Synthesis of nitrotoluene

Preparation of nitrotoluene

Here is described the method for the preparation of mononitrotoluene as the mixture of mostly orto and para isomers. This product is further used for the synthesis of 2,4-dinitrotoluene and 2,4,6-trinitrotoluene.

Preparation of nitrotoluene

Preparation of nitrotoluene

To the round bottom flask with good stirring 20 grams (or 0.22mol) of toluene are placed. To the stirred toluene from the dropping funnel, the nitrating mixture consisting 65% sulfuric acid, 10% nitric acid and 25% of water during 1.5 hours is slowly added.  During this addition the temperature slowly rises and reaches 37-40° C. The reaction is carry on for next 30 min by gently heating the mixture at 50° C. Then the reaction content is poured in an ice-cold water and separated yellow oil is washed few times with distilled water and 5% sodium carbonate solution in order to remove remaining inorganic acids.

Nitrotoluene also could be obtained by “reverse” mixing of toluene and nitrating agent.

To the well stirred flask with nitrating mixture consisting of 65% sulfuric acid, 10% nitric acid and 25% of water from the dropping funnel slowly toluene is added, that the reaction constantly rises and reaches 40-45° C.  Nitration reaction time is 30 min. The mononitrotoluene is separated by adding to ice-cold water and washing in a separatory funnel with water and sodium carbonate solution to remove remaining inorganic acids.

Орлова Е.Ю. – Руководство к лабораторному практикуму по получению нитросоединений. – М., 1969, 70-71

IUPAC Name

1-methyl-2-nitrobenzene

InChI

InChI=1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3

InChI Key

PLAZTCDQAHEYBI-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

1-methyl-2-nitrobenzene, 2-nitrotoluene, o-nitrotoluene, ortho-nitrotoluene

Depositor-Supplied Synonyms

2-Nitrotoluene, 1-Methyl-2-nitrobenzene, O-NITROTOLUENE, 88-72-2, o-Nitrotoluol, Benzene, 1-methyl-2-nitro-, o-Methylnitrobenzene, Toluene, o-nitro-, 2-Methyl-1-nitrobenzene, 2-Methylnitrobenzene, 2-Nitrotoluol, ortho-Nitrotoluol, Mononitrotoluene, Nitrotoluene, o-, NITROTOLUENE, Nitrotoluene, o-isomer, alpha-Methylnitrobenzene, NSC 9577, 1-methyl-2-nitro-benzene, CCRIS 1224, ONT, CHEBI:33098, HSDB 2189, PLAZTCDQAHEYBI-UHFFFAOYSA-N, EINECS 201-853-3, o-NT, AI3-16311, DSSTox_CID_5791, DSSTox_RID_77923, DSSTox_GSID_25791, ortho-nitrotoluene, CAS-88-72-2, 57158-05-1, 2-nitro toluene, Methylnitrobenzene, o-nitrophenylmethane, o-methyl nitrobenzene, 2-methyl-nitrobenzene, o-NITRO TOLUENE, o-Nitrotoluene, liquid, ACMC-1BKHO, TOLUENE,2-NITRO, AC1L1NND, AC1Q5AUO, UNII-6Q9N88YIAY, WLN: WNR B1, 6Q9N88YIAY, SCHEMBL26788, KSC179I8T, MLS001055384, CHEMBL47047, 438804_ALDRICH, 442365_SUPELCO, 45985_RIEDEL, PARAGOS 530089, SCHEMBL8008054, 74060_FLUKA, CTK0H9489, NSC9577, MolPort-001-783-153, HMS3039E06, LABOTEST-BB LTBB002340, LTBB002340, NSC-9577, Tox21_202393, Tox21_300032, ANW-39144, AR-1K9221, STL283955, ZINC01700065, AKOS000120143, AS00108, LS-1882, MCULE-5319832795, RL05548, RTR-032938, NCGC00090723-01, NCGC00090723-02, NCGC00090723-03, NCGC00254124-01, NCGC00259942-01, AJ-30444, AK114447, AN-42442, CJ-28670, SC-18126, SMR000677946, KB-173980, ST2415407, TR-032938, FT-0613226, N0275, o-Nitrotoluene, liquid [UN1664] [Poison], o-Nitrotoluene, liquid [UN1664] [Poison], C19597, 3B4-1340, I01-0409, InChI=1/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H

Removed Synonyms

Benzene, methylnitro-, Nitrotoluene, all isomers, UN 1664 (Related), CID6944, UN1664, LUF 5834, C029955, 1321-12-6, 333962-91-7, 6862-68-6

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2 comments

  1. Fritz Haber

    Expected composition of the individual isomers are (according to the Organikum):
    – ortho (2): 65%
    – para (4): 30%
    – meta (3): 5%

    Seperation can be accomplished by pouring the reaction mixture into ice water and filtering, followed by destillation.

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