Trimethylamin, in w?ssriger L?sung(C > 15%) Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSES, KOMPRIMIERTES FLüSSIGGAS MIT CHARAKTERISTISCHEM GERUCH.
ERSCHEINUNGSBILD
FARBLOSE L?SUNG IN WASSER MIT STECHENDEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die D?mpfe sind schwerer als Luft und k?nnen sich am Boden ausbreiten. Fernzündung m?glich.
PHYSIKALISCHE GEFAHREN
Das Gas ist schwerer als Luft und kann sich am Boden ausbreiten. Fernzündung m?glich.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger Rauche mit Stickstoffoxiden. Starke Base in w?ssriger L?sung. Reagiert sehr heftig mit S?uren. ?tzend. Reagiert sehr heftig mit Oxidationsmitteln und Ethylenoxid. Greift Metalle wie Kupfer, Zink, Aluminium, Zinn und deren Legierungen an.
CHEMISCHE GEFAHREN
Mittelstarke Base. Reagiert sehr heftig mitQuecksilber und Oxidationsmitteln unter Feuer- und Explosionsgefahr. Greift Metalle wie Aluminium, Kupfer, Zink, Zinn und deren Legierungen an.
ARBEITSPLATZGRENZWERTE
TLV: 5 ppm (als TWA); 15 ppm (als STEL); (ACGIH 2005).
MAK: 2 ppm 4,9 mg/m? Spitzenbegrenzung: überschreitungsfaktor I(2); Schwangerschaft: Gruppe C; (DFG 2006).
ARBEITSPLATZGRENZWERTE
TLV: 5 ppm (als TWA); 15 ppm (als STEL); (ACGIH 2005).
MAK: 2 ppm, 4,9 mg/m? Spitzenbegrenzung: überschreitungsfaktor I(2); Schwangerschaft: Gruppe C; (DFG 2006).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation.
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation der D?mpfe und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt eine gesundheitssch?dliche Kontamination der Luft ein.
INHALATIONSGEFAHREN
Eine gesundheitssch?dliche Konzentration des Gases in der Luft wird beim Entweichen aus dem Beh?lter sehr schnell erreicht.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Das Gas reizt stark die Augen und die Atemwege. Schnelle Verdampfung kann zu Erfrierungen führen. Inhalation des Gases kann zu Lungen?dem führen (s.Anm.). Die Auswirkungen treten u.U. verz?gert ein. ?rztliche Beobachtung notwendig.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz ver?tzt die Augen und die Haut. Der Dampf reizt stark die Atemwege. ?tzend beim Verschlucken.
LECKAGE
Gefahrenbereich verlassen! Fachmann zu Rate ziehen! Belüftung. Zündquellen entfernen. Dampf mit feinem Wassersprühstrahl niederschlagen. Pers?nliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabh?ngigem Atemschutzger?t.
LECKAGE
Gefahrenbereich verlassen! Fachmann zu Rate ziehen! Belüftung. Zündquellen entfernen. Wasserstrahl NIEMALS auf die Flüssigkeit richten. Dampf mit feinem Wassersprühstrahl niederschlagen. Pers?nliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabh?ngigem Atemschutzger?t.
R-S?tze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R34:Verursacht Ver?tzungen.
R20/22:Gesundheitssch?dlich beim Einatmen und Verschlucken.
R12:Hochentzündlich.
R41:Gefahr ernster Augensch?den.
R37/38:Reizt die Atmungsorgane und die Haut.
R20:Gesundheitssch?dlich beim Einatmen.
S-S?tze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S29:Nicht in die Kanalisation gelangen lassen.
Aussehen Eigenschaften
C3H9N; N,N-Dimethylmethanamin, TMA. Farbloses, hochentzündliches, reizendes Flüssiggas. Fisch- oder ammoniakartiger Geruch, leicht wasserlöslich.
Gefahren für Mensch und Umwelt
Reizt die Augen und die Atmungsorgane.
