Chemical Properties
white powder or crystals
Uses
Benzoyl Peroxide is a widely used organic compound of the peroxide family. Benzoyl Peroxide is often used in acne treatments , bleaching and polymerizing polyester and many other uses.
Uses
Source of free radicals for industrial processes. Oxidizing agent in bleaching oils, flour, etc.; catalyst in the plastics industry; initiator in polymerization.
General Description
White, odorless powder, moderately toxic.
Reactivity Profile
BENZOYL PEROXIDE is most dangerous when BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] contains less then 1% water. A moisture content of 3% allowed slow burning only, and at 5% ignition did not occur [McCloskey, C. M. et al., Chem. Abs., 1967, 66, 12613c]. Mixed with a large surplus of water (30% or more) BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] is relatively safe. In dry form BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] is a very dangerous material; BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] will explode spontaneously when heated above melting point (103° C). An explosion which occurred when a screw-capped bottle of the peroxide was opened was attributed to friction initiating a mixture of peroxide Ind organic dust in the cap threads [Lappin, G. R., Chem. Eng. News, 1948, 26, p.3518]. A violent explosion occurred during purification of the peroxide by Soxhlet extraction with hot chloroform [Anon., Sichere Chemiearb., 1976, 28, p. 49]. BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] is a powerful oxidizer, BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] ignites readily and burns rapidly. In contact with reducing agents BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] may ignite by spontaneous chemical reaction. BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] must be kept in a cool place in isolation, out of the sunlight or sources of heat, avoid shock or friction. BENZOYL PEROXIDE, [> 77% BUT < 95% WITH WATER] reacts violently with inorganic or organic acids, alcohols, amines, metallic naphthenates and polymerization accelerators (e.g., N,N-dimethylaniline). Explosive or violent reaction on contact with dimethyl sulfide, lithium aluminum hydride or aniline [Bretherick, 5th ed., 1995, p. 1140]. Mixture with carbon tetrachloride and ethylene explodes when exposed to heat [Bolt, R. O. et al., Chem. Eng. News, 1947, 25, p. 1866]. Ignition occurred on contact with methyl methacrylate [MCA Case History No. 996], polymerization of vinyl acetate in ethyl acetate accelerated out of control leading to ignition and explosion [Vervalin, 1973, p. 81]. At 50° C a mixture of dibenzoyl peroxide and charcoal reacts violently producing dense white smoke of benzoic acid, benzene, phenyls and carbon dioxide [Leleu, Cahiers, 1980, 99, p. 279].
Air & Water Reactions
Insoluble in water.
Hazard
Highly toxic via inhalation. May explode
spontaneously when dry (<1% of water). Never mix
unless at least 33% water is present. Skin and upper
respiratory tract irritant. Questionable carcinogen.
Potential Exposure
Used as polymerization initiator, curing
agent, and cross-linking agent.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy.
Shipping
UN3104 : Organic peroxide type C, solid, Hazard
Class: 5.2; Labels: 5.2—Organic peroxide, Technical
Name Required. UN3108 : Organic peroxide type E, solid, Hazard
Class: 5.2; Labels: 5.2—Organic peroxide, Technical
Incompatibilities
May explode when heated above melting
point, 103 C. A strong oxidizer. Extremely explosionsensitive
to heat, shock, friction, and concussion. May
explode or cause fire on contact with reducing agents; combustible
substances, organic substances, wood, paper, metal
powders, lithium aluminum hydride. Violent reaction with
alcohols, organic and inorganic acids, and amines.
Description
Benzoyl Peroxide (94-36-0) may affect workers in the electronics and plastics (epoxy resins and catalysts) industries, electricians,
ceramic workers, dentists and dental technicians,
laboratory technicians and bakers. As it was
contained in candles, it also induced contact dermatitis
in a sacristan. However, some positive tests are of
unknown occupational relevance.
Waste Disposal
Pretreatment involves decomposition
with sodium hydroxide. The final solution of
sodium benzoate, which is very biodegradable, may be
flushed into the drain. Disposal of large quantities of solution
may require pH adjustment before release into the
sewer or controlled incineration after mixing with a
noncombustible material.
Definition
ChEBI:Benzoyl peroxide is a carbonyl compound.
Indications
Benzoyl peroxide is a potent oxidizing agent that has
both antimicrobial and comedolytic properties; its primary
use is in treating acne vulgaris. It is converted in
the skin to benzoic acid; clearance of absorbed drug is
rapid, and no systemic toxicity has been observed. The
major toxicities are irritation and contact allergy.
Outgrowth of bacteria resistant to topical antibiotics
used to treat acne can be reduced by the addition of benzoyl
peroxide in combination products such as erythromycin
(Benzamycin) and clindamycin (Benzaclin).
Brand name
Acne-Aid Cream (Stiefel); Benoxyl (Stiefel); Benzac
(Galderma); Benzac W (Galderma); Brevoxyl (Stiefel);
Clear By Design (SmithKline Beecham); Dry and Clear
(Whitehall-Robins); Epi-Clear (Bristol-Myers Squibb);
Fostex BPO Bar, Gel, and Wash (Bristol-Myers Products);
Loroxide (Dermik); PanOxyl (Stiefel); Persa-Gel (Ortho
Pharmaceutical); Vanoxide (Dermik);Altex.
