1,2,4-Trichlorobenzene → 2,4,5-Trichlorobenzenesulfonic acid

HRID 652306Notes

Reaction equation

HRID 652306 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14].C(=O)=O.Cl.ClC1C(Cl)=C(Cl)C=CC=1.[OH-].[Na+]>O>[Cl:13][C:10]1[CH:9]=[C:8]([Cl:14])[C:7]([Cl:6])=[CH:12][C:11]=1[S:2]([OH:5])(=[O:4])=[O:3]

Participants

8

Reactant 6

HCID 131,2,4-TrichlorobenzeneHCID 280Carbon DioxideHCID 313Hydrochloric Acid2×HCID 68951,2,3-TrichlorobenzeneHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid

Product 1

HCID 807862,4,5-Trichlorobenzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
120 °C

Procedure

119 g (1.0 mol) of technical grade chlorosulfonic acid were added dropwise, under stirring, to 218 g (1.2 mol) of technical grade 90% strength 1,2,4-trichlorobenzene over a period of time of about one hour. The reaction was permitted to proceed at 150° to 160° C. for three hours. During the reaction a slow stream of dried air or dried carbon dioxide was passed through the reaction mixture. The resulting hydrogen chloride of reaction was transferred with the gas stream into a receiving flask containing water. The hydrochloric acid trapped in the receiving flask constituted about 96% of theoretical. The reaction mixture, after being cooled to 120° C., was mixed with 200 ml of water. Steam was then charged therein to remove excess trichlorobenzene. 37 g (0.2 mol) of trichlorobenzene were recovered. Water was added to the reaction mixture to provide a total volume of 700 g which was then titrated with sodium hydroxide solution.

Workup

  1. customwas transferred with the gas stream into a receiving flask
  2. additionSteam was then charged
  3. customto remove excess trichlorobenzene
  4. customto provide a total volume of 700 g which

Sources & evidence

ORD record
ord-ac0c1cd13b374c9f8c8ee8fc8d66ca59
Source dataset
uspto-grants-1987_06
Patent number
US04670610

Reaction notes

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