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Študija aerobne oksidacije dibenzotiofena in tiantrena z dušikovo kislino kot katalizatorjem v fluoriranih alkoholih
ID Corn, Matej (Author), ID Iskra, Jernej (Mentor) More about this mentor... This link opens in a new window

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Abstract
Sulfoksidi in sulfoni ustvarjajo množico spojin, ki kažejo biološko aktivne lastnosti. Zato med farmacevtskimi spojinami najdemo veliko takih, ki vsebujejo sulfoksidno ali sulfonsko skupino. Z rastjo števila različnih žveplovih spojin pa raste tudi povpraševanje po različnih sinteznih poteh, med novejšimi pa lahko najdemo vedno več tako imenovanih zelenih poti sinteze, ki vsebujejo reaktante, ki niso obremenjujoči za okolje. V diplomskem delu sem raziskal selektivnost aerobne oksidacije aromatskih sulfidov z uporabo dušikovo(V) kislino, železovimi ioni kot katalizatorjev v fluoriranih alkoholih. Spreminjal sem vrsto in količino topila, katalizatorjev in temperaturo. Uspel sem izolirati želeni sulfoksid dibenzotiofena, dibenzo[b,d]tiofen 5-oksid, z 72% izkoristkom. Oksidacijo sem naredil tudi s substratom tiantrenom, kjer sem sulfoksid tiantren 5-oksid izoliral z 41% izkoristkom, hkrati pa je potekla tudi nadaljnja oksidacija predvsem do cis-tiantren 5,10-dioksida s 5,5% izkoristkom in trans-tiantren 5,10-dioksida s 30% izkoristkom.

Language:Slovenian
Keywords:sulfoksid, aerobna oksidacija, kataliza, zelena kemija, dušikova(V) kislina
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
PID:20.500.12556/RUL-114498 This link opens in a new window
COBISS.SI-ID:1538541763 This link opens in a new window
Publication date in RUL:03.03.2020
Views:1501
Downloads:230
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Secondary language

Language:English
Title:Study of aerobic oxidation of dibenzothiophen and thianthren with nitric acid as catalyst in fluorinated alcohols
Abstract:
Sulfoxides and sulfones create a set of chemical compounds, that show biological activity. That is why we can find a lot of different pharmaceutical compounds that include either sulfoxide or sulfone group. As variety of different sulfur compounds grows everyday, there is also a growth in synthesis of such chemicals. We can find more and more different so called green routes of synthesis, which include reactants that present minimum burden to our living environment. In this undergraduate degree I studied selectivity of aerobic oxidation of aromatic sulfides with usage of nitric(V) acid and iron ions as catalysts in fluorinated alcohols. I varied solvents and their amounts, temperature and catalysts and its quantity. I succeded to obtain the wanted sulfoxide of dibenzotiophene, dibenzo[b,d]tiophene 5-oxide with a yield of 72%. Same oxidation method was also applied on thianthren which sulfoxides were isolated. Thianthren 5-oxide with a 41% yield and two thianthren dioxides cis-thianthren 5,10-dioxide with a 5,5% yield and trans-thianthren 5,10-dioxide with a 30% yield.

Keywords:sulfoxide, aerobic oxidation, catalysis, green chemistry, nitric(V) acid

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