Nitration of Substituted Benzenes Catalyzed by Metal Bis[(perfluoroalkyl)sulfonyl]imides in Quaternary Ammonium Ionic Liquids

Wang, Shuo-Jin; Sun, Zhiying; Nie, Jun

doi:10.1002/cjoc.200890400

Cited by 10 publications

(6 citation statements)

References 23 publications

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“…[75] Similarr esults were attained for the nitration of benzene derivatives with HNO 3 in the presence of the ILlanthanide (Ln)-based [N 4446 ][NTf 2 ]/Ln(N(C 4 F 9 SO 2 ) 2 ) 2 catalytic system (5 mol %). Importantly,t he catalytic systemsc ould be easily recovered and reused over five times in the reaction.…”

Section: Il-mediated Aromatic Nitrationsupporting

confidence: 58%

“…Importantly,t he catalytic systemsc ould be easily recovered and reused over five times in the reaction. [75] Similarr esults were attained for the nitration of benzene derivatives with HNO 3 in the presence of the ILlanthanide (Ln)-based [N 4446 ][NTf 2 ]/Ln(N(C 4 F 9 SO 2 ) 2 ) 2 catalytic system (5 mol %). [76] New acidic caprolactam-based ILs (X = OTs, PhSO 3 ,H SO 4 )e fficiently catalyzed aromatic nitration in the presence of NO 2 /air [77] or HNO 3 /acetic anhydride (Ac 2 O) as nitrating agents.…”

Section: Il-mediated Aromatic Nitrationsupporting

confidence: 58%

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Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

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Section: Il-mediated Aromatic Nitrationsupporting

confidence: 58%

Section: Il-mediated Aromatic Nitrationsupporting

confidence: 58%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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“…Recently, the use of lanthanide bis[(trifluoromethyl)sulfonyl]amides {Ln(Tf 2 N) 3 , Ln = La, Sm and Yb} as effective catalysts in quaternary ammonium ionic liquids ([N 444 H][Tf 2 N], [N 666 H][Tf 2 N], [N 2227 ][Tf 2 N], [N 4446 ][Tf 2 N] and [N 6666 ][Tf 2 N]) for the nitration of substituted benzenes was established 86. Nitric acid with a concentration of 95 % turns out to be the best nitrating agent.…”

Section: Lanthanide‐mediated Catalysis In Ilsmentioning

confidence: 99%

“…All the lanthanide bis[(trifluoromethyl)sulfonyl]amides {Ln(Tf 2 N) 3 , Ln = La, Sm and Yb} show catalytic activity in the nitration reaction and achieve nearly the same level of equilibrium in different ILs. It is worthy to note that this catalyst/ionic liquid system could be recovered by simple procedures and recycled for at least five times 86…”

Section: Lanthanide‐mediated Catalysis In Ilsmentioning

confidence: 99%

Ionic Liquids for Lanthanide and Actinide Chemistry

2010

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Ionic liquid chemistry has developed into a tremendously popular field of chemistry in the last decade. It has been realized that ionic liquids show features that cannot be realized in conventional molecular solvents. The widely tuneable class of ionic liquids has become important for lanthanide and actinide coordination chemistry, f‐element spectroscopy, f‐element electrochemistry and electrodeposition, organic synthesis and catalysis as well as inorganic nanomaterial synthesis. For example, ionic liquids offer the possibility to synthesize and crystallize quite uncommon lanthanide compounds. Ionic liquids can also be designed in such a way that they become excellent media to study the optical properties of lanthanide compounds. And even ionic liquids based on f‐elements can be made. Hydrophobic ionic liquids may replace organic solvents in liquid/liquid f‐element extraction processes, not only as a safer extraction phase but also as a smart extractant. Their wide electrochemical window and large ion conductivity make ionic liquids interesting solvents to study the electrodeposition of the very electropositive lanthanide elements. For f‐element‐catalyzed reactions, higher reaction rates, enhanced selectivity, better immobilization of the catalyst and an easy product recovery have often been observed in certain ionic liquids.

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“…Since the end of last century, with more and more recognition of room temperature ionic liquids (TSILs), a growing interests have also been witnessed in ionic liquids as solvents or catalysts for aromatic nitration. Aromatics nitration in imidazole based ionic liquid, 4-7 N-(4-hydroxysulfonylbutyl) pyridinium based ionic liquid, 8 quaternary ammonium based ionic liquid 9 and tetra-alkylphosphonium ionic liquids 10 were reported in succession. Although much success has been achieved, some problems still remained, for example, needing of a lot of ionic liquid, inconveniences in a continuous system and even some separation problems when they were used in some homogeneous reaction systems such as nitration of aromatic compounds with aqueous nitric acid.…”

Section: Introductionmentioning

confidence: 99%