Picric acid, ammonium salt

SYNS AMMONIUM CARBAZOATE AMMONIUM PICRATE, dry or wetted with <10% water, by weight (UN 0004) (DOT) AMMONIUM PICRATE, wetted with not <10% water, by weight (UN 1310) (DOT) AMMONIUM PICRONITRATE EXPLOSIVE D OBELINE PICRATE PHENOL, 2,4,6-TRINITRO-, AMMONIUM SALT (9CI) PICRATOL PICRIC ACID, AMMONIUM SALT RCRA WASTE NUMBER P009 2,4,6-TRINITROPHENOL AMMONIUM SALT... 

PICRIC ACID, AMMONIUM SALT (131-74-8) Flammable solid. Dry material is a heat-, friction-, and shock-sensitive highexplosive. Dust or powder forms explosive mixture with air. Exploded in elevated temperatures above 250°F/121°C. A powerful oxidizer. Violent reaction with many materials, including reducing agents, combustible materials, fuels, organic substances, sodium nitrite. Contact with most metals, strong bases, concrete, or plaster produces salts that are more heat- and shock-sensitive than the original material. Water increases rate of reactivity with metals. Usually shipped in water solutions up to 90% 10% minimum. Disposal must be handled by explosives experts. 

Ammonium Picrate 2 4,4 - Trinitrophetiol ammonium salt picric acid ammonium salt ammonium picroni-trate ammonium carbazoaie. C4H4N407 mol wt 246.14- C 29.28%, H 2.46%, N 22 76% O 45.50%. Prepn Berl Berl U.S pat. 2,350 322 (1944). Crystal structure Ma.irtmann -Moe Acta. Cryst. 25B, 1452 (1969). 

Ammonium carbazoate Ammonium pioronitrate EINECS 205-038-3 Explosive D HSDB 2070 Obeline picrate Phenol, 2,4,6-trinitro-, ammonium salt Picratol Picric acid, ammonium salt RCRA waste no. P009 2,4,6-Trinitrophenol ammonium salt UN0004 UN1310, Used in expisoives, fireworks and rocket propellants. Crystals d =... 

Picrates, Many aromatic hydrocarbons (and other classes of organic compounds) form molecular compounds with picric acid, for example, naphthalene picrate CioHg.CgH2(N02)30H. Some picrates, e.g., anthracene picrate, are so unstable as to be decomposed by many, particularly hydroxylic, solvents they therefore cannot be easily recrystaUised. Their preparation may be accomplished in such non-hydroxylic solvents as chloroform, benzene or ether. The picrates of hydrocarbons can be readily separated into their constituents by warming with dilute ammonia solution and filtering (if the hydrocarbon is a solid) through a moist filter paper. The filtrate contains the picric acid as the ammonium salt, and the hydrocarbon is left on the filter paper. 

The compound can be prepared from 2,4,6-trinitrophenol (picric acid [88-89-1]) by reduction with sodium hydrosulfide (163), with ammonia —hydrogen sulfide followed by acetic acid neutralization of the ammonium salt (164), with ethanolic hydrazine and copper (165), or electrolyticaHy with vanadium sulfate in alcoholic sulfuric acid (159). Heating 4,6-dinitro-2-benzamidophenol in concentrated HQ. at 140°C also yields picramic acid (166). 

Uninhibited chloroprene suitable for polymerisation must be stored at low temperature (<10° C) under nitrogen if quaUty is to be maintained. Otherwise, dimers or oxidation products are formed and polymerisation activity is unpredictable. Insoluble, autocatalytic "popcorn" polymer can also be formed at ambient or higher temperature without adequate inhibition. For longer term storage, inhibition is required. Phenothiasine [92-84-2] / fZ-butylcatechol [2743-78-17, picric acid [88-89-17, and the ammonium salt of /V-nitroso-/V-pheny1hydroxy1 amine [135-20-6] have been recommended. 

Trinitrophenol (4), commonly known as picric acid (VOD 7350 m/s, d = 1.71 g/cm ), was once used as a military explosive although its highly acidic nature enables it to readily corrode metals. This kind of reaction has led to many fatal accidents, a consequence of some metal picrates being very sensitive primary explosives. The lead salt of picric acid is a dangerous explosive and should be avoided at all cost. In contrast, the ammonium (Explosive D, VOD 7050 m/s, d = 1.60 g/cm ) and guanidine salts of picric acid are unusually insensitive to impact and have been used in armour piercing munitions. 

To achieve the necessary stability he used its ammonium salt, which has no acidic properties instead of picric acid. 

Chloroprene is available commercially on a restricted basis in the United States as crude P-chloroprene with a minimum purity of 95% (Lewis, 1993 DuPont Dow Elastomers, 1997). The principal impurities are dichlorobutene and solvents, with smaller amounts of 1-chlorobutadiene (a-chloroprene), chlorobutenes and dimers of both chloroprene and butadiene. Due to its reactivity, chloroprene is stored at 0°C or below under nitrogen and contains significant quantities of inhibitors, such as phenothiazine, tert-butylcatechol, picric acid and the ammonium salt of A -nitroso-N-phenylhydroxy lamine, to prevent degradation and polymerization (Stewart, 1993). Generally within six weeks of manufacture, crude chloroprene is distilled to produce polymerization grade, which is used within approximately 24 h of distillation. 

