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

HRID 1492073Notes

Reaction equation

HRID 1492073 reaction equation
[OH-:1].[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]>>[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O-:12])=[O:11])([OH:1])(=[O:6])=[O:5].[Na+:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-2×

Product 1

HCID 23668512Benzoic acid, 3-sulfo-, sodium salt (1:1)Yield 96.5%

Conditions

Temperature
100 °C

Procedure

The pH of 345 g of mother liquor from Example 1 is adjusted to 4 with about 60 g of sodium hydroxide. 300 ml of this solution are introduced together with 264.5 g of 3-(chlorosulfonyl)benzoic acid (water content: 25.7%) (corresponding to 196.5 g (0.89 mol) of 100% 3-(chlorosulfonyl)benzoic acid). 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 13.8 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). 192.6 g of sodium 3-sulfobenzoate are obtained with a purity of 96% and a sodium chloride content of 3.2% (corresponding to 184.9 g (0.83 mol) of 100% sodium 3-sulfobenzoate). The yield is 92.6% of theoretical.

Workup

  1. temperatureto cool over about 1 hour to 40° C
  2. temperatureSubsequently it is cooled with an ice bath to <5° C.
  3. stirringstirred for a further 30 minutes at this temperature
  4. filtrationThe precipitated product is filtered off with suction
  5. washwashed with 256 g of 5% strength sodium chloride solution
  6. customprepared from 13.8 g of sodium chloride and 243.2 g of water
  7. temperaturecooled to 5° C., in two portions
  8. customThe filter cake is dried at 100° C./100 torr (13.16 kPa)

Sources & evidence

ORD record
ord-b0c917444ab44dedaf23177f3b4697ce
Source dataset
uspto-grants-1994_12
Patent number
US05371281

Reaction notes

Loading…