Sehr niedrige Geruchsschwelle aber Geruchsermüdung möglich.
Wirkt erstickend und stark reizend auf Augen und Schleimhäute, Lungenödem möglich. Nach Resorption sind Husten, Atemnot, Abhusten blutiger Schleimhautteile und Krämpfe möglich.
Nicht mit starken Säuren und Oxidationsmitteln in Berührung bringen. Hochentzündlich. Bildet mit Luft exlosionsfähige Gemische.
Schutzma?nahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Leck schließen. Zylinder ins Freie bringen, wenn ohne Gefährdung möglich. Dämpfe nicht einatmen.
Kohlendioxid, Pulver. Behälter mit Wasser kühlen. Produkdämpfe mit Wasser niederschlagen.
Brennbar. Dämpfe schwerer als Luft. Im Brandfall Entstehung nitroser Gase möglich.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft, ggf. Atemspende. Arzt hinzuziehen.
Nach Verschlucken: Zitronensaft, Speiseessig oder Eiermilch, dann viel Wasser trinken lassen. Erbrechen vermeiden (Perforationsgefahr!). Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Lösung z. B. in Ethanol als halogenfreie, organische Lösemittelabfälle.
Chemische Eigenschaften
Trimethylamine is compressed gas or liquid.
Flammable gas. Shipped as a compressed gas, it may be
present in an aqueous solution. It has a strong, fishy, ammoniacal
odor. The Odor Threshold is 0.00011-0.87 ppm.
Warning: The Odor Threshold range is so broad that odor
alone should not be used as a warning of potentially
hazardous exposures.
Physikalische Eigenschaften
Trimethylamine has a pungent, fishy, ammoniacal odor at low concentration.It's a colourless liquid with a boiling point around 3.5°C, compared with the higher melting point of 224-226°C for the more polar Me3NO, which presumably has dipole-dipole intermolecular forces.
Trimethylamine is a base, like ammonia. Also like ammonia, it has a trigonal pyramidal structure. The C-N-C bond angle is 110.9°, compared with 107.2° in NH3, presumably due to greater repulsions between the methyl groups. This angle is reduced to 109.0° in Me3NO.
Occurrence
TMA is widely distributed in the environment as a normal constituent of animal and plant tissue and as a result of its formation during the decay of organic matter in plants, animals, fish, sewage and animal waste (Graedel 1978; Hippe et al 1977; Oremland et al 1982). The amine is formed primarily as the result of microbial degradation of the plant and animal constituents betaine and choline and from bacterial reduction of trimethylamine oxide, a common constituent of aquatic organisms. It also occurs naturally in a variety of foodstuffs and in tobacco smoke and these are the most likely sources of human exposure (HSDB 1988).
Numerous strains of bacteria isolated from various sources have been found capable of growing on TMA (HSDB 1988). Degradation products formed under anaerobic conditions include dimethylamine, formaldehyde, formate and C02, while under aerobic conditions, TMA is converted to dimethylamine, ammonia and methane.
Verwenden
Trimethylamine is used as a warning agent for natural gas, a synthetic flavor (fish) ingredient, and in the synthesis of photochemicals, choline salts, flotation agents, dyes, pesticides, ion-exchange resins, cationic starches, and intense sweeteners (HSDB 2006).
Organic synthesis, especially of choline salts, warning agent for natural gas, manufacture of disinfectants, flotation agent, insect attractant, quaternary ammonium compounds, plastics.
Definition
ChEBI: Trimethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an methyl group. It has a role as a human xenobiotic metabolite and an Escherichia coli metabolite. It is a tertiary amine and a member of methylamines. It is a conjugate base of a trimethylammonium.
Vorbereitung Methode
Trimethylamine (TMA) is produced by several methods: from the reaction of ammonia and methanol; from paraformaldehyde and ammonium chloride; by the action of formaldehyde and formic acid on ammonia; and by the interaction of methanol and ammonia over a catalyst at high temperature (Hawley 1981; HSDB 1988). TMA is sold as an aqueous solution or as a liquefied gas (Windholz et al 1983) in which the aqueous solution is available as 25, 30, and 40% and anhydrous as 99% minimum. The impurities consist of ammonia at no more than 0.2% by weight of solution and formaldehyde at no more than 0.3% by wt. of solution (Rick 1985). U.S. production was estimated to be approximately 15,322 tons in 1984 (HSDB 1988).
synthetische
Trimethylamine can be synthesized from paraformaldehyde and ammonium chloride, by the reaction of formic acid, formaldehyde, and ammonia, and by interaction of methanol and ammonia with a catalyst at high temperature.
Reaktionen
Trimethylamine (TMA) has been used in the preparation of poly[9,9′-bis(6′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), a water-soluble, cationic conjugated polymer used in label-free DNA microarrays. It can also be used to prepare benzyltrimethylammonium chloride, which then reacts with sodium ethoxide to form benzyltrimethylammonium ethoxide.The adsorption of TMA on the gold surface of trimethylsilylated barium nitrate-gold/titanosilicate catalyst acts as a promoter for the propylene epoxidation with oxygen and hydrogen.
Allgemeine Beschreibung
A colorless gas with a fishlike odor at low concentrations changing to ammonia-like odor at higher concentrations. Shipped as a liquid under its own vapor pressure. Contact with the unconfined liquid can cause frostbite from evaporative cooling or chemical type burns. The gasis corrosive and dissolves in water to form flammable, corrosive solutions. Gas is an asphyxiate by the displacement of air. Produces toxic oxides of nitrogen during combustion. Prolonged exposure to heat can cause the containers to rupture violently and rocket. Long-term inhalation of low concentrations or short -term inhalation of high concentrations has adverse health effects.
Air & Water Reaktionen
Highly flammable and easily ignited. Water soluble.
Reaktivit?t anzeigen
TRIMETHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Contamination of an ethylene oxide tank with trimethylamine caused an explosion [BCISC Quart. Safety Summ., 1966, 37, 44].
Health Hazard
TMA is formed naturally from the biodegradation of plants, fish and animal products, and is ingested in foods such as fish, or from foods containing TMA precursors [e.g. trimethylamine oxide (TMAO), choline, and L-carnitine], which are metabolized to TMA by enterobacteria (Bain et al. 2005). Human exposure to TMA vapor has caused respiratory and eye irritation and corneal lesions. Effects in laboratory animals consisted of respiratory tract toxicity (gasping, labored breathing, lung lesions), eye lesions, neurotoxicity (apathy, splayed hind- or forelimbs, uncoordinated movements, convulsions, brain lesions), and some studies also found pathological changes of the liver, spleen, and kidneys.
Sicherheitsprofil
Poison by intravenous
route. Moderately toxic by subcutaneous
and rectal routes. Mildly toxic by inhalation.
A very dangerous fire hazard when exposed
to heat or flame. Self-reactive. Moderately
explosive in the form of vapor when
exposed to heat or flame. Can react with
oxidizing materials. To fight fire, stop flow
of gas. Potentially explosive reaction with
bromine + heat, ethylene oxide,
triethynylaluminum. When heated to
decomposition it emits toxic fumes of NOx.
See also AMINES.
m?gliche Exposition
Trimethylamine is used as a chemical
intermediate in organic synthesis of quaternary ammonium
com pounds; as an insect attractant; as a warning agent in
natural gas; flotation agent.
