9 4,6-Dinitroresorcinol

The sulfonation-nitration strategy also provides a route to styphnic acid (5) (2,4,6-trinitroresorcinol) from resorcinol (22) but the control of temperature in this reaction is very important. The synthesis of styphnic acid (5) from the nitration of 2,4-dinitroresorcinol (24) with mixed acid or concentrated nitric acid is a higher yielding route. 2,4-Dinitroresorcinol (24) is conveniently prepared from the nitrosation of resorcinol (22) followed by oxidation of the resulting 2,4-dinitrosoresorcinol (23) with dilute nitric acid. 2,4-Dinitrosoresorcinol (23) also generates styphnic acid (5) on treatment with concentrated nitric acid. ... 

Resorcinol (22) is readily converted to 2,4-dinitrosoresorcinol (23) in quantitative yield by slowly adding an aqueous solution containing two mole equivalents of sodium nitrite to a solution of resorcinol that has been acidified with two mole equivalents of sulfuric acid. The 2,4-dinitrosresorcinol (23) from this process can be oxidized to 2,4-dinitroresorcinol (24) with a binary phase system of toluene and dilute nitric acid at -5 Treatment of either 2,4-... 

Both 2,4-dinitrosoresorcinol (23) and 2,4-dinitroresorcinol (24) are important in the explosives industry. The lead salt of 2,4-dinitrosoresorcinol has a low ignition temperature and finds use in priming compositions and in electrical igniters. The lead salt of 2,4-dinitroresorcinol is a weak initiator but is found to exhibit high sensitivity to friction and stab action without being highly sensitive to impact, and as such, this compound has found use in primers. 

Ad 86) S. Nauckhoff, Explosivst 1953, 29-34 (Investigation of process of combustion of fuses) Ad 87) L. Rubenstein, USP 2653863(1953) CA 48, 2376(1954) [initiating compn was prepd by simultaneous adding at a constant rate over 9 mins, two 125-ml solns to 800-ml of 0. 02 % aqueous dextrin soln while the temp was maintained at 70°. The 1st soln consisted of 7.8 g of Na azide 3g of 2,4-dinitroresorcinol that had been treated with aq soln of 1.12 g NaOH ... 

Dinitroresorcinol proved to be an important constituent of these mixtures as an sensitizing agent i.e. facilitating uniform burning under low pressure. 

Dinitroresorcinol forms several salts, some of them explosive, as for example Potassium 2.4-Dinitroresorcinate, when obtd in anhydrous state, KCgHj Og, dk-red crysts, explodes on heating, while its monohydrate, yel ndls (from w) is not explosive Lead 2,4-Dinitroresorcinate, abbreviated as... 

Incorrectly lists Styphnic Acid as 2,4-Dinitroresorcinol) 16) B.F. Husten,... 

N 14.12% yel scales(from ale), crysts (from MeOH) readily sol in ale, acet, benz or MeOH insol in w or petr eth was prepd by treating either l-chloro-2,4-dinitroresorcinol dimethyl-ether or l-chloro-4, 6-dinitroresorcinol dimethyl ether with cold HNOa or with mixed HN03-H2S04 acid(Refs 1,2 3). Its expl props were not detd Refs l)Beil 6 [826] 2)H.H.Schlubach ... 

Resorcin, 2,4-Dinitroso (Ger) (2,4-Dinitroso-l,3-dihy droxybenzene or 2,4-Dinitroresorcinol, which rearranges to the tautomeric form, Ie, Cyclo-hexene-(l)-tetron-(3,4,5,6)-dioxime-(3,5) Cyclo-hexene 1 )-dion-(4,6)-dioxime-(3,5)- or Dichin-oyl-dioxime)... 

S.W. Wilson, JRNBS 52, 195-99(1954) CA 48, 11061(1954)(A photoelectric colorimeter for measuring the chromaticities of pyrotechnic smokes) 20)Snell Snell 4(1954) [Colorimetric tests of various org compds including many expls and their primary materials, such as CarbazoIe(pp 314-15) Chloro-2,4-dinitrobenzene (p 17) 2,4-Dinittoanisole(p 19) Dinitrobenzene (p 16) Dinitrocresol(p 19) Dinitronaphthalene (p 19) Dinitrophenol(p 13) 2,4-Dinitroresorcinol (p 13) 2,4-Dinitrotoluene(p 18) Dinitroxylene ... 

Gallic acid resorcinol 2,4-dinitroresorcinol 2-amino-4-nitrophenol Competitive inhibitors [77]... 

Incorrectly lists Styphnic Acid as 2,4-Dinitroresorcinol) I6) B.F. Husten, "Basic Lead Styphnate, Fine Milling of , NAVORD OD 23996 (March 1963) 17) S.J. 

A semi-industrial method of making 2.4-dinitroresorcinol was given by [Rcheroulle and Soule 133]. It consists of two stages ... 

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