Hexandinitril Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
GERUCHLOSE, öLIGE, FARBLOSE FLüSSIGKEIT.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen oder Verbrennen unter Bildung hochgiftigen Cyanwasserstoffs (s. ICSC 0492). Reagiert sehr heftig mit starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 2 ppm (als TWA); Hautresorption; (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt eine gesundheitsschädliche Kontamination der Luft nicht oder nur sehr langsam ein
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen und die Haut. Exposition kann Krämpfe verursachen. Exposition kann zu Bewusstlosigkeit führen. Exposition kann zum Tod führen. ärztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Möglich sind Auswirkungen auf Blut und Nebennieren mit nachfolgender Blutarmut und Gewebeschäden.
LECKAGE
Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Kanalisation spülen. Persönliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36/38:Reizt die Augen und die Haut.
R23/25:Giftig beim Einatmen und Verschlucken.
S-Sätze 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 möglich, dieses Etikett vorzeigen).
S39:Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Adiponitrile is a combustible, colorless transparent to yellow, oily liquid with a slight bitter taste. Soluble in methanol, ethanol, chloroform. Insoluble in water, cyclohexane, ether, carbon disulfide and carbon tetrachloride. It decomposes on heating to react violently with strong oxidants. Upon burning, the highly toxic hydrogen cyanide is produced.
Verwenden
Adiponitrile is mainly used in the production of hexamethylenediamine for manufacturing nylon 6,6. Lesser uses include that in organic synthesis and in the preparation of adipoguanamine, which is used as an extractant for aromatic hydrocarbons. This chemical is an important intermediate for the manufacture of synthetic fiber.
synthetische
The main method of industrial production of adiponitrile is the amination of adipic acid. Adipic acid and excess ammonia are reacted in the presence of catalyst phosphoric acid or its salts or esters at a temperature of 270-290°C to generate diammonium adipate, which is then heated and dehydrated to generate crude adiponitrile, The product is obtained by rectification.
Vorbereitung Methode
Adiponitrile may be prepared by reacting butadiene with hydrogen cyanide, by the
electrodimerization of acrylonitrile, by heating adipamide with acetic anhydride in
the presence of cobalt or by reacting 1,4-dichlorobutane with sodium cyanide
(HSDB 1988). Impurities such as propionitrile, bis (cyanoethyl) ether or acrylonitrile
may be present depending on the method of manufacture (Smiley 1981).
Allgemeine Beschreibung
Adiponitrile appears as a colorless to light yellow liquid which is fairly soluble and is less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
1,4-Dicyanobutane is incompatible with strong oxidizers. 1,4-Dicyanobutane is also incompatible with strong acids, strong bases and strong reducing agents. .
Health Hazard
The acute toxicity of adiponitrile is somewhat lower than that of malononitrile. It is toxic by inhalation and oral routes. Inhalation of its vapors can cause nausea, vomiting, respiratory tract irritation, and dizziness. The symptoms are similar to those of other aliphatic mono- and dinitriles. Similar poisoning effects may be manifested from ingestion of this compound. However, its toxicity is very low from skin absorption.
Short et al. (1990) reported mortality and reduced weight gain in rats within one week after exposed to adiponitrile at 493 mg/m
3. However, at an exposure level of 99 mg/m
3 for 13 weeks the animals showed the sign of slight anemia but no histopathological evidence of organ toxicity.
LC50 value, inhalation (rats): 1710 mg/m
3/ 4 hr
LD50 value, oral (mice): 172 mg/kg
There is no report of its teratogenicity or cancer-causing effects in animals or humans.
Brandgefahr
Combustion products may contain hydrocyanic acid (HCN). Vapor may explode if ignited in an enclosed area. When heated to decomposition, 1,4-Dicyanobutane emits highly toxic fumes. Avoid oxidizing material. Hazardous polymerization may not occur.
Industrielle Verwendung
Adiponitrile is used in nylon manufacturing, synthetic fiber synthesis, and in the
manufacture of rubber accelerators and corrosion inhibitors. It is also used as an
extractant for aromatic hydrocarbons (Smiley 1981).
Sicherheitsprofil
Poison by inhalation, ingestion, subcutaneous, and intraperitoneal routes. The nitrile group wdl behave as a cyanide when ingested or absorbed in the body. It produces disturbances of the respiration and circulation, irritation of the stomach and intestines, and loss of weight. Its low vapor pressure at room temperature makes exposure to harmful concentrations of its vapors unlikely if handled with Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of CN-. Can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. See also HYDROCYANIC ACID and NITRILESreasonable care in well-venulated areas.
mögliche Exposition
Is used to manufacture corrosion inhibitors, rubber accelerators, and Nylon 66; and in organic synthesis.
Environmental Fate
The mechanism of adiponitrile’s toxicity relates to its ability to
release cyanide both in vitro and in vivo. Cyanide then forms
a stable complex with ferric iron in the cytochrome oxidase
enzyme. Since this enzyme occupies a central role in the utilization
of oxygen in practically all cells, inhibition produces an
inhibition of cellular respiration.
Stoffwechsel
Animal studies indicated that the concentrations of thiocyanate in the blood and
urine of guinea pigs injected with adiponitrile were proportional to the doses
administered. Following administration of adiponitrile, 79% was eliminated as
thiocyanate in the urine of guinea pigs (H?rtung 1982). Of the cyanide antidotes,
thiosulfate was most effective in protecting against adiponitrile poisoning, and
nitrite was less effective. However, on the basis of the ratio between administered
adiponitrile dose and quantity of cyanide detected, Ghiringhelli, (1955) concluded
that a greater part of the dose was metabolized to cyanide.
Versand/Shipping
UN2205 Adiponitrile, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
läuterung methode
Reflux adiponitrile over P2O5 and POCl3, and fractionally distil it, then fractionate it through an efficient column. The liquid is TOXIC and is an IRRITANT. [Braun & Rudolph Chem Ber 67 1770 1934, Reppe et al. Justus Liebigs Ann Chem 596 127 1955, Gagnon et al. Can J Chem 34 1662 1956, Copley et al. J Am Chem Soc 62 228 1940, Beilstein 2 IV 1947.]
Inkompatibilitäten
May form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause violent reactions: fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Also incompatible with strong reducing agents such as hydrideds and active metals. Permissible Exposure Limits in Air
Waste disposal
Add excess alcoholic KOH. Than evaporate alcohol and add calcium hypochlorite. After 24 hours, flush to sewer with water. Can also be incinerated with afterburner and scrubber to remove nitrogen oxides.
Hexandinitril Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
