppmw phosphorous acid, based on the weight of the ligand, wherein the concentration of alkanolamine in the solution is from 0.025 to 1 wt % based on the total weight of the solution, and wherein the solvent is xylene, toluene, an ether, an ester, an aldehyde, and/or an alcohol.

Assignees

• Dow Technology Investments Llc

Inventors

• Brammer Michael A
• Phillips George R
• Miller Glenn A
• Campbell Jr Donald L

Classifications

• C07B63/04 Primary

  Use of additives {(anti-oxidant compositions or compositions inhibiting chemical change in general C09K15/00)} · CPC title

• C07F9/65748

  the cyclic phosphorus atom belonging to more than one ring system · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• B01J31/185

  Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof · CPC title

• C07C215/10

  with one amino group and at least two hydroxy groups bound to the carbon skeleton · CPC title