• Title/Summary/Keyword: Knoevenagel Condensation

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Indium Modified Mesoporous Zeolite AlMCM-41 as a Heterogeneous Catalyst for the Knoevenagel Condensation Reaction

  • Katkar, Santosh S.;Lande, Machhindra K.;Arbad, Balasaheb R.;Rathod, Sandip B.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1301-1304
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    • 2010
  • The Indium modified mesoporous zeolite AlMCM-41 were synthesized by hydrothermal method and characterized by powder X-ray diffraction (XRD), fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy with energy dispersive spectroscopy (SEM-EDS) techniques. The Knoevenagel condensation of aldehyde with malononitrile or ethyl cyanoacetate was carried out at reflux condition in ethanol by using heterogeneous In/AlMCM-41 catalyst. This method is fast, efficient, easy work-up and eco-friendly to afford the corresponding Knoevenagel adducts. The catalyst was recovered and reused for several cycles with consistent activity.

Knoevenagel Reaction in Water Catalyzed by Mesoporous Silica Materials Synthesized from Industrial Waste Coal Fly Ash (석탄회 산업폐기물로부터 제조한 메조다공성 실리카소재를 촉매로 사용하는 Knoevenagel 수용액 반응)

  • Dhokte, Aashish O.;Khillare, Santosh L.;Lande, Machhindra K.;Arbad, Balasaheb R.
    • Journal of the Korean Chemical Society
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    • v.55 no.3
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    • pp.430-435
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    • 2011
  • Coal fly ash of thermal power plants converted into mesoporous materials MCM-41. The synthesized material was characterized by XRD, FT-IR, SEM, and EDS techniques. The catalytic activity of prepared material was studied for the synthesis of 5-arylindene malononitriles via Knoevenagel condensation of aromatic aldehydes and malonontrile is described. The features of present method are easy handling, stability, reusability, and eco-friendliness of catalyst, high yields, short reaction time, simple experimental and work up procedure.

Knoevenagel Condensation Reaction Using Amine-functionalized MCM-41 Base Catalysts (아민고정화 MCM-41 염기촉매를 이용한 Knoevenagel 축합반응)

  • Choi, Jung-Sik;Ahn, Wha-Seung
    • Korean Chemical Engineering Research
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    • v.44 no.4
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    • pp.417-423
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    • 2006
  • A series of amine functionalized MCM-41 catalysts were prepared by aminopropyltrimethoxysilane grafting and their catalytic performance in Knoevenagel reaction of selected substrates was investigated. Water resistant and catalytically active amine grafted MCM-41 was prepared by post-synthetic silylation using methyltrimethoxysilane ; hydrogen bonding of the water molecules formed during the condensation reaction to the active N group was suppressed, which led to high TON of the reaction. Amine functionalized MCM-41 prepared by coating method produced high conversion, but the TON of the catalyst was much lower than that of the amine grafted MCM-41; pore volume of the functionalized MCM-41 decreased substantially and large portion of the immobilized amine is believed to be hydrogen bonded to each other, which can result in decrease in the basicity of the N group. A secondary amine group was prepared by room temperature condensation between aminopropylsilane and chloropropylsilane, and the MCM-41 grafted with the secondary amine group demonstrated the highest catalytic activity among the catalysts prepared.

Silica Supported Ammonium Acetate: An Efficient and Recyclable Heterogeneous Catalyst for Knoevenagel Condensation between Adehydes or Ketones and Active Methylene Group in Liquid Phase

  • Gupta, Raman;Gupta, Monika;Paul, Satya;Gupta, Rajive
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2419-2421
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    • 2009
  • A simple and efficient method has been developed for Knoevenagel condensation between aldehydes or ketones and active methylene group by stirring in methylene chloride at 60 ${^{\circ}C}$ under heterogeneous conditions using silica supported ammonium acetate. The products are obtained in excellent yields and are in a state of high purity. The structures of the products were confirmed by IR, $^1H$ NMR and mass spectral data and comparison with authentic samples available commercially.

Dry Media Reaction Procedure for Synthesis of α,β-Unsaturated Acids, α-Cyanoacrylonitriles and α-Cyanoacrylates via Knoevenagel Condensation Using NaHSO4·SiO2 Catalyst (NaHSO4·SiO2 촉매를 이용한 Knoevenagel 축합을 거친α,β의 불포화산, α-Cyanoacrylonitriles와 α-Cyanoacrylates의 합성을 위한 무수조건하의 반응 절차)

  • Gopalakrishnan, M.;Sureshkumar, P.;Kanagarajan, V.;Thanusu, J.;Thirunavukkarasu, S.
    • Journal of the Korean Chemical Society
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    • v.51 no.4
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    • pp.346-351
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    • 2007
  • Efficient stereoselective synthesis of α,β-Unsaturated acids, α-Cyanoacrylonitriles and α-Cyanoacrylates has been carried out in the presence of NaHSO4·SiO2 under solvent?free conditions with an E-geometry.

Synthesis, Characterization and Application of Poly(4-Methyl Vinylpyridinium Hydroxide)/SBA-15 Composite as a Highly Active Heterogeneous Basic Catalyst for the Knoevenagel Reaction

  • Kalbasi, Roozbeh Javad;Kolahdoozan, Majid;Massah, Ahmadreza;Shahabian, Keinaz
    • Bulletin of the Korean Chemical Society
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    • v.31 no.9
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    • pp.2618-2626
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    • 2010
  • In this paper poly (4-methyl vinylpyridinium hydroxide)/SBA-15 composite was prepared as a highly efficient heterogeneous basic catalyst by in situ polymerization method for the first time. It was characterized by XRD, FT-IR, BET, TGA, SEM and back titration using NaOH. This catalyst exhibited the excellent catalytic activities for the Knoevenagel condensation of various aldehydes with ethyl cyanoacetate. Over this catalyst, ${\alpha},{\beta}$-unsaturated carbonyl compounds were obtained in the reasonable yield at $95^{\circ}C$ in 10 - 30 min in $H_2O$ as a solvent with a 100% selectivity to the condensation products. Catalyst could be easily recycled after the reaction and it could be reused without the significant loss of activity/selectivity performance. No by-product formation, high yields, short reaction times, mild reaction conditions and operational simplicity with reusability of the catalyst were the salient features of the present synthetic protocol. Presence of $H_2O$ as a solvent was also recognized as a "green method".

Synthesis, Characterization and Catalytic Activity of Ce1MgxZr1-xO2 (CMZO) Solid Heterogeneous Catalyst for the Synthesis of 5-Arylidine Barbituric acid Derivatives

  • Rathod, Sandip B.;Gambhire, Anil B.;Arbad, Balasaheb R.;Lande, Machhindra K.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.2
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    • pp.339-343
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    • 2010
  • A series of $Ce_1Mg_xZr_{1-x}O_2$ (CMZO) mixed metal oxide with different molar ratio were prepared by simple co-precipitation method. The prepared materials were tested for their catalytic activity performance using Knoevenagel condensation of various aromatic aldehydes with barbituric acid under solvent-free condition in microwave. The best catalytic activity was obtained with CMZO (1:0.6:0.4). The synthesized materials were characterized by using XRD, FT-IR, SEM-EDS techniques.