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A Molybdenum(VI) Complex of 5-(2-pyridyl-1-oxide)tetrazole: synthesis, structure, and transformation into a MoO3-Based hybrid catalyst for the epoxidation of Bio-Olefins

2023-03-10Journal article Open Access
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dc.contributor.authorNunes, Martinique S.
dc.contributor.authorGomes, Diana M.
dc.contributor.authorGomes, Ana C.
dc.contributor.authorNeves, Patrícia
dc.contributor.authorMendes, Ricardo F.
dc.contributor.authorPaz, Filipe A. Almeida
dc.contributor.authorLopes, Andre D.
dc.contributor.authorPillinger, Martyn
dc.contributor.authorValente, Anabela A.
dc.contributor.authorGonçalves, Isabel S.
dc.date.accessioned2023-03-29T12:43:08Z
dc.date.available2023-03-29T12:43:08Z
dc.date.issued2023-03-10
dc.date.updated2023-03-28T12:56:02Z
dc.description.abstractThe discovery of heterogeneous catalysts synthesized in easy, sustainable ways for the valorization of olefins derived from renewable biomass is attractive from environmental, sustainability, and economic viewpoints. Here, an organic–inorganic hybrid catalyst formulated as [MoO3 (Hpto)]·H2O (2), where Hpto = 5-(2-pyridyl-1-oxide)tetrazole, was prepared by a hydrolysis– condensation reaction of the complex [MoO2Cl2 (Hpto)]·THF (1). The characterization of 1 and 2 by FT-IR and Raman spectroscopies, as well as 13C solid-state NMR, suggests that the bidentate N,O-coordination of Hpto in 1 (forming a six-membered chelate ring, confirmed by X-ray crystallography) is maintained in 2, with the ligand coordinated to a molybdenum oxide substructure. Catalytic studies suggested that 2 is a rare case of a molybdenum oxide/organic hybrid that acts as a stable solid catalyst for olefin epoxidation with tert-butyl hydroperoxide. The catalyst was effective for converting biobased olefins, namely fatty acid methyl esters (methyl oleate, methyl linoleate, methyl linolenate, and methyl ricinoleate) and the terpene limonene, leading predominantly to the corresponding epoxide products with yields in the range of 85–100% after 24 h at 70 ◦C. The versatility of catalyst 2 was shown by its effectiveness for the oxidation of sulfides into sulfoxides and sulfones, at 35 ◦C (quantitative yield of sulfoxide plus sulfone, at 24 h; sulfone yields in the range of 77–86%). To the best of our knowledge, 2 is the first molybdenum catalyst reported for methyl linolenate epoxidation, and the first of the family [MoO3 (L)x] studied for methyl ricinoleate epoxidation.pt_PT
dc.description.sponsorshipLA/P/0006/2020; POCI-01-0145-FEDER-030075; ALG-01-0145-FEDER-022121; grant ref. 2021.06403.BD; grant ref. 2021.04756.BD;pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationCatalysts 13 (3): 565 (2023)pt_PT
dc.identifier.doi10.3390/catal13030565pt_PT
dc.identifier.issn2073-4344
dc.identifier.urihttp://hdl.handle.net/10400.1/19348
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO-Aveiro Institute of Materials
dc.relationNot Available
dc.relationNot Available
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectDioxomolybdenum (VI) complexespt_PT
dc.subjectMolybdenum oxidept_PT
dc.subjectOrganic–inorganic hybrid materialspt_PT
dc.subject5-(2-pyridyl-1-oxide)tetrazolept_PT
dc.subjectEpoxidationpt_PT
dc.subjectBio-olefinspt_PT
dc.subjectLimonenept_PT
dc.subjectFAMEspt_PT
dc.subjectSulfoxidationpt_PT
dc.titleA Molybdenum(VI) Complex of 5-(2-pyridyl-1-oxide)tetrazole: synthesis, structure, and transformation into a MoO3-Based hybrid catalyst for the epoxidation of Bio-Olefinspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleNot Available
oaire.awardTitleNot Available
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F02128%2F2017%2FCP1459%2FCT0039/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00553%2F2017%2FCP1459%2FCT0034/PT
oaire.citation.issue3pt_PT
oaire.citation.startPage565pt_PT
oaire.citation.title2073-4344pt_PT
oaire.citation.volume13pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamCEEC IND 2017
oaire.fundingStreamCEEC IND 2017
person.familyNameD. Lopes
person.givenNameAndré
person.identifier2824636
person.identifier.ciencia-id351E-856A-0300
person.identifier.orcid0000-0002-9702-1216
person.identifier.ridE-2136-2012
person.identifier.scopus-author-id7201958625
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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