Hydrogen Peroxide → HCID 14574133, compound

Temperature

15 °C

Attempted peroxidation of β-n-hexyladipic acid prepared as described in Example II resulted in an uncontrollable exothermic reaction. Thus, it was necessary to further purify the starting material before it could be successfully peroxidized. β-n-hexyladipic acid, (100 g) was dissolved in dichloromethane (500 ml) and washed with 25% sulfuric acid (3×150 ml), 5% sodium bicarbonate (3×100 mls), and distilled water (2×100 ml). The dichloromethane solution was dried over anhydrous magnesium sulfate after which the solvent was removed on a rotary evaporator leaving a clear oil which was crystallized from hexane to afford a white waxy solid (76.4 g). The purified β-n-hexyladipic acid (70.0 g, 0.304 mol) and 98% methanesulfonic acid (149 g, 1.55 mol) were added to a beaker and cooled to 15° C. 70% hydrogen peroxide (59.14 g, 1.74 mol) was added at a rate which maintained the temperature of about 30° C. while constantly stirring the suspension using a magnetic stirrer. After the addition was complete (about 10 minutes), the suspension was stirred at room temperature for an additional 1 hour, 50 minutes, which resulted in a clear solution. The solution was poured into cold distilled water (500 ml) and extracted with dichloromethane (1×300 ml, 2×250 ml). The dichloromethane solution was in turn extracted with 5% sodium sulfate solution 1×300 ml, 2×200 ml), dried over anhydrous magnesium sulfate after which the solvent was removed on a rotary evaporator. The oily residue was recrystallized from toluene to yield β-n-hexyldiperoxyadipic acid as a powdery white solid (49.7 g, mp 51.5°-52.5° C.; %AvO=11.6, theory=12.2; HPLC, C18ODS column, 67% methanol solvent, retention time: 5.84 minutes, diperxoy acid, relative peak area 96%, 10.00 min, diacid, relaive peak area 4%).

1. temperaturemaintained the temperature of about 30° C.
2. additionAfter the addition
3. custom(about 10 minutes)
4. stirringthe suspension was stirred at room temperature for an additional 1 hour, 50 minutes
5. customwhich resulted in a clear solution
6. additionThe solution was poured
7. distillationinto cold distilled water (500 ml)
8. extractionextracted with dichloromethane (1×300 ml, 2×250 ml)
9. extractionextracted with 5% sodium sulfate solution 1×300 ml, 2×200 ml),
10. dry with materialdried over anhydrous magnesium sulfate after which the solvent
11. customwas removed on a rotary evaporator
12. customThe oily residue was recrystallized from toluene

ORD record

ord-abac811b0bd9484c870b950dcb6da779

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876046