Synthesis of N,N ‐Dimethylaminoethyl Acrylate via a Zinc Phenoxyimine and Phenoxyamidine Complexes Catalyzed Transesterification Reaction
Open Access
- 2 October 2025
- journal article
- Published by Wiley in Applied Organometallic Chemistry
- Vol. 39 (11)
Abstract
Heteroleptic and homoleptic complexes of zinc with phenoxyimine and phenoxyamidine ligands are used as alternatives to currently used tin catalysts in the transesterification reaction of methyl acrylate and N,N‐ dimethylethanolamine in the synthesis of N,N‐ dimethylaminoethyl acrylate. A large screening of phenoxyimine and three generations of phenoxyamidine ligands has been undertaken and used to determine the best catalysts in terms of conversion and selectivity. All of the catalysts tested show significant improvement in activity over catalysts currently well‐established in industrial processes such as dibutyltin oxide or Ti(O i Pr) 4 . The catalytic charges can be decreased significantly (10–20×) still affording good conversions and selectivities. A series of heteroleptic and homoleptic zinc complexes with phenoxyimine and phenoxyamidine ligands have been tested for the transesterification of methyl acrylate with N,N ‐dimethylethanolamine. All the catalysts demonstrated a substantial increase in activity compared to dibutyltin oxide, a well‐established catalyst that is currently used in industry for this reaction.Keywords
Funding Information
- Agence Nationale de la Recherche (ANR‐22‐CE07‐0011)
This publication has 39 references indexed in Scilit:
- Robust Guanidine Metal Catalysts for the Ring‐Opening Polymerization of Lactide under Industrially Relevant ConditionsChempluschem, 2020
- Screening of metal catalysts influence on the synthesis, structure, properties, and biodegradation of PLA‐PBA triblock copolymers obtained in meltJournal of Polymer Science Part A: Polymer Chemistry, 2015
- Transesterification of jatropha oil with methanol over Mg–Zn mixed metal oxide catalystsEnergy, 2013
- Transesterification kinetics of Camelina sativa oil on metal oxide catalysts under conventional and microwave heating conditionsChemical Engineering Journal, 2011
- Polymer-supported titanate as catalyst for the transesterification of acrylic monomersComptes Rendus. Chimie, 2010
- Silica‐Supported Zirconium Complexes and their Polyoligosilsesquioxane Analogues in the Transesterification of Acrylates: Part 2. Activity, Recycling and RegenerationAdvanced Synthesis & Catalysis, 2009
- Solid trichlorotitanium(IV) trifluoromethanesulfonate TiCl3(OTf) catalyzed efficient acylation of –OH and –SH: Direct esterification of alcohols with carboxylic acids and transesterification of alcohols with esters under neat conditionsJournal of Molecular Catalysis A: Chemical, 2008
- Reaction Kinetics of Soybean Oil Transesterification Using Heterogeneous Metal Oxide CatalystsChemical Engineering & Technology, 2007
- A new catalytic transesterification for the synthesis of N, N-dimethylaminoethyl acrylate with organotin catalystCatalysis Letters, 2006
- Ring‐Opening Polymerization of Cyclic Monomers with Aluminum TriflateMacromolecular Symposia, 2005