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Acetone

Acetone Basic information
Introduction Uses Production Health Effects
Product Name:Acetone
Synonyms:ACETONE ALCOHOL;GRAMS DECOLORIZER;GRAM STAIN NO 3;(CH3)2CO;2-Propanon;ketone,dimethyl;ketonepropane;-Ketopropane
CAS:67-64-1
MF:C3H6O
MW:58.08
EINECS:200-662-2
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Mol File:67-64-1.mol
Acetone Structure
Acetone Chemical Properties
Melting point -94 °C(lit.)
Boiling point 56 °C760 mm Hg(lit.)
density 0.791 g/mL at 25 °C(lit.)
vapor density 2 (vs air)
vapor pressure 184 mm Hg ( 20 °C)
refractive index n20/D 1.359(lit.)
FEMA 3326 | ACETONE
Fp 1 °F
storage temp. Store at RT.
solubility Miscible with water and with ethanol (96 per cent).
pka19.3(at 25℃)
form Liquid
color Colorless, invisible vapor
Specific Gravity0.79 (25/25℃)
OdorCharacteristic pungent odor detectable at 33 to 700 ppm (mean = 130 ppm)
PH5-6 (395g/l, H2O, 20°C)
Relative polarity0.355
explosive limit2.6-12.8%(V)
Water Solubility soluble
Merck 14,66
BRN 63580
CAS DataBase Reference67-64-1(CAS DataBase Reference)
NIST Chemistry ReferenceAcetone(67-64-1)
EPA Substance Registry System2-Propanone(67-64-1)
Safety Information
Hazard Codes F,Xi,T
Risk Statements 11-36-66-67-39/23/24/25-23/24/25
Safety Statements 9-16-26-45-36/37-7
RIDADR UN 1090 3/PG 2
WGK Germany 3
RTECS AL3150000
3-10
Autoignition Temperature465 °C
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29141100
Hazardous Substances Data67-64-1(Hazardous Substances Data)
ToxicityLD50 in rats: 10.7 ml/kg orally (Smyth)
MSDS Information
ProviderLanguage
Acetone English
Acetone Usage And Synthesis
IntroductionAcetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the group of chemical compounds known as ketones. It is a colorless, volatile, flammable liquid.
Acetone is miscible with water and serves as an important laboratory solvent for cleaning purposes. Acetone is a highly effective solvent for many organic compounds such as Methanol, ethanol, ether, chloroform, pyridine, etc., and is the active ingredient in nail polish remover. It is also used to make various plastics, fibers, drugs, and other chemicals.
Acetone exists in nature in the Free State. In the plants, it mainly exists in essential oils, such as tea oil, rosin essential oil, citrus oil, etc.; human urine and blood and animal urine, marine animal tissue and body fluids contain a small amount of acetone.
Uses
  • An important organic raw material in the chemical, artificial fiber, medicine, paint, plastics, organic glass, cosmetics and other industries; an excellent organic solvent that dissolves many organic products such as resin, cellulose acetate, acetylene and so on.
  • An important raw material for the synthesis of ketene, acetic anhydride, iodoform, polyisoprene rubber, methacrylic acid, methyl ester, chloroform, and epoxy resins.
  • The acetone cyanohydrin obtained from the reaction of acetone with hydrocyanic acid is the raw material of methacrylic resin (perspex).
  • A raw material in the production of epoxy resin intermediate bisphenol A.
  • In pharmaceuticals, acetone is used as extractants for a variety of vitamins and hormones in addition to vitamin C, and dewaxing solvents for petroleum refining.
  • A raw material for nail polish remover in cosmetics
  • One of the raw materials for synthesizing pyrethroids in pesticide industry
  • Acetone is often used to wipe the black ink above the copper tube in the precision copper tube industry.
ProductionIn 1913, the United Kingdom developed a method for fermenting cereals to produce acetone and butanol. In 1920, the dehydrogenation of isopropanol (synthesized by hydration of propylene) appeared. From 1953 to 1955, the United States Hercules and the British Distilling Company jointly developed the cumene process method, thereafter, Japan, the United Kingdom, and the Netherlands also developed other methods. Now, Most of the worldwide industrial production of acetone (and phenol) is based on the cumene process, which uses benzene and propylene as raw materials, via cumene intermediates, then oxidized, hydrolyzed to produce acetone and co-produced phenol.

Acetone is mainly used as an organic solvent and methyl methacrylate (the main raw material for organic glass).In the United States and Western Europe, the two accounts for 70% of the total consumption. It is used for bisphenol A, accounting for 10% to 15%, and the others 15% % to 20%.
