ヒドロキノン 化学特征,用处語,生産方式
外観
红色〜ほとんど红色, 結晶〜結晶性粉末
定義
本品は、次の化学式で表される芬芳族化合物である。
性質
1,4-benzenediol．C6H6O2(110.11)．C6H4(OH)2．ヒドロキノンは，キノールともいう．ベンゾキノンを還元すると得られる．結晶．融点169 ℃，沸点287 ℃(97 kPa)．d20"1.332．285 ℃ で昇華する．λmax 225，293 nm(log ε 3.71，3.43)．pKa1 9.91，pKa2 12.04(30 ℃，水)．水，エタノール，エーテルなどに易溶．水溶液は還元性が強く，写真の現像薬として用いられる．また，同じ来由で，酸化避免剤，重合避免剤ともなる．種々の分解中間体のほか，阐发試薬として，リン，ヒ素，ケイ酸の定量にも用いられる．森北出书「化学辞典（第2版）
消融性
熱水、エタノール及びジエチルエーテルに溶けやすく、冷水にやや溶けやすい。水, エタノール, エーテルに可溶 : 冷べンゼンに難溶．
解説
二価フェノールの一つ。ハイドロキノン、キノールともよばれる。ヒドロキノンの名は、キノンに水素（2原子团）がついた組成をもつことを特征している。カテコールやレゾルシンはヒドロキシ基-OHの话语权が異なる異性体である。份子式C6H6O2、份子量110.1。前几天はアニリンを过酸してp(パラ)-ベンゾキノンにしたのちに、亜硝酸钠により還元して製造していたが、現在ではベンゼンとプロピレンからジイソプロピルベンゼン法により製造している。この方式方法では、ヒドロキノンとレゾルシン（m(メタ)-ジヒドロキシベンゼン）の両方ができる（図）。無色の針状結晶。熱水、エタノール（エチルアルコール）、エーテルなどにはよく溶けるが、生水には100ミリリットルに対して5.8グラムしか溶けない。還元性をもち、とくにアルカリ性水稀硫酸は還元性が強い。写真照片現像剤、过酸尽量不要剤としての好处をもつ。医薬部外品であり、クリーム・軟膏(なんこう)として使われているが、発癌(はつがん)性が疑われていて、2％之上の高濃度の共同参与は制限されている。［廣田 穰 20二零一五年六月21日］
用处
電球、軽合金のメッキ
用处
写真現像薬、ゴム酸化避免剤、染料等の中間分解质料
用处
写真用、有機分解质料、重合避免剤。
用处
白黒写真現像液の资料。
用处
写真用、阐发用還元剤。
化粧品の成份用处
還元剤、毛髪着色剤、皮膚ブリーチ剤、酸化避免剤、香料
効能
皮膚漂白感化, チロシナーゼ阻害薬
利用上の注重
空気中で次序递次に着色する。
説明
Hydroquinone (HQ) is produced by the oxidation of aniline or
phenol, by the reduction of quinone, or from a reaction of
acetylene and carbon monoxide. Hydroquinone occurs naturally
as a glucose ether, also known as arbutin, in the leaves of
many plants and in fruits, as well as one of the agents used in the
defense mechanism of the bombardier beetle, family Carabidae.
化学的特征
Hydroquinone, a colorless, hexagonal prism, has been reported to be a good antimitotic
and tumor-inhibiting agent. It is a reducing agent used in a photographic developer,
which polymerizes in the presence of oxidizing agents. In the manufacturing industry
it may occur include bacteriostatic agent, drug, fur processing, motor fuel, paint, organic
chemicals, plastics, stone coating, and styrene monomers.
物理的性質
Colorless to pale brown, odorless, hexagonal crystals
利用
hydroquinone is a pigment-lightening agent used in bleaching creams. Hydroquinone combines with oxygen very rapidly and becomes brown when exposed to air. Although it occurs naturally, the synthetic version is the one commonly used in cosmetics. Application to the skin may cause allergic reaction and increase skin sun sensitivity. Hydroquinone is potentially carcinogenic and is associated with causing ochronosis, a discoloration of the skin. The u.S. FDA has banned hydroquinone from oTC cosmetic formulations, but allows 4 percent in prescription products. Its use in cosmetics is prohibited in some european countries and in Australia.
定義
ChEBI: A benzenediol comprising benzene core carrying two hydroxy substituents para to each other.
適応症
Hydroquinone interferes with the production of the
pigment melanin by epidermal melanocytes through at
least two mechanisms: it competitively inhibits tyrosinase,
one of the principal enzymes responsible for converting
tyrosine to melanin, and it selectively damages
melanocytes and melanosomes (the organelles within
which melanin is stored).
調製方式
There are three current manufacturing processes for HQ:
oxidative cleavage of diisopropylbenzene, oxidation of aniline,
and hydroxylation of phenol.
Diisopropylbenzene is air oxidized to the intermediate
diisopropylbenzene bishydroperoxide. This hydroperoxide
is purified by extraction and reacted further to form
hydroquinone. The purified product is isolated by filtration
and packaged. The process can be almost entirely closed,
continuous, computer-controlled, and monitored.
HQcan also be prepared by oxidizing aniline to quinone in
the presence of manganese dioxide and sulfuric acid.
p-Benzoquinone is then reduced to HQ using iron oxide.
The resulting hydroquinone is crystallized and dried.
The process occurs in a closed system.
