78-67-1

Basic information

• 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 NO: 78-67-1
• Molecular Formula: C₈H₁₂N₄
• Molecular Weight: 164.21
• EINECS: 201-132-3
• Product Categories: Free Radical Initiators;Organics;pharmacetical
• Mol File: 78-67-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 102-104 °C (dec.)(lit.)
• Boiling Point: 281.68°C (rough estimate)
• Flash Point: 4℃
• Appearance: white solid
• Density: 1.11
• Vapor Pressure: 0.81Pa at 24.85℃
• Refractive Index: n20/D1.495
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble
• Stability: Stability Flammable solid. Shock sensitive. Thermally unstable. May be explosive in combination with acetone or heptane. Incompa
• Merck: 13,920
• BRN: 1708400
• CAS DataBase Reference: 2,2'-Azobis(2-methylpropionitrile)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Azobis(2-methylpropionitrile)(78-67-1)
• EPA Substance Registry System: 2,2'-Azobis(2-methylpropionitrile)(78-67-1)

Safety Data

• Hazard Codes: E,Xn,F,Xi
• 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
• F: 4.4
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 78-67-1(Hazardous Substances Data)

Usage

Description

Azobisisobutyronitrile (abbreviated AIBN) 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. It is often used as a foamer in plastics and rubber and as a radical initiator. It's soluble in a wide variety of organic solvents, including alcohol-based solvents. Insoluble 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.

Uses

Different sources of media describe the Uses of 78-67-1 differently. You can refer to the following data:
1. 2,2'-Azobis(2-methylpropionitrile) is used as an initiator in polymer radical polymerization because its molecules can easily undergo split reactions and form molecules with high activation energy. 2,2'-Azobis(2-methylpropionitrile) (AIBN) is the most commonly used azo initiator. Its characteristic is that the decomposition reaction is relatively stable, only one kind of free radical is generated, and basically no induced decomposition occurs, so it is often used in the kinetics research of free radical polymerization.
2. Azobisisobutyronitrile (AIBN) is an azo-compound and is widely used as a free radical initiator. This compound has labile carbon-nitrogen covalent bond which undergoes homolytic scission under thermal, chemical or photochemical conditions producing free radicals. They are useful in many reactions like halogenation, polymerisation of vinyl monomers, grafting reactions, curing of rubbers and unsaturated polymers and cross-linking of polyolefins. AIBN can be used as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers. It also can be used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA).
3. The 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 .
4. Used 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
5. foaming agent and inhibitor in plastic and elastomer materials
6. 2,2′-Azobis(2-methylpropionitrile) (AIBN) is a radical initiator. AIBN solution can be used to initiate radical-induced reactions, specifically free-radical polymerizations. It can be used in:Synthesis of styrene-vinyl pyridine diblock copolymers by reversible addition-fragmentation chain transfer (RAFT) polymerization.Preparation of silicon oxycarbide glasses.Synthesis of poly [N-(p-vinyl benzyl) phthalimide] for the preparation of titanium dioxide composites for electrophoretic displays.

Recrystallization

1, 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 initiator

2,2'-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 lookchem of Tian Ye.

Chemical properties

White columnar crystals or white crystalline powder. Insoluble in water, soluble in methanol, ethanol, acetone, ether, petroleum ether and aniline and other organic solvents.

Production method

Acetone, 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.

category

Flammable solids

Toxicity grading

Middle toxic

Acute toxicity

Oral-rat LDL0: 670 mg/kg; Oral-Mouse LD50: 700 mg/kg

Explosive hazardous characteristics

Explosive when mixed with oxidants ; easily oxidized, unstable and intense heat decomposition, explosive when heated with heptane, acetone

Flammability hazard characteristics

Flammable in case of fire, high temperature, oxidant ; decomposition and generating combustible gas in case of thermal ; combustion produces toxic fumes of nitrogen oxides

Storage characteristics

Treasury ventilation low-temperature drying; and separated from oxidants

Extinguishing agent

Water, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent

Chemical Properties

Different sources of media describe the Chemical Properties of 78-67-1 differently. You can refer to the following data:
1. white solid
2. Azobisisobutylonitrile is a white crystalline compound.

General Description

Insoluble 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.

Reactivity Profile

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'-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.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Easily oxidized, unstable. Violent exothermic decomposition when heated. Solution in acetone may decompose explosively. Explodes when heated with heptane. When heated to decomposition it emits toxic fumes of NO, and CN-. See also NITRILES. A free-radcal generator.

Potential Exposure

Azobisisobutylonitrile is both a nitrile and azo compound. Used as a polymerization initiator, free radical generator (or initiator); as a catalyst in vinyl polymerizations; as a blowing agent for elastomers and plastics.

