| Acetone[1] | |
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| IUPAC name | Propanone |
| Other names | β-ketopropane Dimethyl ketone, |
| Identifiers | |
| CAS number | [67-64-1] |
| RTECS number | AL31500000 |
| SMILES | CC(=O)C |
| InChI | 1/C3H6O/c1-3(2)4/h1-2H3 |
| Properties | |
| Molecular formula | CH3COCH3 |
| Molar mass | 58. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 08 g/mol |
| Appearance | Colorless liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 79 g/cm³, liquid |
| Melting point |
−94. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 9 °C (178. 2 K) |
| Boiling point |
56. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 53 °C (329. 4 K) |
| Solubility in water | miscible |
| Viscosity | 0. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Miscibility is a term commonly used in Chemistry that refers to the property of Liquids to mix in all proportions forming a Homogeneous Solution Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 32 cP at 20 °C |
| Structure | |
| Molecular shape | trigonal planar at C=O |
| Dipole moment | 2. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 91 D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable (F) Irritant (Xi) |
| NFPA 704 |
 3
1
0
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| 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. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance and save the page -->This page provides supplementary chemical data on Acetone. Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling Flammability is the ease with which a substance will ignite causing Fire or Combustion. Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Isopropyl alcohol (also isopropanol, iso, isopro, Rubbing alcohol, or the abbreviation IPA) is a common name for Toluene, also known as methylbenzene or phenylmethane, is a clear water -insoluble liquid with the typical smell of Paint thinners redolent of and save the page -->This page provides supplementary chemical data on Acetone. and save the page -->This page provides supplementary chemical data on Acetone. The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test |
| 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 disclaimer and references |
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Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless, mobile, flammable liquid. and save the page -->This page provides supplementary chemical data on Acetone. and save the page -->This page provides supplementary chemical data on Acetone. Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly It is the simplest example of the ketones. A ketone (pronounced as key tone) is either the Functional group characterized by a Carbonyl group (O=C linked to two other Carbon atoms or Acetone is miscible with water, ethanol, ether, etc. Miscibility is a term commonly used in Chemistry that refers to the property of Liquids to mix in all proportions forming a Homogeneous Solution Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a , and itself serves as an important solvent. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. The most familiar household use of acetone is as the active ingredient in nail polish remover and paint thinner. Nail polish or nail varnish is a Lacquer that is applied to the nails of both the Fingers and Toes usually cosmetically but also as A paint thinner is a Solvent used to thin oil-based paints or as a cleaning agent Acetone is also used to make plastic, fibers, drugs, and other chemicals. Plastic is the general common term for a wide range of synthetic or semisynthetic organic solid materials suitable for the manufacture of industrial products 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 |
Production
Acetone is produced primarily in the cumene process. Cumene process is an Industrial process for developing Phenol and Acetone from Benzene and Propylene. Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate. Dry distillation is the Heating of Solid materials to produce Liquid or Gaseous products (which may condense into solids An acetate, or ethanoate, is either a salt or Ester of Acetic acid. The Chemical compound calcium acetate is the Calcium salt of Acetic acid. 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. World War I (abbreviated WWI; also known as the First World War, the Great War, and the War to End All The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Fermentation is the process of deriving energy from the oxidation of organic compounds such as carbohydrates using an endogenous electron acceptor which is Chaim Azriel Weizmann ( Hebrew: חיים עזריאל ויצמן – November 27, 1874 &ndash November 9, 1952) was a Zionist For a topic outline on this subject see List of basic Israel topics. This Acetone Butanol Ethanol process was abandoned due to the small yield of Acetone Butanol compared to the organic waste. Clostridium acetobutylicum, included in the genus Clostridium, is a commercially valuable Bacterium. Butanol or butyl alcohol (sometimes also called biobutanol when produced biologically is a Primary alcohol with a 4 Carbon structure and the Molecular
Biosynthesis
