S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas
| Ano de defesa: | 2013 |
|---|---|
| Autor(a) principal: |
Santos, Cristiane Frauches dos
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| Orientador(a): |
Lima, Aurea Echevarria Aznar Neves
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| Banca de defesa: | , |
| Tipo de documento: | Dissertação |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Universidade Federal Rural do Rio de Janeiro
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| Programa de Pós-Graduação: |
Programa de P?s-Gradua??o em Qu?mica
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| Departamento: |
Instituto de Ci?ncias Exatas
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| País: |
Brasil
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| Palavras-chave em Português: | |
| Palavras-chave em Inglês: | |
| Área do conhecimento CNPq: | |
| Link de acesso: | https://tede.ufrrj.br/jspui/handle/jspui/3446 |
Resumo: | In this work, 16 compounds wer synthesized aiming their applications as corrosion inhibitors, in while eleven corresponds to 1,3,4-thiadiazolie-2-phenilamine hydrochlorides and the other five compounds were from the 1,3,4-thiadiazolium-2-phenilaminide mesoionic class (free base), where 15 are new compounds. All the compounds were obtained with satisfactory purity and in good yields, varying from 51 to 98% (mesoionic hydrochlorides), and 71 to 96% (free bases). They were also characterised by infrared, and most of them by 1H and/ or 13C NMR. The compounds were investigated by methods of Theoretical Chemistry using the program SPARTAN-PRO in the semi-empirical method with Hamiltonian AM1 to calculate their structural and electronic properties with contribution to the efficiency of inhibition corrosion. Five of the mesoionic hydrochloride were tested against AISI 1020 carbon steel corrosion in HCl 1,0 mol.L-1 solution, dissolved in different solvents, DMSO:water and methanol:water. Potentiodynamic polarization electrochemical techniques and electrochemical impedance spectroscopy were used to evaluate them. Results showed significant percentage of corrosion inhibition, reaching the 88% efficiency index, at the highest concentration for 4-phenyl-5-(3?-chlorophenyl)-1,3,4-thiadiazolium-2-phenylamine when dissolved in DMSO:water (7:3), and 86% for 4-phenyl-5-(3?-fluoro-phenyl)-1,3,4-thiadiazolium-2-phenylamine dissolved in methanol:water (7:3). Methodologies used for evaluating the anticorrosive activity (potentiodynamic polarization and impedance spectroscopy), including the theoretical molecular modeling evaluation, indicated that mesoionic hydrochlorides are corrosion inhibitors. After all, the experimental results confirmed the theoretical ones. |
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Lima, Aurea Echevarria Aznar Neves668.742.388-68http://lattes.cnpq.br/1879077396134052Maciel, Maria Aparecida MedeirosOliveira, M?rcia Cristina Campos de102.456.867-97http://lattes.cnpq.br/5553250784447603Santos, Cristiane Frauches dos2020-04-21T15:20:22Z2013-07-22SANTOS, Cristiane Frauches dos. S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas. 2013. 168 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013.https://tede.ufrrj.br/jspui/handle/jspui/3446In this work, 16 compounds wer synthesized aiming their applications as corrosion inhibitors, in while eleven corresponds to 1,3,4-thiadiazolie-2-phenilamine hydrochlorides and the other five compounds were from the 1,3,4-thiadiazolium-2-phenilaminide mesoionic class (free base), where 15 are new compounds. All the compounds were obtained with satisfactory purity and in good yields, varying from 51 to 98% (mesoionic hydrochlorides), and 71 to 96% (free bases). They were also characterised by infrared, and most of them by 1H and/ or 13C NMR. The compounds were investigated by methods of Theoretical Chemistry using the program SPARTAN-PRO in the semi-empirical method with Hamiltonian AM1 to calculate their structural and electronic properties with contribution to the efficiency of inhibition corrosion. Five of the mesoionic hydrochloride were tested against AISI 1020 carbon steel corrosion in HCl 1,0 mol.L-1 solution, dissolved in different solvents, DMSO:water and methanol:water. Potentiodynamic polarization electrochemical techniques and electrochemical impedance spectroscopy were used to evaluate them. Results showed significant percentage of corrosion inhibition, reaching the 88% efficiency index, at the highest concentration for 4-phenyl-5-(3?