ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Ketones spices > Aromatic ketone > Benzophenone
Basic information description Chemical Properties application Uses indicator Toxicity Production method Safety Related Supplier
Benzophenone Chemical Properties
- Melting point:47-51 °C(lit.)
- Boiling point:305 °C(lit.)
- Density 1.11
- vapor density 4.21 (vs air)
- vapor pressure 1 mm Hg ( 108 °C)
- FEMA 2134 | BENZOPHENONE
- refractive index 1.5893
- Flash point:>230 °F
- storage temp. Refrigerator
- solubility ethanol: soluble100mg/mL, clear, colorless (80% ethanol)
- form Crystalline Powder or Flakes
- color White to off-white
- Water Solubility insoluble (<0.1 g/100 mL at 25 ºC)
- JECFA Number831
- Merck 14,1098
- BRN 1238185
- Stability:Stable. Incompatible with strong oxidizing agents, strong reducing agents. Combustible.
- CAS DataBase Reference119-61-9(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzophenone(119-61-9)
- EPA Substance Registry SystemBenzophenone (119-61-9)
- Hazard Codes Xi,N,Xn,F
- Risk Statements 36/37/38-52/53-50/53-67-65-62-51/53-48/20-11-40
- Safety Statements 26-61-37/39-29-60-36-62-36/37-33-16-9
- RIDADR UN 3077 9/PG 3
- WGK Germany 2
- RTECS DI9950000
- F 10
- TSCA Yes
- HazardClass 9
- PackingGroup III
- HS Code 29143900
- Hazardous Substances Data119-61-9(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit 3535 mg/kg
Benzophenone Usage And Synthesis
- descriptionBenzophenone appears as colorless prismatic crystals, with sweetness and aroma of roses, melting point is 47-49 ℃, the relative density is 1.1146, refractive index is 1.6077. It is soluble in alcohol, ether, chloroform and other organic solvents and monomers, insoluble in water. It is a free radical photoinitiator, are mainly used in free radical UV curing systems , such as coatings, inks, adhesives and so on, and also used as the intermediates of organic pigments, pharmaceuticals, perfume, and insecticide . In the pharmaceutical industry, it is mainly used for the production of bicyclic Piperidine Benztropine hydrobromide, diphenhydramine hydrochloride. This product is styrene polymerization inhibitor and perfume fixative agent, to impart a sweet flavor with spices, widely used in the perfume and soap flavor. Attentions should be paid to the products to prevent moisture, sun , heat in the storage and transportation process, the temperature should not exceed 45 ℃.
- Chemical PropertiesShiny white prismatic crystals with a sweet taste, smell like a rose, melting point is 47-49 ℃, boiling point is 306 ℃, insoluble in water, soluble in alcohol, ether and chloroform.
- applicationSunscreen cosmetics is the hot new products of cosmetics, almost all sunscreens contain benzophenone compound on the current market. Benzophenone compounds that protect the skin from harm, often is used to produce high product. In recent years, the cosmetics consumption of benzophenone grows continuesly. Recent studies suggest that fluorescence is also a harmful ultraviolet light source, so benzophenone expands the range of applications in the field of cosmetics, it has been extended to hair conditioners, lotions and lipsticks. In addition, the perfume fixative agent also can give spice sweet flavor, is used in many perfumes and soap flavor.
Banana Boat company has developed a UVA ultraviolet-absorbing technology called AvoTriplex, which is benzophenone-based, adding a stabilizer to prevent the benzophenone from breaking down in the sun. Enhancer is also added into the formula, and stabilizer may act synergistically, to optimize benzophenone sunscreen capacity.
- Benzophenone Mainly used for the preparation of vanilla, butter and other flavor，It can be used as a fixative agent. Its weak sweet bay leaves fragrant , can be widely used in low-grade flavors, such as roses, bay leaves, sweet curd, shy flower, lily of the valley, sunflower, orchid, hawthorn flowers, incense and Wei Oriental flavor and other flavors. It is also used as an antioxidant in soaps, and occasionally used for almonds, berries, fruit, butter, nuts, peaches, vanilla beans and other food flavors in trace amount.
- Uses for photosensitive resins, coatings and adhesives.
- Benzophenone is an intermediate of UV absorbers, organic pigments, pharmaceuticals, perfume, insecticide . It is used for the production of bicyclic Piperidine Benztropine hydrobromide, diphenhydramine hydrochloride in the pharmaceutical industry . The product itself is a styrene polymerization inhibitor and a perfume fixative. Giving sweet taste to flavors, it is used in many perfumes and soap flavors.
