Phenol, 2,4,6-Trinitro

Trinitrophenol. See Phenol, Trinitro. Trinitrophenol, Ammonium Salt. See Explosive D... 

Mixture in Equimolecular Proportions of— Trinitro-phenol Nitro-naphthalene -Trinitro-phenol Dinitro-toluene Trinitro-phenol Trinitro-cresol... 

It is also to he noted that ortho and para substitution often occur together in the same molecule, so that the group R enters the para and also both the ortho positions thus both aniline and phenol on bromination readily give symmetric (2,4,6) tribromo-compounds (p. 165), while both toluene and phenol on nitration readily give the symmetric trinitro-derivatives (p. 170). 

Picric acid, the 2 4 6-trinitro derivative of phenol, cannot be prepared in good yield by the action of nitric acid upon phenol since much of the latter is destroyed by oxidation and resinous products are also formed. It is more convenient to heat the phenol with concentrated sulphuric acid whereby a mixture of o- and p-phenolsulphonic acids is obtained upon treatment of the mixture with concentrated nitric acid, nitration occurs at the two positicsis mela to the —SOjH group in each compound, and finally, since sulphonation is reversible, the acid groups are replaced by a third iiitro group yielding picric acid in both cases ... 

Trinitro Phenol + 1-Naphthol (Picric Acid + 1 -oxy-naphthalene). 

Sowinski M. Warman, Lead Salts of Trinitro Phenols. I. Preparation and Properties of Methoxy Picric Acid and Lead Methoxy Picrate , PATR 3344(1966)... 

Most of the chemistry of PA is determined by its acidic nature. It is a strong acid whose ionization constant of 1.6 x 10"1 (Ref 31) makes it comparable in acid strength to pyrophosphoric acid and trichloroacetic acid. PA readily forms salts with bases and esters with alcohols. The salts are known as Picrates. Many of them are expl and will be described in a separate article in this Vol. The esters are phenol ethers, eg, Trinitro-anisolc (see Vol t, A450-L)... 

Ebert S, P-G Rieger, H-J Knackmuss (1999) Function of coenzyme P420 in aerobic catabolism of 2,4,6-trinitro-phenol and 2,4-dinitrophenol by Nocardiodes simplex FJ2-1 A. J Bacterial 181 2669-2674. 

The crude product contains isomers other than that required and also nitrated phenolic compounds resulting from side reactions. The usual method of purification is to treat the crude product with sodium sulphite, which converts asymmetric trinitro compounds to sulphonic acid derivatives, and to wash out the resulting soluble products with alkaline water. The purity of the product is determined by the melting point, the minimum value for Grade I TNT commonly being 80-2°C. Unless adequate purity is achieved, slow exudation of impurities can occur during storage and the TNT then becomes insensitive. 

This salt of the mono-aci />-quinonoid form of 3-hydroxymercurio-2,4,6-trinitro-phenol explodes on rapid heating. 

Some complications arise from the presence of proton donor-acceptor interactions134 when the donor is a protic amine. The separate evaluation of the two kinds of interactions may be a difficult problem. Similarly, if the electron acceptor is also a proton donor, the overlapping of salification and complexation processes makes the separate investigation of the interactions very difficult. This is the case in the complexes between amines and picric acid or other related phenols. For complexes of 2,4,6-trinitro-3-hydroxypyridine135 and... 

Substituierte Phenole reagieren mit Stickstoffdioxid in Benzol zu Alkyl-substituierten 6-Oxo-3,4,5-trinitro-cyclohexenen3 z.B. ... 

Trinitro-lead-phenolate Sodium 2-amino-4,6-dinitrophenolate Sodium 2-amino-4,6-dinitropicrate Lead picrate... 

Explosif MDFC. Fr HE contg PA 55, Dinitro-phenol 35 fit Trinitro-m-cresol 10%. Its low mp (80—90° ) permitted its use for cast-loading projectiles Ref Davis (1943), p 166—67... 

Picric acid Dinitro- phenol TNT Trinitro- cresol Nitro- naphtha- lene Dinitro- naphtha- lene... 

CH— C( N2)—CjO mw 226.11, N 24.78% golden-yel pits, mp - very expl was prepd by dissolving 2,3,6-trinitro-4-diazo-phenol in boiling Na acetate and redissolving the Na salt in a large quantity of hot w acidified with HC1 (Refs 2 3)... 

Trinitro-3,5-dichlorophenol (called 3.5-Dichlor-2.4.6-trinitro-phenol or Dichlorpikrin-saure in Ger),... 

Accdg to Urbanski (Ref 6, p 537), 2,4-DNR cannot be prepd by the conventional method for phenols (ie sulfonation of resorcinol followed by the action of nitric acid), because this method yields the trinitro compd. There are, however, two methods of prepn possible ... 

Crude TNT contains isomers and nitrated phenolic compounds resulting from side reactions. The usual method of purification is to treat crude TNT with 4% sodium sulfite solution at pH 8-9, which converts the unsymmetrical trinitro compounds to sulfonic acid derivatives. These by-products are then removed by washing with an alkaline solution. Pure TNT is then washed with hot water, flaked and packed. It is important to remove the waste acid and unsymmetrical trinitrotoluenes together with any by-products of nitration as they will degrade the TNT, reduce its shelf life, increase its sensitivity and reduce its compatibility with metals and other materials. Trace amounts of unsymmetrical trinitrotoluenes and by-products will also lower the melting point of TNT. TNT can be further recrystallized from organic solvents or 62% nitric acid. 

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