MCM-41-supported metal bis[(perfluoroalkyl)sulfonyl]imides as heterogeneous catalysts for aromatic nitration

Yuan, Yiping; Nie, Jun; Zhengbo, Zhang; Wang, Shuojin

doi:10.1016/j.apcata.2005.08.014

Cited by 24 publications

(12 citation statements)

References 25 publications

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“…683 These hybrid materials could have some potential as near-infraredemitting materials, but this has not been investigated yet. 684 The same remark can be made for lanthanide(III) triflates impregnated in MCM-41. 685 The [Eu(dbm) 3 (phen)] complex was formed in situ in mesophase thin films, which were prepared by hydrolysis of TEOS in the presence of Pluronic P123 triblock copolymer surfactant.…”

Section: Mesoporous Silicatesmentioning

confidence: 72%

Lanthanide-Based Luminescent Hybrid Materials

2009

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Koen Binnemans was born in Geel, Belgium, in 1970. He obtained his M. Sc. degree (1992) and Ph.D. degree (1996) in Chemistry at the Catholic University of Leuven, under the supervision of Prof. C. Go ¨rller-Walrand. In the period 1999-2005, he was a postdoctoral fellow of the Fund for Scientific Research Flanders (Belgium). He did postdoctoral work with Prof. Jacques Lucas (Rennes, France) and Prof. Duncan W. Bruce (Exeter, U.K.). In 2000, he received the first ERES Junior Award (ERES, European Rare-Earth and Actinide Society). From 2002 until 2005, he was (parttime) associate professor. Presently, he is professor of chemistry at the Catholic University of Leuven. His current research interests are metalcontaining liquid crystals (metallomesogens), lanthanide-mediated organic reactions, lanthanide spectroscopy, luminescent molecular materials, and ionic liquids.

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Section: Mesoporous Silicatesmentioning

confidence: 72%

Lanthanide-Based Luminescent Hybrid Materials

2009

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“…But the para/ortho ratios of the products were almost similar whether the reactions were carried out in 1,2-dichloroethane or in ionic liquids and the results were consistent with those reported in literature. 4,11,17,19 Since Cu[N(C 4 F 9 SO 2 ) 2 ] 2 /[N 4446 ][Tf 2 N] system was too effective for the nitration of toluene to understand the differences between the catalytic reactions, chlorobenzene, a relatively deactivated compound, was selected as the substrate to optimize the reaction conditions and the results of this set of experiments are shown in Table 2.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3] One of these strategies is the use of Lewis acid catalysts such as lanthanide perfluoroalkylsulfonates [4][5][6][7][8][9] and metal bis[(perfluoroalkyl)-sulfonyl]imides. [10][11][12] On the other hand, ionic liquids (IL) as green solvents have been used in many organic reactions because of their thermal stability, negligible vapor pressure and reusability. 13,14 In the past few years a number of researches for nitration of aromatics have been reported in which ionic liquids act as solvents.…”

Section: Introductionmentioning

confidence: 99%

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

2008

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The nitrations of substituted benzenes proceeded rapidly and cleanly with very good yields in Cu (N N] catalyst system, in which HNO 3 /Ac 2 O was used as the nitrating agent. For the nitration of chlorobenzene when 2 mol% catalyst was used at room temperature for 10 min, 87.6% and 90.6% of conversion of chlorobenzene were achieved, respectively and the para/ortho ratios of products were about 4.3-4.8. The catalyst systems with ionic liquid could be recovered easily and reused more than 5 times.

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“…Alternative systems developed recently for nitration of deactivated aromatics include nitric acid in the presence of P 2 O 5 supported on silica gel [18], nitrogen dioxide at low temperatures in the presence of ozone [19], N 2 O 5 in the presence of Fe(acac) 3 as a catalyst [20], urea nitrate and nitrourea [21], nitroguanidine and ethylene glycol dinitrate in concentrated acid [22], vanadium(V) oxytrinitrate in dichloromethane at room temperature [23], and nitric acid in the presence of MCM-41-supported metal bis[(perfluoroalkyl)sulfonyl]imides in dichloroethane [24]. However, such reagents still give mainly the meta-products and moreover, ortho-isomers are often formed in relatively high proportions.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Nitration of Deactivated Mono-Substituted Benzenes Using Acyl Nitrates Over Reusable Acidic Zeolite Catalysts

2010

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Nitration of benzonitrile was investigated using a nitric acid/acid anhydride/zeolite catalyst system under different reaction conditions. Trifluoroacetic and chloroacetic anhydrides were found to be the most active among the anhydrides tried. Also, zeolites Hb and Fe 3? b (Si/ Al = 12.5) were found to be the most active catalysts. For example, nitration of benzonitrile with trifluoroacetyl nitrate under reflux conditions in dichloromethane gave 3-and 4-nitrobenzonitriles in quantitative yield, of which the para-isomer represented 24-28%. The yield of para-isomer was improved to 33% when passivated Hb was used under similar reaction conditions. This is easily the most para-selective nitration of benzonitrile ever recorded. Also, no ortho-isomer was formed under the conditions tried. The zeolite can be easily recovered, regenerated by heating and reused up to six times to give results similar to those obtained with a fresh sample of the catalyst. The nitration system was applied successfully to a range of deactivated mono-substituted benzenes to give para-isomers in significantly higher proportions than in the corresponding traditional nitration reactions.

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MCM-41-supported metal bis[(perfluoroalkyl)sulfonyl]imides as heterogeneous catalysts for aromatic nitration

Cited by 24 publications

References 25 publications

Lanthanide-Based Luminescent Hybrid Materials

Lanthanide-Based Luminescent Hybrid Materials

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

Regioselective Nitration of Deactivated Mono-Substituted Benzenes Using Acyl Nitrates Over Reusable Acidic Zeolite Catalysts

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