Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFPB |
Texto Completo: | https://repositorio.ufpb.br/jspui/handle/123456789/19020 |
Resumo: | This work describes the synthesis of ten non-symmetric and four symmetric 2- oxoethylphthalate compounds, derived from potassium terephthalate, which was obtained from the depolymerization reaction of post-consumption polyethylene terephthalate (PET) bottles. The choice of post-consumer PET bottles as raw material comes from the possibility of adding value to new substances obtained from recyclable sources, which, in addition, are candidates for antibacterial and antifungal agents, as well as reducing residues in the environment. environment. The first step for both symmetrical and non-symmetric 2-Oxoethylphthalate series was through (i) preparation of potassium terephthalate (2) from the depolymerization reaction of postconsumer PET bottles (1) in 90% of Yield. Non-symmetric 2-oxoethyl terephthalates (8a-j) were synthesized through six steps: (ii) acid hydrolysis reaction of recycled potassium terephthalate (2) in 100% yield; (iii) esterification reaction of terephthalic acid (3) with methanol in 80% yield; (iv) reaction of basic monohydrolysis of methyl terephthalate (4) in 77% yield; (v) acetylation reaction of aromatic amines with chloroacetyl chloride in 76-95% yield; and (vi) alkylating the methyl terephthalate salt (5) with 2-chloro-N-arylacetamides (6a-j) in 52-98% yield. Symmetric 2- oxoethylterephthalates (9a-d) were synthesized through three steps: (ii) esterification reaction of chloroacetic acid with different alkyl alcohols in 89-93% yield; and (iii) alkylation reaction of recycled potassium terephthalate (2) with alkylated 2- chloroacetates (7a-d) in 66-78% yield. Intermediate and final compounds were characterized by IR spectroscopic techniques, 1H and 13C NMR (uni and twodimensional) and mass spectrometry (CG-MS and ESI-MS). In the 80-0.31 µg.mL-1 concentration range, the final compounds (8a-j and 9a-d) showed no antifungal (yeast and filamentous fungi) and antibacterial activity in vitro. The compounds obtained in the crystalline form (8h and 9a-b) were submitted to single crystal X-ray diffraction analysis, through which, together with the supramolecular cluster methodology and quantum mechanics calculations of the density functional theory with dispersion correction. (DFT-D, Density Functional Theory-Dispersive), with calculation level wB97X-D / cc-pVDZ, it was possible to develop a topological and energetic study to analyze the similarities and differences in crystallization mechanisms through intermolecular interactions. |
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Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumoReciclagemPETAcetamida2-oxoetiltereftalatoAvaliação antimicrobianaEstudo topológico e energéticoRecyclingAcetamide2-oxoethylterephthalateAntimicrobial evaluationTopological and energetic studyCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThis work describes the synthesis of ten non-symmetric and four symmetric 2- oxoethylphthalate compounds, derived from potassium terephthalate, which was obtained from the depolymerization reaction of post-consumption polyethylene terephthalate (PET) bottles. The choice of post-consumer PET bottles as raw material comes from the possibility of adding value to new substances obtained from recyclable sources, which, in addition, are candidates for antibacterial and antifungal agents, as well as reducing residues in the environment. environment. The first step for both symmetrical and non-symmetric 2-Oxoethylphthalate series was through (i) preparation of potassium terephthalate (2) from the depolymerization reaction of postconsumer PET bottles (1) in 90% of Yield. Non-symmetric 2-oxoethyl terephthalates (8a-j) were synthesized through six steps: (ii) acid hydrolysis reaction of recycled potassium terephthalate (2) in 100% yield; (iii) esterification reaction of terephthalic acid (3) with methanol in 80% yield; (iv) reaction of basic monohydrolysis of methyl terephthalate (4) in 77% yield; (v) acetylation reaction of aromatic amines with chloroacetyl chloride in 76-95% yield; and (vi) alkylating the methyl terephthalate salt (5) with 2-chloro-N-arylacetamides (6a-j) in 52-98% yield. Symmetric 2- oxoethylterephthalates (9a-d) were synthesized through three steps: (ii) esterification reaction of chloroacetic acid with different alkyl alcohols in 89-93% yield; and (iii) alkylation reaction of recycled potassium terephthalate (2) with alkylated 2- chloroacetates (7a-d) in 66-78% yield. Intermediate and final compounds were characterized by IR spectroscopic techniques, 1H and 13C NMR (uni and twodimensional) and mass spectrometry (CG-MS and ESI-MS). In the 80-0.31 µg.mL-1 concentration range, the final compounds (8a-j and 9a-d) showed no antifungal (yeast and filamentous fungi) and antibacterial activity in vitro. The compounds obtained in the crystalline form (8h and 9a-b) were submitted to single crystal X-ray diffraction analysis, through which, together with the supramolecular cluster methodology and quantum mechanics calculations of the density functional theory with dispersion correction. (DFT-D, Density Functional Theory-Dispersive), with calculation level wB97X-D / cc-pVDZ, it was possible to develop a topological and energetic study to analyze the similarities and differences in crystallization mechanisms through intermolecular interactions.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESEste trabalho descreve a síntese de dez compostos 2-oxoetiltereftalatos não simétricos e quatro simétricos, derivados do tereftalato de potássio, o qual foi obtido a partir da reação de despolimerização de garrafas de tereftalato de polietileno (PET) pós-consumo. A escolha por garrafas PET pós-consumo como matéria-prima advém da possibilidade de agregar valor a novas substâncias obtidas a partir de fontes recicláveis, e que, a somar, são candidatas a agentes antibacterianos e antifúngicos, além de permitir a redução de resíduos no meio ambiente. A primeira etapa para ambas as séries de 2-Oxoetiltereftalatos simétricos e não simétricos deu-se através da (i) preparação do tereftalato de potássio (2) a partir da reação de despolimerização de garrafas PET pós-consumo (1) em 90% de rendimento. 2-Oxoetiltereftalatos (8a-j) não simétricos foram sintetizados através de seis etapas: (ii) reação de hidrólise ácida do tereftalato de potássio reciclado (2) em 100% de rendimento; (iii) reação de esterificação do ácido tereftálico (3) com metanol em 80% de rendimento; (iv) reação de monohidrólise básica do tereftalato de metila (4) em 77% de rendimento; (v) reação de acetilação de aminas aromáticas com cloreto de cloroacetila em 76-95% de rendimento; e (vi) reação de alquilação do sal do tereftalato de metila (5) com 2-cloroN-arilacetamidas (6a-j) em 52-98% de rendimento. 2-Oxoetiltereftalatos simétricos (9a-d) foram sintetizados através de três etapas: (ii) reação de esterificação do ácido cloroacético com diferentes álcoois alquílicos em 89-93% de rendimento; e (iii) reação de alquilação do tereftalato de potássio reciclado (2) com 2-cloroacetatos alquilados (7a-d) em 66-78% de rendimento. Os compostos intermediários e finais foram caracterizados por técnicas espectroscópicas de IV, RMN de 1H e 13C (uni e bidimensionais) e espectrometria de massas (CG-MS e ESI-MS). Na faixa de concentração de 80-0,31 µg.mL-1, os compostos finais (8a-j e 9a-d) não apresentaram atividade antifúngica (leveduras e fungos filamentosos) e antibacteriana in vitro. Os compostos obtidos na forma cristalina (8h e 9a-b) foram submetidos à análise por difração de raios X em monocristal, através da qual, aliada à metodologia do cluster supramolecular e cálculos de mecânica quântica da teoria do funcional de densidade com correção de dispersão empírica (DFT-D, Density Functional Theory-Dispersive), com nível de cálculo wB97X-D/cc-pVDZ, foi possível desenvolver um estudo topológico e energético para analisar as semelhanças e diferenças nos mecanismos de cristalização através das interações intermoleculares.Universidade Federal da ParaíbaBrasilQuímicaPrograma de Pós-Graduação em QuímicaUFPBAthayde Filho, Petrônio Filgueiras dehttp://lattes.cnpq.br/1717412318563908Fiss, Gabriela Fehnhttp://lattes.cnpq.br/8012904041393217Lima, Priscila Santos Vieira de2021-01-01T21:17:00Z2019-10-112021-01-01T21:17:00Z2019-09-17info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesishttps://repositorio.ufpb.br/jspui/handle/123456789/19020porhttp://creativecommons.org/licenses/by-nd/3.0/br/info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFPBinstname:Universidade Federal da Paraíba (UFPB)instacron:UFPB2021-08-24T13:52:22Zoai:repositorio.ufpb.br:123456789/19020Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2021-08-24T13:52:22Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
title |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
spellingShingle |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo Lima, Priscila Santos Vieira de Reciclagem PET Acetamida 2-oxoetiltereftalato Avaliação antimicrobiana Estudo topológico e energético Recycling Acetamide 2-oxoethylterephthalate Antimicrobial evaluation Topological and energetic study CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
title_full |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
