Product Description
Overview:
Tert-Butyl peroxybenzoate, with CAS number 614-45-9, is an organic perester commonly used in industrial settings. It has a chemical formula of C11H14O3 and a molar mass of 194.23 g/mol, making it a key compound in chemical manufacturing.
Specifications and Properties:
This compound is a pale yellow liquid with a density of 1.021 g/mL and a boiling point of 75-76 °C at 0.2 mmHg. It melts at 8-9 °C and contains 8.16 wt% active oxygen, with a self-accelerating decomposition temperature of 60 °C. These properties make it stable under controlled conditions, which is important for industrial processes.
Uses and Benefits:
It is primarily used as a radical initiator for polymerization reactions, such as producing low-density polyethylene (LDPE), vinyl chloride, styrene, and acrylic esters. It also acts as a crosslinking catalyst for unsaturated polyester resins and is involved in grafting reactions and thin film preparation. Research suggests it offers benefits like efficient initiation and safe handling compared to other peroxides, making it valuable for industrial polymer production. However, it’s not typically used in consumer products, which might be unexpected for some users.
Product Details: Comprehensive Description
Tert-Butyl peroxybenzoate, identified by CAS number 614-45-9, is an organic perester with the molecular formula C11H14O3 and a molar mass of 194.23 g/mol. It is a pale yellow liquid, primarily encountered as a solution in solvents like ethanol or phthalate, which aligns with its industrial application needs. The compound’s chemical properties, as detailed below, make it suitable for high-temperature reactions and controlled environments.
| Property | Value |
|---|---|
| Chemical Formula | C11H14O3 |
| Molar Mass | 194.23 g/mol |
| Density | 1.021 g/mL at 25 °C (lit.) |
| Boiling Point | 75-76 °C/0.2 mmHg (lit.) |
| Melting Point | 8-9 °C |
| Active Oxygen Content | 8.16 wt% |
| Self-Accelerating Decomposition Temperature (SADT) | 60 °C |
| Half-Life | 10 hours at 104 °C, 1 hour at 124 °C, 1 minute at 165 °C |
| Vapor Density | 6.7 (vs air) |
| Vapor Pressure | 3.36 mmHg at 50 °C |
| Refractive Index | n20/D 1.499 (lit.) |
| Solubility in Water | Soluble, 1.18 g/L |
| Storage Temperature | 10 °C minimum (below solidification) to 50 °C maximum |
| Main Decomposition Products | Carbon dioxide, acetone, methane, tert-butanol, benzoic acid, benzene |
| Safety Note | Considered one of the safest peresters or organic peroxides in handling |
The compound’s stability is enhanced by dilution with high-boiling solvents, increasing its SADT, which is critical for safe storage and transportation. Decomposition is accelerated by amines, metal ions, strong acids, bases, and reducing or oxidizing agents, necessitating careful handling in industrial settings.
Applications and Uses
Tert-Butyl peroxybenzoate is extensively used in polymer chemistry as a radical initiator for polymerization reactions, including the production of low-density polyethylene (LDPE) from ethylene, vinyl chloride, styrene, and acrylic esters. It is also a curing agent for unsaturated polyester resins (UP resins), typically used at 1-2% quantity, though it may lead to benzene formation, which is a consideration for applications like LDPE packaging films.
Beyond polymerization, it serves as a crosslinking catalyst in thermoset composites and acrylics production, as noted by Nouryon’s product data for Trigonox C. It is also employed in organic chemistry for synthesizing protecting groups, such as 2-trimethylsilylethanesulfonyl chloride (SES-Cl), via reactions with vinyltrimethylsilane and sodium hydrogensulfite. Other uses include introducing benzoyloxy groups in allyl positions of unsaturated hydrocarbons (e.g., 71-80% yield for 3-benzoyloxycyclohexene from cyclohexene with Cu(I)Br) and enabling Kharasch-Sosnovsky oxidation for racemic allylic benzoates (up to 80% yield with Cu(II) trifluoromethanesulfonate, DBN/DBU). It oxidizes oxazolines and thiazolines to oxazoles and thiazoles with Cu(I)/Cu(II) salts and facilitates oxidative coupling of benzene and furans with olefins under Pd catalysis, using TBPB as a hydrogen acceptor. Additionally, it supports benzoxylation of aromatics without Pd²⁺ salts, broadening its utility in synthetic chemistry.
The benefits include efficient initiation, safe handling compared to other organic peroxides, and support for industrial-scale polymer production, making it a preferred choice for manufacturers. However, its industrial focus means it is not typically relevant for consumer applications, which may be an unexpected detail for lay audiences.
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