Shipping

UN3234 Self-reactive solid type C, temperature controlled materials, Hazard Class: 4.1; Labels: 4.1- Flammable solid, Technical Name Required.

Incompatibilities

Flammable; dust may form explosive mixture with air. Unstable and easily oxidized material; keep away from oxidizers, strong acids. Keep at temperature not ≧30° C (this may vary by manufacturer). Risk of explosion from heat, shock, friction. Warming causes production of tetramethylsuccinonitrile and cyanide fumes. Keep away from acetone and other ketones, alcohols, lithium, aluminum, aldehydes, and hydrocarbons, such as heptane. Azo 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. This chemical is sensitive to prolonged exposure to heat. This chemical is incompatible with strong oxidizing agents.

Synthetic route

2,2'-hydrazobis(2-methylpropionitrile) (6869-07-4) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III); pyrographite In dichloromethane at 40℃; for 6h;	99.5%
With hydrogenchloride; molybdophosphoric acid hydrate; dihydrogen peroxide; sodium docusate; sodium bromide In water at 16 - 17℃; for 4.5h; Reagent/catalyst;	95%
With dihydrogen peroxide In acetonitrile at 20℃; Temperature; Solvent;	95.6%

cetyltrimethylammonium chloride (112-02-7) + 2-amino-2-cyanopropane (19355-69-2) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With sodium hypochlorite	93.8%

2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile (171915-82-5) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With oxygen; tetra-N-butylammonium tribromide; sodium nitrite In 1,4-dioxane; water at 60℃; under 760.051 Torr; for 4h; Sealed tube;	72%

bis-(1-chloro-1-methyl-ethyl)-diazene (29540-62-3) + sodium cyanide (143-33-9) → 2,2'-azobis(isobutyronitrile) (78-67-1)

2-amino-2-cyanopropane (19355-69-2) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With sodium hypochlorite
With calcium hypochlorite
With oxygen; 1.5% Au/TiO2 In toluene at 100℃; under 2250.23 - 3750.38 Torr; for 40h;	46 %Chromat.

2,2'-hydrazobis(2-methylpropionitrile) (6869-07-4) + benzene (71-43-2) + dibenzoyl peroxide (94-36-0) → 2,2'-azobis(isobutyronitrile) (78-67-1)

α,α'-(dinitroso-hydrazo)-di-isobutyronitrile + water (7732-18-5) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
at 60℃;

hydrazoisobutyric acid dinitrile → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With hydrogenchloride; ethanol; bromine

2,2'-hydrazobis(2-methylpropionitrile) (6869-07-4) + benzene (71-43-2) + sodium peroxybenzoate → 2,2'-azobis(isobutyronitrile) (78-67-1)

dimethyl ditelluride (20334-43-4) + 2,2'-azobis(isobutyronitrile) (78-67-1) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate), -C(CN)(CH3)2 and -TeMe terminated, Mn 13100 by GPC, PDI 1.55 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; dimethyl ditelluride

Conditions	Yield
at 80℃; for 0.5h;	100%

2,2'-azobis(isobutyronitrile) (78-67-1) + acrylic acid n-butyl ester (141-32-2) → poly(n-butyl acrylate), -C(CN)(CH3)2 and -deuterium terminated, Mn 4400 by GPC, PDI 1.19 by GPC and Mn 4300 by MALDI-TOF-MS, PDI 1.16 by MALDI-TOF-MS; monomer(s): n-butyl acrylate; azoisobutyronitrile

Conditions	Yield
Stage #1: 2,2'-azobis(isobutyronitrile); acrylic acid n-butyl ester With dimethyl ditelluride at 90℃; Stage #2: With 2,2'-azobis(isobutyronitrile); tributyltin deuteride In various solvent(s) at 80℃;	99%

2,2'-azobis(isobutyronitrile) (78-67-1) + biphenyl-4-carboxylic acid (92-92-2) → N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-4-carboxamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	99%

2,2'-azobis(isobutyronitrile) (78-67-1) + 2-Iodobenzoic acid (88-67-5) → N-(2-cyanopropan-2-yl)-2-iodo-N-isobutyrylbenzamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	99%

2,2'-azobis(isobutyronitrile) (78-67-1) + N,N-di-p-tolylmethacrylamide → C22H24N2O

Conditions	Yield
With copper(l) iodide In dichloromethane at 80℃; for 24h; Inert atmosphere;	99%

