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BENZONITRILE


EC / List no.: 202-855-7
CAS no.: 100-47-0
Mol. formula: C7H5N


Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. 
This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. 
Benzonitrile is mainly used as a precursor to the resin benzoguanamine.


Production
Benzonitrile is prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F).[1]

C6H5CH3 + 3/2 O2 + NH3 → C6H5(CN) + 3 H2O

In the laboratory Benzonitrile can be prepared by the dehydration of benzamide or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene.

Applications
Laboratory uses
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. 
Benzonitrile reacts with amines to afford N-substituted benzamides after hydrolysis.
Benzonitrile is a precursor to Diphenylketimine Ph
2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis.


Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. 
One example is PdCl2(PhCN)2. 
The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.

History
Benzonitrile was reported by Hermann Fehling in 1844. 
He found the compound as a product from the thermal dehydration of ammonium benzoate.
He deduced its structure from the already known analogue reaction of ammonium formate yielding formonitrile. 
He also coined the name benzonitrile which gave the name to all the group of nitriles.

In 2018, benzonitrile was reported to be detected in the interstellar medium.

Benzonitrile is a clear colorless liquid with an almond-like odor. 
Flash point 161°F. 
Denser (at 8.4 lb / gal) than water and slightly soluble in water. 
Used as a specialty solvent and to make other chemicals.

Chemical Properties    
Bezonitrile is a colorless, oily liquid. Benzonitrile has an almond odor.
When heated to decomposition, benzonitrile emits toxic hydrogen cyanide and oxides of nitrogen


Occurrence    
Benzonitrile is reported to be found in natural cocoa aroma), in milk products, roasted filberts and peanuts and cooked trassi . 
Benzonitrile also has been detected in the thermal decomposition products of flexible polyurethane foam.

Uses    
The most important commercial use for benzonitrile is the synthesis of benzoguanamine, which is a derivative of melamine and is used in protective coatings and molding resins.

Uses    
Manufacture of benzoguanamine; intermediate for rubber chemicals; solvent for nitrile rubber, spe- cialty lacquers, and many resins and polymers, and for many anhydrous metallic salts.

Production Methods    
Benzonitrile can be prepared by one of the following methods: 
1) on a small scale by the dehydration in an inert solvent with phosphorus oxychloride or benzenesulfonyl chloride and an organic amine; 
2) from benzoic acid by heating with lead thiocyanate; 
3) by heating sodium benzenesulfonate with sodium cyanide or by adding benzenediazonium chloride solution to a hot aq sodium cyanide solution containing cupric sulfate and distilling by ammoxidation of toluene.


Production Methods    
Benzonitrile can be produced in high yield by the vapor-phase catalytic ammoxidation of toluene.


Chemical Reactivity    
Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Industrial uses    
Benzonitrile is used as an intermediate for rubber chemicals and as a solvent for nitrile rubber, specialty lacquers, many resins, polymers and for many anhydrous metallic salts (HSDB 1988; Hawley 1981). Benzonitrile is principally used as an intermediate for benzoguanamine (HSDB 1988). 
Benzonitrile is also used as an additive in nickel-plating baths, separating naphthalene and alkylnaphthalenes from non-aromatics by azetropic distillation; as jet-fuel additive; in cotton bleaching baths; as a drying additive for acrylic fibers; and in the removal of titanium tetrachloride and vanadium oxychloride from silicon tetrachloride (HSDB 1988; Smiley 1981). 
Benzonitrile is also used in perfumes at a maximum level of 0.2% in the final product (Opdyke 1979).


Metabolism    
Benzonitrile is mainly hydroxylated in vivo to cyanophenols, a small amount being hydrolysed to benzoic acid (Williams 1959). 
Benzonitrile also forms 6>-hydroxybenzonitrile, m-hydroxybenzonitrile, and /p-hydroxybenzonitrile in rabbits (HSDB 1988). 
In rabbit, 50% of a dose of 150 mg/kg was converted to conjugated cyanophenols and 10% of the benzonitrile fed was excreted as benzoic acid. 
Hydrogen cyanide is not a metabolite of benzonitrile (Williams 1959) and cyanide was not found to be formed by benzonitrile either in vivo or in vitro (Tanii and Hashimoto 1984). 
The in vivo microsomal hydroxylation of specifically deuterated benzonitrile in the rat yielded mainly 4-hydroxybenzonitrile with 41% retention of deuterium (Daly et al 1968).