Health EffectsSummary: Acetone is mainly responsible for the inhibition and anesthesia of the central nervous system and exposure to high concentrations may cause liver, kidney, and pancreas impair to particular people. Because of its low toxicity, rapid metabolism and detoxification, acute poisoning under production conditions is rare. In case acute poisoning happens, symptoms of vomiting, shortness of breath, paralysis, and even coma can occur. After oral administration, burning sensation in the lips and throat may occur after hours of incubation, such as dry mouth, vomiting, drowsiness, acidity and ketosis, and even temporary disturbance of consciousness. The long-term damage of acetone to the human body is manifested as irritation to the eyes such as tearing, photophobia and infiltration of the corneal epithelium, as well as dizziness, burning sensation, throat irritation, and coughing.

Metabolism in the body: After being absorbed by the lungs, gastrointestinal tract, and skin, acetone is easily absorbed into the bloodstream due to its high water solubility and is rapidly distributed throughout the body. The excretion depends on the dose. When the dose is large, the main tract is mainly through the lungs and kidneys, and a very small amount is discharged through the skin. When the dose is small, most of them are oxidized into carbon dioxide. The biological half-life of acetone in blood is 5.3 h for rats, 11 h for dogs, and 3 h for humans. The metabolites of acetone in the human body are mostly a tricarboxylic acid cycle intermediate that is decomposed to acetoacetate and converted to glycogen.
Chemical PropertiesAcetone is a colorless volatile, flammable, transparent liquid, with a sweetish odor and pungent sweetish taste.
Chemical PropertiesAcetone, 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.
Chemical PropertiesAcetone is a highly flammable, colorless liquid with a sweet, mint-like odor
Usesacetone is a solvent considered to be non-comedogenic and occasionally used in skin toners. It is primarily used in nail polish remover. It could be drying and very irritating to the skin depending on the concentration and frequency of use.
UsesAcetone′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.
UsesSuitable for HPLC, spectrophotometry, environmental testing
UsesUsed in liquid chromotography; cleaning glassware; extraction of solid waste.
UsesSolvent for fats, oils, waxes, resins, rubber, plastics, lacquers, varnishes, rubber cements. manufacture of methyl isobutyl ketone, mesityl oxide, acetic acid (ketene process), diacetone alcohol, chloroform, iodoform, bromoform, explosives, aeroplane dopes, rayon, photographic films, isoprene; storing acetylene gas (takes up about 24 times its vol of the gas); extraction of various principles from animal and plant substances; in paint and varnish removers; purifying paraffin; hardening and dehydrating tissues. Pharmaceutic aid (solvent).
DefinitionChEBI: A methyl ketone that consists of propane bearing an oxo group at C2.
Production MethodsAcetone 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.
General DescriptionA 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.
Air & Water ReactionsHighly flammable. Water soluble.
Reactivity ProfileAcetone 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.
Health HazardINHALATION: vapor irritating to eyes and mucous membranes; acts as an anesthetic in very high concentrations. INGESTION: low order of toxicity but very irritating to mucous membranes. SKIN: prolonged excessive contact causes defatting of the skin, possibly leading to dermatitis.
Health HazardThe 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.
Fire HazardAcetone 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.
Fire HazardHIGHLY 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.
Pharmaceutical ApplicationsAcetone 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.
Safety ProfileModerately toxic by various routes. A skin and severe eye irritant. Human systemic effects by inhalation: changes in EEG, changes in carbohydrate metabolism, nasal effects, conjunctiva irritation, respiratory system effects, nausea and vomiting, and muscle weakness. Human systemic effects by ingestion: coma, kidney damage, and metabolic changes. Narcotic in high concentration. In industry, no injurious effects have been reported other than skin irritation resulting from its defatting action, or headache from prolonged inhalation. Experimental reproductive effects. A common air contaminant. Highly flammable liquid. Dangerous disaster hazard due to fire and explosion hazard; can react vigorously with oxidizing materials. Potentially explosive reaction with nitric acid + sulfuric acid, bromine trifluoride, nitrosyl chloride + platinum, nitrosyl perchlorate, chromyl chloride, thiotrithiazyl perchlorate, and (2,4,6-trichloro-l,3,5triazine + water). Reacts to form explosive peroxide products with 2-methyl-1,3butadiene, hydrogen peroxide, and peroxomonosulfuric acid. Ignites on contact with activated carbon, chromium trioxide, dioxygen difluoride + carbon dioxide, and potassium-tert-butoxide. Reacts violently with bromoform, chloroform + alkalies, bromine, and sulfur dichloride. Incompatible with CrO, (nitric + acetic acid), NOCl, nitryl perchlorate, permonosulfuric acid, NaOBr, (sulfuric acid + potassium dichromate), (tho-diglycol + hydrogen peroxide), trichloromelamine, air, HNO3, chloroform, and H2SO4. To fight fire, use Con, dry chemical, alcohol foam. Used in production of drugs of abuse
SafetyAcetone 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
Potential ExposureIt 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.
