DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter

N-(2-Hydroxy-ethyl)-pyridinium chloride ([HyEtPy]Cl) was synthesized and explored as a novel promoter for 1,4-diazabicyclo [2.2.2] octane (DABCO)-catalyzed Knoevenagel condensation reactions, excellent catalytic activity was obtained.

Download Full-text

Layer-Like Zeolite X as Catalyst in a Knoevenagel Condensation: The Effect of Different Preparation Pathways and Cation Exchange

Catalysts ◽

10.3390/catal11040474 ◽

2021 ◽

Vol 11 (4) ◽

pp. 474

Author(s):

Jan-Paul Grass ◽

Katharina Klühspies ◽

Bastian Reiprich ◽

Wilhelm Schwieger ◽

Alexandra Inayat

Keyword(s):

Catalytic Activity ◽

Reaction Rate ◽

Knoevenagel Condensation ◽

Ethyl Cyanoacetate ◽

Reaction Rates ◽

Initial Reaction Rate ◽

Comparative Investigation ◽

Morphological Properties ◽

Initial Reaction ◽

Zeolite X

This study is dedicated to the comparative investigation of the catalytic activity of layer-like Faujasite-type (FAU) zeolite X obtained from three different synthesis routes (additive-free route, Li2CO3 route, and TPOAC route) in a liquid-phase Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate to ethyl trans-α-cyanocinnamate. It is shown that the charge-balancing cations (Na+ and K+) and the morphological properties have a strong influence on the apparent reaction rate and degree of conversion. The highest initial reaction rate could be found for the layer-like zeolite X synthesised by the additive-free route in the potassium form. In most cases, the potassium-exchanged zeolites enabled higher maximum conversions and higher reaction rates compared to the zeolite X catalysts in sodium form. However, very thin crystal plates (below 100 nm thickness), similar to those obtained in the presence of TPOAC, did not withstand the multiple aqueous ion exchange procedure, with the remaining coarse crystals facilitating less enhancement of the catalytic activity.

Download Full-text

An Efficient and Recyclable Imidazolium Salts-Functionalized Mesoporous Catalyst for Microwave-Promoted Knoevenagel Condensations in Solid Medium

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.347-353.1944 ◽

2011 ◽

Vol 347-353 ◽

pp. 1944-1948

Author(s):

Yu Long Xu ◽

Chuan Shou Sun ◽

Guo Hua Liu

Keyword(s):

Catalytic Activity ◽

Microwave Irradiation ◽

Convenient Method ◽

Solid Medium ◽

Knoevenagel Condensation ◽

Ethyl Cyanoacetate ◽

High Catalytic Activity ◽

Imidazolium Salts ◽

Mesoporous Catalyst ◽

Catalytic Activities

A convenient method for the preparation of imidazolium salts-functionalized mesoporous catalyst Me-Bmim-SBA-15 (2) by postgrafting [bmIm]OH on SBA-15 was developed. This catalyst presented excellent catalytic activities (more than 96% yields for all tested aldehydes) for Knoevenagel condensation of aldehydes and ethyl cyanoacetate under microwave irradiation in solid medium. Of particular note is that such a catalyst could be readily recovered and reused in the consecutively catalytic runs (up to 10 uses) while maintained high catalytic activity.

Download Full-text

1,3-Dialkylimidazolium Dimethyl Phosphates – Effective Solvents and Catalysts for Condensation Reactions

Latvian Journal of Chemistry ◽

10.2478/ljc-2013-0004 ◽

2014 ◽

Vol 52 (1-2) ◽

pp. 41-48

Author(s):

L. Anteina ◽

A. Gaidule ◽

A. Zicmanis

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Malonic Acid ◽

Condensation Reaction ◽

Ethyl Cyanoacetate ◽

Liquid Structure ◽

Reaction Rates ◽

Condensation Reactions

Abstract We report the preparation, characterization and exploitation of 1,3-dialkylimidazolium dimethyl phosphates. Condensation reactions of benzaldehyde with ethyl cyanoacetate and with malonic acid were performed in these ionic liquids either in absence or in presence of other catalysts. The effect of ionic liquid structure on the condensation reaction rates and yields was discussed