2,2'-azobis(isobutyronitrile) (78-67-1) + N,N’-dimethyl-N,N’-di(4-pyridinyl)thiuram disulfide (1158958-94-1) → 2-cyanopropan-2-yl N-methyl-N-(pyridin-4-yl)carbamodithioate (1158958-96-3)

Conditions	Yield
In ethyl acetate for 16h; Reflux;	98.4%
In ethyl acetate for 16h; Reflux;	88%

pyridine (110-86-1) + 2,2'-azobis(isobutyronitrile) (78-67-1) → C18H22N6O12S4

Conditions	Yield
With sulfur trioxide In dichloromethane for 24h;	98%

2,2'-azobis(isobutyronitrile) (78-67-1) + p-Toluic acid (99-94-5) → N-(2-cyanopropan-2-yl)-N-isobutyryl-4-methylbenzamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

2,2'-azobis(isobutyronitrile) (78-67-1) + 4-(1,1-dimethylethyl)benzoic acid (98-73-7) → 4-tert-Butyl-N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamideWhite

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

2,2'-azobis(isobutyronitrile) (78-67-1) + 2-iodoyl-5-methylbenzoic acid (52548-14-8) → N-(2-cyanopropan-2-yl)-2-iodo-N-isobutyryl-5-methylbenzamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

2,2'-azobis(isobutyronitrile) (78-67-1) + 5-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide → 3-cyano-5-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	98%

2,2'-azobis(isobutyronitrile) (78-67-1) + N-(2-naphthalenecarbonyl)-8-aminoquinoline (444079-13-4) → 2-(quinolin-8-yl)-1H-benzo[f]isoindole-1,3(2H)-dione

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	98%

cobaltocene (1277-43-6) + 2,2'-azobis(isobutyronitrile) (78-67-1) → C5H5CoC5H5C(CH3)2CN

Conditions	Yield
In toluene excess of Co(C5H5)2, complete exclusion of O2, in boiling toluene; mechanism discussed;;	97%
In toluene excess of Co(C5H5)2, complete exclusion of O2, in boiling toluene; mechanism discussed;;	97%
In further solvent(s) further solvent: styrol; excess of Co(C5H5)2, complete exclusion of O2;;	0%

2,2'-azobis(isobutyronitrile) (78-67-1) + 2-Biphenylcarboxylic acid (947-84-2) → N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-2-carboxamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	97%

2,2'-azobis(isobutyronitrile) (78-67-1) + 2-bromobenzoic-acid (88-65-3) → 2-Bromo-N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	97%

2,2'-azobis(isobutyronitrile) (78-67-1) + 4-n-methylphenylacetylene (766-97-2) → 3-(4-methylphenyl)-2-propynenitrile (151589-34-3)

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 10h;	97%
With Cu(2+)*C21H10NO6(3-)*C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	93%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

1-ethynyl-4-fluorobenzene (766-98-3) + 2,2'-azobis(isobutyronitrile) (78-67-1) → 3-(4-fluorophenyl)-2-propynenitrile (575433-43-1)

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 8h;	97%
With Cu(2+)*C21H10NO6(3-)*C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	94%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

2,2'-azobis(isobutyronitrile) (78-67-1) + 2-(tert-butylamino)-1-(4-methylphenyl)-2-oxoethyl 3-phenyl-2H-azirine-2-carboxylate → (Z)-2-(tert-butylamino)-1-(4-methylphenyl)-2-oxoethyl 3-amino-3-phenylacrylate

Conditions	Yield
With tri-n-butyl-tin hydride In benzene at 90℃; for 0.5h;	97%

2,2'-azobis(isobutyronitrile) (78-67-1) + diphenyl ditelluride (32294-60-3) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate), -C(CN)(CH3)2 and -TePh terminated, Mn 50100 by GPC, PDI 1.22 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; diphenyl ditelluride

Conditions	Yield
Stage #1: 2,2'-azobis(isobutyronitrile); diphenyl ditelluride In various solvent(s) at 80℃; for 3h; Stage #2: methacrylic acid methyl ester In various solvent(s) at 80℃; for 4h;	96%

bis(2,6-dimethylthiobenzoyl) disulfide + 2,2'-azobis(isobutyronitrile) (78-67-1) → 2-cyanoprop-2-yl 2,6-dimethyldithiobenzoate (851729-41-4)

Conditions	Yield
In ethyl acetate for 16h; Heating;	96%

2,2'-azobis(isobutyronitrile) (78-67-1) + C21H18O3 (53151-59-0) → 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile (1089675-68-2) + 3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile (50654-42-7)

Conditions	Yield
With titanium tetrachloride In benzene at 80℃; for 1.5h; Inert atmosphere;	A 96% B n/a
With titanium tetrachloride In benzene at 80℃; for 1.5h; Inert atmosphere;	A n/a B 71%

