TERT-BUTYL PEROXYBENZOATE
TERT-BUTYL PEROXYBENZOATE
tert-Butyl peroxybenzoate = TBPB
Chemical Name: tert-Butyl peroxybenzoate
CAS Number: 614-45-9
Molecular Fomula: C11H14O3
Molecular Weight: 194.23
tert-Butyl peroxybenzoate (TBPB) a chemical compound from the group of peresters (compounds containing the general structure R1-C(O)OO-R2) which contains a phenyl group as R1 and a tert-butyl group as R2.
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.
Properties of tert-Butyl peroxybenzoate:
TBPB is a clear light yellow liquid, which is little soluble in water but well in many organic solvents such as ethanol or phthalate.
As peroxo compound, TBPB 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.
TBPB 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 TBPB, 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 TBPB even in low concentrations.
However, TBPB 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.
Applications of tert-Butyl peroxybenzoate:
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).
TBPB can be used to introduce a benzoyloxy group in the allyl position of unsaturated hydrocarbons.
From cyclohexene, 3-benzoyloxycyclohexene is formed with TBPB 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.
Applications 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 TBPB to the sodium salt of trimethylsilylethanesulfonic acid and the subsequent reaction with thionyl chloride to the corresponding sulfonyl chloride.
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 TBPB to allylic benzoates.
Substituted oxazolines and thiazolines can be oxidized to the corresponding oxazoles and thiazoles in a modified Kharash-Sosnovsky oxidation with TBPB and a mixture of Cu(I) and Cu(II) salts in suitable yields
Use and applications of tert-Butyl peroxybenzoate:
Tert-Butyl peroxybenzoate is primarily used as a radical initiator to induce polymerisation (free radical polymerisation process), for the manufacture of e.g. PVC, and as a curing agent for the production of unsaturated polyester resins.
Physical / Chemical properties of tert-Butyl peroxybenzoate:
Organic peroxides are thermally unstable substances or mixtures, which can undergo exothermic self-accelerating decomposition.
Production of tert-Butyl peroxybenzoate:
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.
tert-Butyl peroxybenzoate Usages:
Uses This product can be used for curing curing of unsaturated polyester resin curing agent, and high pressure polyethylene, polystyrene, diallyl phthalate (DAP) and other resin polymerization catalyst.
General description of tert-Butyl peroxybenzoate:
tert-butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane has been reported.
Tert-butyl peroxybenzoate (TBPB) is thermally unstable organic peroxide, which may cause disasters such as fire or explosion when excessive heat released due to thermal decomposition.
Ionic liquid is often used as a catalyst and inhibitor in engineering applications recently.
This study investigated the thermal decomposition characteristics of TBPB when added two different ionic liquids which are 1-Propyl-3-methylimidazolium iodide ([PMIM][I]) and 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4]) respectively with different mass ratio under DSC tests.
Characteristic parameters such as the onset exothermic temperature (T0) and heat of decomposition (ΔHd) of samples were compared.
Kinetic parameters such as activation energy Ea were computed using two isoconversional methods which were Ozawa method and Friedman method respectively.
The model based (zeroth order reaction) estimation method was used to estimate TMRad at T0 from non-isothermal DSC measurements to assess the thermal hazard of five samples.
The paper aims to study the effect of ionic liquids (ILs) on the thermal decomposition of TBPB and analysis the influence of two ionic liquids on the decomposition mechanism of TBPB.
Key Benefits of tert-Butyl peroxybenzoate for Industry Participants & Stakeholders:
-Industry drivers, restraints, and opportunities covered in the study
-Neutral perspective on the market performance
-Recent industry trends and developments
-Competitive landscape & strategies of key players
-Potential & niche segments and regions exhibiting promising growth covered
-Historical, current, and projected market size, in terms of value
-In-depth analysis of the Tert-Butyl Peroxybenzoate Market
Name: tert-butyl peroxybenzoate
Brand names: Luperox® P grades, Luperox® DP10G, Luperox® DP20
Chemical name (IUPAC): tert-butyl benzenecarboperoxoate
CAS number: 614-45-9
EC number: 210-382-2
Molecular formula: C11H14O3
Applications of tert-Butyl peroxybenzoate:
tert-Butyl peroxybenzoate was also was employed as initiator during:
-grafting of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-4-oxyacetamido-(3 propyltriethoxysilane) to poly(ethylene co-octene)
-preparation of conformal poly(cyclohexyl methacrylate) thin films via initiated chemical vapor deposition
Applications of tert-Butyl peroxybenzoate:
tert-Butyl peroxybenzoate was employed as polymerization and cross-linking catalyst.
tert-Butyl peroxybenzoate was also was employed as initiator during grafting of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-4-oxyacetamido-(3 propyltriethoxysilane) to poly(ethylene co-octene and in preparation of conformal poly(cyclohexyl methacrylate) thin films via initiated chemical vapor deposition.
