Naphthalene mononitro

Tanaka et al. (1996,2000) studied the behavior of a series of naphthalene derivatives in AN solution containing NaN02 and CF3SO3H at 0°C in air. Naphthalene showed very low reactivity, and most of the starting material was recovered after the reaction. In case of 1-methylnaphthalene, a coupling reaction took place to produce 4,4 -dimethyl-l,T-binaphthyl in 91% yield alongside mononitro derivatives of the dimer in 1.5% yield. However, when the reaction is carried out on the same conditions but in inert (Nj) atmosphere, the yield of the dimer decreased from 97 to 15%, and no mononitro derivatives were formed. Therefore, the oxidation of NO with O2 to form NO2 (after the electron transfer to NO from 1-methylnaphthalene) is an obvious step of the reaction depicted in Scheme 4.42. 

In addition to a given explosive compound, we have included references to what may be considered as the parent compound of azido, nitro or nitroso derivatives. This is done because some information concerning the parent is usually needed for the preparation of explosive derivatives. References (mostly Beilstein) to intermediate non-explosive derivatives are included for the same reason. For example, naphthalene and its various mononitro and dinitroderivatives, which are not explosive are listed and references given... 

Aromatic mononitro compounds may sometimes be characterised by conversion into the corresponding dinitro or trinitro derivatives. It may be noted that many poly-nitro compounds form characteristic addition compounds with naphthalene. 

Trinitro to a Mononitro- compounds Naphthalene e- MNN See under parent compds No color No color ... 

Slavinskaya [21] in 1957, found that phenol can be nitrated to o-, p- and 2,4-dinitrophenol using nitric acid dissolved in ethyl nitrate at a concentration as low as 0.5% HN03. Phenetole and naphthalene can also be nitrated with this solution to yield mononitro products. The presence of N02 was essential for successful nitration at such a low concentration of HN03. 

Benzene and naphthalene are nitrated with nitrogen dioxide at 18-20°C to yield mononitro derivatives. At 60°C polynitro compounds are obtained as well. Ultra-violet irradiation does not affect the nitration yield. 

MONONITRO DERIVATIVES OF NAPHTHALENE Both the mononitro isomers, a and p, are known ... 

Composition A mixture consisting of 90 per cent trini-trophenol (picric acid) and 10 per cent mononitro-naphthalene. 

Silica gel supported cerium(IV) ammonium nitrate (CAN) has been employed for controlled nitration of some naphthalene derivatives. While treatment of hydroxynaphthalenes and polynuclear arenes with cerium(IV) ammonium nitrate absorbed on silica gel without a solvent affords mononitro derivatives, the reaction of the same substrates with cerium(IV) ammonium nitrate in solution alfords a considerable per-... 

Naphthalene Series, In the naphthalene series, it is possible to have two different mononitro derivatives, viz., the alpha and beta compounds, also known at l-nitronaphthalene and 2-nitronaphthalene. Upon nitration, the first nitro group enters almost exclusively into the alpha or 1 position a second nitro group enters into position 5 or 8. 

The potential of microreaction processes to influence isomeric product distributions was demonstrated by Loebbecke et cd. [20], They reported on the nitration of naphthalene at moderate temperatures in different types of microreactors to ensure isothermal processing and precise control of residence time (Scheme 4.8). A deliberate synthesis of either mono- or dinitro-substituted naphthalene with high selectivities was achieved, in contrast to a broad product spectrum obtained rmder macroscopic batch conditions. In particular, isomeric ratios of 1- to 2-mononitro-naphthalene and also 1,5- to 1,8-dinitronaphthalene could be significantly increased compared with batch processes. 

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