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A silicododecamolybdate/pyridinium-tetrazole hybrid molecular salt as a catalyst for the epoxidation of bio-derived olefins

2021-02Journal article Restricted access
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dc.contributor.authorNunes, Martinique S.
dc.contributor.authorNeves, Patricia
dc.contributor.authorGomes, Ana C.
dc.contributor.authorCunha-Silva, Luis
dc.contributor.authorLopes, Andre D.
dc.contributor.authorValente, Anabela A.
dc.contributor.authorPillinger, Martyn
dc.contributor.authorGoncalves, Isabel S.
dc.date.accessioned2021-09-08T10:58:08Z
dc.date.available2021-09-08T10:58:08Z
dc.date.issued2021-02
dc.description.abstractThe hybrid polyoxometalate (POM) salt (Hptz)(4)[SiMo12O40].nH(2)O (1) (ptz = 5-(2-pyridyl)tetrazole) has been prepared, characterized by X-ray crystallography, and examined as a catalyst for the epoxidation of cis-cyclooctene (Cy) and bio-derived olefins, namely dl-limonene (Lim; a naturally occurring monoterpene found in the rinds of citrus fruits), methyl oleate and methyl linoleate (fatty acid methyl esters (FAMEs) obtained by transesterification of vegetable oils). The crystal structure of 1 consists of alpha-Keggin-type heteropolyanions, [SiMo12O40](4-), surrounded by space-filling and charge-balancing 2-(tetrazol-5-yl)pyridinium (Hptz(+)) cations, as well as by a large number of water molecules of crystallization (n = 9). The water molecules mediate an extensive three-dimensional (3D) hydrogen-bonding network involving the inorganic anions and organic cations. For the epoxidation of the model substrate Cy in a nonaqueous system (tert-butylhydroperoxide as oxidant), the catalytic performance of 1 (100% epoxide yield at 24 h, 70 degrees C) was superior to that of the tetrabutylammonium salt (Bu4N)(4) [SiMo12O40] (2) (63% epoxide yield at 24 h), illustrating the role of the counterion Hptz(+) in enhancing catalytic activity. The hybrid salt 1 was effective for the epoxidation of Lim (69%/85% conversion at 6 h/24 h) and the FAMEs (87-88%/100% conversion at 6 h/24 h), leading to useful bio-based products (epoxides, diepoxides and diol products).
dc.description.sponsorshipPOCI-010145-FEDER-030075
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1016/j.ica.2020.120129
dc.identifier.issn0020-1693
dc.identifier.urihttp://hdl.handle.net/10400.1/17041
dc.language.isoeng
dc.peerreviewedyes
dc.publisherELSEVIER SCIENCE SA
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO-Aveiro Institute of Materials
dc.relationInternational comparisons of product supply chains in the agro-food sectors: determinants of their competitiveness and performance on EU and international markets
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.subjectPolyoxometalate
dc.subjectInorganic-organic hybrid
dc.subjectPyridinium
dc.subjectHydrogen bonds
dc.subjectEpoxidation
dc.subjectBio-olefins
dc.subject.otherChemistry
dc.titleA silicododecamolybdate/pyridinium-tetrazole hybrid molecular salt as a catalyst for the epoxidation of bio-derived olefins
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleInternational comparisons of product supply chains in the agro-food sectors: determinants of their competitiveness and performance on EU and international markets
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
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/EC/FP7/312029/EU
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.citation.startPage120129
oaire.citation.titleInorganica Chimica Acta
oaire.citation.volume516
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamFP7
oaire.fundingStream6817 - DCRRNI ID
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/10.13039/501100008530
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.nameEuropean Commission
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccess
rcaap.typearticle
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