2,2-AZOBISISOBUTYRONITRILE
2,2-Azobisisobutyronitrile is a white crystalline powder that is soluble in organic solvents like methanol, ethanol, and acetone, but insoluble in water.
2,2-Azobisisobutyronitrile is commonly used as a polymerization initiator in various industrial processes, including the production of plastics, rubber, and acrylic fibers.
2,2-Azobisisobutyronitrile appears as a white powder that is soluble in alcohols and common organic solvents but remains insoluble in water.
CAS Number: 78-67-1
EC Number: 201-132-3
Chemical Formula: C8H12N4
Molecular Weight: 164.21
Synonyms: 78-67-1, 2,2′-Azobis(2-methylpropionitrile), Azobisisobutyronitrile, AIBN, 2,2′-Azobisisobutyronitrile, Genitron, 2,2′-AZOBIS(ISOBUTYRONITRILE), Aivn, Azdh, Vazo, Azobisisobutylonitrile, Porofor N, 2,2′-Azodiisobutyronitrile, Pianofor an, Porophor N, Aceto AZIB, Azobis(isobutyronitrile), Porofor 57, Chkhz 57, VAZO 64, (E)-Azobis(isobutyronitrile), 34241-39-9, Propanenitrile, 2,2′-azobis[2-methyl-, 2,2-Azodiisobutyronitrile, AZODIISOBUTYRONITRILE, 2,2′-Dimethyl-2,2′-azodipropiononitrile, Azodiisobutyrodinitrile, azo-bisisobutyronitrile, 2,2′-Azobis(2-methylpropanenitrile), azo-bis-isobutyronitrile, 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile, alpha,alpha’-Azodiisobutyronitrile, 2,2′-Dicyano-2,2′-azopropane, NSC 1496, alpha,alpha-azoisobutyronitrile, Propionitrile, 2,2′-azobis(2-methyl-, 2,2′-Dimethyl-2,2′-azodipropionitrile, Propanenitrile, 2,2′-azobis(2-methyl-, Azodi(isobutyronitrile), FZ6PX8U5YB, Azobis(2-methylpropionitrile), 2,2′-Azodi(isobutyronitrile), (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile), 2,2′-azobis(2-cyanopropane), 2,2′-Azobis[isobutyronitrile], DTXSID1026457, NSC-1496, NSC-68042, 2,2′-(E)-diazene-1,2-diylbis(2-methylpropanenitrile), 2,2′-Azobis-(2-methylpropanenitrile), Propionitrile, 2,2′-azobis[2-methyl-, Azobis[isobutyronitrile], .alpha.,.alpha.’-Azodi(isobutyronitrile), .alpha.,.alpha.’-Azobis(isobutylonitrile), 2,2′-azodipropionitrile, 2,2′-Azobis(2-methylpropionitrile), 98%, 2-[(E)-2-(1-cyano-1-methylethyl)diazen-1-yl]-2-methylpropanenitrile, Propanenitrile, 2,2′-(1,2-diazenediyl)bis(2-methyl-, DTXCID60809637, Propionitrile,2′-azobis[2-methyl-, Propanenitrile,2′-azobis[2-methyl-, 2,2′-Azobis[2-methylpropionitrile], WLN: NCX1&1&NUNX1&1&CN, 2,2′-azobis-(2-methylpropionitrile), 2,2′-azobis-[2-methylpropionitrile], CAS-78-67-1, .alpha.,.alpha.’-Azobis(isobutyronitrile), .alpha.,.alpha.’-Azobis[isobutyronitrile], CCRIS 4287, HSDB 5220, .alpha.,.alpha.’-Azodisobutyric acid dinitrile), EINECS 201-132-3, UNII-FZ6PX8U5YB, 2,2′-Azobis (2-methylpropionitrile), AI3-28716, alpha,alpha’-Azodiisobutyric acid dinitrile, alpha,alpha-Azobisisobutyronitrile, Genitron AZDN, 2,2-Azobis(2-Methylpropionitrile), Genitron AZDN-FF, 2,2′-Azobis(2-methylpropanitrile), MFCD00013808, ADZN, azo-diisobutyronitrile, azo bisisobutyronitrile, azobis isobutyronitrile, azobis-isobutylonitrile, azobis-isobutyronitrile, azobisiso butyronitrile, azobisiso-butylonitrile, azobisiso-butyronitrile, azobisisobutyro nitrile, azobisisobutyro-nitrile, PERKADOX AIBN, PEROXAN