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DESCRIPTION
Di-tert-butyl peroxide (DTBP) is an organic compound with the chemical formula C8H18O2.
Di-tert-butyl peroxide is a member of the peroxide class and is commonly used as a radical initiator in the polymerization of plastics and rubbers.
Cas Number: 110-05-4
SYNONYMS
Di-tert-butyl peroxide,110-05-4,tert-Butyl peroxide,Di-t-butyl peroxide,Cadox,Peroxide, bis(1,1-dimethylethyl),t-Butyl peroxide,tert-Butylperoxide,Trigonox B,2-(tert-Butylperoxy)-2-methylpropane,Cadox TBP,Bis(tert-butyl) peroxide,Kayabutyl D,Perbutyl D,Interox DTB,(Tributyl)peroxide,Di-tert-butylperoxid,Peroxyde de butyle tertiaire,Di-tert-butyl peroxyde,di-t butyl peroxide,NSC 673,Di-tert-Butyl hydroperoxide,di-tert,butylperoxide,Perossido di butile terziario,CCRIS 4613,HSDB 1326,Di-tertiary-butyl peroxide,2-tert-butylperoxy-2-methylpropane,EINECS 203-733-6,UNII-M7ZJ88F4R1,BIS(1,1-DIMETHYLETHYL)PEROXIDE,DTXSID2024955,Bis(1,1-dimethylethyl) peroxide,Peroxide, tert-butyl-,NSC-673,(tert-C4H9O)2,Peroxide, bis-tert-butyl-,DTXCID704955,M7ZJ88F4R1,EC 203-733-6,BIS(1,1-DIMETHYLETHYL)PEROXIDE [HSDB],t-butyl peroxide bis(1,1-di-methylethyl)peroxide,Bis(t-butyl)peroxide,2,2'-dioxybis(2-methylpropane),T-butyl-peroxide,CAS-110-05-4,Di-tert-butylperoxid [German],di(t-butyl) peroxide,Di-tert-butyl peroxyde [Dutch],DI-TERT,BUTYL PEROXIDE, (TECHNICALLY PURE),DI-TERT-BUTYL PEROXIDE, [TECHNICALLY PURE],Peroxyde de butyle tertiaire [French],Dibutyl peroxide (tertiary),Perossido di butile terziario [Italian],t-butylperoxide,tbutyl peroxide,Ditbutyl peroxide,Ditertbutylperoxid,TBHP compound,tBuOOtBu,tertbutyl peroxide,Di-t,butylperoxide,di-tertbutylperoxide,ditert.butylperoxide,Bis(tbutyl)peroxide,Ditertbutyl,peroxyde,2-tert-butylperoxy-2-methyl-propane,MFCD00008803,di-tertbutyl peroxide,ditert-butyl peroxide,PEROXIMON DB,di-tert.butyl peroxide,di-tertiarybutylperoxide,ditertiary butylperoxide,ditertiarybutyl peroxide,Bis(tertbutyl) peroxide,di(tert.-butyl)peroxide,di(tert.butyl) peroxide,di-tert.-butyl peroxide,di-tertiary butylperoxide,DitertButyl hydroperoxide,ditertiary butyl peroxide,di-tertiary butyl peroxide,DTBP [MI],SCHEMBL14861,B 50ELQ,Bis(1,1dimethylethyl)peroxide,NSC673,CHEMBL1558599,Peroxide, bis(1,1dimethylethyl),(CH3)3CO-OC(CH3)3,2-tert-butyldioxy-2-methylpropane,Tox21_201461,Tox21_300099
UN3107,AKOS015902599,2-(tert-Butylperoxy)-2-methylpropane #,NCGC00091801-01,NCGC00091801-02,NCGC00091801-03,NCGC00254065-01,NCGC00259012-01,tert-Butyl peroxide (Luperox DI), 97%,Luperox(R) DI, tert-Butyl peroxide, 98%,D3411,NS00006093,A802134,Q413043,J-002365,J-520402,WLN: 1X1 & 1 & OOX1 & 1 & 1,F0001-0215
Di-tert-butyl peroxide (DTBP) is a highly reactive organic compound that plays a crucial role in the field of chemistry and industry.
It is part of the larger class of peroxides, molecules that contain an oxygen-oxygen single bond (O-O) and are known for their instability and ability to release oxygen upon decomposition.
Peroxides like DTBP are often used as initiators in polymerization reactions, where they break bonds in other molecules, leading to the formation of long polymer chains.
Due to its significant role in the polymer and chemical industries, DTBP has garnered attention as both a valuable reagent and a compound requiring careful handling due to its potential hazards.
DTBP is typically used as a radical initiator in organic synthesis and industrial polymerization, notably in the production of various plastics, resins, and rubbers.
Its high reactivity makes it especially useful in reactions that require the generation of free radicals, which are critical intermediates in many chemical processes.
Beyond polymerization, DTBP has also found applications in the synthesis of pharmaceuticals and other fine chemicals. However, its unstable nature, especially when subjected to heat, light, or contamination, demands careful storage, handling, and regulatory compliance.
This article aims to explore DTBP in great detail, covering its chemical structure, synthesis, applications, safety precautions, and the broader impact of its use in various industries.
Additionally, an exploration of the toxicological and environmental concerns associated with its use, as well as the development of alternatives, will be presented.
