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

HRID 1492074Notes

Reaction equation

HRID 1492074 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][S:11](O)(=[O:13])=[O:12].O=S(=O)=O.[Cl-].[Na+:20]>>[S:11]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([O-:9])=[O:8])([OH:13])(=[O:12])=[O:10].[Na+:20]

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 5234Sodium ChlorideHCID 24681Fuming sulfuric acid

Product 1

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

Conditions

Temperature
130 °C

Procedure

122.1 g (1.0 mol) of benzoic acid are melted at 125° to 130° C. in a 1 l four-neck flask fitted with stirrer, internal thermometer and reflux condenser. Then 405 g of oleum are introduced over 30 minutes. Subsequently the reaction mixture is heated to 130° C. and stirred for a further 1 hour at this temperature. The reaction mixture is cooled and 1800 g (=1500 ml) of 26.4% strength sodium chloride solution are run in over 15 minutes. The reaction mixture is heated to 80° C. to 85° C. Then the mixture is allowed to cool to 50° C. while stirring. 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 (=250 ml) of 5% strength sodium chloride solution cooled to 5° C., in two portions. After drying, 204.4 g of sodium 3-sulfobenzoate are obtained with a purity of 96% and a sodium chloride content of 3% (corresponding to 196.3 g (0.88 mol) of 100% sodium 3-sulfobenzoate). 2342 g of effluent are produced.

Workup

  1. customfitted with stirrer
  2. temperatureinternal thermometer and reflux condenser
  3. temperatureThe reaction mixture is cooled
  4. customare run in over 15 minutes
  5. temperatureThe reaction mixture is heated to 80° C. to 85° C
  6. temperatureto cool to 50° C.
  7. stirringwhile stirring
  8. temperatureSubsequently it is cooled with an ice bath to <5° C.
  9. stirringstirred for a further 30 minutes at this temperature
  10. filtrationThe precipitated product is filtered off with suction
  11. washwashed with 256 g (=250 ml) of 5% strength sodium chloride solution
  12. temperaturecooled to 5° C., in two portions
  13. customAfter drying

Sources & evidence

ORD record
ord-1fc7611d570d4ef3b25fdbf9ffe5da12
Source dataset
uspto-grants-1994_12
Patent number
US05371281

Reaction notes

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