Nitric Acid → 4-Nitrotoluene

HRID 1076803Notes

Reaction equation

HRID 1076803 reaction equation
[N+:1]([O-:4])(O)=[O:2].[O-]S([O-])(=O)=O.[Ca+2].[N+](C1C=CC=CC=1)([O-])=O.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[N+:1]([C:23]1[CH:24]=[CH:25][C:20]([CH3:26])=[CH:21][CH:22]=1)([O-:4])=[O:2]

Participants

5

Reactant 4

HCID 944Nitric Acid2×HCID 1140Toluene3×HCID 7416NitrobenzeneHCID 24497Calcium Sulfate

Product 1

HCID 74734-NitrotolueneYield 89%

Procedure

A 100 gram portion of the powdered, soluble anhydrite (Drierite) was added to 100 milliliters toluene and mixed therein. A 13.6 gram portion of anhydrous nitric acid was added to the mixture of toluene and soluble anhydrite drop by drop over a 30 minute period. After all of the nitric acid was added to the toluene-soluble anhydrite mixture, the reaction was permitted to continue for 3 hours at 25° C. Then 26 grams nitrobenzene was added to the reaction medium and the medium was stirred for an additional 30 minutes. The reaction medium then was filtered and the filtrate was analyzed by gas chromotography using the added nitrobenzene as the internal standard. Results showed that a yield of 89% mononitrotoluene, based on the nitric acid, was obtained.

Workup

  1. additionmixed
  2. filtrationThe reaction medium then was filtered
  3. customResults

Sources & evidence

ORD record
ord-c91d6257477e4f3080749cfc4734f5d8
Source dataset
uspto-grants-1976_05
Patent number
US03957889

Reaction notes

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