Hydrogen Peroxide → 3-(n-Decylsulfonyl)peroxypropionic acid

Temperature

40 °C

The product of Example 12 was converted to the corresponding carboxylic acid by alkaline hydrolysis followed by acidification and then to the corresponding sulfone carboxylic acid by oxidation in accordance with a procedure found in U.S. Pat. No. 3,857,875 to Brady et al. A stirred mixture of 5 g of 3-(n-decylsulfonyl)propionic acid and 50 mL of methanesulfonic acid was heated to 40±3° C. The 3-(n-decylsulfonyl)propionic acid dissolved only partially in the methanesulfonic acid at this temperature. Then 2.04 g of 90% hydrogen peroxide was added dropwise via pipette over ten minutes. Before the addition of the hydrogen peroxide was completed, the reaction mixture became thick from precipitation of a solid. After the addition of the 90% hydrogen peroxide was completed, the heating of the reaction mixture was continued at 40±3° C. until the reaction time totalled ninety minutes beginning at the start of the addition of the hydrogen peroxide. The reaction mixture was then cooled in an ice bath at 10° C. The solid was then filtered from solution using a coarse sinteredglass funnel, then transferred to a beaker containing 200 mL of ice water prepared from deionized water. The product was washed twice with ice water, filtered and dried to provide 4.63 g of the desired product (87.6% of theoretical based upon the weight of starting 3-(n-decylsulfonyl)propionic acid). The product was found to have 5.32% active oxygen. The product was stabilized with an equal weight of boric acid and put through a #30 polyethylene sieve which provided a particle size of less than 600 microns. The stabilized product contained 2.58% by weight active oxygen.

1. customthe reaction mixture became thick from precipitation of a solid
2. additionAfter the addition of the 90% hydrogen peroxide
3. temperaturethe heating of the reaction mixture
4. customwas continued at 40±3° C. until the reaction time
5. waittotalled ninety minutes
6. additionbeginning at the start of the addition of the hydrogen peroxide
7. temperatureThe reaction mixture was then cooled in an ice bath at 10° C
8. filtrationThe solid was then filtered from solution
9. additioncontaining 200 mL of ice water
10. customprepared from deionized water
11. washThe product was washed twice with ice water
12. filtrationfiltered
13. customdried

ORD record

ord-fcaa2c30e2eb4e489eb876054c7dcfd1

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04824591