AZDN, azo-di-isobutyronitrile, Vazo-64, azo(bisisobutyronitrile), azo-bisiso-butyronitrile, azobis-iso-butylonitrile, azobis-iso-butyronitrile, a,a’-azoisobutyronitrile, azo-bis-iso-butyronitrile, azo-bis-isobutyro-nitrile, azobis(iso-butyronitrile), Azobis (isobutyronitrile), POROFOR-57, SCHEMBL120, SCHEMBL122, VAZO CATALYST 64, 2,2’azobisisobutyronitrile, azo-bis-(isobutyronitrile), 2,2′-azobisisobutyronitril, EC 201-132-3, trans-Azo-2-cyanoisopropane, 2.2′-Azobisisobutyronitrile, 2,2′-azodi-isobutyronitrile, 2,2-azodi(isobutyronitrile), 2,2′-azo bisisobutyronitrile, 2,2′-azobis isobutyronitrile, 2,2′-azobis(2cyanopropane), 2,2′-azobis-isobutyronitrile, 2,2′-azobisiso-butyronitrile, 2,2′-azobisisobutyro-nitrile, a,a’-azobis(isobutyronitrile), azobis (2-methylpropionitrile), 2,2′-azo-bis-isobutyronitrile, 2,2′-azobis isobutyro-nitrile, 2,2’azobis-(isobutyronitrile), 2.2′-azobis(isobutyronitrile), alpha,alpha-azoisobutyro-nitrile, SCHEMBL6522063, 2-(1-cyano-1-methyl-ethyl)azo-2-methyl-propanenitrile, azobis (2-methyl-propionitrile), CHEMBL1886625, 2,2′-azo-bis(isobutyronitrile), 2,2′-Azobis (isobutyronitrile), 2,2′-azobis-(isobutyronitrile), alpha,alpha’ azodiisobutyronitrile, DTXSID70859108, NSC1496, CHEBI:189360, OZAIFHULBGXAKX-VAWYXSNFSA-N, 2,2’azobis(2-methylproponitrile), alpha,alpha’-azobisisobutyronitrile, 2,2’azobis(2-methylpropionitrile), alpha, alpha’-azodiisobutyronitrile, 2,2′ azobis(2-methylproponitrile), 2,2′-azobis(2-methylpropinitrile), 2-[2-(1-cyano-1-methylethyl)diazen-1-yl]-2-methylpropanenitrile, alpha, alpha’-azobisisobutyronitrile, alpha,alpha’-azobis isobutyronitrile, alpha,alpha’-azobis-isobutyronitrile, alpha,alpha-azo bis isobutyronitrile, AMY25782, BCP09376, NSC68042, Tox21_202084, Tox21_303177, 2,2′-azobis(2-methylpropannitrile), AB8084, alpha,alpha’-azo-bis-isobutyronitrile, alpha,alpha’-azobis(isobutyronitrile), STL299672, (E)-(NCC(CH3)2)2N2, 2,2′-azobis(2-methylproprionitrile), Alpha,alpha’-azo-di-iso-butyronitrile, N,N’-Bis(2-cyano-2-propyl)diazene, 2,2′-azo-bis(2-methylpropionitrile), 2,2′-azobis(2′-methylpropionitrile), 2,2′-azobis(2-methyl-propionitrile), 2,2′-azobis-(2-methyl-propionitril), AKOS000119967, AKOS025243270, alpha,alpha’-azobis (isobutyronitrile), .alpha.,.alpha.’-Azodiisobutyronitrile, .alpha.,.alpha.-Azobisisobutyronitrile, 2,2′-azobis (2-methylpropanenitrile), 2,2′-azobis(2′-methylproprionitrile), 2,2′-azobis(2-methyl-propanenitrile), 2,2′-azobis(2-methyl-proprionitrile), 2,2′-azobis[2-methyl-]-propanenitrile, 2,2′-azo-bis-(2-methyl-propionitrile), NCGC00164241-01, NCGC00164241-02, NCGC00257087-01, NCGC00259633-01, 2,2′-AZOBISISOBUTYRONITRILE [MI], AS-44876, BP-20358, V-60, 2,2′-AZOBISISOBUTYRONITRILE [HSDB], A0566, Azobisisobutyronitrile, 12 wt. % in acetone, NS00005643, 2,2′-AZOBIS(2-METHYL)-PROPANENITRILE, EN300-17053, .alpha.,.alpha.’-Azodisobutyric acid dinitrile, Azoethane, 1,1′-dimethyl 1,1′-dicarbonitrile, EN300-343540, .alpha.,.alpha.’-Azodiisobutyric acid dinitrile, 2,2′-Azobis(isobutyronitrile), 10% in acetone, Q423679, 2,2′-(1,2-diazenediyl)bis[2-methylpropanenitrile], 2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile), 2,2′-(E)-diazen-1,2-diylbis(2-methylpropanenitrile), 2-[(cyano-dimethyl-methyl)-azo]-2-methyl-propionitrile, F0001-2054, 2,2′-[(1E)-1,2-Diazenediyl]bis[2-methylpropanenitrile], 2,2′-Azobis(2-methylpropionitrile), recrystallized, 99%, 2,2′-Azobis(2-methylpropionitrile), purum, >=98.0% (GC), 2-[(E)-(1-cyano-1-methyl-ethyl)azo]-2-methyl-propanenitrile, 2,2′-Azobis(2-methylpropionitrile), SAJ first grade, >=98.0%, 2,2′-Azobis(2-methylpropionitrile), 99%, purified by recrystallization, 2-[(1E)-2-(1-CYANO-1-METHYLETHYL)DIAZEN-1-YL]-2-METHYLPROPANENITRILE
