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2,2'-Azobis(2-methylpropionitrile)

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2,2'-Azobis(2-methylpropionitrile) Basic information
Recrystallization Temperature of initiator Chemical properties Uses Production method category Toxicity grading Acute toxicity Explosive hazardous characteristics Flammability hazard characteristics Storage characteristics Extinguishing agent
Product Name:2,2'-Azobis(2-methylpropionitrile)
Synonyms:A,A'-AZOISOBUTYRONITRILE;AIBN;ALPHA,ALPHA'-AZOBISISOBUTYRONITRILE;ALPHA,ALPHA-AZOBISISOBUTYRONITRILE;ALPHA,ALPHA'-AZO-DI-ISO-BUTYRONITRILE;ALPHA,ALPHA'-AZOISOBUTYRONITRILE;2,2'-dicyano-2,2'-azopropane;2,2'-Dimethyl-2,2'-azodipropionitrile
CAS:78-67-1
MF:C8H12N4
MW:164.21
EINECS:201-132-3
Product Categories:Free Radical Initiators;Organics;pharmacetical
Mol File:78-67-1.mol
2,2'-Azobis(2-methylpropionitrile) Structure
2,2'-Azobis(2-methylpropionitrile) Chemical Properties
mp 102-104 °C (dec.)(lit.)
density 1.11
storage temp. 2-8°C
Water Solubility Insoluble
Merck 13,920
Stability:Stability Flammable solid. Shock sensitive. Thermally unstable. May be explosive in combination with acetone or heptane. Incompatible with oxidizing agents.
CAS DataBase Reference78-67-1(CAS DataBase Reference)
NIST Chemistry Reference2,2'-Azo-bis-isobutyronitrile(78-67-1)
EPA Substance Registry SystemPropanenitrile, 2,2'-azobis[2-methyl- (78-67-1)
Safety Information
Hazard Codes E,Xn,F,Xi
Risk Statements 2-11-20/22-52/53-67-65-48/20-38-63-66-36
Safety Statements 39-41-47-61-62-36/37-16-26
RIDADR UN 3234 4.1
WGK Germany 2
RTECS UG0800000
4.4
HazardClass 4.1
PackingGroup II
Hazardous Substances Data78-67-1(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Azodiisobutyrodinitrile English
ACROS English
SigmaAldrich English
2,2'-Azobis(2-methylpropionitrile) Usage And Synthesis
Recrystallization1, recrystallize twice a chemically pure 2,2'-Azobis(2-methylpropionitrile) with methanol (by 1:12) and air-dry in a ventilated dark overnight, then place in a vacuum oven with phosphorus pentoxide as a desiccant, vacuum degree 1.013 * 105Pa, under reduced pressure, and dry to 24h.Refined 2,2'-Azobis(2-methylpropionitrile) needs to be put in the colored jar, sealed and kept in cold dark place.
2, add 50ml 95% alcohol into 150ml Erlenmeyer flask equipped with a reflux condenser , heat in a water bath to near boiling, quickly add 5gAIBN, shak to make it be completely dissolved (boiling time not too long, if too long, severe decomposition ), filter hot solution rapidly ( the funnel and filter flask using for filter must be warmed) and cool the filtrate to give white crystals, dry in a vacuum desiccator, a melting point of 102℃, store the product in a brown bottle, cryopreservation.
Temperature of initiator2,2'-Azobis(2-methylpropionitrile) is a particularly excellent free radical initiator , nitrogen will be released by the decomposition when it is heated to about 70 ° C and free radicals (CH3) 2CCN is generated which is affected by cyano radical , more stable. It can react with other organic substrates, and then generates a new radical in annihilation of itself , causing chain reaction of free radicals (see radical reaction). At the same time, it can also be two coupled molecules, generating highly toxic tetramethoxysilane succinonitrile (TMSN).
AIBN melts when heated to 100 ~ 107 ° C and dramaticly decomposes, releases nitrogen and several organic nitrile compound toxic to humans, and may cause an explosion, fire. Slowly decomposes at room temperature, and it should be stored at 10 ° C or less. Away from fire, heat source. poisonous. Metabolizes into hydrocyanic acid in the blood, liver, brain and other tissues of animals.
The above information is edited by the Chemicalbook of Tian Ye.
Chemical propertiesWhite columnar crystals or white crystalline powder. Insoluble in water, soluble in methanol, ethanol, acetone, ether, petroleum ether and aniline and other organic solvents.
UsesThe polymerization initiator for Vinyl chloride, vinyl acetate, acrylonitrile and blowing agent for rubber, plastic , in an amount of 10% to 20%.