Solubility of tert-Butyl peroxybenzoate:
tert-Butyl peroxybenzoate is soluble in ether, alcohol, ester, and ketones.
tert-Butyl peroxybenzoate is insoluble in water.
A new protocol for the synthesis of amides from tert-butyl peroxybenzoate (TBPB) and ammonia/amines has been developed under catalyst- and solvent-free conditions.
The ammonia, primary and secondary amines reacted smoothly with TBPB to furnish the corresponding primary, secondary, and tertiary amides in excellent yields.
TBPB proved to be an efficient and highly chemoselective benzoylating reagent for aliphatic amines in the presence of aromatic amines/ hydroxyl groups.
Trade name : TBPB
REACH Registration Number : 01-2119513317-46-0003
Substance name : tert-Butyl perbenzoate
EC-No. : 210-382-2
Chemical Properties of tert-Butyl peroxybenzoate: colourless or slightly yellow liquid
Uses of tert-Butyl peroxybenzoate: Polymerization initiator for polyethylene, polystyrene, polyacrylates, and polyesters; chem- ical intermediate.
t-Butyl peroxybenzoate is used for elevatedtemperaturecuring of polyesters and to initiatepolymerization reactions.
tert-Butyl peroxybenzoate was employed as polymerization and cross-linking catalyst.
General Description of tert-Butyl peroxybenzoate: Clear, colorless to slightly yellow liquid with a mild, aromatic odor.
tert-Butyl peroxybenzoate also is stored and transported as a mixture with inert solids and as a solvent slurry, to mitigate the explosion hazard.
Air & Water Reactions of tert-Butyl peroxybenzoate: Insoluble in water.
Chemical Name: tert-Butyl Perbenzoate
Synonyms: Benzoyl tert-butyl peroxide; CP 02; CP 02 (catalyst); Chaloxyd TBPB; Chaloxyd; TBPB-HA-M 1; Esperox 10; Interox TBPB-HA-M 1; Kayabutyl B; LQ-TBPB; Link-Cup; TBPB; Luperox P; Luperox PXL; NSC 674; Norox TBPB; Perbutyl Z; TBPB; TBPB-HA-M 1; TBPB-HA-M 3; TC 5; TC 5 (vulcanizer); Trigonox 93; Trigonox C; Trigonox C 50D; V 73; t-Butyl peroxybenzoate; tert-Butyl benzoyl peroxide; tert-Butyl peroxybenzoate
CAS Number: 614-45-9
Molecular Formula: C₁₁H₁₄O₃
Molecular Weight: 194.23
Category: Building Blocks; Catalyst; Cross-linkers;
Applications of tert-Butyl peroxybenzoate: tert-Butyl Perbenzoate is used as a catalyst in the preparation of paper strengthening agents for papermaking.
Quality Level: 200
vapor density: 6.7 (vs air)
vapor pressure: 3.36 mmHg ( 50 °C)
assay: 98%
form: liquid
refractive index: n20/D 1.499 (lit.)
bp: 75-76 °C/0.2 mmHg (lit.)
solubility: water: soluble 1.18 g/L
density: 1.021 g/mL at 25 °C (lit.)
SMILES string: CC(C)(C)OOC(=O)c1ccccc1
InChI: 1S/C11H14O3/c1-11(2,3)14-13-10(12)9-7-5-4-6-8-9/h4-8H,1-3H3
Inchi Key: GJBRNHKUVLOCEB-UHFFFAOYSA-N
A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism.
Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation.
Moreover, this method could also be efficiently extended to the alkylation of quinones.
This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone.
Notably, antimalarial parvaquone was synthesized by the reaction.
Physical state: Liquid at 20°C and 1013 hPa
Colour: Slightly yellow
Odour: Slightly aromatic
Molecular weight: 194.2 g/mol
Density: 1.04 g/cm3 at 20°C
Vapour pressure: 0.003 Pa at 20°C
Melting range: 9-11°C at 1013hPa
Self-Accelerating Decomposition Temperature (SADT): 60°C
Explosive properties: Risk of explosion if heated under confinement.
