Benzenesulfonic Acids and Their Derivatives

Lindner, Otto; Rodefeld, Lars

doi:10.1002/14356007.a03_507

Cited by 10 publications

(8 citation statements)

References 68 publications

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“…The synthesis of ptsa is performed via direct sulfonation of toluene. 20 It is used in a very broad range of applications, e.g., as a catalyst, detergent solubilizer, resin hardener, in pharmaceuticals, or as an intermediate in the production of saccharine. 21,22 In the literature, different ptsa-based DESs have already been reported, but barely characterized, e.g., ptsa:choline chloride at a molar ratio of 1:1, ptsa:benzyltrimethylammonium chloride at a molar ratio of 2.3:1, ptsa: allyltriphenylphosphonium bromide at a molar ratio 3:1, or ptsa:n,n-diethylenethanol ammonium chloride.…”

Section: Introductionmentioning

confidence: 99%

p-Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides

Rodriguez

Machiels

Binnemans

2019

ACS Sustainable Chem. Eng.

126

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Combinations of p-toluenesulfonic acid monohydrate with different hydrogen-bond acceptors (i.e., choline chloride, tetraethylammonium chloride, tetrabutylammonium chloride, betaine hydrochloride, β-alanine, tetrabutylphosphonium chloride, ethylammonium chloride, methyltriphenylphosphonium bromide, and benzyltriphenylphosphonium chloride) were tested for deep-eutectic solvent (DES) formation. Only p-toluenesulfonic acid monohydrate:choline chloride, p-toluenesulfonic acid monohydrate:tetrabutylammonium chloride, and p-toluenesulfonic acid monohydrate:tetrabutylphosphonium chloride at a 1:1 molar ratio remained liquid at room temperature. The obtained deep-eutectic solvents were characterized by determining their density and viscosity as function of temperature, and their thermal operational window (i.e., decomposition temperature and melting point/glass transition temperature). Moreover, IR spectroscopy was used to elucidate the formation of hydrogen bonds. The solubility of different metal oxides in the DES p-toluenesulfonic acid monohydrate:choline chloride was experimentally determined. The effect of the hydrogen-bond donor:hydrogen-bond acceptor molar ratio (2:1, 1:1, and 1:2) on the metal oxide solubility was explored. A comparison was made with metal oxide solubilities in other choline chloride-based DESs and in acidic aqueous solutions.

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Section: Introductionmentioning

confidence: 99%

p-Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides

Rodriguez

Machiels

Binnemans

2019

ACS Sustainable Chem. Eng.

126

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“…Eur.J.2015, 21,18631 -18641 www.chemeurj.org one-pot method, there appears to be an equitabler atio between both moieties, thus suggesting as imilar reactivity of both anilines towardS WCNTs. This outcomei sc ontrary to what could be initially expected because sulfanilic acid should be much more reactive toward isopentyl nitrite than the majority of anilines owing to the powerful electron-withdrawing effect of SO 3 Hg roups (sulfanilic acid is aw ell-known analytical standard for nitrite quantification) [15] so its diazonium derivatives should interactw ith the SWCNTsf irst. This unexpected result allows the simple use of both anilines in ao ne-pot system and controlo ft he ratio between the hydrophilic and functional moieties by choosing the experimental procedure.…”

Section: Degreeo Ff Unctionalizationmentioning

confidence: 70%

“…Benzenesulfonic acids have one of the highest water solubilities amongst organic compounds, which is due to large dissociation constants, hence the outstanding ability of these species to ionize and be solvated by water. [15] There are some reported examples of the decoration of CNTsw ith benzenesulfonic motifs (a process that is hereafter termeds ulfonation). Hudson and et al used oleum (SO 3 -saturated H 2 SO 4 ) to functionalize CNT sidewalls by using am odified diazonium reactionw ith radical initiators.…”

Section: Introductionmentioning

confidence: 99%

Multipurpose Nature of Rapid Covalent Functionalization on Carbon Nanotubes

González‐Domínguez

Santidrián

Criado

et al. 2015

Chemistry A European J

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In the vast field of functionalization routes to carbon nanoforms, the fulfillment of such critical requirements as quick and nonharsh methods, good dispersibility, introduction of reactive groups, short reaction time, and low cost can be quite challenging. Traditional thermally induced diazonium chemistry on single-walled carbon nanotubes (SWCNTs) is revisited by using commercial anilines and providing useful insight into the versatility of this approach. Functionalized SWCNTs with multiple controllable features, such as degree (and ratio) of coverage, orthogonalization, doping, and high water dispersibility, are obtained by introducing benzenesulfonic acid and benzylamine moieties. The scenario opens up an avenue to address relevant applications in which most functionalization methods could not be applied in a straightforward way.

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“…These procedures generally employ heavy metals (Sharma et al, 2002; Shibata et al, 2005; Panda and Sarkar, 2008; Gadda et al, 2010; Tsui et al, 2012) or chlorine chemistry in the form of leaving groups, i.e., tosylate, mesylate etc. (Grubb and Branchaud, 1997; Lindner and Rodefeld, 2001; Adaligil et al, 2007).…”

Section: -Memebered Heterocyclesmentioning

confidence: 99%

Dialkyl Carbonates in the Green Synthesis of Heterocycles

2019

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This review focuses on the use of dialkyl carbonates (DACs) as green reagents and solvents for the synthesis of several 5- and 6-membered heterocycles including: tetrahydrofuran and furan systems, pyrrolidines, indolines, isoindolines, 1,4-dioxanes, piperidines, and cyclic carbamates. Depending on the heterocycle investigated, the synthetic approach used was different. Tetrahydrofuran systems, pyrrolidines, indolines, isoindoline, and 1,4-dioxanes were synthesized using dimethyl carbonate (DMC) as sacrificial molecule (B Ac 2/B Al 2 mechanism). Cyclic carbamates, namely 1,3-oxazin-2-ones, were prepared employing DACs as carbonylating agents, either by B Ac 2/B Al 2 mechanism or through a double B Ac 2 mechanism. Piperidines were synthetized taking advantage of the anchimeric effect of a new family of dialkyl carbonates, i.e., mustard carbonates. Finally, in the case 5-hydroxymethylfurfural (HMF), DMC has been employed as efficient extracting solvent of this extensively investigated bio-based platform chemical from the reaction mixture. These synthetic approaches demonstrate, once again, the great versatility of DACs and their—yet to be fully explored—potential as green reagents and solvents in the synthesis of heterocycles.

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Benzenesulfonic Acids and Their Derivatives

Cited by 10 publications

References 68 publications

p-Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides

p-Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides

Multipurpose Nature of Rapid Covalent Functionalization on Carbon Nanotubes

Dialkyl Carbonates in the Green Synthesis of Heterocycles

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