| Identification | More | [Name]
1,4-Dicyanobutane | [CAS]
111-69-3 | [Synonyms]
1,4-DICYANOBUTANE
ADIPIC ACID DINITRILE
ADIPONITRILE
BUTANE-1,4-DICARBONITRILE
HEXANEDINITRILE
TETRAMETHYLENE CYANIDE
TETRAMETHYLENE DICYANIDE
Adipic acid nitrile
adipicacidnitrile
Adipicdinitrile
adipinsaeuredinitril
Adipodinitrile
adiponitril
Adipyldinitrile
adipylnitrile
Hexanedioic acid dinitrile
hexanedioicacid,dinitrile
hexanedioicaciddinitrile
Nitrile adipico
nitrileadipico | [EINECS(EC#)]
203-896-3 | [Molecular Formula]
C6H8N2 | [MDL Number]
MFCD00001975 | [Molecular Weight]
108.14 | [MOL File]
111-69-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Adiponitrile is a combustible, water-white to yellow, oily liquid. A solid below 1.1 C. Practically odorless | [Melting point ]
1-3 °C (lit.) | [Boiling point ]
295 °C (lit.) | [density ]
0.951 g/mL at 25 °C(lit.)
| [vapor density ]
3.7 (vs air)
| [vapor pressure ]
0.01 mm Hg ( 40 °C)
| [refractive index ]
n20/D 1.438(lit.)
| [Fp ]
163 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
50g/l | [form ]
Liquid | [color ]
Clear colorless to slightly yellow | [Specific Gravity]
0.951 | [explosive limit]
7-14%(V) | [Water Solubility ]
90 g/L (20 ºC) | [FreezingPoint ]
1℃ | [BRN ]
1740005 | [Dielectric constant]
32.5（Ambient） | [Exposure limits]
TLV-TWA 18 mg/m3 (4 ppm) (NIOSH). | [CAS DataBase Reference]
111-69-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Hexanedinitrile(111-69-3) | [EPA Substance Registry System]
111-69-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/38:Irritating to eyes and skin .
R23/25:Toxic by inhalation and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S39:Wear eye/face protection . | [RIDADR ]
UN 2205 6.1/PG 3
| [WGK Germany ]
1
| [RTECS ]
AV2625000
| [Autoignition Temperature]
460 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 | [Safety Profile]
Poison by inhalation, ingestion, subcutaneous, and intraperitoneal routes. The nitrile group wdl behave as a cyanide when ingested or absorbed in the body. It produces disturbances of the respiration and circulation, irritation of the stomach and intestines, and loss of weight. Its low vapor pressure at room temperature makes exposure to harmful concentrations of its vapors unlikely if handled with Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of CN-. Can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. See also HYDROCYANIC ACID and NITRILESreasonable care in well-venulated areas. | [Hazardous Substances Data]
111-69-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 138 mg/kg LD50 dermal Rabbit 2134 mg/kg |
| Hazard Information | Back Directory | [General Description]
A colorless to light colored solid, or a solid in a solution. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. | [Reactivity Profile]
ADIPONITRILE(111-69-3) is incompatible with strong oxidizers. ADIPONITRILE(111-69-3) is also incompatible with strong acids, strong bases and strong reducing agents. . | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
This material is toxic by ingestion and inhalation. It produces disturbances of the respiration and circulation, irritation of the stomach and intestine, and loss of weight. It is irritating to skin and eyes. | [Potential Exposure]
Is used to manufacture corrosion inhibitors, rubber accelerators, and Nylon 66; and in organic synthesis.
