Acetic Acid → 1-Naphthalenesulfonic acid

HRID 1732490Notes

Reaction equation

HRID 1732490 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[S:11](=O)(=[O:14])([OH:13])[OH:12].C(O)(=O)C>C(OC(=O)C)(=O)C>[C:9]1([S:11]([OH:14])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 931Naphthalene2×HCID 1118Sulfuric Acid2×

Product 1

HCID 68121-Naphthalenesulfonic acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

128 g (1 mole) of naphthalene are dissolved in 102 g (1 mole) of acetic anhydride in an apparatus with a stirrer and a means for the supply of sulphuric acid, a dephlegmator, cooler and vacuum-receiver. Then 98 g (1 mole) of a 100% sulphuric acid are added to the solution of naphthalene in acetic anhydride for 60 minutes at a temperature of 60° C. The removal of the forming acetic acid is effected under vacuum under a residual pressure of 1 to 10 mm Hg. After discontinuation of distillation of acetic acid, i.e. on completion of the reaction of naphthalene sulphonation, there are obtained 208 g (1 mole) of naphthalene-α-sulphonic acid and 118 g (2 moles) of glacial acetic acid. The resulting naphthalene-α-sulphonic acid is poured to 224 g (4 moles) of a preliminary prepared melt of potassium hydroxide having a temperature of 180° C. under vigorous stirring. Then the melt temperature is raised to 285° C. for 5 minutes and the melt is maintained at this temperature for 5 minutes to complete the fusion process. On expiration of 10 minutes, the melt is cooled to a temperature of 80° C., diluted with 200 g of water and the resulting aqueous solution containing potassium α-naphtholate and potassium sulphite is supplied into a mixer provided with a cooling jacket, whereinto a solution of 98 g (1 mole) of sulphuric acid in 400 g of water has been preliminarily charged. Then the resulting mixture is cooled to a temperature of 10° C. and the precipitated α-naphthol is separated from the aqueous solution of the mixture of potassium sulphite, potassium sulphate and non-precipitated α-naphthol and β-naphthol by filtration. The yield of α-naphthol with a purity of 99.5% is 115 g (0.8 mole) as calculated for the employed naphthalene which corresponds to 80% of the theoretical value. The filtrate is treated with an equal volume of carbon tetrachloride and, after separation of the aqueous layer and distilling-off carbon tetrachloride, there are obtained 25 g (0.17 mole) of α-naphthol with a purity of 95%. The total yield of α-naphthol is 97% of the theoretical as calculated for the employed naphthalene.

Workup

  1. customThe removal of the forming acetic acid
  2. distillationAfter discontinuation of distillation of acetic acid, i.e.
  3. customon completion of the reaction of naphthalene sulphonation, there

Sources & evidence

ORD record
ord-73fb41dff9894cda940f7969534668c3
Source dataset
uspto-grants-1980_12
Patent number
US04237323

Reaction notes

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