Ethylbenzene, nitration

Ethylbenzene, Nitrated Derivatives were patented by the late Dr Hale of PicArsn as colloiding agents for NC in manuf of smokeless propellants... 

Nitrate-o-ethylbenzene nitrate explosives are prepared by mixing of nitrate acid as oxidant and o-ethylbenzene as a flammable agent at specific weight ratios. The reaction of nitric acid and o-ethylbenzene can be described as follows ... 

The rates of nitration of benzene, toluene, and ethylbenzene in solutions of nitric acid c. 3-7 mol 1 ) in nitromethane were independent... 

The identification of a specific nitrating species can be approached by comparing selectivity with that of nitration under conditions known to involve the nitronium ion. Examination of part B of Table 10.7 shows that the position selectivity exhibited by acetyl nitrate toward toluene and ethylbenzene is not dramatically different from that observed with nitronium ion. The data for i-propylbenzene suggest a lower ortho para ratio for acetyl nitrate nitrations. This could indicate a larger steric factor for nitration by acetyl nitrate. 

Nitrated Solvent Naphtha (N.S.N.). As nitration of crude solvent naphtha by the usual one-stage method results in yields that are too low, because of oxidation, E. Blecher et al (Ref 3) proposed nitrating only the refined material, and in two stages. The two-stage method is described in Colver, pp 255 686—87 (Ref 4). The product consists chiefly of 2,4,6-Trinitro-mesitylene (see under Mesitylene and Deriva- tives in this Vol), and 3,5,6-trinitropseudocumene, with small quantities of the nitrated products of xylene, ethylbenzene, etc... 

Production of p-xylene via p-xylene removal, i.e., by crystallization or adsorption, and re-equilibration of the para-depleted stream requires recycle operation. Ethylbenzene in the feed must therefore be converted to lower or higher boiling products during the xylene isomerization step, otherwise it would build up in the recycle stream. With dual-functional catalysts, ethylbenzene is converted partly to xylenes and is partly hydrocracked. With mono-functional acid ZSM-5, ethylbenzene is converted at low temperature via transalkylation, and at higher temperature via transalkylation and dealkylation. In both cases, benzene of nitration grade purity is produced as a valuable by-product. 

Sanemasa, 1., Arakawa, S., Piao, C.Y., and Degnchi, T. Equilibrium solubilities of benzene, toluene, ethylbenzene, and propylbenzene in silver nitrate solntions. Bull Chem. Soc. Jpn., 58(10) 3033-3034, 1985. 

Both nitric acid and nitrogen dioxide, in the liquid and vapour phase, have been used for the nitration of the alkyl side chains of various alkyl-substituted aromatics without affecting the aromatic nucleus.Thus, treatment of ethylbenzene with nitric acid of 12.5 % concentration in a sealed tube at 105-108 °C is reported to generate a 44 % yield of phenylnitroethane. The nitration of toluene with nitrogen dioxide at a temperature between 20-95 °C yields a mixture of phenylnitromethane and phenyldinitromethane with the proportion of the latter increasing with reaction temperature. ... 

The important derivatives of benzene are shown in Table 8.8. Ethylbenzene is made from ethylene and benzene and then dehydrogenated to styrene, which is polymerized for various plastics applications. Cumene is manufactured from propylene and benzene and then made into phenol and acetone. Cyclohexane, a starting material for some nylon, is made by hydrogenation of benzene. Nitration of benzene followed by reduction gives... 

When ethylbenzene is nitrated, a mixture of ortho- and para-mononitrobenzenes in the... 

Dinitroetbylbenzene, mp 58.5°. It may be prepd from 2,3"dinitro-4-amino l-ethylbenzene and sodium nitrate in a mixture of alcohol and 20% oleum for 20 hours... 

Ethyl mono-nitropbenols. Beil (Ref 1) lists only one compd of unde determined structure, yel oil, bp 212-15°, with a Bo soft which expl on heating. Prepd by nitration of ethylbenzene followed by treatment with nitrous acid Refs l)Beil. 6, 475 2)W.Suida S.PIohn, Monarsh 1, 181 (1880)... 

Rb+- and Cs+-impregnated X zeolites were found to exhibit the highest activity and selectivity in these transformations. A CsX zeolite treated with boric acid, for example, gave better than 50% overall selectivity in the formation of styrene and ethylbenzene (410°C, 60% conversion).275 Treatment of these catalysts with copper or silver nitrate resulted in further improvements in catalyst performance.276 The promoting role of these metals was suggested to be their involvement in dehydrogenation of methyl alcohol. 

Exercise 22-11 Why do fairly reactive arenes, such as benzene, methyl benzene, and ethylbenzene, react with excess nitric acid in nitromethane solution at a rate that is independent of the concentration of the arene (i.e., zero order in arene concentration) Does this lack of dependence on arene concentration mean that nitration of an equimolar mixture of benzene and methylbenzene would necessarily give an equimolar mixture of nitrobenzene and nitromethy I benzenes Why or why not ... 

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