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Previous issue date: 2017-08-16 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES / In this work, seven enaminoesters were synthesized, divided into three series depending on the starting amine, the series A is derived from phenethylamine, the series B of aniline and, finally, the series C derived from benzylamine. The synthesis occurred in two ways, the first being through the reaction of the ethyl acetoacetate in the presence of the corresponding amine in ethanol as solvent in the presence of p-toluenesulfonic acid and the second the amine in the presence of triethylamine and methanol as solvent, both in magnetic stirring at room temperature. The compounds were obtained as oil, with a high purity, and for some compounds separation via flash chromatography in ethyl acetate / hexane was required, yields ranging from 70-93%. The compounds were characterized by spectroscopic techniques such as Infrared and Nuclear Magnetic Resonance 1H and 13C, in addition to the refractive index. Six of the seven compounds synthesized were evaluated using electrochemical techniques of Impedance Spectroscopy Electrochemistry, Potentiodynamic Polarization and Resistance to Linear Polarization and the mass loss technique, as to the action as inhibitors of corrosion against AISI 1020 carbon steel in 0.5 mol L-1 HCl. The Molecular Modeling technique was used to better visualize the structures of the synthesized enaminoesters and, later, correlation of the inhibition efficiencies found. The theoretical parameters such as the energy of the orbitals of symmetrical boundaries and dipole moment with the results corrosion efficiency were also evaluated. In general, the enaminoesters showed good corrosion efficiency, excess by the compound derived from hydroxylaniline. All presented corrosion inhibition efficiency with mixed inhibitor characteristics. However, the compounds that did not present substituents and those that contain electron donor group (OCH3) stood out as inhibitors, highlighting the compound EN1, which presented efficiency of 92% of inhibition of the corrosion by the technique of Resistance to Polarization Potentiodynamics and 98% by the technique of mass loss after 24h of immersion. The efficiency was shown to be dependent on the concentration in the synthesized compounds, that is, the corrosion inhibition efficiency increases with
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increasing inhibitor concentration, and that the adsorption phenomena of the compounds studied obey the Langmuir isotherm. Thus, the synthesized, especially the not substituted, enaminoesters can be considered as promising corrosion inhibiting agents for acidic AISI 1020 carbon steel. / Nesta disserta??o, foram sintetizados sete enamino?steres, divididos em tr?s s?ries de acordo com a amina de partida, sendo a s?rie A derivada da fenetilamina, a s?rie B da anilina e, por ?ltimo, a s?rie C derivada da benzilamina. A s?ntese ocorreu de duas formas, sendo a primeira atrav?s da rea??o do acetoacetato de etila na presen?a da amina correspondente em etanol como solvente, na presen?a de ?cido p-toluenossulf?nico e, a segunda, a amina na presen?a de trietilamina e metanol como solvente, ambas em agita??o magn?tica ? temperatura ambiente. Os compostos foram obtidos em forma de ?leo, com alto grau de pureza, sendo necess?ria para alguns compostos a separa??o via cromatografia flash em acetato de etila/hexano, os rendimentos variaram na faixa de 70-93%. Os compostos foram caracterizados por t?cnicas espectrosc?picas de Infravermelho e Resson?ncia Magn?tica Nuclear 1H e 13C, al?m de ?ndice de refra??o.
Seis dos sete compostos sintetizados foram avaliados por t?cnicas eletroqu?micas de Espectroscopia de Imped?ncia Eletroqu?mica, Polariza??o Potenciodin?mica e Resist?ncia a Polariza??o Linear e, por ensaio de perda de massa, quanto ? a??o como inibidores de corros?o frente a a?o carbono AISI 1020 em solu??o de HCl 0,5 mol L-1 .
Modelagem Molecular foi utilizada para melhor visualiza??o das estruturas moleculares dos enamino?steres sintetizados e, posterior, correla??o das efici?ncias de inibi??o encontradas. Os par?metros te?ricos como a energia dos orbitais de fronteiras sim?tricos e momento dipolar foram calculados e, apenas os valores de momento dipolar correlacionaram com os resultados experimentais da efici?ncia anticorrosiva.
De forma geral, os enamino?steres apresentaram boa efici?ncia anticorrosiva, com exce??o do composto derivado da hidr?xianilina (EN6). Todos apresentaram efici?ncia de inibi??o ? corros?o com caracter?sticas de inibidores mistos. Por?m, os compostos que n?o apresentaram substituintes e os que cont?m grupo doador de el?trons (OCH3) se destacaram como inibidores mais eficientes, dando destaque ao composto EN1, que apresentou efici?ncia de 92% de inibi??o da corros?o, pela t?cnica de Resist?ncia a Polariza??o Potenciodin?mica e 98% pela t?cnica de perda de massa ap?s 24 h de imers?o.
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A efici?ncia se mostrou dependente da concentra??o nos compostos sintetizados, ou seja, a efici?ncia de inibi??o da corros?o aumentou com o aumento da concentra??o dos inibidores. Os fen?menos de adsor??o dos compostos estudados, apenas o EN1 obedece ? isoterma de Langmuir e os restantes a Langmuir modificada.
Com isso, os enamino?steres sintetizados, especialmente os n?o substitu?dos, podem ser considerados como promissores agentes inibidores da corros?o para o a?o carbono AISI 1020 em meio ?cido.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/2255 |
| Date | 16 August 2017 |
| Creators | Carlos, Mariana Falc?o Lopes Princisval |
| Contributors | Lima, Aurea Echevarria Aznar Neves, Santos, Margareth Rose Lima, Rezende, Michelle Jakeline Cunha, Rocha J?nior, Jos? Geraldo |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
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