Dendritic macromolecules for metal-ligand catalyzed processes

• US 6,525,143 B2
• Filed: 11/16/2001
• Issued: 02/25/2003
• Est. Priority Date: 10/27/2000
• Status: Active Grant

• Current Assignee: Dow Technology Investments LLC (Dow, Inc.)
• Original Assignee: Union Carbide Chemicals & Plastics Technology Corporation (Dow, Inc.)
• Inventors: Miller, David James, Tulchinsky, Michael Leo
• Primary Examiner(s): Seidleck, James J.
• Assistant Examiner(s): Asinovsky, Olga
• Application Number:
  US09/991,572
• Publication Number:
  US 20020111438A1
• Time in Patent Office: 466 Days
• Field of Search: 525/330.4, 528/167, 502/162, 568/8, 568/454
• US Class Current: 525/330.4
• CPC Class Codes: C07C 45/50 by oxo-reactions
• CPC Class Codes: C07C 47/02 Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
• CPC Class Codes: C07F 9/65744 condensed with carbocyclic or heterocyclic rings or ring systems
• CPC Class Codes: C07F 9/65746 the molecule containing more than one cyclic phosphorus atom
• CPC Class Codes: C08G 79/04 Phosphorus linked to oxygen or to oxygen and carbon
• CPC Class Codes: C08G 83/003 Dendrimers
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

This invention relates to dendritic macromolecules and their use in metal-dendritic macroligand complex catalyzed processes, e.g., hydroformylation. The use of metal-dendritic macroligand complex catalysts in such processes facilitates the separation of desired product from catalyst, for example, by membrane filtration.

Claims

1. A metal-dendritic macroligand complex catalyst comprising a Group 8, 9 or 10 metal complexed with a dendritic macroligand represented by the formula:

wherein A represents a q-valent dendritic macromolecule radical, each B is the same or different and represents a substituted or unsubstituted r-valent organic or inorganic radical, each Y is the same or different and represents a substituted or unsubstituted monovalent hydrocarbon radical containing from 6 to 40 carbon atoms or each adjacent Y may be bridged together to form a substituted or unsubstituted cyclic hydrocarbon radical, m is a value of from 1 to about 3, n is a value of from 1 to about 1000, q equals n, and r equals m+1.

2. A process for producing one or more products comprising reacting one or more reactants in the presence of a metal-dendritic macroligand complex catalyst to produce said one or more products, in which said metal-dendritic macroligand complex catalyst comprises a Group 8, 9 or 10 metal complexed with a dendritic macroligand represented by the formula:

wherein A represents a q-valent dendritic macromolecule radical, each B is the same or different and represents a substituted or unsubstituted r-valent organic or inorganic radical, each Y is the same or different and represents a substituted or unsubstituted monovalent hydrocarbon radical containing from 6 to 40 carbon atoms or each adjacent Y may be bridged together to form a substituted or unsubstituted cyclic hydrocarbon radical, m is a value of from 1 to about 3, n is a value of from 1 to about 1000, q equals n, and r equals m+1.

4. The process of claim 2 which comprises a hydroformylation, hydroacylation (intramolecular and intermolecular), hydrocyanation, hydroamidation, hydroesterification, amination (hydro-amino-addition), alcoholysis (hydro-alkoxy-addition), hydrocarbonylation, hydroxycarbonylation, carbonylation, isomerization or transfer hydrogenation process.

5. The process of claim 2 wherein said metal-dendritic macroligand complex catalyst comprises rhodium complexed with a dendritic macroligand represented by the formula selected from:

3. A process for producing one or more products comprising (i) reacting one or more reactants in the presence of a metal-dendritic macroligand complex catalyst to produce said one or more products, and (ii) separating said metal-dendritic macroligand complex catalyst from said one or more products, wherein said metal-dendritic macroligand complex catalyst comprises a Group 8, 9 or 10 metal complexed with a dendritic macroligand represented by the formula:

wherein A represents a q-valent dendritic macromolecule radical, each B is the same or different and represents a substituted or unsubstituted r-valent organic or inorganic radical, each Y is the same or different and represents a substituted or unsubstituted monovalent hydrocarbon radical containing from 6 to 40 carbon atoms or each adjacent Y may be bridged together to form a substituted or unsubstituted cyclic hydrocarbon radical, m is a value of from 1 to about 3, n is a value of from 1 to about 1000, q equals n, and r equals m+4.

6. The process of claim 3 in which the separating step is effected by membrane filtration, dialysis, precipitation or centrifugation.

7. A functional organophosphite of the formula:

wherein G represents a functional organic or inorganic group which is capable of reacting with an end group of a dendrimer, E represents a substituted or unsubstituted divalent organic or inorganic radical, F represents a substituted or unsubstituted r-valent organic or inorganic radical, each Y is the same or different and represents a substituted or unsubstituted monovalent hydrocarbon radical containing from 6 to 40 carbon atoms or each adjacent Y may be bridged together to form a substituted or unsubstituted cyclic