tert-Butyl peroxybenzoate → 10-Sulfostearic acid

HRID 2406852Notes

Reaction equation

HRID 2406852 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[S:21](S([O-])=O)([O-:24])(=[O:23])=[O:22].[Na+].[Na+].[OH-].[Na+].C1C(C(OOC(C)(C)C)=O)=CC=CC=1>O.C(O)(C)C>[S:21]([CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19])([OH:24])(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 11966tert-Butyl peroxybenzoate2×HCID 14798Sodium HydroxideHCID 445639Oleic AcidHCID 656671Sodium Pyrosulfite

Product 1

HCID 8574888510-Sulfostearic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

Deionized water (150 ml), isopropyl alcohol (200 ml) and oleic acid (43.78 g, 0.155 mol) were placed in a 1.0 liter flask equipped with stirrer, additional funnel, reflux condenser, thermometer and a gas inlet tube. To the additional funnel was added a premix which contained 15.2 g (0.08 mol) of sodium metabisulfite (Na2S2O5) and 1.28 g of NaOH in 55 g of water. The whole device was bubbled gently with nitrogen. After heating to reflux (82° C.), a small portion of t-butyl perbenzoate (out of total amount of 0.5 g, 2.5 mmol) was added to the flask. Then the Na2S2O5/NaOH premix was added through the addition funnel continuously over the course of five hours. The remaining t-butyl perbenzoate was also added in portions during this time.

Workup

  1. customequipped with stirrer, additional funnel
  2. temperaturereflux condenser
  3. additionTo the additional funnel was added
  4. additiona premix which
  5. customThe whole device was bubbled gently with nitrogen
  6. temperatureAfter heating
  7. additionwas added through the addition funnel continuously over the course of five hours

Sources & evidence

ORD record
ord-92a4cf62cb3f4fd481aeb80fa8f0c466
Source dataset
uspto-grants-2014_08
Patent number
US08809392B2

Reaction notes

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