133-14-2

Usage

Uses

Used in Silicone Rubber Industry:
2,4-Dichlorobenzoyl peroxide is used as a cross-linking agent for silicone rubber, enabling the material to withstand high temperatures of 150–400°C when exposed to hot air without pressure. This property makes DCBP an essential component in the production of silicone rubber products that require high thermal stability and resistance.

Reactivity Profile

May explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames. Peroxides are good oxidizing agents. Organic compounds can ignite on contact with concentrated peroxides. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively with peroxides. There are few chemical classes that do not at least produce heat when mixed with peroxides. Many produce explosions or generate gases (toxic and nontoxic). Generally, dilute solutions of peroxides (<70%) are safe, but the presence of a catalyst (often a transition metal such as cobalt, iron, manganese, nickel, or vanadium) as an impurity may even then cause rapid decomposition, a buildup of heat, and even an explosion. Solutions of peroxides often become explosive when evaporated to dryness or near-dryness.

Safety Profile

Poison by intraperitoneal route.Explosion Hazard: Pure compound is extremely shocksensitive and decomposes rapidly @ 80°. When heated todecomposition it emits toxic fumes of Cl-.

InChI:InChI=1/C14H6Cl4O4/c15-7-1-3-9(11(17)5-7)13(19)21-22-14(20)10-4-2-8(16)6-12(10)18/h1-6H

Synthetic route

2,4-dichlorobenzoyl chloride (89-75-8) → bis(2,4-dichlorobenzoyl)-peroxide (133-14-2)

Conditions	Yield
With (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sodium peroxide; acetone

o-chlorobenzoyl chloride (609-65-4) + 2,4-dichlorobenzoyl chloride (89-75-8) → bis(2,4-dichlorobenzoyl)-peroxide (133-14-2) + 2-chlorobenzoyl 2,4-dichlorobenzoyl peroxide (1198794-83-0)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water at 20℃; for 0.5h; Product distribution / selectivity;

tert-butylisonitrile (119072-55-8, 7188-38-7) + bis(2,4-dichlorobenzoyl)-peroxide (133-14-2) → N-(tert-butyl)-2,4-dichlorobenzamide (61176-08-7)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 120℃; for 12h; Sealed tube;	78%

bis(2,4-dichlorobenzoyl)-peroxide (133-14-2) → 2,2',4,4'-Tetrachlorobiphenyl (2437-79-8)

Conditions	Yield
Thermolysis.im Vakuum;

bis(2,4-dichlorobenzoyl)-peroxide (133-14-2) → 2,4 dichlorobenzoic acid (50-84-0) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + 2.4.2'.4'-tetrachloro-diphenyl

Conditions	Yield
im Vakuum;

Upstream product

• 89-75-8 2,4-dichlorobenzoyl chloride 
• 609-65-4 o-chlorobenzoyl chloride 

Downstream Products

• 2437-79-8 2,2',4,4'-Tetrachlorobiphenyl 
• 50-84-0 2,4 dichlorobenzoic acid 
• 15719-64-9 methylammonium carbonate 
• 61176-08-7 N-(tert-butyl)-2,4-dichlorobenzamide 

Relevant academic research and scientific papers

Preparation For Initiating Radical Reactions

A preparation, comprising a mixture of dibenzoyl peroxides where the mixture of dibenzoyl peroxides contains 50 to 99.7 mole % of a symmetric dibenzoyl peroxide and 0.3 to 50 mole % asymmetric dibenzoyl peroxides, shows a reduced decomposition temperature of the peroxides compared to the symmetric dibenzoyl peroxide and is suitable for hot cross-linking silicone rubber. The preparation can be produced by reacting a mixture containing a first benzoyl chloride and a second benzoyl chloride that is different therefrom with hydrogen peroxide, wherein the mixture of benzoyl chlorides contains 70 to 99.7 mole % of the first benzoyl chloride and 0.3 to 30 mole % of the second benzoyl chloride.