2-フェニルフェノール

外観

白色〜わずかにうすい褐色, 結晶〜粉末

定義

本品は、次の化学式で表わされる芳香族化合物である。

溶解性

水に難溶 (30mg/L)。エタノール, アセトン, エーテルに易溶。各種有機溶媒に可溶。エタノール及びアセトンに溶けやすく、水にほとんど溶けない。

解説

2-フェニルフェノール、2-（あるいはオルト）ヒドロキシビ（あるいはジ）フェニルともいう。無色の鱗片(りんぺん)状の結晶。比較的穏やかであるが、特有の臭気がある。水には実質的には溶けないが、ほとんどの有機溶媒に可溶。ラットに経口投与したときの50％生存量はキログラム当り2.48グラム。日本では1970年代後半までは殺菌剤としての使用が禁止されていたため、この薬品で処理した果実の輸入が問題とされた。

用途

食品添加物試験用

用途

合成樹脂原料、染色キャリアー、各種合成原料、殺菌剤、防腐剤

用途

有機合成原料、防カビ剤、殺菌剤。

化粧品の成分用途

防腐剤、忌避剤.殺虫剤、殺菌剤、香料

効能

殺菌消毒薬

特長

特異臭のある結晶～結晶性粉末

説明

2-phenylphenol(OPP) is a broad spectrum fungicide used to protect crops in storage. It is highly soluble in water, moderately voatile but is not expected to be persistent in the environment. OPP is more selective than other free phenols but does produce phytotoxic effects.

化学的特性

o-Phenylphenol is a white to buff-colored crystalline solid with a distinct odor. When heated to decomposition, it emits acrid smoke and irritating fumes.

使用

2-Phenylphenol is a agriculture fungicide and is no longer used as a food additive.

調製方法

OPP is produced as a by-product in the manufacture of diphenyl oxide or by aldol condensation of hexazinone.

定義

ChEBI: 2-Phenylphenol is a member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits. It has a role as an environmental food contaminant and an antifungal agrochemical. It derives from a hydride of a biphenyl.

製造方法

2-Phenylphenol can be recovered from the distillation residue of the process of phenol production via sulfonation. The phenol distillation residue contains about 40% of phenyl phenol with the other components including phenol, inorganic salts, water and so on. After vacuum distillation, the mixed phenyl phenol fraction is separated out with the vacuum being 53.3-66.7kPa. The temperature, started to be cut at 65-75 ℃ to until 100 ℃ above, but should not higher than 1345 ℃. Then take advantage of the solubility difference of ortho, p-hydroxy biphenyl in the trichlorethylene, the two are separated into pure product. The mixed material (mainly 2-hydroxy biphenyl and 4-hydroxy biphenyl) is heated to be dissolved in the trichlorethylene, after cooling, first precipitate out 4-hydroxy biphenyl crystal. After centrifuge filtration, dry to obtain 4-hydroxy biphenyl. The mother liquor was washed with a sodium carbonate solution, followed by dilute alkaline to make the 2-hydroxybiphenyl salt. After standing stratification, take the upper 2-hydroxybiphenyl sodium salt for dehydration under reduced pressure, namely, sodium salt products. The 2-hydroxybiphenylsodium salt is white to light red powder, being easily soluble in water with the solubility in 100g of water being 122g. The pH value of the 2% aqueous solution is 11.1-12.2. It is also easily soluble in acetone, methanol, soluble in glycerol, but insoluble in oil. The sodium salt of 2-hydroxy biphenyl, after acidification, can lead to the formation of 2-hydroxy biphenyl with both of them being food additives.

主な応用

2-phenylphenol is remarkably versatile organic chemical products, widely used antiseptic, auxiliaries and surfactant synthesis of new plastics, resins and polymer materials in areas such as stabilizers and flame retardants. It is used for the post-harvest control of storage diseases of apples, citrus fruit, stone fruit, tomatoes, cucumbers and other vegetables. It is also used for the protection of textiles and timber and as a fungistat in water-soluble paints.

一般的な説明

Light lavender crystals or solid.

空気と水の反応

Insoluble in water.

