Catalysed oxidation of quinoline in model fuel and the selective extraction of quinoline n oxide with imidazoline based ionic liquids

Catalysed oxidation of quinoline in model fuel and the selective extraction of quinoline N oxide with imidazoline based ionic liquids Egyptian Journal of Petroleum xxx (2017) xxx–xxx Contents lists av[.]

Egyptian Journal of Petroleum xxx (2017) xxx–xxx Contents lists available at ScienceDirect Egyptian Journal of Petroleum journal homepage: www.sciencedirect.com Full Length Article Catalysed oxidation of quinoline in model fuel and the selective extraction of quinoline-N-oxide with imidazoline-based ionic liquids Adeniyi S Ogunlaja a,⇑, Olalekan S Alade b a b Department of Chemistry, Nelson Mandela Metropolitan University, P.O Box 77000, Port-Elizabeth 6031, South Africa Petroleum and Petrochemical Engineering Laboratory, Department of Chemical Engineering, Obafemi Awolowo University, Ile-Ife, Osun State, Nigeria a r t i c l e i n f o Article history: Received December 2016 Revised February 2017 Accepted 15 February 2017 Available online xxxx Keywords: Vanadium(IV) catalyst Hydrogen peroxide (H2O2) Quinoline Oxidation Ionic liquids a b s t r a c t Synthesised vanadium-coordinated N,N-bis(o-hydroxybenzaldehyde)phenylene diamine catalyst, [VO (sal-HBPD)] and supported catalyst, p[VO(sal-HBPD)] were employed for the oxidation of quinoline The use of [VO(sal-HBPD)] and p[VO(sal-HBPD)] for the oxidation of quinoline, (Quinoline-to-H2O2 ratio 1:7) showed oxidation selectivity as quinoline-N-oxide (100%) was recorded as the oxidation product Quinoline-N-oxide was confirmed as the oxidation product through GC–MS Density functional theory (DFT) revealed hydroxylperoxido-species [VOO(sal-HBPD)] (II) as the reactive oxidized oxidovanadium specie responsible for the oxidation Ionic liquids, 1-butyl-3-methylimidazolium chloride and 1-butyl3-methylimidazolium nitrate extracted 96% and 87% quinoline-N-oxide respectively Ó 2017 Egyptian Petroleum Research Institute Published by Elsevier B.V This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/) Introduction Environmental concerns have resulted in stringent specifications for petroleum products including fuel oils; and had necessitated the development of processes to upgrade heavy oil to environmental friendly products [1] The current crude oil reservoirs are known to be of heavier and sourer composition, i.e the produced oils (as well as their products) come with organosulfur,-oxygen and -nitrogen compounds also known as heteroatoms [2–4] The Organo-nitrogen and –sulfur compounds in fuels, are reported to (i) poison refining catalysts, (ii) emit NOx and SOx to the environment when combusted, hence reacting with water to form acid rain, (iii) reduce air quality, and (iv) possibly lead to global warming [5] The elimination of organosulfur compounds from fuel has been largely reported, through the use of hydrodesulfurization (HDS) process while literature reports on denitrogenation processes are limited Organo-nitrogen compound removal is required to maintain NOx emissions below regulatory levels of