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| CAS No.: | 111-69-3 |
|---|---|
| Name: | 1,4-Dicyanobutane |
| Article Data: | 219 |
| Molecular Structure: | |
|
|
|
| Formula: | C6H8N2 |
| Molecular Weight: | 108.143 |
| Synonyms: | Adiponitrile(8CI);Adipic acid dinitrile;Adipic acid nitrile;Adipicdinitrile;Hexanedinitrile;Butanedicarbonitrile;NSC 7617; |
| EINECS: | 203-896-3 |
| Density: | 0.945 g/cm3 |
| Melting Point: | 1-3 °C(lit.) |
| Boiling Point: | 296.1 °C at 760 mmHg |
| Flash Point: | 149 °C |
| Solubility: | 90 g/L (20 °C) in water |
| Appearance: | clear colorless to slightly yellow liquid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 25-36/37/38-36/38-23/25 |
| Safety: | 26-36-45-39 |
| Transport Information: | UN 2205 6.1/PG 3 |
| PSA: | 47.58000 |
| LogP: | 1.59396 |
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| Conditions | Yield |
|---|---|
| With 18-crown-6 ether In acetonitrile for 15h; Heating; | 96% |
| With Polysorbate 80 (1) In acetonitrile for 1.5h; Product distribution; Heating; other alkyl halides; | 70% |
| With Polysorbate 80 (1) In acetonitrile for 1.5h; Heating; | 70% |
| Conditions | Yield |
|---|---|
| With phosphorus pentachloride; toluene-4-sulfonic acid for 2h; Reagent/catalyst; Temperature; Reflux; | 96% |
| With di(n-butyl)tin oxide In toluene Heating; | 84% |
| With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating; | 83% |
- 74-90-8
hydrogen cyanide
- 13284-42-9
2-pentenenitrile
- 592-51-8
4-Pentenenitrile
- 4635-87-4
3-pentenenitrile
- 111-69-3
hexanedinitrile
| Conditions | Yield |
|---|---|
| With zinc(II) chloride at 50℃; for 49 - 53h; Product distribution / selectivity; | 95% |
| With zinc(II) chloride at 50℃; for 49 - 53h; Product distribution / selectivity; | 95% |
| With iron(II) chloride at 50℃; for 69 - 78h; Product distribution / selectivity; | 94.4% |
| Conditions | Yield |
|---|---|
| In acetone at 70℃; for 1.83333h; Temperature; | 94% |
| Conditions | Yield |
|---|---|
| With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane for 24h; Ambient temperature; | 93% |
| With potassium hydroxide In water; tert-butyl alcohol at 40℃; for 4h; electrolysis at a Ni(OH)2 anode and a steel cathode, current - 2 A, cell voltage - 2.0 V; | 93% |
| With tetrabutylammomium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Molecular sieve; | 86% |
| Conditions | Yield |
|---|---|
| With zinc(II) chloride at 50℃; for 45 - 48h; Product distribution / selectivity; | 93% |
| With zinc(II) chloride at 50℃; for 45 - 48h; Product distribution / selectivity; | 93% |
| With zinc(II) chloride at 50℃; for 46 - 54h; Product distribution / selectivity; | 92.5% |
| Conditions | Yield |
|---|---|
| With water; triphenylphosphine; zinc; diiodobis(triphenylphosphine)cobalt(II) In acetonitrile at 80℃; for 24h; | 89% |
| With potassium phosphate; tetraethylammonium phosphate at 20 - 22℃; Product distribution; electrolytic hydrodimerization, var. quaternary ammonium salts, var. electrodes; | 86.9% |
| With potassium phosphate; tetraethylammonium phosphate at 20 - 22℃; electrolysis; | 86.9% |
| Conditions | Yield |
|---|---|
| With formic acid In methanol; water at 100℃; for 12h; Green chemistry; chemoselective reaction; | 88% |
| With hydrogen; (o-OC6H4CH3)3PRuCl(PPh3)2 at 130℃; under 3620.04 Torr; for 20h; | 78 % Chromat. |
