ベンゾフェノン 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶～結晶性粉末
定義
本品は、次の化学式で表される有機化合物である。
溶解性
エタノール及びアセトンに溶け、水にほとんど溶けない。
解説
diphenyl ketone．C13H10O(182.22)．C6H5COC6H5．ベンゾイルベンゼンともいう．ベンゼンと塩化ベンゾイル，あるいはベンゼン2分子とホスゲン1分子とのフリーデル-クラフツ縮合(フリーデル-クラフツ反応)によって合成される．安定形および不安定形の2形があり，安定形は融点49 ℃，沸点306 ℃，158 ℃(1.33 kPa)．d5041.087．n45D1.597．不安定形は融点26 ℃．ともに結晶．エタノール，エーテル，クロロホルムに可溶，水に不溶．還元すればジフェニルメタンあるいはベンズヒドロールが得られる．香料の固定剤として用いられる．また医薬品，農薬などの合成原料にも用いられる．LD50 2895 mg/kg(マウス，経口)．[CAS 119-61-9]
森北出版「化学辞典（第2版）
用途
1) 香料の固定剤, 2) 殺虫剤の原料
用途
環境試料中の内分泌攪乱物質のGCーMS分析で標準物質として使用されます。
用途
有機合成原料,医薬中間体,紫外線吸収剤,光重合開始剤
用途
ゼラニウムに似た芳香をもつ。香料の固定剤、医薬や農薬の合成中間体として用いられる。また光増感剤、光重合開始剤として用いられる。
化粧品の成分用途
褪色防止剤、香料
化学的特性
Benzophenone is a combustible, white, crystalline solid with a rose-like odor. soluble in ethanol, ether, chloroform and other organic solvents and monomers, insoluble in water. It is a free radical photoinitiator, mainly used in free radical UV curing systems, such as coatings, inks, adhesives, etc. 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 oxidation of diphenylmethane.
天然物の起源
Benzophenone has been found in various fruits, including Vitis vinifera L., black tea, cherimoya (Annona cherimola), mountain papaya (Carica pubescens), and soursop (Annona muricata L.).
使用
Benzophenone 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%.
調製方法
Benzophenone 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
.
定義
ChEBI: Benzophenone is the simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups. It has a role as a photosensitizing agent and a plant metabolite.
一般的な説明
Benzophenone(119-61-9) appears as white solid with a flowery odor. May float or sink in water. It is a widely used building block in organic chemistry, being the parent diarylketone.
空気と水の反応
Insoluble in water.
反応プロフィール
Ketones, 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.
健康ハザード
Ingestion causes gastrointestinal disturbances. Contact causes eye irritation and, if prolonged, irritation of skin.
火災危険
Flash point data for Benzophenone are not available, but Benzophenone is probably combustible.
接触アレルゲン
Unsubstituted benzophenone is largely used in chemical
applications. It acts as a marker for photoallergy to
ketoprofen.
安全性プロファイル
Moderately toxic by ingestion andintraperitoneal routes. Combustible when heated.Incompatible with oxidizers. When heated todecomposition it emits acrid and irritating fumes.
職業ばく露
Benzophenone 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.
発がん性
Lifetime 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.
代謝
Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol, which is excreted conjugated with glucuronic acid(Williams, 1959).
輸送方法
UN1224 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.
純化方法
Crystallise 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.]
不和合性
Oxidizing materials, such as dichromates
and permanganates.
ベンゾフェノン 上流と下流の製品情報
原材料
準備製品