Designolle and Brugere suggested that picrate salts could be used as a propellant, while in 1871, Abel proposed the use of ammonium picrate as an explosive. In 1873, Sprengel showed that picric acid could be detonated to an explosion and Turpin, utilizing these results, replaced blackpowder with picric acid for the filling of munition shells. In Russia, Panpushko prepared picric acid in 1894 and soon realized its potential as an explosive. Eventually, picric acid (1,2) was accepted all over the world as the basic explosive for military uses. 

The heavy metal salts of picric acid are dangerously sensitive, and its major use is for the manufacture of ammonium picrate (Explosive D). 

On the whole the properties of trinitro-m-cresol are similar to those of picric acid. The properties of trinitrocresolates differ only slightly from those of picrates, as for example their lead salts. Ammonium trinitrocresolate has been used to some extent in Austria as a high explosive for filling shells. 

When heated with dilute sulphuric acid, hexanitrodiphenylurea is hydrolysed, forming picric acid. With ammonia it produces a deep red colour, which is ascribed to the formation of an ammonium salt of the aci-form. Boiling with aqueous ammonia solution causes hydrolysis with the formation of picramide. 

TPG forms colorless, long, spear like needles with a melting point of 165 Celsius. It can be used as a substitute for picric acid, but readily forms shock sensitive salts with metal hydroxides or carbonates. TPG can be used with satisfactory results when alloyed with RDX, HMX, or PETN for use in blasting compositions. TPG readily forms a triammonium salt when treated with aqueous ammonia. This ammonium salt is used in rocket propellants, fireworks, and pyrotechnic compositions—as it self deflagrates. ... 

Uses Substitute for DNP, and Picric acid in explosives compositions. Readily forms primary explosives when treated with metal hydroxides, or carbonates. The ammonium salt is prepared by treating DNR with aqueous ammonia, and is used in fireworks, and pyrotechnic compositions—as it self deflagrates ... 

Uses Primarily as a substitute for picric acid, DNP, and DNR in explosives compositions for demolition charges. The ammonium salt of methylpicric acid is a primary explosive used in priming compositions, initiation compositions, fireworks, and many pyrotechnic compositions. ... 

Summary Ammonium picramate is the ammonium salt of picramic acid, and is made by reducing picric acid with ammonium bisulfide and ammonia solution. Sulfur is a by-product and must be removed with carbon disulfide. The sulfur/carbon disulfide solution can be distilled to recover the carbon disulfide solvent, and recover the sulfur by-product. The ammonium picramate is recovered by filtration. Commercial Industrial note Part or parts of this laboratory process may be protected by international, and/or commercial/industrial processes. Before using this process to legally manufacture the mentioned explosive, with intent to sell, consult any protected commercial or industrial processes related to, similar to, or additional to, the process discussed in this procedure. This process may be used to legally prepare the mentioned explosive for laboratory, educational, or research purposes. 

Negative substituents enhance the acidic properties of phenols, an effect opposite to that produced with aromatic amines. o and p-Chloro-phenols are considerably stronger acids than phenol itself, and o- and p-nitrophenols are still stronger. Trinitrophenol, picric acid, is a strong acid whose salts are neutral and not decomposed by carbonic acid or by ammonium salts. These salts of picric acid can be salted out of neutral solutions by sodium or potassium chloride. With negatively substituted phenols, it may be possible to separate the phenolate from solutions which are neutral or weakly alkaline to litmus. In doubtful cases, just as with the amines, the precipitated material must be studied to determine whether it is the free phenol or one of its salts. The color of the precipitate gives an indication in the case of the nitrophenols, since the free phenols have only a weak yellow color, whereas the alkali salts are deep yellow. Solubility tests with indififerent solvents may be used in the case of uncolored compounds. Only the free phenol can be separated from acidic solutions. 

This explosive is prepared from in-cresol by a process entirely similar to that by which picric acid is prepared from phenol. The pure material is readily soluble in alcohol, ether, and acetone, soluble in 449 parts of water at 20 and in 123 parts at 100, yellow needles from water, m.p. 107. The ammonium salt, which is sparingly soluble in water, has been used in the composition of certain ammonium nitrate explosives, and it was adopted by the Austrian monarchy under the name of ecrasite as an explosive for shells of large caliber. 

Tri-nitro toluene cannot be exploded by a flame nor by heating in the open, and is only slightly decomposed by striking it a blow. It is best exploded by means of a detonator of fulminate of mercury. It is used for military purposes in shells, bombs and submarine mines. It also forms a constituent of many mixed explosives. It is about 5 per cent less powerful and also less violent and less sensitive than picric acid (p. 630), and does not form sensitive salts or other products under storage conditions as does the latter. A few examples may be given of mixed explosives made with tri-nitro toluene in which ammonium nitrate is used as an oxidizer. The presence of the nitrate weakens the power of the T.N.T , but the mixtures are not very sensitive and are adapted to military purposes and some of them to mine blasting. 

The potassium salt of this acid, which is also known as picro-cyaminic acid, is obtained by treating picric acid with solution of potassium cyanide. The ammonium salt obtained from the potassium salt by double decomposition with ammonium chloride was formerly used in dyeing under the name Grenat soluble. It produces reddish-brown shades on wool and silk, but has now entirely disappeared. 

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