Quick Search

PRODUCTS

TERT-BUTYL PEROXYBENZOATE

TERT-BUTYL PEROXYBENZOATE

Tert-butyl peroxybenzoate (TBPB) is an organic compound with the formula C6H5CO2CMe3 (Me = CH3). 
Tert-butyl peroxybenzoate is the most widely produced perester. 
Tert-butyl peroxybenzoate is often used as a radical initiator in polymerization reactions, such as the production of LDPE from ethylene, and for crosslinking, such as for unsaturated polyester resins.

CAS: 614-45-9
European Community (EC) Number: 210-382-2

Molecular Formula: C11H14O3
Molecular Weight: 194.23

Odor: Mild aromatic odor
Boiling Point: 234 °F at 760 mmHg
Melting Point: 46 °F
Flash Point: 200 °F
Solubility: less than 1 mg/mL at 68 °F
Density: 1.04 at 77 °F
Vapor Pressure: 0.33 mmHg at 122 °F


Tert-butyl peroxybenzoate, [<= 50% with inert inorganic solid] is a clear, colorless to slightly yellow liquid with a mild, aromatic odor. 
Tert-butyl peroxybenzoate is also stored and transported as a mixture with inert solids and as a solvent slurry, to mitigate the explosion hazard.

Tert-butyl peroxybenzoate is a colorless to slightly yellow liquid with a mild aromatic odor. 
Tert-butyl peroxybenzoate is used as a polymerization initiator and as a chemical intermediate.

Properties
Tert-butyl peroxybenzoate, which is pale yellow, is exclusively encountered as a solution in solvents such as ethanol or phthalate.

As peroxo compound, Tert-butyl peroxybenzoate contains about 8.16 wt% of active oxygen and has a self accelerating decomposition temperature (SADT) of about 60 °C. 
The SADT is the lowest temperature at which self-accelerating decomposition in the transport packaging can occur within a week, and which should not be exceeded while storage or transportation.
Tert-butyl peroxybenzoate should therefore be stored between minimum 10 °C (below solidification) and maximum 50 °C. 
Dilution with a high-boiling solvent increases the SADT. 
The half-life of Tert-butyl peroxybenzoate, in which 50% of the peroxy ester is decomposed, is 10 hours at 104 °C, one hour at 124 °C and one minute at 165 °C. 
Amines, metal ions, strong acids and bases, as well as strong reducing and oxidizing agents accelerate the decomposition of Tert-butyl peroxybenzoate even in low concentrations.
However, Tert-butyl peroxybenzoate is one of the safest peresters or organic peroxides in handling.
The main decomposition products of tert-butyl peroxybenzoate are carbon dioxide, acetone, methane, tert-butanol, benzoic acid and benzene.

Production
A standard procedure for the preparation of peresters is the acylation of tert-butyl hydroperoxide with benzoyl chloride.
In the reaction a large excess of tert-butyl hydroperoxide is used and the hydrogen chloride formed is removed in vacuo whereby a virtually quantitative yield is obtained.

Applications
In polymer chemistry
Primarily, TBPB is used as a radical initiator, either in the polymerization of e.g. ethylene (to LDPE), vinyl chloride, styrene or acrylic esters or as so-called unsaturated polyester resins (UP resins).
The quantity used for the curing of UP resins is about 1-2%.

A disadvantage, particularly in the production of polymers for applications in the food or cosmetics sector, is the possible formation of benzene as a decomposition product which can diffuse out of the polymer (for example, an LDPE packaging film).

In organic chemistry
The protecting group 2-trimethylsilylethanesulfonyl chloride (SES-Cl) for primary and secondary amino groups is accessible by the reaction of vinyltrimethylsilane with sodium hydrogensulfite and Tert-butyl peroxybenzoate to the sodium salt of trimethylsilylethanesulfonic acid and the subsequent reaction with thionyl chloride to the corresponding sulfonyl chloride.