First aidIf this chemical gets into the eyes, remove any contact lenses at once, and irrigate immediately with large amounts of water for at least 15 minutes. If this chemical contacts the skin, quickly remove contaminated clothing, and wash with large amounts of soap immediately. If a person breathes in large amounts of this chemical, move the exposed person to fresh air at once, and perform (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
storageAcetone should be stored in a cool, dry, well-ventilated place out of direct sunlight.
storageAcetone 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.
ShippingUN1090 Acetone, Hazard Class: 3; Labels: 3-Flammable liquid
Purification MethodsThe commercial preparation of acetone by catalytic dehydrogenation of isopropyl alcohol gives relatively pure material. Analytical reagent quality generally contains less than 1% of organic impurities but may have up to about 1% of H2O. Dry acetone is appreciably hygroscopic. The main organic impurity in acetone is mesityl oxide, formed by aldol condensation. It can be dried with anhydrous CaSO4, K2CO3 or type 4A Linde molecular sieves, and then distilled. Silica gel and alumina, or mildly acidic or basic desiccants cause acetone to undergo the aldol condensation, so that its water content is increased by passage through these reagents. This also occurs to some extent when P2O5 or sodium amalgam is used. Anhydrous MgSO4 is an inefficient drying agent, and CaCl2 forms an addition compound. Drierite (anhydrous CaSO4) offers minimum acid and base catalysis for aldol formation and is the recommended drying agent for this solvent [Coetzee & Siao Inorg Chem 14 2 1987, Riddick & Bunger Organic Solvents Wiley-Interscience, N.Y., 3rd edn, 1970]. Acetone can be shaken with Drierite (25g/L) for several hours before it is decanted and distilled from fresh Drierite (10g/L) through an efficient column, maintaining atmospheric contact through a Drierite drying tube. The equilibrium water content is about 10-2M. Anhydrous Mg(ClO4)2 should not be used as drying agent because of the risk of EXPLOSION with acetone vapour. Organic impurities have been removed from acetone by adding 4g of AgNO3 in 30mL of water to 1L of acetone, followed by 10mL of M NaOH, shaking for 10minutes, filtering, drying with anhydrous CaSO4 and distilling [Werner Analyst (London) 58 335 1933]. Alternatively, successive small portions of KMnO4 have been added to acetone at reflux, until the violet colour persists, followed by drying and distilling. Refluxing with chromium trioxide (CrO3) has also been used. Methanol has been removed from acetone by azeotropic distillation (at 35o) with methyl bromide, and treatment with acetyl chloride. Small amounts of acetone can be purified as the NaI addition compound, by dissolving 100g of finely powdered NaI in 400g of boiling acetone, then cooling in ice and salt to -8o. Crystals of NaI.3Me2CO are filtered off and, on warming in a flask, acetone distils off readily. [This method is more convenient than the one using the bisulfite addition compound.] It has also been purified by gas chromatography on a 20% free fatty acid phthalate (on Chromosorb P) column at 100o. For efficiency of desiccants in drying acetone see Burfield and Smithers [J Org Chem 43 3966 1978]. The water content of acetone can be determined by a modified Karl Fischer titration [Koupparis & Malmstadt Anal Chem 54 1914 1982]. [Beilstein 1 IV 3180.] Rapid procedure: Dry over anhydrous CaSO4 and distil.
IncompatibilitiesMay explode when mixed with chloroform, chromic anhydride. Incompatible with acids, bases, and oxidizing materials, such as peroxides, chlorates, perchlorates, nitrates, and permanganates. Unstable peroxides formed with strong oxidizers. May accumulate static electrical charges and may cause ignition of its vapors. Dissolves most rubber, resins, and plastics.
Flammability and ExplosibilityAcetone 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.
IncompatibilitiesAcetone 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.
Waste DisposalConsult 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.
Regulatory StatusIncluded 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.
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