Quick Search
Dibenzoyl Peroxide (DBPO) is a chemical compound (specifically, an organic peroxide) with structural formula (C6H5−C(=O)O−)2, often abbreviated as (BzO)2.
In terms of Dibenzoyl Peroxide (DBPO)'s structure, the molecule can be described as two benzoyl (C6H5−C(=O)−, Bz) groups connected by a peroxide (−O−O−).
Dibenzoyl Peroxide (DBPO) is a white granular solid with a faint odour of benzaldehyde, poorly soluble in water but soluble in acetone, ethanol, and many other organic solvents.
CAS: 94-36-0
MF: C14H10O4
MW: 242.23
EINECS: 202-327-6
SynonymsBenzoyl peroxide Manufacturer;Luperox A98, Benzoyl peroxide;Benzoyl peroxide[51% < content ≤100%, inert solid content ≤48%];Benzoyl peroxide[35% < content ≤52%, inert solid content ≥48%];Benzoyl peroxide[36% < content ≤42%, type A diluent ≥18%, water content ≤40%];Benzoyl peroxide[77% < content ≤94%, water content ≥6%];Benzoyl peroxide[content ≤42%, stable dispersion in water];Benzoyl peroxide[content ≤62%, inert solid content ≥28%, water content ≥10%];BENZOYL PEROXIDE;94-36-0;Peroxide, dibenzoyl;Dibenzoyl peroxide;Benzoyl superoxide;Benzoperoxide;Benoxyl;Lucidol;Acetoxyl;Oxylite;Panoxyl;Persadox;Benzol peroxide;Dibenzoylperoxid;Diphenylglyoxal peroxide;Benzoylperoxid;Luperco AST;Asidopan;Loroxide;Theraderm;Benzac;Eloxyl;Mytolac;benzoyl benzenecarboperoxoate;Resdan Akne;Epi-Clear;Persa-Gel;Akneroxid 5;Dry and Clear;Duresthin 5;Nayper BO;Benzoylperoxyde;Debroxide;Novadelox;Vanoxide;Acnegel;Incidol;Garox;Topex;Xerac;Dibenzoylperoxyde;Luperox fl;Peroxyde de benzoyle;Cadox bs;Quinolor compound;Lucidol B 50;Lucidol G 20;Perossido di benzoile;Luperco AA;Nayper B and bo;benzoylperoxide;Aztec BPO;Benzoic acid, peroxide;Benzaknen;Brevoxyl;Desanden;Akneroxide L;Norox bzp-250;Norox bzp-C-35;Desquam E;Benzac W;Clear By Design;Cadox B;Benzagel 10;Lucidol (peroxide);Benzagel;Benzashave;Superox 744;Cadox 40E;Desquam X;Desquam-X;Acne-Aid Cream;Benbel C;Oxy 5;Cadox B-CH 50;Cadat BPO;Lucidol-70;Aksil 5;Lucidol 50P;Benzaknew;Benzefoam;Lucidol KL 50;Oxy-10 Cover;Chaloxyd BP 50FT;Abcat 40;Benox 50;Cadet;Diphenylperoxyanhydride;benzoic peroxyanhydride;Cadox B 40E;Cadox B 50P;Cadox B 70W;Oxy-5;BZF-60;Fostex BPO;pHisoAc BP;Peroxide, Benzoyl;Xerac BP;Benzoyl peroxide [USAN];Lucidol 75FP;Superoxide, Benzoyl;Benoxyl (5&10) Lotion;Epi Clear Antiseptic Lotion;EPSOLAY;Stri-dex B.P.;OXY WASH;Peroxyderm;Benzoyl;Dermoxyl;Luzidol;Nericur;OXY-10;Peroxydex;Preoxydex;Sanoxit;Superox;Benzoylperoxid [German];Bepio;benzoyl-peroxide;dibenzoylperoxide;Benzoyl peroxyde;Ins no.928;Diphenylglyoxal Superoxide;NSC-671;NSC-675;Akneroxid L;Anhydrous benzoyl peroxide;Benzoyl peroxide anhydrous;Dibenzoylperoxid [German];W9WZN9A0GM;Clearasil Antibacterial Acne Lotion;Superoxide, Diphenylglyoxal;Clearasil bp acne treatment;Nyper B;BPO;Ins-928;Nyper BMT;Cuticura acne cream;Lucidol 70;Lucidol 78;Oxy-L;component of Oxy-5;component of Vanoxide;NSC671;Xerac BP 5;DTXSID6024591;Clearasil benzoyl peroxide lotion;Cadet BPO 78W;Xerac BP 10;Hydrous benzoyl peroxide
Dibenzoyl Peroxide (DBPO) was first prepared and described by Justus von Liebig in 1858.