Purification Methods    
Dry benzonitrile with CaSO4, CaCl2, MgSO4 or K2CO3, and distil Benzonitrile from P2O5 in an all-glass apparatus, under reduced pressure (b 69o/10mm), collecting the middle fraction. 
Distillation from CaH2 causes some decomposition of benzonitrile. 
Isonitriles can be removed by preliminary treatment with conc HCl until the odour of isonitrile (carbylamine) has gone, followed by preliminary drying with K2CO3. 
(This treatment also removes amines.) Steam distil (to remove small quantities of carbylamine). 
The distillate is extracted into ether, washed with dilute Na2CO3, dried overnight with CaCl2, and the ether is removed by evaporation. 
The residue is distilled at 40mm (b 96o).
Conductivity grade benzonitrile (specific conductance 2 x 10-8 mho) is obtained by treatment with anhydrous AlCl3, followed by rapid distillation at 40-50o under vacuum. 
After washing with alkali and drying with CaCl2, the distillate is redistilled in a vacuum several times at 35o before fractionally crystallising several times by partial freezing. 
Benzonitrile is dried over finely divided activated alumina from which Benzonitrile is withdrawn when required [Van Dyke & Harrison J Am Chem Soc 73 402 1951].


Incompatibilities    
May form explosive mixture with air. 
Strong acids which can release hydrogen cyanide. 
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. 
Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. 
Nitriles may polymerize in the presence of metals and some metal compounds. 
They are incompatible Benzonitrile 403 with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. 
Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. 
The combination of bases and nitriles can produce hydrogen cyanide. 
Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). 
These reactions generate heat. 
Peroxides convert nitriles to amides. 
Nitriles can react vigorously with reducing agents. 
Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. 
They are also insoluble in aqueous acids


Benzonitrile appears as a clear colorless liquid with an almond-like odor. 
Flash point 161°F. 
Denser (at 8.4 lb / gal) than water and slightly soluble in water. 
Used as a specialty solvent and to make other chemicals.

Benzonitrile is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group. 
Benzonitrile is a member of benzenes and a nitrile.


Use and Manufacturing

Synthesis of benzoquanamine; additive in nickel-plating baths; for separating naphthalene and alkylphthalenes from non-aromatics by azetropic distillation; as jet-fuel additive; in cotton bleaching baths; as a drying additive for acrylic fibers; in the removal of titanium tetrachloride and vanadium oxytrichloride from silicon tetrachloride.


Intermediate for rubber chemicals; solvent for nitrile rubber, specialty lacquers, and many resins and polymers, and for many anhydrous metallic salts.


In perfumes at a maximum level of 0.2% in the final product

Solvent

Industry Uses
Intermediates

Benzonitrile is a stable compound to pyrolysis, and its decomposition starts above 550°C with a very low decomposition rate. 
A study performed in a flow reactor on N2 saturated with benzonitrile in the temperature range 550–600°C showed that the main pyrolysis products of this compound are HCN, benzene, monocyanodiphenyls, dicyanodiphenyls, and dicyanobenzenes as well as char.
The position of the hydrogen atom where the cleavage takes place is not preferential because pyrolysis generates a mixture of monocyanodiphenyls, dicyanodiphenyls, and dicyanobenzenes (e.g., 2-cyano, 3-cyano, and 4-cyanobiphenyl). 
The presence of dicyanobenzene in the pyrolyzate indicates that free CN• radicals are likely to be formed in the reaction. 
Kinetic parameters for the reactions of benzonitrile decomposition are reported in the literature, with the formation of different compounds having different reaction orders.
 The pyrolyzate at 575°C obtained for 30 min contact time contains about 5.9 mole % HCN, 4.9 mole % dicyanobenzenes, 3.0 mole % benzene, 1.2% monocyanobiphenyls, and the other compounds at lower levels.

