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4-nitrotoluene

Product name 4-nitrotoluene
Synonyms p-nitrotoluene
GOST no data
CAS 99-99-0

4-Nitrotoluene is a colorless or light yellow crystalline solid. It is readily soluble in toluene, benzene, diethyl ether, chloroform, acetone and many other organic solvents. Solubility in water is about 0.0442% wt at 30°C.

Oxidation of p-nitrotoluene with potassium permanganate KMnO4, manganese(IV) oxide MnO2 or potassium dichromate K2Cr2O7 in acidic medium as well as by potassium hexacyanoferrate(III) K3[Fe(CN)6] in alkali medium results in o-nitrobenzoic acid. It can be also electrochemically oxidized in acetic or sulfuric acid to give o-nitrobenzaldehyde.

Nitro group in 4-nitrotoluene can be easily reduced with hydrogen in statu nascendi (e.g. by action of metal zinc in hydrochloric acid) to form p-toluidine (4-aminotoluene):

p-Toluidine formation by 4-nitrotoluene reduction


4-Nitrotoluene can be sulfonated into 2-position realtively methyl group to give 2-methyl-5-nitrobenzene sulfonic acid. Being heated with alkali in alcohol it dimerizes to form 4,4'-dinitrostilbene:

p-Nitrotoluene dimerization resulting in dinitrostilbene


Treatment of 4-nitrotoluene with the mixture of concentrated nitric and sulfuric acids results in formation of 2,4-dinitrotoluene and 2,4,6-trinitrotoluene. Additionally small amounts of other regio-isomers of dinitro- and trinitrotoluenes are formed.

Like other nitrotoluenes, p-nitrotoluene is quite toxic compound. It can be absorbed into the body by inhalation of its vapour or through the skin. It is able to oxidize haemoglobin of blood into hemiglobin and cause anaemia. It ia also dangerous to central nervous system and causes liver and kidney disorders.

Production.

Industrially p-nitrotoluene is manufactured by toluene nitration. End product of this reaction consists of the mixture of isomers. There are two processes which mostly used for 4-nitrotoluene preparation:

  • Liquid phase nitration. Toluene is nitrated with the mixture of 55-66% of sulfuric acid, 28-32% of nitric acid and 12-20% of water in continuous process. Reaction mixture is stirred intensively at the temperature 35-40°C. Stirring is needed because nitration occurs mostly in the phase interface. End product consists of 2-nitro, 3-nitro and 4-nitro isomers with the ratio 55-60%, 3-4% and 35-40% respectively. 4-Nitrotoluene is separated from the mixture by freezing, then the mixture is distilled at low pressure to isolate 2-nitrotoluene from 3-nitrotoluene.
  • Gaseous phase nitration. Toluene is nitrated with nitric acid at 100-140°C in the presence of catalyst (5% solution of sulfuric acid applied on silica gel or aluminum oxide). The toluene conversion is about 61%. The ratio of 4-nitrotoluene and 2-nitro isomer is 1.85:1

Uses.

  • as an intermediate for p-toluidine production. p-Toluidine is a significant intermediate in dyestuff industry;
  • in industrial preparation of 4-nitrobenzoic acid;
  • as a parent compound in nitrotoluenesulfonic acids and toluene nitrosulfonic chlorides syntheses;

Manufacturer(s) SE Chemical Plant Yuzhnyy
Chemical structure of 4-nitrotoluene

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