Chemical Structure and Properties
Chemical Structure
Di-tert-butyl peroxide has the chemical formula (CH₃)₃COOOC(CH₃)₃, consisting of two tert-butyl groups (C₄H₉) attached to an oxygen-oxygen bond.
The structure is characterized by the oxygen-oxygen single bond, which is a key feature of all peroxides.
The tert-butyl groups, each consisting of a central carbon atom bonded to three methyl groups, provide steric hindrance and contribute to the molecule's instability.
The large size of the tert-butyl groups makes the O-O bond weaker and more prone to homolytic cleavage, facilitating the formation of radicals upon decomposition.
PHYSICAL PROPERTIES
Molecular Weight: 146.22 g/mol.
Boiling Point: 96-98°C.
Melting Point: -25°C.
Density: Approximately 0.82 g/cm³ at 25°C.
Solubility: Soluble in most organic solvents such as acetone, ethanol, and ether but insoluble in water.
Appearance: Di-tert-butyl peroxide is a colorless or slightly yellow liquid with a characteristic odor.
The molecular size and the presence of bulky tert-butyl groups also contribute to the relatively low volatility of DTBP, although it is still volatile enough to pose significant risks in industrial settings.
CHEMICAL PROPERTIES
DTBP is highly reactive due to the oxygen-oxygen bond, which is weak and easily cleaved by heat, light, or other radical species.
Upon decomposition, DTBP produces two tert-butoxy radicals (C₄H₉O•), which can initiate polymerization or participate in other free-radical reactions.
The decomposition of DTBP follows a first-order rate law under most conditions, meaning the rate of decomposition depends directly on the concentration of DTBP.
Decomposition is typically accelerated by higher temperatures and UV light, which is why DTBP is often stored in cool, dark environments.
DTBP's reactivity and its potential to generate radicals make it an essential tool in organic chemistry, particularly for reactions that require the generation of free radicals to break bonds or initiate polymerization.
Synthesis and Preparation (3-4 pages)
Industrial Synthesis
Di-tert-butyl peroxide is primarily produced through the reaction of tert-butyl hydroperoxide (TBHP) with an appropriate catalyst or initiator.
The industrial synthesis method involves the reaction of isobutene or its derivatives with oxygen in the presence of a catalyst, typically a peroxide compound or a metal catalyst such as titanium or iron.
The reaction conditions, such as temperature, pressure, and the choice of catalyst, are carefully controlled to maximize the yield of DTBP while minimizing the formation of side products.
One of the most common methods involves the oxidation of isobutene to form tert-butyl hydroperoxide, which is then treated with an initiator, typically sodium or another radical-producing substance, to form di-tert-butyl peroxide.
The process requires a high level of control due to the volatile nature of the intermediates and the tendency of the peroxide to decompose rapidly under improper conditions.
Laboratory Synthesis
Laboratory-scale synthesis of DTBP generally involves the reaction of tert-butyl alcohol with hydrogen peroxide, a method that allows for the controlled formation of the peroxide.
This reaction is typically carried out in the presence of a catalytic amount of sulfuric acid to facilitate the generation of hydrogen peroxide in situ.
The reaction is exothermic, requiring careful temperature control to avoid decomposition.
An alternative laboratory method for synthesizing DTBP involves the use of peracetic acid as a reagent to oxidize isobutene.
This method can offer higher yields, especially in cases where specific purity is required.
Purification and Isolation
Once DTBP is synthesized, it must be purified to remove impurities, including residual reactants or side products.
Common purification methods include distillation, where the compound is separated based on its boiling point, and recrystallization, which exploits the solubility differences of DTBP and its impurities.
Due to its instability, purification is often carried out under inert conditions, such as nitrogen or argon atmospheres, to prevent premature decomposition.
Reaction Mechanisms
Radical Initiation in Polymerization
Di-tert-butyl peroxide is widely used as a radical initiator in the polymerization of monomers such as styrene, acrylates, and other vinyl compounds.
In the polymerization process, DTBP decomposes to form two tert-butoxy radicals (C₄H₉O•).
These radicals can initiate the polymerization process by attacking the double bond of a monomer, forming a new radical at the polymer chain's growing end.
This leads to the propagation of the polymer chain, where each new monomer unit is added by the successive attack of the growing radical on the monomer.
The decomposition of DTBP is a temperature-dependent process.
At higher temperatures, the rate of decomposition increases, and the formation of radicals becomes more frequent.
This is why DTBP is typically used in high-temperature polymerization processes, such as in the production of synthetic rubber and certain types of plastic resins.
Decomposition Pathways
The decomposition of DTBP follows a first-order kinetic process under typical conditions.
The O-O bond in DTBP is relatively weak, and upon activation (e.g., by heat or UV light), the molecule undergoes homolytic cleavage, producing two tert-butoxy radicals.
These radicals are highly reactive and can engage in various reactions, including initiating polymerization, undergoing further decomposition, or reacting with other molecules in the environment.
In the case of polymerization, the tert-butoxy radicals react with monomers, but if there are no suitable substrates, they can recombine, forming stable by-products such as isobutane or other oligomers.
SAFETY INFORMATION ABOUT DI-TERT-BUTYL PEROXIDE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
