2.4.6- Trinitroresorcinol

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

Benzo[ghi]perylene (1,12-benzoperylene) [191-24-2] M 276,3, m 273°, 277-278.5°, 278-280°, Purified as light green crystals by recrystn from CfiH6 or xylene and sublimes at 320-340° and 0.05mm [UV Helv Chim Acta 42 2315 7959 Chem Ber 65 846 1932 Fluoresc. Spectrum J Chem Soc 3875 7954]. 1,3,5-Trinitrobenzene complex m 310-313° (deep red crystals from C6Hg) picrate m 267-270° (dark red crystals from CgH6) styphnate (2,4,6-trinitroresorcinol complex) m 234° (wine red crystals from CgH6). It recrystallises from propan-l-ol [J Chem Soc 466 7959]. 

Trinitroresorcinol 6% 2) PbDNAzP 15, Ba nitrate 25, Pb dioxide 12, Diazodinitrophenol 17, Trinitroresorcinol 8, ground glass 22, gum arabic 1%... 

This compound has the formula (NO CgHOjPb, but usually contains also one molecule of water as water of crystallisation. Trinitroresorcinol is manufactured by the nitration of resorcinol and is then usually converted to the magnesium salt, which is reacted with lead nitrate solution under warm conditions and with good stirring. The product is precipitated as a red crystalline material which can be washed by decantation and separated by filtration. 

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. 

Toluenesulfonic acid, 2808 Trichloroacetic acid, 0658 Trifluoroacetic acid, 0665 Trifluoromethanesulfonic acid, 0375 Trinitroresorcinol, 2119... 

Picric acid (trinitrophenol) and trinitroresorcinol, when added to fixative solutions, give greater fine structural preservation of cells (11,12). These compounds cause coagulation of proteins by forming salts with positively charged groups of proteins (11). The protein precipitates that form retain their antigenicity (3). Picric acid or trinitroresorcinol are most often added to formalde-... 

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. ... 

Primer compn for small arms ammo Tri-nitroresorcinol 15, Pb thiocyanate 20, K chlorate 50 Pb styphnate 15%) Ibid, USP 1416122(1922) (Similar to above but Di-plumbic di-trinitroresorcinol is used instead of Trinitroresorcinol) Ibid, USP 1416123 (1922) (Similar to above except that MF is used in lieu of Pb nitroresorcinol compds)... 

Dinitro-p-cresol 2,4,6-rTrinitroaniline (Picramide) sym-Trinitromesytylene (1,3,5-Triraethyl-2,4,6-trinitrobenzene) 2,4,6-Trinitroresorcinol (Styphnic Acid) 2-Amino-... 

Trinitroresorcinol or Styphnic acid, dry or wetted with less than 20 per cent water, or mixtute of alcohol and water, by mass 0219... 

The presence of nitro groups in phenol and resorcinol enhances their acidic properties and that is why trinitrophenol is commonly known as picric acid while trinitroresorcinol is known as styphnic acid. 

In the method employed at Wolfratshausen [31] a solution of magnesium styphnate was first prepared, adding to 20 kg of magnesium oxide a suspension (partly solution) of 120 kg of trinitroresorcinol in 350 1. of water. The temperature rose... 

For this production, the starting materials are needed trinitroresorcinol and magnesium oxide to form magnesium styphnate and lead nitrate, all disssolved in distilled water. 

Yefremov et al. [27, 28] (systems containing TNT, picric acid, trinitrocresol, trinitroresorcinol, tetryl, trinitroxylene etc.) Wogrinzand Vari [29] (systems containing TNT and picric acid) C. A. Taylor and Rinkenbach [30] (systems containing TNT, picric acid and tetryl) Jovinet [31] (the system picric acid-nitronaphthalene) Hrynakowski and Kapuscinski [32] (systems containing TNT and picric acid) T. Urbanski and Kwiatkowski [33] (systems containing picric acid and dinitro-naphthalenes). 

Trinitro-1,3-dihydroxy benzene 2,4,6-Trinitroresorcinol or STYPHNIC ACID... 

Trinitroresorcinol-dimethylether, almost col pltlts (from ale) or It-yel ndls (from ale), mp 124—25° sol in ale 81 eth prepd by nitrating 2,4-dinitro- 4,6-dinitro-resorcinol-dimethylether with HNOa coned H2S04 in the cold (Ref 7)... 

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