- It is commonly used in soap flavor, used in ultraviolet absorbers, pigments, pharmaceuticals and reagents production, and also is low temperature fast curing agent for fluorine rubber. It serves to manufacturers to package the product in clear glass or plastic.
- Benzophenone is widely employed as a photo initiator in UV-curing applications such as inks, imaging and clear coatings in the printing industry. It acts as a UV blocker to prevent photo-degradation of the packaging polymers or its contents.
- It is light initiator for UV products, pharmaceutical intermediates, fragrances, light stabilizers etc.
- It is light pigment, medicine, perfume, pesticides intermediates, it can also be used for UV-curable resins, inks and coatings initiator.
- indicatorBenzophenone is widely used in the synthesis experiment as an indicator, it can be used as a indicator while handling toluene, benzene, THF, acetonitrile ect.; if there is a beautiful blue after added, it can be distillated and used, it is the best to kept in sodium, but the reason of generating blue is still a puzzle.
Here is the reason from a foreign book about reactions mechanism : 'a radical anion generated by the one called carbonyl radical, benzophenone acts as the indicator is that benzophenone oxygen atoms in sodium capture electrons to generate dark blue carbonyl radical; the radicals perspective on the electrical aspect is stable, mainly used to indicate 'anaerobic conditions',Widely used.
After the addition of benzophenone, more blue of the solution, indicating less oxygen in the solution, indirectly instructing the little water. However, whether the solution turns blue, is related to the added amount of benzophenone and processing solvent, THF (300ml) contains lots of water, and needs more than about 6 hours to reflux, and of course, it is related to the amount of processing solvent, the more the longer, toluene , benzene and other samples containing less aqueous need less reflux time, it is best to add the common desiccants to pretreat, such as: potassium carbonate, sodium sulfate, sodium hydroxide, etc., so that the processing time will be shortened.
- Production methodThere are different methods. 1. Condensation of benzyl chloride and benzene , and then by nitric acid oxidation. 2. The condensation of benzene and carbon tetrachloride, and then by hydrolysis. In the laboratory, the production is based on aluminum chloride as a catalyst, prepared by reacting benzene with benzoyl chloride.3.Condensation of benzene and benzoyl chloride in the presence of aluminum chloride, and then crystallized from ethanol.
- Chemical PropertiesOrange Crystals
- Chemical PropertiesBenzophenone is a combustible, white, crystalline solid with a rose-like odor
- Chemical PropertiesBenzophenone is a colorless, crystalline solid (mp 48.1 °C) with a rosy, slightly geranium-like odor. It can be prepared in several ways, for example, by Friedel–Crafts reaction of benzene and benzoyl chloride with aluminum chloride, or of benzene and carbon tetrachloride, and subsequent hydrolysis of the resulting ??,??-dichlorodiphenylmethane. Benzophenone can also be prepared by oxidation of diphenylmethane. It is used in flower compositions and as a fixative.
- Chemical PropertiesBenzophenone has a delicate, persistent, rose-like odor.
- OccurrenceReported found in Vitis vinifera L., black tea, cherimoya (Annona cherimola), mountain papaya (Carica pubescens) and soursop (Annona muricata L.)
- UsesIt is used in the manufacturing of antihistamines, hypnotics, insecticides.
- UsesReported to bind monsaccharides in the presence of polysaccharides
- UsesBenzophenone is used as a synthetic intermediate for manufacture of pharmaceuticals and agricultural chemicals. It is also used as a photoinitiator in UV-curable printing inks, as a fragrance in perfumes, as a flavor enhancer in foods. Benzophenone can be added as a UV-absorbing agent to plastics, lacquers, and coatings at concentrations of 2–8%.
- Production MethodsBenzophenone is commercially synthesized by the atmospheric oxidation of diphenylmethane using a catalyst of copper naphthenate. Alternatively, it can be produced by a Friedel–Crafts acylation of benzene using either benzoyl chloride or phosgene in the presence of aluminum chloride .
- PreparationBy Friedel–Craft condensation of benzene with benzoyl chloride in the presence of aluminum chloride.
- General DescriptionWhite solid with a flowery odor. May float or sink in water.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileKetones, such as Benzophenone, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. Benzophenone can react with oxidizing materials.
