107-71-1

Basic information

• Product Name: tert-Butyl peroxyacetate
• Synonyms: Ethaneperoxoicacid,1,1-dimethylethylester;lupersol70;peroxyaceticacid,tert-butylester;t-Butylethaneperoxoicacid;t-butylperoxyacetate;tert-butyl;trigonoxf-c50;LUPEROX 7M50
• CAS NO: 107-71-1
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• EINECS: 203-514-5
• Product Categories: Organics;Free Radical Initiators;Organic Peroxides;Polymerization Initiators
• Mol File: 107-71-1.mol

Chemical Properties

• Melting Point: -20 °C
• Boiling Point: 184.08°C (rough estimate)
• Flash Point: 99 °F
• Appearance: Clear/Solution
• Density: 0.828 g/mL at 25 °C
• Vapor Pressure: 13.8mmHg at 25°C
• Refractive Index: n20/D 1.412
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• Water Solubility: 3.878g/L at 25℃
• CAS DataBase Reference: tert-Butyl peroxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl peroxyacetate(107-71-1)
• EPA Substance Registry System: tert-Butyl peroxyacetate(107-71-1)

Safety Data

• Hazard Codes: F,T,O,Xi
• Statements: 23/24/25-36/37/38-40-65-22-10-7-45-46
• Safety Statements: 16-26-36/37/39-45-62-47-14-7-53-3/7-36/37-35
• RIDADR: UN 3103 5.2
• WGK Germany: 2
• RTECS: SD8925000
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 107-71-1(Hazardous Substances Data)

Usage

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.]

InChI:InChI=1/C6H12O3/c1-5(7)8-9-6(2,3)4/h1-4H3

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 463-51-4 Ketene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 100-42-5 styrene 
• 4262-61-7 acetone di-tert-butylperoxyketal 
• 2167-23-9 2,2-bis(tert-butylperoxy)butane 
• 7735-97-9 2,2-Bis-tert-butylperoxy-3-methyl-butane 
• 4015-58-1 monochloroacetic acid anhydride 
• 600-14-6 2,3-Pentanedione 
• 556-91-2 aluminum tri-tert-butoxide 
• 98-82-8 Isopropylbenzene 
• 64-19-7 acetic acid 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 35926-04-6 3-acetoxy-1-hexene 
• 2442-10-6 oct-1-en-3-yl acetate 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 64918-12-3 2-acetoxy-4-benzoyl-1-oxa-4-azacyclohexane 
• 64918-13-4 2r,3t-diacetoxy-4-benzoyl-morpholine 
• 7204-29-7 trans-2-butenyl acetate 
• 6737-11-7 2-acetoxy-3-butene 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 103-54-8 cinnamyl acetate 
• 7204-36-6 (Z)-2-butene-1-yl acetate 
• 127756-72-3 4-acetoxy-1-(4-methoxyphenyl)azetidin-2-one 
• 75-91-2 tert.-butylhydroperoxide 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 

Relevant articles and documents

Reaction of zirconium alkoxides with tert-butyl hydroperoxide. Oxidative ability of the Zr(OBu-t)4-t-BuOOH system

Oxidation of the isopropoxy group in the Zr(i-PrO)4·i- PrOH complex involves both direct reaction with tert-butyl hydroperoxide and intermediate formation of zirconium peroxy compound. Zirconium tetra-tert-butoxide reacts with tert-bytyl hydroperoxide to form metal-containing peroxide and trioxide. Decomposition of the latter leads to oxygen evolution and is accompanied by radical formation. The alkoxyl and peroxyl radicals formed were identified by ESR spectroscopy. The nature of the oxidant (oxygen, zirconium-containing peroxide and-trioxide) in the Zr(OBu-t)4-t-BuOOH system is determined by the structure of the substrate molecule. Pleiades Publishing, Inc., 2006.

Preassociating α-nucleophiles based on β-cyclodextrin. Their synthesis and reactivity

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

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.

Reaction of triphenylantimony and triphenylbismuth with tert-butyl peracetate

Triphenylantimony and triphenylbismuth diacetates, Ph3M(OAc)2 (M = Sb, Bi), were obtained in 50-95percent yields by the reaction of triphenylantimony and triphenylbismuth with tert-butyl peracetate in the presence of acetic acid or acetic anhydride (molar

New synthesis of tert-butyl peroxycarboxylates

tert-Butyl peroxyacetate, tert-butyl peroxybutyrate, tert-butyl phenylperoxyacetate, and tert-butyl peroxyundecanoate were obtained in nearly quantitative yields by the esterification of the corresponding carboxylic acids with tert-butyl hydroperoxide in the presence of trifluoroacetic anhydride and pyridine in nonaqueous medium at 0-5°C. No tert-butyl peroxytrifluoroacetate was formed as a by-product during the process. A possible reaction mechanism is discussed. Pleiades Publishing, Inc., 2006.

Polymerization Mechanism of Styrene Initiated by 2,2-Bis(t-butyldioxy)alkanes

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

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.

Specific features of the reaction of vanadyl acetylacetonate with tert-butyl hydroperoxide

Reaction of vanadyl acetylacetonate with tert-butyl hydroperoxide (benzene, 20°C) at any molar ratio leads to the elimination of ligand and its oxidation mainly to CO2 and acetic acid. At the (acac)2VO: t-BuOOH ratio above 1:10 liberation of oxygen partially in the singlet state takes place.

Reaction of unsaturated esters with the oxidative system aluminum tri-tert-butoxide-tert-butyl hydroperoxide

Unsaturated esters containing double bonds in the acyl (methyl acrylate) or in the alcohol (vinyl and allyl acetates) fragments are cleaved under mild conditions (20°C) by the system aluminum tri-tert-butoxide-tert-butyl hydroperoxide to give tert-butyl esters of peroxycarboxylic acids and unsymmetrical aluminum alkoxides. The double bond in the acyl fragment is inert to this oxidation system. Vinyloxy- and allyloxy derivatives are oxidized to hydroxyethanal and (hydroxymethyl)oxirane, respectively. Carbon-hydrogen bonds are oxidized only in allyl acetate.

5-CYANO-10-HYDROXY-10,11-DIHYDRO-5H-DIBENZ[B,F]AZEPINE, THE PROCESSES FOR ITS PREPARATION AND FOR ITS CONVERSION INTO 5-CARBAMOYL-10-OXO-10, 11-DIHYDRO-5H-DIBENZ[B,F]AZEPINE OR INTO 5-CARBAMOYL-5H-DIBENZ[B,F]AZEPINE

5-Cyano-10-Hydroxy-10,11-Dihydro-5H-Dibenzi[b,f]azepine and the process for its preparation.