Tert-Butyl hydroperoxide

Tert-Butyl hydroperoxide (TBHP) is a chemical compound with the formula (CH₃)₃COOH. It is a clear liquid, soluble in most organic solvents but poorly soluble in water. TBHP is commonly used as a free radical initiator in polymerization processes and as an oxidizing agent in organic synthesis. Due to its reactive nature, TBHP is also involved in various chemical reactions that are significant in both industrial and laboratory settings.

Properties

TBHP is a peroxide, a group of compounds known for their -O-O- bond. This bond is relatively weak, making peroxides like TBHP highly reactive, especially towards reduction and oxidation reactions. TBHP has a boiling point of 34°C at 14 mmHg and a flash point of 37°C, indicating its high volatility and flammability. It is typically handled with care in laboratory and industrial environments due to its explosive potential when mixed with combustible materials.

Applications

Polymerization

In the field of polymer chemistry, TBHP serves as an initiator for the polymerization of certain monomers, facilitating the formation of polymer chains. It generates free radicals under appropriate conditions, which then propagate the polymerization process.

Organic Synthesis

TBHP is widely used in organic synthesis as an oxidizing agent. It is involved in the oxidation of alcohols to ketones or aldehydes, and in the epoxidation of alkenes. Its effectiveness as an oxidant makes it a valuable reagent in the preparation of various organic compounds.

Environmental and Safety Considerations

Handling TBHP requires strict safety measures due to its reactive nature. It is classified as a hazardous material, and direct contact can cause severe skin burns and eye damage. TBHP is also a potent oxidizer, which can cause or exacerbate fires if improperly stored or handled.

Health Hazards

Exposure to TBHP can lead to several health issues, including respiratory irritation, skin and eye damage, and if ingested, it can cause organ damage. Safety protocols, including the use of personal protective equipment (PPE), are essential when working with TBHP to minimize exposure risks.

Regulation and Handling

TBHP is subject to regulation under various chemical safety guidelines, including those set forth by the Occupational Safety and Health Administration (OSHA) and the Environmental Protection Agency (EPA) in the United States. Proper storage, handling, and disposal procedures are crucial to prevent accidents and environmental contamination.

See Also

• Peroxide
• Free radical polymerization
• Oxidizing agent
• Safety data sheet