- Health HazardIngestion causes gastrointestinal disturbances. Contact causes eye irritation and, if prolonged, irritation of skin.
- Fire HazardFlash point data for Benzophenone are not available, but Benzophenone is probably combustible.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Contact allergensUnsubstituted benzophenone is largely used in chemical applications. It acts as a marker for photoallergy to ketoprofen.
- Safety ProfileModerately toxic by ingestion andintraperitoneal routes. Combustible when heated.Incompatible with oxidizers. When heated todecomposition it emits acrid and irritating fumes.
- Potential ExposureBenzophenone is used in UV curing of inks and coatings; as an intermediate; as an odor fixative in fragrances, flavoring, soaps; in the manufacture of pharmaceuticals and insecticides; in organic syntheses.
- CarcinogenicityLifetime dermal carcinogenicity studies in mice and rabbits did not show any tumor excess in the treated animals. Female Swiss mice and New Zealand White rabbits of both sexes were treated dermally with 0, 5, 25, or 50% of benzophenone (0.02 mL) twice a week for 120 or 180 weeks. Weekly examination of the rabbits did not reveal any reduction in survival or appearance of tumors. Mice treated with benzophenone did not show any excess in the number of tumor-bearing animals or in total number of tumors compared to untreated control animals. Although three skin tumors were observed in the benzophenone- treated mice (one case of squamous cell carcinoma and two cases of squamous cell papilloma), there were also three tumors (one carcinoma and toe papillomas) observed in the control animals.
- MetabolismBenzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol, which is excreted conjugated with glucuronic acid(Williams, 1959).
- ShippingUN1224 Ketones, liquid, n.o.s., Hazard Class: 3; Labels: 3—Flammable liquid, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous hazardous material, Technical Name Required.
- Purification MethodsCrystallise it from MeOH, EtOH, cyclohexane, *benzene or pet ether, then dry in a current of warm air and store it over BaO or P2O5. It is also purified by zone melting and by sublimation [Itoh J Phys Chem 89 3949 1985, Naguib et al. J Am Chem Soc 108 128 1986, Gorman & Rodgers J Am Chem Soc 108 5074 1986, Ohamoto & Teranishi J Am Chem Soc 108 6378 1986, Naguib et al. J Phys Chem 91 3033 1987]. [Beilstein 7 III 2048, 7 IV 1357.]
- IncompatibilitiesOxidizing materials, such as dichromates and permanganates.
Benzophenone Preparation Products And Raw materials
- Raw materialsBenzeneAluminium chlorideCarbon tetrachlorideBenzoyl chloridePHOSGENEAluminium chloride hexahydrate
- Preparation Products3-Azetidinecarboxylic acid4-Methoxytriphenylchloromethane1-N-Boc-3-hydroxyazetidine1-AMINOCYCLOPROPANECARBONITRILE2-AMINOPENT-4-YNENITRILEBenzophenone hydrazoneBenzophenone imine3-Methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-trieneFluotrimazolBenzhydrol2-Amino-5-nitrobenzophenoneBasic Blue 11Nizofenone4-Benzoyl AcetanilideClonazepamDifenidol hydrochlorideBENZP-DINITRIDE-THIO-KETONETAMPRAMINEN-Phenylbenzohydroxamic acidNordazepam3-BromobenzophenoneToremifenealpha-[1-(aminomethyl)propyl]benzhydryl alcohol 3,3'-DINITROBENZOPHENONE2-(alpha-hydroxybenzhydryl)butyronitrile 7-HYDROXYFLAVONEBenzopinacole
- 4,4'-Dichlorobenzophenone 2-Chloro-4'-fluorobenzophenone 2-acetamido-3-nitro-9-fluorenone 2,4,7-TRINITRO-9-FLUORENONE 2-NITROFLUORENONE 9-Fluorenone 2-Fluorobenzophenone 3-(TRIFLUOROMETHYL)BENZOPHENONE 2-FLUORO-9-FLUORENONE 3,4-Dichlorobenzophenone 4-Chlorobenzophenone 3-AMINO-9-FLUORENONE 2-(TRIFLUOROMETHYL)BENZOPHENONE 4-BROMOBENZOPHENONE 2,4'-Difluorobenzophenone 4-AMINO-9-FLUORENONE 2,4-Difluorobenzophenone 2,7-Dinitro-9-fluorenone
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