Novel Brønsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts

Cole, Amanda C.; Jensen, Jessica L.; Ntai, Ioanna; Tran, Kim; Weaver, Kristin J.; Forbes, David C.; Davis, James H.

doi:10.1021/ja026290w

Cited by 1,174 publications

(661 citation statements)

References 17 publications

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“…A second rationale for the inclusion of a functional group in an IL is to imbue the salt with a capacity to covalently bind to or catalytically activate a dissolved substrate. For example, a primary amine functionalized imidazolium salt can separate CO 2 from gas streams (10), while ILs bearing appended sulfonic acid groups were used as solvent-catalyst for esterification (11). During past five years various types of TSILs have been designed to accomplish the specific tasks like catalysis, organic synthesis, chiral induction, synthesis and stabilization of nanomaterials, electrochemical applications, catalyst surface modifiers, etc., and they have been comprehensively reviewed by various authors.…”

Section: In 1969mentioning

confidence: 99%

Recent developments of task-specific ionic liquids in organic synthesis

Sawant

Raut

Darvatkar

et al. 2011

Green Chemistry Letters and Reviews

159

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Section: In 1969mentioning

confidence: 99%

Recent developments of task-specific ionic liquids in organic synthesis

Sawant

Raut

Darvatkar

et al. 2011

Green Chemistry Letters and Reviews

159

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“…They are also widely considered as liquid solvents to promote chemical reactions. 4,5 From a practical point of view, for an IL to be used as an industrial solvent it needs to be transported (pumped) across multiple unit operations and therefore it must be in the liquid phase.…”

Section: Introductionmentioning

confidence: 99%

New quantum chemistry-based descriptors for better prediction of melting point and viscosity of ionic liquids

Mehrkesh

Karunanithi

2016

Fluid Phase Equilibria

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Ionic liquids (ILs) are an emerging group of chemical compounds which possess promising properties such as having negligible vapor pressure. These so called designer solvents have the potential to replace volatile organic compounds in industrial applications. A large number of ILs, through the combination of different cations and anions, can potentially be synthesized. In this context, it will be useful to intelligently design customized ILs through computer-aided methods. Practical limitations dictate that any successful attempt to design new ILs for industrial applications requires the ability to accurately predict their melting point and viscosity as experimental data will not be available for designed structures. In this paper, we present two new correlation equations towards the more precise prediction of melting point and viscosity of ILs solely based on the inputs from quantum chemistry calculations (no experimental data or simulation results are needed). To develop these correlations we utilized data related to size, shape, and electrostatic properties of cations and anions that constitutes ILs. In this work, new descriptors such as dielectric energy of cations and anions as well as the values predicted by an 'ad-hoc' model for the radii of cations and anions (instead of their van der waals radii) were used. An enormous form of correlation equations constituent of all different combinations of descriptors (as the inputs to the model) were tested. The average relative errors were measured to be 3.16% and 6.45% for the melting point, Tm, and ln(vis), respectively.

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“…Examples are known, such as SO 3 H-functionalized ionic liquids, which were prepared through the acidification of zwitterions containing alkanesulfonic groups by various strong donor acids. [21][22] Furthermore, CO 2 -philic ionic liquid materials were prepared by alkalizing zwitterions with quaternary ammonium hydroxides. [23] Therefore, it is very interesting to introduce zwitterions into mesoporous silica materials; this means that acidic and basic seeds with a fixed molar ratio and position can be introduced into the silica framework.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Properties of Two Zwitterionic Hybrid SBA‐15 Mesoporous Silicas

Yang

Wang

et al. 2012

Eur J Inorg Chem

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Zwitterionic hybrid SBA-15 mesoporous silica materials containing both amine and sulfonic acid groups have been synthesized through cocondensation from as-synthesized zwitterionic siloxane precursors (ZS) with tetraethoxysilane (TEOS). Characterization by XRD, TEM, and N 2 adsorptiondesorption measurements show that the as-synthesized materials have ordered mesostructures. Analysis with UV, 29 Si/ 13 C cross-polarization magic angle spinning (CP-MAS) NMR, and X-ray photelectron spectroscopy (XPS) and elemental analysis demonstrates that the zwitterionic parts have been IntroductionOrdered mesoporous silica materials, such as the representative MCM-41 [1] and SBA-15, [2] with stable mesostructures, large surface areas, and size-tailored mesopores on the nanometer scale have been widely investigated and employed in many fields. Organically functionalized mesoporous silicas, in particular, have received considerable attention because various organic functional groups enlarge their practical applications to catalysis, separation, sensor, and drug delivery. [3][4] Mesoporous silicas functionalized with acidic groups, such as sulfonic acid, Nafion, and carboxyl groups, show high activity and selectivity for classical acidpromoted organic reactions, such as esterification, FriedelCrafts acylation, and olefin polymerization. [5][6][7][8][9] Various Ngroup-modified mesoporous silicas have been used in some base-catalyzed reactions including the Heck reaction, Knoevenagel condensation, and Michael addition. [10][11][12] Recently, base-and acid-bifunctional mesoporous catalysts were developed and received great attention because a cooperative catalytic system constructed from general acid and base groups is desired for some carbon-carbon bondformation reactions. [13][14][15] Lin et al. demonstrated that a general acid group, the ureidopropyl group, can activate substrates in cooperation with a general base group, the 3-[2- [a] [19][20] Kan et al. synthesized acid-base bifunctional mesoporous materials by controlling steric hindrance to prevent interactions between acid and base. [13] Although much effort has been made, precise control of the molar ratio and distribution of the acid and base centers to avoid their neutralization is still a big challenge. Zwitterions are neutral molecules with a positive and a negative electrical charge at different locations within the molecule. Their latent acidity (or basicity) could be obtained by combining 1:1 molar quantities of zwitterions with acids (or bases) possessing sufficiently low pK a (or pK b ) to convert the acidic (or basic) groups into the corresponding acids (or bases). Examples are known, such as SO 3 H-functionalized ionic liquids, which were prepared through the acidification of zwitterions containing alkanesulfonic groups by various strong donor acids. [21][22] Furthermore, CO 2 -philic ionic liquid materials were prepared by alkalizing zwitterions with quaternary ammonium hydroxides. [23] Therefore, it is very interesting to introduce zwitterions into mesoporous ...

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Novel Brønsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts

Cited by 1,174 publications

References 17 publications

Recent developments of task-specific ionic liquids in organic synthesis

Recent developments of task-specific ionic liquids in organic synthesis

New quantum chemistry-based descriptors for better prediction of melting point and viscosity of ionic liquids

Synthesis, Characterization, and Catalytic Properties of Two Zwitterionic Hybrid SBA‐15 Mesoporous Silicas

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