Sulfuric Acid → Benzenesulfonic acid, 3-(diphenylphosphino)-, sodium salt (1:1)

HRID 1823711Notes

Reaction equation

HRID 1823711 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[C:6]1([P:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+:26]>CC(C)CC(=O)C>[C:19]1([P:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:13]2[CH:14]=[C:15]([S:1]([O-:3])(=[O:5])=[O:2])[CH:16]=[CH:17][CH:18]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.[Na+:26]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 11776TriphenylphosphineHCID 14798Sodium Hydroxide

Product 1

HCID 23668331Benzenesulfonic acid, 3-(diphenylphosphino)-, sodium salt (1:1)

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
25 °C

Procedure

A 300-ml three-necked flask equipped with a thermometer, stirrer, dropping funnel and nitrogen inlet and outlet lines was charged with 110 g (1.12 moles) of concentrated sulfuric acid and 60 g (0.23 mole) of triphenylphosphine, and the air in the flask was replaced with nitrogen. To the contents with stirring 220 g of fuming sulfuric acid (content of sulfur trioxide: 25% by weight; moles of sulfur trioxide: 0.69 mole) was added dropwise over 1 hour, while the inside temperature was maintained at 25° C. After completion of the dropping, stirring was continued for 12 hours at an inside temperature of 25° C. The reaction mixture obtained was added dropwise onto 1.8 kg of ice water under an atmosphere of nitrogen and hydrolyzed and diluted. To the obtained aqueous solution, 1.5 liters of 4-methyl-2-pentanone was added at a room temperature and sufficiently mixed. After the mixture had been allowed to stand still, the 4-methyl-2-pentanone layer was separated. To the 4-methyl-2-pentanone layer thus obtained, 120 ml of a 5% by weight aqueous sodium hydroxide solution was added dropwise under an atmosphere of nitrogen, while the inside temperature was maintained at 25° C., to neutralize it. The aqueous layer was taken out from the reaction mixture, washed with 100 ml of 4-methyl-2-pentanone and again taken out by separation. The layer was condensed at 80° C. to a volume of 80 ml and then allowed to cool, to precipitate crystals. The crystals precipitated were separated by filtration and vacuum-dried at 60° C., 0.67 kPa (5 mmHg) for 2 hours, to yield 35 g of a white crystalline sodium 3-(diphenylphosphino)benzenesulfonate dihydrate.

Workup

  1. customA 300-ml three-necked flask equipped with a thermometer, stirrer
  2. additionwas added dropwise over 1 hour, while the inside temperature
  3. customThe reaction mixture obtained
  4. additionhydrolyzed and diluted
  5. additionsufficiently mixed
  6. customthe 4-methyl-2-pentanone layer was separated
  7. customTo the 4-methyl-2-pentanone layer thus obtained
  8. temperaturewas maintained at 25° C.
  9. washwashed with 100 ml of 4-methyl-2-pentanone
  10. customagain taken out by separation
  11. customcondensed at 80° C. to a volume of 80 ml
  12. temperatureto cool
  13. customto precipitate crystals
  14. customThe crystals precipitated
  15. customwere separated by filtration
  16. customvacuum-dried at 60° C.
  17. wait0.67 kPa (5 mmHg) for 2 hours

Sources & evidence

ORD record
ord-444df6e759804c7e95fb4494dfa183ef
Source dataset
uspto-grants-2006_05
Patent number
US07041619B2

Reaction notes

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