2,2-Azobisisobutyronitrile is an organic compound with the formula [(CH3)2C(CN)]2N2.
This white powder is soluble in alcohols and common organic solvents but is insoluble in water.
2,2-Azobisisobutyronitrile is often used as a foamer in plastics and rubber and as a radical initiator.
As an azo initiator, radicals resulting from 2,2-Azobisisobutyronitrile have multiple benefits over common organic peroxides.
For example, they do not have oxygenated byproducts or much yellow discoloration.
Additionally, they do not cause too much grafting and therefore are often used when making adhesives, acrylic fibers, detergents, etc.
2,2-Azobisisobutyronitrile is insoluble in water and denser than water.
2,2-Azobisisobutyronitrile is readily ignited by sparks or flames.
2,2-Azobisisobutyronitrile is burns intensely and persistently.
2,2-Azobisisobutyronitrile is used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.
2,2-Azobisisobutyronitrile, with the formula [(CH3)2C(CN)]2N2, is an organic compound that appears as a white powder.
2,2-Azobisisobutyronitrile is soluble in alcohols and common organic solvents but insoluble in water.
2,2-Azobisisobutyronitrile is commonly used as a foaming agent in plastics and rubber and as a radical initiator.
As an azo initiator, 2,2-Azobisisobutyronitrile has several advantages over common organic peroxides.
For example, 2,2-Azobisisobutyronitrile does not produce oxygen-containing byproducts or excessive yellowing.
Additionally, 2,2-Azobisisobutyronitrile causes less crosslinking, making it frequently used in the production of adhesives, acrylic fibers, detergents, and similar products.
2,2-Azobisisobutyronitrile is a chemical compound that has become increasingly popular in various industries.
2,2-Azobisisobutyronitrile is known by many names, including AIBN, Azobis, and V-azo.
2,2-Azobisisobutyronitrile’s chemical formula is C8H12N4, and its CAS number is 78-67-1.
Appearance-wise, 2,2-Azobisisobutyronitrile is a white crystalline powder that is soluble in organic solvents such as ethanol, methanol, and chloroform, but not in water.
2,2-Azobisisobutyronitrile has a melting point of 104-106°C and a density of 1.02-1.03 g/mL.
2,2-Azobisisobutyronitrile has become quite essential in various industries such as polymer production, pharmaceuticals, and cosmetics.
2,2-Azobisisobutyronitrile is used as a polymerization initiator in the production of plastics, resins, and rubbers.
2,2-Azobisisobutyronitrile is also known for its use in radical reactions and organic synthesis. In the medical industry, 2,2-Azobisisobutyronitrile is used to produce bone cements and in dental applications.
2,2-Azobisisobutyronitrile is also used in the cosmetics industry as a polymerization initiator for hair dyes.
