クレゾール 化学特性,用途語,生産方法
外観
本品は無色又は黄色～黄褐色澄明の液で，フェノールの
ようなにおいがある．
本品はエタノール(95)又はジエチルエーテルと混和する．
本品は水にやや溶けにくい．
本品は水酸化ナトリウム試液に溶ける．
本品の飽和水溶液はブロモクレゾールパープル試液に対し
て中性である．
本品は光を強く屈折させる．
本品は光により，また，長く放置するとき，暗褐色となる．
定義
本品は、オルトクレゾール、メタクレゾール及びパラクレゾールの混合物である。
解説
クレゾール，工業的にクレゾールといえばこれらの混合物である．石炭タールの酸性油留分中に存在するが，トルエンからスルホン化-アルカリ融解法あるいはクメン法により合成される．o-およびp-クレゾールは常温で結晶または液体，m-クレゾールは液体で，いずれもフェノール臭をもち，空気中ではしだいに着色してくる．酸性を示し，希アルカリに可溶．エタノール，エーテル，クロロホルムなどとまざる．
森北出版「化学辞典（第2版）
用途
殺菌力があり・消毒・防腐剤に、また合成樹脂の原料などに利用。
化粧品の成分用途
防腐剤、香料
効能
殺菌消毒薬
主な用途／役割
溶剤型接着剤に使用される。
確認試験
本品の飽和水溶液5mLに希塩化鉄(Ⅲ)試液1～2滴を
加えるとき，液は青紫色を呈する.
純度試験
(１) 炭化水素 本品1.0mLを水60mLに溶かすとき，その
混濁は次の比較液より濃くない．
比較液：水54mLに0.005mol/L硫酸6.0mL及び塩化バリウ
ム試液1.0mLを加えてよく振り混ぜた後，5分間放置す
る．
(２) イオウ化合物 本品20mLを100mLの三角フラスコに
とり，フラスコの口に潤した酢酸鉛(Ⅱ)紙をおき，水浴上で
5分間加温するとき，酢酸鉛(Ⅱ)紙は黄色を呈することがあ
っても，褐色又は暗色を呈しない．
貯法
保存条件 遮光して保存する．
容器 気密容器．
説明
Professions that involve dealing with the combustion of
coal or wood may be exposed to higher levels of cresols than
the general population. Environmental tobacco smoke is also
a source of cresol exposure. Average cresol concentration may
vary between the brand and type of cigarette in a 45-cubic
meter chamber after six cigarettes had been smoked (ranged
from 0.17 to 3.9 mg m3), although low levels of cresol can be
detected in certain foods and tap water, and these do not
constitute major sources of exposure for most population.
Detectable levels of cresols have been reported in several consumer products including tealeaves, tomatoes, and ketchup
as well as butter, oil, and various cheeses. Exposure to children
occurs by the same routes that affect adults. Children are likely
to be exposed to cresols through inhalation of contaminated air
from automobile exhaust, waste incineration, and secondhand
smoke.
化学的特性
Cresol,a clear amber to red liquid, also known as cresylic acid, methylphenol, and tricresol,is a mixture of three isomers of cresol derived from coaltar and is used in making plastics, ore flotation, refining petroleum, and as a strong antiseptic. Orthocresol is a color less solid with a melting point of 30 °C(86 OF) that is soluble in alcohol,but only slightly soluble in water. It is used in making disinfectants and as a plasticizer. Metacresol is a colorless liquid used in the manufacture of photographic developers,printing inks, and paint removers.It is also used as a leather preservative.The least soluble isomer, paracresol, is a colorless solid and is used in the production of dyes and pharmaceuticals.
使用
Cresol is used in disinfectants and fumigants,in the manufacture of synthetic resins, inphotographic developers and explosives.
調製方法
Cresol may be obtained from coal tar or prepared synthetically by either sulfonation or oxidation of toluene.
定義
A mixture of isomers obtained from coal tar or
petroleum.
一般的な説明
Colorless to yellow liquids with a tarry odor. Flash point 178°F. Insoluble in water. Density 8.7 lb / gal. Poisonous by ingestion and skin absorption and corrosive to skin.