-chlorophenyl)-1,3,4-thiadiazolium-2-phenylamine when dissolved in DMSO:water (7:3), and 86% for 4-phenyl-5-(3?-fluoro-phenyl)-1,3,4-thiadiazolium-2-phenylamine dissolved in methanol:water (7:3). Methodologies used for evaluating the anticorrosive activity (potentiodynamic polarization and impedance spectroscopy), including the theoretical molecular modeling evaluation, indicated that mesoionic hydrochlorides are corrosion inhibitors. After all, the experimental results confirmed the theoretical ones.Nesta Disserta??o foram sintetizados 16 compostos do tipo mesoi?nico, sendo 11 cloridratos dos mesoi?nicos 1,3,4-tiadiaz?lio-2-fenilaminas e os outros 5 compostos dos mesoi?nicos pertencentes ? classe dos mesoi?nicos 1,3,4-tiadiazolio-2-fenilaminidas (bases livres), sendo 15 in?ditos, com o objetivo de avaliar a efici?ncia dos mesmos como inibidores de corros?o. Todos os compostos foram obtidos com grau de pureza satisfat?rio e com bons rendimentos, variando entre 51 e 98% (cloridratos mesoi?nicos) e 71 e 96% (bases livres). Todos os compostos foram caracterizados por infravermelho e, a maioria foi caracterizada, tamb?m, por RMN de 1H e/ou 13C. Os compostos foram investigados por m?todos da Qu?mica Te?rica, utilizando o programa SPARTAN-PRO no m?todo semi-emp?rico com o hamiltoniano AM1, para determina??o de suas propriedades estruturais e eletr?nicas que pudessem contribuir para a efici?ncia de inibi??o da corros?o. Cinco cloridratos mesoi?nicos foram testados frente ? corros?o de a?o carbono AISI 1020 em solu??o de HCl 1,0 mol. L-1, dissolvidos em diferentes solventes, DMSO:?gua e metanol:?gua. Para tal avalia??o foram utilizadas as t?cnicas eletroqu?micas de polariza??o potenciodin?mica e espectroscopia de imped?ncia eletroqu?mica. Os resultados mostraram percentuais significativos de inibi??o da corros?o, alcan?ando o ?ndice de 88 % de efici?ncia na maior concentra??o, obtida para o composto 4-fenil-5-(3?-cloro-fenil)-1,3,4-tiadiaz?lio-2-fenilamina quando dissolvido em DMSO:?gua (7:3), e 86% de efici?ncia na maior concentra??o, obtida para o composto 4-fenil-5-(3?-fl?or-fenil)-1,3,4-tiadiaz?lio-2-fenilamina dissolvido em metanol:?gua (7:3). As metodologias utilizadas para avalia??o da atividade anticorrosiva (polariza??o Potenciodin?mica e Espectroscopia de Imped?ncia), incluindo a avalia??o te?rica por modelagem molecular, indicaram os cloridratos mesoi?nicos como inibidores de corros?o. Os resultados experimentais, em todos os casos, confirmaram os resultados te?ricos previamente obtidos.Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2020-04-21T15:20:22Z No. of bitstreams: 1 2013 - Cristiane Frauches dos Santos.pdf: 3048758 bytes, checksum: 6733341b8f28634c0268fddda199e5ea (MD5)Made available in DSpace on 2020-04-21T15:20:22Z (GMT). No. of bitstreams: 1 2013 - Cristiane Frauches dos Santos.pdf: 3048758 bytes, checksum: 6733341b8f28634c0268fddda199e5ea (MD5) Previous issue date: 2013-07-22Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil.application/pdfhttps://tede.ufrrj.br/retrieve/14228/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/15856/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/22192/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/28532/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/35016/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/41362/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/47750/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpghttps://tede.ufrrj.br/retrieve/54240/2013%20-%20Cristiane%20Frauches%20dos%20Santos.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias ExatasABDUL NABI, A.S. & HUSSAIN, A.A.; Synthesis, Identification and study of some new azo dyes as corrosion inhibitors for carbon-steel in acidic media. 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SAFAK, S.; DURAN, B.; YURT, A.; TURKOGLU, G.; Schiff bases as corrosion inhibitor for aluminium in HCl solution, Corrosion Science, v. 54, 251?259, 2012. 