- See also: ketosis
Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Ketosis (kiːˈtoʊsɪs is a state in Metabolism occurring when the Liver excessively converts fat into fatty acids and Ketone Decarboxylation is any Chemical reaction in which a Carboxyl group (-COOH is split off from a compound as Carbon dioxide (CO2 Ketone bodies are three water-soluble compounds that are produced as by-products when Fatty acids are broken down for energy in the Liver and
Uses
Cleaning fluid
Acetone is often the primary (or only) component in nail polish remover. Nail polish or nail varnish is a Lacquer that is applied to the nails of both the Fingers and Toes usually cosmetically but also as Ethyl acetate, another organic solvent, is sometimes used as well. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Acetone is also used as a superglue remover. Cyanoacrylate is the generic name for cyanoacrylate based fast-acting Glues such as ethyl-2-cyanoacrylate (commonly sold under trade names like Superglue and Krazy 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. In Chemistry, epoxy or polyepoxide is a Thermosetting Epoxide Polymer that cures (polymerizes and crosslinks when mixed with a Cyanoacrylate is the generic name for cyanoacrylate based fast-acting Glues such as ethyl-2-cyanoacrylate (commonly sold under trade names like Superglue and Krazy 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. Lysis ( Greek, lysis from lyein = to separate refers to the death of a cell by breaking of the cellular membrane often by viral or osmotic
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. Nalgene (sometimes referred to as Nalge Nunc International) is a distributor and manufacturer of Plastic laboratory containers that has diversified into the field [2]
In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN2 reactions. "Polar molecule" and "Non-polar" redirect here In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen Organic reactions are Chemical reactions involving Organic compounds The basic Organic chemistry reaction types are Addition reactions Elimination The SN2 reaction (also known as bimolecular nucleophilic substitution) is a type of Nucleophilic substitution, where a lone pair from a Nucleophile The use of acetone solvent is also critical for the successful Jones oxidation. The Jones oxidation is a Chemical reaction described as the Chromic acid oxidation of primary and secondary Alcohols to Carboxylic acids 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. Laboratory glassware refers to a variety of equipment traditionally made of Glass, used for Scientific experiments and other work in Science, especially
Acetone is also used extensively for the safe transporting and storing of acetylene. Acetylene ( IUPAC name ethyne), C2H2 is a Hydrocarbon belonging to the group of Alkynes It is the simplest of all alkynes 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.
Feedstock
An important industrial use for acetone involves its reaction with phenol for the manufacture of bisphenol A. Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" Bisphenol A, commonly abbreviated as BPA, is an Organic compound with two Phenol Functional groups It is a difunctional building block of Bisphenol A is an important component of many polymers such as polycarbonates, polyurethanes and epoxy resins. A polyurethane, commonly abbreviated PU, is any Polymer consisting of a chain of organic units joined by urethane links In Chemistry, epoxy or polyepoxide is a Thermosetting Epoxide Polymer that cures (polymerizes and crosslinks when mixed with a Acetone has also been used in the manufacture of cordite. Cordite is a family of smokeless propellants developed and produced in the United Kingdom from 1889 to replace Gunpowder as a military propellant
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. [3] 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. [4][5][6] 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. MythBusters is a Popular science Television program produced by Australian firm Beyond Television Productions originally for the [7].
Other uses
Acetone is also used as a drying agent, due to the readiness with which it mixes with water, and its volatility. A Desiccant is a Hygroscopic substance that induces or sustains a state of dryness ( Desiccation) in its local vicinity in a moderately-well sealed container
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.
Safety
Acetone peroxide
When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. Acetone peroxide ( triacetone triperoxide, peroxyacetone, TATP, TCAP) is an Organic peroxide and a primary High It may be formed accidentally, e. g. when waste hydrogen peroxide is poured into a carboy containing waste acetone solvent. Hydrogen peroxide (H2O2 is a very pale blue liquid which appears colorless in a dilute solution slightly more Viscous than water Acetone peroxide is more than ten times as friction and shock sensitive as nitroglycerin. Nitroglycerin ( NG) ( US spelling also known as nitroglycerine, ( UK Spelling trinitroglycerin, trinitroglycerine Due to its instability, it is rarely used, despite its easy chemical synthesis.