When it comes to packaging, 2,2-Azobisisobutyronitrile should be stored in a cool, dry place in tightly sealed containers to prevent contamination.
During transportation, 2,2-Azobisisobutyronitrile should be kept away from heat, sources of ignition, moisture, and direct sunlight.
The manufacture of 2,2-Azobisisobutyronitrile begins with the reaction of sodium nitrite and isobutyronitrile.
The resultant solution is then cooled to the optimal temperature range of 0-5℃.
After filtration, the solid product is then washed with anhydrous ethanol and dried to obtain the final product.
In conclusion, 2,2-Azobisisobutyronitrile is an important chemical compound that has various uses in different industries.
2,2-Azobisisobutyronitrile is easily accessible and can be synthesized using simple procedures.
However, 2,2-Azobisisobutyronitrile should be handled with care due to its flammability and toxicity.
2,2-Azobisisobutyronitrile is important to follow all guidelines and regulations while handling and storing 2,2-Azobisisobutyronitrile.
2,2-Azobisisobutyronitrile is the most well-known azo initiator, which is easy and safe to use as a catalyst for free radical polymerization in the operating temperature range of 45-90 ºC, which is the main criterion for controlling polymerization reactions (Initiator for (co)polymerization of styrene, vinyl chloride, vinylidene chloride , acrylonitrile, acrylates and methacrylates.).
2,2-Azobisisobutyronitrile have low molecular mass.
And freedom from side reactions, 2,2-Azobisisobutyronitrile is more efficient and economical for controlled polymerizations at low concentrations.
The presence of additives does not affect 2,2-Azobisisobutyronitrile’s rate of decomposition into free radicals.
2,2-Azobisisobutyronitrile does not cause oxidative degradation and discoloration, generally associated with peroxides.
This allows even transparent polymers to maintain their physical properties.
2,2-Azobisisobutyronitrile is an organic compound with the formula [(CH3)2C(CN)]2N2.
This white powder is soluble in alcohols and common organic solvents but is insoluble in water.
Uses of 2,2-Azobisisobutyronitrile:
2,2-Azobisisobutyronitrile is maily used as polymerization initiator of monomer such as chloroethylene,vinyl acetate,acrylonitrile,etc.
2,2-Azobisisobutyronitrile is also used as blowing agent for PVC, polyalkene,polyurethane, polyvinyl alcohol, acrylonitrile/butadiene copolymer, chloroethylene copolymer, acrylonitrile/ butadiene/styrene copolymer, polyisocyanate, polyvinyl acetate, polyamide and polyester, etc
Moreover, 2,2-Azobisisobutyronitrile is also used in other organic synthesis.
2,2-Azobisisobutyronitrile is used as polymerization initiator of monomers such as polyvinyl chlorida, polyvinyl alcohol,polystyrene and polyacrylonitrila.
2,2-Azobisisobutyronitrile is used as initiator for polymerization of vinyl chlorida acrylonitrila and other monomers, and also as foaming agent for rubber and plastics.
2,2-Azobisisobutyronitrile can also be used as vulcanizing agent, pesticide and intermediate of organic synthesis.
2,2-Azobisisobutyronitrile is used as blowing agent (elastomers and plastics), catalyst (vinyl polymerizations), curing agent (unsaturated polyester resins), and fumigant (when heated)
2,2-Azobisisobutyronitrile is used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.
2,2-Azobisisobutyronitrile is used as an initiator in the polymerization of monomers such as vinyl chloride, vinyl acetate and acrylonitrile, and the amount thereof is 04% to 0.2%.
2,2-Azobisisobutyronitrile is also can be used as polyvinyl chloride, polyurethane, polyvinyl alcohol, acrylonitrile and butadiene copolymer rubber, plastic foaming agent.
2,2-Azobisisobutyronitrile is also useful as sulfides, pesticides, and intermediates in organic synthesis.
2,2-Azobisisobutyronitrile is used as an initiator for the polymerization of vinyl chloride, vinyl acetate, acrylonitrile and other monomers, as well as a foaming agent for rubber and plastics, the dosage is 10% ~ 20%.
2,2-Azobisisobutyronitrile can also be used as a curing agent, pesticide and organic synthesis intermediates.
