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US 2019/0292139 A1Published application
Process for preparing electron deficient olefins
AssigneeHenkel IP & Holding GmbH
InventorsCormac Duffy, Marisa Phelan, Barry Burns
Life of this patent
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Abstract
This invention relates to a process for preparing electron deficient olefins, such as 2-cyanoacrylates, using an acid catalyzed two-step process including a transesterification reaction followed by a Knoevenagel condensation reaction.
Claims26
A process for the preparation of a cyanoacrylate, steps of which comprise:
- (a) reacting the ester of cyanoacetic acid and an alcohol, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacetate different from the ester of cyanoacetic acid;
- (b) reacting the so-formed cyanoacetate from step (a) with a source of aldehyde, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacrylate;
- and
- (c) optionally, separating from the mixture the so-formed cyanoacrylate substantially free from the ester of the cyanoacetic acid, the alcohol, the catalyst(s) and/or the cyanoacetate, and by-products.
1 more element
A process for the preparation of an electron deficient olefin, steps of which comprise:
- (a) providing as reactants:
- (i) a 2-electron withdrawing group-substituted methylene compound embraced by:
- wherein EWG represents an electron withdrawing group;
- and R here represents straight chain, branched, cyclic or fused C1-20 alkyl, C2-20 alkenyl, C2-20 alkynyl, and C6-20 aryl or C7-20 alkaryl, with or without substitution or interruption by one or more heteroatoms;
- and
- (ii) an alcohol;
- (b) reacting the 2-electron withdrawing group-substituted methylene compound and the alcohol in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield an electron deficient olefin precursor embraced by:
- wherein EWG represents an electron withdrawing group;
- and R here represents straight chain, branched, cyclic or fused C1-20 alkyl, C2-20 alkenyl, C2-20 alkynyl, and C6-20 aryl or C7-20 alkaryl, with or without substitution or interruption by one or more heteroatoms, provided it is different from R in step (a)(i);
- (c) reacting the electron deficient olefin precursor and a source of aldehyde, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield an electron deficient olefin;
- and
- (d) optionally, separating from the mixture the so-formed electron deficient olefin substantially free from the reactants and by-products.
9 more elements
A process for the preparation of a cyanoacrylate, steps of which comprise:
- (a) providing as reactants an ester of cyanoacetic acid and an alcohol;
- (b) reacting the ester of cyanoacetic acid and the alcohol in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacetate different from the ester of cyanoacetic acid;
- (c) reacting the so-formed cyanoacetate with a source of aldehyde, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacrylate;
- and
- (d) optionally, separating from the mixture the so-formed cyanoacrylate substantially free from the reactants and by-products.
2 more elements
A process for the preparation of a cyanoacrylate, steps of which comprise:
- (a) reacting an ester of cyanoacetic acid and a alcohol, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacetate different from the ester of cyanoacetic acid;
- (b) reacting the so-formed cyanoacetate with a source of aldehyde, in the presence of a catalyst comprising a lanthanide element or a transition element, under appropriate conditions and for a time sufficient to yield a cyanoacrylate;
- and
- (c) optionally, separating the so-formed cyanoacrylate substantially free from the ester of cyanoacetic acid, the alcohol, the catalyst(s) and/or the cyanoacetate, and by-products.
1 more element
Dependencies are inferred from the claim text.