Ionic liquids (ILs) are composed only of ions. Of special interest to this review are those where at least one ion (the cation) is organic and whose melting points are below or not far above room temperature. ILs are designated as "green" solvents because they have extremely low vapor pressure, are non-inflammable, and thermally and chemically stable. Therefore, many of them can be, in principle, recycled into the process indefinitely. The objective of the present review is to discuss different aspects of the use of ILs in carbohydrate chemistry, in particular, dissolution and functionalization of simple sugars, cyclodextrins, cellulose, starch, and chitin/chitosan. The molecular structure and synthesis of ILs most frequently employed in carbohydrate chemistry are discussed with an emphasis on imidazolium and pyridinium cations with different counterions. The physicochemical properties of ILs that are relevant to the dissolution and functionalization of carbohydrates, in particular their polarities and hydrogen-bonding abilities, are discussed. Dissolution of simple saccharides and biopolymers in ILs is presented with an emphasis on the mechanism of carbohydrate--IL interactions. Finally, the very interesting novel applications of the solutions obtained are addressed. These include, inter alia, spinning of the dissolved biopolymer into fibers, extrusion into slabs and rods, formation of matrixes for a myriad of substrates, including biomacromolecules, formation of nanocomposites, and functionalization to produce important derivatives. The use of ILs in many branches of science is expanding fast; it is hoped that this review will draw the attention of researchers to the "window of opportunities" that these green solvents open into carbohydrate chemistry.
Solubilization of 1,2-ethanediol, ED, and its aqueous solution, ED-W, by the reverse aggregates of sodium
bis(2-ethylhexyl) sulfosuccinate, Aerosol-OT or AOT, in n-heptane and isooctane has been studied by FTIR
and 1H NMR. Curve fitting of the νOD bands of the aggregate-solubilized (partially deuterated) ED and
ED-W showed the presence of a main peak and a smaller one. The frequency of the former peak decreases,
whereas its full width at half-height increases as a function of increasing [solubilizate]/[AOT]. The dependence
on the later ratio of 1H NMR chemical shifts, δproton, of solubilized water, ED, ED-W as well as the surfactant
discrete protons showed monotonic increase or decrease. Results of both techniques indicated that ED
and/or water interact with the surfactant by a similar mechanism, i.e., by solvating its head-ions. The
magnitudes of |ΔνOD| and |Δδproton| showed, however, that AOT interacts more strongly with ED than with
water. Over the entire range of [solubilizate]/[surfactant], the main νOD peak area corresponds to 85 ± 2%
(ED), and 88 ± 2% (ED-W) of the total peak area. These results show that the aggregate-solubilized ED
or ED-W does not seem to coexist in “layers” of different structures, as suggested by the multi-state water
solubilization model.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.