2,2'-azobis(isobutyronitrile) (78-67-1) + benzoic acid (65-85-0) → N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamide

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	96%

2,2'-azobis(isobutyronitrile) (78-67-1) + 5-phenyl-N-(quinolin-8-yl)furan-2-carboxamide → 3-cyano-5-phenyl-N-(quinolin-8-yl)furan-2-carboxamide

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	96%

2,2'-azobis(isobutyronitrile) (78-67-1) + N-quinolin-8-yl-benzamide (33757-48-1) → 2-(quinolin-8-yl)-isoindoline-1,3-dione (19348-61-9)

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Time; Sealed tube; regioselective reaction;	96%

2,2'-azobis(isobutyronitrile) (78-67-1) + 4-methyl-N-(quinolin-8-yl)benzamide (33757-49-2) → 5-methyl-2-(quinolin-8-yl)isoindoline-1,3-dione

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	96%

2,2'-azobis(isobutyronitrile) (78-67-1) + phenylacetylene (536-74-3) → 2-cyano-1-phenylacetylene (935-02-4)

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)*C21H10NO6(3-)*C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	94%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

2,2'-azobis(isobutyronitrile) (78-67-1) + 4-cyanophenylacetylene (3032-92-6) → 4-(cyanoethynyl)benzonitrile

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)*C21H10NO6(3-)*C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	90%

2,2'-azobis(isobutyronitrile) (78-67-1) + 4-ethynyl-1,1'-biphenyl (29079-00-3) → 3-(1,1'-biphenyl)-4-yl-2-propynenitrile

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)*C21H10NO6(3-)*C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	88%

2,2'-azobis(isobutyronitrile) (78-67-1) + Thiram (137-26-8) → dimethyl-dithiocarbamic acid cyano-dimethyl-methyl ester

Conditions	Yield
In cyclohexane; chlorobenzene for 4h; Heating;	95%
In benzene for 24h; Heating;	93%

Upstream product

• 171915-82-5 2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile 
• 112-02-7 cetyltrimethylammonium chloride 
• 19355-69-2 2-amino-2-cyanopropane 
• 6869-07-4 2,2'-hydrazobis(2-methylpropionitrile) 
• 71-43-2 benzene 
• 7732-18-5 water 
• 94-36-0 dibenzoyl peroxide 
• 29540-62-3 bis-(1-chloro-1-methyl-ethyl)-diazene 
• 143-33-9 sodium cyanide 

Downstream Products

• 6336-46-5 (1,3,3,3-tetrachloro-propyl)-boronic acid dibutyl ester 
• 111589-15-2 N,O-bis-(1-cyano-1-methyl-ethyl)-N-(4-nitro-phenyl)-hydroxylamine 
• 114254-56-7 N-[2-(1-cyano-1-methyl-ethoxy)-4-nitro-phenyl]-N,O-bis-(1-cyano-1-methyl-ethyl)-hydroxylamine 
• 823-78-9 meta-bromobenzyl bromide 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 108-85-0 1-bromocyclohexane 
• 111-87-5 octanol 
• 109286-26-2 N,O-bis-(1-cyano-1-methyl-ethyl)-N-(3,5-dinitro-phenyl)-hydroxylamine 
• 260-94-6 acridine 
• 52674-05-2 2-(9,10-dihydro-acridin-9-yl)-2-methyl-propionitrile 
• 4838-42-0 9,10,9',10'-tetrahydro-9,9'-biacridyl 
• 78-82-0 Isobutyronitrile 
• 116977-29-8 3-acetoxy-1-acetylsulfanyl-propene 

Relevant articles and documents

Highly efficient oxidation of 2,2′-hydrazobis-isobutyronitrile to 2,2′-Azobis-isobutyronitrile over a CrO: X/TiO2catalyst with hydrogen peroxide

Green oxidation of 2,2′-hydrazobis-isobutyronitrile (HAIBN) to 2,2′-Azobis-isobutyronitrile (AIBN) over a recyclable solid catalyst was a significant challenge. A titanium dioxide-supported chromium oxide (CrOx/TiO2) catalyst was, for the first time, developed for oxidation of HAIBN with hydrogen peroxide and achieved complete conversion of HAIBN with a high (94.8%) yield of AIBN.

METHOD FOR PRODUCING AZO COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo groups of hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of vanadium or cerium compounds, and a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

METHOD FOR PRODUCING AZO COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of at least one compound selected from the group consisting of vanadium and cerium compounds, the oxidation reaction to be performed without using a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT