Bismuth Oxychloride as an Efficient Heterogeneous Catalyst for Aldol Condensation Reaction between Aldehydes and Ketones

The aldol reaction is a cornerstone of modern synthetic organic chemistry in which the β-hydroxyketone was formed by the reaction of an enol or an enolate and a carbonyl compound. Benzalacetone is one of the fundamental building blocks of benzalacetone synthase structure that play an important role for construction of a variety of medicinally crucial phenylbutanoids, such as anti-inflammatory glucoside lindleyin in rhubarb and gingerol. The non-transition metal material attracted much attention from research groups on the world, such a potential catalyst as BiOCl for organic reaction due to its remarkably chemical and physical properties as relative stability, resistance of air and moisture, low toxicity. The BiOCl material was synthesized by the solvothermal method. The structure features of material were defined by modern analytic methods such as X-ray diffraction (XRD), Fourier Transform infrared spectroscopy (FT-IR), Scaning Electron Microscope (SEM), and Nitrogen Adsorption-Desorption Isotherms. The BiOCl material was successfully utilized as a catalyst for the aldol condensation reaction of benzaldehyde and acetone. The reaction was performed in the mild condition with the presence of 10 mol% catalyst and 2 equivalent of Cs2CO3 as base without by-product in very short reaction times and good yields. The benzalacetone product obtained around 85% yield at 120 °C for 24 h. The BiOCl material after reaction was recovered and reused many times without significant reducing of catalytic activity. Copyright © 2023 by Authors, Published by BCREC Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0). 

[1]  Jinshui Zhang,et al.  Chelated Ion‐Exchange Strategy toward BiOCl Mesoporous Single‐Crystalline Nanosheets for Boosting Photocatalytic Selective Aromatic Alcohols Oxidation , 2023, Advances in Materials.

[2]  K. Hernádi,et al.  Hydrothermal Crystallization of Bismuth Oxychlorides (BiOCl) Using Different Shape Control Reagents , 2021, Materials.

[3]  T. Gregg,et al.  Aldol Condensation Reaction Rate Demonstrates Steric and Electronic Substituent Effects in the Organic Chemistry Lab , 2021 .

[4]  Ming Xu,et al.  A facile synthesis of bismuth oxychloride-graphene oxide composite for visible light photocatalysis of aqueous diclofenac sodium , 2020, Scientific Reports.

[5]  Yongjun Yuan,et al.  Highly dispersed BiOCl decahedra with a highly exposed (001) facet and exceptional photocatalytic performance. , 2020, Dalton transactions.

[6]  Aili Wang,et al.  Acrylic acid synthesis via condensation of acetic acid and formaldehyde catalyzed by silica aerogel‐supported SiW/PW/PMo oxides , 2020 .

[7]  M. Meléndrez,et al.  Effect of temperature and reaction time during solvothermal synthesis of BiOCl on microspheres formation: implications in the photocatalytic oxidation of gallic acid under simulated solar radiation , 2020, Journal of Sol-Gel Science and Technology.

[8]  D. Rubiyanto,et al.  Comparative study of the effectiveness of Na2CO3 and K2CO3 as base in methylation reaction on eugenol using dimethylcarbonate , 2020 .

[9]  G. Qian,et al.  Separation and recovery of materials from the waste light emitting diode (LED) modules by solvent method , 2020 .

[10]  Aili Wang,et al.  Reaction between methanol and acetic acid catalyzed by SiO 2 ‐supported V‐P‐O catalyst in oxygen atmosphere , 2019, The Canadian Journal of Chemical Engineering.

[11]  Michael Müller,et al.  Vaporization behavior of Na2CO3 and K2CO3 , 2019, Calphad.

[12]  J. Ruiz,et al.  Aldol Condensation of Furfural with Acetone Over Mg/Al Mixed Oxides. Influence of Water and Synthesis Method , 2019, Catalysts.

[13]  Yang Wang,et al.  Effects of Solvent Molecules on the Interlayer Spacing of Graphene Oxide , 2018 .

[14]  Yongqiang Cheng,et al.  Effects of sodium carbonate and potassium carbonate on colloidal properties and molecular characteristics of konjac glucomannan hydrogels. , 2018, International journal of biological macromolecules.

