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Polymer incarcerated Lewis acid metal catalyst achieved

Foreign code F110003808
File No. E07607WO
Posted date Jul 5, 2011
Country United States of America
Application number 59182905
Gazette No. 20070191624
Gazette No. 7470646
Date of filing Mar 8, 2005
Gazette Date Aug 16, 2007
Gazette Date Dec 30, 2008
International application number JP2005003949
International publication number WO2005084802
Date of international filing Mar 8, 2005
Date of international publication Sep 15, 2005
Priority data
  • P2004-065250 (Mar 9, 2004) JP
  • 2005WO-JP03949 (Mar 8, 2005) WO
Title Polymer incarcerated Lewis acid metal catalyst achieved
Abstract (US7470646)
The objective is to incarcerate a Lewis acid metal in a polymer and to make this catalyst recoverable while maintaining its function as a Lewis acid metal catalyst.
The present invention is a polymer-incarcerated Lewis acid metal catalyst in which a Lewis acid metal is incarcerated in a crosslinked polymer and the crosslinked polymer is crosslinked using the crosslinking groups contained in a crosslinkable polymer.
The polymer incarcerated Lewis acid metal catalyst is characterized by the crosslinkable polymer containing at least one type of monomer unit containing hydrophobic substituents and hydrophilic substituents containing crosslinking groups, and the hydrophobic substituents contain aromatic substituents.
This crosslinkable polymer preferably comprises at least one type of monomer unit containing hydrophobic substituents and hydrophilic substituents containing crosslinking groups and a monomer unit containing hydrophobic substituents.
This catalyst can be obtained by subjecting a polymer micelle incarcerated Lewis acid metal obtained by mixing an organic solution containing a crosslinkable polymer and a Lewis acid metal with a bad solvent to a crosslinking reaction.
This catalyst is useful as a catalyst in aldol reactions, cyanolation reactions, allylation reactions, Michael reactions, Mannich reactions, Diels Alder reactions and Friedel Crafts reactions.
Scope of claims [claim1]
1. A polymer incarcerated Lewis acid metal catalyst comprising a Lewis acid metal incarcerated in a crosslinked polymer, wherein the crosslinked polymer is obtained by crosslinking a crosslinkable polymer which has hydrophilic substituents containing crosslinking groups linked directly to the crosslinkable polymer main chain and hydrophobic substituents linked directly to the crosslinkable polymer main chain, wherein the hydrophobic substituents do not contain hydrophilic groups or crosslinking groups, and further wherein the crosslinkable polymer contains at least one type of monomer unit containing (a) an aromatic hydrophobic substituent which does not contain hydrophilic groups or crosslinking groups and (b) a hydrophilic substituent containing a crosslinking group.
[claim2]
2. The catalyst of claim 1, wherein the crosslinkable polymer further contains at least one type of monomer unit containing a hydrophobic substituent but no hydrophilic substituent containing a crosslinking group.
[claim3]
3. The catalyst of claim 2, wherein the crosslinkable polymer further contains at least one type of a monomer unit containing a hydrophobic substituent other than an aromatic substituent and a hydrophilic substituent containing a crosslinking group but no hydrophilic substituent containing a crosslinking group.
[claim4]
4. The catalyst of claim 1, wherein the crosslinkable polymer contains a monomer unit containing a hydrophilic substituent containing an epoxy group and a monomer unit containing a hydrophilic substituent containing a group that reacts with the epoxy group.
[claim5]
5. The catalyst of claim 4, wherein the crosslinkable polymer contains a monomer unit containing an aromatic substituent and a hydrophilic substituent containing an epoxy group, a monomer unit containing an aromatic substituent and a hydrophilic substituent containing a group that reacts with the epoxy group, and a monomer unit containing a hydrophobic substituent but no hydrophilic substituent containing a crosslinking group.
[claim6]
6. The catalyst of claim 4, wherein the crosslinkable polymer contains a monomer unit containing an aromatic substituent and a hydrophilic substituent containing an epoxy group, a monomer unit containing a hydrophobic substituent other than an aromatic substituent and a hydrophilic substituent containing a group that reacts with the epoxy group and a monomer unit containing a hydrophobic substituent but no hydrophilic substituent containing a crosslinking group.
