INVISTA Intermediates

Wilton, United Kingdom

INVISTA Intermediates

Wilton, United Kingdom
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Belhocine T.,Queen's University of Belfast | Forsyth S.A.,INVISTA Intermediates | Gunaratne H.Q.N.,Queen's University of Belfast | Nieuwenhuyzen M.,Queen's University of Belfast | And 4 more authors.
Green Chemistry | Year: 2011

New ionic liquids based on azepanium and 3-methylpiperidinium cations have been synthesised; they exhibit moderate viscosities and remarkably wide electrochemical windows, thereby showing promise, inter alia, as electrolytes and battery materials, and as synthetic media. © 2011 The Royal Society of Chemistry.


Belhocine T.,Queen's University of Belfast | Forsyth S.A.,INVISTA Intermediates | Gunaratne H.Q.N.,Queen's University of Belfast | Nieuwenhuyzen M.,Queen's University of Belfast | And 5 more authors.
Green Chemistry | Year: 2011

The seven-member alicyclic secondary amine, azepane, has been used as starting material to synthesise a new family of room temperature ionic liquids. Such useful transformations of this coproduct of diamine production processes, generated in large amounts in the polyamide industry, would mitigate its disposal, which usually involves combustion. Reaction of azepane with 1-bromoalkanes or 1-bromoalkoxyalkanes produced the corresponding tertiary amines with good selectivity; further quaternisation reactions with the appropriate methylating agents yielded quaternary azepanium salts, [Rmazp]X (R = alkyl or alkoxyalkyl; X - = I -, [CF 3CO 2] - or [OTf] -; Tf = (trifluoromethyl)sulfonyl). Analogous [NTf 2] - salts have also been produced by metathetic reactions. Liquid temperature ranges are significantly affected by the nature of the anion and the substituents on the azepanium cation core; for example, [CF 3CO 2] - or [OTf] - salts based on cations with alkyl substitution are solids, whereas those with alkoxyalkyl substitution are liquids at ambient temperature. The crystal structures of [C 4mazp][CF 3CO 2], [C 4mazp]I and [C 6mazp][NTf 2] (C 4 = butyl, C 6 = hexyl) are reported. The effects of the structural features of cations and anions on density, viscosity and conductivity data are discussed. The presence of ether linkages in the cationic side chains causes a marked decrease in viscosities and an increase in conductivities. Cyclic voltammetry showed that azepanium ionic liquids exhibit extremely wide electrochemical windows, thus becoming promising and safe alternatives to electrolytes based on volatile organic compounds. This journal is © The Royal Society of Chemistry.


Belhocine T.,Queen's University of Belfast | Forsyth S.A.,INVISTA Intermediates | Gunaratne H.Q.N.,Queen's University of Belfast | Nieuwenhuyzen M.,Queen's University of Belfast | And 6 more authors.
Physical Chemistry Chemical Physics | Year: 2015

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 DYTEK® A amine. First, reaction with 1-bromoalkanes or 1-bromoalkoxyalkanes generated the corresponding tertiary amines (Rmβpip, R = alkyl or alkoxyalkyl); further quaternisation reactions with the appropriate methylating agents yielded the quaternary [Rmmβpip]X salts (X- = I-, [CF3CO2]- or [OTf]-; Tf = -SO2CF3), and [Rmmβpip][NTf2] were prepared by anion metathesis from the corresponding iodides. All [NTf2]- salts are liquids at room temperature. [Rmmβpip]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 °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. © the Owner Societies 2015.


Gunaratne H.Q.N.,Queen's University of Belfast | Langrick C.R.,INVISTA Intermediates | Puga A.V.,Queen's University of Belfast | Puga A.V.,Polytechnic University of Valencia | And 2 more authors.
Green Chemistry | Year: 2013

Polyetheretherketones were successfully synthesised in an ionic liquid, namely 1-butyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}amide, by polycondensation reactions of hydroquinone with 4,4′-dihalobenzophenones in the presence of potassium carbonate at elevated temperatures (up to 320 °C). The materials thus produced were similar to polymers prepared in the solvent usually employed in commercial processes, i.e. diphenyl sulfone, as suggested by spectroscopic techniques and X-ray crystallography. By replacing volatile diphenyl sulfone with the effectively involatile ionic liquid, the separation efficiency was significantly improved but the molecular weights were lower. © 2013 The Royal Society of Chemistry.

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