20.500.12556/RUL-111449 Nitriranje fenolov Nitriranje fenolov je postopek pri katerem poteče aromatska elektrofilna substitucija. Izvajamo jo lahko pri različnih pogojih, ki pa so odvisni od lastnosti substrata. Nitrofenoli so zelo pomembni v industrijskih panogah, saj imajo zelo raznoliko uporabnost glede na funkcionalne skupine, ki so še prisotne na obroču. Nekateri nitrofenoli so tudi strupeni, zato moramo paziti na varnost pri uporabi. Za nitriranje izbranih fenolov sem uporabila različne reagente glede na substrat. Pri fenolih z etilno skupino sem uporabila NaNO2, moker SiO2, za topilo pa MeOH in O2 za prepihovanje. Pri substratih s prisotno metoksi skupino sem uporabila ostrejšo metodo nitriranja (NaNO2, koncentrirano H2SO4 in H2O kot topilo). Pri fenolnih derivatih s karboksilno skupino pa sem uporabila KNO3 kot nitrirno sredstvo, v kombinaciji z AcOH, ki je služil kot topilo. Vse reakcije sem spremljala s tankoplastno kromatografijo in surove produkte očistila z radialno kromatografijo. Čiste produkte sem ustrezno okarakterizirala s spektroskopskimi in spektrometričnimi metodami (NMR, IR, HRMS, Ttal). Nitration of phenols is an aromatic electrofilic substituition. It can be done under different conditions, which depend on the characteristic of the substrates. Nitrophenols are very important in industry, as they can be used in variety of different branches. Their application depends on functional groups on the benzene ring. Some of nitrophenols can be very toxic, which is why we need to be extra careful with their usage. I performed the nitration reaction of selected phenols by using different reagents depending on the substrates. Substrates containing ethyl group, NaNO2, wet SiO2, MeOH as the solvent and with a flow of O2 was sufficient. For the substrates bearing a methoxy group, harsher reaction conditions were applied (NaNO2, concentrated H2SO4 and H2O as a solvent). Phenol derivatives with a carboxylic group were successfully nitrated using KNO3 in AcOH. All reactions were analyzed using thin-layer chromatography (TLC) and the crude products were purified using radial chromatography. All the purified products were characterized by spectroscopic and spectrometric methods (NMR, IR, HRMS, Ttal). Nitriranje fenol nitrofenol aromatske spojine Nitration phenol nitrophenol aromatic compounds true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2019-10-01 13:20:09 2019-10-01 13:20:12 2022-08-23 03:43:08 0000-00-00 00:00:00 2019 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 690 1538456003 Sklander_Ana_-_Nitriranje_fenolov.pdf Sklander_Ana_-_Nitriranje_fenolov.pdf 1 6D3AA3D432DB7D7535DAAFE66005F986 6cd0fd14be08fc8f7bdc32e05efc806866c44a85c6ed7af34fb45c34081dd66c 64094009-a1b7-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=123307 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0