Trinitro m-cresol

Cresol for nitration should contain a high proportion of the m- isomer. Commercial meta-cresol usually contains about 60% of the m- isomer and 40% of p- cresol. The preparation of a much more costly raw material, containing 90% of m- cresol is also possible. It is clear that the yield of trinitro-m-cresol will correspond to the m- cresol content in the starting product. 

A methyl group present in the ring facilitates the introduction of nitro groups. This is why m- cresol is more readily nitrated than phenol. On the other hand a methyl group enhances oxidation processes. This accounts for the lower yield of trinitro-cresol obtained, as compared with that of picric acid. Like picric acid, trinitrocresol has the disadvantage of readily forming metallic salts which are sensitive to impact. 

All these factors have limited the practical application of trinitrocresol. France was the only country which used it, under the name of Cresilite mostly in mixtures with other nitro compounds to lower their melting points (Vol. III). Among nitro derivatives of cresols, dinitro-m-cresol (m. p. 86.5°C) 

6- Trinitro-m-cresol (m. p. 107-107.5°C) is less soluble in water than picric acid. With 100 g of water the following quantities go into solution  

Benzene dissolves 2,4,6-trinitro-m-cresol more readily than picric acid  

---

Other examples of oxynitration include the formation of (1) 2,4,6-trinitro-m-cresol from toluene, (2) 2,4-dinitronaphth-l-ol from naphthalene, (3) 3-chloro-2,4,6-trinitrophenol from chlorobenzene and (4) 3-hydroxy-2,4,6-trinitrobenzoic acid from benzoic acid. ... 

Accdg to Chalon (Ref 2), as quoted by Marshall (Ref 3) and Davis (Ref 8), Ecrasite was Ammonium Trinitrocresylate, prepd by treating 2,4,6-Trinitro-m-cresol with ammonia... 

For ready reference we also include a table of standard heats (enthalpies), entropies and heats of formation of a variety of explosives. This table is taken from Ref 24. All values are in KJoules. To obtain the more commonly used Kcals, divide by 4.184. TNX is 2,4,6-Trinitro-m-xylene TNM (in this table only) stands for 2,4,6-Trinitromesitylene, and TNC is 2,4,6-Trinitro-m-cresol... 

Some of its salts are expl, for example, that of 2,4,6-trinitro-m-cresol, explg ca 477°(Ref 2)... 

Formyl peroxide Nitrocellulose, dry Trinitrochlorbenzene 2, 4, 6 trinitro-m- cresol... 

Trinitro-m-cresol forms addition compounds with aromatic hydrocarbons in the molecular proportion of 1 1 ... 

---