Terephthalic Acid → 1,4-Dicyanobenzene
Reaction equation
[C:1](O)(=O)[C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][CH:3]=1.C([O-])(=O)C1C=CC(C([O-])=O)=CC=1.[NH4+:25].[NH4+:26]>[Ti].O>[C:1](#[N:26])[C:2]1[CH:10]=[CH:9][C:5]([C:6]#[N:25])=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 280 °C
Procedure
To a two-liter all-titanium stirred autoclave is added 146.19 g. (0.88 moles) of terephthalic acid, 24.02 g. (0.12 moles) of diammonium terephthalate and 1000 ml. of water. This mixture is heated with stirring to 280° C and held at this temperature for approximately one hour. The resultant equilibrated mixture represents the hydrolyzate obtained by the non-catalytic hydrolysis of terephthalonitrile which would result from the removal, as ammonia, of 88 percent of the total available nitrogen from a one molal solution of terephthalonitrile. That this is so is clearly evident from the hydrolysis equilibria of a terephthalonitrile hydrolysis system which are discussed above. The reactor is then rapidly cooled to ambient temperature and sufficient NaOH is added to the contents of the reactor to effect complete solution at room temperature. An excess of H2SO4 is then added to effect precipitation of the terephthalic acid product. After filtration, thorough washing and drying, a sample of the acid is submitted for determination of parts per million (by weight) of nitrogen. The value of 2400 ppm corresponds to 2.84 mole percent terephthalamic acid.
Workup
- temperatureThis mixture is heated
Sources & evidence
- ORD record
- ord-4c493505c9c947ffbf47436bee9e3087
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04069248
Reaction notes
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