| With hydrogen; (o-OC6H4CH3)3PRuCl(PPh3)2 at 130℃; under 3620.04 Torr; for 20h; Product distribution; | 78 % Chromat. |
| Conditions | Yield |
|---|---|
| With sulfonamide; toluene-4-sulfonic acid In toluene at 120℃; for 3h; | 85% |
| Multi-step reaction with 2 steps 1: ammonia 2: phosphorus pentachloride / 150 °C View Scheme |
| Conditions | Yield |
|---|---|
| In sulfolane; iron(III) chloride | 84% |
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Chemistry
Structure of Adiponitrile (CAS NO.111-69-3):
IUPAC Name: hexanedinitrile
Empirical Formula: C6H8N2
Molecular Weight: 108.1411
EINECS: 203-896-3
Index of Refraction: 1.432
Molar Refractivity: 29.67 cm3
Molar Volume: 114.3 cm3
Polarizability: 11.76×10-24cm3
Surface Tension: 39.9 dyne/cm
Density: 0.945 g/cm3
Flash Point: 149 °C
Enthalpy of Vaporization: 53.58 kJ/mol
Melting Point: 1-3 °C(lit.)
Boiling Point: 296.1 °C at 760 mmHg
Vapour Pressure: 0.00147 mmHg at 25°C
Water Solubility: 90 g/L (20 ºC)
Physical Appearance: clear colorless to slightly yellow liquid
Product Categories: Industrial/Fine Chemicals;Dinitriles & Trinitriles;Dinitriles
Synonyms of Adiponitrile (CAS NO.111-69-3): 1,4-Dicyanobutane ; Adipic acid dinitrile ; Adipinsaeuredinitril ;
Hexanedinitrile ; Hexanedioic acid, dinitrile ; Nitrile adipico ; Tetramethylene cyanide ; Tetramethylene dicyanide
Uses
Adiponitrile is an important precursor to the polymer nylon 66.
Almost all adiponitrile is hydrogenated to 1,6-diaminohexane for the production of nylon:
NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2
Production
Adiponitrile is made by two different methods.
One method is by the electrohydrodimerization of acrylonitrile. It is converted into hexamethylenediamine (HMDA) that is used to make nylon.
2CH2=CHCN → NC(CH2)4CN
NC(CH2)4CN → H2N(CH2)6NH2
In the electrodimerization of acrylonitrile, a two-phase system containing a phase transfer catalyst tetrabutylammonium tosylate is used.
Toxicity Data With Reference
| 1. | orl-rat LD50:155 mg/kg | GISAAA Gigiena i Sanitariya. 49 (12)(1984),40. | ||
| 2. | ihl-rat LC50:1710 mg/m3/4H | TOXID9 Toxicologist. 1 (1981),76. | ||
| 3. | orl-mus LD50:172 mg/kg | ARTODN Archives of Toxicology. 57 (1985),88. | ||
| 4. | ipr-mus LD50:40 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 . | ||
| 5. | orl-rbt LD50:22 mg/kg | GISAAA Gigiena i Sanitariya. 49 (12)(1984),40. | ||
| 6. | scu-gpg LD50:50 mg/kg | MELAAD Medicina del Lavoro. Industrial Medicine. 46 (1955),221. |
Consensus Reports
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.
Safety Profile
Hazard Codes: 
T
Risk Statements: 25-36/37/38-36/38-23/25
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: 26-36-45-39
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 the label whenever possible.)
S39:Wear eye / face protection.
RIDADR: UN 2205 6.1/PG 3
WGK Germany: 1
RTECS: AV2625000
HazardClass: 6.1
PackingGroup: III
Poison by inhalation, ingestion, subcutaneous, and intraperitoneal routes. The nitrile group will 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 reasonable care in well-ventilated areas. 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 NITRILES.
Standards and Recommendations
ACGIH TLV: TWA 2 ppm (skin)
NIOSH REL: TWA 18 mg/m3
DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD