3-Methylpiperidinium ionic liquids

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dc.contributor.authorBelhocine, Tayebes_ES
dc.contributor.authorForsyth, Stewart A.es_ES
dc.contributor.authorGunaratne, H. Q. Nimales_ES
dc.contributor.authorNieuwenhuyzen, Markes_ES
dc.contributor.authorNockemann, Peteres_ES
dc.contributor.authorVaca Puga, Albertoes_ES
dc.contributor.authorSeddon, Kenneth R.es_ES
dc.contributor.authorSrinivasan, Geethaes_ES
dc.contributor.authorWhiston, Keithes_ES
dc.contributor.funderINVISTA
dc.contributor.funderEngineering and Physical Sciences Research Council, Reino Unido
dc.date.accessioned2016-10-11T11:56:11Z
dc.date.available2016-10-11T11:56:11Z
dc.date.issued2015
dc.description.abstract[EN] A wide range of room temperature ionic liquids based on the 3-methylpiperdinium cation core were produced from 3-methylpiperidine, which is a derivative of DYTEKs (R) A amine. First, reaction with 1-bromoalkanes or 1-bromoalkoxyalkanes generated the corresponding tertiary amines (Rm beta pip, R = alkyl or alkoxyalkyl); further quaternisation reactions with the appropriate methylating agents yielded the quaternary [Rmm(beta)pip]X salts (X-= I-, [CF3CO2]-or [OTf](-); Tf = -SO2CF3), and [Rmm(beta)pip][NTf2] were prepared by anion metathesis from the corresponding iodides. All [NTf2]-salts are liquids at room temperature. [Rmm(beta)pip]X (X-= I-, [CF3CO2]-or [OTf](-)) are low-melting solids when R = alkyl, but room temperature liquids upon introduction of ether functionalities on R. Neither of the 3-methylpiperdinium ionic liquids showed any signs of crystallisation, even well below 0 degrees C. Some related non-C-substituted piperidinium and pyrrolidinium analogues were prepared and studied for comparison. Crystal structures of 1-hexyl-1,3-dimethylpiperidinium tetraphenylborate, 1-butyl-3-methylpiperidinium bromide, 1-(2-methoxyethyl)1- methylpiperidinium chloride and 1-(2-methoxyethyl)-1-methylpyrrolidinium bromide are reported. Extensive structural and physical data are collected and compared to literature data, with special emphasis on the systematic study of the cation ring size and/or asymmetry effects on density, viscosity and ionic conductivity, allowing general trends to be outlined. Cyclic voltammetry shows that 3-methylpiperidinium ionic liquids, similarly to azepanium, piperidinium or pyrrolidinium counterparts, are extremely electrochemically stable; the portfolio of useful alternatives for safe and high-performing electrolytes is thus greatly extended.en_EN
dc.description.accrualMethodSes_ES
dc.description.bibliographicCitationBelhocine, T.; Forsyth, SA.; Gunaratne, HQN.; Nieuwenhuyzen, M.; Nockemann, P.; Vaca Puga, A.; Seddon, KR.... (2015). 3-Methylpiperidinium ionic liquids. Physical Chemistry Chemical Physics. 17(16):10398-10416. doi:10.1039/C4CP05936Kes_ES
dc.description.issue16es_ES
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dc.description.sponsorshipWe would like to acknowledge the EPSRC NCS in Southampton for the single crystal X-ray diffraction data collection and INVISTA Intermediates for funding.
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dc.identifier.doi10.1039/C4CP05936K
dc.identifier.issn1463-9076
dc.identifier.pmid25669485
dc.identifier.urihttps://riunet.upv.es/handle/10251/71621
dc.languageEspañoles_ES
dc.publisherRoyal Society of Chemistryes_ES
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dc.rightsReserva de todos los derechoses_ES
dc.rights.accessRightsAbiertoes_ES
dc.subject.classificationQUIMICA ANALITICAes_ES
dc.title3-Methylpiperidinium ionic liquidses_ES
dc.typeArtículoes_ES
dc.type.versioninfo:eu-repo/semantics/publishedVersiones_ES
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