アセトン 化学特性,用途語,生産方法
外観
無色澄明の液体
定義
本品は、次の化学式で表される脂肪族ケトンである。
溶解性
水及びエタノールに極めて溶けやすい。
解説
アセトン，ジメチルケトン(dimethyl ketone)ともいう．かつては炭水化物のアセトン-ブタノール発酵，イソプロピルアルコールの脱水素などで製造されたが，現在ではヘキスト-ワッカー法により，プロペンを塩化パラジウム(Ⅱ)と塩化銅(Ⅱ)の水溶液を触媒として，空気または酸素で部分酸化して合成される．また，クメン法によるフェノールの合成において副生し，工業製品としてはこのクメン法によるものが大部分を占める．エーテル臭をもつ無色の液体．融点－94.6 ℃，沸点56.5 ℃．d4200.7898．nD201.3591．水，エタノール，エーテルなどに易溶．高温で熱分解するとケテンとメタンが生成する．工業的にアセチルセルロース，ニトロセルロース，アセチレンなどの溶剤として大量に使用され，そのほか，有機溶剤として多方面の用途がある．また，メタクリル酸エステルの合成原料として重要で，ケテンを経て無水酢酸の製造にも利用される．
用途
精密分析、超高純度溶剤としての個人専用試薬。
用途
汎用試薬、高純度を要する低沸点溶剤等。
用途
高速液体クロマトグラフィーの溶離液及び溶離液の調製。
用途
生体試料中等のダイオキシン類の分析における溶媒。
用途
吸光分析(紫外)、蛍光分析用溶媒。
用途
工業用の溶剤、化学物質原料(ビスフェノールA,MMA,MIBK等)、化粧品類添加剤
用途
薄層クロマトグラフィー、ペーパークロマトグラフィーの展開溶媒。
用途
汎用試薬、低沸点溶剤、有機合成原料。
用途
環境ホルモンの分析に使用します。
化粧品の成分用途
変性剤、溶剤、香料
効能
溶解剤
主な用途／役割
- アセトンは、最も簡単な構造のケトンであり、その構造ゆえ、幅広い有機化合物をよく溶かし、室温で揮発性が高く乾きやすいため、各種用途に溶媒として使用されている。塗料、接着剤、化粧品等、各種用途に溶剤として用いられる他、エポキシ樹脂の原料であるビスフェノールAやメタクリル酸メチルの原料として使用される。
- 溶剤型接着剤、水性型エマルション系接着剤、エアゾール接着剤に使用される。
使用上の注意
不活性ガス封入
説明
Acetone is a flammable, colorless liquid with a pleasant odor. It is used widely as an organic
solvent and in the chemical industry. It is the simplest ketone, which also goes by the name
dimethyl ketone (DMK). Acetone was originally referred to as pyroacetic spirit because it was
obtained from the destructive distillation of acetates and acetic acid.
化学的特性
Acetone, CH3COCH3, also known as 2-propanone and dimethylketone, is a colorless, volatile,flammable liquid that boils at 56°C (133 OF). It is misciblewith water and is oftenused as a solventin the manufacture of lacquers and paints.
物理的性質
Clear, colorless, liquid with a sweet, fragrant odor. Sweetish taste. Odor threshold concentrations
ranged from 42 ppm
v (Nagata and Takeuchi, 1990) to 100 ppm
v (Leonardos et al., 1969).
Experimentally determined detection and recognition odor threshold concentrations were 48
mg/m
3 (20 ppm
v) and 78 mg/m
3 (33 ppm
v), respectively (Hellman and Small, 1974).
天然物の起源
Reported found in apple, pear, grape, pineapple, strawberry, raspberry, tomato, black currant, citrus, onion and
potato; also reported found in cocoa leaves, in Mexican goosefoot and in the oils of coriander and lavender. In trace amounts it has
been reportedly identified in the oil of bitter orange, in distilled wine and in coffee aroma
来歴
The traditional method of producing acetone in the 19th century and the beginning of the 20th century was to distill acetates, particularly calcium acetate, Ca(C
2H
3O
2)
2.
Weizmann discovered a process to produce butyl alcohol and acetone from the bacterium Clostridium acetobutylicum in 1914. With England’s urgent demand for acetone, Winston Churchill (1874–1965) enlisted Weizmann to develop the Weizmann process for acetone production on an industrial scale. Fermentation and distillation techniques for acetone production were replaced starting in the 1950s with the cumene oxidation process . In this process, cumene is oxidized to cumene hydroperoxide, which is then decomposed using acid to acetone and phenol. This is the primary method used to produce phenol, and acetone is produced as a co-product in the process, with a yield of about 0.6:1 of acetone to phenol.
使用
Acetone′s luminesence intensity is dependent upon the solution components 1. The absorption of UV light by acetone, results in its photolysis and the production of radials 1.