Tert-butyl peroxybenzoate can be used to introduce a benzoyloxy group in the allyl position of unsaturated hydrocarbons.

From cyclohexene, 3-benzoyloxycyclohexene is formed with Tert-butyl peroxybenzoate in the presence of catalytic amounts of copper(I)bromide in 71 to 80% yield.

This allylic oxidation of alkenes, also known as Kharasch-Sosnovsky oxidation, generates racemic allylic benzoates in the presence of catalytic amounts of copper(I)bromide.

A modification of the reaction utilizes copper(II) trifluoromethanesulfonate as a catalyst and DBN or DBU as bases to achieve yields up to 80% in the reaction of acyclic olefins with Tert-butyl peroxybenzoate to allylic benzoates.

Substituted oxazolines and thiazolines can be oxidized to the corresponding oxazoles and thiazoles in a modified Kharash-Sosnovsky oxidation with Tert-butyl peroxybenzoate and a mixture of Cu(I) and Cu(II) salts in suitable yields.

The carboalkoxy group at the C-4 position is essential a successful reaction.

Benzene and furans can be alkenylated with olefins in an oxidative coupling under palladium salt catalysis, with Tert-butyl peroxybenzoate as hydrogen acceptor.

In the absence of Pd2+ salts, the aromatics are benzoxylated.

SYNONYMS:

tert-Butyl peroxybenzoate
614-45-9
tert-Butyl perbenzoate
tert-butyl benzenecarboperoxoate
t-Butyl perbenzoate
Chaloxyd tbpb
Perbutyl Z
Esperox 10
tert-Butyl peroxy benzoate
Terc.butylperbenzoan
Benzoyl tert-butyl peroxide
Peroxybenzoic acid, tert-butyl ester
Benzenecarboperoxoic acid, 1,1-dimethylethyl ester
t-Butyl peroxybenzoate
Perbenzoate de butyle tertiaire
tert-butyl benzoperoxoate
DTXSID9024699
NSC-674
54E39145KT
benzenecarboperoxoic acid tert-butyl ester
Trigonox C
DTXCID904699
tert-butylperoxybenzoate
t-Butyl peroxy benzoate
terc.Butylperbenzoan [Czech]
CAS-614-45-9
CCRIS 6217
HSDB 2891
NSC 674
Perbenzoic acid, tert-butyl ester
Tert butyl peroxybenzoate
EINECS 210-382-2
BRN 1342734
Perbenzoate de butyle tertiaire [French]
PEROXYBENZOIC ACID, T-BUTYL ESTER
AI3-06625
UNII-54E39145KT
t-butylperbenzoate
terc.Butylester kyseliny peroxybenzoove [Czech]
t-butyl per benzoate
t-butyl-peroxybenzoate
terc.Butylester kyseliny peroxybenzoove
tert-butyl-perbenzoate
tert.butyl perbenzoate
tert. butyl perbenzoate
t-butyl benzoyl peroxide
tertiary butyl perbenzoate
tert-butyl peroxy-benzoate
EC 210-382-2
SCHEMBL22820
WLN: 1X1&1&OOVR
NSC674
CHEMBL1328092
BUTYL PEROXYBENZOATE, TERT-
ZINC1596408
Tox21_202287
Tox21_300070
AKOS015890015
T-BUTYL BENZOYL PEROXIDE [INCI]
NCGC00091791-01
NCGC00091791-02
NCGC00091791-03
NCGC00091791-04
NCGC00254006-01
NCGC00259836-01
Benzenecarboperoxoic acid,1-dimethylethyl ester
EN300-129025
Luperox(R) P, tert-Butyl peroxybenzoate, 98%
PEROXYBENZOIC ACID, T-BUTYL ESTER [HSDB]
Q14469782
tert-Butyl peroxybenzoate, technical, >=95.0% (RT)


 

  • Share !
E-NEWSLETTER