Hydrogen Peroxide → HCID 15774871, compound

Temperature

25 °C

To a 150 mL beaker equipped with a support clamp, ice bath, alcohol thermometer, mechanical stirrer, and dropping funnel were charged 22.03 g (0.1 mole) of powdered 3-(cyclohexylsulfonyl)propionic acid and 29.8 mL of 82 wt. % aqueous H2SO4. After a few minutes mixing at ambient temperature, a uniform slurry was obtained. To the dropping funnel was charged a solution prepared by adding 33.3 mL of 95.5% H2SO4 to 17.0 mL of 50% H2O2 (0.3 mole, 3 fold excess) with stirring and cooling to maintain ≤30° C., with final cooling to 25° C. With agitation, the mixture in the dropping funnel was added to the beaker over a 10 minute period, the temperature rising to 27° C. The ice bath was not applied because the heat evolution was so small. The mixture was agitated for another 130 minutes, the temperature gradually declining to 26.5° C. Most of the solids dissolved. The mixture was then contacted with ten 25-30 mL portions of methylene chloride at ambient temperature in an effort to recover the product by direct extraction into the methylene chloride. The combined extracts were washed with pH 5 phosphate buffer solution, then washed with water, partially evaporated, mixed with a weighed amount of boric acid, and dried. The weight and active oxygen analysis of this product showed that only 3.57 g of the organic product had been recovered by extraction (~15% of theory) and that its activity was 91.1% of that for the pure peracid. The crude reaction product remaining after methylene chloride extraction was mixed with 100 mL of cold pH 5 buffer with agitation and ice cooling, resulting in immediate formation of a large amount of white solids. The slurry was filtered at 15°-20° C. and the solids were washed on the filter with two 100 mL portions of cold buffer followed by 100 mL cold water. The resulting product was mixed with boric acid and dried and then blended uniformly with most of the product recovered by extraction. The resulting final product weighed about 30 g and had an active oxygen content of 3.27% (boric acid content roughly 47%). The calculated active yield was 61% of theory. (Equipment, analysis, and yield calculation were as described in Example 3.)

1. custommechanical stirrer, and dropping
2. additionAfter a few minutes mixing at ambient temperature
3. customa uniform slurry was obtained
4. additionTo the dropping funnel was charged a solution
5. customprepared
6. temperaturecooling
7. temperatureto maintain ≤30° C.
8. additionWith agitation, the mixture in the dropping funnel was added to the beaker over a 10 minute period
9. customrising to 27° C
10. stirringThe mixture was agitated for another 130 minutes
11. customgradually declining to 26.5° C
12. dissolutionMost of the solids dissolved
13. customto recover the product
14. extractionby direct extraction into the methylene chloride
15. washThe combined extracts were washed with pH 5 phosphate buffer solution
16. washwashed with water
17. custompartially evaporated
18. additionmixed with a weighed amount of boric acid
19. customdried
20. customhad been recovered by extraction (~15% of theory) and that its activity
21. customThe crude reaction product
22. extractionafter methylene chloride extraction
23. additionwas mixed with 100 mL of cold pH 5 buffer with agitation and ice cooling
24. customresulting in immediate formation of a large amount of white solids
25. filtrationThe slurry was filtered at 15°-20° C.
26. washthe solids were washed on the
27. filtrationfilter with two 100 mL portions of cold
28. additionThe resulting product was mixed with boric acid
29. customdried
30. customrecovered by extraction
31. custom(Equipment, analysis, and yield calculation were as described in Example 3.)

ORD record

ord-9700074f0a8243bcb006f56135df9fcc

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04758369