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CAS Number: 75-91-2
Synonyms: TBHP, t-Butyl hydroperoxide, 1,1-Dimethylethyl hydroperoxide, 2-Hydroperoxy-2-methylpropane, BHP, Cadox TBH
tert-Butyl hydroperoxide (often abbreviated as TBHP) is an organic chemical compound classified as an alkyl hydroperoxide. Its structure consists of a tert-butyl group attached to a hydroperoxide group, giving it the formula (CH₃)₃COOH .
This compound is a powerful and versatile oxidizing agent, which is its primary role in industrial and laboratory chemistry. It is widely utilized to initiate various oxidation reactions, where it helps to introduce oxygen atoms into other organic molecules. These processes are fundamental in the production of a vast array of chemicals, including polymers, pharmaceuticals, and agrochemicals. It serves as a radical initiator in polymerization reactions, helping to build long-chain molecules from smaller monomers .
TBHP is a highly reactive and potentially dangerous substance. It is typically handled as a solution in a solvent like decane or water to mitigate its explosive hazards, as concentrated forms can be shock-sensitive and decompose violently. It is corrosive and a strong irritant to the skin, eyes, and mucous membranes. Due to its reactivity and oxidizing power, it requires careful storage and handling procedures to prevent fires or explosions. It must be kept away from sources of ignition, heat, and incompatible materials such as strong reducing agents, acids, and heavy metal compounds .
Specific Applications and Benefits:
Chemical Synthesis (Oxidizing Agent):
Epoxidation: Industrially, it is used to epoxidize alkenes, converting them into epoxides (three-membered ring ethers). These epoxides are key intermediates in the production of plastics, resins, and fine chemicals (e.g., the Halcon process for propylene oxide).
Alcohol Oxidation: It can oxidize primary and secondary alcohols to aldehydes and ketones, respectively, often under mild conditions.
Radical Initiator in Polymerization: Used to initiate the free-radical polymerization of monomers like styrene, acrylates, and methacrylates to produce plastics, adhesives, and coatings.
Organic Synthesis: A key reagent in numerous named reactions, including the Sharpless epoxidation (for producing chiral molecules in pharmaceuticals) and the oxidation of sulfides to sulfoxides.
Safety Handling: It is crucial to note that TBHP is a highly reactive and dangerous substance. It is typically handled in dilute solutions (e.g., 70% in water or decane) to mitigate the risk of explosive decomposition. It must be stored away from any ignition sources, reducing agents, and incompatible materials.
Laboratory Handling and Storage
Commercial Sources:
Most economical: 70% solution in water
For smaller laboratory scale: Anhydrous solutions in 2,2,4-trimethylpentane (isooctane)
Storage Recommendations:
Current solvent of choice: Isooctane
Alternative solvents: Dichloromethane or toluene
Solvents to avoid: Dichloroethane should not be used
Storage containers: High density polyethylene bottles preferred over glass due to chance of slight pressurization
Concentration: 5.5 M solutions in isooctane commercially available; 3 M solutions considered too dilute
Drying Instructions:
Storage over molecular sieves not recommended
Brief drying over sieves (approximately 30 minutes) of required amount just before use is acceptable practice
Dichloromethane solutions require storage at 0°C
Toluene solutions occasionally develop contaminants that inhibit catalytic reactions
SAFETY INFORMATION ABOUT TERT-BUTYL HYDROPEROXIDE
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
