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

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.creatorTorrezan, Guilherme Silva [UNESP]-
Autor(es): dc.creatorPolaquini, Carlos Roberto [UNESP]-
Autor(es): dc.creatorLima, Marcelo Freitas [UNESP]-
Autor(es): dc.creatorRegasini, Luis Octavio [UNESP]-
Data de aceite: dc.date.accessioned2022-02-22T00:25:27Z-
Data de disponibilização: dc.date.available2022-02-22T00:25:27Z-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2020-06-01-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.scp.2020.100250-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/198754-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/198754-
Descrição: dc.descriptionGlycerol 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.-
Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionSão Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences (Ibilce), São José do Rio Preto, São Paulo-
Descrição: dc.descriptionSão Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences (Ibilce), São José do Rio Preto, São Paulo-
Descrição: dc.descriptionFAPESP: 2014/18330-0-
Descrição: dc.descriptionFAPESP: 2018/15083-2-
Descrição: dc.descriptionCNPq: 306251/2016-7-
Descrição: dc.descriptionCNPq: 309957/2019-2-
Descrição: dc.descriptionCNPq: 429322/2018-6-
Descrição: dc.descriptionCNPq: 471129/2013-5-
Idioma: dc.languageen-
Relação: dc.relationSustainable Chemistry and Pharmacy-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectBiodiesel-
Palavras-chave: dc.subjectGlycerol-
Palavras-chave: dc.subjectKetones-
Palavras-chave: dc.subjectProtic solvents-
Título: dc.titleUse of glycerol, waste glycerol from biodiesel production and other protic solvents in bioactive α,β-unsaturated ketones synthesis-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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