{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,14]],"date-time":"2026-05-14T07:50:00Z","timestamp":1778745000385,"version":"3.51.4"},"reference-count":103,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2021,3,17]],"date-time":"2021-03-17T00:00:00Z","timestamp":1615939200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/QUI\/00100\/2019-BL\/CQE-2017-022"],"award-info":[{"award-number":["UID\/QUI\/00100\/2019-BL\/CQE-2017-022"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The selective oxidation of styrene under heterogeneous catalyzed conditions delivers environmentally friendly paths for the production of benzaldehyde, an important intermediate for the synthesis of several products. The present review explores heterogeneous catalysts for styrene oxidation using a variety of metal catalysts over the last decade. The use of several classes of supports is discussed, including metal\u2013organic frameworks, zeolites, carbon materials and silicas, among others. The studied catalytic systems propose as most used oxidants tert-butyl hydroperoxide, and hydrogen peroxide and mild reaction conditions. The reaction mechanism proceeds through the generation of an intermediate reactive metal\u2013oxygen species by catalyst-oxidant interactions. Overall, most of the studies highlight the synergetic effects among the metal and support for the activity and selectivity enhancement.<\/jats:p>","DOI":"10.3390\/molecules26061680","type":"journal-article","created":{"date-parts":[[2021,3,17]],"date-time":"2021-03-17T11:48:22Z","timestamp":1615981702000},"page":"1680","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":63,"title":["Selective Styrene Oxidation to Benzaldehyde over Recently Developed Heterogeneous Catalysts"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7603-5192","authenticated-orcid":false,"given":"Marta A.","family":"Andrade","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural and Departamento de Engenharia Qu\u00edmica, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisbn, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5403-9352","authenticated-orcid":false,"given":"Lu\u00edsa M. D. R. S.","family":"Martins","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural and Departamento de Engenharia Qu\u00edmica, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisbn, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,3,17]]},"reference":[{"key":"ref_1","first-page":"223","article-title":"Benzaldehyde","volume":"Volume 5","author":"Bruhne","year":"2012","journal-title":"Ullmann\u2019s Encyclopedia of Industrial Chemistry"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.apcata.2004.09.001","article-title":"Styrene oxidation with H2O2 over Ti-containing molecular sieves with MFI, BEA and MCM-41 topologies","volume":"277","author":"Hulea","year":"2004","journal-title":"Appl. Catal. A Gen."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"4039","DOI":"10.1021\/ja993472q","article-title":"A novel epoxidation reaction of olefins using a combination of chloramine-M, benzaldehyde, and benzyltriethylammonium chloride","volume":"122","author":"Yang","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.apcata.2011.04.021","article-title":"Studies on styrene selective oxidation to benzaldehyde catalyzed by Cr-ZSM-5: Reaction parameters effects and kinetics","volume":"400","author":"Saux","year":"2011","journal-title":"Appl. Catal. A Gen."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.apcata.2012.11.046","article-title":"Synthesis and characterization of MEL and FAU zeolites doped with transition metals for their application to the fine chemistry under microwave irradiation","volume":"453","author":"Polaert","year":"2013","journal-title":"Appl. Catal. A Gen."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1002\/anie.201101182","article-title":"Polymeric graphitic carbon nitride as a heterogeneous organocatalyst: From photochemistry to multipurpose catalysis to sustainable chemistry","volume":"51","author":"Wang","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.inoche.2012.07.002","article-title":"A recyclable polymer anchored copper(II) catalyst for oxidation reaction of olefins and alcohols with tert-butylhydroperoxide in aqueous medium","volume":"24","author":"Islam","year":"2012","journal-title":"Inorg. Chem. Commun."