Chemical Properties
clear solution
Uses
Allows the direct copper catalyzed acetoxylation of β-lactams at the 4-position.
Uses
It is used to initiate polymerization, and inorganic syntheses.
Uses
Polymerization initiator for vinyl monomers,
manufacture of polyethylene and polystyrene.
General Description
tert-Butyl peroxyacetate is sensitive to heat. Storage of tert-Butyl peroxyacetate must be done so with stringent temperature control measures. It's explosion hazard is also mitigated by mixing the peroxide with an inert solid.
Reactivity Profile
tert-Butyl peroxyacetate explodes with great violence when rapidly heated to a critical temperature; pure form is shock sensitive and detonable [Bretherick 1979 p. 602]. Upon contact with organic matter, t-butyl peroxyacetate can ignite or give rise to an explosion [Haz. Chem. Data 1973 p. 77].
Hazard
Flammable, dangerous fire risk. Oxidizer.
Health Hazard
Mild skin and eye irritant. Its toxicity is low,both via inhalation and ingestion routes.
LD
50 value, oral (rats): 675 mg/kg.
Fire Hazard
The pure compound is highly reactive and
oxidizing, and sensitive to heat and shock.
A 75% solution in benzene or mineral
spirits is the maximum assay that is
sold commercially. Its benzene solution at
this concentration is reactive, oxidizing, and
flammable. The flash point varies depending
on the solvent; the autoignition temperature
not reported; the self-accelerating decomposition
temperature is 93°C (199.4°F).
t-Butyl peroxyacetate forms an explosive
mixture with air, explosive range not
reported. It can ignite or explode when
in contact with combustible organic compounds.
Fire-extinguishing agent: water from
a sprinkler from an explosion-resistant location;
keep the containers cool.
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
ingestion. Mildly toxic by inhalation.
Moderate skin and eye irritant. A shockand
heat-sensitive explosive. Dangerous fire
hazard when exposed to heat, flame,
reducing agents. To fight fire, use dry
chemical, alcohol foam, spray and mist.
When heated to decomposition it emits
acrid smoke and fumes. See also
PEROXIDES, ORGANIC; and ESTERS
storage
Store in a cool and well-ventilated placeisolated from other chemicals; protect fromphysical damage. It is shipped in glass andearthenware containers not exceeding 7 lb,inside a wooden or fiberboard box.
Purification Methods
Wash the ester with NaHCO3 from a *benzene solution, then redistil to remove *benzene [Kochi J Am Chem Soc 84 774 1962]. Handle with adequate protection due to possible EXPLOSIVE nature. [Beilstein 2 IV 391.]
References
[1] J. Wenzel, Sunggyu Lee. “Tert-butyl peroxyacetate initiated semibatch polymerization of 1,1-difluoroethylene in supercritical carbon dioxide.” Polymer Engineering and Science 16 1 (2016): 435–440.
[2] V. A. Donchak, R. S. Yur'ev, S. A. Voronov. “New synthesis of tert-butyl peroxycarboxylates.” Russian Journal of Organic Chemistry 42 4 (2006): 487–490.
