A mild and efficient method for preparation of azides from alcohols using acidic ionic liquid [H-NMP]HSO4

Using metrics and sustainability considerations to evaluate the use of bio-based and non-renewable Brønsted acidic ionic liquids to catalyse Fischer esterification reactions

“…Brønsted acidic ionic liquids were created from the reaction between NMP and Brønsted acids according to the literature protocol [10]. It was felt necessary to consider RME/% Mass of desired product/Total mass of reactants used [4] E-factor Total mass waste/Mass of desired product [5] PMI Total mass required/Mass of desired product = E-Factor + 1 [6] gRME/% Mass of desired product=Total mass required ¼ 1 PMI [7] the origins of the ingredients in making these ionic liquids to preserve the sustainability of the esterification methodology that is reliant on them as catalysts.…”

“…For this work dichloromethane (DCM) was the solvent of choice. Other studies have employed benzene [9,14], as well as DCM as the solvent [10]. Obviously in the case of [H-NMP][OCym] this compromises the bio-based label that may be attributed to the final product.…”

“…The acidity of the ionic liquid may originate from a pendant sulphonic acid group on the cation, or the salt may be formed by the protonation of a lactam by a strong acid, while the resulting conjugate base acts as the anion (Scheme 1). Ionic liquids of the latter type, formed by the protonation of N-methyl pyrrolidine (NMP) have been demonstrated to assist several types of reaction including esterifications [10][11][12]. Although strictly speaking an acid-base equilibrium is unavoidable, the combination of NMP and a strong acid will be assumed to result wholly in the ionic product.…”

Multicomponent Reactions in Ionic Liquids

“…In this area Zolfigol et Hajipour et al and Hervai et al effected the same transformations, and extended the methodology to allow the use of urea as the amide source using a range of Brønstead acid based Ils (BAILs). [23], [24] Hajipor et al ' 4 ] has been used previously as an efficient and reusable catalyst for nitration of aromatic compounds and esterification of various alcohols by different acids. [25]- [27] The acidic nature of BAILs has been exploited as catalysts for many other significant organic reactions, which proceed with excellent yields and selectivities and demonstrate the great potential of these ILs in catalytic technologies for chemical production.…”

Synthesis, Characterization and Theoretical Study of the New Aluminate Ionic Liquid: Tetrahepthylammonium-bromotrichloroaluminate [(C7H15)4N]+[AlCl3Br]-

“…For example, during past years, ionic liquids have been applied to synthesize different compounds 4 , polymerization processes, dye synthesis, supercritical fluid chromatography, and determination of phenothiazine derivatives, preparation of sensors and biosensors, preparation of nanostructures, and other applications 5 .…”