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Furukawa, H., Cordova, K.E., O\u2019Keeffe, M., and Yaghi, O.M. (2013). The chemistry and applications of metal-organic frameworks. Science, 341.","DOI":"10.1126\/science.1230444"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1021\/ie2020608","article-title":"Solvent free selective oxidation of styrene and benzyl alcohol to benzaldehyde over an eco-friendly and reusable catalyst, undecamolybdophosphate supported onto neutral alumina","volume":"51","author":"Patel","year":"2012","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_10","first-page":"11636","article-title":"Recent developments in heterogeneous catalyzed epoxidation of styrene to styrene oxide","volume":"4","author":"Batra","year":"2019","journal-title":"Chem. Sel."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"7568","DOI":"10.1021\/ic800538r","article-title":"High-throughput assisted rationalization of the formation of metal organic frameworks in the iron(III) aminoterephthalate solvothermal system","volume":"47","author":"Bauer","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2334","DOI":"10.1002\/anie.200300610","article-title":"Functional porous coordination polymers","volume":"43","author":"Kitagawa","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.ccr.2019.03.005","article-title":"Functional metal\u2013organic frameworks for catalytic applications","volume":"388","author":"Xu","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1016\/j.ccr.2015.08.002","article-title":"Application of metal and metal oxide nanoparticles at MOFs","volume":"307","author":"Falcaro","year":"2016","journal-title":"Coord. Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2599","DOI":"10.1039\/C4CY00152D","article-title":"A reusable CuII based metal-organic framework as a catalyst for the oxidation of olefins","volume":"4","author":"Cancino","year":"2014","journal-title":"Catal. Sci. Technol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0022-2860(03)00349-1","article-title":"Hydrothermal synthesis and crystal structure of an infinite 1D ladderlike metal-organic compound: [Cu2(btec)(2,2\u2032-bipy)2] \u221e (btec = 1,2,4,5-benzenetetracarboxylate)","volume":"697","author":"Hao","year":"2004","journal-title":"J. Mol. Struct."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1016\/j.jcat.2004.03.006","article-title":"Liquid-phase epoxidation of olefins by manganese oxide octahedral molecular sieves","volume":"224","author":"Ghosh","year":"2004","journal-title":"J. Catal."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/j.cej.2016.04.102","article-title":"Tunable catalytic properties of multi-metal-organic frameworks for aerobic styrene oxidation","volume":"299","author":"Fu","year":"2016","journal-title":"Chem. Eng. J."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Deng, H., Doonan, C.J., Furukawa, H., Ferreira, R.B., Towne, J., Knobler, C.B., Wang, B., and Yaghi, O.M. (2010). Ratios in Metal-Organic Frameworks. Science, 846\u2013851.","DOI":"10.1126\/science.1181761"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5881","DOI":"10.1021\/ic500434a","article-title":"Synthesis and characterization of metal-organic framework-74 containing 2, 4, 6, 8, and 10 different metals","volume":"53","author":"Wang","year":"2014","journal-title":"Inorg. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2040","DOI":"10.1126\/science.1116275","article-title":"A Chromium terephthalate-based solid with unusually large pore volumes and surface area","volume":"309","author":"Ferey","year":"2005","journal-title":"Science"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.catcom.2017.08.017","article-title":"Mn-MIL-100 heterogeneous catalyst for the selective oxidative cleavage of alkenes to aldehydes","volume":"103","author":"Ha","year":"2018","journal-title":"Catal. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2820","DOI":"10.1039\/B704325B","article-title":"Synthesis and catalytic properties of MIL-100(Fe), an iron(III) carboxylate with large pores","volume":"100","author":"Horcajada","year":"2007","journal-title":"Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"544","DOI":"10.1039\/C2CE26436F","article-title":"Formation and characterisation of Mn-MIL-100","volume":"15","author":"Reinsch","year":"2013","journal-title":"Cryst. Eng. Comm."