Hydrophilic phosphorus ligand and method for separation and recovery of catalyst

Patent metadata

Field	Value
Publication number	US-11801504-B2
Application number	US-202217861268-A
Country	US
Kind code	B2
Filing date	Jul 11, 2022
Priority date	Dec 30, 2021
Publication date	Oct 31, 2023
Grant date	Oct 31, 2023

Abstract

Provided is a hydrophilic phosphorus ligand with the structure of formula 1.

X is

Y is

m is an integer from 1 to 20, A independently is *—O(CH 2 ) n— , n is an integer from 1 to 5, *— is a bond close to triphenylphosphine, and — is a bond away from triphenylphosphine.

First claim

What is claimed is:

1. A hydrophilic phosphorus ligand having a structure of formula 1,

wherein X is

Y is

m is an integer of 1 to 20, A is independently *—O(CH 2 ) n— , n is an integer of 1 to 5, *— is a bond close to triphenylphosphine, and — is a bond away from triphenylphosphine.

2. The hydrophilic phosphorus ligand according to claim 1 , wherein a weight average molecular weight of the hydrophilic phosphorus ligand is 500 g/mol to 50,000 g/mol.

3. A method for separation and recovery of catalyst, comprising:
providing a solution with two phases comprising a first layer of the solution and a second layer of the solution, wherein
the first layer of the solution comprises a metal catalyst and a hydrophilic phosphorus ligand according to claim 1 ; and
the second layer of the solution comprises a reactant,
carrying out a chemical reaction to transfer the metal catalyst and the hydrophilic phosphorus ligand from the first layer of the solution to the second layer of the solution, and to make the reactant to react in the presence of the metal catalyst and the hydrophilic phosphorus ligand to form a product in the second layer of the solution; and

carrying out a separation process by cooling down the solution to transfer the metal catalyst and the hydrophilic phosphorus ligand from the second layer of the solution to the first layer of the solution, the product remaining in the second layer of the solution.

4. The method for separation and recovery of catalyst according to claim 3 , wherein a weight average molecular weight of the hydrophilic phosphorus ligand is 500 g/mol to 50,000 g/mol.

5. The method for separation and recovery of catalyst according to claim 3 , wherein polarity of the first layer of the solution is greater than polarity of the second layer of the solution.

6. The method for separation and recovery of catalyst according to claim 5 , wherein the first layer of the solution comprises water, polyethylene glycol, polypropylene glycol, an alcohol compound having a carbon number less than or equal to 4 , or a combination thereof.

7. The method for separation and recovery of catalyst according to claim 5 , wherein the second layer of the solution comprises an organic solvent, and the organic solvent comprises alkanes, cycloalkanes, benzenes, solvents with polarity lower than water, or co-solvents composed thereof.

8. The method for separation and recovery of catalyst according to claim 3 , wherein carrying out the separation process further comprises adding an additional organic solvent.

9. The method for separation and recovery of catalyst according to claim 3 , wherein the catalyst comprises a rhodium catalyst.

10. The method for separation and recovery of catalyst according to claim 9 , wherein the rhodium catalyst comprises RhCl 3 .xH 2 O, dicarbonyl acetylacetone rhodium (I) (Rh(acac)(CO) 2 ), (RhCl(CO) 2 ) 2 , carbonyl rhodium (Rh 6 (CO) 16 or Rh 4 (CO) 12 ), or rhodium(III) nitrate (Rh(NO 3 ) 3 ).

11. The method for separation and recovery of catalyst according to claim 3 , wherein carrying out the chemical reaction comprises carrying out hydroformylation, the reactant comprises olefin, and the product comprises an aldehyde compound.

12. The method for separation and recovery of catalyst according to claim 11 , wherein the olefin comprises olefin having a single carbon-carbon double bond, or olefin having a plurality of carbon-carbon double bonds, and the olefin having the carbon-carbon double bonds comprises dicyclopentadiene, tricyclopentadiene, dicyclohexadiene or cyclohexene-1-carbaldehyde.

13. The method for separation and recovery of catalyst according to claim 11 , wherein the aldehyde compound comprises an aldehyde compound having a carbon number of 2 to 12.

14. The method for separation and recovery of catalyst according to claim 11 , wherein carrying out the hydroformylation comprises introduction of hydrogen and carbon monoxide.

15. The method for separation and recovery of catalyst according to claim 14 , wherein pressure of the introduction of hydrogen and carbon monoxide is between 0.5 MPa and 15 MPa.

16. The method for separation and recovery of catalyst according to claim 11 , wherein the hydroformylation is carried out at a temperature between 50° C. and 160° C.

17. The method for separation and recovery of catalyst according to claim 3 , wherein pressure range of carrying out the separation process is between normal pressure and 10 MPa.

18. The method for separation and recovery of catalyst according to claim 11 , wherein a temperature at which the separation process is carried out is lower than a temperature at which the hydroformylation is carried out.

Assignees

• Ind Tech Res Inst

Inventors

• Hsueh Mao-Lin
• Chen yi-zhen
• Shih Kuo-Chen

Classifications

• B01J38/62 Primary

  organic · CPC title

• B01J23/464

  Rhodium · CPC title

• B01J23/96

  of catalysts comprising metals, oxides or hydroxides of the noble metals · CPC title

• B01J38/02

  Heat treatment · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title