US 2025/0010278 A1 · STERICALLY MODIFIED SCHIFF BASE LIGANDS FOR ENHANCED CATALYTIC CARBONYLATION ACTIVITY

Abstract

A composition, comprising: a metal carbonyl anion; and a cation ionically bonded to the metal carbonyl anion. The cation includes a ligand and a metal centered compound. The ligand includes two residues of 3,5-substituted salicylaldehydes connected by an hydrocarbyl-diimine bridge that includes a nitrogen atom contacted with a carbon of an aldehyde residue at each of the two residues of the 3,5-substituted salicylaldehydes. Each of the residues of the 3,5-substituted salicylaldehydes are independently substituted at one or both of a 3 position and a 5 position by a hydrocarbyl group containing at least 5 carbons. The metal coordinated with the ligand at each hydroxyl residue the two residues of the 3,5-substituted salicylaldehydes at a 2 position and at each of the nitrogen atoms of the hydrocarbyl-diimine bridge. The composition includes two polar ligands coordinated with the metal.

Claims31

Dependent claims

A composition, comprising:

a) a metal carbonyl anion;
and
b) a cation ionically bonded to the metal carbonyl anion, comprising:
i) a ligand including two residues of 3,5-substituted salicylaldehydes connected by a hydrocarbyl-diimine bridge that includes a nitrogen atom contacted with a carbon of an aldehyde residue at each of the two residues of the 3,5-substituted salicylaldehydes, wherein each of the residues of the 3,5-substituted salicylaldehydes are independently substituted at 3 position by a hydrocarbyl group that is a branched alkyl-aryl group, and wherein each of the residues of the 3,5-substituted salicylaldehydes are independently substituted at a 5 position by a hydrogen, methyl, a —C2-C12, alkyl group, an aryl group, a t-butyl alkyl group, a halogen, an amine, —CF5, hydrocarbyl oxy group, or —NO2;
ii) a metal coordinated with the ligand at each hydroxyl residue the two residues of the 3,5-substituted salicylaldehydes at a 2 position and at each of the nitrogen atoms of the hydrocarbyl-diimine bridge;
and
iii) two polar ligands coordinated with the metal.

4 more elements

A method, comprising:

a) contacting a ligand with a metalating agent to form a metal centered compound, wherein the ligand includes the residues of two 3, 5-substituted salicylaldehydes connected by an hydrocarbyl-diimine bridge at the aldehyde residue of the two residues of the 3,5-substituted salicylaldehydes, wherein each substitution at a 3 position comprises a hydrocarbyl group comprising an alkyl-aryl group and wherein each substitution of the 3,5-substituted salicylaldehydes at a 5 position comprises hydrogen, methyl, a —C2-C12, alkyl group, an aryl group, a t-butyl alkyl group, a halogen, an amine, —CF5, hydrocarbyl oxy group, or —NO2;
and
b) contacting the metal centered compound with a metal carbonyl and a polar ligand to form a composition.

A method, comprising contacting an epoxide and carbon monoxide in the presence of a carbonylation catalyst to form beta propiolactone,

wherein the carbonylation catalyst comprises:
c) a metal carbonyl anion;
and
d) a cation ionically bonded to the metal carbonyl anion, comprising:
i) a ligand including two residues of 3,5-substituted salicylaldehydes connected by a hydrocarbyl-diimine bridge that includes a nitrogen atom contacted with a carbon of an aldehyde residue at each of the two residues of the 3,5-substituted salicylaldehydes, each of the residues of the 3,5-substituted salicylaldehydes independently substituted at one or both of a 3 position and a 5 position by a hydrocarbyl group comprising an alkyl-aryl group containing at least 5 carbons;
ii) a metal coordinated with the ligand at each hydroxyl residue of a 2 position of the two residues of the 3,5-substituted salicylaldehydes and at each of the nitrogen atoms of the hydrocarbyl-diimine bridge;
and
iii) two polar ligands coordinated with the metal.

5 more elements

Dependencies are inferred from the claim text.

Sterically modified schiff base ligands for enhanced catalytic carbonylation activity

Life of this patent

Sterically modified schiff base ligands for enhanced catalytic carbonylation activity

Life of this patent

Abstract

Claims31