Donald Holroyde Hey FRS (12 September 1904 – 21 January 1987) was a Welsh organic chemist who inferred that the decomposition of Dibenzoyl Peroxide (DBPO) generated free phenyl radicals.
Dibenzoyl Peroxide (DBPO) is an oxidizer, which is principally used in the production of polymers.
Dibenzoyl Peroxide (DBPO) is mainly used in production of plastics and for bleaching flour, hair, plastics and textiles.
As a bleach, Dibenzoyl Peroxide (DBPO) has been used as a medication and a water disinfectant.
As a medication, Dibenzoyl Peroxide (DBPO) is mostly used to treat acne, either alone or in combination with other treatments.
Some versions are sold mixed with antibiotics such as clindamycin.
Dibenzoyl Peroxide (DBPO) is on the World Health Organization's List of Essential Medicines.
Dibenzoyl Peroxide (DBPO) is available as an over-the-counter and generic medication.
Dibenzoyl Peroxide (DBPO) is also used in dentistry for teeth whitening.
In 2021, Dibenzoyl Peroxide (DBPO) was the 284th most commonly prescribed medication in the United States, with more than 700,000 prescriptions.
Although the precise cause of acne is unclear, Dibenzoyl Peroxide (DBPO) appears to be associated with at least four factors: increased sebum production, follicular keratinisation, bacterial colonisation and inflammation.
Study suggests the prevalent bacterium implicated in the clinical course of acne is Propionibacterium acnes (P acnes), a gram-positive anaerobe that normally inhabits the skin and is implicated in the inflammatory phase of acne.
Dibenzoyl Peroxide (DBPO) is mainly indicated in the treatment of mild to moderate acne and is often prescribed in conjunction with oral antibiotics (erythromycin or clindamycin) in the treatment of moderate to severe acne.
Dibenzoyl Peroxide (DBPO) is lipophilic that can penetrate the stratum corneum and enter the pilosebaceous follicle.
Dibenzoyl Peroxide (DBPO) is rapidly broken down to benzoic acid and hydrogen peroxide and generates free radicals that oxidise proteins in bacterial cell membranes, exerting a bactericidal action.
In addition, Dibenzoyl Peroxide (DBPO) has shown that benzoyl peroxide can reduce the free fatty acid content of sebum, which provides a useful marker for bacterial activity.
Dibenzoyl Peroxide (DBPO) has an anti-inflammatory action and vitro studies suggest that this action arises from its ability to kill polymorphonuclear leukocytes (PMN cells) in the pilosebaceous follicles and so prevent their release of reactive oxygen species such as peroxides which enhance tissue inflammation.
Involving equation about this process:
C6H5C(O)O-OC(O)C6H5 + H2O 2 C6H5COOH + ½ O2
Moreover, due to its irritant effect, Dibenzoyl Peroxide (DBPO) increases turnover rate of epithelial cells, thereby peeling the skin and promoting the resolution of comedones.
Dibenzoyl Peroxide (DBPO) is used as a bleaching agent for certain foods, an oxidizing agent, a polymerizing initiator in the manufacture of plastics, a curing agent for silicone rubber, and an ingredient in various industrial processes.
Dibenzoyl Peroxide (DBPO), like most peroxides, is a powerful bleaching agent.
Dibenzoyl Peroxide (DBPO) has a long history of use in the food industry as a bleaching agent added for flour, whey, and milk for cheese making.
Contact with fabrics or hair can cause permanent color dampening almost immediately.
Even secondary contact can cause bleaching.
Dibenzoyl Peroxide (DBPO) is widely used as a catalyst in the polymerisation of molecules like styrene (phenylethene) to form polystyrene, which used to make many things from drinking cups to packaging material.
Dibenzoyl Peroxide (DBPO) 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 Dibenzoyl Peroxide (DBPO) was contained in candles, it also induced contact dermatitis in a sacristan.
However, some positive tests are of unknown occupational relevance.
Dibenzoyl Peroxide (DBPO) is a carbonyl compound.
Classically, Dibenzoyl Peroxide (DBPO) is thought to have a three-fold activity in treating acne.
Dibenzoyl Peroxide (DBPO) is sebostatic, comedolytic, and inhibits growth of Cutibacterium acnes, the main bacterium associated with acne.
In general, acne vulgaris is a hormone-mediated inflammation of sebaceous glands and hair follicles.