120 SANT?ANNA, C.M.R.; gloss?rio de termos usados no planejamento de f?rmacos (Recomenda??es da IUPAC para 1997). Qu?mica Nova, v. 25, 505-512, 2002. SANTOS, A.O.; Estudos da resist?ncia ? corros?o em a?o e revestimentos visando aplica??o em hastes de bombeiro de petr?leo. Disserta??o de Mestrado em Engenharia de Processos ? Universidade Tiradentes, 2008. SANTOS, H.F.; O conceito da modelagem molecular. Cadernos Tem?ticos de Qu?mica Nova na Escola, Modelagem molecular, n? 4, 4-5, 2001. SANTOS, A.C.S.; S?ntese, espectroscopia e correla??es de energia livre de novos heterociclos mesoi?nicos da classe dos 1,3,4-tiadiaz?lio-2-fenilaminas, disserta??o de Mestrado, PPGQO, UFRRJ (1993). SCHUTTE, C.L.; Environmental durability of glass-fiber composites. Materials Science and Engineering R, v. 13, 265?323, 1994. SHERIF, E.M.; PARK, S.-M.; 2-Amino-5-ethyl-1,3,4-thiadiazole as a corrosion inhibitor for copper in 3.0% NaCl solutions. Corrosion Science, v. 48, 4065?4079, 2006. SHYLESHA, B.S.; VENKATESHA, T.V.; and PRAVEEN, B.M.; Corrosion inhibition studies of mild steel by new inhibitor in different corrosive medium. Research Journal of Chemical Sciences,v. 1, 46-50, 2011. SOUZA FILHO, J.E.; Material de aula ? Processamento prim?rio de fluidos: separa??o e tratamento. Universidade Petrobr?s, Salvador, 2002. SOUZA, F.S.; SPINELLI, A.; Caffeic acid as a green corrosion inhibitor for mild steel. Corrosion Science, v. 51, 642-649; 2009. V?RGES, G.R.; Estudo do desempenho de sistemas de pintura para materiais das redes de distribui??o de energia el?trica situadas em regi?es litor?neas. 2005. 194f. Disserta??o (Mestrado em Engenharia e Ci?ncia dos Materiais) - Setor de Tecnologia, Universidade Federal do Paran?, Curitiba, 2005. VRACAR, LJ. M.; DRAZIC, D.M.; Adsorption and corrosion inhibitive properties of some organic molecules on iron electrode in sulfuric acid. Corrosion Science, v. 44, 1669?1680, 2002. YOUNG, D.C.; Computational Chemistry: A Practical Guide for Applying Techniques to Real-Problems. New York, John Wiley e Sons, 2001. 121 YUCE, A.O., KARDAS, G.; Adsorption and inhibition effect of 2-thiohydantoin on mild steel corrosion in 0.1 M HCl. Corrosion Science, v. 58, 86?94, 2012. YURT, A.; ULUTAS, S.; DAL, H.; Electrochemical and theoretical investigation on the corrosion of aluminium in acidic solution containing some Schiff bases. Applied Surface Science, v. 253, 919-925, 2006. ZHANG, Q.B., HUA, Y.X.; Corrosion inhibition of mild steel by alkylimidazolium ionic liquids in hydrochloric acid. 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| dc.title.por.fl_str_mv |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| dc.title.alternative.eng.fl_str_mv |
Synthesis and experimental and theoretical evaluation of the anticorrosive activity of 4-phenyl-5- (X-phenyl) -1,3,4-thiadiazolium-2-phenylamines hydrochlorides |
| title |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| spellingShingle |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas Santos, Cristiane Frauches dos inibidores org?nicos de corros?o cloridratos mesoi?nicos atividade anticorrosiva Modelagem Molecular Polariza??o Potenciodin?mica Espectroscopia de Imped?ncia Organic corrosion inhibitors mesoionic /hydrochloride anticorrosive activity molecular modeling Potentiodynamic polarization impedance spectroscopy Qu?mica |
| title_short |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| title_full |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| title_fullStr |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| title_full_unstemmed |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| title_sort |
S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas |
| author |
Santos, Cristiane Frauches dos |
| author_facet |
Santos, Cristiane Frauches dos |
| author_role |
author |
| dc.contributor.advisor1.fl_str_mv |
Lima, Aurea Echevarria Aznar Neves |
| dc.contributor.advisor1ID.fl_str_mv |
668.742.388-68 |
| dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/1879077396134052 |
| dc.contributor.referee1.fl_str_mv |
Maciel, Maria Aparecida Medeiros |
| dc.contributor.referee2.fl_str_mv |
Oliveira, M?rcia Cristina Campos de |
| dc.contributor.authorID.fl_str_mv |
102.456.867-97 |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5553250784447603 |
| dc.contributor.author.fl_str_mv |
Santos, Cristiane Frauches dos |
| contributor_str_mv |
Lima, Aurea Echevarria Aznar Neves Maciel, Maria Aparecida Medeiros Oliveira, M?rcia Cristina Campos de |
| dc.subject.por.fl_str_mv |