反応プロフィール

2-Phenylphenol react as a weak organic acid. Exothermically neutralizes bases. May react with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides to generate flammable gas (H2) and the heat of the reaction may ignite the gas. Is sulfonated very readily (for example, by concentrated sulfuric acid at room temperature) in exothermic reactions. May be nitrated very rapidly. Nitrated phenols often explode when heated and also form metal salts that tend toward detonation by rather mild shock. Can react with oxidizing agents .

火災危険

2-Phenylphenol is combustible.

农业用途

Fungicide, Disinfectant, Microbiocide: Used to make fungicides. Also used to make dye stuffs and rubber chemicals, but used primarily as a disinfectant cleaner. Registered for use in the U.S. and U.K.

製品名

ANTHRAPOLE 73®; DOWCIDE-1®; Invalon OP®; KIWI LUSTR-277®; NECTRYL®; PREVENTOL-O Extra®; REMOL TRF®; TETROSIN OE®; TETROSIN OE-N®; TORSITE®; TUMESCAL OPE®

安全性プロファイル

A poison by intraperitoneal route.Moderately toxic by ingestion and possibly other routes.An experimental teratogen. Other experimentalreproductive effects. Human mutation data reported.Severe eye and moderate skin irritant. Questionablecarcinogen wi

職業ばく露

o-Phenylphenol is used in the manufacture of plastics, resins, rubber, as Agricultural chemical, in making fungicides; as an intermediate in making dye stuffs and rubber chemicals; a germicide; used in food packaging.

発がん性

IARC classified SOPP as a B2 carcinogen in 1983, based on reports from Japan that high dietary levels of this sodium salt caused bladder tumors in male rats. Both sodium saccharin and sodium cyclamate also cause bladder tumors at high doses in male rats, but classification of these food additives as B2 carcinogens was recently rescinded by IARC at a meeting in 1998.
The U.S. National Toxicology Program conducted a skin painting study with OPP in groups of 50 mice per sex. The OPP was applied as an acetone solution on 3 days per week for 2 years, both alone and as a promoter with DMBA. No skin neoplasms were observed in either sex treated with OPP alone, and there were no tumor enhancing or inhibiting effects when OPP and DMBA were given in combination.

代謝経路

2-Phenylphenol is not used on growing plants because it is too phytotoxic and there appears to be no information published on its metabolism in plants. Its widespread use as a preservative, disinfectant and fungistat on stored food (either by direct application or impregnated in packaging) requires studies on its environmental fate and metabolism in mammals. Several studies in mammals are available and the compound has been the subject of an evaluation by the UK MAFF Pesticide Safety Directorate (PSD); the results have been published (PSD, 1993). This evaluation was prompted by the discovery of bladder tumours in rats treated with high doses of the compound.
2-Phenylphenol is also used as the sodium and potassium salts where water solublity is important. No information is available specifically on the latter. The metabolism of the free phenol and the sodium salt have been studied separately. Once absorbed into a cell, provided that internal pH control is maintained, the two forms should be indistinguishable.

輸送方法

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

純化方法

Crystallise it from pet ether. [Beilstein 6 IV 4579.]

Toxicity evaluation

2-phenylphenol has a moderate to low toxicity to biodiversity. This substance has a low oral mammalian toxicity, is carcinogenic, a neurotoxin and recognised irritant. 2-Phenylphenol and its sodium salt have a low acute toxicity in mammals when administered orally, with LD50 values ranging from 600 to 3500 mg/kg of body weight.
http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1340.htm

Degradation

2-Phenylphenol is readily degraded in surface waters and municipal waste mixtures, and the degradation is biologically mediated. In river water, radiolabelled 2- phenylphenol at concentrations ranging from 1.2 to 120 μg/litre was degraded to about 50% of the initial concentration in 1 week. The addition of mercuric chloride to inhibit biological activity reduced the decrease to only 10% after 30 days. In activated sludge, radiolabelled 2-phenylphenol at 9.6 mg/litre was degraded to 50% of the initial concentration in 24 h. 2-Phenylphenol therefore meets the criteria to be classified as readily biodegradable (FAO/WHO, 1999).

不和合性

Strong bases, strong oxidizers

廃棄物の処理

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.