空気と水の反応
Insoluble in water.
反応プロフィール
Mixing CRESOL in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, nitric acid, oleum, [NFPA 1991].
危険性
Irritant, corrosive to skin and mucous membranes, absorbed via skin. Questionable carcinogen.
健康ハザード
The toxic actions of cresol are similar tothose of phenol. The para-isomer is somewhat more toxic than the other two isomers.The toxic symptoms are weakness, confu-sion, depression of the central nervous system, dyspnea, and respiratory failure. It isan irritant to the eyes and skin. Skin con-tact can cause burn and dermatitis. Chroniceffects are gastrointestinal disorders, nervousdisorders, tremor, confusion, skin eruptions,oliguria, jaundice, and liver damage. SkinLD50 values in rats for o-, m-, and p-phenolsare 620, 1100, and 750 mg/kg, respectively.
Dietz and Mulligan (1988a,b) have investigated the subchronic toxicity of meta- andpara-cresols in Sprague-Dawley rats after13 weeks of oral gavage. There was noadverse effects from a dose of 50 mg/kg/day.High dose levels of 150 mg/kg/day producedcentral nervous system depression and reduction of body weight gain. p-Cresol was foundto be hepatotoxic and nephrotoxic, inducinga mild anemic effect. The acute toxicity ofmethyl phenols did not show any relationshipto the number or position of methyl groupson the phenol nucleus. In an acute toxicitystudy on Daphnia magna, Devillers (1988)found cresols to be more toxic than phenol,xylenols, and trimethylphenols.
火災危険
Combustible. POISONOUS GASES MAY BE PRODUCED IN FIRE. Flammable toxic vapors given off in a fire. Sealed closed containers can build up pressure if exposed to heat.
化学反応性
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
応用例（製薬）
Cresol is used at 0.15-0.3% concentration as an antimicrobial preservative in intramuscular, intradermal, and subcutaneous injectable pharmaceutical formulations. It is also used as a preservative in some topical formulations and as a disinfectant. Cresol is not suitable as a preservative for preparations that are to be freeze-dried.
安全性
Reports of adverse reactions to cresol are generally associated with the use of either the bulk material or cresol-based disinfectants, which may contain up to 50% cresol, rather than for its use as a preservative. However, a recent case of cutaneous hypersensitivity reaction to the m-cresol component of an insulin formulation detected via intradermal and patch testing has been reported.
Cresol is similar to phenol although it is less caustic and toxic. However, cresol is sufficiently caustic to be unsuitable for skin and wound disinfection. In studies in rabbits, cresol was found to be metabolized and excreted primarily as the glucuronide.
A patient has survived ingestion of 12g of cresol though with severe adverse effects.
LD50 (mouse, oral): 0.76g/kg
LD50 (rabbit, skin): 2g/kg
LD50 (rat, oral): 1.45g/kg
職業ばく露
Cresol is used as a disinfectant and fumigant; as an ore flotation agent, and as an intermediate in the manufacture of chemicals, dyes, plastics, and antioxidants. A mixture of isomers is generally used; the concentrations of the components are determined by the source of the cresol.
環境運命予測
It acts by disruption of the cell membrane by denaturation of
proteins and enzymes of the cell.
貯蔵
Cresol and aqueous cresol solutions darken in color with age and on exposure to air and light. Cresol should be stored in a well-closed container, protected from light, in a cool, dry place.
輸送方法
UN2076 Cresols, liquid, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material. UN3455 Cresols, solid, Hazard class: 6.1; Labels: 6.1- Poisonous materials, 8-Corrosive material.
不和合性
Cresol has been reported to be incompatible with chlorpromazine. Antimicrobial activity is reduced in the presence of nonionic surfactants.
廃棄物の処理
Wastewaters may be subjected to biological treatment. Concentrations may be further reduced by ozone treatment. High concentration wastes may be destroyed in special waste incinerators.
規制状況(Regulatory Status)
Included in the FDA Inactive Ingredients Database (IM, IV, intradermal, and SC injections). Included in parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
クレゾール 上流と下流の製品情報
原材料
準備製品