[claim7]
7. The catalyst of claim 4, wherein the crosslinkable polymer contains a monomer unit containing an aromatic substituent and a hydrophilic substituent containing a group that reacts with an epoxy group, a monomer unit containing a hydrophobic substituent other than an aromatic substituent and a hydrophilic substituent containing an epoxy group and a monomer unit containing a hydrophobic substituent but no hydrophilic substituent containing a crosslinking group.
[claim8]
8. The catalyst of claim 4, wherein the group that reacts with an epoxy group is at least one selected from a group comprising a hydroxyl group, an amino group, a thiol group and a carboxyl group.
[claim9]
9. The polymer incarcerated Lewis acid metal catalyst of claim 1, wherein the crosslinkable polymer is obtained by polymerizing, as main monomers, a styrene monomer, a vinyl monomer represented by the general formula
wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R2 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or an aryl group containing less than 14 carbon atoms, R3 represents an alkylene group having 1 to 6 carbon atoms, -- (CH2)n(OCH2CHR5)m -- , -- (CH2)n(OCH2CO.dbd.O)m -- or -- (CH2)n(COCH2)m -- , wherein R5 represents a hydrogen atom or a methyl group and n and m each independently represent integers 1 to 10, and R4 represents an epoxy group, and a vinyl monomer represented by the general formula
wherein R1 to R3 and n and m independently represent the same as above, and R4 represents at least one reactive group selected from a group comprising a hydroxyl group, an amino group, a thiol group and a carboxyl group.
[claim10]
10. The catalyst of claim 1 prepared by mixing an organic solution containing the crosslinkable polymer and the Lewis acid metal to prepare a polymer micelle incarcerating Lewis acid metal, and crosslinking the polymer micelle incarcerating Lewis acid metal.
[claim11]
11. The catalyst of claim 1, wherein the Lewis acid metal is represented by MYn, wherein M represents Cu, Zn, Fe, Sc or a lanthanoid element, Y represents a halogen atom, OAc, OCOCF3, ClO4, SbF6, PF6 or OSO2CF3 and n is 2 or 3.
[claim12]
12. An aldol, cyanolation, allylation, Michael, Mannich, Diels Alder or Friedel Craft reaction conducted in the presence of the catalyst of claim 1.
[claim13]
13. The catalyst of claim 2, wherein the crosslinkable polymer contains a monomer unit containing a hydrophilic substituent containing an epoxy group and a monomer unit containing a hydrophilic substituent containing a group that reacts with the epoxy group.
[claim14]
14. The catalyst of claim 3, wherein the crosslinkable polymer contains a monomer unit containing a hydrophilic substituent containing an epoxy group and a monomer unit containing a hydrophilic substituent containing a group that reacts with the epoxy group.
[claim15]
15. The catalyst of claim 9 prepared by mixing an organic solution containing the crosslinkable polymer and the Lewis acid metal to prepare a polymer micelle incarcerating Lewis acid metal, and crosslinking the polymer micelle incarcerating Lewis acid metal.
[claim16]
16. The catalyst of claim 9, wherein the Lewis acid metal is represented by MYn, wherein M represents Cu, Zn, Fe, Sc or a lanthanoid element, Y represents a halogen atom, OAc, OCOCF3, ClO4, SbF6, PF6 or OSO2CF3 and n is 2 or 3.
[claim17]
17. The catalyst of claim 10, wherein the Lewis acid metal is represented by MYn, wherein M represents Cu, Zn, Fe, Sc or a lanthanoid element, Y represents a halogen atom, OAc, OCOCF3, ClO4, SbF6, PF6 or OSO2CF3 and n is 2 or 3.
[claim18]
18. An aldol, cyanolation, allylation, Michael, Mannich, Diels Alder or Friedel Craft reaction conducted in the presence of the catalyst of claim 9.
[claim19]
19. An aldol, cyanolation, allylation, Michael, Mannich, Diels Alder or Friedel Craft reaction conducted in the presence of the catalyst of claim 10.
  • Inventor, and Inventor/Applicant
  • KOBAYASHI SHU
  • AKIYAMA RYO
  • KAWAI NOBUYUKI
  • TAKEUCHI MASAHIRO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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