inibidores org?nicos de corros?o cloridratos mesoi?nicos atividade anticorrosiva Modelagem Molecular Polariza??o Potenciodin?mica Espectroscopia de Imped?ncia |
| topic |
inibidores org?nicos de corros?o cloridratos mesoi?nicos atividade anticorrosiva Modelagem Molecular Polariza??o Potenciodin?mica Espectroscopia de Imped?ncia Organic corrosion inhibitors mesoionic /hydrochloride anticorrosive activity molecular modeling Potentiodynamic polarization impedance spectroscopy Qu?mica |
| dc.subject.eng.fl_str_mv |
Organic corrosion inhibitors mesoionic /hydrochloride anticorrosive activity molecular modeling Potentiodynamic polarization impedance spectroscopy |
| dc.subject.cnpq.fl_str_mv |
Qu?mica |
| description |
In this work, 16 compounds wer synthesized aiming their applications as corrosion inhibitors, in while eleven corresponds to 1,3,4-thiadiazolie-2-phenilamine hydrochlorides and the other five compounds were from the 1,3,4-thiadiazolium-2-phenilaminide mesoionic class (free base), where 15 are new compounds. All the compounds were obtained with satisfactory purity and in good yields, varying from 51 to 98% (mesoionic hydrochlorides), and 71 to 96% (free bases). They were also characterised by infrared, and most of them by 1H and/ or 13C NMR. The compounds were investigated by methods of Theoretical Chemistry using the program SPARTAN-PRO in the semi-empirical method with Hamiltonian AM1 to calculate their structural and electronic properties with contribution to the efficiency of inhibition corrosion. Five of the mesoionic hydrochloride were tested against AISI 1020 carbon steel corrosion in HCl 1,0 mol.L-1 solution, dissolved in different solvents, DMSO:water and methanol:water. Potentiodynamic polarization electrochemical techniques and electrochemical impedance spectroscopy were used to evaluate them. Results showed significant percentage of corrosion inhibition, reaching the 88% efficiency index, at the highest concentration for 4-phenyl-5-(3?-chlorophenyl)-1,3,4-thiadiazolium-2-phenylamine when dissolved in DMSO:water (7:3), and 86% for 4-phenyl-5-(3?-fluoro-phenyl)-1,3,4-thiadiazolium-2-phenylamine dissolved in methanol:water (7:3). Methodologies used for evaluating the anticorrosive activity (potentiodynamic polarization and impedance spectroscopy), including the theoretical molecular modeling evaluation, indicated that mesoionic hydrochlorides are corrosion inhibitors. After all, the experimental results confirmed the theoretical ones. |
| publishDate |
2013 |
| dc.date.issued.fl_str_mv |
2013-07-22 |
| dc.date.accessioned.fl_str_mv |
2020-04-21T15:20:22Z |
| 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.citation.fl_str_mv |
SANTOS, Cristiane Frauches dos. S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas. 2013. 168 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013. |
| dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/3446 |
| identifier_str_mv |
SANTOS, Cristiane Frauches dos. S?ntese e avalia??o experimental e te?rica da atividade anticorrosiva de cloridratos de 4-fenil-5-(X-fenil)-1,3,4-tiadiaz?lio-2-fenilaminas. 2013. 168 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013. |
| url |
https://tede.ufrrj.br/jspui/handle/jspui/3446 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.references.por.fl_str_mv |
ABDUL NABI, A.S. & HUSSAIN, A.A.; Synthesis, Identification and study of some new azo dyes as corrosion inhibitors for carbon-steel in acidic media. Journal of Basrah Researches (Sciences), v. 38, 125-146, 2012. ANTONIJEVIC, M.M PETROVIC, M.B.; Copper corrosion inhibitors. A review. International Journal of Electrochemical Science, v. 3, 1?28, 2008. ARAB, S.T.; Inibition action of thiosemicabazone and some of it is p-substituted compounds on the corrosion of iron-base metallic glass alloy in 0,5 M H2SO4 at 30 ?C. Materials Research Bulletin, v. 43, 510-521, 2008. ARROIO, A.; HON?RIO, K.M.; SILVA, A.B.F.; Propriedades qu?mico-qu?nticas empregadas em estudos das rela??es estrutura-atividade. Qu?mica Nova, v. 33, n. 3, p. 694-699, 2010. Dispon?vel em: <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010000300037&lng=en&nrm=iso>. Acesso em: 27 DEZ. 2012. BAYER, R.F.; Crit?rios para especifica??o de revestimentos anticorrosivos, ALCOOLbr?s ? Janeiro/Fevereiro 2001. 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