HQis also manufactured by hydroxylation of phenol using
hydrogen peroxide as a hydroxylation agent. The reaction is
catalyzed by strong mineral acids or ferrous or cobalt salts.
天下保健機関（WHO）
Hydroquinone was introduced in 1965 as a topical depigmenting
agent for hyperpigmentation. At high concentrations hydroquinone is corrosive
and in most countries has been restricted to the level of approximately 2% and
limited to the period of less than 2 months. Additional consideration for restrictive
action is that animal experiments have also demonstrated carcinogenic and
mutagenic potential of hydroquinone.
普通的な説明
Light colored crystals or solutions. May irritate the skin, eyes and mucous membranes. Mildly toxic by ingestion or skin absorption.
空気と水の反応
Darkens on exposure to air and light. Miscible in water. Solutions become brown in air due to oxidation. Oxidation is very rapid in the presence of alkali.
反応プロフィール
Hydroquinone is a slight explosion hazard when exposed to heat. Incompatible with strong oxidizing agents. Also incompatible with bases. Hydroquinone reacts with oxygen and sodium hydroxide. Reacts with ferric salts . Hot and/or concentrated NaOH can cause Hydroquinone to decompose exothermically at elevated temperature. (NFPA Pub. 491M, 1975, 385)
危険性
Toxic by ingestion and inhalation, irritant.
Questionable carcinogen.
安康ハザード
Hydroquinone is very toxic; the probable oral lethal dose for humans is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150 lb. person. It is irritating but not corrosive. Fatal human doses have ranged from 5-12 grams, but 300-500 mg have been ingested daily for 3-5 months without ill effects. Death is apparently initiated by respiratory failure or anoxia.
火災危険
Dust cloud may explode if ignited in an enclosed area. Hydroquinone can react with oxidizing materials and is rapidly oxidized in the presence of alkaline materials. Oxidizes in air.
打仗アレルゲン
Hydroquinone is used in photography developers (black
and white, X-ray, and microfilms), in plastics, in hair
dyes as an antioxidant and hair colorant. Hydroquinone
is found in many skin bleaching creams.
臨床応用
Hydroquinone is applied topically to treat disorders
characterized by excessive melanin in the epidermis,
such as melasma. In the United States, nonprescription
skin-lightening products contain hydroquinone at concentrations
of 2% or less; higher concentrations are
available by prescription.
副感化
The incidence of adverse effects with hydroquinone
increases in proportion to its concentration. A relatively
common side effect is local irritation, which may actually
exacerbate the discoloration of the skin being
treated. Allergic contact dermatitis occurs less commonly.
A rare but more serious complication is exogenous
ochronosis, in which a yellow-brown pigment deposited
in the dermis results in blue-black pigmentation
of the skin that may be permanent.
発がん性
No case reports of cancer associated
with HQ exposure have been published.
純化方式
Crystallise quinol from acetone, *benzene, EtOH, EtOH/*benzene, water or acetonitrile (25g in 30mL), preferably under nitrogen. Dry it under vacuum. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 6 H 836, 6 IV 5712.]
ヒドロキノン 下贱と下贱の製品情報
原资料
準備製品
抱水クロラール
tert-ブチルヒドロキノン
4-クロロ-2,5-ジメトキシアニリン
3,3-ジメチル-4-ペンテン酸エチル
フルアジホップ-P-ブチル標準品
アクリル酸ヒドロキシプロピル (2-ヒドロキシプロピルエステル, 2-ヒドロキシ-1-メチルエチルエステル夹杂物)
1-(2,5-Dimethoxyphenyl)-2-oximino-1-propanone
7-HYDROXYISOFLAVONE
4-クロロ-8-(トリフルオロメチル)キノリン
ｔ－ブチルヒドロキシアニソール
α-シアノアクリル酸ブチル
2-AMINO-1-(2,5-DIMETHOXYPHENYL)-1-PROPANONE
ピレノキシン
2-ジシクロヘキシルホスフィノ-2',4',6'-トリイソプロピルビフェニル
3-メチルスルホレン
2,6-ジクロロ-4-ニトロ-4'-[2-シアノエチル(2-アセトキシエチル)アミノ]アゾベンゼン
ammonium manganous sulfate
1,2,4-トリメトキシベンゼン
クロロ(1,5-シクロオクタジエン)イリジウム(I) (ダイマー)
3-スルホレン
フルアジホップ-ブチル
メタクリル酸2-ヒドロキシエチル
2,2-ジメチル-3-(2-メチル-1-プロペニル)シクロプロパン-1-カルボン酸メチル
アクリル酸ノニル
アゾイックジアゾコンポーネント20 (ベース)
2,3-ジメチル-1,3-ブタジエン
ゲンチシン酸
4-[(6-クロロ-2-ベンゾオキサゾリル)オキシ]フェノール
4-フェノキシフェノール
1,4-ジメトキシベンゼン
1,4-ジアセトキシベンゼン
2-CHLOROPYRIMIDINE-4-CARBONITRILE
2,5-ジメトキシアニリン
2,5-ジ-tert-ブチルヒドロキノン
2,2-ジメチル-3-(2-メチル-1-プロペニル)シクロプロパン カルボン酸 エチル
キザロホップ-P-エチル標準品
1,2-ナフタル酸無水物
ヘキサン酸アリル
(1,1-DIMETHYL-PROP-2-YNYL)-HYDRAZINE
酢酸4-ビニルフェニル