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5512","DOI":"10.1002\/anie.201701604","article-title":"Multi-shelled hollow metal\u2013organic frameworks","volume":"56","author":"Liu","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"9237","DOI":"10.1002\/anie.201004745","article-title":"Hollow ferrocenyl coordination polymer microspheres with micropores in shells prepared by ostwald ripening","volume":"49","author":"Huo","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/advs.201802365","article-title":"One-step construction of hydrophobic MOFs@COFs core\u2013shell composites for heterogeneous selective catalysis","volume":"6","author":"Cai","year":"2019","journal-title":"Adv. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/adma.201705454","article-title":"Hybridization of MOFs and COFs: A new strategy for construction of MOF@COF core\u2013shell hybrid materials","volume":"30","author":"Peng","year":"2018","journal-title":"Adv. Mater."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1148","DOI":"10.1126\/science.283.5405.1148","article-title":"A chemically functionalizable nanoporous material [Cu3(TMA)2 (H2O)3](n)","volume":"283","author":"Chui","year":"1999","journal-title":"Science"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5289","DOI":"10.1021\/acsanm.8b01283","article-title":"2-Methylimidazole-assisted synthesis of nanosized Cu3(BTC)2 for controlling the selectivity of the catalytic oxidation of styrene","volume":"1","author":"Guo","year":"2018","journal-title":"ACS Appl. Nano Mater."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"17272","DOI":"10.1039\/C6CP01243D","article-title":"Looking inside the pores of a MCM-41 based Mo heterogeneous styrene oxidation catalyst: An inelastic neutron scattering study","volume":"18","author":"Fernandes","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1016\/j.apcata.2017.12.010","article-title":"Catalytic evaluation of mesoporous metal oxides for liquid phase oxidation of styrene","volume":"552","author":"Masunga","year":"2018","journal-title":"Appl. Catal. A Gen."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1002\/tcr.201100002","article-title":"Nanoscale polyoxometalate-based inorganic\/organic hybrids","volume":"11","author":"Song","year":"2011","journal-title":"Chem. Rec."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4109","DOI":"10.1021\/acs.inorgchem.8b00282","article-title":"Polyoxometalate-based metal-organic frameworks for selective oxidation of aryl alkenes to aldehydes","volume":"57","author":"Ma","year":"2018","journal-title":"Inorg. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"6324","DOI":"10.1021\/acscatal.6b01753","article-title":"Impact of linker engineering on the catalytic activity of metal-organic frameworks containing Pd(II)-bipyridine complexes","volume":"6","author":"Li","year":"2016","journal-title":"ACS Catal."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3978","DOI":"10.1039\/C4GC00314D","article-title":"A molecular Pd(ii) complex incorporated into a MOF as a highly active single-site heterogeneous catalyst for C-Cl bond activation","volume":"16","author":"Chen","year":"2014","journal-title":"Green Chem."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Zhang, Y., Wei, N., Xing, Z., and Han, Z.B. (2020). Functional hexanuclear Y(III) cluster-based MOFs supported Pd(II) single site catalysts for aerobic selective oxidation of styrene. Appl. Catal. A Gen., 602.","DOI":"10.1016\/j.apcata.2020.117668"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1016\/S0021-9517(02)00132-X","article-title":"State of the art and future challenges of zeolites as catalysts","volume":"216","author":"Corma","year":"2003","journal-title":"J. Catal."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"896","DOI":"10.1021\/cr040204o","article-title":"Mesopore-modified zeolites: Preparation, characterization, and applications","volume":"106","author":"Tao","year":"2006","journal-title":"Chem. Rev."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1002\/cssc.201500124","article-title":"Hierarchical zeolites and their catalytic performance in selective oxidative processes","volume":"8","author":"Ojeda","year":"2015","journal-title":"Chem. Sus. Chem."},{"key":"ref_41","unstructured":"Aliofkhazraei, M. (2015). Hierarchical zeolites: Preparation, properties and catalytic applications. Comprehensive Guide for Mesoporous Materials, Vol. 3: Properties and Development, Nova Science Publishers Inc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.catcom.2013.11.020","article-title":"Optimized benzaldehyde production over a new Co-ZSM-11 catalyst: Reaction parameters effects and kinetics","volume":"46","author":"Polaert","year":"2014","journal-title":"Catal. Commun."