Synthesis of methyl orange using ionic liquids

Astolfi, Danette L.; Mayville, Francis C

doi:10.1016/j.tetlet.2003.10.036

Cited by 14 publications

(10 citation statements)

References 11 publications

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“…ILs 2 a and 2 b were commercially available, while 2 c [30] and 2 d [31] were obtained by known procedures. In all cases, ILs were dried under vacuum (60-70 8C at < 0.001 mmHg) for 6 h before use.…”

Section: Methodsmentioning

confidence: 99%

Characterizing Ionic Liquids as Reaction Media through a Chemical Probe

Dichiarante

Betti

Fagnoni

et al. 2007

Chemistry A European J

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The triplet N,N-dimethylaminophenyl cation, a highly reactive but chemospecific electrophile, has been used as a probe for characterizing the properties of reaction media for a series of imidazolium ILs. With the N-hexyl-N-methyl imidazolium derivatives (not with the N-butyl analogues), hydrogen transfer leading to the aniline was the main process. Trapping by iodide occurred with an inverse dependence on viscosity. Trapping by pi nucleophiles exhibited a more complex behavior. This was explained by the effect of both the bulk viscosity and the structure of the IL cation on both steps of the reaction, namely, initial electrophilic attack and ensuing cation elimination or nucleophile addition. However, with an excellent nucleophile, such as thiophene, or when the latter step was intramolecular, as with 4-pentenol, the difference was obliterated and trapping became uniform. Incorporation of the probe into the IL cation (through insertion into the C--H bond alpha to the imidazolium ring) was demonstrated, while no addition to the anion tested (including bis(trifluoromethanesulfonimide)) took place.

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Section: Methodsmentioning

confidence: 99%

Characterizing Ionic Liquids as Reaction Media through a Chemical Probe

Dichiarante

Betti

Fagnoni

et al. 2007

Chemistry A European J

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“…A number of simpler heterocyclic perchlorate salts have also been prepared previously, with imidazolium, [7] 1-methylimidazolium, [8] 1-butyl-3-methylimidazolium, [9] 1,3-dibutylimidazolium, [10] and 1-hexyl-3-methylimidazolium cations. [11] The two predominant routes to such perchlorate-containing materials have been either through the protonation of a ring nitrogen using perchloric acid, resulting in the formation of Abstract: New, potentially green, and efficient synthetic routes for the remediation and/or re-use of perchloratebased energetic materials have been developed. Four simple organic imidazolium-and phosphonium-based perchlorate salts/ionic liquids have been synthesized by simple, inexpensive, and nonhazardous methods, using ammoni-um perchlorate as the perchlorate source.…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid‐Based Routes to Conversion or Reuse of Recycled Ammonium Perchlorate

Cordes

Śmiglak

Hines

et al. 2009

Chemistry A European J

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New, potentially green, and efficient synthetic routes for the remediation and/or re-use of perchlorate-based energetic materials have been developed. Four simple organic imidazolium- and phosphonium-based perchlorate salts/ionic liquids have been synthesized by simple, inexpensive, and nonhazardous methods, using ammonium perchlorate as the perchlorate source. By appropriate choice of the cation, perchlorate can be incorporated into an ionic liquid which serves as its own electrolyte for the electrochemical reduction of the perchlorate anion, allowing for the regeneration of the chloride-based parent ionic liquid. The electrochemical degradation of the hazardous perchlorate ion and its conversion to harmless chloride during electrolysis was studied using IR and (35)Cl NMR spectroscopies.

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“…The first step (as in ref. [12]) is the formation of dipolar intermediate 9 , however, its life time evidently increases in ionic liquids able to solvate both positively and negatively charged particles or molecule moieties [15–17]. Therefore, the second molecule of diethyl acetylenedicarboxylate 12 has time to enter a reaction with intermediate 9, generating the second intermediate 14, which is transformed to final compound 13 .…”

Section: Resultsmentioning

confidence: 99%

“…In addition, they are recyclable and can be used several times in the same reactions. Moreover, many reactions gain acceleration in ILs due to stabilization of charged intermediates or ions [15–17]. The realization of different reactions in ILs pertains to a new prospective field of organic chemistry—“green chemistry.”…”

Section: Introductionmentioning

confidence: 99%