Nitromethan Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE, VISKOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft und können sich am Boden ausbreiten. Fernzündung möglich.
CHEMISCHE GEFAHREN
Bei Stoß, Reibung oder Erschütterung explosionsartige Zersetzung möglich. Kann beim Erhitzen explodieren. Zersetzung beim Verbrennen unter Bildung von Stickstoffoxiden. Reagiert mit Alkalien. Reagiert sehr heftig mit starken Oxidationsmitteln und starken reduzierenden Stoffen unter Feuer- und Explosionsgefahr. Bildet mit Aminen ein schlagempfindliches Gemisch.
ARBEITSPLATZGRENZWERTE
TLV: 20 ppm (als TWA); Krebskategorie A3 (bestätigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); (ACGIH 2005).
MAK: Hautresorption; Krebserzeugend Kategorie 3B; (DFG 2006).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen, die Haut und die Atemwege. Möglich sind Auswirkungen auf das Zentralnervensystem mit nachfolgender Depression des Zentralnervensystems.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann Dermatitis hervorrufen. Möglich sind Auswirkungen auf das periphere Nervensystem, Nieren und Leber mit nachfolgenden Funktionsstörungen.
LECKAGE
Gefahrenbereich verlassen! Fachmann zu Rate ziehen! Zündquellen entfernen. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT mit Sägemehl oder anderen brennbaren Absorptionsmitteln binden. Persönliche Schutzausrüstung: Atemschutzgerät, A/P2-Filter für organische Dämpfe und schädlichen Staub.
R-Sätze Betriebsanweisung:
R5:Beim Erwärmen explosionsfähig.
R10:Entzündlich.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S41:Explosions- und Brandgase nicht einatmen.
Aussehen Eigenschaften
CH3NO2. Farblose, viskose Flüssigkeit mit stechendem, obstartigem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken. Dämpfe wirken auf das ZNS. Schädigt Leber und Nieren.
Entzündlich. Nicht über 50鳦 erwärmen. Nicht mit Alkalihydroxiden, Säuren und Aminen in Berührung bringen.
LD
50 (oral, Ratte): 940 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Persönliche Maßnahmen: Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Pulver, Schaum.
Ungeeignete Löschmittel: Wasser.
Mit Luft Bildung explosionsfähiger Gemische. Dämpfe schwerer als Luft. Schlag und Reibung vermeiden. Im Brandfall können nitrose Gase entstehen.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Nitromethane (75-52-5) is an explosive material that was
originally manufactured for various applications including
mining, construction, demolition, law enforcement, and
military uses. However, due to threats of terrorism and
increased attention to accident prevention, regulations concerning
the transportation, storage, use, and transfer relating to
explosives have steadily increased over the last few years and
manufacturing limited.
Chemische Eigenschaften
Nitromethane is a highly flammable and explosive colorless liquid with a strong, disagreeable odor. Nitromethane is not explosive, but is used as industrial chemical for various purposes. Nitromethane can explode only in big quantity and in strong confinement. In combination with some further components, nitromethane is the important part of very strong, cap sensitive explosives. Therefore, nitromethane is an easy accessible precursor for preparation of strong home-made explosives.
Nitromethane is used as a stabilizer of halogenated organic solvents, rocket and racing fuel and a chemical intermediate. It is also used as a solvent for cyanoacrylate adhesives, polymers and waxes. It serves as a Michael donor, adding to alfa,beta-unsaturated carbonyl compounds through 1,4-addition in the Michael reaction. It acts as a solvent used for extractions, reaction medium and as a cleaning solvent. Further, it is used in the manufacture of pharmaceuticals, explosives, fibers and coatings.
Physikalische Eigenschaften
Colorless liquid with a strong, disagreeable odor. Odor threshold concentration is 3.5 ppm
(quoted, Amoore and Hautala, 1983).
Verwenden
Most of the nitromethane produced in the United States (85% to 90%) is used in the synthesis of nitromethane derivatives used as pharmaceuticals, agricultural soil fumigants, and industrial antimicrobials (Markofsky 1991, Angus 2001). Nitromethane also is used as a fuel or fuel additive with methanol in racing cars, boats, and model engines. It formerly was used in the explosives industry as a component in a binary explosive formulation with ammonium nitrate and in shaped charges, and it was used as a chemical stabilizer to prevent decomposition of various halogenated hydrocarbons (NTP 1997, IARC 2000, Angus 2001).
Vorbereitung Methode
Nitromethane was first prepared in 1872 by Kolbe, and is produced commercially by high-temperature vapour-phase nitration of propane. The process, which uses nitric acid as the nitrating agent, is based on a free-radical reaction in which the active species is the NO2 radical (Markofsky, 1991; Angus Chemical Co., 1998).
Nitromethane and the other important nitroparaffins are synthesized commercially by the vapor-phase nitration of propane (Baker and Bollmeier 1978). At temperatures of 370-450°C and pressures of 8-12 atmospheres, nitromethane, nitroethane and 1- and 2-nitropropane are formed and then separated by distillation.
Allgemeine Beschreibung
A colorless oily liquid. Flash point 95°F. May violently decompose if intensely heated when contaminated. Denser than water and slightly soluble in water. Hence sinks in water. Vapors are heavier than air. Moderately toxic. Produces toxic oxides of nitrogen during combustion.
Air & Water Reaktionen
Highly flammable. Slightly soluble in water.
Reaktivität anzeigen
Nitromethane may explode if heated or strongly shocked, especially if mixed with acids, bases [Handling Chemicals Safely 1980. p.687], acetone, aluminum powder, ammonium salts in the presence of organic solvents, haloforms (chloroform, bromoform), or hydrazine in methanol. Ignites on contact with alkyl aluminum or alkyl zinc halides. Reacts violently with strong bases (potassium hydroxide, calcium hydroxide), amines (1,2-diaminoethane, hydrazine), bromine, carbon disulfide, hydrocarbons, formaldehyde, metal oxides, lithium aluminum hydride, sodium hydride, strong oxidizing agents (lithium perchlorate, nitric acid, calcium hypochlorite). Reacts with aqueous silver nitrate to form explosive silver fulminate [Bretherick, 5th ed., 1995, p. 183]. Mixtures of Nitromethane and aluminum chloride may explode when organic matter is present [Chem. Eng. News 26:2257. 1948]. Nitromethane, either alone or in a mixture with methanol and castor oil, has a delayed but violent reaction with powdered calcium hypochlorite [Haz. Home Chem 1963]. Nitromethane reacts violently with hexamethylbenzene [Lewis 2544]. Nitromethane is strongly sensitized by hydrazine [Forshey, D. RR. et al, Explosivestoffe, 1969, 17(6), 125-129].
Hazard
Dangerous fire and explosion risk, lower
explosion limit 7.3% in air. Toxic by ingestion and
inhalation. Thyroid effects, upper respiratory tract
irritant, and lung damage. Possible carcinogen.
Health Hazard
Nitromethane is used primarily as a chemical intermediate in the synthesis of biocides, chemicals, and agricultural products and intermediates. It is slightly toxic to aquatic organisms, has a low bioconcentration potential, and is considered not readily biodegradable. Acute toxicity is low following oral or dermal exposure. Nitromethane is a mild eye irritant and is not likely to cause significant irritation to the skin. Long-term excessive exposure may cause central nervous system effects. Based on animal data, nitromethane is classified as a Category 2B carcinogen (potential human carcinogen).
Brandgefahr
Behavior in Fire: Containers may explode
Industrielle Verwendung
Nitromethane is used as an intermediate in chemical syntheses, but more importantly
it is used as a solvent for coatings and inks. It and the other nitroparaffins are
excellent solvents for vinyls, epoxies, polyamides and acrylic polymers (Baker
and Bollmeier 1978). It also is used as a military propellant and a racing fuel
additive (HSDB 1988). Mixed with methanol and castor oil it is employed as a
model airplane fuel.
mögliche Exposition
Nitromethane is used in the production
of the fumigant, chloropicrin. It is best known as racing car
fuel. It is also used as a solvent and as an intermediate in
the pharmaceutical industry.
Carcinogenicity
Nitromethane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Chemical/Physical. Nitromethane will not hydrolyze because it does not contain a hydrolyzable
functional group.
Stoffwechsel
Nitromethane is converted to nitrite and formaldehyde in a 1:1 ratio by hepatic
microsomes from phenobarbital-pretreated male Sprague-Dawley rats (Sakurai et
al 1980), but no formaldehyde could be detected when microsomes from the nose
or liver of untreated male Fischer-344 rats were incubated with nitromethane
(Dahl and Hadley 1983). Whether a similar conversion occurs in vivo has not been
determined, but the absence of nitromethane metabolism in microsomes from
untreated rats suggests that its metabolism in vivo may be slow.
Versand/Shipping
UN1261 Nitromethane, Hazard Class: 3; Labels:
3-Flammable liquid.
Inkompatibilitäten
May explode from heat, shock, friction,
or concussion. Reacts with alkalis, strong acids; metallic
oxides. Detonates or reacts violently with strong oxidizers,
strong reducing agents such as hydrides; formaldehyde,
copper, copper alloys; lead, lead alloys; hydrocarbons and
other combustibles, causing fire and explosion hazard.
Forms shock sensitive mixture when contaminated with
acids, amines, bases, metal oxides; hydrocarbons, and other
combustible materials.
Waste disposal
Incineration: large quantities
of material may require nitrogen oxide removal by catalytic
or scrubbing processes.
Einzelnachweise
[1] S C LEE M L W. Histidinemia produced in the rat by treatment with nitromethane1.[J]. Nutrition and metabolism, 1975, 18 2: 79-88. DOI:
10.1159/000175579.
[2] T. LEWIS W. B C E Ulrich. Subchronic inhalation toxicity of nitromethane and 2-nitropropane.[J]. Journal of Environmental Pathology Toxicology and Oncology, 1979, 2 5 1: 233-249. DOI:
10.1097/00043764-198005000-00012.
[3] ANTTI ZITTING Heikki S Juha Nickels. Comparison of acute toxic effects of intraperitoneally injected nitromethane and nitroethane in rats[J]. Toxicology letters, 1982, 13 3: Pages 195-201. DOI:
10.1016/0378-4274(82)90211-9.
[4] https://publications.iarc.fr/_publications/media/download/2541/1343003ab32c4c59c08e60cd72e2b97a5ed6b021.pdf
Nitromethan Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
(E)-2-(2-Nitroethenyl)thiophene
polythiniren
2,6-Dimethylbenzaldehyde
3-METHOXY-4-PYRIDINECARBOXYLIC ACID
Berberin
2,6-DICHLOROPHENETHYLISOCYANIDE
7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline
Tianeptine
(E)-2-Nitroethenylbenzene
6-Fluorotryptamine hydrochloride
CYANOMETHYLENETRIBUTYLPHOSPHORANE
4-(2-Aminoethyl)guajakolhydrochlorid
4-(2-AMINO-ETHYL)-2-METHOXY-PHENOL
1-NITROMETHYLCYCLOHEXANOL
4'-(Trifluoromethoxy)acetophenone
2,3-DIMETHOXYPHENETHYLAMINE
1-Nitropropan
2-Nitropropan
1-Aminomethylcyclohexan-1-olhydrochlorid
3-NITROBENZO[B]FURAN-5-OL
7-Methylisochinolin
4,5,6,7-Tetrahydrothieno[3,2,c] pyridine hydrochloride
1-(4-HYDROXY-3-METHOXYPHENYL)-2-NITROETHENE
Fenoldopam
1,1'-Dimethyl-4,4'-bipyridinium-Salze
Ticlopidine
2,4-DIMETHOXYPHENETHYLAMINE
2-(3H-Imidazol-4-yl)-ethylamine
2-(Hydroxymethyl)-2-nitro-1,3-propandiol
Malotilat
2-FLUOROPHENETHYLAMINE
Trometamol
Bronopol (INN)
N-Methyl-1-(methylthio)-2-nitrovinylamin
4-(2-Aminoethyl)pyrocatechinhydrobromid
DL-Isoserine
Isoquinoline, 7-(bromomethyl)- (9CI)
Cycloheptanon
(+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID
1-(Aminomethyl)cyclohexan-1-ol
