Design, Synthesis, Characterization And Properties Of Organophosphorous Ionic Liquids

Ionic liquids as the rise of an important class of compounds in the background of greenchemistry, presenting unique physical and chemical properties, have been widely used inorganic synthesis and catalysis, extraction and separation, electrochemistry, materials scienceand other fieids. Moreover, functionalized ionic liquids which get specific functional groups intheir cations and anions have received more attention. In this paper, design, synthesis andcharacterization of functionalized organophosphorous ionic liquids and their application topolymer poly(methyl methacrylate) have been studied.(1)1-(β-cyanoethyl) imidazole was synthesized by addition reaction between imidazoleand acrylonitrile in high yields. Then the quaternization between1-(β-cyanoethyl) imidazoleand1-bromoalkane led to alkyl substituted imidazolium salts in high yields. Finally, theN-alkyl-imidazoles such as N-propyl-imidazole, N-butyl-imidazole, N-pentyl-imidazole,N-hexyl-imidazole were efficiently synthesized by elimination of substituted imidazolium saltsin good yields. The products were characterized by MS, IR, NMR.(2) Diethyl phenylphosphonite and ethyl diphenylphosphinite were synthesized bynucleophilic substitution reactin between dichlorophenylphosphine or chlorodiphenylphosphineand ethanol in moderate yields. Then3-bromopropyl phenyl ehoxylphosphine oxide and3-bromopropyl diphenylphosphine oxide were synthesized by Arbuzov reaction betweendiethyl phenylphosphonite or ethyl diphenylphosphinite and1,3-dibromopropane in goodyields. The complexes were characterized.(3) Different types of hydrophobic organophosphorous ionic liquids were prepared first fromN-alkyl-imidazoles such as N-propyl-imidazole, N-butyl-imidazole, N-pentyl-imidazole,N-hexyl-imidazole and3-bromopropyl phenylehoxylphosphine oxide or3-bromopropyldiphenylphosphine oxide in Microwave reactor, then carry out anion exchange withbis(trifluoromethylsulfonyl)amide lithium salt or potassium hexafluorophosphate salt. The products were also characterized.(4) Six kinds of organophosphorous ionic liquids were used in plasticizering PMMA, theexperimental results showed that our synthesized organophosphorous ionic liquids all couldgenerate plasticization of PMMA, all of them were able to lower the glass transitiontemperature of PMMA and PMMA melt viscosity. In particular, organophosphorous ionicliquids3-[3-(diphenylphosphono)propyl]-1-propyl-1H-imidazoliumbis(trifluoromethylsulfonyl)amide had the best plasticization of PMMA, while ionic liquids1-butyl-3-[3-(diphenylphosphono)propyl]-1H-imidazolium hexafluorophosphate had the worstplasticization of PMMA. Also, the thermal stability of PMMA had not been changed.