[15]  Zisheng Zhang,et al.  New insight into BiOX (X = Cl, Br, and I) hierarchical microspheres in photocatalysis , 2018, Materials Letters.

[16]  Yi Zhu,et al.  Facile Fabrication of BiOI/BiOCl Immobilized Films With Improved Visible Light Photocatalytic Performance , 2018, Front. Chem..

[17]  M. Kanai,et al.  Palladium-Catalyzed Synthesis of Diaryl Ketones from Aldehydes and (Hetero)Aryl Halides via C–H Bond Activation , 2018 .

[18]  Benxia Li,et al.  Understanding size-dependent properties of BiOCl nanosheets and exploring more catalysis. , 2017, Journal of colloid and interface science.

[19]  M. Gondal,et al.  Facile synthesis of light harvesting semiconductor bismuth oxychloride nano photo-catalysts for efficient removal of hazardous organic pollutants , 2017, PloS one.

[20]  Jianfang Wang,et al.  New Reaction Pathway Induced by Plasmon for Selective Benzyl Alcohol Oxidation on BiOCl Possessing Oxygen Vacancies. , 2017, Journal of the American Chemical Society.

[21]  Hu Jing,et al.  Aldol condensation of acetic acid with formaldehyde to acrylic acid over SiO2-, SBA-15-, and HZSM-5-supported V-P-O catalysts , 2016 .

[22]  Mathieu Pucheault,et al.  Highly Efficient Hosomi‐Sakurai Reaction of Aromatic Aldehydes Catalyzed by Montmorillonite Doped with Simple Bismuth(III) Salts. Batch and Continuous Flow Studies. , 2016 .

[23]  Xitian Zhang,et al.  Visible/near-IR-light-driven TNFePc/BiOCl organic-inorganic heterostructures with enhanced photocatalytic activity. , 2016, Dalton transactions.

[24]  M. S. Veitía,et al.  An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones , 2015, SpringerPlus.

[25]  G. Lemière,et al.  Cycloisomerization of allene-enol ethers under Bi(OTf)3 catalysis. , 2015, Organic letters.

[26]  Surisa Tuengpanya,et al.  Bi(OTf)3-Catalyzed One-Step Catalytic Synthesis of N-Boc or N-Cbz Protected α-Branched Amines. , 2015, The Journal of organic chemistry.

[27]  K. Takai,et al.  Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers. , 2014, Organic letters.

[28]  Lei He,et al.  Solvothermal synthesis of BiOCl flower-like hierarchical structures with high photocatalytic activity , 2014 .

[29]  Thierry Ollevier New trends in bismuth-catalyzed synthetic transformations. , 2013, Organic & biomolecular chemistry.

[30]  G. Luo,et al.  A Convenient Synthesis of α,α’-Bis(substituted benzylidene)cycloalkanones Catalyzed by Y(TFA)3 , 2012 .

[31]  Jing Jiang,et al.  Synthesis and facet-dependent photoreactivity of BiOCl single-crystalline nanosheets. , 2012, Journal of the American Chemical Society.

[32]  A. Rahman,et al.  A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones , 2012, Molecules.

[33]  G. Cheng,et al.  Well-crystallized square-like 2D BiOCl nanoplates: mannitol-assisted hydrothermal synthesis and improved visible-light-driven photocatalytic performance , 2011 .

[34]  P. Brault,et al.  BiOCl nano/microstructures on substrates: Synthesis and photocatalytic properties , 2011 .

[35]  Suresh,et al.  An efficient green protocol for the synthesis of chalcones by a Claisen–Schmidt reaction using bismuth(III)chloride as a catalyst under solvent-free condition , 2010 .

[36]  T. Bach,et al.  Bi(OTf)3-catalyzed diastereoselective S(N)1-type reactions of chiral propargylic acetates. , 2008, Angewandte Chemie.

[37]  R. Hua Recent Advances in Bismuth-Catalyzed Organic Synthesis , 2008 .

[38]  Ralph G. Pearson,et al.  The HSAB Principle — more quantitative aspects , 1995 .