Used as a solvent and intermediate in industries making drugs, perfumes, dyes, rubber, textiles, resins, and specialty lacquers;

Benzonitrile a colorless toxic oily compound C6H5CN of almond-oil odor made by fusing a mixture of sodium cyanide and sodium benzenesulfonate and in other ways and used chiefly as a solvent for synthetic resins.

Solvent and intermediate for the synthesis of agrochemicals, pharmaceuticals, chemical intermediates and high performance pigments.
We can offer the Benzonitrile in iso-container as well as steel drums.

Applications:
Benzonitrile is a widely utilized as a solvent and an intermediate in industries making drugs, perfumes, dyes, rubber, textiles, resins and specialty lacquers. 
Benzonitrile finds application as a versatile precursor for many derivatives. 
Benzonitrile coordinates with transition metal to form complexes which act as synthetic intermediates.

Notes
Hygroscopic.
Incompatible with strong bases, strong oxidizing agents, reducing agents, acids, chlorates, nitrates and plastics.

Benzonitrile is commonly used as a precursor to synthesize a wide range of aromatic compounds and also forms stable coordination complexes with transition metals.

Benzonitrile is a useful solvent and precursor.
As a synthetic intermediate in coordination complexes, Benzonitrile is both soluble in organic solvents and readily displaced by stronger ligands. 
Benzonitrile will also form N-substituted bebzamides upon hydrolysis reactions with amines.

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN.

Properties
Chemical
Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile.

Physical
Benzonitrile is a colorless liquid with a sweet almond odor.

Availability
Benzonitrile is sold by chem suppliers.

Preparation
Benzonitrile can be prepared by heating a mixture of benzamide and ammonium sulfamate. 
The reaction produces ammonia and ammonium bisulfate as side products.

Can be prepared by the dehydration of benzamide at high temperatures in the presence of catalyst. 
Another accessible route is reaction between cuprous cyanide or NaCN with bromobenzene in DMSO, known as Rosenmund–von Braun reaction.

Benzonitrile can be prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at temperatures between 400-450 °C:


Electroreduction of benzonitrile
Benzylamine is used as a photographic fixing agent, as a corrosion inhibitor and also as a raw material for the preparation of powerful explosives which are easy to handle. 
The conventional method adopted for the preparation of benzylamine is the catalytic hydrogenation of benzonitrile in absolute ethanol under high pressure. 
In the present communication, a novel electrolytic reduction technique for the conversion of benzonitrile to benzylamine, using a palladium black deposited on graphite cathode, is described. 
Galvanostatic polarization studies, using both a stationary and a rotating cylindrical palladium black deposited cathode, revealed that there is considerable depolarization only in a very low current density regions. 
The identity of benzylamine has been confirmed by NMR, mass spectral and infrared data. 
Carbon, hydrogen and nitrogen analysis also support the identity of benzylamine. 
This simple electrochemical reduction technique opens up a new route for the reduction of cyanide groups to the primary amine groups.

Methods of Manufacturing
Prepared by heating Na benzenesulfonate with NaCN or by adding benzenediazonium chloride solution to a hot aqueous NaCN solution containing CuSO4 and distilling.

From benzoic acid by heating with lead thiocyanate.

The reaction of benzoic acid (or substituted benzoic acid) with urea at 220-240 °C in the presence of a metallic catalyst.

Benzonitrile can be produced in high yield by the vapor-phase catalytic ammoxidation of toluene.


IDENTIFICATION AND USE: 
Benzonitrile is a colorless liquid. Benzonitrile is used as intermediate for rubber chemicals; solvent for nitrile rubber, specialty lacquers, and many resins and polymers, and for many anhydrous metallic salts. 


Benzonitrile may be used in the synthesis of organic building blocks such as 2-cyclopentylacetophenone, 4-carbomethoxy-5-methoxy-2-phenyl-1,3-oxazole and 1-phenyl-3,4-dihydro-6,7-methylenedioxyisoquinoline. 
Benzonitrile may also be used as a solvent in the synthesis of bis(trifluoromethyl)diazomethane.

Benzonitrile (CAS NO. 100-47-0) should be dried with CaSO4, CaCl2, MgSO4 or K2CO3, and distd from P2O5 in an all-glass apparatus, under reduced pressure (b 69 °C/10mm), collecting the middle fraction. Distn from CaH2 causes some decomposition of solvent. 
Isonitriles can be removed by preliminary treatment with conc HCl until the smell of isonitrile has gone, followed by preliminary drying with K2CO3. (This treatment also removes amines).

