General Description
Malononitrile(109-77-3) appears as 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.
Reactivity Profile
MALONONITRILE(109-77-3) 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].
Air & Water Reactions
Soluble in water.
Hazard
Toxic by ingestion and inhalation.
Health Hazard
Metabolized by body to cyanide and thiocyanate; effects of inhalation of toxic fumes will be related to cyanide. Causes brain and heart damage related to lack of cellular oxygen. It is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful, for a 70 kg (150 lb.) person.
Potential Exposure
Malononitrile is used in organic synthesis; as a lubricating oil additive; for thiamine synthesis;
for pteridine-type anticancer 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
Fire Hazard
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.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, 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 i
Shipping
UN2647 Malononitrile, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials. UN3439 Nitriles, solid,
toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous
materials, Technical Name Required
Incompatibilities
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.
Description
Malonitrile is an aliphatic nitrile. It can release cyanide through
either chemical or biological transformation. Malonitrile was
used decades ago for treating certain forms of mental illness.
Chemical Properties
Malononitrile or 109-77-3 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.
Waste Disposal
Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA
regulations governing storage, transportation, treatment,
and waste disposal
Uses
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
Uses
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.
Definition
ChEBI: A dinitrile that is methane subtituted by two cyano groups.
Production Methods
Malononitrile is prepared by continuous introduction of preheated acetonitrile and
cyanogen chloride into a tube reactor until the reaction mixture reaches a temperature
of approximately 780°C.
Industrial uses
Malononitrile(109-77-3) 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.
Environmental Fate
When heated to decomposition, nitriles may release cyanide.
Malonitrile appears to decompose rapidly in contact with soil
and sediment.
Metabolism
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.
storage
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℃.
Purification Methods
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.
