Tert-Butyl Peracetate

Abstract

[107-71-1] C6H12O3 (MW 132.16) InChI = 1S/C6H12O3/c1-5(7)8-9-6(2,3)4/h1-4H3 InChIKey = SWAXTRYEYUTSAP-UHFFFAOYSA-N (radical initiator; often used in the presence of a metal catalyst or photoactivator; free radical initiator for polymer synthesis; common reagent in the metal-mediated acetoxylation of activated CH bonds) Alternate Names: peroxyacetic acid, tert-butyl ester; acetyl tert-butyl peroxide; tert-butyl peroxyacetate; ethaneperoxoic acid, 1,1-dimethylethyl ester; Esperox 12MD; Kayabutyl A; Kayabutyl A 50T; Luperox 7M75 or 7M50; Lupersol 70; NSC 118417; Perbutyl A; Trigonox F; Trigonox F-C 50. Physical Data: commercially available as a solution (typically in aliphatic hydrocarbons, 50–75 wt%); colorless to slight yellow liquid; density = 0.83 g mL−1 at 25 °C; flash point = 37 °C. Solubility: soluble in most organic solvents. Highly soluble in hydrocarbon, ethereal, or chlorinated solvents. Preparative Methods: acylation of a tert-butyl hydroperoxide with acetyl chloride or acetic anhydride.1 It can also be synthesized from tert-butyl hydroperoxide and acetic acid in the presence of trifluoroacetic anhydride.2 Handling, Storage, and Precautions: as with other organic peroxides, significant care should be taken to minimize rapid, exothermic decomposition that leads to violent and potentially harmful reactions. Decomposition can be triggered by heat, light, and metal contaminants.3 tert-Butyl peracetate has a detected onset temperature of 102 °C and a heat of decomposition of −201 kJ mol−1.4 Recommended storage in a tightly sealed container at 4–23 °C away from heat sources. Contact with skin and eyes or by inhalation should be avoided.