Sulfuric Acid → 4-Cyclohexylbenzenesulfonic Acid Sodium Salt

HRID 34883

Reaction equation

HRID 34883 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:13](=O)(=[O:16])([OH:15])[OH:14].OS(O)(=O)=O.O=S(=O)=O.[Na+:27].[Cl-]>>[Na+:27].[CH:7]1([C:1]2[CH:2]=[CH:3][C:4]([S:13]([O-:16])(=[O:15])=[O:14])=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 13229CyclohexylbenzeneHCID 24681Fuming sulfuric acid

Product 1

HCID 236948934-Cyclohexylbenzenesulfonic Acid Sodium Salt

Conditions

Temperature
70 °C

Procedure

Cyclohexyl benzene (500 gm, 3.12M) is stirred in a five liter 3-necked flask equipped with a condenser and a thermowatch, and is warmed to 70° C. Sulfuric acid (381 gm, 3.74M) and 30% oleum (38.2 gm) are added dropwise to the stirred reaction at a rate sufficient to maintain a temperature of approximately 70°-75° C. When the addition is complete, the reaction is aged at 70° C. for three hours and then cooled. The resulting reaction mixture, which is deep red in color, then is drowned in two liters of a saturated NaCl solution that is cooled to approximately 5° C. The solid precipitated in the salt solution then is filtered and washed with hexane, following which the precipitate is dried in a vacuum oven at 75° C.

Workup

  1. customequipped with a condenser
  2. temperatureto maintain a temperature of approximately 70°-75° C
  3. additionWhen the addition
  4. temperaturecooled
  5. customThe resulting reaction mixture, which
  6. temperatureis cooled to approximately 5° C
  7. customThe solid precipitated in the salt solution
  8. filtrationthen is filtered
  9. washwashed with hexane
  10. customis dried in a vacuum oven at 75° C.

Sources & evidence

ORD record
ord-b354d6fe8f5847e5938ace62ebb51d20
Source dataset
uspto-grants-1988_08
Patent number
US04764239

Linked notes

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