Download Full-text

Supported choline hydroxide (ionic liquid) on mesoporous silica as heterogeneous catalyst for Knoevenagel condensation reactions

Microporous and Mesoporous Materials ◽

10.1016/j.micromeso.2017.12.024 ◽

2018 ◽

Vol 263 ◽

pp. 173-180 ◽

Cited By ~ 18

Author(s):

Isabel del Hierro ◽

Yolanda Pérez ◽

Mariano Fajardo

Keyword(s):

Ionic Liquid ◽

Mesoporous Silica ◽

Heterogeneous Catalyst ◽

Knoevenagel Condensation ◽

Condensation Reactions

Download Full-text

Catalytic Activity of Proton Sponge: Application to Knoevenagel Condensation Reactions

Journal of Catalysis ◽

10.1006/jcat.1998.2380 ◽

1999 ◽

Vol 183 (1) ◽

pp. 14-23 ◽

Cited By ~ 56

Author(s):

I. Rodriguez ◽

G. Sastre ◽

A. Corma ◽

S. Iborra

Keyword(s):

Catalytic Activity ◽

Knoevenagel Condensation ◽

Proton Sponge ◽

Condensation Reactions

Download Full-text

Fabrication of a metal free catalyst for chemical reactions through decoration of chitosan with ionic liquid terminated dendritic moiety

Scientific Reports ◽

10.1038/s41598-020-76795-8 ◽

2020 ◽

Vol 10 (1) ◽

Author(s):

Samahe Sadjadi ◽

Fatemeh Koohestani ◽

Majid M. Heravi

Keyword(s):

Ionic Liquid ◽

Catalytic Activity ◽

High Activity ◽

Functional Groups ◽

Chemical Reactions ◽

Knoevenagel Condensation ◽

Aqueous Media ◽

Metal Free ◽

Xanthene Derivatives ◽

Mapping Analysis

AbstractIn attempt to develop a biocompatible metal-free catalyst, a dendritic moiety was grown on chitosan through successive reactions with 2,4,6-trichloro-1,3,5-triazine and ethylenediamine. Subsequently, the terminal functional groups of the dendron were decorated with 1-methylimidazolium chloride. The catalyst was characterized with SEM, EDS, TGA, FTIR, XRD and mapping analysis. Then, the catalytic activity of the resultant composite was scrutinized for catalyzing Knoevenagel condensation and synthesis of xanthene derivatives in aqueous media under mild reaction condition. The results confirmed high activity of the catalyst, superior to ionic liquid free counterpart and bare chitosan. This observation was ascribed to the instinct catalytic activity of ionic liquid. Moreover, using control catalysts, it was confirmed that the presence of the dendritic moiety that could increase the content of ionic liquid on the backbone of the catalyst enhanced the catalytic activity.

Download Full-text

Bismuth (III) Triflate: A Mild, Efficient Promoter for the Synthesis of Trisubstituted Alkenes through Knoevenagel Condensation

Oriental Journal Of Chemistry ◽

10.13005/ojc/360507 ◽

2020 ◽

Vol 36 (05) ◽

pp. 843-849

Author(s):

Arup Datta

Keyword(s):

Catalytic Activity ◽

Knoevenagel Condensation ◽

Condensation Product ◽

Ethyl Cyanoacetate ◽

Free Condition ◽

Solvent Free Condition ◽

Two Component ◽

Active Methylene Compounds ◽

Trisubstituted Alkenes ◽

Active Methylene

In this work, smooth efficient and eco-friendly two component coupling method is reported for the synthesis of Knoevenagel Condensation product in presence of Bi(OTf)3 catalyst under solvent free condition. Catalyst has participated in condensation between substituted aldehydes (aromatic and hetero-aromatic) and active methylene compounds (ethyl cyanoacetate, malononitrile and cyanoacetamide) effectively to generate an excellent yield of the product. Bi(OTf)3 catalyst is stable, inexpensive and easily available was used for four times in this reaction without loss of catalytic activity.

Download Full-text