Synthesis of 2,4-dinitrotoluene

Preparation of 2,4-dinitrotoluene

Preparation of 2,4-dinitrotoluene from toluene

Preparation of 2,4-dinitrotoluene from toluene

Preparation of 2,4-dinitrotoluene directly from toluene

100 g of toluene are placed in a 1000 ml round bottom flask, which is fitted with a thermometer reaching nearly to the bottom of the flask, a small dropping funnel, and a glass tube bent at right angles to carry off the fumes. The “nitrating acid” mixture of 100 ml of concentrated sulfuric acid (d=1.84 g/ml) and 80 ml concentrated nitric acid (d=1.45 g/ml) is added through the dropping funnel in small portions at a time, the flask being well stirred after each addition and the temperature being kept at 60° C. When all the mixture of sulfuric and nitric acid has been added, the temperature is kept at 60° C for additional 30 min. with constant stirring. Then the reaction mixture is allowed to cool. The content of the flask is transferred to a separating funnel and the mixture of inorganic acids is separated from the intermediate mononitrotoluene. The oil (a mixture of ortho and para nitrotoluene) is put back into the flask, and the second “nitrating acid” mixture of 190 ml concentrated sulfuric acid (d=1.84 g/ml) and 80 ml fuming nitric acid (d=1.5 g/ml) is added slowly. The temperature rises and is kept at 115° C, if necessary the reaction mixture is gently warmed. After the whole of the sulfuric and nitric acid mixture has been added, the flask is kept hot and stirred for 60 min. Then the reaction mixture poured, while still hot, into a huge amount of ice-water. The liquid dinitrotoluene is allowed to crystallize, which is further washed with distilled water in order to remove inorganic acids. 2,4-Dinitrotoluene is filtered and dried yielding 177 g of final product. 2,4-Dinitrotoluene forms long yellow needles with melting point 71° C.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 206-207, 1905

IUPAC Name

1-methyl-2,4-dinitrobenzene

InChI

InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3

InChI Key

RMBFBMJGBANMMK-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-]

MeSH Synonyms

2,4-dinitrotoluene

Depositor-Supplied Synonyms

2,4-DINITROTOLUENE, 1-Methyl-2,4-dinitrobenzene, 121-14-2, 2,4-Dinitrotoluol, 2,4-DNT, Benzene, 1-methyl-2,4-dinitro-, 2,4-Dinitromethylbenzene, Toluene, 2,4-dinitro-, RCRA waste number U105, Dinitrotoluol, NCI-C01865, 2,-Dinitrotoluene, 2,4-Dinitro-1-methylbenzene, 4-Methyl-1,3-dinitrobenzene, NSC 7194, RCRA waste no. U105, CCRIS 268, CHEBI:920, HSDB 1144, RMBFBMJGBANMMK-UHFFFAOYSA-N, EINECS 204-450-0, 2,4-Dinitrotoluene, practical grade, AI3-15342, DSSTox_CID_529, DSSTox_RID_75643, DSSTox_GSID_20529, DNT, 1-methyl-2,4-dinitro-benzene, 2,4-Dinitrotoluene (containing 0.5% 2,6-dinitrotoluene), 2,4-Dinitrotoluene (containing 1.0-1.5% 2,6-dinitrotoluene), 84029-42-5, CAS-121-14-2, DNT (Related), 2,4-dinitro-toluene, D.N.T (Related), Dinitrotoluene, 2,4-, ACMC-1BOER, Dinitrotoluene (Related), AC1Q2QSG, WLN: WNR B1 ENW, AC1L1R1P, SCHEMBL48806, KSC176O2N, 6-Methyl-1,3-dinitrobenzene, Ex100, 101397_ALDRICH, 45969_RIEDEL, CHEMBL259865, SGCUT00009, UNII-6741D310ED, 42290_FLUKA, 45969_FLUKA, CTK0H6726, NSC7194, MolPort-001-783-155, LTBB002348, NSC-7194, to_000001, EINECS 281-716-2, Tox21_201784, Tox21_300493, AR-1C4407, LS-641, ZINC01532112, AKOS003273098, 6741D310ED, MCULE-8221741719, RP24302, RTR-003467, NCGC00091755-01, NCGC00091755-02, NCGC00091755-03, NCGC00091755-04, NCGC00254317-01, NCGC00259333-01, AN-17727, AN-22839, CJ-24138, I911, KB-17721, TR-003467, D0856, FT-0084959, FT-0610215, C11006, AE-562/40879347, I01-10154, 3B3-033832, UNII-R64H0N1X9C component RMBFBMJGBANMMK-UHFFFAOYSA-N, Dinitrotoluene, technical grade (2,4 (77%)- and 2,6 (19%)-), InChI=1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H

Removed Synonyms

DINITROTOLUENE, Benzene,4-dinitro-, Toluene,4-dinitro-, Benzene, methyldinitro-, CID8461, c1313, C016403, 25321-14-6, 13349-87-6

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