Water → Benzoic acid, 3-sulfo-, sodium salt (1:1)

HRID 1492072Notes

Reaction equation

HRID 1492072 reaction equation
[Cl-].[Na+:2].Cl[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])(=[O:6])=[O:5].[OH2:16]>>[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O-:12])=[O:11])([OH:16])(=[O:6])=[O:5].[Na+:2]

Participants

4

Reactant 3

HCID 962WaterHCID 5234Sodium Chloride2×HCID 77641Benzoic acid, 3-(chlorosulfonyl)-2×

Product 1

HCID 23668512Benzoic acid, 3-sulfo-, sodium salt (1:1)Yield 90.9%

Conditions

Temperature
100 °C

Procedure

360 g of 26.4% strength sodium chloride solution, prepared from 95.0 g of sodium chloride and 265.0 g of water, and 332 g of crude 3-(chlorosulfonyl)benzoic acid (water content: 39.2%) (corresponding to 201.8 g (0.92 mol) of 100% 3-(chlorosulfonyl)benzoic acid) are introduced into a 1 l four-neck flask fitted with stirrer, internal thermometer and reflux condenser. The reaction mixture is heated to 100° C. and stirred for a further 45 minutes at this temperature. The mixture is then allowed to cool over about 1 hour to 40° C. Subsequently it is cooled with an ice bath to <5° C. and stirred for a further 30 minutes at this temperature. The precipitated product is filtered off with suction and washed with 256 g of 5% strength sodium chloride solution, prepared from 12.8 g of sodium chloride and 243.2 g of water and cooled to 5° C., in two portions. The filter cake is dried at 100° C./100 torr (13.16 kPa). 196.3 g of sodium 3-sulfobenzoate are obtained with a purity of 95% and a sodium chloride content of 3.9% (corresponding to 186.5 g (0.83 mol) of 100% sodium 3-sulfobenzoate). The yield is 90.9% of theoretical. 345 g of mother liquor and 318 g of wash liquor are produced.

Workup

  1. additionare introduced into a 1 l four-neck flask
  2. customfitted with stirrer
  3. temperatureinternal thermometer and reflux condenser
  4. temperatureto cool over about 1 hour to 40° C
  5. temperatureSubsequently it is cooled with an ice bath to <5° C.
  6. stirringstirred for a further 30 minutes at this temperature
  7. filtrationThe precipitated product is filtered off with suction
  8. washwashed with 256 g of 5% strength sodium chloride solution
  9. customprepared from 12.8 g of sodium chloride and 243.2 g of water
  10. temperaturecooled to 5° C., in two portions
  11. customThe filter cake is dried at 100° C./100 torr (13.16 kPa)

Sources & evidence

ORD record
ord-d1f714b24016425e87557c402c6bb613
Source dataset
uspto-grants-1994_12
Patent number
US05371281

Reaction notes

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