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16-September-2008 16:15:14 - Acetone For other uses, see Acetone disambiguation. Acetone1 Ball-and-stick model of acetone Space-filling model of acetone IUPAC name Propanone Other names β-ketopropane Dimethyl ketone, DMK Identifiers CAS number 67-64-1 RTECS number AL31500000 SMILES CC=OC InChI 1/C3H6O/c1-324/h1-2H3 Properties Molecular formula CH3COCH3 Molar mass 58.08 g/mol Appearance Colorless liquid Density 0.79 g/cm³, liquid Melting point -94.9 °C 178.2 K Boiling point 56.53 °C 329.4 K Solubility in water miscible Viscosity 0.32 cP at 20 °C Structure Molecular shape trigonal planar at C=O Dipole moment 2.91 D Hazards MSDS External MSDS EU classification Flammable F Irritant Xi NFPA 704 3 1 0 R-phrases R11, R36, R66, R67 S-phrases S2, S9, S16, S26 Flash point -18 °C Autoignition temperature 465 °C Related compounds Related solvents Water Ethanol Isopropanol Toluene Supplementary data page Structure and properties n, εr, etc. Thermodynamic data Phase behaviour Solid, liquid, gas Spectral data UV, IR, NMR, MS Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Acetone also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane is a colorless, mobile, flammable liquid. It is the simplest example of the ketones. Acetone is miscible with water, ethanol, ether, etc., and itself serves as an important solvent. The most familiar household uses of acetone are as the active ingredient in nail polish remover and paint thinner. Acetone is also used to make plastic, fibers, drugs, and other chemicals. In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body. Contents 1 Production 2 Biosynthesis 3 Uses 3.1 Cleaning fluid 3.2 Solvent 3.3 Feedstock 3.4 Automotive fuel additive 3.5 Other uses 4 Safety 4.1 Flammability 4.2 Toxicity 4.3 Acetone peroxide 4.4 Toxicology 4.5 Environmental Effects 5 References 6 External links Production Acetone is produced primarily in the cumene process. Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate. During World War I a new process of producing acetone through bacterial fermentation was developed by Chaim Weizmann, later the first president of Israel, in order to help the British war effort. This Acetone Butanol Ethanol process was abandoned due to the small yield of Acetone Butanol compared to the organic waste. Biosynthesis See also: ketosis Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Uses Cleaning fluid Acetone is often the primary or only component in nail polish remover. Ethyl acetate, another organic solvent, is sometimes used as well. Acetone is also used as a superglue remover. It can be used for thinning and cleaning fiberglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres. It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part epoxies and superglue before hardening. A heavy-duty degreaser, it is useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives. It easily removes residues from glass and porcelain. In biological research contexts, buffers that contain acetone such as citrate-buffered formalin use the acetone to lyse cells for further experimentation. Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers. Solvent Acetone can also dissolve many plastics, including those used in Nalgene bottles made of polystyrene, polycarbonate and some types of polypropylene.2 In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN2 reactions. The use of acetone solvent is also critical for the successful Jones oxidation. Technical grade acetone is inexpensive. Because of acetone's medium polarity, it dissolves a wide range of compounds. Thus, it is commonly loaded into squeeze bottles and used as a general solvent in rinsing laboratory glassware. Though flammable itself, acetone is also used extensively for the safe transporting and storing of acetylene in the mining industry. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene. 3 4. Feedstock An important industrial use for acetone involves its reaction with phenol for the manufacture of bisphenol A. Bisphenol A is an important component of many polymers such as polycarbonates, polyurethanes and epoxy resins. Acetone has also been used in the manufacture of cordite. Automotive fuel additive Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of dramatic improvement in fuel economy and engine life.5 This practice is controversial as the body of systematic testing shows that acetone has no measurable effect or may in fact reduce engine life by adversely affecting fuel system parts.678 Debates on this subject and the perrenial claims of a Big Oil cover-up intensified when the practice was addressed on the popular American TV show MythBusters in 2006, and shown to have negative effect in the televised fuel economy test.9. Other uses Acetone is also used as a drying agent, due to the readiness with which it mixes with water, and its volatility. It can be used as an artistic agent; when rubbed on the back of a laser print or photocopy placed face-down on another surface and burnished firmly, the toner of the image is allowed to transfer to the destination surface. Acetone can be cooled with dry ice to -78C without freezing. This fact has caused acetone/dry ice baths to be used as organic solvents for reactions that must be carried out at low temperatures. Acetone is fluorescent under ultraviolet light, and acetone vapor may be used as a fluorescent tracer in fluid flow experiments. 