Sodium Hydroxide → HCID 19790452, compound

HRID 1656151Notes

Reaction equation

HRID 1656151 reaction equation
[Na].[OH-].[Na+].[CH2:4]([O:10][C:11](Cl)=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].ClC([O-])=O.C(=O)([O-])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](CCCCCC)[C:21]=1[S:32]([OH:35])(=[O:34])=[O:33]>CC(CC)=O.O>[C:11](=[O:12])([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:32]([OH:35])(=[O:33])=[O:34])[O:10][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 22466Hexyl chloroformateHCID 5360545SodiumHCID 21226386CarbonochloridateHCID 86746533HCID 86746533, compound

Product 1

HCID 19790452HCID 19790452, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
50 °C

Procedure

Into a reactor as described in Example 1 and with similar procedure there were charged 40.9 kg of water and, with agitation, 24.5 kg of sodium 4-phenolsulfonate. After an additional 10 minutes of agitation, there was added 9.7 kg of 50%, by weight, sodium hydroxide over a period of 15 minutes. There were then added 9.72 g of product and 68.1 kg of methylethyl ketone. After heating the mixture to 50° C. there was added 19.5 kg of n-hexylchloroformate over a period of 15 minutes. During addition of the chloroformate the batch temperature increased to about 65° C. and the reaction allowed to proceed with agitation for a period of 30 minutes at a temperature in the range of 65° C.-70° C. After completion of the reaction the mixture was cooled to below 50° C. and allowed to settle into two phases. The top organic layer containing n-hexylsulfophenyl carbonate was separated from the bottom saturated layer, and was washed with 22.72 kg of a 33 percent aqueous solution of sodium sulfate. After thorough mixing the mixture was allowed to settle. The top organic layer was separated from the bottom salt layer and the procedure with sodium sulfate repeated two more times. The organic layer was pan dried with vacuum. About 45.4 kg of n-hexyl sulfophenyl carbonate was obtained which contained 0.92 percent di-n-hexyl carbonate as indicated by analysis (gc) of a cyclohexane extract.

Workup

  1. customInto a reactor as described in Example 1 and with similar procedure there
  2. additionAfter an additional 10 minutes of agitation, there was added 9.7 kg of 50%
  3. temperatureincreased to about 65° C.
  4. customAfter completion of the reaction the mixture
  5. temperaturewas cooled to below 50° C.
  6. customwas separated from the bottom saturated layer
  7. washwas washed with 22.72 kg of a 33 percent aqueous solution of sodium sulfate
  8. additionAfter thorough mixing the mixture
  9. customThe top organic layer was separated from the bottom salt layer
  10. customdried with vacuum

Sources & evidence

ORD record
ord-bd501289a2574a1caeee4091c24d8af6
Source dataset
uspto-grants-1993_10
Patent number
US05252770

Reaction notes

Loading…