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1,4-Dicyanobutane

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Name

1,4-Dicyanobutane

EINECS 203-896-3
CAS No. 111-69-3 Density 0.945 g/cm3
PSA 47.58000 LogP 1.59396
Solubility 90 g/L (20 °C) in water Melting Point 1-3 °C(lit.)
Formula C6H8N2 Boiling Point 296.1 °C at 760 mmHg
Molecular Weight 108.143 Flash Point 149 °C
Transport Information UN 2205 6.1/PG 3 Appearance clear colorless to slightly yellow liquid
Safety 26-36-45-39 Risk Codes 25-36/37/38-36/38-23/25
Molecular Structure Molecular Structure of 111-69-3 (1,4-Dicyanobutane) Hazard Symbols ToxicT
Synonyms

Adiponitrile(8CI);Adipic acid dinitrile;Adipic acid nitrile;Adipicdinitrile;Hexanedinitrile;Butanedicarbonitrile;NSC 7617;

Article Data 219

1,4-Dicyanobutane Synthetic route

110-52-1

1,4-dibromo-butane

151-50-8

potassium cyanide

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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%
628-94-4

adipamide

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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
ConditionsYield
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%
628-21-7

1,4-Diiodobutane

104-85-8

para-methylbenzonitrile

111-69-3

hexanedinitrile

Conditions
ConditionsYield
In acetone at 70℃; for 1.83333h; Temperature;94%
124-09-4

1,6-Hexanediamine

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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%
74-90-8

hydrogen cyanide

592-51-8

4-Pentenenitrile

4635-87-4

3-pentenenitrile

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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%
107-13-1

acrylonitrile

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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%
1119-85-3

1,4-dicyano-2-butene

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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.
111-50-2

Adipic acid dichloride

111-69-3

hexanedinitrile

Conditions
ConditionsYield
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
124-04-9

Adipic acid

506-77-4

cyanogen chloride

111-69-3

hexanedinitrile

Conditions
ConditionsYield
In sulfolane; iron(III) chloride84%

1,4-Dicyanobutane Chemical Properties

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

1,4-Dicyanobutane 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

1,4-Dicyanobutane 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.

1,4-Dicyanobutane 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.

1,4-Dicyanobutane Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

1,4-Dicyanobutane Safety Profile

Hazard Codes: ToxicT
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.

1,4-Dicyanobutane Standards and Recommendations

ACGIH TLV: TWA 2 ppm (skin)
NIOSH REL: TWA 18 mg/m3
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

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