3,6-Diazaoctan-1,8-diamin Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE BIS GELBE, VISKOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger Rauche mit Stickstoffoxiden. Starke Base. Reagiert sehr heftig mit S?uren. ?tzend. Reagiert sehr heftig mit starken Oxidationsmitteln. Reagiert mit Ketonen, halogenierten Kohlenwasserstoffen, Cyaniden, Nitrilen und Epoxiden. Greift Metalle wie Aluminium, Zink, Kupfer und Legierungen an.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK: Sensibilisierung der Haut; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation der D?mpfe und über die Haut.
INHALATIONSGEFAHREN
Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitssch?dliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz ver?tzt die Augen, die Haut und die Atemwege. ?tzend beim Verschlucken. Inhalation des Dampfes kann zu Lungen?dem führen (s.Anm.). Die Auswirkungen treten u.U. verz?gert ein. ?rztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Wiederholte oder andauernde Inhalation kann asthmatische Beschwerden hervorrufen. (S. Anm.)
LECKAGE
Ausgelaufene Flüssigkeit m?glichst in abdichtbaren Beh?ltern sammeln. Reste mit viel Wasser wegspülen. Chemikalienschutzanzug mit umgebungsluftunabh?ngigem Atemschutzger?t.
R-S?tze Betriebsanweisung:
R21:Gesundheitssch?dlich bei Berührung mit der Haut.
R34:Verursacht Ver?tzungen.
R43:Sensibilisierung durch Hautkontakt m?glich.
R52/53:Sch?dlich für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.
S-S?tze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Beschreibung
Triethylenetetramine (TETA and trien) also known as trientine (INN) when used medically, is an organic compound with the formula
[CH2NHCH2CH2NH2]2.
The pure freebase is a colorless oily liquid, but, like many amines, older samples assume a yellowish color due to impurities resulting from air-
oxidation.
It is soluble in polar solvents.
The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of Triethylenetetramine.
The hydrochloride salts are used medically as a treatment for copper toxicity.
Chemische Eigenschaften
Triethylenetetramine is a corrosive liquid.
Verwenden
Triethylenetetramine is used as an amine hardener in epoxy resin of the bisphenol A type.It is used in synthesis of detergents, softeners, and dyestuffs; manufacture of pharmaceuticals; vulcanization accelerator of rubber; thermo setting resin; epoxy curing agent; lubricating-oil additive; analytical reagent for Cu, Ni; chelating agent; treatment of Wilson's disease.
Vorbereitung Methode
Triethylenetetramine(TETA) is manufactured by reacting ethylene dichloride and
ammonia under controlled conditions.
Allgemeine Beschreibung
A yellowish liquid. Less dense than water. Combustible, though may be difficult to ignite. Corrosive to metals and tissue. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.
Chemische Eigenschaften
Triethylenetetramine (TETA) is hygroscopic, corrosive, and has a strong ammoniacal odor. With water a crystalline hydrate is formed. Like DETA, it is completely miscible with water and many polar organic solvents, but less so with lipids; with CCl4 a violent reaction occurs. Its four pKa values are 3.32, 6.67, 9.20, and 9.92. Technical-grade TETA is sometimes available as a distillation cut that also contains branched isomers and cyclic compounds.
Reaktivit?t anzeigen
Triethylenetetramine is a strong base; reacts violently with strong oxidants; attacks aluminum, zinc, copper and its alloys. Handling Chemicals Safely 198. p. 934).
Health Hazard
Vapors from hot liquid can irritate eyes and upper respiratory system. Liquid burns eyes and skin. May cause sensitization of skin.
Brandgefahr
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Kontakt-Allergie
Triethylenetetramine is used as an amine hardener in
epoxy resins of the bisphenol A type. Cross-sensitivity is
possible with diethylenetriamine and diethylenediamine.
Sicherheitsprofil
Poison by intravenous
route. Moderately toxic by ingestion and
skin contact. An experimental teratogen.
Experimental reproductive effects. Mutation
data reported. A corrosive irritant to skin,
eyes, and mucous membranes. Causes skin
sensitization. Combustible when exposed to
heat or flame. Ignites on contact with
cellulose nitrate of high surface area. Can
react with oxidizing materials. To fight fire,
use CO2, dry chemical, alcohol foam. When
heated to decomposition it emits toxic
fumes of NOx.
Toxikologie
Triethylenetetramine may induce lung edema on inhalation of its vapors. The compound is also an effective skin sensitizer. Following repeated dosing (ca. 50 mg each, 17 – 55 times) onto the skin of pregnant and nonpregnant guinea pigs, significant amounts were absorbed by the strongly irritated skin, leading to toxic effects in the kidneys, liver, brain, and placenta and causing abortion. Triethylenetetramine proved to be a mutagen in vitro but not in vivo.
Carcinogenicity
TETA was mutagenic in bacterial assays
and was positive in sister chromatid exchanges
and unscheduled DNA synthesis tests in vitro.8
It was not clastogenic in the mouse micronucleus
test in vivo after oral or intraperitoneal
administration.
l?uterung methode
Dry the amine with sodium, then distil it under a vacuum. Further purification has been via the nitrate or the chloride salts. For example, Jonassen and Strickland [J Am Chem Soc 80 312 1958] separated TRIEN from admixture with TREN (38%) by solution in EtOH, cooling to approximately 5o in an ice-bath and adding conc HCl dropwise from a burette, keeping the temperature below 10o, until all of the white crystalline precipitate of TREN.HCl (see p 191) had formed and was removed. Further addition of HCl then precipitated thick, creamy white TRIEN.HCl (see below) which was crystallised several times from hot water by adding an excess of cold EtOH. The crystals were finally washed with Me2CO, then Et2O and dried in a vacuum desiccator. [Beilstein 4 H 255, 4 II 695, 4 III 542, 4 IV 1242.]
3,6-Diazaoctan-1,8-diamin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
N,N'-Bis[2-(dimethylamino)ethyl]-N,N'-dimethylethylendiamin
N,N'-Bis(2-aminoethyl)ethylendiamindihydrochlorid
3-Azapentan-1,5-diamin
triethylene tetraamine hexamethylene phosphoric acid
3,6-Diazaoctan-1,8-diamintetrahydrochlorid
1,4-Diazabicyclo(2.2.2)octan
Piperazin-1,4-diethylamin
1-(2-Hydroxyethyl)imidazolidin-2-on
1-(2-Aminoethyl)imidazolidin-2-on
3H,6H-2a,5,6,8a-Tetraazaacenaphthylene, octahydro-5a,8b-dimethyl-, cis-