Water solubility: 325 mg/L at 20°C
Octanol-water partition coefficient (Log Kow): 3 at 25°C
Product description: tert-Butyl peroxybenzoate
Active Oxygen content : 8.0%
CAS No. : 614-45-9
Specification
Appearance : clear liquid
Assay : 98.0% min.
Color : 100 Pt-Co max.
tert-Butyl hydroperoxide : 1000 mg/kg max.
Inorganic + organic hydrolyzable chloride : 50 mg/kg max.
Physical properties
Density, 20℃ : 1040 kg/m3
Viscosity, 20℃ : 6 mPa.s
Freezing point : approx. 8℃
Packaging of tert-Butyl peroxybenzoate:
Standard packaging size for LQ-TBPB is 25 kg net.
Smaller packaging size is available on request.
Applications of tert-Butyl peroxybenzoate:
1.Polymerization of styrene:
TBPB can be used for the polymerization and copolymerization of styrene in the temperature range of 100-140℃.
During polymerization the temperature is increased in steps.
2.Polymerization of acrylates and methacrylates:
TBPB can be used as initiator for the solution (co)polymerization of acrylates and methcrylates in the temperatures range of 100-170℃, amongst others for the coatings.
TBPB can also be applied as an initiator for the bulk and suspension (co)polymerization of acrylates and methcrylates.
3. Polymerization of ethylene:
TBPB is an efficient initirtor for the ethylene polymerization under high pressure in both autoclave and tubular processes.
To obtain a wide spectrum of polymerization temperatures, combinations with other peroxides are applied in practice.
Depending on reaction conditions.
TBPB is active in the temperature range of 220-270℃.
4. Other applications of tert-Butyl peroxybenzoate:
TBPB can also be used for the (co)polymerization of acrylonitrile and vinyl acetate.
5. Crosslinking Peroxides:
TBPB,is suitable for crosslinking of EPDM rubber compounds at ambient temperature within some weeks.
Rubber compounds containing LQ-TBPB have moderate processing safety in combination with a very high speed of cure.
6. Peroxides for Thermoset Resins:
TBPB, tert-butyl peroxybenzoate, is an aromatic perester, which is used for the curing of unsaturated polyester resins at elevated temperatures.
TBPB is preferred for the curing of UP resin based Hot Press Moulding formulations (SMC, BMC, ZMC etc) in the temperature range of 120 – 170℃.
A tert-butyl peroxybenzoate (TBPB)-promoted direct α-methylation of 1,3-dicarbonyl compounds has been developed, providing α-methyl derivatives in moderate to good yields.
In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator.
This work represents a key complement to the traditional α-methylation of 1,3-dicarbonyl compounds using methyl iodide.
Density: 1.1±0.1 g/cm3
Boiling Point: 282.4±9.0 °C at 760 mmHg
Melting Point: 8 °C
Molecular Formula: C11H14O3
Molecular Weight: 194.227
Flash Point: 109.7±12.8 °C
Exact Mass: 194.094299
PSA: 35.53000
LogP: 3.33
Vapour density: 6.7 (vs air)
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Index of Refraction: 1.497
Stability: Stable. Combustible. Incompatible with a wide range of organic materials – oxidizer.
May react violently with organic compounds.
