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Exercise 12 Chlorobenzene and bromobenzene both undergo nitration more slowly than benzene. Does this mean that the rate of nitration of these compounds is controlled by the inductive effect or the resonance effect of the halogen atom?
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www.usm.maine.edu/~newton/Chy251_253/Lectures/EASReacti...
www.usm.maine.edu/~newton/Chy251_253/Lectures/EASReactions/EASIIFS.html
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The second, nitration of the chlorobenzene, serves to activate the molecule for nucleophilic aromatic substitution reaction needed to add formanilide to the substrate. Hydrogenation of the resulting diphenyl nitrate compound yields the desired 4-aminodiphenylamine.
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academic.uofs.edu/faculty/CANNM1/advancedorganic/advanc...
academic.uofs.edu/faculty/CANNM1/advancedorganic/advancedorganicmodule.htm
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Bauxite and alumina were reported to be ineffective as catalysts in the vapor phase nitration of benzene. In U.S. Pat. No. 4,107,220, the vapor phase nitration of chlorobenzene in the presence of molecular sieve catalysts having a pore size varying from about 5 .ANG.
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www.devileye.net/catalog/thoracoscopic_valve_prosthesis...
www.devileye.net/catalog/thoracoscopic_valve_prosthesis_delivery/vapor_phase_nitration_catalysts.html
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3928476 Process for nitration of halogenated benzene derivatives ... 4107220 Gas phase nitration of chlorobenzene ... WHAT IS CLAIMED IS: 1. A process for the nitration of halobenzenes, wherein the reaction is carried out in the presence of a sulfonic acid in an amount which is sufficient to produce a para directive...
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www.freepatentsonline.com/EP0025348.html
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The nitration of benzene proceeds smoothly to give nitrobenzene near quantitative yield, in the hydrophobic ionic liquid [C 10 mim][OTf]. The nitration of chlorobenzene was much slower than with benzene, but gave 2- and 4-nitrochlorobenzene in excellent yield, in a 3.0:1.0 para:ortho-isomer ratio.
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www.freepatentsonline.com/6906231.html
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This example illustrates the nitration of chlorobenzene with concentrated nitric acid in the presence of ZSM-5 zeolite catalyst having a Si/Al ratio of 280. 40 ml of chlorobenzene was mixed with 5 g of H-ZSM-5 catalyst in a three neck, roundbottom flask and stirred.
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www.patentgenius.com/patent/5946638.html
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The present invention relates to a continuous adiabatic process for preparing nitrochlorobenzene, in which the waste sulfuric acid produced during the practice of the process is reconcentrated and recycled into the nitration reaction. ... The feedstocks used in the process according to the invention are chlorobenzene,
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www.patentgenius.com/patent/6586645.html
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Increased formation of the p-isomer in the nitration of chlorobenzene eases the isomeric separation to a considerable extent and helps to save energy.
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www.rsc.org/ej/CC/2000/a908011b.pdf
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90 mL of chlorobenzene is added dropwise with a dropper pipet or buret to a previously prepared, and cooled to room temperature, mixture of 110 mL of 99% nitric acid and 185 mL of 99% sulfuric acid, in a 1000-mL beaker, while the mixture is stirred mechanically with a magnetic stirrer.
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web.mit.edu/semenko/Public/Military%20Manuals/RogueSci-...
web.mit.edu/semenko/Public/Military%20Manuals/RogueSci-Mirror/explo/dinitrochlorobenzene.html
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