Sulfuric Acid → 3-(Phenylsulphonyl)propiononitrile

HRID 1075136Notes

Reaction equation

HRID 1075136 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[C:11](#[N:14])[CH:12]=[CH2:13].S(=O)(=O)(O)O>O>[C:1]1([S:7]([CH2:13][CH2:12][C:11]#[N:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 824133-(Phenylsulphonyl)propiononitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

650 ml of water are introduced into the flask and are heated to 80° to 90° C., and 935 g (4 mols) of 70% strength sodium benzenesulphinate are added to the water. 215 g (4.04 mols) of acrylonitrile and 382 g (1.95 mols) of 50% strength sulphuric acid are then added simultaneously, in the course of about 1 hour at 100° C., at such a rate that the pH value remains at 6 to 7. The mixture is stirred for 30 minutes at 100° C. and the pH value is again readjusted. Excess acrylonitrile is distilled off over a Vigreux column in an azeotropic mixture with water at normal pressure, and 255 g of xylene are then added and the phases are separated at about 95° C. This is carried out by sucking off the lower aqueous phase with a suction tube. The salt precipitate remains for the most part in the flask. 800 ml of washing water is now stirred in at >95° C. and the phases are separated as described above. In this process most of the salt is dissolved, and the remainder does not interfere in the following reaction. A further 17 g of 3-phenylsulphonyl-propionitrile are isolated from the combined aqueous phases. 255 g (300 ml) of xylene are now added to the organic phase in the flask, at 95° to 100° C., and the remaining water is distilled off azeotropically with xylene (boiling point 92° C.) The remaining xylene is completely removed in vacuo at a trough temperature of 100° to 120° C. The trough now contains 730 g (94%) of 3-phenylsulphonyl-propionitrile in 97% purity, and 50 g of salt.

Workup

  1. temperatureare heated to 80° to 90° C.
  2. distillationExcess acrylonitrile is distilled off over a Vigreux column in an azeotropic mixture with water at normal pressure, and 255 g of xylene
  3. additionare then added
  4. customthe phases are separated at about 95° C
  5. stirring800 ml of washing water is now stirred in at >95° C.
  6. customthe phases are separated
  7. dissolutionIn this process most of the salt is dissolved
  8. customthe remainder does not interfere in the following reaction

Sources & evidence

ORD record
ord-4dbbbfa95daf45b288796b75112b253b
Source dataset
uspto-grants-1983_07
Patent number
US04395371

Reaction notes

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