調製方法
Acetone is obtained by fermentation as a by-product of n-butyl
alcohol manufacture, or by chemical synthesis from isopropyl
alcohol; from cumene as a by-product in phenol manufacture; or
from propane as a by-product of oxidation-cracking.
定義
ChEBI: A methyl ketone that consists of propane bearing an oxo group at C2.
一般的な説明
A clear colorless liquid with a sweetish odor. Flash point 0°F. Less dense than water. Vapors are heavier than air. Used as a solvent in paint and nail polish removers.
空気と水の反応
Highly flammable. Water soluble.
反応プロフィール
Acetone was reported that a mixture of Acetone and chloroform, in a residue bottle, exploded. Since addition of Acetone to chloroform in the presence of base will result in a highly exothermic reaction, Acetone is thought that a base was in the bottle [MCA Case History 1661. 1970]. Also, Nitrosyl chloride, sealed in a tube with a residue of Acetone in the presence of platinum catalyst, gave an explosive reaction [Chem. Eng. News 35(43):60. 1967]. The reaction of nitrosyl perchlorate and Acetone ignites and explodes. Explosions occur with mixtures of nitrosyl perchlorate and primary amine [Ann. Chem. 42:2031. 1909]. Reacts violently with nitric acid. Also causes exothermic reaction when in contact with aldehydes.
健康ハザード
The acute toxicity of acetone is low. Acetone is primarily a central nervous system depressant at high concentrations (greater than 12,000 ppm). Unacclimated volunteers exposed to 500 ppm acetone experienced eye and nasal irritation, but it has been reported that 1000 ppm for an 8-hour day produced no effects other than slight transient irritation to eyes, nose, and throat. Therefore there are good warning properties for those unaccustomed to working with acetone; however, frequent use of acetone seems to cause accommodation to its slight irritating properties. Acetone is practically nontoxic by ingestion. A case of a man swallowing 200 mL of acetone resulted in his becoming stuporous after 1 hour and then comatose; he regained consciousness 12 hour later. Acetone is slightly irritating to the skin, and prolonged contact may cause dermatitis. Liquid acetone produces moderate transient eye irritation. Acetone has not been found to be carcinogenic in animal tests or to have effects on reproduction or fertility.
火災危険
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
燃焼性と爆発性
Acetone is extremely flammable (NFPA rating = 3), and its vapor can travel a
considerable distance to an ignition source and "flash back." Acetone vapor forms
explosive mixtures with air at concentrations of 2 to 13% (by volume). Carbon
dioxide or dry chemical extinguishers should be used for acetone fires.
応用例（製薬）
Acetone is used as a solvent or cosolvent in topical preparations,
and as an aid in wet granulation.It has also been used when
formulating tablets with water-sensitive active ingredients, or to
solvate poorly water-soluble binders in a wet granulation process.
Acetone has also been used in the formulation of microspheres to
enhance drug release.Owing to its low boiling point, acetone has
been used to extract thermolabile substances from crude drugs.
工業用途
Acetone is valuable solvent component in
acrylic/nitrocellulose automotive lacquers. Acetone is the solvent of choice in film
coatings operations which use vinylidene chloride-acrylonitrile copolymer
formulations.Other ketones that may be used in these film coating operations include methyl isobutyl ketone, ethyl n-amyl ketone, and diisobutyl ketone.Acetone, blends of MIBK and MEK, methyl namyl
ketone, ethyl n-amyl ketone, and diisobutyl ketone are all useful solvents
for vinyl resin copolymers. The presence of one of the slower evaporating
ketones in the solvent blend prevents quick drying, improves flow, and gives
blush resistance to the coating. Acetone is also used as a resin thinner in polyester
resins and as a clean up solvent for the resin reactor kettle.In solvents industry, Acetone is a component of solvent blends in
urethane, nitrile rubber, and neoprene industrial adhesives.Acetone is the
primary solvent in resin-type adhesives and pressure sensitive chlorinated rubber
adhesives. Acetone also can be used to extract fats, oils, waxes, and resins from
natural products, to dewax lubricating oils, and to extract certain essential oils.Acetone is also an important chemical intermediate in the
preparation of several oxygenated solvents including the ketones, diacetone alcohol,
mesityl oxide, methyl isobutyl ketone, and isophorone.
安全性
Acetone is considered moderately toxic, and is a skin irritant and
severe eye irritant. Skin irritation has been reported due to its
defatting action, and prolonged inhalation may result in headaches.
Inhalation of acetone can produce systemic effects such as
conjunctival irritation, respiratory system effects, nausea, and
vomiting.
LD
50 (mouse, oral): 3.0 g/kg
LD
50 (mouse, IP): 1.297 g/kg
LD
50 (rabbit, oral): 5.340 g/kg
LD
50 (rabbit, skin): 0.2 g/kg
LD
50 (rat, IV): 5.5 g/kg
LD
50 (rat, oral): 5.8 g/kg
職業ばく露
It is used as a solvent in nail polish remover and many other chemicals. Used in the production of lubricating oils and as an intermediate in the manufacture of chloroform and of various pharmaceuticals and pesticides.
