107-71-1 Usage
Description
tert-Butyl peroxyacetate, also known as TBPA, is an organic peroxide used as a polymerization initiator. It is a clear solution that is sensitive to heat and must be stored with stringent temperature control measures to mitigate its explosion hazard. The peroxide is often mixed with an inert solid to further reduce the risk of explosion.
Uses
Used in Polymer Industry:
tert-Butyl peroxyacetate is used as a polymerization initiator for vinyl monomers, facilitating the production of polyethylene and polystyrene. Its effectiveness in initiating polymerization reactions makes it a valuable component in the manufacturing process of various plastics.
Used in Inorganic Synthesis:
In the field of inorganic chemistry, tert-Butyl peroxyacetate is employed to initiate polymerization and inorganic syntheses. Its ability to initiate reactions contributes to the formation of various inorganic compounds.
Used in Pharmaceutical Industry:
tert-Butyl peroxyacetate allows for the direct copper-catalyzed acetoxylation of β-lactams at the 4-position. This application is particularly useful in the synthesis of certain pharmaceutical compounds, as it enables a more direct and efficient method for modifying the structure of β-lactams.
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.LD50 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 107-71-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 107-71:
(5*1)+(4*0)+(3*7)+(2*7)+(1*1)=41
41 % 10 = 1
So 107-71-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O3/c1-5(7)8-9-6(2,3)4/h1-4H3
107-71-1Relevant articles and documents
EFFECT OF THE STRUCTURES OF HYDROPEROXIDES ON THE KINETICS OF THEIR ACETYLATION BY ACETIC ANHYDRIDE
Antonovskii, V. L.,Zhitina, L. V.,Yanaeva, O. K.,Emelin, Yu. D.
, p. 2356 - 2358 (1982)
-
Preassociating α-nucleophiles based on β-cyclodextrin. Their synthesis and reactivity
Martin, Kristy A.,Mortellaro, Mark A.,Sweger, Robert W.,Fikes, Lewis E.,Winn, David T.,Clary, Scott,Johnson, Morgan P.,Czarnik, Anthony W.
, p. 10443 - 10448 (1995)
Methods are reported for the attachment of α-nucleophiles to the primary and secondary sides of the cyclodextrin cavity. Six new materials have been prepared in which βCD has been modified by hydrazine, hydroxylamine, oxime, and hydroperoxide functionalities. Transacylating studies with p-NPA have demonstrated that the primary-side hydroxylamine shows the highest reactivity with a 1900-fold increase in rate over βCD at pH 6.5. Other α-nucleophiles show less remarkable rate increases in this system but, in some cases, demonstrate hydrogen-bonding to the cyclodextrin rim and inhibition kinetics.
Oxidation of β-dicarbonyl compounds with tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate
Stepovik,Gulenova,Kalacheva,Potkina, A. Yu.
, p. 550 - 558 (2011)
Oxidation of β-dicarbonyl compounds with tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate (benzene, 20°C) involves the activated methylene group with intermediate formation of trioxo derivatives and is accompanied by decomposition of carbon skeleton. The oxidation products are carbon dioxide, carboxylic acids, and tert-butyl and peroxy esters derived from the latter.
Koenig,T.,Deinzer,M.
, p. 7014 - 7019 (1968)
Brandes,Blaschette
, p. C33 (1975)
Polymerization Mechanism of Styrene Initiated by 2,2-Bis(t-butyldioxy)alkanes
Watanabe, Yasumasa,Ishigaki, Hideyo,Okada, Hiroshi,Suyama, Shuji
, p. 1231 - 1234 (1991)
The radical polymerization mechanism of styrene initiated by 2,2-bis(t-butyldioxy)alkanes (1) has been studied in benzene.The decomposition products of 1 are acetone, alkyl methyl ketone, t-butyl alcohol, and t-butyl peracetate.Styrene monomer converts to polystyrene along with styrene oxide.The peroxides 1 cleave homolytically at one of dioxy bonds to yield intermediate alkoxy radicals with α-t-butyldioxy group, which undergo β-scission to afford t-butyldioxy or alkyl radicals.The resulting t-butyldioxy radical reacts with styrene to form 2-(t-butyldiox)-1-phenylethyl radical, which decomposes subsequently to styrene oxide and t-butoxyl radical via γ-scission.Alternatively, a part of t-butyldioxy radical adds to styrene to afford polystyrene containing dioxy bond.
Amide bond formation through iron-catalyzed oxidative amidation of tertiary amines with anhydrides
Li, Yuanming,Ma, Lina,Jia, Fan,Li, Zhiping
, p. 5638 - 5646 (2013/07/26)
A general and efficient method for amide bond synthesis has been developed. The method allows for synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl2 as catalyst and tert-butyl hydroperoxide in water (T-Hydro) as oxidant. Mechanistic studies indicated that the in situ-generated α-amino peroxide of tertiary amine and iminium ion act as key intermediates in this oxidative transformation.