magistrsko delo študijskega programa II. stopnje
Dolores Zimerl (Author), Jernej Iskra (Mentor), Peter Krajnc (Co-mentor)

Abstract

Fluorirani alkoholi so s sinteznega stališča zelo zanimivi, saj lahko v določenih reakcijah zaradi svojih fizikalno-kemijskih lastnosti nadomestijo kovinske katalizatorje. S tem se olajša tudi čiščenje produktov, kar je še posebej pomembno pri farmacevtskih učinkovinah, kjer so zahteve po čistosti zelo stroge. V sklopu magistrske naloge smo raziskali možnost priprave fluoriranih alkoholov v polimerni obliki. Monomer bi moral tako vsebovati v svoji strukturi fluoriran alkohol in dvojno vez, preko katere bi izvedli polimerizacijo. Z retrosintezno analizo smo kot izhodni spojini izbrali bromoalken ter fluoriran keton, ki z Grignardovo reakcijo v eni stopnji zreagirata v želeni fluoriran monomer. Sinteze smo zaradi manjše hlapnosti in posledično lažje eksperimentalne izvedbe začeli na acetofenonu. Ko smo preiskali pogoje in situ tvorbe alilmagnezijevega bromida in 4-bromobut-1-enmagnezijevega bromida, smo sinteze nadaljevali na acetonu, kasneje pa še na 1,1,1,3,3,3-heksafluoropropan-2-onu, 2,2,2-trifluoro-1-feniletanonu in 2,2,2-trifluoroacetaldehidu. Pri izolaciji hlapnih alkoholov smo naleteli na težave, ki jih v danem časovnem okviru nismo popolnoma odpravili. Sintetizirane analoge alkoholov smo v naslednji stopnji kopolimerizirali s stirenom ali metil metakrilatom, za iniciacijo pa smo uporabili AIBN in DBP. Izkazalo se je, da kopolimerizacija ni potekla v želeni smeri, saj smo namesto želenega kopolimera dobili polimer z večinskim deležem polistirena, večina fluoriranega alkohola pa je ostala v monomerni obliki. V zadnjem delu smo dobljene polimere in fluorirane alkohole testirali na reakciji dihidroperoksidaciji ketonov z vodikovim peroksidom.

Keywords

fluorirani alkoholi;polimerizacija;reakcije na trdnem nosilcu;vodikov peroksid;zelena kemija;magistrske naloge;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UM FKKT - Faculty of Chemistry and Chemical Engineering
Publisher: [D. Zimerl]
UDC: 66.094.412:678-13(043.2)
COBISS: 20694294 Link will open in a new window
Views: 1155
Downloads: 99
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Other data

Secondary language: English
Secondary title: Preparation of fluorinated alcohol analogue in polymer form
Secondary abstract: Fluorinated alcohols play an important role in organic synthesis. Because of their unique properties they can replace metal catalysts in some reactions. Application of fluorinated alcohols as solvent or cosolvent can result in cleaner products, which is especially important in pharmaceutical industry, where the demands for clean products are very high. In this work we aimed to prepare fluorinated alcohols in polymer form. Desired monomer should comprise of fluorinated alcohol and double bond, which would be later polymerised. Trough retrosynthetic analysis we defined to use fluorinated ketone and bromoalkene as substrates. Because of lower volatility and easier experimental work, we used acetophenone as a model substrate. After the determination of optimal conditions for in situ generation of allylmagnesium bromide and 4-bromo-1-enemagnesium bromide we continued reactions on acetone, 1,1,1,3,3,3-hexafluoropropan-2-one, 2,2,2-trifluoro-1-phenyletanone and 2,2,2-trufluoroacetaldehyde. Due to high volatility of desired products we encountered a lot of difficulties with isolation, which we were only able to resolve partially. In the next section of experimental work, we used AIBN and DBP to initiate copolymerisation of previously prepared monomers with styrene and methyl methacrylate. The copolymer proved out to be mainly polystyrene, whilst fluorinated alcohol remained mainly in monomer form. In the end we tested catalytical activity of selected polymers and alcohols on reaction of dihyrdoperoxidation od ketone by hydrogen peroxide.
Secondary keywords: solid reactions;green chemistry;hydrogen peroxide;fluorinated alcohols;polymerisation;
URN: URN:SI:UM:
Type (COBISS): Master's thesis/paper
Thesis comment: Univ. v Mariboru, Fak. za kemijo in kemijsko tehnologijo
Pages: IX, 71 str.
ID: 9608989