Hydrochloric Acid → 2-Carboxy-5-nitrobenzenesulfonic acid potassium salt

HRID 365953

Reaction equation

HRID 365953 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([OH:14])(=[O:13])=[O:12].[OH-:15].[K+:16].Cl[O-:18].[Na+].ClCl.Cl>>[K+:16].[C:1]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:14])(=[O:13])=[O:12])([OH:18])=[O:15]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 84582-Methyl-5-nitrobenzenesulfonic acidHCID 14797Potassium Hydroxide4×HCID 24526ChlorineHCID 23665760Sodium Hypochlorite

Product 1

HCID 453588752-Carboxy-5-nitrobenzenesulfonic acid potassium salt

Conditions

Temperature
65 °C

Procedure

27.2 g of 79.8% strength 2-methyl-5-nitrobenzenesulfonic acid (0.1 mol) were added to a mixture of 10.1 ml of 40% strength aqueous potassium hydroxide (0.1 mol) and 141 ml (0.3 mol) of aqueous sodium hypochlorite. The resulting suspension was heated to 65° C. and, at this temperature, admixed with 23 ml of 40% strength aqueous potassium hydroxide (0.23 mol) at a rate of 0.04 ml/min. After the addition was complete, the mixture was cooled to 0° C. and then admixed with 12.24 g (0.3 mol) of KOH. Over a period of 30 min, 10.64 g (0.15 mol) of chlorine gas were then introduced at this temperature. The temperature was then increased to 65° C., aqueous KOH (40% strength, 9.0 ml, 0.9 mol) was added at 0.04 ml/min and the mixture was subsequently stirred at 65° C. for another 2 hours. After cooling to 50° C., the mixture was acidified dropwise with concentrated hydrochloric acid (37% strength, 18 ml, 0.22 mol) at 50° C. over a period of 1 hour, cooled to 15-20° C. while passing through nitrogen gas, thus removing remaining chlorine gas, and stirred at 15-20° C. for another 2 hours. The product 2-carboxy-5-nitrobenzenesulfonic acid monopotassium salt was obtained, after filtration and drying at 75° C./100 mbar as a white powder; yield: 31 g; 76.5% pure product (83.1 % of theory).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was cooled to 0° C.
  3. temperatureThe temperature was then increased to 65° C.
  4. temperatureAfter cooling to 50° C.
  5. temperaturecooled to 15-20° C.
  6. customthus removing
  7. stirringstirred at 15-20° C. for another 2 hours

Sources & evidence

ORD record
ord-3e197890e07944bfa3a0f24103777768
Source dataset
uspto-grants-2000_10
Patent number
US06127572

Linked notes

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