title_fullStr |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
title_full_unstemmed |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
title_sort |
Síntese, avaliação antimicrobiana e estudo topológico e energético de 2-oxoetiltereftalatos simétricos e não simétricos a partir de garrafas PET pós-consumo |
author |
Lima, Priscila Santos Vieira de |
author_facet |
Lima, Priscila Santos Vieira de |
author_role |
author |
dc.contributor.none.fl_str_mv |
Athayde Filho, Petrônio Filgueiras de http://lattes.cnpq.br/1717412318563908 Fiss, Gabriela Fehn http://lattes.cnpq.br/8012904041393217 |
dc.contributor.author.fl_str_mv |
Lima, Priscila Santos Vieira de |
dc.subject.por.fl_str_mv |
Reciclagem PET Acetamida 2-oxoetiltereftalato Avaliação antimicrobiana Estudo topológico e energético Recycling Acetamide 2-oxoethylterephthalate Antimicrobial evaluation Topological and energetic study CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Reciclagem PET Acetamida 2-oxoetiltereftalato Avaliação antimicrobiana Estudo topológico e energético Recycling Acetamide 2-oxoethylterephthalate Antimicrobial evaluation Topological and energetic study CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis of ten non-symmetric and four symmetric 2- oxoethylphthalate compounds, derived from potassium terephthalate, which was obtained from the depolymerization reaction of post-consumption polyethylene terephthalate (PET) bottles. The choice of post-consumer PET bottles as raw material comes from the possibility of adding value to new substances obtained from recyclable sources, which, in addition, are candidates for antibacterial and antifungal agents, as well as reducing residues in the environment. environment. The first step for both symmetrical and non-symmetric 2-Oxoethylphthalate series was through (i) preparation of potassium terephthalate (2) from the depolymerization reaction of postconsumer PET bottles (1) in 90% of Yield. Non-symmetric 2-oxoethyl terephthalates (8a-j) were synthesized through six steps: (ii) acid hydrolysis reaction of recycled potassium terephthalate (2) in 100% yield; (iii) esterification reaction of terephthalic acid (3) with methanol in 80% yield; (iv) reaction of basic monohydrolysis of methyl terephthalate (4) in 77% yield; (v) acetylation reaction of aromatic amines with chloroacetyl chloride in 76-95% yield; and (vi) alkylating the methyl terephthalate salt (5) with 2-chloro-N-arylacetamides (6a-j) in 52-98% yield. Symmetric 2- oxoethylterephthalates (9a-d) were synthesized through three steps: (ii) esterification reaction of chloroacetic acid with different alkyl alcohols in 89-93% yield; and (iii) alkylation reaction of recycled potassium terephthalate (2) with alkylated 2- chloroacetates (7a-d) in 66-78% yield. Intermediate and final compounds were characterized by IR spectroscopic techniques, 1H and 13C NMR (uni and twodimensional) and mass spectrometry (CG-MS and ESI-MS). In the 80-0.31 µg.mL-1 concentration range, the final compounds (8a-j and 9a-d) showed no antifungal (yeast and filamentous fungi) and antibacterial activity in vitro. The compounds obtained in the crystalline form (8h and 9a-b) were submitted to single crystal X-ray diffraction analysis, through which, together with the supramolecular cluster methodology and quantum mechanics calculations of the density functional theory with dispersion correction. (DFT-D, Density Functional Theory-Dispersive), with calculation level wB97X-D / cc-pVDZ, it was possible to develop a topological and energetic study to analyze the similarities and differences in crystallization mechanisms through intermolecular interactions. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10-11 2019-09-17 2021-01-01T21:17:00Z 2021-01-01T21:17:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufpb.br/jspui/handle/123456789/19020 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/19020 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Química Programa de Pós-Graduação em Química UFPB |
publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Química Programa de Pós-Graduação em Química UFPB |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFPB instname:Universidade Federal da Paraíba (UFPB) instacron:UFPB |
instname_str |
Universidade Federal da Paraíba (UFPB) |
instacron_str |
UFPB |
institution |
UFPB |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
collection |
Biblioteca Digital de Teses e Dissertações da UFPB |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB) |
repository.mail.fl_str_mv |
diretoria@ufpb.br|| diretoria@ufpb.br |
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1801843024644276224 |