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Title:Razvoj sintezne metode za pripravo biarilov z Ullmannovo reakcijo : diplomsko delo univerzitetnega študijskega programa I. stopnje
Authors:ID Škrinjarič, Žiga (Author)
ID Paljevac, Muzafera (Mentor) More about this mentor... New window
ID Krajnc, Peter (Comentor)
Files:.pdf UN_Skrinjaric_Ziga_2023.pdf (2,28 MB)
MD5: E9B23B960C625768DCA2EDA6533C083C
 
Language:Slovenian
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Engineering
Abstract:V diplomskem delu je predstavljena sinteza in karakterizacija biarila N-benzilanilina, ki smo ga sintetizirali z Ullmannovo reakcijo po mehanizmu križnega spajanja (angl. cross coupling). Z namenom pridobitve čistega produkta s čim višjimi izkoristki smo reakcije sinteze izvedli z optimiziranjem treh reakcijskih pogojev, in sicer temperature, časa reakcije in atmosfere, v kateri je reakcija potekala. Končne produkte Ullmannove reakcije smo okarakterizirali z infrardečo in jedrsko magnetno spektroskopijo. Z infrardečo spektroskopijo smo potrdili nastanek biarila N-benzilanilina pri vseh testnih reakcijah, v nekaterih primerih tudi prisotnost benzilamina oz. jodobenzena. Z jedrsko magnetno resonanco smo potrdili njihovo kemijsko strukturo in določili njihovo razmerje v vzorcu. Ugotovili smo, da višje izkoristke N-benzilanilina dosegamo z reakcijami, ki jih izvedemo v dušikovi atmosferi pri 80°C in trajajo dlje časa, pri reakcijah na zraku pa N-benzilanilin oksidira do N- benzilidenanilina, ki se pojavlja v produktu v višjih koncentracijah.
Keywords:Ullmannova reakcija, križno spajanje, biarili, N-benzilanilin, FTIR, NMR
Place of publishing:Maribor
Place of performance:Maribor
Publisher:[Ž. Škrinjarič]
Year of publishing:2023
Number of pages:1 spletni vir (1 datoteka PDF (VIII, 33 f.))
PID:20.500.12556/DKUM-85578 New window
UDC:66.095.257(043.2)
COBISS.SI-ID:167172867 New window
Publication date in DKUM:11.09.2023
Views:718
Downloads:91
Metadata:XML DC-XML DC-RDF
Categories:KTFMB - FKKT
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Licences

License:CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
Link:http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.
Licensing start date:01.09.2023

Secondary language

Language:English
Title:Development of a synthesis method for the preparation of biaryls using the Ullmann reaction
Abstract:This work presents the synthesis and characterization of biaryl N-benzylaniline synthesized by the Ullmann reaction using the cross-coupling mechanism. In order to obtain a pure product with the highest possible yield, the synthesis reactions were carried out by optimizing three reaction conditions, namely temperature, reaction time and the atmosphere in which the reaction took place. The final products of the Ullmann reaction were characterized by infrared and nuclear magnetic spectroscopy. Infrared spectroscopy confirmed the formation of biaryl N-benzylaniline in all test reactions, and in some cases the presence of benzylamine or iodobenzene. Using nuclear magnetic resonance, we confirmed their chemical structure and determined their ratio in the sample. We found that higher yields of N-benzylaniline are obtained with reactions carried out in a nitrogen atmosphere at 80°C and lasting longer, while reactions in air oxidize N-benzylaniline to N-benzylideneaniline, which appears in the product in higher concentration.
Keywords:Ullmann reaction, cross coupling, biaryls, N-benzylaniline, FTIR, NMR


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