Malonsäuredinitril

Bezeichnung:Malonsäuredinitril

CAS-Nr109-77-3

Englisch Name:Malononitrile

CBNumberCB2259712

SummenformelC3H2N2

Molgewicht66.06

MOL-Datei109-77-3.mol

Synonyma

Malononitril

Malonsäuredinitril

Propandinitril

Malonsäuredinitril physikalisch-chemischer Eigenschaften

Schmelzpunkt	30-32 °C (lit.)
Siedepunkt	220 °C (lit.)
Dichte	1.049 g/mL at 25 °C (lit.)
Dampfdruck	1 hPa (50 °C)
Brechungsindex	1.4150
Flammpunkt	234 °F
storage temp.	2-8°C
Löslichkeit	133g/l
pka	11(at 25℃)
Aggregatzustand	Crystalline Low Melting Mass
Farbe	White to yellow-brown
Wichte	1.049
PH	pH : 4.5
Wasserlöslichkeit	13.3 g/100 mL (20 ºC)
Merck	14,5711
BRN	773697
Expositionsgrenzwerte	TLV-TWA 8 mg/m³ (3 ppm) (NIOSH).
Dielectric constant	46.0
InChIKey	CUONGYYJJVDODC-UHFFFAOYSA-N
CAS Datenbank	109-77-3(CAS DataBase Reference)
NIST chemische Informationen	Malononitrile(109-77-3)
EPA chemische Informationen	Malononitrile (109-77-3)

Sicherheit

Kennzeichnung gefährlicher	T,N
R-Sätze:	23/24/25-50/53
S-Sätze:	23-27-45-60-61
RIDADR	UN 2647 6.1/PG 2
WGK Germany	3
RTECS-Nr.	OO3150000
F	8
Selbstentzündungstemperatur	365 °C
TSCA	Yes
HazardClass	6.1
PackingGroup	II
HS Code	29269090
Giftige Stoffe Daten	109-77-3(Hazardous Substances Data)
Toxizität	LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)

Gefahreninformationscode (GHS)

Malononitrile Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE KRISTALLEODER WEISSES PULVER.
CHEMISCHE GEFAHREN
Polymerisiert unter Einfluss von Temperaturen über 130°Coder unter Einfluss von Basen. Feuer- und Explosionsgefahr. Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Gase, mit Cyanwasserstoffund Stickstoffoxiden. Greift viele Metalle unter Bildung brennbarer/explosionsfähiger Gase an (z.B. Wasserstoff, ICSC-Nr. 0001).
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (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 langsam eine gesundheitsschädliche Kontamination der Luft ein.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt stark die Augen, die Haut und die Atemwege. Möglich sind Auswirkungen auf die Zellatmung (Hemmung) mit nachfolgenden Krämpfen, Herzfunktionsstörungenund Atemversagen. Exposition gegenüber hohen Konzentrationen kann zum Tod führen. ärztliche Beobachtung notwendig. Die Auswirkungen treten u.U. verzögert ein.
LECKAGE
Zündquellen entfernen. Verschüttetes Material aufsaugenoder verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Chemikalienschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Aussehen Eigenschaften
C3H2N2; Malonitril, Malodinitril. Gelbliche Flüssigkeit ohne Geruch.
Gefahren für Mensch und Umwelt
Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
Inhalation führt zu Atemnot. Wird über die Haut aufgenommen. Kann Blausäure freisetzten.
Nicht stark erhitzen.
LD₅₀ (oral, Ratte): 61 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser.
Brennbar. Bei Zersetzung Explosionsgefahr. Im Brandfall werden nitrose Gase und Blausäure freigesetzt.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Bei geöffnetem Lidspalt mit reichlich fliessendem Wasser (Augendusche!) mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Sofort Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen auslösen. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Mit Wasser in der Hitze zu Malonsäure und Ammoniak hydrolysieren. Dann zu den halogenfreien, organischen Lösemittelabfällen geben.
Beschreibung
Malonitrile, also known as Malononitrile, is an aliphatic nitrile that can release cyanide through chemical or biological transformation. It was also used decades ago for treating certain forms of mental illness.
Chemische Eigenschaften
Malononitrile is a white powder or colorless, odorless crystalline substance. It may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.
Verwenden
Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet
Verwenden
The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups.
Vorbereitung Methode
Malononitrile can be synthesized by a continuous method where preheated acetonitrile and cyanogen chloride are introduced into a tube reactor until the reaction mixture reaches a temperature of about 780°C. Another way to prepare malononitrile is by reacting phosphorus pentachloride with cyanoacetamide, or by using phosphorus pentoxide to react with malonamide or cyanoacetamide.
DOI: 10.15227/orgsyn.010.0066
Definition
ChEBI: Malononitrile is a dinitrile that is methane substituted by two cyano groups. It is a dinitrile and an aliphatic nitrile.
Allgemeine Beschreibung
A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.
Air & Water Reaktionen
Soluble in water.
Reaktivität anzeigen
Malononitrile is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].
Hazard
Toxic by ingestion and inhalation.
Health Hazard
Malononitrile is a highly toxic compound by all toxic routes. Its acute toxicity is somewhat greater than that of the aliphatic mononitriles, propionitrile, and butyronitrile. The increased toxicity may be attributed to the greater degree of reactivity in the molecule arising from two- CN functional groups. The acute toxic symptoms in test animals have not been well documented. An intraperitoneal dose of 10 mg/kg was lethal to rats.
LD50 value, intravenous (rabbits): 28 mg/kg
LD50 value, oral (mice): 19 mg/kg
Malononitrile is an eye irritant. The irritation from 5 mg in 24 hours was severe in rabbits’ eyes. There is no report of teratogenic and carcinogenic action in animals or humans.
Brandgefahr
When heated to decomposition, Malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.
Industrielle Verwendung
Malononitrile is used primarily as an intermediate in the synthesis of drugs and vitamins (thiamine). It has also been employed in the manufacture of photosensitizes, acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating oil.
Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.
Sicherheitsprofil
Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70-80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.
mögliche Exposition
Primary Irritant. Malononitrile is used in organic synthesis, as a lubricating oil additive, for thiamine synthesis, for pteridine-type anti-cancer agent synthesis, and in the synthesis of photosensitizers, acrylic fibers, and dyestuffs. It has also been used in the treatment of various forms of mental illness. It has been used as a leaching agent for gold.
Erste Hilfe
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Environmental Fate
When heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.
Stoffwechsel
The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.
Lager
Color Code—Blue: Health Hazard/Poison: Store in a secure poison location. Prior to working with this chemical you should be trained on its proper handling and storage. Store in a refrigerator under an inert atmosphere for prolonged storage. Keep away from strong bases. May polymerize violently on prolonged heating at 129℃ or in contact with strong bases at lower temperatures. May spontaneously explode on storing above 7080℃.
Versand/Shipping
This compound requires a shipping label of “POISONOUS/TOXIC MATERIALS.” It falls in Hazard Class 6.1 and Packing Group II.
läuterung methode
Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]
Toxicity evaluation
The acute toxicity of malonitrile and related alkyl nitriles is thought to be due to release of cyanide through metabolism of the parent compound. Signs of acute malonitrile intoxication including dyspnea, ataxia, and convulsions are similar to those noted with acute cyanide intoxication. The onset and duration indicate that these nitriles require metabolism to elicit toxicity. Cyanide and thiocyanate have both been found in urine and blood after malonitrile exposure.
Inkompatibilitäten
Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

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