Water → p-Toluenesulfonic acid

HRID 1638361Notes

Reaction equation

HRID 1638361 reaction equation
O.O.[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1>C1(C)C(C)=CC=CC=1>[C:3]1([CH3:13])[CH:4]=[CH:5][C:6]([S:9]([OH:12])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Into a four-necked flask provided with a stirrer, a thermometer, a constant water receiver with a reflux condenser and a nitrogen gas inlet was charged a mixture of 190.0 parts of p-toluene sulfonic acid monohydrate and 266.0 parts of xylene. The temperature was raised while blowing nitrogen gas and then the stirring was continued at 140° C. for 2 hours to remove 18 parts of water. After the reaction mass was cooled in air, the nitrogen gas inlet was replaced with a dropping funnel and 250.0 parts of Kardula E10 was added dropwise through the dropping funnel for 30 minutes while stirring at room temperature. After the completion of the dropwise addition, the stirring was continued at room temperature for 4 hours, and the reaction was stopped at an acid value of involatile matter of not more than 1 to obtain an ester solution of p-toluene sulfonic acid esterified with equimole of Kardula E10 and having an effective component concentration (aromatic sulfonic acid) of 25%.

Workup

  1. customInto a four-necked flask provided with a stirrer
  2. temperatureThe temperature was raised
  3. customto remove 18 parts of water
  4. temperatureAfter the reaction mass was cooled in air
  5. customthe nitrogen gas inlet was replaced with a dropping funnel
  6. addition250.0 parts of Kardula E10 was added dropwise through the dropping funnel for 30 minutes
  7. additionAfter the completion of the dropwise addition
  8. waitthe stirring was continued at room temperature for 4 hours

Sources & evidence

ORD record
ord-2c002c65aadf4c6b804864ba33f82802
Source dataset
uspto-grants-1989_11
Patent number
US04879337

Reaction notes

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