테트라 니트로메탄 C화학적 특성, 용도, 생산
개요
Tetranitromethane (TNM) is a nitroalkane compound that is
a colorless to pale-yellow liquid or solid (below 57 F) with
a biting, pungent odor at room temperature. TNM is not
known to occur as a natural product and is generated during
the manufacture of trinitrotoluene (TNT) as an undesired byproduct
that can be separated by means of its higher vapor
pressure. It can be prepared by different reactions, the nitration
of acetic anhydride or acetylene with nitric acid being the less
problematic. It was synthesized in large amounts (as an
industrial-scale production) for the first time in Germany
during World War II during the development of the V2 rocket
for use as a substitute for nitric acid in rocket fuel and due to the
observation that its addition to diesel fuel increased the cetane
number. A pilot-scale manufacture was set up by Nitroform
Inc. (Newark, NJ, USA), but in 1953 was destroyed by an
explosion. In 1994, TNM was produced by only one company
in the United States and another one in Russia.
화학적 성질
Tetranitromethane, a nitroparaffin, is a colorless to pale yellow liquid or solid with a pungent odor. It causes tears.
물리적 성질
Colorless to pale yellow to yellow-orange liquid with a pungent odor. Sensitive to heat, friction,
and shock. Explosive in presence of impurities.
용도
Reagent for nitration of enol silyl ethers7 and aromatic compounds.8 Employed in the photooxidation of sulfides to sulfoxides.9
일반 설명
A pale yellow liquid. Irritates skin and respiratory tract. Very toxic by inhalation. Difficult to ignite. Burns at a steady rate once ignited. Under prolonged exposure to fire or heat containers may rupture violently and rocket Produces toxic oxides of nitrogen during combustion.
공기와 물의 반응
Highly Flammable. Insoluble in water.
반응 프로필
Self-reactive. TETRANITROMETHANE is a weak, but highly sensitive explosive [Van Dolah 1967]. May decompose explosively if contaminated with combustible material. A propellant. Ignites upon contact with alcohols, amines, ammonia, beryllium alkyls, boranes, dicyanogen, hydrazines, hydrocarbons, hydrogen, nitroalkanes, powdered metals, silanes, or thiols [Bretherick 1979 p.174].
위험도
Dangerous fire and explosion risk. Toxic
by ingestion, inhalation, skin absorption. Eye and
upper respiratory tract irritant. Upper respiratory
tract cancer. Possible carcinogen.
건강위험
Acute effects include irritation of the eyes and respiratory passages and mild burns to the skin. After more prolonged inhalation, headache and respiratory distress may occur. After prolonged exposure, central nervous system, heart, liver, and kidney damage can occur as well as pulmonary edema.
화재위험
Spontaneous chemical reaction may produce fire. Material is a strong oxidizer. The potential for explosion is severe, especially when exposed to heat or to powerful oxidizing or reducing agents; or when shocked or heated. TETRANITROMETHANE is more easily detonated than TNT. Impurities can also cause explosion. The material is highly sensitive; hydrocarbons exposed to TETRANITROMETHANE form exceedingly sensitive explosives. When heated to decomposition, TETRANITROMETHANE emits highly toxic fumes of oxides of nitrogen. Shock will explode it. Avoid hydrocarbons, aluminum, toluene, cotton, aromatic nitro compounds, alkalis, metals and rubber. Avoid impurities, shock, heat, and reducing agents.
Safety Profile
Confirmed carcinogen with carcinogenic and neoplastigenic data. Poison by ingestion, inhalation, intravenous, and intraperitoneal routes. Irritating to the skin, eyes, mucous membranes, and respiratory passages, and does serious damage to the liver. Mutation data reported. It occurs as an impurity in crude TNT, and is thought to be mainly responsible for the irritating properties of that material. It can cause pulmonary edema, mild methemoglobinemia, and fatty degeneration of the liver and hdneys. A powerful oxidizer. A very dangerous fire hazard. A severe explosion hazard when shocked or exposed to heat. May explode during distillation. Potentially explosive reaction with ferrocene, pyridine, sodium ethoxide. mxtures with amines (e.g., aniline) ignite spontaneously and may explode. Mixtures with cotton or toluene may explode when ignited. Forms sensitive and powerful explosive mixtures with nitrobenzene, l-nitrotoluene, 4-nitrotoluene, 1,3-dinitrobenzene, 1 -nitronaphthalene, other oxygen-deficient explosives, hydrocarbons. Can react vigorously with oxidizing materials. Incompatible with aluminum. When heated to decomposition it emits highly toxic fumes of NOx. Used as an oxidizer in rocket propellants and as an explosive. See also NITRATES; EXPLOSIVES, HIGH.
잠재적 노출
Tetranitromethane is used as a solvent for polymers and as a stabilizer; as an oxidizer in rocket propellant combinations. It is also used as an explosive in admixture with toluene.
Carcinogenicity
Tetranitromethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
운송 방법
UN1510 Tetranitromethane, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 5.1-Oxidizer, Inhalation Hazard Zone B.
Purification Methods
Shake tetranitromethane with dilute NaOH, wash, steam distil, dry with Na2SO4 and fractionally crystallise it by partial freezing. The melted crystals are dried with MgSO4 and fractionally distilled under reduced pressure. Alternatively, shake it with a large volume of dilute NaOH until no absorption attributable to the aci-nitro anion (from monodiand trinitromethanes) is observable in the water. Then wash it with distilled water, and distil it at room temperature by passing a stream of air or nitrogen through the liquid and condensing it in a trap at -80o. It can be dried with MgSO4 or Na2SO4, fractionally crystallised from the melt, and fractionally distilled under reduced pressure. [Liang Org Synth Coll Vol III 803 1955, Beilstein 4 H 80, 4 I 21, 4 II 45, 4 III 116, 4 IV 107.] Potentially explosive (when impure e.g. with toluene), toxic, carcinogenic.
비 호환성
Tetranitromethane is a powerful oxidizer. It is more easily detonated than TNT. Contact with hydrocarbons, alkalis, or metals form explosive mixtures. Contact with toluene or cotton may cause fire andexplosion. Combustible material wet with tetranitromethane may be highly explosive. The potential for explosion is severe, especially when exposed to heat, powerful oxidizers, or reducing agents; or, when subject to mild shock. Impurities can also cause explosives. Attacks some plastics, rubber and coatings.
폐기물 처리
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Open burning at remote burning sites is not entirely satisfactory since it makes no provision for the control of the toxic effluents, nitrogen oxides and HCN. Suggested procedures are to employ modified closed pit burning, using blowers for air supply and passing the effluent combustion gases through wet scrubbers.
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