Phenol → 4-Hydroxybenzenesulfonic acid

HRID 1381481Notes

Reaction equation

HRID 1381481 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[C:6]([OH:16])(=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]C(C)C.C1(O)C=CC=CC=1>>[CH:7]1[C:6]([OH:16])=[CH:11][CH:10]=[C:9]([S:2]([OH:5])(=[O:4])=[O:3])[CH:8]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 24638Chlorosulfonic acidHCID 33635Isononanoic acid2×

Product 1

HCID 47654-Hydroxybenzenesulfonic acidYield 93.3%

Conditions

Temperature
95 °C

Procedure

In the equipment according to FIG. 1, a mixture of 178.8 g (1.53 mole) of chlorosulfonic acid and 136.5 g (0.86 mole) of isononanoic acid was placed into one of the two graduated funnels and a mixture of 143 g (1.52 mole) of phenol and 104 g (0.66 mole) of isononanoic acid was placed into the other, and the two mixtures were added under control to the continuous-flow reactor in such a way that the residence time was about 7 minutes. The total time for adding the starting compounds to the reactor under control was about 2 hours. The reactor, heated to 95° C. under thermostatic control, had a length of 60 cm and was packed with glass rings. Throughout the reaction period, 10 liters of nitrogen per hour were passed through the receiver and through the reactor. This gave a 93.3% yield of crude phenolsulfonic acid diluted with isononanoic acid, of the following composition:

Workup

  1. additionwere added under control to the continuous-flow reactor in such a way that the residence time
  2. additionThe total time for adding the starting compounds to the reactor under control
  3. waitwas about 2 hours
  4. customThroughout the reaction period, 10 liters of nitrogen per hour

Sources & evidence

ORD record
ord-96275ed0b131493e8ecd5e0066a69d02
Source dataset
uspto-grants-1989_02
Patent number
US04803015

Reaction notes

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