Hormone changes cause an increase in keratin and sebum production, leading to blocked drainage.
C. acnes has many lytic enzymes that break down the proteins and lipids in the sebum, leading to an inflammatory response.
The free-radical reaction of Dibenzoyl Peroxide (DBPO) can break down the keratin, therefore unblocking the drainage of sebum (comedolytic).
Dibenzoyl Peroxide (DBPO) can cause nonspecific peroxidation of C. acnes, making it bactericidal, and it was thought to decrease sebum production, but disagreement exists within the literature on this.
Some evidence suggests that Dibenzoyl Peroxide (DBPO) has an anti-inflammatory effect as well.
In micromolar concentrations Dibenzoyl Peroxide (DBPO) prevents neutrophils from releasing reactive oxygen species, part of the inflammatory response in acne.
Dibenzoyl Peroxide (DBPO) is a reagent extensively used in pharmaceutical manufacturing, particularly in topical medications for acne treatment.
Dibenzoyl Peroxide (DBPO) acts as an oxidizing agent and is also employed in polymer chemistry.
Dibenzoyl Peroxide (DBPO) appears as a white granular solid or powder.
Dibenzoyl Peroxide (DBPO) Chemical Properties
Melting point: 105 °C(lit.)
Boiling point: 176°F
Density: 1.16 g/mL at 25 °C(lit.)
Vapor pressure: 0.009Pa at 25℃
Refractive index: 1.5430 (estimate)
Fp: >230 °F
Storage temp.: 2-8°C
Solubility: 0.35mg/l
Form: powder
Color: White
Odor: odorless
Water Solubility: Insoluble
Merck: 14,1116
BRN: 984320
Exposure limits: TLV-TWA 5 mg/m3; IDLH 7000 mg/m3.
Stability: Strong oxidizer. Highly flammable. Do not grind or subject to shock or friction. Incompatible with reducing agents, acids, bases, alcohols, metals, organic materials. Contact with combustible material, heating or friction may cause fire or explosion.
InChIKey: OMPJBNCRMGITSC-UHFFFAOYSA-N
LogP: 3.2 at 20℃
CAS DataBase Reference: 94-36-0(CAS DataBase Reference)
IARC: 3 (Vol. 36, Sup 7, 71) 1999
NIST Chemistry Reference: Dibenzoyl Peroxide (DBPO)(94-36-0)
EPA Substance Registry System: Dibenzoyl Peroxide (DBPO) (94-36-0)
Dibenzoyl Peroxide (DBPO) is an odorless, white, or colorless crystalline powder with a faint odor of benzaldehyde resulting from the interaction of benzoyl chloride and a cooled sodium peroxide solution.
Dibenzoyl Peroxide (DBPO) is used in specified cheeses at 0.0002% of milk level.
Dibenzoyl Peroxide (DBPO) is also used for the bleaching of flour, slowly decomposing to exert its full bleaching action, which results in whiter flour and bread.
The major decomposition product of Dibenzoyl Peroxide (DBPO) in water was benzoic acid, but trace amounts of phenyl benzoate, phenol, and hydroxybenzoic acids were formed.
When carbon-14 la- beled Dibenzoyl Peroxide (DBPO) was reacted with whey, the same compounds were produced.
Structure and reactivity
The original 1858 synthesis by Liebig reacted Dibenzoyl Peroxide (DBPO) with barium peroxide, a reaction that probably follows this equation:
2 C6H5C(O)Cl + BaO2 → (C6H5CO)2O2 + BaCl2
Dibenzoyl Peroxide (DBPO) is usually prepared by treating hydrogen peroxide with benzoyl chloride under alkaline conditions.
2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
The oxygen–oxygen bond in peroxides is weak.
Thus, Dibenzoyl Peroxide (DBPO) readily undergoes homolysis (symmetrical fission), forming free radicals:
(C6H5CO)2O2 → 2 C6H5CO•2
The symbol • indicates that the products are radicals; i.e., they contain at least one unpaired electron.
Such species are highly reactive.
The homolysis is usually induced by heating.
The half-life of benzoyl peroxide is one hour at 92 °C.
At 131 °C, the half-life is one minute.
In 1901, Dibenzoyl Peroxide (DBPO) was observed that the compound made the tincture of guaiacum tincture turn blue, a sign of oxygen being released.
Around 1905, Loevenhart reported on the successful use of Dibenzoyl Peroxide (DBPO) to treat various skin conditions, including burns, chronic varicose leg tumors, and tinea sycosis.