2,2-Azobisisobutyronitrile is used as polyvinyl chloride, polyvinyl alcohol, polystyrene, polymerization initiator of monomer such as polyacrylonitrile organic synthesis intermediate.
2,2-Azobisisobutyronitrile is used as initiator for high molecular polymer.
2,2-Azobisisobutyronitrile is used as initiator for polymerization or copolymerization of vinyl acetate and acrylate.
2,2-Azobisisobutyronitrile may also be used as a blowing agent.
2,2-Azobisisobutyronitrile is mainly used as vinyl chloride, vinyl acetate, acrylonitrile monomer polymerization initiator.
2,2-Azobisisobutyronitrile can also be used as a foaming agent of polyvinyl chloride, polyolefin, Polyurethane, polyvinyl alcohol, vinyl chloride and butadiene copolymer, vinyl chloride copolymer, acrylonitrile and butadiene and styrene copolymer, polyisocyanate, polyvinyl acetate, polyamide and polyester.
In addition, 2,2-Azobisisobutyronitrile can be used for other organic synthesis.
2,2-Azobisisobutyronitrile is used in polymerization of monomers like vinyl chloride, vinyl acetate, ethylene, styrene, methyl methacrylate, etc.
2,2-Azobisisobutyronitrile is used as chemical blowing agent for section rigid PVC foams when the processing temperature range is 100-120 ºC.
2,2-Azobisisobutyronitrile is used as initiator in manufacture of nytron fibre.
2,2-Azobisisobutyronitrile is used for initiating of process of chlorination of dichloroethane.
2,2-Azobisisobutyronitrile is used in silicone foam and rubber foam applications
2,2-Azobisisobutyronitrile is used in the manufacture of acrylic sheet, bangles, tubes, rods etc.
2,2-Azobisisobutyronitrile is used as a low temperature blowing agent for making cellular plastics.
2,2-Azobisisobutyronitrile is used in the manufacture of acrylic resins.
2,2-Azobisisobutyronitrile is used in water treatment.
Hair making:
The condensation reaction of hydrazine hydrate with acetone at reflux temperature was carried out to produce an azine (acetone containing nitrogen).
Hydrogen cyanide gas is obtained by reacting 70% Sulfuric acid with 25% ~ 30% sodium cyanide.
Then, the obtained hydrogen cyanide gas was reacted with an azine (acetone-nitrogen) at 55 ~ 60°C, and then cooled to continue the reaction to obtain diisobutyronitrile hydrazine.
Diisobutyronitrile hydrazine is reacted with nitrogen at 20°C.
Lower, and then precipitated and filtered, the filtrate is recovered and used, the filter cake is washed with water, and fine azobisisobutyronitrile is obtained after removing water.
Crude azobisisobutyronitrile is dissolved with ethanol and filtered, the filtrate is crystallized at low temperature, vacuum filtered and dried at low temperature to obtain the final product.
Industry Uses:
Propellants and blowing agents
Polymerization promoter
Process regulators
Intermediate
Flame retardants
Consumer Uses:
Photosensitive chemicals
Other
Applications of 2,2-Azobisisobutyronitrile:
2,2-Azobisisobutyronitrile is maily used as polymerization initiator of monomer such as chloroethylene,vinyl acetate,acrylonitrile,etc.
2,2-Azobisisobutyronitrile is also used as blowing agentfor PVC,polyalkene,polyurethane,polyvinyl alcohol,acrylonitrile/butadiene copolymer,chloroethylene copolymer,acrylonitrile/ butadiene/styrene copolymer,polyisocyanate,polyvinyl acetate,polyamide and polyester,etc.
Moreover, 2,2-Azobisisobutyronitrile is also used in other organic synthesis.
2,2-Azobisisobutyronitrile can be used as an initiator in the preparation of:
Polystyrene by soap-free emulsion polymerization.
Molecularly imprinted polymer(MIP) using 1-vinyl imidazole.
MIP can be used to quantify acid violet 19 dye in river water samples.
2,2-Azobisisobutyronitrile is a well-known azo initiator used as a catalyst for free radical polymerization.
2,2-Azobisisobutyronitrile’s applications include:
Polymerization of monomers such as vinyl chloride, vinyl acetate, ethylene, styrene, and methyl methacrylate.
Chemical foaming agent for rigid PVC foams at processing temperatures of 100-120 ºC.
