酢酸フェニル水銀

解説

酢酸フェニル水銀略称PMA，PMAC．アセトキシ(フェニル)水銀ともいう．酢酸水銀(Ⅱ)をベンゼン中でトリフルオロシリルベンゼンとともに加熱還流するか，または，ジフェニル水銀と酢酸との反応により合成する．無色ないし白色の針状晶，または葉状晶．融点149 ℃．アセトン，ベンゼン，クロロホルムに可溶，水に難溶．SH試薬として作用する．殺菌力が強く，1～6万倍の希釈液でも効力を有する．昇汞(こう)HgCl2のようにタンパク質と結合しないので，タンパク質が存在する場合でも殺菌力は低下しない．農業用の殺菌剤として実用されたが，現在，わが国では使用禁止となっている．LD50 40 mg/kg(ラット，経口)．

用途

防カビ剤、殺菌剤

効能

抗菌性保存剤

化学的特性

Phenylmercuric acetate occurs as a white to creamy white, odorless or almost odorless, crystalline powder or as small white prisms or leaflets.

使用

Phenylmercuric acetate is used as catalyst; fungicide; herbicide; algicide; preservative in antibiotic eye drops, eye cosmetics, shampoos, etc.

調製方法

Phenylmercuric acetate is readily formed by heating benzene with mercuric acetate.

一般的な説明

Small lustrous prisms. Toxic by ingestion, inhalation and skin absorption. May severely irritate skin and eyes. Used as an herbicide and fungicide. as such, is mixed with organic solvent for the purpose of application.

反応プロフィール

PHENYLMERCURIC ACETATE may react with strong oxidizing agents .

健康ハザード

Extremely toxic. The probable oral lethal dose for humans is 5-50 mg/kg, between 7 drops and 1 teaspoonful for a 70 kg (150 lb.) person.

火災危険

Fire may produce irritating or poisonous gases. When heated to decomposition, very toxic mercuric fumes may be given off. Phenylmercuric ion is incompatible with halides, with which precipitates are formed.

応用例（製薬）

Phenylmercuric acetate is used as an alternative antimicrobial preservative to phenylmercuric borate or phenylmercuric nitrate in a limited range of cosmetics (in concentrations not exceeding 0.007% of mercury calculated as the metal) and pharmaceuticals. It may be used in preference to phenylmercuric nitrate owing to its greater solubility.
Phenylmercuric acetate is also used as a spermicide;

安全性プロファイル

Poison by ingestion, intravenous, intraperitoneal, subcutaneous, and possibly other routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. See also MERCURY COMPOUNDS. When heated to decomposition it emits toxic fumes of Hg.

安全性

Phenylmercuric acetate is mainly used as an antimicrobial preservative in topical pharmaceutical formulations. A number of adverse reactions to mercury-containing preservatives have been reported; see Phenylmercuric Nitrate.
LD₅₀ (chicken, oral): 60 mg/kg
LD₅₀ (mouse, IP): 13 mg/kg
LD₅₀ (mouse, IV): 18 mg/kg
LD₅₀ (mouse, oral): 13 mg/kg
LD₅₀ (mouse, SC): 12 mg/kg
LD₅₀ (rat, oral): 41 mg/kg

職業ばく露

Phenylmercury acetate is used as an antiseptic, fungicide; for fungal and bacterial control; herbicide and control of crabgrass; mildewcide for paints; slimicide in paper mills. It was also used in contraceptive gels and foams.

環境運命予測

If released into air, soil, or water, phenylmercuric acetate is unlikely to volatilize and is instead expected to be bound to particulates based on a low vapor pressure (6 × 10^-6 mm Hg) and low Henry’s constant (5.66 × 10^-10 atmm3 mol ^-1). Photolysis has the potential to degrade phenylmercuric acetate, releasing inorganic mercury which can volatilize and enter the atmosphere from superficial soils or water. If released into soil, the mobility of parent phenylmercuric acetic acid is expected to be high based on a Koc of 60. Water releases would result in quick dispersion since water solubility is high (4370 mg l^-1). Once in solution, especially with harder water, it will dissociate into a salt. The cation will adsorb to particulates or humics suspended in the water column or in sediment, with little bioconcentration in aquatic species.

貯蔵

As for other phenylmercuric salts; see Phenylmercuric Nitrate.
Phenylmercuric acetate should be stored in a well-closed container, protected from light, in a cool, dry place.

輸送方法

UN1674 Phenylmercuric acetate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

純化方法

It forms small colourless lustrous prisms from EtOH. Its solubility in H2O is 0.17%, but it is more soluble in EtOH, Me2CO and *C6H6. [Maynard J Am Chem Soc 46 1510 1925, Coleman et al. J Am Chem Soc 59 2703 1937, J Am Pharm Assoc 25 752 1936, Beilstein 16 IV 1720.] See PhHgOH below.

不和合性

As for other phenylmercuric salts; see Phenylmercuric Nitrate.
Incompatible with: halides; anionic emulsifying agents and suspending agents; tragacanth; starch; talc; sodium metabisulfite; sodium thiosulfate; disodium edetate; silicates; aluminum and other metals; amino acids; ammonia and ammonium salts; sulfur compounds; rubber; and some plastics.
Phenylmercuric acetate is reported to be incompatible with cefuroxime and ceftazidime.

廃棄物の処理

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. React to produce soluble nitrate form, precipitate as mercuric sulfide. Return to supplier.

規制状況(Regulatory Status)

Included in the FDA Inactive Ingredients Database (ophthalmic ointments; topical emulsions/creams; vaginal emulsions/creams). Included in the Canadian List of Acceptable Non-medicinal Ingredients (ophthalmic, nasal and otic preparations up to 0.004%; there must be no other suitable alternative preservative available).
Phenylmercuric acetate is no longer permitted to be used as a pesticide in the USA. Its use in cosmetic products in the USA is limited to eye area cosmetics at not more than 0.0065% provided that there is no other suitable available preservative. It is specifically prohibited in vaginal contraceptive drug products and antimicrobial diaper rash drug products in the USA. Phenylmercuric compounds are prohibited from use in cosmetic products in Canada.
In Europe, use in cosmetic products is limited to eye makeup and eye makeup remover at concentrations not exceeding 0.007% mercury alone or in combination with other permitted mercurial compounds.In France, a maximum concentration of 0.01% is permitted for use in pharmaceuticals. The use of mercurial compounds in cosmetics in Japan is limited to concentrated shampoo or cream at not more than 0.003% Hg and eye makeup at not more than 0.0065% Hg.