Applications
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. 
Benzonitrile reacts with amines to afford N-substituted benzamides after hydrolysis, Benzonitrile is a precursor to Ph2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by hydrolysis.

Benzonitrile can form coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile, e.g. PdCl2(PhCN)2. 
The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.


About this substance
Helpful information
This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.

This substance is used at industrial sites and in manufacturing.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. 
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the types of manufacture using this substance. 
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Uses at industrial sites
This substance has an industrial use resulting in manufacture of another substance (use of intermediates).
This substance is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of this substance can occur from industrial use: manufacturing of the substance.

Molecular formula: C7H5N
Molar mass: 103.121
CAS Registry Number: 100-47-0
Appearance: Benzonitrile, 99%; Benzonitrile, 99%; colourless liquid
Melting point: -13 °C
Boiling point: 191 °C
Solubility: Water, 2000 mg/L (25 deg C)

Benzonitrile Chemical Compound is the chemical compound with the formula C6H5CN, abbreviated PhCN. 
This aromatic organic compound is a colorless liquid with a sweet almond odour. 
Benzonitrile is mainly used as a precursor to the resin benzoguanamine.


Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. 
This aromatic organic compound is a colorless liquid with a sweet almond odour. 
Benzonitrile is mainly used as a precursor to the resin benzoguanamine.


Uses
The most important commercial use for benzonitrile is the synthesis of benzoguanamine, which is a derivative of melamine and is used in protective coatings and molding resins.


Production
Benzonitrile is prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F).

In the laboratory Benzonitrile can be prepared by the dehydration of benzamide or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene.

Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhCN.
This aromatic organic compound is mainly used as a precursor to the resin benzoguanamine


IUPAC NAMES: 
Benzonitrile
benzonitrile
Benzonitrile

SYNONYMS:
PHENYL CYANIDE
PHENYLMETHANITRILE
Benzontrile
Benzoitrile
BENZONITRILE, 99.9%, HPLC GRADE
BENZONITRILE, REAGENTPLUS, 99%
BENZONITRILE OEKANAL, 250 ML
BENZONITRILE, ANHYDROUS, 99+%
Benzonitrile, extra pure, 99%
Benzonitrile, for spectroscopy, 99+%
AKOS BBS-00004403
AKOS B004231
AKOS 91614
CYANOBENZENE
BENZONITRILE
BN
2BNC
3BN
Benzene, cyano-
benzenecarbonitrile
Benzenenitrile
Benzoic acid nitrile
benzoicacidnitrile
BRR
C.I.SulphurBlue7(53440)
cyano-benzen
FB
Fenylkyanid
ImmedialIndoneRF
KayakuSul-phurBlueBK
MifsuiSulphurBlueBC
ThionolBlue2BN
Benzonitrile ReagentPlus(R), 99%
Sulphur Blue BRN
Benzonitrile, 99+%
Benzonitrile, 99%, J&KSeal
Benzonitrile, 99%, SuperDry, water≤30 ppm, J&KSeal
benzonitride
Benzonitrile( 99%, HyDry, Water≤50 ppm (by K.F.))
Benzonitrile( 99%, HyDry, with molecular sieves, Water≤50 ppm (by K.F.))
Benzonitril
BRN
phenylcyanide,benzonitrile,cyanobenzene
BENZONITRILE,REAGENT
phenylnitrile
Benzonitrile, 99%, extra pure
Benzonitrile, for spectroscopy
Benzenenitrile (benzonitrile)
Benzonitrile,99+%,for spectroscopy
Benzonitrile,Phenyl cyanide
Benzonitrile 10g [100-47-0]
Benzonitrile, 99%, pure
Benzonitrile, extra pure, 99% 1LT
BENZONITRILE FOR SYNTHESIS
Benzonitrile, SuperDry, J&KSeal
Benzonitrile, J&KSeal
Benzonitrile, 99%, SpcDry, with Molecular sieves, Water≤50 ppM (by K.F.), SpcSeal
Benzonitrile 2


 

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