Carcinogenicity
No studies were found that examined the carcinogenicity of Trimethylamine in humans. Because mechanisms have been proposed by which the known carcinogen N47 nitrosodimethylamine can be formed from Trimethylamine and TMAO (Bain 2005) in the presence of nitrosating agents, there is some concern about the neoplastic potential of Trimethylamine. Thus, the German exposure guidelines warn that co-exposure to Trimethylamine and nitrosating agents should be minimized (see Section 8.2.). However, a 2-year mouse and rat inhalation study with the related amine DMA, which can also potentially form N-nitrosodimethylamine, showed no tumor formation despite severe chronic nasal lesions (CIIT 1990).
l?uterung methode
Dry triethylamine by passing the gas through a tower filled with solid KOH. Water and impurities containing labile hydrogen were removed by treatment with freshly sublimed, ground, P2O5. It has been refluxed with acetic anhydride, and then distilled through a tube packed with HgO and BaO. [Comyns J Chem Soc 1557 1955.] For more extensive purification, trimethylamine is converted to the hydrochloride, crystallised (see below), and regenerated by treating the hydrochloride with excess aqueous 50% KOH, the gas is passed through a CaSO4 column into a steel cylinder containing sodium ribbon. After 1-2 days, the cylinder is cooled to -78o and hydrogen and air are removed by pumping. [Day & Felsing J Am Chem Soc 72 1698 1950.] Me3N has been distlled from trap-to-trap and degassed by freeze-pump-thaw [Halpern et al. J Am Chem Soc 108 3907 1986]. It is commercially supplied in a pressure tin. [Beilstein 4 H 43, 4 I 322, 4 II 553, 4 III 99, 4 IV 134.]
Inkompatibilit?ten
A medium strong base. Violent reaction
with strong oxidizers (such as chlorine, bromine, fluorine),
ethylene oxide; nitrosating agents, for example, nitrites,
sodium nitrite, nitrous gases, nitrous acid) capable of
releasing carcinogenic nitrosamines.); keep away from mercury,
strong acids. Corrosive to many metals, for example,
zinc, brass, aluminum, copper, tin, and their alloys.
Waste disposal
Return refillable compressed
gas cylinders to supplier. Nonrefillable cylinders should be
disposed of in accordance with local, state and federal regulations.
Allow remaining gas to vent slowly into atmosphere
in an unconfined area or exhaust hood. Refillabletype
cylinders should be returned to original supplier with
any valve caps and outlet plugs secured and valve protection
caps in place.
Trimethylamin, in w?ssriger L?sung(C > 15%) Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
trimethyl p-dodecyl benzyl ammonium chloride
Betain
polysulfone anion exchange membrane
(2-Acetoxyethyl)trimethylammoniumbromid
2-((Aminocarbonyl)oxy)-N,N,N-tri-methylethan-aminiumchlorid
2-(Acetyloxy)-N,N,N-trimethyl-1-propanaminiumchlorid
Cholinhydroxid
Alachlor (ISO)
Anion exchange resin,strong basic styrene
Parathion-methyl (ISO)
Sulfotep (ISO)
(2-Acetoxyethyl)trimethylammoniumiodid
Parathion (ISO)
N,N-Dimethylmethylenammoniumiodid
Benzyltrimethylammoniumchlorid
Betainhydrochlorid
N-Cetyl-N,N,N-trimethylammonium-bromid
Triazophos E.C.
Trimethylamin, N-oxid
Cholinchlorid
DL-Carnitinhydrochlorid
Miltefosine
Hexamethoniumbromid
benzyltrimeehyl ammonium chloride
trimethyl α-hexadecyl betaine
styrene type polyethylene homogeneous anion exchange membrane
Hexadecyltrimethylammoniumhydroxid
DOWEX(R) 1X8
cationic fatliquor agent DLF-4
chloroalcohol type homogeneous strongly basic anion exchange membrane
DL-CARNITINE
Chlormequatchlorid (ISO)
(N-HEXYL)TRIMETHYLAMMONIUM BROMIDE
Natriumcyclamat
Trimethylammoniumchlorid
interpenetrating network ion exchange resin
Acetylcholinchlorid
O,O-Diethyl-O-1-phenyl-1,2,4-triazol-3-ylthio-phosphat
(Hydrazinocarbonylmethyl)trimethylammoniumchlorid
2,5-Dichlorpyridin