| [Fire Hazard]
Combustion products may contain hydrocyanic acid (HCN). Vapor may explode if ignited in an enclosed area. When heated to decomposition, ADIPONITRILE emits highly toxic fumes. Avoid oxidizing material. Hazardous polymerization may not occur. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Use amyl nitrate capsules if symptoms develop. All area employees should be trained regularly in emergency measures for cyanide poisoning and in CPR. A cyanide antidote kit should be kept in the immediate work area and must be rapidly available. Kit ingredients should be replaced every 1 2 years to ensure freshness. Persons trained in the use of this kit; oxygen use, and CPR must be quickly available. Effects may be delayed; keep victim under observation. | [Shipping]
UN2205 Adiponitrile, Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
May form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause violent reactions: fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Also incompatible with strong reducing agents such as hydrideds and active metals. Permissible Exposure Limits in Air | [Description]
Adiponitrile is an odorless, colorless liquid that decomposes
on heating to react violently with strong oxidants. Upon
burning, the highly toxic hydrogen cyanide is produced. | [Chemical Properties]
Adiponitrile is a combustible, water-white to yellow, oily liquid. A solid below 1.1 C. Practically odorless | [Waste Disposal]
Add excess alcoholic KOH. Than evaporate alcohol and add calcium hypochlorite. After 24 hours, flush to sewer with water. Can also be incinerated with afterburner and scrubber to remove nitrogen oxides. | [Uses]
Adiponitrile is used in the production of hexamethylenediamine for manufacturing nylon 6,6 and to produce adipoguanamine to make amino resins. | [Uses]
The major use of adiponitrile is as an intermediate in the
production of nylon. Lesser uses include that in organic
synthesis and in the preparation of adipoguanamine, which is
used as an extractant for aromatic hydrocarbons. | [Application]
Adiponitrile is used as a synthetic rubber accelerator, a rust inhibitor, an additive for detergents, a spinning solvent for acrylonitrile, methacrylonitrile and methyl methacrylate terpolymers, a solvent for wet spinning and dry spinning of polyvinyl chloride fibers , polyamide colorants, auxiliaries for fabric bleaches, acetate, propionate, butyrate and mixed ester plasticizers; and aromatic extracted extractants. | [Preparation]
The main method of industrial production of adiponitrile is the amination of adipic acid. Adipic acid and excess ammonia are reacted in the presence of catalyst phosphoric acid or its salts or esters at a temperature of 270-290°C to generate diammonium adipate, which is then heated and dehydrated to generate crude adiponitrile, The product is obtained by rectification. | [Production Methods]
Adiponitrile may be prepared by reacting butadiene with hydrogen cyanide, by the
electrodimerization of acrylonitrile, by heating adipamide with acetic anhydride in
the presence of cobalt or by reacting 1,4-dichlorobutane with sodium cyanide
(HSDB 1988). Impurities such as propionitrile, bis (cyanoethyl) ether or acrylonitrile
may be present depending on the method of manufacture (Smiley 1981). | [Synthesis Reference(s)]
Synthetic Communications, 10, p. 279, 1980 DOI: 10.1080/00397918008062751 | [Industrial uses]
Adiponitrile is used in nylon manufacturing, synthetic fiber synthesis, and in the
manufacture of rubber accelerators and corrosion inhibitors. It is also used as an
extractant for aromatic hydrocarbons (Smiley 1981). | [Environmental Fate]
The mechanism of adiponitrile’s toxicity relates to its ability to
release cyanide both in vitro and in vivo. Cyanide then forms
a stable complex with ferric iron in the cytochrome oxidase
enzyme. Since this enzyme occupies a central role in the utilization
of oxygen in practically all cells, inhibition produces an
inhibition of cellular respiration. | [Metabolism]
Animal studies indicated that the concentrations of thiocyanate in the blood and
urine of guinea pigs injected with adiponitrile were proportional to the doses
administered. Following administration of adiponitrile, 79% was eliminated as
thiocyanate in the urine of guinea pigs (H?rtung 1982). Of the cyanide antidotes,
thiosulfate was most effective in protecting against adiponitrile poisoning, and
nitrite was less effective. However, on the basis of the ratio between administered
adiponitrile dose and quantity of cyanide detected, Ghiringhelli, (1955) concluded
that a greater part of the dose was metabolized to cyanide. | [Purification Methods]
Reflux adiponitrile over P2O5 and POCl3, and fractionally distil it, then fractionate it through an efficient column. The liquid is TOXIC and is an IRRITANT. [Braun & Rudolph Chem Ber 67 1770 1934, Reppe et al. Justus Liebigs Ann Chem 596 127 1955, Gagnon et al. Can J Chem 34 1662 1956, Copley et al. J Am Chem Soc 62 228 1940, Beilstein 2 IV 1947.] | [Toxicity evaluation]
Adiponitrile will exist solely as a vapor in the ambient atmosphere.
The chemical can be degraded in air by photochemically
produced hydroxyl radicals with a half-life of 23 days.
Adiponitrile is expected to have very high mobility in soil, with
volatilization from soil or water surfaces not expected to be an
important fate process. The chemical is expected to biodegrade
in aquatic and soil systems. The potential for bioconcentration
in aquatic organisms is low. |
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