Use of glycerol, waste glycerol from biodiesel production and other protic solvents in bioactive α,β-unsaturated ketones synthesis

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dc.contributor.authorTorrezan, Guilherme Silva [UNESP]
dc.contributor.authorPolaquini, Carlos Roberto [UNESP]
dc.contributor.authorLima, Marcelo Freitas [UNESP]
dc.contributor.authorRegasini, Luis Octavio [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2020-12-12T01:21:11Z
dc.date.available2020-12-12T01:21:11Z
dc.date.issued2020-06-01
dc.description.abstractGlycerol is the main co-product from biodiesel production and has been recognized as a sustainable solvent. Herein, we used glycerol and waste glycerol in synthesis of two bioactive α,β-unsaturated ketones (E,E)-1,5-diphenylpenta-2,4-dien-1-one (1) and (E,E)-2,6-dibenzylidenecyclohexanone (2), using aldol mono- and di-condensation reactions, respectively. Crude yield values were calculated from product mass after precipitation and drying. Purity was measured by High Performance Liquid Chromatography with Photodiode Array (HPLC-PAD) using analytical curves and reference compounds. Glycerol and waste glycerol were able to furnish 1 and 2 in higher crude yields and HPLC-PAD purities values than other protic solvents (ethanol, methanol, PEG-400 and water). In order to investigate reasons of glycerol efficiency when compared to water efficiency, we performed computational calculations using Density Functional Theory (DFT). Theoretical predictions confirmed the E1cB mechanism, as well as favourable energy barrier using glycerol in comparison to water, corroborating their sustainable properties. In addition, waste glycerol from corn and sunflower oil transesterifications were used in the synthesis of 1 and 2 for four recycles, displaying good crude yields and HPLC-purities.en
dc.description.affiliationSão Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences (Ibilce), São José do Rio Preto, São Paulo
dc.description.affiliationUnespSão Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences (Ibilce), São José do Rio Preto, São Paulo
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipIdFAPESP: 2014/18330-0
dc.description.sponsorshipIdFAPESP: 2018/15083-2
dc.description.sponsorshipIdCNPq: 306251/2016-7
dc.description.sponsorshipIdCNPq: 309957/2019-2
dc.description.sponsorshipIdCNPq: 429322/2018-6
dc.description.sponsorshipIdCNPq: 471129/2013-5
dc.identifierhttp://dx.doi.org/10.1016/j.scp.2020.100250
dc.identifier.citationSustainable Chemistry and Pharmacy, v. 16.
dc.identifier.doi10.1016/j.scp.2020.100250
dc.identifier.issn2352-5541
dc.identifier.scopus2-s2.0-85083587877
dc.identifier.urihttp://hdl.handle.net/11449/198754
dc.language.isoeng
dc.relation.ispartofSustainable Chemistry and Pharmacy
dc.sourceScopus
dc.subjectBiodiesel
dc.subjectGlycerol
dc.subjectKetones
dc.subjectProtic solvents
dc.titleUse of glycerol, waste glycerol from biodiesel production and other protic solvents in bioactive α,β-unsaturated ketones synthesisen
dc.typeArtigo

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