He also reported animal experiments that showed the relatively low toxicity of the compound.
Treatment with Dibenzoyl Peroxide (DBPO) was proposed for wounds in 1929, and for sycosis vulgaris and acne varioliformis in 1934.
However, preparations were often of questionable quality.
Dibenzoyl Peroxide (DBPO) was officially approved for the treatment of acne in the US in 1960.
Polymerization
Dibenzoyl Peroxide (DBPO) is mainly used as a radical initiator to induce chain-growth polymerization reactions, such as for polyester and poly(methyl methacrylate) (PMMA) resins and dental cements and restoratives.
Dibenzoyl Peroxide (DBPO) is the most important among the various organic peroxides used for this purpose, a relatively safe alternative to the much more hazardous methyl ethyl ketone peroxide.
Dibenzoyl Peroxide (DBPO) is also used in rubber curing and as a finishing agent for some acetate yarns.
Uses
Dibenzoyl Peroxide (DBPO) is a widely used organic compound of the peroxide family.
Dibenzoyl Peroxide (DBPO) is used as a source offree radicals in many organic syntheses andto initiate polymerizations of styrene, vinylchloride, vinyl acetate, and acrylics; to curethermoset polyester resins and silicone rubbers;in medicine for treating acne; and forbleaching vegetable oil, cheese, flour, and fats.
Dibenzoyl Peroxide (DBPO) is mainly used as a monomer polymerous cause of polyvinyl chloride, unsaturated polyester, polyacrylate and other monomers.
Dibenzoyl Peroxide (DBPO) can also be used as a cross -linked agent for polyethylene and can also be used as a rubber sulfur.
1. Dibenzoyl Peroxide (DBPO) gel is an external oxidant for skin.
The concentration is 2.5%, 5% and 10%.
Dibenzoyl Peroxide (DBPO) may be sterilized by the slow release of the protein of the new ecological oxygen oxidizing bacteria, and has an antibacterial effect against Propionibacterium acnes.
Dibenzoyl Peroxide (DBPO) is also effective against anaerobic infections.
At the same time, Dibenzoyl Peroxide (DBPO) has mild keratin dissolution, desquamation and the action of reducing free fatty acids in the hair follicles of hair follicles.
2. Dibenzoyl Peroxide (DBPO) is the most widely used initiator in the adhesive industry.
Dibenzoyl Peroxide (DBPO) is used as acrylate, vinyl acetate solvent polymerization, neoprene, natural rubber, SBS and methyl methacrylate graft polymerization.
An unsaturated polyester resin cured, an initiator such as a plexiglass adhesive.
Dibenzoyl Peroxide (DBPO) can also be used as a vulcanizing agent and a crosslinking agent for silicone rubber and fluororubber.
Also used as a bleaching agent and oxidizing agent.
Other uses
Dibenzoyl Peroxide (DBPO) is effective for treating acne lesions.
Dibenzoyl Peroxide (DBPO) does not induce antibiotic resistance.
Dibenzoyl Peroxide (DBPO) may be combined with salicylic acid, sulfur, erythromycin or clindamycin (antibiotics), or adapalene (a synthetic retinoid).
Two common combination drugs include benzoyl peroxide/clindamycin and adapalene/benzoyl peroxide, adapalene being a chemically stable retinoid that can be combined with benzoyl peroxide unlike tezarotene and tretinoin.
Combination products such as Dibenzoyl Peroxide (DBPO)/clindamycin and benzoyl peroxide/salicylic acid appear to be slightly more effective than benzoyl peroxide alone for the treatment of acne lesions.
The combination tretinoin/benzoyl peroxide was approved for medical use in the United States in 2021.
Dibenzoyl Peroxide (DBPO) for acne treatment is typically applied to the affected areas in gel, cream, or liquid, in concentrations of 2.5% increasing through 5.0%, and up to 10%.
No strong evidence supports the idea that higher concentrations of Dibenzoyl Peroxide (DBPO) are more effective than lower concentrations.
Reactivity Profile
Dibenzoyl Peroxide (DBPO) reacts exothermically withstrong acids, strong bases, amines, reducingagents, and sulfur compounds.
Explosions have been reported when Dibenzoyl Peroxide (DBPO) reacted withcarbon tetrachloride and ethylene, lithium aluminum hydride, N,N-dimethyl aniline, hot chloroform, and methyl methacrylate.
Lappin (1948) reported an explosionwhen a bottle was opened.
Organic matterentrapped in the threads of the bottleprobably reacted explosively with benzoylperoxide.
