Process for preparing electron deficient olefin precursors

Patent metadata

Field	Value
Publication number	US-10822303-B2
Application number	US-201916438531-A
Country	US
Kind code	B2
Filing date	Jun 12, 2019
Priority date	Dec 23, 2016
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

This invention relates to a process for producing electron deficient olefin precursors, such as 2-cyanoacetates, using an acid catalyzed transesterification reaction.

First claim

What is claimed is:

1. A process for the preparation of a cyanoacetate, steps of which comprise:
(a) reacting an ester of cyanoacetic acid and an alcohol, in the presence of a catalyst comprising a lanthanide element, wherein the lanthanide element comprises ytterbium, under appropriate conditions and for a time sufficient to yield a cyanoacetate;

wherein the alcohol is present in an amount of from about 0.5 to about 2.0 equivalents relative to the ester of the cyanoacetic acid; and wherein the catalyst is present in an amount of up to about 20 mol %;
(b) optionally, separating the so-formed cyanoacetate from the reaction mixture to be substantially free from the ester of cyanoacetic acid the alcohol and/or the catalyst, and by-products.

2. The process of claim 1 , wherein the catalyst comprising a lanthanide element has one or more ligands bound to the element(s).

3. The process of claim 2 , wherein the one or more ligands is selected from halogens, triflates, mesylates, nitrates or tosylates.

4. The process of claim 1 , wherein the alcohol is any mono-, di- or multi-functional hydroxyl compound.

5. The process of claim 1 , wherein the alcohol is any mono-, di- or multi-functional C 1-20 alkanol, C 2-20 alkenol, or C 2-20 alkynol.

6. The process of claim 1 , wherein the alcohol is an aromatic alcohol.

7. The process of claim 1 , wherein the alcohol is phenol, benzyl alcohol or derivatives thereof.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Duffy Cormac
• Phelan Marisa
• Burns Barry

Classifications

• B01J31/2256

  being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional ligands · CPC title

• B01J21/066

  Zirconium or hafnium; Oxides or hydroxides thereof · CPC title

• C07C255/23

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton · CPC title

• B01J23/20

  Vanadium, niobium or tantalum · CPC title

• B01J2531/38

  Lanthanides other than lanthanum · CPC title