Nitric Acid → Dimethyl nitroterephthalate
Reaction equation
[C:1]1([C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O.[N+:29]([O-])([OH:31])=[O:30]>>[N+:29]([C:3]1[CH:2]=[C:1]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:7]([O:9][CH3:10])=[O:8])([O-:31])=[O:30]Participants
Procedure
Czech Patent Specification No. 138,287 discloses a process for preparing 1-nitrobenzene-2-methoxycarbonyl-5-carboxylic acid. In this process, dimethyl benzene-1,4-dicarboxylate is nitrated in fuming sulfuric acid by means of a mixed acid of 20% strength oleum and 98% strength nitric acid; the dimethyl 1-nitrobenzene-2,5-dicarboxylate obtained is then first isolated and subsequently partially hydrolyzed by means of a large excess of 70% strength aqueous sulfuric acid. 1-Nitrobenzene-2-methoxycarbonyl-5-carboxylic acid precipitated in the acidic medium is then dissolved by means of sodium carbonate and reprecipitated by means of hydrochloric acid. In carrying out this process in industry, it suffers from the disadvantage that the waste water is very heavily polluted. The process moreover requires an additional isolating step as well as a purification operation, and it is impossible to prevent explosive dimethyl ether from forming from the methyl alcohol resulting in the hydrolysis of the ester group.
Sources & evidence
- ORD record
- ord-829c6671e76143399e6c9a5e65bfd807
- Source dataset
- uspto-grants-1985_03
- Patent number
- US04507491
Reaction notes
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