Sinteza in hidrogeniranje substituiranega metil akrilata

Lišter, Monika (author), Štefane, Bogdan (mentor)

Hidrogeniranje akrilatnih estrov je pomemben sklop reakcij, s katerimi pridobivamo uporabne produkte na različnih področjih kemijske industrije. V dveh sinteznih stopnjah smo sintetizirali substituiran akrilatni ester (metil 2-benzamido-3-(2-bromofenil)akrilat), ki smo ga nadalje hidrogenirali z uporabo katalizatorjev na osnovi štirih različnih kovin (Pd, Ru, Ir in Rh). Pri uporabi 10 ut.% katalizatorja Pd/C, je poleg reakcije hidrogenacije poteklo tudi dehalogeniranje, kljub uporabi milih reakcijskih pogojev. Reakcijo smo uspešno katalizirali z 10 mol% [Ir(1,5-COD)Cl]2, [Ir(OMe)(1,5-COD)]2, RuCl2(PPh3)3 in RhCl(PPh3)3, kjer je bila konverzija popolna do končnega nasičenega estra. Nekoliko slabšo konverzijo smo dosegli z uporabo katalizatorjev [Ru(p-cimen)Cl2]2, IrCl3 x H2O in [Ir(1,5-COD)Cl]2 z dodatkom liganda MandyPhos.

• Language: Slovenian
• Keywords: hidrogeniranje, akrilatni ester, katalizator, ligand
• 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-120697
• COBISS.SI-ID: 34968579
• Publication date in RUL: 24.09.2020

Secondary language

• Language: English
• Title: Synthesis and hydrogenation of methyl acrylate

Abstract

Hydrogenation of acrylic esters is an important group of reactions with which we gather useful products in different branches of the chemical industry. We synthesized a substituted acrylic ester (methyl 2-benzamido-3-(2-bromophenyl)acrylate) in two stages and then hydrogenated it using four different metal-based catalysts (Pd, Ru, Ir and Rh). Besides the hydrogenation reaction, dehalogenation reaction also occurred with 10 wt% Pd/C, even under mild reaction conditions. We successfully catalyzed the hydrogenation reaction with 10 mol% [Ir(1,5-COD)Cl]2, [Ir(OMe)(1,5-COD)]2, RuCl2(PPh3)3 and RhCl(PPh3)3, where full conversions occured. Minor conversions were shown using catalysts [Ru(p-cimen)Cl2]2, IrCl3 x H2O and [Ir(1,5-COD)Cl]2 with the addition of MandyPhos ligand.

• Keywords: hydrogenation, acrylic ester, catalyst, ligand