Initiator in the production of nitron fibers.
Initiator for the chlorination of dichloroethane.
Applications in silicone and rubber foams.
Manufacturing of acrylic sheets, bracelets, tubes, rods, etc.
Foaming agent for cellular plastics at low temperatures.
Production of acrylic resins.
Water purification processes.
Nature of 2,2-Azobisisobutyronitrile:
2,2-Azobisisobutyronitrile is white needle-like crystals, low purity white powder crystals.
2,2-Azobisisobutyronitrile is insoluble in water, soluble in methanol, ethanol, acetone, ether, petroleum ether, toluene, aniline and other organic solvents.
When 2,2-Azobisisobutyronitrile is mixed with high heat, open flame or oxidant, there is a risk of combustion and explosion caused by friction and impact.
During the combustion of 2,2-Azobisisobutyronitrile, toxic gases are emitted.
When 2,2-Azobisisobutyronitrile is heated, nature is unstable, 40 degrees Celsius will slowly decompose, release nitrogen and organic cyanide compounds that are harmful to the human body, and emit a large amount of heat, may cause an explosion.
Production Method of 2,2-Azobisisobutyronitrile:
with acetone, hydrazine hydrate and sodium cyanide as raw materials: the above condensation reaction temperature is 55~60 ℃, the reaction time was 5h, and then cooled to 25~30 C for 2H.
When the temperature was lowered to below 10 °c, chlorine was started, and the reaction was carried out below 20 °c.
The material ratio was:
HCN: acetone: hydrazine = 1L: 1.5036kg: 0.415kg.
Acetone cyanohydrin and hydrazine hydrate were used for reaction, and then liquid chlorine oxidation or sodium hypochlorite oxidation with aminobutyronitrile.
Chemical Reactions of 2,2-Azobisisobutyronitrile:
These radicals formed by the decomposition of 2,2-Azobisisobutyronitrile can initiate free-radical polymerizations and other radical-induced reactions.
For instance, a mixture of styrene and maleic anhydride in toluene will react if heated, forming the copolymer upon addition of 2,2-Azobisisobutyronitrile.
Another example of a radical reaction that can be initiated by 2,2-Azobisisobutyronitrile is the anti-Markovnikov hydrohalogenation of alkenes.
2,2-Azobisisobutyronitrile has also been used as the radical initiator for Wohl–Ziegler bromination.
The 2,2-Azobisisobutyronitrile-derived 2-cyano-2-propyl radical abstracts the hydrogen from tributyltin hydride.
The resulting tributyltin radical can be used for removal of a bromine atom.
2,2-Azobisisobutyronitrile-derived radicals abstract a hydrogen from HBr to give a bromine radical, which can add to alkenes.
This type of hydrohalogenation of an alkene proceeds with anti-Markovnikov selectivity.
Decomposition Mechanism of 2,2-Azobisisobutyronitrile:
In its most characteristic reaction, 2,2-Azobisisobutyronitrile decomposes, eliminating a molecule of nitrogen gas to form two 2-cyanoprop-2-yl radicals.
Because 2,2-Azobisisobutyronitrile readily gives off free radicals, 2,2-Azobisisobutyronitrile is often used as a radical initiator.
This happens at temperatures above 40 °C, but in experiments is more commonly done at temperatures between 66 °C and 72 °C.
This decomposition has a ΔG‡ of 131 kJ/mol and results in two 2-cyano-2-propyl (carbon) radicals and a molecule of nitrogen gas.
The release of nitrogen gas pushes this decomposition forward due to the increase in entropy.
And the 2-cyano-2-propyl radical is stabilized by the −CN group.
Production and Analogues of 2,2-Azobisisobutyronitrile:
2,2-Azobisisobutyronitrile is produced in two steps from acetone cyanohydrin.
Reaction with hydrazine gives the substituted dialkylhydrazine.
In the second step, the hydrazine is oxidized to the azo derivative:
2 (CH3)2C(CN)OH + N2H4 → [(CH3)2C(CN)]2N2H2 + 2 H2O
[(CH3)2C(CN)]2N2H2 + Cl2 → [(CH3)2C(CN)]2N2 + 2 HCl
Related azo compounds behave similarly, such as 1,1′-azobis(cyclohexanecarbonitrile).
Water-soluble azo initiators are also available.
