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CAS Number: 80-15-9
EC Number: 201-254-7
Molecular Formula: C₉H₁₂O₂
Molecular Weight: 152.19 g/mol
Synonyms:
Cumyl hydroperoxide; α,α-Dimethylbenzyl hydroperoxide; 1-Methyl-1-phenylethyl hydroperoxide; Isopropylbenzene hydroperoxide; CHP; Cumene hydroperoxide (technical grade); Peroxan CU; Trigonox K-80
Note: Cumene hydroperoxide and cumyl hydroperoxide refer to the same chemical substance. The name "cumene hydroperoxide" is derived from its parent hydrocarbon cumene (isopropylbenzene), while "cumyl hydroperoxide" refers to the cumyl (α,α-dimethylbenzyl) functional group. Both names are used interchangeably in industrial and technical literature.
Chemical Identity and Properties:
Cumene hydroperoxide is an organic peroxide produced by the air oxidation of cumene. It is a key intermediate in the cumene-to-phenol process and serves as a radical initiator in polymerization reactions. The compound is characterized by the presence of a hydroperoxide group (-OOH) attached to the cumyl moiety.
Physical Properties:
Appearance: Colorless to pale yellow liquid
Odor: Sharp, pungent, characteristic
Melting Point: -30 °C
Boiling Point: Decomposes before boiling at atmospheric pressure; 100–101 °C at 8 mmHg
Density: 1.03–1.06 g/cm³ at 20 °C
Flash Point: 57–79 °C (closed cup)
Autoignition Temperature: 300 °F (149 °C)
Vapor Pressure: 0.04–0.6 mmHg at 20–25 °C
Vapor Density: 5.4 (air = 1)
Solubility: Slightly soluble in water; soluble in organic solvents including alcohols, ethers, ketones, esters, and hydrocarbons
Decomposition Temperature: 153 °C (atmospheric pressure)
Manufacturing Process:
Cumene hydroperoxide is produced by the liquid-phase autoxidation of cumene. The reaction proceeds via a free-radical chain mechanism:
Initiation: Formation of cumyl radicals from cumene
Propagation: Reaction of cumyl radicals with oxygen to form cumylperoxy radicals, which abstract hydrogen from additional cumene molecules to form cumene hydroperoxide and regenerate cumyl radicals
Termination: Various termination reactions between radicals
The reaction is typically carried out at 100–130 °C and atmospheric pressure in stainless steel reactors. Conversion is maintained at 20–30% to minimize side reactions and ensure selectivity. The product is then concentrated by distillation to remove unconverted cumene.
Applications:
1. Phenol and Acetone Production:
Cumene hydroperoxide is the critical intermediate in the cumene process, which accounts for over 95% of global phenol production. The process involves:
Oxidation of cumene to cumene hydroperoxide (this compound)
Acid-catalyzed cleavage of cumene hydroperoxide to phenol and acetone
This co-production process yields approximately 0.6 tons of acetone per ton of phenol produced.
SAFETY INFORMATION ABOUT CUMENE 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
