Perodox® A - Tert-Butyl hydroperoxide

The chemical formula for tert-Butyl Hydroperoxide is C₄H₁₀O₂​

The CAS Registry Number for tert-Butyl Hydroperoxide is 75-91-2

The molecular weight of tert-Butyl Hydroperoxide is 90.121 g/mol

Common synonyms include TBHP, 1,1-Dimethylethyl hydroperoxide, 2-Hydroperoxy-2-methylpropane,Perodox A

The structural formula is (CH₃)₃COOH, featuring a hydroperoxy group (-OOH) attached to a tertiary butyl group

Pure TBHP is typically a colorless to pale yellow transparent liquid

The boiling point is approximately 37°C at 15 mmHg​ (or 96°C with decomposition at atmospheric pressure)

The melting point of TBHP is -3°C

The density is approximately 0.937 g/mL​ at 20°C

Yes, TBHP is miscible with water and also soluble in most organic solvents like ethanol, ether, and decane

The flash point is reported as 35-43°C, classifying it as a flammable liquid

The vapor pressure is 7.38 mmHg at 25°C

The refractive index (n20/D) is approximately 1.399

TBHP is stable under recommended storage conditions (cool, 2-8°C) but decomposes upon heating, exposure to light, or contamination by metals, reducing agents, or acids, which can lead to violent decomposition

It is primarily produced by the reaction of tert-butanol with hydrogen peroxide in the presence of sulfuric acid

Key pyrolysis products include acetone, tert-butanol, water, methanol, oxygen, isobutene, and methane

The apparent activation energy for TBHP pyrolysis is calculated to be approximately 20.8 kcal/mol

TBHP is primarily used as a polymerization initiator​ for monomers like styrene, vinyl chloride, and acrylics, and as an oxidizing agent​ in organic synthesis

It serves as a key oxidant in metal-catalyzed reactions, such as the Sharpless asymmetric epoxidation​ of allylic alcohols

It acts as a free radical initiator in the production of polystyrene, polyacrylics, ABS plastics, and as a cross-linking agent for unsaturated polyesters and rubber vulcanization

Yes, it is used in oxidative desulfurization to remove sulfur compounds from fuel oil

Yes, TBHP is commonly used in laboratory studies to induce oxidative stress​ in cells (e.g., hepatocytes) to investigate mechanisms of cell damage and antioxidant protection

Common solutions include 5.0-6.0 M in decane or nonane, and approximately 70% in water, which are safer to handle than the pure compound

TBHP is an oxidizing agent, flammable, corrosive, and harmful​ if inhaled, ingested, or upon skin contact. It poses fire and explosion risks, especially when heated, confined, or contaminated

Hazard statements include H241 (Heating may cause a fire or explosion), H302+H312+H332 (Harmful if swallowed, in contact with skin or if inhaled), and H314 (Causes severe skin burns and eye damage)

Recommended PPE includes chemical-resistant gloves, safety goggles, protective clothing, and use in a fume hood​ to avoid inhalation and skin contact

Store in a cool, well-ventilated area (2-8°C)​ away from heat, sparks, open flames, and incompatible materials like reducing agents, acids, and metals. Use containers made of stainless steel or high-density polyethylene

The oral LD₅₀ for rats is 406 mg/kg, and the dermal LD₅₀ for rats is 790 mg/kg, indicating moderate toxicity

Evacuate the area. Wear appropriate PPE. Contain the spill with non-combustible absorbent material. Avoid using water directly on the spill. Collect residue and dispose of as hazardous waste

Use dry chemical, CO₂, or foam. Do not use water jets directly, as it may spread the fire. Firefighters should wear self-contained breathing apparatus

The weak O-O bond (dissociation energy ~ 44 kcal/mol) readily undergoes homolytic cleavage to generate tert-butoxyl radicals, which initiate free radical chain reactions

The two primary initial reactions are peroxy bond (O-O) scission​ and hydrogen abstraction​ by the generated radicals

In the presence of metal catalysts like Mo or Ti, TBHP transfers an oxygen atom to an alkene, forming an epoxide. The tert-butoxyl group is a good leaving group, making the transfer efficient

The UN number for tert-Butyl Hydroperoxide is 3109​ (Class 5.2, Organic peroxide)

A recommended ceiling limit is 1.2 mg/m³ (0.3 ppm)​ based on its irritant properties

Dispose of in accordance with local, regional, national, and international regulations. It should be treated as hazardous waste​ and not released into the environment

TBHP is metabolized by cytochrome P450 enzymes, generating free radical intermediates that cause lipid peroxidation, glutathione depletion, and reactive oxygen species formation, leading to oxidative stress and cell damage

It is a standard tool to study oxidative stress-induced liver injury (hepatotoxicity) in vitro and in vivo, and to evaluate the protective effects of antioxidants

It is commonly sold as solutions, such as ~70% in water, 5.5-6.0 M in decane, or ~5.5 M in nonane, to enhance safety during transport and handling

High-purity solutions are available, for example, with a concentration of 55.4-75.0%​ (by titration) and impurities like water being less than 4%

Yes, it is used in catalytic asymmetric oxidations, such as the conversion of sulfides to sulfoxides using a chiral binaphthol auxiliary

TBHP oxidizes refractory sulfur compounds in fuel (like dibenzothiophene) to their corresponding sulfones, which can then be easily removed

It is used as a degrading agent for polypropylene fibers to improve dyeability and fabric performance

It has been mentioned as a chemical reagent in biological DNA sequencing applications

TBHP is incompatible with strong reducing agents, strong acids, strong bases, metals (and their salts), combustibles, and amines, as these can catalyze its violent decomposition

Molecular sieves can promote the decomposition of TBHP. Brief drying (e.g., 30 minutes) before use is acceptable, but prolonged contact is not recommended

Thermal decomposition can be self-accelerating, releasing heat and gas, potentially leading to a fire or explosion, especially if confined

The pKa of TBHP is approximately 12.80​ at 25°C, making it a relatively weak acid

ReaxFF molecular dynamics simulations provide atomistic insights into complex pyrolysis pathways and reaction mechanisms that are difficult to capture fully by experiment alone

According to the ChEBI database, TBHP is classified as an antibacterial agent​ and an oxidizing agent