Handling and Storage of 2,2-Azobisisobutyronitrile:
Precautions for safe handling:
NO open flames, NO sparks and NO smoking.
Do NOT expose to friction or shock.
Closed system, dust explosion-proof electrical equipment and lighting.
Prevent deposition of dust.
Prevent build-up of electrostatic charges (e.g., by grounding).
Handling in a well ventilated place.
Wear suitable protective clothing.
Avoid contact with skin and eyes.
Avoid formation of dust and aerosols.
Use non-sparking tools.
Prevent fire caused by electrostatic discharge steam.
Conditions for safe storage, including any incompatibilities:
Separated from strong oxidants and incompatible materials.
Stability and Reactivity of 2,2-Azobisisobutyronitrile:
Reactivity:
Decomposes on warming.
This produces toxic fumes of tetramethylsuccinonitrile and cyanide.
May decompose explosively on shock, friction or concussion.
May explode on heating.
Reacts violently with alcohols, oxidants, ketones such as acetone, aldehydes and hydrocarbons such as heptane.
This generates fire and explosion hazard.
Chemical stability:
no data available
Possibility of hazardous reactions:
If dry, 2,2-Azobisisobutyronitrile can be charged electrostatically by swirling, pneumatic transport, pouring, etc.
Self-decomposition or self-ignition may be triggered by heat, chemical reaction, friction or impact.
Self-accelerating decomposition may occur if the specific control temperature is not maintained.
These materials are particularly sensitive to temperature rises.
2,2-Azobisisobutyronitrile is an azo compound.
Azo, diazo, azido compounds can detonate.
This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids.
Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents.
Flammable gases are formed by mixing materials in this group with alkali metals.
Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.
Conditions to avoid:
no data available
Incompatible materials:
no data available
Hazardous decomposition products:
no data available
Safety of 2,2-Azobisisobutyronitrile:
2,2-Azobisisobutyronitrile is safer to use than benzoyl peroxide (another radical initiator) because the risk of explosion is far less.
However, 2,2-Azobisisobutyronitrile is still considered as an explosive compound, decomposing above 65 °C.
A respirator dust mask, protective gloves and safety glasses are recommended.
Pyrolysis of 2,2-Azobisisobutyronitrile without a trap for the formed 2-cyanopropyl radicals results in the formation of tetramethylsuccinonitrile, which is highly toxic.
First-Aid Measures of 2,2-Azobisisobutyronitrile:
If inhaled:
Fresh air, rest.
Refer for medical attention.
Following skin contact:
Remove contaminated clothes.
Rinse skin with plenty of water or shower.
Following eye contact:
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Following ingestion:
Induce vomiting (ONLY IN CONSCIOUS PERSONS!).
Give a slurry of activated charcoal in water to drink.
Refer for medical attention.
Most important symptoms/effects, acute and delayed:
Inhalation or contact with vapors, substance or decomposition products may cause severe injury or death.
May produce irritating, toxic and/or corrosive gases.
Runoff from fire control may cause pollution.
Indication of immediate medical attention and special treatment needed, if necessary:
no data available
Fire-Fighting Measures of 2,2-Azobisisobutyronitrile:
Suitable extinguishing media:
The temperature of 2,2-Azobisisobutyronitrile must be maintained at or below the “Control Temperature” at all times.
SMALL FIRE:
Dry chemical, CO2, water spray or regular foam.
LARGE FIRE:
Flood fire area with water from a distance.
Move containers from fire area if you can do 2,2-Azobisisobutyronitrile without risk.
FIRE INVOLVING TANKS OR CAR/TRAILER LOADS:
BEWARE OF POSSIBLE CONTAINER EXPLOSION.
Fight fire from maximum distance or use unmanned hose holders or monitor nozzles.
Cool containers with flooding quantities of water until well after fire is out.
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.
ALWAYS stay away from tanks engulfed in fire.
Specific hazards arising from the chemical:
Self-decomposition, self-polymerization, or self-ignition may be triggered by heat, chemical reaction, friction or impact.
Self-accelerating decomposition may occur if the specific control temperature is not maintained.
These materials are particularly sensitive to temperature rises.
Above a given “Control Temperature” they decompose or polymerize violently and may catch fire.
May be ignited by heat, sparks or flames.
Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.