This product can also be used as curing agents, pesticides and organic synthesis intermediates.
This product is a highly toxic substance, mice are orally LD5017.2 ~ 25mg / kg, the organic cyanide released by the decomposition when it is heated has a greater poison on the human body .
Production methodAcetone, hydrazine hydrate and sodium cyanide as raw materials:
The temperature of condensation reaction above is 55 ~ 60 ℃, reaction time is 5h, and then cool down to 25 ~ 30 ℃ ,time is 2h. When to be cooled to below 10 ℃,begin to flow chlorine and carry out the reaction at below 20 ℃.
Ratio of material: HCN: acetone: hydrazine = 1L:1.5036kg:0.415kg.
Acetone cyanide alcohol and hydrazine hydrate react, and then the use of chlorine oxidation or amino nitrile with sodium hypochlorite oxidation.
categoryFlammable solids
Toxicity gradingMiddle toxic
Acute toxicityOral - rat LDL0: 670 mg / kg; Oral - Mouse LD50: 700 mg / kg
Explosive hazardous characteristicsExplosive when mixed with oxidants ; easily oxidized, unstable and intense heat decomposition, explosive when heated with heptane, acetone
Flammability hazard characteristicsFlammable in case of fire, high temperature, oxidant ; decomposition and generating combustible gas in case of thermal ; combustion produces toxic fumes of nitrogen oxides
Storage characteristicsTreasury ventilation low-temperature drying; and separated from oxidants
Chemical Propertieswhite solid
UsageUsed as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers. 1 Used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA). 2
Extinguishing agentWater, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent
General DescriptionInsoluble in water and denser than water. Moderately toxic by ingestion. Readily ignited by sparks or flames. Burns intensely and persistently. Toxic oxides of nitrogen produced during combustion. Used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.
Air & Water ReactionsDust may form an explosive mixture in air. Insoluble in water.
Reactivity ProfileSelf-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'-Azobis(2-methylpropionitrile) 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.
2,2'-Azobis(2-methylpropionitrile) Preparation Products And Raw materials
Raw materialsAcetone-->Chlorine-->Hydrazinium hydroxide-->Sodium cyanide-->Sodium hypochlorite-->Acetone cyanohydrin -->BUTYRONITRILE
Preparation Products4-(PYRROLIDIN-1-YLMETHYL)BENZENEBORONIC ACID, PINACOL ESTER 97%1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]PYRROLIDINE-->4-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->2,1,3-Benzothiadiazole-5-carbaldehyde-->3-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->4-(PIPERIDINE-1-CARBONYL)PHENYLBORONIC ACID-->2,1,3-Benzothiadiazol-5-ylmethanol-->3-(PIPERIDINOMETHYL)BENZALDEHYDE-->4-(1,2,3-THIADIAZOL-4-YL)BENZYLAMINE HYDROCHLORIDE-->3-PHENOXYPHENYLACETONITRILE-->2,6-Dichlorobenzaldehyde-->5-Dibenzosuberenone-->2-Chlorobenzyl chloride-->4-(1,2,3-THIADIAZOL-4-YL)BENZALDEHYDE-->3-QUINOLIN-2-YLPROPANOIC ACID-->Dichloroacetyl chloride-->Dicofol-->4-Benzofurazancarboxaldehyde-->2-(DIPHENYLPHOSPHINO)ETHYLTRIETHOXYSILANE-->5-(BROMOMETHYL)-2,1,3-BENZOTHIADIAZOLE-->11b,21-Dihydroxy-2'-methyl-5'bH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 21-acetate-->Dideoxyinosine-->graft copolymer PAA-G-PIPA microsphere-->2-(Bromomethyl)benzoic acid-->2-TRIFLUOROMETHYLQUINOLINE-7-CARBOXYLIC ACID-->4-[4-(BROMOMETHYL)PHENYL]-1,2,3-THIADIAZOLE-->3-CHLORO-4-((CYCLOPROPYLAMINO)METHYL)BENZALDEHYDE-->METHYL ALPHA-BROMO-2-CHLOROPHENYLACETATE-->Maleic acid-allyl alcohol copolymer-->11-Bromoundecanoic acid-->1-(3-CHLORO-4-((CYCLOPROPYLAMINO)METHYL)PHENYL)ETHANONE-->2,4-Dichlorobenzyl chloride-->super absorbent resin synthesized by microwave cation ion radiation-->3,7-dichloro-8-dichloro methyl quinoline-->METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE-->dimethylacrolyl phenoxy propanestyrene copolymer optical plastics-->2-Nitroacetophenone-->amphoteric super absorbent resin synthesized by microwave radiation-->2-Nitrobenzyl bromide
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