Water Solubility: Immiscible
tert-Butyl peroxybenzoate
614-45-9
tert-Butyl perbenzoate
t-Butyl perbenzoate
Chaloxyd tbpb
tert-butyl benzenecarboperoxoate
Perbutyl Z
Esperox 10
Benzenecarboperoxoic acid, 1,1-dimethylethyl ester
tert-Butyl peroxy benzoate
Terc.butylperbenzoan
Benzoyl tert-butyl peroxide
Peroxybenzoic acid, tert-butyl ester
Perbenzoate de butyle tertiaire
t-Butyl peroxybenzoate
UNII-54E39145KT
54E39145KT
benzenecarboperoxoic acid tert-butyl ester
DSSTox_CID_4699
Trigonox C
DSSTox_RID_77504
DSSTox_GSID_24699
tert-butylperoxybenzoate
t-Butyl peroxy benzoate
terc.Butylperbenzoan [Czech]
CAS-614-45-9
CCRIS 6217
HSDB 2891
NSC 674
Perbenzoic acid, tert-butyl ester
EINECS 210-382-2
BRN 1342734
Perbenzoate de butyle tertiaire [French]
PEROXYBENZOIC ACID, T-BUTYL ESTER
AI3-06625
t-butylperbenzoate
terc.Butylester kyseliny peroxybenzoove [Czech]
tert-butoxy benzoate
t-butyl per benzoate
ACMC-20ajkp
t-butyl-peroxybenzoate
terc.Butylester kyseliny peroxybenzoove
tert-butyl-perbenzoate
tert.butyl perbenzoate
tert. butyl perbenzoate
tert-butyl benzoperoxoate
tertiary butyl perbenzoate
tert-butyl peroxy-benzoate
EC 210-382-2
SCHEMBL22820
WLN: 1X1&1&OOVR
NSC674
CHEMBL1328092
DTXSID9024699
NSC-674
ZINC1596408
Tox21_202287
Tox21_300070
SBB064105
AKOS015890015
NCGC00091791-01
NCGC00091791-02
NCGC00091791-03
NCGC00091791-04
NCGC00254006-01
NCGC00259836-01
Benzenecarboperoxoic acid,1-dimethylethyl ester
Luperox(R) P, tert-Butyl peroxybenzoate, 98%
Q14469782
tert-Butyl peroxybenzoate, technical, >=95.0% (RT)
benzenecarboperoxoic acid 1,1-dimethylethyl ester
benzenecarboperoxoic acid, 1,1-dimethylethyl ester
benzoyl t-butyl peroxide
benzoyl tert-butyl peroxide
tert-butoxy benzoate
tert-butyl benzenecarboperoxoate
tert-butyl perbenzoate
tert-butyl peroxybenzoate
tert-butylperoxybenzoate
esperox 10
luperox P
2-methyl-2-propanyl benzenecarboperoxoate
perbenzoic acid t-butyl ester
perbenzoic acid, tert-butyl ester
perbutyl Z
peroxybenzoic acid t-butyl ester
peroxybenzoic acid, t-butyl ester
peroxybenzoic acid, tert-butyl ester
trigonox C
210-382-2 [EINECS]
2-Methyl-2-propanyl benzenecarboperoxoate [ACD/IUPAC Name]
2-Methyl-2-propanyl-benzolcarboperoxoat [German] [ACD/IUPAC Name]
54E39145KT
614-45-9 [RN]
Benzènecarboperoxoate de 2-méthyl-2-propanyle [French] [ACD/IUPAC Name]
Benzenecarboperoxoic acid, 1,1-dimethylethyl ester [ACD/Index Name]
Benzoyl tert-butyl peroxide
Luperox(R) P, tert-Butyl peroxybenzoate
MFCD00008802 [MDL number]
SD9450000
terc.Butylester kyseliny peroxybenzoove [Czech]
tert-Butyl benzenecarboperoxoate
tert-Butyl perbenzoate
tert-Butyl peroxybenzoate [Wiki]
UNII:54E39145KT
2-hydroperoxybenzoic acid tert-butyl ester
4-09-00-00715 [Beilstein]
4-09-00-00715 (Beilstein Handbook Reference) [Beilstein]
Benzenecarboperoxoic acid 1,1-dimethylethyl ester
benzenecarboperoxoic acid tert-butyl ester
BENZOYL T-BUTYL PEROXIDE
Benzoyl tert.-butyl peroxide
Chaloxyd tbpb
EINECS 210-382-2
Esperox 10
Luperox P
NCGC00091791-02
Novox
Perbenzoate de butyle tertiaire
Perbenzoate de butyle tertiaire [French]
perbenzoic acid t-butyl ester
Perbenzoic acid, tert-butyl ester
Perbutyl Z
peroxybenzoic acid t-butyl ester
Peroxybenzoic acid, t-butyl ester
Peroxybenzoic acid, tert-butyl ester
t-Butyl perbenzoate
t-Butyl peroxy benzoate
t-Butyl Peroxybenzoate
terc.Butylester kyseliny peroxybenzoove [Czech]
Terc.butylperbenzoan
terc.Butylperbenzoan [Czech]
Tert butyl peroxybenzoate
tert-butoxy benzoate
tert-Butyl peroxy benzoate
tert-Butyl Peroxybenzoate (en)
tert-butylperoxybenzoate
Trigonox C
UNII-54E39145KT
WLN: 1X1&1&OOVR
TBPB
novox
perbutylz
esperox10
trigonoxc
Luperox P
VAROX TBPB
chaloxydtbpb
VAROX TBPB-50
TRIGONOX(R) C