Homogeneous catalysts that are recoverable by host-guest interactions

Patent metadata

Field	Value
Publication number	US-10828628-B2
Application number	US-201916433929-A
Country	US
Kind code	B2
Filing date	Jun 6, 2019
Priority date	Aug 22, 2016
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

A method for separating a homogeneous catalyst from a solution includes forming a host-guest compound between a first isomer of the catalyst and inclusion compound in the solution and isolating the host-guest compound from the solution. The catalyst may be released from the inclusion compound by converting the first isomer of the catalyst to a second isomer of the catalyst.

First claim

That which is claimed is:

1. A method of performing a catalyzed chemical reaction, the method comprising:
catalyzing a chemical reaction in a solution using an azobenzene-modified Grubbs homogeneous catalyst;
adding a host compound to the solution, the host compound binding a first isomer of the catalyst to form a host-guest compound including the host compound and first isomer of the catalyst, the host compound being a cyclodextrin;
isolating the host-guest compound from the solution; and
releasing the catalyst from the host-guest compound by converting the first isomer of the catalyst to a second isomer of the catalyst.

2. The method of claim 1 , wherein first isomer is a cis or trans isomer and the second isomer is the other of a cis or trans isomer.

3. The method of claim 1 , wherein the homogeneous catalyst includes a transition metal and an N-heterocyclic carbene moiety bonded to an azobenzene moiety.

4. The method of claim 1 , wherein the cyclodextrin attached to a surface of a substrate.

5. The method of claim 1 , wherein the chemical reaction is an olefin metathesis reaction.

6. The method of claim 1 , wherein converting the first isomer of the catalyst to a second isomer of the catalyst includes applying electromagnetic radiation.

7. The method of claim 1 , wherein:
the catalyst is converted from the first isomer to the second isomer by applying electromagnetic radiation that causes the azobenzene functional group to undergo an isomerization change.

8. A composition comprising a homogeneous catalyst including a transition metal complex having an N-heterocyclic carbene ligand with an azobenzene functional group thereon, the azobenzene functional group being effective to undergo cis-trans isomerization;
the composition having the formula

where R indicates the position of the azobenzene functional group.

9. The composition of claim 8 , further comprising a cyclodextrin moiety bound to the azobenzene functional group.

10. The composition of claim 9 , further comprising a silica substrate attached to the cyclodextrin moiety.

11. The method of claim 1 , wherein the homogeneous catalysts has the formula

12. The composition of claim 8 , wherein the homogeneous catalysts has the formula

Assignees

• Univ Florida State Res Found

Inventors

• Chung Hoyong

Classifications

• B01J31/2278 Primary

  Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts · CPC title

• C07C29/46

  by diene-synthesis · CPC title

• C07D207/20

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07C41/30

  by increasing the number of carbon atoms, e.g. by oligomerisation · CPC title

• B01J31/123

  Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain (B01J31/064, B01J31/066, B01J31/067, B01J31/08 and B01J31/10 take precedence; polymer-bound organometallic complexes B01J31/165; coordination polymers B01J31/1691; catalysts for the preparation of polysiloxanes, e.g. Karstedt catalysts C08G77/08) · CPC title