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CAS Number: 80-15-9
EC Number: 201-254-7
Molecular Formula: C₉H₁₂O₂
Molecular Weight: 152.19 g/mol
Synonyms:
Cumene hydroperoxide; α,α-Dimethylbenzyl hydroperoxide; 1-Methyl-1-phenylethyl hydroperoxide; Isopropylbenzene hydroperoxide; CHP; α-Cumyl hydroperoxide; Cumylol hydroperoxide; Trigonox K-80; LUPEROX CU90; Peroxan CU-90L
Chemical Identity and Properties:
Cumyl hydroperoxide is an organic peroxide with the chemical structure consisting of a cumyl group (α,α-dimethylbenzyl) attached to a hydroperoxide (-OOH) functional group. In its pure form, it appears as a colorless to pale yellow liquid with a sharp, characteristic odor. Commercially, it is typically supplied as a solution in cumene or other solvents at concentrations ranging from 70% to 90% to enhance stability during storage and handling.
Physical Properties:
Appearance: Colorless to pale yellow liquid
Odor: Sharp, irritating, characteristic
Melting Point: -30 °C to less than -40 °F
Boiling Point: 100-101 °C at 8 mmHg (decomposes at 153 °C at atmospheric pressure)
Density: 1.03–1.06 g/cm³ at 20 °C
Flash Point: 57–79 °C (closed cup)
Vapor Pressure: 0.04–0.6 mmHg at 20–25 °C
Vapor Density: 5.4 (air = 1)
Solubility: Slightly soluble in water (approximately 1.5 g/100 mL); freely soluble in acetone, alcohol, ether, esters, hydrocarbons, and chlorinated solvents
Refractive Index: 1.521 at 20 °C
Chemical Reactivity and Stability:
Cumyl hydroperoxide is thermally unstable and undergoes exothermic decomposition when heated. The decomposition is accelerated by the presence of acids, bases, metal ions (particularly copper, iron, and lead), and reducing agents. Key stability parameters include:
10-hour half-life: 140 °C
1-hour half-life: 166 °C
1-minute half-life: 222 °C
Self-Accelerating Decomposition Temperature (SADT): 65–70 °C
Decomposition products include methane, acetophenone, cumyl alcohol, and various free radicals.
Manufacturing Process:
Cumyl hydroperoxide is produced industrially by the autoxidation of cumene (isopropylbenzene) with molecular oxygen. The reaction is carried out at elevated temperatures (100–130 °C) in the presence of an initiator or catalyst. This process is the first critical step in the cumene process for manufacturing phenol and acetone, where cumyl hydroperoxide is subsequently cleaved by acid catalysis.
Applications:
1. Polymerization Initiator:
Cumyl hydroperoxide is widely used as a free-radical initiator in polymerization reactions. It is particularly effective in redox-initiated emulsion polymerization systems at low temperatures (5–20 °C) when combined with reducing agents such as iron salts, sulfites, dithionites, or ascorbic acid. Major applications include:
Production of styrene-butadiene rubber (SBR)
Manufacturing of acrylonitrile-butadiene-styrene (ABS) resins
Emulsion polymerization of methacrylates and acrylic dispersions
2. Chemical Intermediate:
Serves as the key intermediate in the cumene process for phenol and acetone production, accounting for the majority of global phenol and acetone supply.
3. Oxidizing Agent:
Used as an epoxidation reagent for allylic alcohols and fatty acid esters, and in the Sharpless-type asymmetric oxidation of sulfides to sulfoxides.
4. Curing and Crosslinking:
Functions as a curing agent for unsaturated polyester resins and as a crosslinking agent for various polymer systems.
Safety and Hazard Profile:
Cumyl hydroperoxide is classified as a hazardous material with severe risks. The NFPA 704 diamond ratings are:
Health: 1 (can cause significant irritation)
Flammability: 2 (must be moderately heated to ignite)
Instability: 4 (readily capable of detonation or explosive decomposition at normal temperatures and pressures)
Special: OX (oxidizer)
GHS Hazard Classifications:
Organic peroxide Type F (Org. Perox. F)
Flammable liquid (H226)
Heating may cause a fire (H242)
Harmful if swallowed (H302)
Harmful in contact with skin (H312)
Toxic if inhaled (H331)
Causes severe skin burns and eye damage (H314)
May be fatal if swallowed and enters airways (H304)
Suspected of causing cancer (H350)
May cause damage to organs through prolonged or repeated exposure (H373)
Toxic to aquatic life with long-lasting effects (H411)
Reactivity Hazards:
Strong oxidizing agent that may react explosively with reducing agents
Violent reaction with copper, copper alloys, lead alloys, and mineral acids
Decomposes explosively with sodium iodide
May ignite organic materials upon contact
Storage and Handling:
Storage Conditions:
Maximum storage temperature: 30 °C
Minimum storage temperature: 0 °C (to prevent crystallization)
Shelf life: 6 months under recommended conditions
Store in original containers in a cool, dry, well-ventilated area away from direct sunlight
Keep away from heat sources, sparks, open flames, and incompatible materials
Incompatibilities:
Avoid contact with reducing agents, strong acids, strong bases, heavy metal salts (copper, iron, lead, cobalt), powdered metals, rust, charcoal, amines, and combustible materials.
Packaging:
Typically supplied in 25 kg HDPE containers and 200 kg HDPE drums.
Emergency Response:
Small spills: 50 meters (150 feet) isolation distance
Large spills: 250 meters (800 feet) isolation distance
Firefighting: Use foam, dry chemical, or carbon dioxide; water spray may be used for cooling containers but may be ineffective for extinguishing the fire itself
Personal protective equipment: Self-contained breathing apparatus, chemical-resistant gloves (nitrile or neoprene), chemical splash goggles, and full protective clothing
SAFETY INFORMATION ABOUT CUMYL 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