発がん性
Acetone may be weakly genotoxic, but the
majority of assays were negative.7 It was not
tumorigenic in skin painting studies in mice.
The 2003 ACGIH threshold limit valuetime-
weighted average (TLV-TWA) for
acetone is 750ppm (1780mg/m3) with a
short-term excursion level of 1000ppm
(2380mg/m3).
環境運命予測
Biological. Following a lag time of 20 to 25 h, acetone degraded in activated sludge (30 mg/L)
at a rate constant ranging from 0.016 to 0.020/h (Urano and Kato, 1986). Soil bacteria can mineralize acetone to carbon dioxide (Taylor et al., 1980). Bridié et al. (1979) reported BOD and
COD values of 1.85 and 1.92 g/g using filtered effluent from a biological sanitary waste treatment
plant. These values were determined using a standard dilution method at 20 °C for a period of 5 d.
Similarly, Heukelekian and Rand (1955) reported a 5-d BOD value of 0.85 g/g which is 38.5% of
the ThOD value of 2.52 g/g. Waggy et al. (1994) reported 5, 15, and 28-d BOD values of 14, 74,
and 74%, respectively. Using the BOD technique to measure biodegradation, the mean 5-d BOD
value (mM BOD/mM acetone) and ThOD were 1.52 and 38.0%, respectively (Vaishnav et al.,
1987).
Photolytic. Photolysis of acetone in air yields carbon monoxide and free radicals, but in
isopropanol, pinacol is formed (Calvert and Pitts, 1966). Photolysis of acetone vapor with nitrogen
dioxide via a mercury lamp gave peroxyacetyl nitrate as the major product with smaller quantities
of methyl nitrate (Warneck and Zerbach, 1992).
Chemical/Physical. Hypochlorite ions, formed by the chlorination of water for disinfection
purposes, may react with acetone to form chloroform. This reaction is expected to be significant
within the pH range of 6 to 7 (Stevens et al., 1976).
貯蔵
Acetone should be
used only in areas free of ignition sources, and quantities greater than 1 liter should
be stored in tightly sealed metal containers in areas separate from oxidizers.
輸送方法
UN1090 Acetone, Hazard Class: 3; Labels: 3-Flammable liquid
不和合性
Acetone reacts violently with oxidizing agents, chlorinated solvents,
and alkali mixtures. It reacts vigorously with sulfur dichloride,
potassium t-butoxide, and hexachloromelamine. Acetone should
not be used as a solvent for iodine, as it forms a volatile compound
that is extremely irritating to the eyes.
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. Incineration.
規制状況(Regulatory Status)
Included in the FDA Inactive Ingredients Database (inhalation
solution; oral tablets; topical preparations). Included in the
Canadian List of Acceptable Non-medicinal Ingredients. Included
in nonparenteral medicines licensed in the UK.
アセトン 上流と下流の製品情報
原材料
準備製品
ピリジン-2-スルホン酸
カルコン
3-アミノピリダジン
オルシプレナリン
4-(フェニルメトキシ)ベンゼンエタノール
PROPIONAMIDINE
7-(2-オキソプロポキシ)-2H-クロメン-2-オン
9,10-ジヒドロ-9,9-ジメチルアクリジン
3-(-Hydroxyphenethyl)-2-imino thiazolidine
2-(4-(CHLOROMETHYL)THIAZOL-2-YL)GUANIDINE
1-Phenylethanone phenylhydrazone
7-メトキシクマリン
四硝酸ペンタエリスリトール
7-エトキシクマリン
2-ヨードアセトアミド
3,3',4,4'-ベンゾフェノンテトラカルボン酸二無水物
6-エトキシ-2,2,4-トリメチル-1,2-ジヒドロキノリン
4-(4-ヒドロキシフェニル)-3-ブテン-2-オン
(2-オキソプロピル)ホスホン酸ジメチル
1,1,3,3-テトラブロモアセトン
アミカシン 硫酸塩
トリヨードメタン
4-イソチオシアナト安息香酸
アミカシン硫酸塩
イソホロン
5-メトキシ-2-メチルインドール
3,4-ジヒドロ-2H-1,5-ベンゾジオキセピン-7-カルブアルデヒド
4-(2-THIENYL)BUT-3-EN-2-ONE
エピネフリン
H-GLU-LYS-OH
2,5-ジクロロ-3-チオフェンスルホンアミド
o-(モルホリノカルボニル)安息香酸
2-ブロモドデカン酸
2-フェニル-4-キノリンカルボン酸
3-メチル-1-ブチン-3-オール
3-(ジメチルアミノ)プロピオフェノン塩酸塩
1,3-ジビニルテトラメチルジシロキサン
3-メチル-2-チオフェンカルボン酸
methyl 3,4-dihydro-4-oxoquinazoline-7-carboxylate
7-(アリルオキシ)クマリン