Some may decompose explosively when heated or involved in a fire.
2,2-Azobisisobutyronitrile may burn violently.
Decomposition or polymerization may be self-accelerating and produce large amounts of gases.
Vapors or dust may form explosive mixtures with air.
Special protective actions for fire-fighters:
Use water in large amounts, water spray.
In case of fire:
Keep drums, etc., cool by spraying with water.
Accidental Release Measures of 2,2-Azobisisobutyronitrile:
Personal precautions, protective equipment and emergency procedures:
Consult an expert! Personal protection:
Filter respirator for organic gases and particulates adapted to the airborne concentration of 2,2-Azobisisobutyronitrile.
Do NOT let this chemical enter the environment.
Remove all ignition sources.
Sweep spilled substance into covered containers.
If appropriate, moisten first to prevent dusting.
Methods and materials for containment and cleaning up:
Collect and arrange disposal.
Keep the chemical in suitable and closed containers for disposal.
Remove all sources of ignition.
Use spark-proof tools and explosion-proof equipment.
Adhered or collected material should be promptly disposed of, in accordance with appropriate laws and regulations.
Exposure Controls/Personal Protection of 2,2-Azobisisobutyronitrile:
Occupational Exposure limit values:
no data available
Biological limit values:
no data available
Appropriate engineering controls:
Ensure adequate ventilation.
Handle in accordance with good industrial hygiene and safety practice.
Set up emergency exits and the risk-elimination area.
Individual protection measures, such as personal protective equipment:
Eye/face protection:
Wear safety goggles or eye protection in combination with breathing protection.
Skin protection
Protective gloves.
Respiratory protection
Use local exhaust or breathing protection.
Thermal hazards
no data available
Identifiers of 2,2-Azobisisobutyronitrile:
HSN Code: 29269000
IMDG Identification: Restricted for export from India
Molecular Formula: C8H12N4
Molecular Weight: 164.21
Storage: 2 to 8°C (Refrigerate)
Shelf Life: 60 Months
Linear Formula: (CH3)2C(CN)N=NC(CH3)2CN
CAS Number: 78-67-1
Molecular Weight: 164.21
EC Number: 201-132-3
CAS Number: 78-67-1
Abbreviations: AIBN
ChemSpider: 6299
ECHA InfoCard: 100.001.030
EC Number: 201-132-3
PubChem CID: 6547
RTECS number: UG0800000
UNII: FZ6PX8U5YB
UN number: 3234 1325
CompTox Dashboard (EPA): DTXSID70859108 DTXSID1026457, DTXSID70859108
InChI:
InChI=1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
Key: OZAIFHULBGXAKX-VAWYXSNFSA-N
InChI=1/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
Key: OZAIFHULBGXAKX-VAWYXSNFBT
SMILES: CC(C)(C#N)/N=N/C(C)(C)C#N
Properties of 2,2-Azobisisobutyronitrile:
Chemical formula: C8H12N4
Molar mass: 164.21 g/mol
Appearance: white crystals
Density: 1.1 g cm−3
Melting point: 103 to 105 °C (217 to 221 °F; 376 to 378 K)
Solubility in water: poor
Quality Level: 200
Assay: 98%
form: powder
mp: 102-104 °C (dec.) (lit.)
storage temp.: 2-8°C
SMILES string: CC(C)(N=NC(C)(C)C#N)C#N
InChI: 1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
InChI key: OZAIFHULBGXAKX-VAWYXSNFSA-N
Molecular Weight: 164.21 g/mol
XLogP3-AA: 1.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 164.106196400 g/mol
Monoisotopic Mass: 164.106196400 g/mol
Topological Polar Surface Area: 72.3Ų
Heavy Atom Count: 12
Complexity: 251
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of 2,2-Azobisisobutyronitrile:
Appearance (Colour): White
Appearance (Form): Compound/ powder
Assay (ex N): min. 98%
Melting Point: 102 – 104°C
Appearance (Colour): White
Appearance (Form): Compound/ powder
Assay (ex N): min. 98%
Melting Point: 102 – 104°C
Names of 2,2-Azobisisobutyronitrile:
IUPAC names:
2,2′-Azobis(2-methylpropionitrile)
2-(azo(1-cyano-1-methylethyl))-2-methylpropane nitrile
Other names:
Azobisisobutyronitrile
AIBN