Nitric Acid → 4,4'-propane-2,2-diylbis(2-nitrophenol)
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([C:17]2[CH:22]=[C:21]([N+]([O-])=O)[C:20]([OH:26])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=2)([CH3:16])[CH3:15])[CH:7]=[C:8]([N+]([O-])=O)[C:9]=1[OH:10])([O-:3])=[O:2].[N+](C1C(O)=C([N+]([O-])=O)C([N+]([O-])=O)=C(C(C2C=CC(O)=CC=2)(C)C)C=1[N+]([O-])=O)([O-])=O.OC1C=CC(C(C2C=CC(O)=CC=2)(C)C)=CC=1.[N+]([O-])(O)=O.ClC(Cl)C>>[OH:26][C:20]1[CH:21]=[CH:22][C:17]([C:14]([C:6]2[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)([CH3:16])[CH3:15])=[CH:18][C:19]=1[N+:27]([O-:29])=[O:28]Participants
Procedure
This invention uses 2,2-bis(3,5-dinitro-4-hydroxyphenyl) propane as a polymerization inhibitor. For the sake of convenience, this compound will also be called tetranitrobisphenol A. A method of synthesizing said compound is described in Stroganov et al, Zh. Org. Khim 1973, 9(8), 1713-17, and Smirnov and Stroganov USSR Pat. No. 237,860 (1969). Thus, 2,2-bis(4-hydroxyphenyl)propane is nitrated with a concentrated nitric acid (for instance 70% HNO3) in a suitable solvent such as dichloroethane to afford primarily 2,2-bis(4-hydroxy-3-nitro-phenyl)propane. A typical reaction condition for this step is 20°-30° C. for 2 hours. Without isolating the product, a mixture of sulfuric acid and nitric acid (for instance, 42% H2SO4, 50% HNO3, and 8% H2O) is added to the reaction mixture and nitration continued to afford tetranitrobisphenol A. A typical reaction condition for the second step is 40° C. for 2 hours. The desired product is isolated by a routine procedure.
Workup
- customA method of synthesizing
Sources & evidence
- ORD record
- ord-4b02d197d71b4c8b879e2830e0fb6180
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04376678
Reaction notes
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