Dilauroyl peroxide
[CAS# 105-74-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: Dilauroyl peroxide
• Synonyms: Dodecanoyl peroxide; Lauroyl peroxide
• Molecular Formula: C₂₄H₄₆O₄
• Molecular Weight: 398.62
• CAS Registry Number: 105-74-8
• EC Number: 203-326-3
• SMILES: CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC

Properties

• Density: 0.91 g/mL
• Melting point: 53-57 ºC

Safety Data

• Hazard Symbols: GHS02 Danger
• Hazard Statements: H242
• Precautionary Statements: P210-P234-P235-P240-P280-P370+P378-P403-P410-P411-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Organic peroxides	Org. Perox.	D	H242
Organic peroxides	Org. Perox.	C	H242
Self-reactive substances or mixtures	Self-react.	D	H242
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2124;UN 3106

Discovory and Applicatios

Dilauroyl peroxide, a white crystalline solid with the chemical formula C₂₄H₄₆O₄, is an organic peroxide widely used as an initiator in polymerization processes, particularly in the production of plastics and rubber. This compound, derived from lauric acid, plays a crucial role in initiating the polymerization of various monomers, making it a vital component in the manufacturing of synthetic materials.

The discovery of dilauroyl peroxide can be traced back to early studies on organic peroxides, where researchers explored the potential of these compounds as initiators in free-radical polymerization. Dilauroyl peroxide was identified as particularly effective due to its stability and ability to decompose at relatively low temperatures, generating free radicals that initiate the polymerization process. The synthesis of dilauroyl peroxide typically involves the reaction of lauric acid with hydrogen peroxide in the presence of a catalyst, yielding the peroxide compound with desirable properties for industrial applications.

One of the primary applications of dilauroyl peroxide is in the polymerization of styrene, a key monomer used in the production of polystyrene and other styrene-based polymers. The peroxide acts as an initiator, decomposing upon heating to generate free radicals that trigger the polymerization of styrene monomers into long-chain polymers. This process is fundamental to the production of a wide range of plastic products, including packaging materials, insulation, and consumer goods.

In addition to its use in styrene polymerization, dilauroyl peroxide is also employed in the vulcanization of rubber. Vulcanization is a chemical process that involves the cross-linking of rubber molecules to enhance their elasticity, strength, and durability. Dilauroyl peroxide serves as a cross-linking agent in this process, facilitating the formation of covalent bonds between rubber chains. This results in a more resilient material that is widely used in tires, seals, and various industrial products.

Beyond polymerization and vulcanization, dilauroyl peroxide is also used in the formulation of coatings, adhesives, and sealants. Its ability to initiate polymerization under controlled conditions makes it valuable in producing high-performance materials with specific mechanical and chemical properties. Additionally, dilauroyl peroxide has been utilized in the synthesis of copolymers, where it helps achieve the desired balance of flexibility, hardness, and thermal stability.

Despite its widespread use, the handling of dilauroyl peroxide requires careful consideration due to its reactive nature. As an organic peroxide, it is sensitive to heat, friction, and impact, which can lead to decomposition and potential hazards. Therefore, it is typically handled and stored under controlled conditions to ensure safety during its use in industrial processes.

Dilauroyl peroxide remains an essential chemical in the production of plastics, rubber, and other synthetic materials. Its discovery and application have had a profound impact on the development of modern materials, contributing to advancements in manufacturing technologies and product performance across various industries.

References

2024. Comparison between conventional and additive processing of polylactic acid subjected to multiple recycling and lauroyl peroxide additivation. Progress in Additive Manufacturing, 9(5), 1-14.
DOI: 10.1007/s40964-024-00799-3

2020. Systematic process hazard assessment of three kinds of solid organic peroxides with kinetic analysis and heat transfer equilibrium. Journal of Thermal Analysis and Calorimetry, 141(5), 1745-1757.
DOI: 10.1007/s10973-020-09732-6

2021. One-pot synthesis of cross-linked nonspherical polystyrene particles via dispersion polymerization: the effect of polymerization conditions on the morphology of the particles. Journal of Polymer Research, 28(1), 1-12.
DOI: 10.1007/s10965-020-02387-9