Toxicology
Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). Drug metabolism in liver The human body identifies almost all drugs as foreign substances (i The vapors should be avoided. In no circumstance should it be consumed directly or indirectly. Always use goggles when handling acetone; it can cause permanent eye damage (corneal clouding).
Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see ketosis). Ketosis (kiːˈtoʊsɪs is a state in Metabolism occurring when the Liver excessively converts fat into fatty acids and Ketone Acetone can be elevated in diabetes. Diabetes mellitus (ˌdaɪəˈbiːtiːz or /ˌdaɪəˈbiːtəs/ /məˈlaɪtəs/ or /ˈmɛlətəs/ often referred to simply as diabetes ( Ancient Greek: grc 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. The mucous membranes (or mucosae; singular mucosa) are linings of mostly endodermal origin covered in Epithelium, which are involved in The mouth, buccal cavity, or oral cavity is the first portion of the Alimentary canal that receives food and begins digestion by mechanically breaking up Accidental intake of large amounts of acetone may lead to unconsciousness and death.
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. The kidneys are complicated organs that have numerous biological roles The liver is a vital organ in the human body and is present in Vertebrates and some other animals A nerve is an enclosed cable-like bundle of peripheral Axons (the long slender projections of Neurons. A congenital disorder is a disease or disorder that is present at birth 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.
Interestingly, acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations. The anticonvulsants, also called antiepileptic drugs (abbreviated "AEDs" are a diverse group of pharmaceuticals used in the treatment of epileptic Epilepsy is a common chronic Neurological disorder that is characterized by recurrent unprovoked seizures. [8] 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. The ketogenic diet is a high fat adequate Protein, low carbohydrate diet, primarily used to treat difficult-to-control (refractory Epilepsy in children [8]
References
- ^ Merck Index, 11th Edition, 58.
- ^ NALGENE Labware - Technical Data
- ^ Louis LaPonte (2007-02-13). Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1258 - Baghdad falls to the Mongols, and the Abbasid Caliphate is destroyed Acetone in Fuels (A Study of Dimethylketone or Propanone). Smartgas.net. Retrieved on 2007-06-06. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1508 - Maximilian I Holy Roman Emperor, is defeated in Friulia by Venetian forces; he is forced to sign a three-year
- ^ Acetone as a Fuel Additive. Pure Energy Systems Wiki. Retrieved on 2007-06-06. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1508 - Maximilian I Holy Roman Emperor, is defeated in Friulia by Venetian forces; he is forced to sign a three-year
- ^ Tom and Ray Magliozzi (2006-01-21). Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 1189 - Philip II of France and Richard I of England begin to assemble troops to wage the Third Crusade. Click and Clack Talk Cars. Independent Record. The Independent Record (often abbreviated to IR) is a daily paid-for Newspaper printed and distributed in Helena Montana. Retrieved on 2007-06-06. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1508 - Maximilian I Holy Roman Emperor, is defeated in Friulia by Venetian forces; he is forced to sign a three-year
- ^ Can adding Acetone to fuel increase mpg by 15 to 35%?. Snopes.com Message Board. Snopes (ˈsnoʊps also known as the Urban Legends Reference Pages, is a Web site that is the most widely-known resource for validating or debunking Urban legends Retrieved on 2007-06-06. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1508 - Maximilian I Holy Roman Emperor, is defeated in Friulia by Venetian forces; he is forced to sign a three-year
- ^ MythBusters (Season 4, Episode 53)
- ^ a b Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC 3rd, Burnham WM (2003). MythBusters is a Popular science Television program produced by Australian firm Beyond Television Productions originally for the The cast of the television series MythBusters perform experiments to verify or debunk Urban legends Old wives' tales and the like "Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet". Ann Neurol. 54 (2): 219–226. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
External links
- International Chemical Safety Card 0087
- National Pollutant Inventory – Acetone
- NIOSH Pocket Guide to Chemical Hazards
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