Benzoyl peroxide

From Wikipedia, the free encyclopedia

Benzoyl peroxide
IUPAC name	Dibenzoyldioxidane
Molecular formula	C14H10O4
Molar mass	242.23 g/mol
CAS number	[94-36-0]
Density	1.334 g/cm3
Solubility	Poor
Melting point	103–5 °C decomp.
SMILES	c1ccccc1C(=O)OOC(=O)c2ccccc2
Hazards
EU classification	Explosive (E) Irritant (Xi)
EU Index	617-008-00-0
NFPA 704	4 1 4 OX
R-phrases	R2, R36, R43
S-phrases	(S2), S3/7, S14, S36/37/39
Autoignition temperature	80°C
RTECS number	DM8575000
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Tube of Basiron, a water-based 5% benzoyl peroxide preparation for the treatment of acne.

A bleached fabric stain caused by contact with a benzoyl peroxide containing consumer product.

Benzoyl peroxide (pronounced /ˈbɛnzɔɪl pəˈrɒksaɪd/) is a chemical in the organic peroxide family. It consists of two benzoyl groups (benzaldehyde with the H of aldehyde removed) joined by a peroxide group. Acceptable condensed structural formulae would include C₆H₅-COO-OOC-C₆H₅, PhCO-O-O-COPh, and (PhCO)₂O₂. It is often abbreviated Bz₂O₂.

[edit] Uses

Benzoyl peroxide is used as a radical initiator. Homolytic cleavage of the weak oxygen-oxygen bond forms benzoyl free radicals which trigger further reactions.

Jack Breitbart of Revlon laboratories first developed benzoyl peroxide's use for treating acne in the 1920s.^[1] It is typically placed over the affected areas in gel or cream form, in concentrations of 2.5% increasing through the usually effective 5% to up to 10%. Research suggests that 5 and 10% concentrations are not significantly more effective than 2.5% and 2.5% is usually better tolerated.^[2][3] It commonly causes initial dryness and sometimes irritation, although skin tolerance usually occurs after a week or so. A small percentage of people are much more sensitive to it and liable to suffer burning, itching, peeling and possibly swelling^[4]. It is sensible to apply the lowest concentration and build up as appropriate. Once tolerance is achieved, increasing the quantity or concentration a second time and gaining tolerance at a higher level usually gives better subsequent acne clearance. Benzoyl peroxide works as a peeling agent, increasing skin turnover and clearing pores, thus reducing the bacterial count there as well as directly as an antibacterial.

Other common uses for benzoyl peroxide include dyeing hair, and as an active ingredient in teeth whitening systems. It is also used in the preparation of flour, and can be used as an initiator and catalyst for polyester thermoset resins (as an alternative to the much more hazardous methyl ethyl ketone peroxide).

[edit] Adverse effects

In a 1977 study using a human maximization test, 76% of subjects acquired a contact sensitation to benzoyl peroxide. Formulations of 5% and 10% were used.^[5]

[edit] Safety

Pure benzoyl peroxide is highly flammable, explosive, toxic and a possible tumor promoter and may act as a mutagen^[6], and should be handled with care.

Diluted in an ointment, benzoyl peroxide is used as an acne treatment and the following precautions and claims pertain to this use. Attention should be paid to the safety directions provided when purchased.

In the United States, the typical concentration for benzoyl peroxide is 2.5% to 10% for both prescription and over the counter use in treatment for acne. Higher concentrations are used for hair bleach and teeth whitening. Benzoyl peroxide, like most peroxides, is a powerful bleaching agent. Contact with fabric (including clothing and bed linens) or hair can cause permanent color dampening almost immediately. Even secondary contact can cause bleaching. For example, contact with a towel that has been used to wash off benzoyl peroxide-containing hygiene products.^{[citation needed]}

Benzoyl peroxide breaks down in contact with skin, producing benzoic acid and oxygen, neither of which are significantly toxic.^[7]

[edit] Synthesis

Benzoyl peroxide is usually prepared by reacting sodium peroxide with benzoyl chloride to give benzoyl peroxide and sodium chloride.

2 PhCOCl + Na₂O₂ → (PhCO)₂O₂ + 2 NaCl

[edit] Decomposition

The half-life of benzoyl peroxide is one hour at 92°C. At 131°C, the half-life is one minute. ^[8]

[edit] References

[edit] External links

• International Chemical Safety Card 0225
• NIOSH Pocket Guide to Chemical Hazards 0052
• IARC Monograph "Benzoyl peroxide."
• Benzoyl Peroxide
• Information on Benzoyl Peroxide Application - Acne.org Daniel Kern's acne treatment regimen