Ацетон химические свойства, назначение, производство
Описание
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.
Химические свойства
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.
Физические свойства
Clear, colorless, liquid with a sweet, fragrant odor. Sweetish taste. Odor threshold concentrations
ranged from 42 ppmv (Nagata and Takeuchi, 1990) to 100 ppmv (Leonardos et al., 1969).
Experimentally determined detection and recognition odor threshold concentrations were 48
mg/m3 (20 ppmv) and 78 mg/m3 (33 ppmv), respectively (Hellman and Small, 1974).
Вхождение
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
История
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(C2H3O2)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.
Использование
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.
Определение
ChEBI: A methyl ketone that consists of propane bearing an oxo group at C2.
Методы производства
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.
Общее описание
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.
Реакции воздуха и воды
Highly flammable. Water soluble.
Профиль реактивности
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.
Угроза здоровью
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.
Пожароопасность
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.
Воспламеняемость и взрывоопасность
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.
Фармацевтические приложения
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.
Промышленное использование
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.
Безопасность
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.
LD50 (mouse, oral): 3.0 g/kg
LD50 (mouse, IP): 1.297 g/kg
LD50 (rabbit, oral): 5.340 g/kg
LD50 (rabbit, skin): 0.2 g/kg
LD50 (rat, IV): 5.5 g/kg
LD50 (rat, oral): 5.8 g/kg
Возможный контакт
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.
Канцерогенность
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).
Экологическая судьба
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).
хранилище
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.
Перевозки
UN1090 Acetone, Hazard Class: 3; Labels: 3-Flammable liquid
Несовместимости
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.
Утилизация отходов
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.
Регуляторный статус
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.
Ацетон препаратная продукция и сырье
сырьё
препарат
2-пиридинсульфоновая кислота
Халькон
3-аминопиридазин
Орципреналин
2 - (4-бензилоксифенил) этанол
PROPIONAMIDINE
CHEMBRDG-BB 6088138
9,9-диметилкарбазин
3-(-Гидроксифенетил)-2-иминотиазолидин
2- (4- (хлорметил) тиазол-2-ил) гуанидин
1-фенилэтанон фенилгидразон
7-Methoxycoumarin
Pentaerythritol tetranitrate
7-Ethoxycoumarin
2-йодацетамид
3,3',4,4'-бензофенонтетракарбоновый диангидрид
Ethoxyquin
4-Hydroxybenzylideneacetone
Диметил acetylmethylphosphonate
1,1,3,3-ТЕТРАБРОМОАЦЕТОН
Амикацин сульфатная соль
ЙОДОФОРМ
4-CARBOXYPHENYL ISOTHIOCYANATE
Амикацин дисульфата
Изофорон
5-метокси-2-метилиндол
3,4-дигидро-2H-1,5-бензодиoxэпиne-7-карбальдегид
4-(2-THIENYL)BUT-3-EN-2-ONE
L(-)-эфинифрин
H-GLU-LYS-OH
2,5-Dichlorothiophene-3-sulfonamide
2-(MORPHOLINE-4-CARBONYL)-BENZOIC ACID
2-BROMODODECANOIC ACID
CINCHOPHEN
2-Метил-3-бутин-2-ол
Гидрохлорид 3-Dimethylaminopropiophenone
Дивинилтетраметилдисилоксан
3-метилтиофен-2-карбоновой кислоты
methyl 3,4-dihydro-4-oxoquinazoline-7-carboxylate
7-ALLYLOXYCOUMARIN