13.8- Trinitro naphthalene

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

Other nitro-derivatives of hydrocarhons and of phenols are used in explosive mixtures. Among the former are dinitro-benzene, chlor-dinitro-benzene, dinitro-toluene, di- or tri-nitro-den-vatives of mesitylene, pseudocumene, and xylene, dinitro-naphthalene. Trinitro-naphthalene and tetra-nitro-naphthalene have also been proposed. Of the nitro-phenols, perhaps the most important is tri-nitro-cresol, known as Cresilite in France, where it is added to Melinite. Other nitro-derivatives of the aromatic series will be mentioned in the section on detonators. 

X,X-Trinitro-1-Methyl naphthalene, mp 180-81°, straw-yellow needles from CC14. V si sol in ale, appreciably sol in CCI4, chlf AcOH. Prepn from 4-nit ro-1-me thy lnaphthalene by nitration with mixed nitric-sulfuric acids Refs 1) Beil 5, (266) 2) R. Lesser A. 

K chlorate and aromatic hydrocarbons (such as naphthalene), and not more than 12% nitro-hydrocarbons (but no trinitro compds), the remainder consisting of paraffins, fatty oils, flour or other combustibles. It might also contain not more than 4% blasting gelatin. The prefixes Gesteins- and Wetter- were applied if the expls were intended for rock or coal mine use Ref Marshall, Diet (1920), 65... 

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

Dinitro-1 -Naphthol (4,6-Dinitro-1 -oxy-naphthalene). Crysts from methanol (as Na salt), mp 240°. Sol in chlf. Prepn from 1,4,6-trinitro-2-naphthylamine by diazotization in AcOH-sulfuric acid to yield 4j6-dinitro-2-diazo-... 

Trinitro-1-Naphthol (2,4,5-Trinitro-1-hydroxy naphthalene). Yellow leaflets or prisms mp 189—90° bp, explds. Sol in hot AcOH, si sol in hot w, ale, benz, eth acetate, xylene cold AcOH. Prepn from 2,4-dinitro-naphthol by nitration, or from 4-chlor-1,3,8-trinitronaphthalene by heating with 0.1 N NaOH in w or ale... 

Tri nitro-1 -N aphthol (2,4,7 -Trinitro-1 -oxy-naphthalene). Yellow prisms from AcOH or benz, mp 145° (decompn). Sol in AcOH glac AcOH. Prepn from 2,4-dinitro-l-naphthol by mixed acid (nitric-sulfuric-acetic) nitration. The compound is extracted as the Na salt from... 

Trinitro-1-Naphthol (2,4,8-Trinitro-l-oxy-naphthalene). Yellow prisms, mp 175°. Sol in cold w. Prepn from 8-nitro-naphthoquinone-(l,4)-oxime by heating with dU nitric acid Ref Beil6, 620 (309)... 

Trinitro-5-hydroxy-l-acetoxy-naphthalene, acetic acid-[2,6,8-trinitro-5-hydroxy-1 -naphthyl-ester], [2,6,8-trinitro-5-hyd roxy-1 -naphthyl] -acetate). (O2N)3C10H3(OCOCH3).OH, mw 337.22, N 12.46%, OB to C02 -87.78%, yellow needles... 

Trinitro-3-chlor-l-oxy-naphthalene, X,X,X-trinitro-4-chlor-2-oxy-naphthalene). (O2N)3C10H3C1.0H, mw 313.62, N 13.40%, OB to C02 -76.53% crysts from AcOH with 1 mol AcOH as yellow-blue needles, mp M56°... 

Trinitro-2-Naphthol (1,6,8-Trinitro-2-hydioxy naphthalene). Light yellow crysts, mp 221 Prepn from 7-chIor-l,3,8-trinitro-naphthalene by treating with NaOH soln in the presence of acet. Explds on heating Refs 1) Beil 6, (610) 2) E.J. van der... 

X,4,6-Trinitro-2-Naphthol (X, 4,6-Trinitro- 2-oxy-naphthalene). Yellow needles from ale, mp 150° (decompn). Prepn from 4,6-dibromo-2-naphthol by nitration with nitrous-nitric acid. Rapid decompn occurs above 159°... 

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. ... 

Ref 4). Was first prepd by Staedel(Ref 2) by heating the ethyl ether of 2,4,5 trinitro-o-naphthylamine with ale NHS in a sealed cube at 50° for 2 hours. A simpler method is to pass NHS gas through an amyl alcohol soln of 4 chloro-l,3,8 trinitro-naphthalene (Ref 3). Other methods are described in Ref 4... 

Mesitylene, Trinitro (2,4,l -TNMes) Mo no nitrocompounds Naphthalene Pink No color See under parent compds ... 

Aromatic mononitro compounds may sometimes be characterised by conversion into the corresponding dinitro or trinitro derivatives. It may be noted that many poly-nitro compounds form characteristic addition compounds with naphthalene. 

Trinitro to a Mononitro- compounds Naphthalene e- MNN See under parent compds No color No color ... 

Trinitrocresol + Naphthalene, C H N O+C, H lt-yel ndls (from acet), mp 125-27° decompd by w, diffc sol in acet (Ref 1, p 387). A similar salt is formed from Trinitro-o-cresol naphthalene (Ref 4)... 

Davis and his co-workers [127,128] found chlorobenzene also undergoes oxynitration by action of 65% nitric acid, with formation of trinitro-m-chlorophenol along with chlo-ronitrobenzenes, while naphthalene when nitrated with more dilute acid, for example, at a concentration of 65%, yielded 2,4-dinitro-a-naphthol besides 2-nitro-a-naphthol. 

According to Jeffemov and Tikhomirova [10], 2,4,6-trinitro-m-xylene contrary to both sym-trinitrobenzene and 2,4,6-trinitrotoluene does not combine with such hydrocarbons as acenaphthene, anthracene, phenanthrene, fluorene or naphthalene. 

The conversion of dinitro- into trinitro-naphthalene may be achieved by using nitrating mixtures of varying compositions ... 

Resinous amorphous, brown substances are also formed, and found in dinitro-and trinitro-naphthalenes. They are partly soluble in alkalis, hence the suggestion that they are of an acidic or phenolic character and come from products of oxidation of naphthalene. 

The presence of nitro groups enhances the acidic properties of the phenol group. This is why the trinitro derivatives are also called acids, e.g. trinitrophenol is known as picric acid and trinitroresorcinol as styphnic acid. These compounds readily form salts with metals or bases. Polynitro derivatives of phenols also form addition compounds with hydrocarbons, e.g. naphthalene. 

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