Adiponitrile
IUPAC name	Hexanedinitrile
Other names	1,4-Dicyanobutane, Adipic acid dinitrile, Adipic acid nitrile, Hexanedioic acid dinitrile, Adipyldinitrile, Nitrile adipico, Tetramethylene cyanide, Tetramethylene dicyanide, UN 2205
Identifiers
CAS number	[111-69-3]
SMILES	N#CCCCCC#N
InChI	InChI=1/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2
Properties
Molecular formula	C6H8N2
Molar mass	108.14 g/mol
Appearance	Colourless
Density	0.97 g/cm3
Melting point	1 °C Image File history File links Size of this preview: 800 × 294 pixelsFull resolution (1100 × 404 pixel, file size: 18 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... This article or section does not cite any references or sources. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...
Boiling point	295 °C The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ...
Solubility in water	50 g/l (20 °C)
Vapor pressure	0.003 hPa (20 °C)
Hazards
Main hazards	Toxic, irritant
NFPA 704	Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... In chemistry and physics, Vapor pressure is the pressure of a vapor in equilibrium with its non-vapor phases. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 2 4 1
R-phrases	R23, R25, R36, R38
S-phrases	S26, S37, S45
Flash point	93 °C (decomposition)
Autoignition temperature	460 °C
Explosive limits	1.7 - 4.9 %V
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Adiponitrile is the chemical compound with the formula (CH₂)₄(CN)₂. This dinitrile is an important precursor to the polymer nylon 6.6. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... The explosive limit of a gas or a vapour, is the limiting concentration (in air) that is needed for the gas to ignite and explode. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... This article or section does not cite any references or sources. ... A nitrile is any organic compound which has a -C≡N functional group. ... A polymer is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Nylon is a generic designation for a family of synthetic polymers first produced on February 28, 1935 by Wallace Carothers at DuPont. ...

Because of the industrial value of adiponitrile, many routes have been developed for its synthesis. In one method, acrylonitrile is dimerized via electrosynthesis: Acrylonitrile (CH2=CH-C≡N), is a pungent smelling, extremely flammable organic liquid. ... Electrosynthesis in organic chemistry is the synthesis of chemical compounds in a electrochemical cell [1] [2] The main advantage of electrosynthesis over an ordinary redox reaction is avoidance of the potential wasteful other half-reaction and the ability to precisely tune the required potential. ...

2 CH₂CHCN + 2 e^- + 2 H⁺ → NCCH₂CH₂CH₂CH₂CN

It has also been prepared by the nickel-catalysed hydrocyanation of butadiene: General Name, Symbol, Number nickel, Ni, 28 Chemical series transition metals Group, Period, Block 10, 4, d Appearance lustrous, metallic and silvery with a gold tinge Standard atomic weight 58. ... Hydrocyanation is, most fundamentally, the process whereby H+ and –CN ions are added to a molecular substrate. ... Butadiene can refer to either one of two hydrocarbon chemical compounds which are alkenes that are isomers of each other. ...

2 CH₂CHCHCH₂ + 2 HCN → NCCH₂CH₂CH₂CH₂CN

Adiponitrile can be hydrogenated to 1,6-diaminohexane and hydrolysed to adipic acid.

External links

• International Chemical Safety Card 0211
• NIOSH Pocket Guide to Chemical Hazards 0015
• www.chemicalland.com
• www.nist.gov