CLC number: TQ138.1
On-line Access: 2024-08-27
Received: 2023-10-17
Revision Accepted: 2024-05-08
Crosschecked: 2019-12-28
Cited: 0
Clicked: 3460
Citations: Bibtex RefMan EndNote GB/T7714
Yang-yang Fang, Xiao-zhong Wang, Ying-qi Chen, Li-yan Dai. NiCo2O4 nanoparticles: an efficient and magnetic catalyst for Knoevenagel condensation[J]. Journal of Zhejiang University Science A, 2020, 21(1): 74-84.
@article{title="NiCo2O4 nanoparticles: an efficient and magnetic catalyst for Knoevenagel condensation",
author="Yang-yang Fang, Xiao-zhong Wang, Ying-qi Chen, Li-yan Dai",
journal="Journal of Zhejiang University Science A",
volume="21",
number="1",
pages="74-84",
year="2020",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.A1900535"
}
%0 Journal Article
%T NiCo2O4 nanoparticles: an efficient and magnetic catalyst for Knoevenagel condensation
%A Yang-yang Fang
%A Xiao-zhong Wang
%A Ying-qi Chen
%A Li-yan Dai
%J Journal of Zhejiang University SCIENCE A
%V 21
%N 1
%P 74-84
%@ 1673-565X
%D 2020
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.A1900535
TY - JOUR
T1 - NiCo2O4 nanoparticles: an efficient and magnetic catalyst for Knoevenagel condensation
A1 - Yang-yang Fang
A1 - Xiao-zhong Wang
A1 - Ying-qi Chen
A1 - Li-yan Dai
J0 - Journal of Zhejiang University Science A
VL - 21
IS - 1
SP - 74
EP - 84
%@ 1673-565X
Y1 - 2020
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.A1900535
Abstract: The knoevenagel condensation reaction has wide applications ranging from the manufacture of basic chemicals to pharmaceutical intermediates. In this study, we developed an efficient and magnetic bimetallic NiCo2O4 nanocatalyst by coprecipitation. When used in the knoevenagel condensation between various benzaldehydes and malononitrile, the catalyst exhibited excellent catalytic performance with 99% conversion and 99% selectivity under mild conditions. It can be easily recovered with a magnet and recycled for 20 runs without significant loss of activity. We expect that the catalyst will find large-scale industrial applications.
[1]Adisakwattana S, Moonsan P, Yibchok-Anun S, 2008. Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo. Journal of Agricultural and Food Chemistry, 56(17):7838-7844.
[2]Ali I, Haque A, Saleem K, et al., 2013. Curcumin-I Knoevenagel’s condensates and their Schiff’s bases as anticancer agents: synthesis, pharmacological and simulation studies. Bioorganic & Medicinal Chemistry, 21(13):3808-3820.
[3]Boronat M, Climent MJ, Corma A, et al., 2010. Bifunctional acid-base ionic liquid organocatalysts with a controlled distance between acid and base sites. Chemistry, 16(4):1221-1231.
[4]Burri DR, Shaikh IR, Choi KM, et al., 2007. Facile heterogenization of homogeneous ferrocene catalyst on SBA-15 and its hydroxylation activity. Catalysis Communications, 8(4):731-735.
[5]Chen XW, Li XH, Song HB, et al., 2008. Synthesis of a basic imidazolide ionic liquid and its application in catalyzing Knoevenagel condensation. Chinese Journal of Catalysis, 29(10):957-959.
[6]Dai L, Cao CX, Gao YF, et al., 2011. Synthesis and phase transition behavior of undoped VO2 with a strong nano-size effect. Solar Energy Materials and Solar Cells, 95(2):712-715.
[7]El Baydi M, Tiwari SK, Singh RN, et al., 1995. High specific surface area nickel mixed oxide powders LaNiO3 (perovskite) and NiCo2O4 (spinel) via sol-gel type routes for oxygen electrocatalysis in alkaline media. Journal of Solid State Chemistry, 116(1):157-169.
[8]Gao Z, Zhou J, Cui FM, et al., 2010. Superparamagnetic mesoporous Mg-Fe bi-metal oxides as efficient magnetic solid-base catalysts for Knoevenagel condensations. Dalton Transactions, 39(46):11132-11135.
[9]Gawande MB, Jayaram RV, 2006. A novel catalyst for the Knoevenagel condensation of aldehydes with malononitrile and ethyl cyanoacetate under solvent free conditions. Catalysis Communications, 7(12):931-935.
[10]Ghomi JS, Akbarzadeh Z, 2018. Ultrasonic accelerated Knoevenagel condensation by magnetically recoverable MgFe2O4 nanocatalyst: a rapid and green synthesis of coumarins under solvent-free conditions. Ultrasonics Sonochemistry, 40:78-83.
[11]Hua YM, Hu WM, 2004. Rapid synthesis of ZSM-5 zeolite catalyst for amination of ethanolamine. Journal of Zhejiang University-SCIENCE, 5(6):705-708.
[12]Jameel U, Zhu MQ, Chen XZ, et al., 2016. Green epoxidation of cyclooctene with molecular oxygen over an ecofriendly heterogeneous polyoxometalate-gold catalyst Au/BW11/Al2O3. Journal of Zhejiang University-SCIENCE A (Applied Physics & Engineering), 17(12):1000-1012.
[13]Jiang H, Wang M, Song ZG, et al., 2009. Inorganic zinc salts catalyzed Knoevenagel condensation at room temperature without solvent. Preparative Biochemistry & Biotechnology, 39(2):194-200.
[14]Kaikhosravi M, Hadadzadeh H, Katani S, 2016. NiCo2O4 nanospinel and its catalytic activity for oxidation of Rhodamine B at ambient conditions. Materials Chemistry and Physics, 170:62-70.
[15]Karaoğlu E, Baykal A, Şenel M, et al., 2012. Synthesis and characterization of piperidine-4-carboxylic acid functionalized Fe3O4 nanoparticles as a magnetic catalyst for Knoevenagel reaction. Materials Research Bulletin, 47(9):2480-2486.
[16]Kasralikar HM, Jadhavar SC, Bhusare SR, et al., 2015. Synthesis and molecular docking studies of oxochromenyl xanthenone and indolyl xanthenone derivatives as anti-HIV-1 RT inhibitors. Bioorganic & Medicinal Chemistry Letters, 25(18):3882-3886.
[17]Khan D, Mukhtar S, Alsharif MA, et al., 2017. PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives. Tetrahedron Letters, 58(32):3183-3187.
[18]Ladipo FT, Anderson GK, 1994. Convenient method for the synthesis of chloro-bridged methyl- and acetylpalladium(II) dimers. Organometallics, 13(1):303-306.
[19]Li QC, Wang XZ, Yu YY, et al., 2016. Tailoring a magnetically separable NiFe2O4 nanoparticle catalyst for Knoevenagel condensation. Tetrahedron, 72(50):8358-8363.
[20]Liu JB, Shi HJ, Shen Q, et al., 2017. A biomimetic photoelectrocatalyst of Co–porphyrin combined with a g-C3N4 nanosheet based on π–π supramolecular interaction for high-efficiency CO2 reduction in water medium. Green Chemistry, 19(24):5900-5910.
[21]Lu T, Chen FW, 2012. Multiwfn: a multifunctional wavefunction analyzer. Journal of Computational Chemistry, 33(5):580-592.
[22]Mahmoudi H, Malakooti R, 2014. Solvent free highly dispersed zinc oxide within confined space of Al-containing SBA-15 as an efficient catalyst for Knoevenagel condensation. Letters in Organic Chemistry, 11(6):457-464.
[23]Modak A, Mondal J, Bhaumik A, 2013. Porphyrin based porous organic polymer as bi-functional catalyst for selective oxidation and Knoevenagel condensation reactions. Applied Catalysis A: General, 459:41-51.
[24]Pang MJ, Jiang S, Long GH, et al., 2016. Mesoporous NiCo2O4 nanospheres with a high specific surface area as electrode materials for high-performance supercapacitors. RSC Advances, 6(72):67839-67848.
[25]Rubio-Clemente A, Chica E, Peñuela GA, 2015. Petrochemical wastewater treatment by photo-Fenton process. Water, Air, & Soil Pollution, 226:62.
[26]Sharma N, Sharma A, Shard A, et al., 2011. Tandem allylic oxidation-condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes. Organic & Biomolecular Chemistry, 9(14):5211-5219.
[27]Sharona H, Loukya B, Bhat U, et al., 2017. Coexisting nanoscale inverse spinel and rock salt crystallographic phases in NiCo2O4 epitaxial thin films grown by pulsed laser deposition. Journal of Applied Physics, 122(22):225301.
[28]Sirotin SV, Moskovskaya IF, Romanovsky BV, 2011. Synthetic strategy for Fe-MCM-41 catalyst: a key factor for homogeneous or heterogeneous phenoloxidation. Catalysis Science & Technology, 1(6):971-980.
[29]Sun Q, Shi LX, Ge ZM, et al., 2005. An efficient and green procedure for the Knoevenagel condensation catalyzed by urea. Chinese Journal of Chemistry, 23(6):745-748.
[30]Taher A, Lee DJ, Lee BK, et al., 2016. Amine-functionalized metal-organic frameworks: an efficient and recyclable heterogeneous catalyst for the Knoevenagel condensation reaction. Synlett, 27(9):1433-1437.
[31]Tamaddon F, Azadi D, 2017. Preparation of a superior liquid catalyst by hybridization of three solids of nanoZnO, urea, and choline chloride for Knoevenagel-based reactions. Journal of the Iranian Chemical Society, 14(10):2077-2086.
[32]Texier-Boullet F, Foucaud A, 1982. Knoevenagel condensation catalysed by aluminium oxide. Tetrahedron Letters, 23(47):4927-4928.
[33]Tryambake PT, 2017. Microwave assisted urea-acetic acid catalyzed Knoevenagel condensation of ethyl cyanoacetate and 1,3-thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition. Asian Journal of Chemistry, 29(11):2401-2405.
[34]Viveka S, Vasantha G, Dinesha, et al., 2016. Structural, spectral, and theoretical investigations of 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid. Research on Chemical Intermediates, 42(5):4497-4511.
[35]Voge HH, Good GM, 1949. Thermal cracking of higher paraffins. Journal of the American Chemical Society, 71(2):593-597.
[36]Wang SX, Li JT, Yang WZ, et al., 2002. Synthesis of ethyl α-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation. Ultrasonics Sonochemistry, 9(3):159-161.
[37]Xie J, Chen L, Au CT, et al., 2015. Synthesis of KOH/SnO2 solid superbases for catalytic Knoevenagel condensation. Catalysis Communications, 66:30-33.
[38]Xu J, Shen K, Xue B, et al., 2013. Microporous carbon nitride as an effective solid base catalyst for Knoevenagel condensation reactions. Journal of Molecular Catalysis A: Chemical, 372:105-113.
[39]Xue B, Liu XM, Liu N, et al., 2018. A simple strategy to prepare graphene oxide modified by ammonia gas catalysts for Knoevenagel condensation. Research on Chemical Intermediates, 44(3):1523-1536.
[40]Yang PK, Liu YW, Chai L, et al., 2018. Nmp-based ionic liquids: recyclable catalysts for both hetero-Michael addition and Knoevenagel condensation in water. Synthetic Communications, 48(9):1060-1067.
[41]Ying AG, Wang LM, Qiu FL, et al., 2015. Magnetic nanoparticle supported amine: an efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation. Comptes Rendus Chimie, 18(2):223-232.
[42]Zhang F, Yang XS, Jiang L, et al., 2013. Piperazine-functionalized ordered mesoporous polymer as highly active and reusable organocatalyst for water-medium organic synthesis. Green Chemistry, 15(6):1665-1672.
[43]Zhang Y, Xia CG, 2009. Magnetic hydroxyapatite-encapsulated γ-Fe2O3 nanoparticles functionalized with basic ionic liquids for aqueous Knoevenagel condensation. Applied Catalysis A: General, 366(1):141-147.
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