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1007\/s10934-016-0129-8","article-title":"Hierarchical ZSM-5 catalytic performance evaluated in the selective oxidation of styrene to benzaldehyde using TBHP","volume":"23","author":"Narayanan","year":"2016","journal-title":"J. Porous Mater."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"907","DOI":"10.1007\/s10934-015-9964-2","article-title":"Synthesis of hierarchical ZSM-5 hexagonal cubes and their catalytic activity in the solvent-free selective oxidation of toluene","volume":"22","author":"Narayanan","year":"2015","journal-title":"J. Porous Mater."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/j.molcata.2016.08.031","article-title":"Studies of styrene oxidation by catalyst based on zeolite-Y nanohybrid materials","volume":"424","author":"Desai","year":"2016","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1016\/j.molcata.2014.08.022","article-title":"Catalytic oxidation of limonene over zeolite-Y entrapped oxovanadium (IV) complexes as heterogeneous catalysts","volume":"395","author":"Modi","year":"2014","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.jcis.2018.01.113","article-title":"Highly selective oxidation of styrene to benzaldehyde over a tailor-made cobalt oxide encapsulated zeolite catalyst","volume":"517","author":"Liu","year":"2018","journal-title":"J. Colloid Interface Sci."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1086","DOI":"10.1002\/cjce.23307","article-title":"Cleavage of double bond using metal-loaded ZSM-5 zeolite catalysts for renewable biochemical application","volume":"97","author":"Hoang","year":"2019","journal-title":"Can. J. Chem. Eng."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1016\/j.micromeso.2017.10.043","article-title":"Zeolite-Y entrapped metallo-pyrazolone complexes as heterogeneous catalysts: Synthesis, catalytic aptitude and computational investigation","volume":"261","author":"Modi","year":"2018","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/j.micromeso.2018.08.023","article-title":"Synthesis of ANA-zeolite-based Cu nanoparticles composite catalyst and its regularity in styrene oxidation","volume":"274","author":"Gu","year":"2019","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1265","DOI":"10.1039\/C5CY01437A","article-title":"Metal-supported carbon-based materials: Opportunities and challenges in the synthesis of valuable products","volume":"6","author":"Soriano","year":"2016","journal-title":"Catal. Sci. Technol."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1080\/01614940.2010.498748","article-title":"Last decade of research on activated carbons as catalytic support in chemical processes","volume":"52","year":"2010","journal-title":"Catal. Rev. Sci. Eng."},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Mestre, A.S., and Carvalho, A.P. (2018). Nanoporous carbon synthesis: An old story with exciting new chapters. Porosity-Process, Technologies and Applications, IntechOpen.","DOI":"10.5772\/intechopen.72476"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1263","DOI":"10.1002\/ajoc.201900259","article-title":"Carbon-support-based heterogeneous nanocatalysts: Synthesis and Applications in organic reactions","volume":"8","author":"Bahuguna","year":"2019","journal-title":"Asian J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"6816","DOI":"10.1039\/C6DT00514D","article-title":"Highly efficient and reusable CNT supported iron(II) catalyst for microwave assisted alcohol oxidation","volume":"45","author":"Martins","year":"2016","journal-title":"Dalt. Trans."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.apcata.2015.01.005","article-title":"Oxido vanadium complexes with tridentate aroylhydrazone as catalyst precursors for solvent-free microwave-assisted oxidation of alcohols","volume":"493","author":"Sutradhar","year":"2015","journal-title":"Appl. Cat. A Gen."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3056","DOI":"10.1039\/c3cy00552f","article-title":"Homogeneous and heterogenised new gold C-scorpionate complexes as catalysts for cyclohexane oxidation","volume":"3","author":"Martins","year":"2013","journal-title":"Catal. Sci. Technol."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1016\/j.apcata.2013.07.035","article-title":"Gold nanoparticles supported on carbon materials for cyclohexane oxidation with hydrogen peroxide","volume":"467","author":"Carabineiro","year":"2013","journal-title":"Appl. Catal. A Gen."},{"key":"ref_59","first-page":"1821","article-title":"Heterogenized C-scorpionate iron(II) complex on nanostructured carbon materials as recyclable catalysts for microwave-assisted oxidation reactions","volume":"10","author":"Ribeiro","year":"2018","journal-title":"Chem. Cat. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.cattod.2019.05.050","article-title":"Commercial gold(III) complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation","volume":"357","author":"Pakrieva","year":"2020","journal-title":"Catal. Today"},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Matias, A.S., Ribeiro, A.P.C., and Martins, M.D.R.S. (2020). Molecules selective oxidation of ethane to acetic acid selective oxidation of ethane to acetic acid catalyzed by a c-scorpionate iron(II) complex: Homogeneous vs. heterogeneous. Molecules, 25.","DOI":"10.3390\/molecules25235642"},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Serp, P., and Figueiredo, J.L. (2009). Carbon as catalyst. Carbon Materials for Catalysis, John Wiley & Sons Inc.","DOI":"10.1002\/9780470403709"},{"key":"ref_63","unstructured":"Bandosz, T.J. (2006). Surface chemistry of carbon materials. Activated Carbon Surfaces in Environmental Remediation, Elsevier."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1039\/C1CY00361E","article-title":"Graphene-based materials for catalysis","volume":"2","author":"Machado","year":"2012","journal-title":"Catal. Sci. Technol."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.inoche.2012.11.017","article-title":"Catalytic activity of carbon nanotube supported iron(III) and manganese(III) porphyrins in oxidation of olefins with tert-butyl hydroperoxide: Higher activity of the iron(III) porphyrin","volume":"29","author":"Rayati","year":"2013","journal-title":"Inorg. Chem. Commun."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3145","DOI":"10.1021\/ja01069a035","article-title":"Mechanistic investigations of porphyrin syntheses. I. Preliminary studies on ms-tetraphenylporphin","volume":"86","author":"Adler","year":"1964","journal-title":"J. Am. Chem. Soc."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1002\/jlac.19717450117","article-title":"Metallkomplexe mit tetrapyrrol-liganden, III. Darstellung von metallkomplexen des octa\u00e4thylporphins aus metall-acetylacetonaten","volume":"745","author":"Buchler","year":"1971","journal-title":"Justus Liebigs Ann. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1016\/S1872-2067(14)60314-4","article-title":"Oxidation of styrene to benzaldehyde by p-toluenesulfonic acid using hydrogen peroxide in the presence of activated carbon","volume":"36","author":"Li","year":"2015","journal-title":"Cuihua Xuebao Chin. J. Catal."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"13565","DOI":"10.1039\/C8DT02765J","article-title":"Noble metal-free V2O5\/g-C3N4 composites for selective oxidation of olefins using hydrogen peroxide as an oxidant","volume":"47","author":"Zou","year":"2018","journal-title":"Dalt. Trans."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"8090","DOI":"10.1021\/acscatal.7b02335","article-title":"Metal\/porous carbon composites for heterogeneous catalysis: Old catalysts with improved performance promoted by N-doping","volume":"7","author":"Cao","year":"2017","journal-title":"ACS Catal."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.cattod.2019.04.044","article-title":"Styrene oxidation catalyzed by copper(II) C-scorpionates in homogenous medium and immobilized on sucrose derived hydrochars","volume":"357","author":"Duarte","year":"2020","journal-title":"Catal. Today"},{"key":"ref_72","unstructured":"Andrade, M.A., Mestre, A.S., Carvalho, A.P., Pombeiro, A.J.L., and Martins, L.M.D.R.S. (2019). The role of nanoporous carbon materials in catalytic cyclohexane oxidation. Catal. Today, 1\u201310."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"1217","DOI":"10.1351\/PAC-CON-08-10-08","article-title":"Scorpionate V(III-V) complexes as catalyst precursors for solvent-free cyclohexane oxidation with dioxygen","volume":"81","author":"Mishra","year":"2009","journal-title":"Pure Appl. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"758","DOI":"10.1016\/j.crci.2015.03.018","article-title":"Catalytic oxidation of cyclohexane with hydrogen peroxide and a tetracopper(II) complex in an ionic liquid","volume":"18","author":"Ribeiro","year":"2015","journal-title":"C. R. Chim."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1947","DOI":"10.1016\/j.jorganchem.2004.11.005","article-title":"Syntheses and properties of Re(III) complexes derived from hydrotris(1-pyrazolyl)methanes. Molecular structure of [ReCl2(HCpz3)(PPh3)][BF4]","volume":"690","author":"Alegria","year":"2005","journal-title":"J. Organomet. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"2285","DOI":"10.1039\/C8CY00136G","article-title":"Ultra-fast and selective oxidation of styrene to benzaldehyde catalyzed by a C-scorpionate Cu(II) complex","volume":"8","author":"Duarte","year":"2018","journal-title":"Catal. Sci. Technol."},{"key":"ref_77","doi-asserted-by":"crossref","unstructured":"Lashanizadegan, M., Nikoofar, K., Aghaei, A., Mehrikaram, F., and Mirzazadeh, H. (2019). Immobilized Cu(II) and Co(II) Schiff base complexes on the surface of functionalized magnetized multiwalled carbon nanotubes: Novel catalysts for oxidation and solvent-free pseudo six-component condensation reaction. Solid State Sci., 95.","DOI":"10.1016\/j.solidstatesciences.2019.105937"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"106122","DOI":"10.1016\/j.solidstatesciences.2020.106122","article-title":"Selective oxidation of styrene to benzaldehyde by cobalt phthalocyanine-multi-walled carbon nanotube composites","volume":"101","author":"Wang","year":"2020","journal-title":"Solid State Sci."},{"key":"ref_79","doi-asserted-by":"crossref","unstructured":"Saini, D., Aggarwal, R., Anand, S.R., Satrawala, N., Joshi, R.K., and Sonkar, S.K. (2020). Sustainable feasibility of waste printer ink to magnetically separable iron oxide\u2013doped nanocarbons for styrene oxidation. Mater. Today Chem., 16.","DOI":"10.1016\/j.mtchem.2020.100256"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"24363","DOI":"10.1039\/C4RA13077D","article-title":"Mesoporous material: A versatile support in heterogeneous catalysis for the liquid phase catalytic transformations","volume":"5","author":"Pal","year":"2015","journal-title":"RSC Adv."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/S0920-5861(01)00507-7","article-title":"New trends in the design of supported catalysts on mesoporous silicas and their applications in fine chemicals","volume":"73","author":"Brunel","year":"2002","journal-title":"Catal. Today"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"2373","DOI":"10.1021\/cr960406n","article-title":"From microporous to mesoporous molecular sieve materials and their use in catalysis","volume":"97","author":"Corma","year":"1997","journal-title":"Chem. Rev."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.micromeso.2004.06.030","article-title":"Ordered mesoporous materials in catalysis","volume":"77","author":"Taguchi","year":"2005","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1716","DOI":"10.1016\/S1872-2067(14)60131-5","article-title":"Catalytic oxidation of styrene to benzaldehyde over a copper Schiff-base\/SBA-15 catalyst","volume":"35","author":"Zhu","year":"2014","journal-title":"Chin. J. Catal."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1007\/s10562-011-0668-1","article-title":"Oxidative cleavage of C=C bond of styrene and its derivatives with H2O2 using vanadyl(IV) acetylacetonate anchored SBA-15 catalyst","volume":"141","author":"Anand","year":"2011","journal-title":"Catal. Lett."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"50832","DOI":"10.1039\/C4RA08333D","article-title":"Spherical V-MCM-48: The synthesis, characterization and catalytic performance in styrene oxidation","volume":"4","author":"Wang","year":"2014","journal-title":"RSC Adv."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/j.jssc.2014.10.008","article-title":"Synthesis of cobalt-containing mesoporous catalysts using the ultrasonic-assisted \u201cpH-adjusting\u201d method: Importance of cobalt species in styrene oxidation","volume":"221","author":"Li","year":"2015","journal-title":"J. Solid State Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/j.jssc.2016.01.018","article-title":"Functionalized SBA-15 supported nickel (II)-oxime-imine catalysts for liquid phase oxidation of olefins under solvent-free conditions","volume":"237","author":"Paul","year":"2016","journal-title":"J. Solid State Chem."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"227","DOI":"10.17159\/0379-4350\/2016\/v69a29","article-title":"Heterogeneous oxidation of alkenes: The role of silica-supported bimetallic and trimetallic catalysts","volume":"69","author":"Parekh","year":"2016","journal-title":"S. Afr. J. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.catcom.2013.06.008","article-title":"Mixed Cu-Ni-Co nano-metal oxides: A new class of catalysts for styrene oxidation","volume":"40","author":"Valand","year":"2013","journal-title":"Catal. Commun."