World Health Organization (WHO)
Benzoyl peroxide slowly releases oxygen and hence is
bactericidal. It is also keratolytic, antiseborrheic and irritant. It is used in the
treatment of acne. Benzoyl peroxide is listed in the WHO Model List of Essential
Drugs.
Health Hazard
The health hazard from benzoyl peroxideis low. It can cause irritation of the skin,mucous membranes, and eyes. An intraperitonealinjection of 250 mg/kg was lethal toadult mice. Systemic toxicity in humans isnot known. It may be mild to moderatelytoxic on an acute basis. The oral LD50 valuein rats is 7710 mg/kg (NIOSH 1986). Itstoxicity from inhalation is low; an LC50 valueof 700 ppm in mice is suggested (ACGIH1986).
Benzoyl peroxide may cause gene damageand DNA inhibition. It has been foundto cause skin tumor. The evidence of its carcinogenicityin animals and humans is inadequate.
Fire Hazard
Benzoyl peroxide can cause a major fire
and explosion hazard. It is highly flammable
and a strong oxidizer; autoignition temperature
80°C (176°F). It ignites instantly. The
rate and violence of decomposition and the
potential ease of such ignition or decomposition
have been experimentally measured
by Noller et al. (1964). Lead pipe deformation
(LPD), pressure vessel test (PVT), and
self-accelerating decomposition test (SADT)
have been performed to measure these explosive
characteristics. Heating 5 g of benzoyl
peroxide in an aluminum tester containing an
aperture vent and 6-atm rupture disk, caused
the disk to blow up in 95 seconds when the
aperture vent area was less than 174.7 mm2.
Redried material was more violent. The
decomposition hazard was greatly reduced
with wet and diluted benzoyl peroxide.
Noller et al. (1964) measured the SADT
temperature at 82.2°C (180°F), above which
the decomposition was self-accelerating, sudden,
and produced smoke.
Benzoyl peroxide is a deflagrant, posing
a severe explosion hazard. The compound
is sensitive to heavy shock, such as impact
or blows, as well as to friction and heat.
Especially in the dry state, it is highly
dangerous.
A water sprinkler should be used to extinguish
fires. Water should be used to keep the
containers cool.
reaction suitability
reagent type: oxidant
Safety Profile
Poison by intraperitoneal route.Can cause dermatitis, asthmatic effects, testicular atrophy,and vasodilation. An allergen and eye irritant. Humanmutation data reported. Questionable carcinogen withexperimental tumorigenic data. Moderate fire hazard by
Veterinary Drugs and Treatments
Benzoyl peroxide products are used topically either as gels or in shampoos. Shampoos are generally used for seborrheas, greasy skin (seborrhea
oleosa), or crusty pyodermas (such as seborrheic dermatitis/pyoderma commonly seen in Cocker Spaniels). Gels may be useful
for treating recurrent localized skin infections (e.g., chin acne), localized Demodex lesions, superficial and deep pyodermas (adjunctive
therapy), seborrhea oleosa, and Schnauzer comedo syndrome.
Benzoyl peroxide possesses antimicrobial (especially antibacterial), keratolytic and antiseborrheic actions. It also is It has some mild
antipruritic activity and wound healing effects, and is thought to increase follicular flushing. Benzoyl peroxide’s antimicrobial activity is
due to the oxidative benzoyl peroxy radicals formed that disrupt cell membranes.
Carcinogenicity
When repeatedly applied to the
skin of mice, BPO was not carcinogenic . However,
benzoyl peroxide is a tumor promoter in mice and hamsters,
but has shown no complete carcinogenic or tumor-initiating
activity . There has been one controversial Japanese
report that was interpreted as BPO being a complete
carcinogen. However, when the data were critically evaluated,
it was found consistent with BPO acting as a skin tumor
promoter and not as a carcinogen. The International Agency
for Research on Cancer (IARC) has evaluated the carcinogenicity
of benzoyl peroxide. They classified it as Group 3.
This means there is limited or inadequate evidence of carcinogenicity
for animals and inadequate or absent information
for humans. In addition, there are other animals and in vitro
studies that continue to support the lack of carcinogenic or
mutagenic properties for BPO .
Source
Benzoyl peroxide (BPO) was originally derived from chlorhydroxyquinoline, a component of coal tar. Currently, BPO is usually prepared by treating hydrogen peroxide with benzoyl chloride.
storage
Benzoyl peroxide should be stored in acool and well-ventilated area, isolated fromother chemicals and free of heating andelectrical installations. Dry compound maybe shipped in polyethylene-lined paper bagsor fiber containers packed in wooden boxeso.
Purification Methods
Dissolve benzoyl peroxide in CHCl3 at room temperature and precipitate it by adding an equal volume of MeOH or pet ether. Similarly it is precipitated from acetone by adding two volumes of distilled water. It has also been crystallised from 50% MeOH and from diethyl ether. Dry it under vacuum at room temperature for 24hours. Store it in a desiccator in the dark at 0o. When purifying in the absence of water it can be EXPLOSIVE, and operations should be done on a very small scale with adequate protection. Large amounts should be kept moist with water and stored in a refrigerator. [Kim et al. J Org Chem 52 3691 1987, Beilstein 9 IV 777.]
