Nitric Acid → 4-Nitrotoluene
Reaction equation
[O-]S([O-])(=O)=O.[Ca+2].[N+:7]([O-:10])(O)=[O:8].[N+](C1C=CC=CC=1)([O-])=O.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[N+:7]([C:23]1[CH:24]=[CH:25][C:20]([CH3:26])=[CH:21][CH:22]=1)([O-:10])=[O:8]Participants
Conditions
- Temperature
- 100 °C
Procedure
An 86 gram portion of soluble anhydrite regenerated from Example II by first heating in a vacuum at 100°C for 7 hours for removal of organic material and then over night at 200°C. was added to a 100 milliliter portion of toluene. This mixture was heated to 45°C. and stirred while an 18.1 gram portion of anhydrous nitric acid was added drop by drop over a 30-minute period. Agitation was continued for 1 1/2 hours, then a 26 gram portion of nitrobenzene was added to the reaction mixture and stirring was continued for an additional hour. After this one hour period, the reaction mixture was filtered and the filtrate analyzed by gas chromotography using the nitrobenzene as the internal standard. A yield of 61% mononitrotoluene was obtained based on the nitric acid charged. The mononitrotoluene had the following composition: 44.1% ortho-nitrotoluene, 2.8% meta-nitrotoluene, and 53.1% paranitrotoluene. Thus the results show a substantial increase in the proportion of para-isomer was obtained by the addition of the soluble anhydrite to the reaction medium.
Workup
- temperatureThis mixture was heated to 45°C.
- additionwas added drop by drop over a 30-minute period
- customwas continued for 1 1/2 hours
- waitwas continued for an additional hour
- filtrationthe reaction mixture was filtered
Sources & evidence
- ORD record
- ord-9fefe27595f644c6b992e7483168bbc6
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03957889
Reaction notes
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