20.500.12556/DKUM-54547 POLIPIRIDIN KOT TRDNI NOSILEC ZA BROMIRANJE STIRENA POLYPYRIDINE AS A SOLID REAGENT FOR STYRENE BROMINATION Diplomsko delo prikazuje študijo narave polipiridinskega trdnega nosilca za bromiranje stirena. Ker je oksidativno halogeniranje ena izmed najbolj perspektivnih metod za halogeniranje organskih spojin, smo najprej proučili selektivnost oksidativnega bromiranja stirena s HBr/H2O2 v organskih topilih, kot so diklorometan, metanol, acetonitril z in brez dodatka vode. Izkazalo se je, da je selektivnost reakcije odvisna od vrste topila, saj je v diklorometanu nastal le en produkt, (1,2-dibromoetil)benzen, npr. v metanolu pa so nastali kar trije produkti, poleg (1,2-dibromoetil)benzena še (2-bromo-1-metoksietil)benzen in 2-bromo-1-feniletanol. Nato smo raziskali naravo bromirnega reagenta v reakciji oksidativnega bromiranja tako, da smo primerjali selektivnost bromiranja stirena z različnimi bromirnimi reagenti na polimernem nosilcu, katere smo pripravili iz Br2, HBr3, in HOBr. Opazovali smo obnašanje reakcije v različnih organskih topilih z in brez dodatka vode, določili izkoristke in selektivnost reakcij s pomočjo 1H NMR in FTIR spektroskopije. Ugotovili smo, da obstaja veliko pozitivnih lastnosti uporabe trdnih nosilcev za izvedbo kemijskih reakcij. Sem spadajo enostavnost rokovanja z njimi, saj lahko preprosto zatehtamo željeno količino za reakcijo. Trdni nosilec lahko po končani reakciji enostavno odstranimo iz reakcijske zmesi s filtriranjem, kar pomeni, da lahko reagente na trdnih nosilcih večkrat uporabimo za reakcijo. Reagenti, kot npr. Br2 na trdnih nosilcih so tudi varnejši za uporabo. Brom je namreč toksična, jedka in lahko hapljiva tekočina, ki lahko povzroči nemalo težav. The thesis shows the study on polypyridine brominating reagents for bromination of styrene. Because oxidative halogenation is the most perspective method for organic compound halogenation, we first examined the selictivity of oxidative bromination of styrene with HBr/H2O2 in organic solvents, such as dichloromethane, methanol, acetonitrile with and withouth addition of water. It turned out that the selectivity of the reaction depends on the type of solvent used, because when we used dichloromethane as a solvent we only isolated (1,2-dibromoethyl)benzene, while when using methanol we obtained (1,2-dibromoethyl)benzene, 2-bromo-1-phenyletanon and 2-bromo-1-phenylethanol. In order to study the nature of brominating reagent in oxidative halogenation, we compared the selectivity of bromination of styrene with different polymeric bromination reagents prepared from polypyridine and Br2, HBr3 and HOBr. With them we studied reaction in different organic solvents with and withouth watter, determined the yield of the reaction, with 1H NMR and FTIR we researched the selectivity of the reaction and determined the weight fraction of comounds in the product. We have recognized that there are a lot of positive properties using polymeric reagents for chemical reactions, i.e. the ease of handling with them, because we can easily weigh the desired amount for the reaction. Solid carrier can be easily removed when the reaction is finished through the filtration proces, which means, that we can reuse polymeric reagents over and over again. Reagents as Br2 on polymeric carriers are also safer to use. Bromine is considered a toxic, corrosive and easy volatile substance which could cause a lot of problems. Trdni nosilci polimerni reagenti poli(4-vinil)piridin bromiranje oksidativno bromiranje Solid carrier polymer reagent poly(4-vinylpyridine) bromination oxidative halogenation true true false [S. Skrbinšek] Slovenski jezik Angleški jezik Diplomsko delo/naloga 2015-09-04 10:48:51 2015-10-21 09:51:21 2022-06-06 03:05:44 2021-05-12 03:11:10 2015 0 Maribor 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 66.094.414:547.821(043.2) 19438102 URN:SI:UM:DK:M6NUKKSS UN_Skrbinsek_Sandi_2015.pdf UN_Skrbinsek_Sandi_2015.pdf 1 896ECBA9190CCC1172B5D42472A28E81 a78831b02798ebd714e5bbc1dff2886ef8d51a77a75425c518d9c756c774e682 b4ccde3f-7c07-11eb-bb7a-00155d0001ca https://dk.um.si/Dokument.php?lang=slv&id=81772 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0