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1007\/s11144-016-1024-7","article-title":"Oxidation of styrene to benzaldehyde with hydrogen peroxide in the presence of catalysts obtained by the immobilization of H3PW12O40 on SBA-15 mesoporous material","volume":"119","author":"Sun","year":"2016","journal-title":"React. Kinet. Mech. Catal."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"606","DOI":"10.1016\/j.jcis.2019.06.042","article-title":"Hierarchical hollow nickel silicate microflowers for selective oxidation of styrene","volume":"553","author":"Liu","year":"2019","journal-title":"J. Colloid Interface Sci."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1670","DOI":"10.1166\/jnn.2020.17137","article-title":"Catalytic activity of Ag-Co-MCM-41 for liquid-phase selective oxidation of styrene to benzaldehyde","volume":"20","author":"Jiang","year":"2019","journal-title":"J. Nanosci. Nanotechnol."},{"key":"ref_94","doi-asserted-by":"crossref","unstructured":"Andas, J., Ekhbal, S.H., and Ali, T.H. (2021). MCM-41 modified heterogeneous catalysts from rice husk for selective oxidation of styrene into benzaldehyde. Environ. Technol. Innov., 21.","DOI":"10.1016\/j.eti.2020.101308"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"474","DOI":"10.1016\/j.jcat.2016.10.003","article-title":"Selective oxidation of styrene catalyzed by cerium-doped cobalt ferrite nanocrystals with greatly enhanced catalytic performance","volume":"344","author":"Tong","year":"2016","journal-title":"J. Catal."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.catcom.2018.08.002","article-title":"A green methodology for the selective catalytic oxidation of styrene by magnetic metal-transition ferrite nanoparticles","volume":"116","author":"Martins","year":"2018","journal-title":"Catal. Commun."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"16793","DOI":"10.1007\/s10854-020-04234-5","article-title":"Nanocrystalline cerium-doped Y-type barium hexaferrite; a useful catalyst for selective oxidation of styrene","volume":"31","author":"Suthar","year":"2020","journal-title":"J. Mater. Sci. Mater. Electron."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.catcom.2018.10.016","article-title":"Selective styrene oxidation on alkaline tantalates ATaO3 (A = Li, Na, K) as heterogeneous catalysts","volume":"119","author":"Pecchi","year":"2019","journal-title":"Catal. Commun."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"27755","DOI":"10.1039\/C9RA04892H","article-title":"Flexible oxidation of styrene using TBHP over zirconia supported mono-copper substituted phosphotungstate","volume":"9","author":"Sadasivan","year":"2019","journal-title":"RSC Adv."},{"key":"ref_100","doi-asserted-by":"crossref","unstructured":"Ito, S., Kon, Y., Nakashima, T., Hong, D., Konno, H., Ino, D., and Sato, K. (2019). Titania-catalyzed H2O2 thermal oxidation of styrenes to aldehydes. Molecules, 24.","DOI":"10.3390\/molecules24142520"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"2521","DOI":"10.1080\/00958972.2020.1821881","article-title":"Keggin-type polyoxometalate-based supramolecular complex for selective oxidation of styrene to benzaldehyde","volume":"73","author":"Cui","year":"2020","journal-title":"J. Coord. Chem."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"5803","DOI":"10.1021\/acs.inorgchem.0c00072","article-title":"A Bicadmium-substituted polyoxometalate network based on a vanadosilicate cluster for the selective oxidation of styrene to benzaldehyde","volume":"59","author":"Zhang","year":"2020","journal-title":"Inorg. Chem."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"16776","DOI":"10.1039\/D0NJ03907A","article-title":"Visible-light-driven photochemical activity of ternary Ag\/AgBr\/TiO2 nanotubes for oxidation C(sp3)-H and C(sp2)-H bonds","volume":"44","author":"Dehghani","year":"2020","journal-title":"New J. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/6\/1680\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:37:05Z","timestamp":1760161025000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/6\/1680"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,3,17]]},"references-count":103,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2021,3]]}},"alternative-id":["molecules26061680"],"URL":"https:\/\/doi.org\/10.3390\/molecules26061680","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,3,17]]}}}