Styphnic acid

Unlike aliphatic hydrocarbons, aromatic hydrocarbons can be sul-phonated and nitrated they also form characteristic molecular compounds with picric acid, styphnic acid and 1 3 5-trinitrobenzene. Many of the reactions of aromatic hydrocarbons will be evident from the following discussion of crystalline derivatives suitable for their characterisation. 

Styphnates. Aromatic hydrocarbons (and also some amines and heterocyclic bases) form 1 1-addition products with styphnic acid (2 4 6-trinitroresorcinol),... 

Dissolve equimolecular amounts of the hydrocarbon and styphnic acid in the minimum volume of hot acetic acid and allow to cool. Filter oflf the crystalline derivative which separates, wash it with a little acetic acid and dry in the air. Determine the m.p. Recrystallise from acetic acid and again determine the m.p. 

Styphnic acid is a nitrogen compound. Lead styphnate monohydrate was found to detonate at 229°C (444°F), but the course of decomposition could be followed at 228°C and below. 

Magnesium Triniiroresorcinate. See under Styphnic Acid and Styphnates... 

Heat of fusion. The Qfusi0n °f mixts of MEDINA with PETN, HMX, TNT, RDX, BTNEU, EDNA, Styphnic Acid, PA, Tetryl are given in Ref 13, p 9 ... 

Picric Acid compared with Trinitrobenzene is probably the result of the former s greater ability to detonate. The ease of detonation of Picric and Styphnic acids as compared with Trinitrobenzene is well known. D. Smolefiski and W. Czuba (Ref 8) recently pointed out that Dinitrophenol detonates more readily than Di-nitrobenzene... 

Numerous molecular compds of phenanthrene and its derivatives have been reported with perchloric acid, PA, styphnic acid, sym-TNT, sym-TNB, and Tetryl. These compds are useful for identification purposes because many have sharp melting points but none have been reported to be expl... 

It was prepd in 1884 by Nolting and Collin (Ref 2) from ethyl- or methyl-esters of Styphnic Acid and ale ammonia. Blanksma (Ref 3) prepd it from 3-chlor-2,4,6-trinitroanisole (or 3-chlbr-2,4,6-trinit,rophetietole) and ale ammonia, Kbrner and Contardi ( Ref 4) from 2,4-dibrom- (or dichlor)- 3,5-trinitrobenzene and ale ammonia, and Fliirscheim (Ref 5) from tetranitro-aniline and ammonia... 

The reaction conditions necessary to obtain a good yield of the title compound (a difficult isomer), and to avoid hazards during the nitration of resorcinol, are critical and strict adherence to those specified is essential. The necessary 80% white fuming nitric acid must be completely free from oxides of nitrogen and nitrous acid, and procedures for this are detailed. Then the temperature dining addition of the diacetate must be kept between -10 and 0°C by regulating the rate of addition. The alternative use of 80% sulfuric acid as solvent for the 80% nitric acid (5 equiv.) is preferred as more reliable, but both methods have led to violent exothermic decomposition, accompanied by fume-off, after an induction period. In any event, the explosive 2,4,6-trinitroresorcinol ( styphnic acid ) is produced as a by-product. 

Trinitroresorcinol (5) (styphnic acid) has also seen limited use as an explosive because of its acidic properties and the relatively high cost of resorcinol. However, the lead salt of styphnic acid has found use as a primary explosive in detonators and primers. 

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. ... 

Warman and Siele reported a high yielding route to l,3-dichloro-2,4,6-trinitrobenzene (106) (styphnyl chloride) which involves treating styphnic acid (5) with two equivalents of pyridine followed by reacting the resulting pyridinium salt (133) with phosphorous oxychloride. l,3-Dichloro-2,4,6-trinitrobenzene is an important precursor to the thermally stable explosive DATE (Section 4.8.1.4). 

Hexamethylenetetramine Styphnate or Hexamine Styphnate. Probably C12H15N 08 (struct formula unknown) mw 385.34, N 25.45% crysts [from NM], mp 197-198° by fast heating Richmond et al (Ref 2) prepd it by adding one equivalent of hexamine to a satd aq soln of Styphnic Acid. The pptn of hexamine mono-styphnate was quantitative if the Styphnic Acid was saturated into ethanol instead of water, the loss by solubility in 1 1 water-ethanol was only 0.25 g per 10Q cc of soln. 

Acido stifnico o Trinitroresorcina (Styphnic Acid, abbrd as StA), (HO)2C6H(N02)3. It is described in Ref 31, pp 453 to 455 and in Ref 28, p 318. Used in the form of its lead salt Stifmto di piombo (qv), meaning Lead Styphnate, abbrd LSt... 

Strontium carbonate Strontium nitrate Strontium oxalate Styphnic acid Styphnic acid Sub-VX... 

Styphnic acid. Ammonia, Barium chlorate dehydrate. Acetone Benzyl chloride. Sodium cyanide. Ethyl alcohol. Liquid hromine, Carhon tetrachloride. Sodium hydroxide. Sodium sulfate. Chloroform... 

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