Di-tert-butyl peroxide
[CAS# 110-05-4]

Identification

• Classification: Inorganic chemical industry >> Inorganic salt >> Oxides and peroxides >> Non-metal oxides and peroxides
• Name: Di-tert-butyl peroxide
• Synonyms: tert-Butyl peroxide; DTBP
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• CAS Registry Number: 110-05-4
• EC Number: 203-733-6
• SMILES: CC(C)(C)OOC(C)(C)C

Properties

• Density: 0.796
• Melting point: -30 °C
• Boiling point: 109-110 °C
• Refractive index: 1.388-1.390
• Flash point: 34 °F
• Water solubility: immiscible

Safety Data

• Hazard Symbols: GHS02;GHS08 Danger
• Risk Statements: H225-H242-H341
• Safety Statements: P203-P210-P233-P234-P235-P240-P241-P242-P243-P260-P264+P265-P271-P273-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P318-P337+P317-P342+P316-P370+P378-P403-P403+P235-P405-P410-P411-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Organic peroxides	Org. Perox.	E	H242
Flammable liquids	Flam. Liq.	2	H225
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Self-reactive substances or mixtures	Self-react.	E	H242
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 3107

Discovery and Applications

Di-tert-butyl peroxide (DTBP) is an organic peroxide used as a free radical initiator and is widely used in polymer chemistry and various industrial processes. Its stability and effectiveness in generating free radicals under heating make it a valuable reagent in numerous chemical reactions. DTBP was synthesized in the early 20th century as part of the exploration of organic peroxides. These compounds gained interest due to their ability to decompose and generate free radicals, which are essential for initiating various chemical reactions. The synthesis of DTBP involves the reaction of tert-butyl hydroperoxide with tert-butyl alcohol. The compound quickly gained recognition due to its stability and effectiveness as an initiator of choice in free radical polymerization processes.

The applications of DTBP are very wide, ranging from polymer chemistry to the fuel and pharmaceutical industries. DTBP is widely used as a free radical initiator in polymerization reactions. Its ability to decompose into free radicals at moderate temperatures makes it effective in polymerizing monomers such as ethylene, styrene, and vinyl acetate. This process is essential for the production of various polymers including polyethylene and polystyrene.

In the rubber and plastics industry, DTBP acts as a crosslinking agent. It helps to form crosslinked structures in polymers, thereby enhancing their mechanical strength and heat resistance. This application is essential for manufacturing durable rubber products and high-performance plastics.

DTBP is used as a cetane improver in diesel fuel. By promoting more complete combustion, it can improve fuel efficiency and reduce emissions. Its role in improving ignition quality is particularly beneficial in cold weather, where diesel engines face difficulties starting.

In medicine, DTBP is used as an oxidant in the synthesis of various compounds. Its ability to introduce oxygen into chemical structures is valuable in the production of active pharmaceutical ingredients and intermediates.

DTBP, like other organic peroxides, must be handled with care. It is stable under normal conditions but can decompose explosively if exposed to heat or contamination. Proper storage, away from heat and incompatible materials, and the use of protective equipment are essential to ensure safety.

References

1948. The Reaction of Di-t-butyl Peroxide and Benzaldehyde. Journal of the American Chemical Society.
DOI: 10.1021/ja01190a016

2023. Additives to Biodiesel Fuels. Chemistry and Technology of Fuels and Oils.
DOI: 10.1007/s10553-023-01611-8

2024. Enantioselective alkyl-alkyl coupling by Ni-catalysed asymmetric cross-hydrodimerization of alkenes. Nature Synthesis.
DOI: 10.1038/s44160-024-00609-2