10 Safety Flammability The most common hazard associated with acetone is its extreme flammability. It auto ignites at a temperature of 465C 869F. At temperatures greater than acetone's flash point of -20C -4F, air mixtures of between 2.5% and 12.8% acetone, by volume, may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition source and flash back. Static discharge may also ignite acetone fires. 11 Toxicity Acetone may be harmful by inhalation, ingestion, or skin absorption, but fatalities only occur with larger quantities: LD50 ingested by humans: 1.159 g/kg LD50 inhalation by mice: 44g per cubic meter, over 4 hours. 12 Acetone peroxide Main article: acetone peroxide When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into waste solvent containing acetone. Acetone peroxide is more than ten times as friction and shock sensitive as nitroglycerin. Due to its instability, it is rarely used, despite its easy chemical synthesis. Toxicology June 2008 Acetone is an irritant and inhalation may lead to hepatotoxic effects causing liver damage.citation needed The vapors should be avoided. In no circumstance should it be consumed directly or indirectly.citation needed Always use goggles when handling acetone; it can cause permanent eye damage corneal clouding.citation needed Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production see ketosis. Acetone can be elevated in diabetes. Contamination of water, food e.g. milk, or the air acetone is volatile can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone is not a very toxic compound; it can, however, damage the mucosa of the mouth and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death.citation needed The effects of long-term exposure to acetone are known mostly from animal studies. Kidney, liver, and nerve damage, increased birth defects, and lowered reproduction ability of males only occurred in animals exposed long-term. It is not known if these same effects would be exhibited in humans. Pregnant women should avoid contact with acetone and acetone fumes in order to avoid the possibility of birth defects, including brain damage.citation needed Interestingly, acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.13 It has been hypothesized that the high fat low carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.13 Environmental Effects Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it is degraded by UV light with a 22-day half-life. Acetone does not build up in soil, animals, or waterways since it is consumed by microorganisms. 14 LD50 in fish is 8.3g/l of water or about 0.8% over 96 hours. Environmental half-life is about 1 to 10 days. But acetone may pose a significant risk of oxygen depletion in aquatic systems due to the microbial activity consuming it. 15. CERCLA requires reporting a spill of 5000 lbs or more. References ^ Merck Index, 11th ion, 58. ^ NALGENE Labware - Technical Data ^ Mine Safety and Health Administration MSHA - Safety Hazard Information - Special Hazards of Acetylene ^ History - Acetylene dissolved in acetone ^ Louis LaPonte 2007-02-13. Acetone in Fuels A Study of Dimethylketone or Propanone. Smartgas.net. Retrieved on 2007-06-06. ^ Acetone as a Fuel Additive. Pure Energy Systems Wiki. Retrieved on 2007-06-06. ^ Tom and Ray Magliozzi 2006-01-21. Click and Clack Talk Cars. Independent Record. Retrieved on 2007-06-06. ^ Can adding Acetone to fuel increase mpg by 15 to 35%?. Snopes.com Message Board. Retrieved on 2007-06-06. ^ MythBusters Season 4, Episode 53 ^ Lozano, Yip, and Hanson, Acetone: a tracer for concentration measurements in gaseous flows by planar laser-induced fluorescence, Exp. Fluids 13, pp. 369, 1992. ^ Acetone ^ Safety MSDS data for propanone ^ a b Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC 3rd, Burnham WM 2003. Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet. Ann Neurol. 54 2: 219-226. doi:10.1002/ana.10634. ^ tf21 ^ http://www.jmloveridge.com/cosh/Acetone.pdf External links International Chemical Safety Card 0087 National Pollutant Inventory - Acetone MSDS sheet for Acetone NIOSH Pocket Guide to Chemical Hazards Retrieved from http://en..org/wiki/Acetone Categories: Household chemicals | Cosmetic chemicals | Biotechnology products | Ketones | Ketone solvents | Fuel additives | DEA List II chemicalsHidden categories: Articles needing additional references from June 2008 | All articles with statements | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Bosanski ÄŒesky Dansk Deutsch Eesti Ελληνικά Español Esperanto Ù?ارسی Français Galego í•œêµì–´ Hrvatski Italiano עברית Latina LatvieÅ¡u Lietuvių Magyar Nederlands ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português Română РуÑ?Ñ?кий Shqip SlovenÄ?ina SlovenÅ¡Ä?ina Suomi Svenska ไทย Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 14 August 2008, at 03:02
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