AZOBISISOBUTYRONITRILE

PRODUCT IDENTIFICATION
CAS NO. 78-67-1

AZOBISISOBUTYRONITRILE
EINECS NO. 201-132-3
FORMULA (CH3)2C(CN)N=NC(CH3)2CN
MOL WT. 164.21
H.S. CODE 2927.00
TOXICITY Oral rat LD50: 100 mg/kg
SYNONYMS 2,2'-Azobis(2-methylpropionitrile);
2,2'-Azobis[2-methylpropanenitrile]; AIBN; alpha,alpha'-Azodiisobutyronitrile; 2,2'-Dicyano-2,2'-azopropane; 2,2'-azo-bis(isobutyronitrile); 2,2'-Dimethyl-2,2'- azodipropionitrile; Azodiisobutyrodinitrile; 2,2[-Azobis(2-methylpropionitrile); 
SMILES

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE white to off-white powder
MELTING POINT Decomposes
BOILING POINT  
SPECIFIC GRAVITY

1.1
SOLUBILITY IN WATER Insoluble (Soluble in alcohol)
AUTOIGNITION 64 C
VAPOR DENSITY 5.7

NFPA RATINGS

 

REFRACTIVE INDEX

 
FLASH POINT

 
STABILITY Unstable (shock sensitive, explosive decomposition by acetone, thermally unstable)

APPLICATIONS
Azo is the prefix for the group -N=N- or a combining form of azote which share the core azobenzene structure. Azo compounds have a general molecular formula of R-N=N-R', where R is aryl, heteroaryl, -CH=C(OH)- or aliphatic. The extended delocalization of electrons in the benzene and azo groups forms a conjugated system absorbing visible frequencies of light. Aromatic groups provide characteristic colors of red, orange, and yellow. This is the fundamental structure of azo dyes. Aliphatic azo compounds are unstable and the loss of nitrogen gas occurs by the simultaneous cleavage of carbon-nitrogen bonds, resulting in carbon-centered radicals. some aliphatic azo compounds are utilized as radical initiators. Azobisisobutyronitrile is used as an initiator of free radical reactions for the production of polymer (polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers) and as a blowing agent for plastics and elastomers.

Some Azocompound initiators include:

  • 2,2'-Azobis(2-methylpropionamidine) dihydrochloride  (CAS #: 2997-92-4)
  • 2,2'-Azobis(2-methylpropionitrile) (CAS #: 78-67-1)
  • 2,2'-Azobis(2-methylbutanenitrile) (CAS #: 13472-08-7)
  • 4,4'-Azobis(4-cyanovaleric acid) (CAS #: 2638-94-0)
  • 2,2'-Azobis(2,4-dimethylvaleronitrile) (CAS #: 4419-11-8)
  • 1,1'-Azobis(cyanocyclohexane) (CAS #: 2094-98-6)
  • 4,4'-Azobis(4-cyanovaleric Acid) (CAS #: 2638-94-0)
  • 1,1'-Azobis(N,N-dimethylformamide) (CAS #: 10465-78-8)
  • 2,2'-Azobis(4-methoxy-2,4-dimethylvaleronitrile) (CAS #: 15545-97-8)
  • 2,2'-Azobis(2-methylbutyronitrile) (CAS #: 13472-08-7)
  • 2,2'-Azobis(2,4,4-trimethylpentane) (CAS #: 39148-34-0)
Polymerization is initiated generally by free radical. There are four types of free radical initiators which initiate polymerization.
  • Peroxides including hydroperoxides (tertiary-butyl hydroperoxide, benzoylperoxide)
  • Azocompound thermal initiators (azoisobutyronitrile)
  • Redoxinitiators (mixture of iron(III) acetylacetonate): free radicals are formed by one-electron transferreactions. Useful in low temperature and emulsion polymerization
  • Photoinitiators (benzoin, benzil dimethylketal)
SALES SPECIFICATION

APPEARANCE

 white to off-white crystal or crystalline powder
PURITY

98.0% min

INSOLUBLES

0.01% max (in EtOH)

VOLATILES

1.0% max
TRANSPORTATION
PACKING 20kgs in bag
HAZARD CLASS 4.1
UN NO. 3242
OTHER INFORMATION
Nitrile is an organic compounds containing cyano group (-C》N, containing trivalent nitrogen) which is attached to one carbon atom with the general formula RC》N. Their names are corresponding to carboxylic acids by changing '-ic acid' to the suffix, '-onitrile' which denotes only the 》N atom (triply bound) excluding the carbon atom attached to it, or  the suffix, '-carbonitrile' where the carbon atom in the -CN is included, whichever preserves a single letter O. Examples are acetonitrile from acetic acid and benzonitrile from benzoic acid. The prefix,  'cyano-' is used as an alternative naming system to indicate the presence of a nitrile group in a molecule for the compounds of salts and organic derivatives of hydrogen cyanide (HC》N). Isocyanides are salts and hydrocarbyl derivatives from the isomer, HN+》C-. Sodium cyanide, NaCN; potassium cyanide, KCN; calcium cyanide, Ca(CN)2; and hydrocyanic (or prussic) acid, HCN are examples. Chemically, the simple inorganic cyanides resemble chlorides in many ways. Organic nitriles act as solvents and are reacted further for various application including;

  · Extraction solvent for fatty acids, oils and unsaturated hydrocarbons
  · Solvent for spinning and casting and extractive distillation based on its     selective miscibility with organic compounds.
  · Removing agent of colouring matters and aromatic alcohols
  · Non-aqueous solvent for titrations and for inorganic salts
  · Recrystallization of steroids
  · Parent compound for organic synthesis
  · Solvent or chemical intermediate in biochemistry (protein sequencing and DNA synthesis)
  · High-pressure liquid chromatographic analysis
  · Catalyst and component of transition-metal complex catalysts
  · Stabilizer for chlorinated solvents
  · Chemical intermediate and solvent for perfumes and pharmaceuticals