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Immobilized lewis acid catalysts coated with ionic liquids and use thereof

Foreign code F110003813
File No. E07613WO
Posted date Jul 5, 2011
Country United States of America
Application number 28244407
Gazette No. 20090318729
Gazette No. 8871668
Date of filing Mar 12, 2007
Gazette Date Dec 24, 2009
Gazette Date Oct 28, 2014
International application number JP2007054770
International publication number WO2007105668
Date of international filing Mar 12, 2007
Date of international publication Sep 20, 2007
Priority data
  • P2006-066030 (Mar 10, 2006) JP
  • 2007WO-JP54770 (Mar 12, 2007) WO
Title Immobilized lewis acid catalysts coated with ionic liquids and use thereof
Abstract (US8871668)
The invention provides a novel immobilized Lewis acid catalyst which exhibits high catalytic activity in an aqueous solution and which permits recovery and reuse or long-term continuous use.
The invention relates to an immobilized Lewis acid catalyst comprising a solid substance and a Lewis acid supported on the surface of the solid substance by chemical bonding, wherein the surface of the solid substance and the peripheries of the Lewis acid are coated with an ionic liquid, more specifically, an immobilized Lewis acid catalyst comprising a solid substance such as silica gel or an organic polymer and a Lewis acid stable even in water which is supported on the surface of the solid substance by chemical bonding, wherein the surface of the solid substance and the peripheries of the Lewis acid are completely or partially coated with a hydrophobic ionic liquid; a process for the production of the catalyst; use thereof; and a process for the preparation of compounds with the catalyst.
Scope of claims [claim1]
1. An immobilized Lewis acid catalyst, comprising: a Lewis acid supported on the surface of a solid substance by chemical bonding, and
an ionic liquid comprising a cation and an anion, the ionic liquid coating the surface of the solid substance and the peripheries of the Lewis acid without being covalently-immobilized on the surface of the solid substance and the peripheries of the Lewis acid,
wherein the Lewin acid is a rare earth metal of bismuth salt, and
wherein the Lewin acid is chemically bound to a sulfonic acid group or sulfonamide group that is directly bound to the surface of the solid substance or is bound to the surface of the solid substance through a low molecular weight organic compound.
[claim2]
2. The immobilized Lewis acid catalyst according to claim 1, wherein the ionic liquid is a hydrophobic ionic liquid.
[claim3]
3. The immobilized Lewis acid catalyst according to claim 1, wherein the ionic liquid is an ionic liquid containing any of imidazolium, pyridinium, quaternary ammonium and quaternary phosphonium, as the cation.
[claim4]
4. The immobilized Lewis acid catalyst according to claim 1, wherein the ionic liquid is an ionic liquid containing any of a halide ion, trifluoromethanesulfonate, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate and bis(trifluoromethanesulfonamide) ions, as the anion.
[claim5]
5. The immobilized Lewis acid catalyst according to claim 1, wherein the ionic liquid is an imidazolium salt.
[claim6]
6. The immobilized Lewis acid catalyst according to claim 1, wherein the ionic liquid is an imidazolium salt, and is an ionic liquid in which a hydrocarbon group having 6 or more carbon atoms is bound to at least one of the two nitrogen atoms present in the imidazole ring of the imidazolium salt.
[claim7]
7. The immobilized Lewis acid catalyst according to claim 1, wherein the Lewis acid is a trifluoromethanesulfonic acid salt of a rare earth metal, or a trifluoromethanesulfonic acid salt of bismuth.
[claim8]
8. The immobilized Lewis acid catalyst according to claim 7, wherein the rare earth metal is any of scandium, yttrium and ytterbium.
[claim9]
9. The immobilized Lewis acid catalyst according to claim 1, wherein the solid substance supporting the Lewis acid on the surface is any of a metal oxide, activated carbon, a synthetic organic polymer and glass.
[claim10]
10. The immobilized Lewis acid catalyst according to claim 1, wherein the solid substance supporting the Lewis acid on the surface is any of silica gel, crosslinked polystyrene, crosslinked polyethylene and crosslinked perfluoropolyethylene.
[claim11]
11. The immobilized Lewis acid catalyst according to claim 1, wherein the solid substance supporting the Lewis acid on the surface is silica gel.
[claim12]
12. The immobilized Lewis acid catalyst according to claim 1, wherein the solid supporting the Lewis acid on the surface is silica gel, the silica gel is bound to the low molecular weight organic compound through a siloxane bond (Si -- O -- Si), the low molecular weight organic compound further has a sulfonic acid group, and the Lewis acid is chemically bound to the sulfonic acid group.
[claim13]
13. A method for producing an immobilized Lewis acid coated with an ionic liquid, the method comprising: supporting and immobilizing a Lewis acid on the surface of a solid substance by chemical bonding via a sulfonic acid group or sufonamide group that is directly bound to the surface of the solid substance or bound to the surface of the solid substance through a low molecular weight organic coumpound, then
mixing the supported and immobilized Lewis acid with a solution of a hydrophobic ionic liquid dissolved in an organic solvent to form a liquid phase on the surface of the solid substance and on the peripheries of the Lewis acid, the liquid phase comprising the hydrophobic ionic liquid which is not covalently-immobilized on the surface of the solid substance and on the peripheries of the Lewis acid, the hydrophobic ionic liquid comprising a cation and an anion, and then
removing the organic solvent,
wherein the Lewis acid is a rare earth metal salt or a bismuth salt.
[claim14]
14. The method according to claim 13, wherein the Lewis acid is a trifluoromethanesulfonic acid salt of a rare earth metal, or a trifluoromethanesulfonic acid salt of bismuth.
[claim15]
15. A method for producing a chemical substance by a Lewis acid-catalyzed chemical reaction performed in water or a water-containing organic solvent, in the presence of the immobilized Lewis acid catalyst according to claim 1.
[claim16]
16. The method according to claim 15, wherein the Lewis acid-catalyzed chemical reaction performed in water or a water-containing organic solvent is any chemical reaction selected from the group consisting of an aldol reaction, a Mannich type reaction, a Diels-Alder reaction, an allylation reaction and a Michael reaction.
  • Inventor, and Inventor/Applicant
  • KOBAYASHI SHU
  • MORI YUICHIRO
  • YANLONG GU
  • 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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