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Methanol
From Wikipedia, the free encyclopedia
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with formula CH3OH (often abbreviated MeOH). It is the simplest alcohol, and is a light, volatile, colorless, flammable, liquid with a distinctive odor that is very similar to but slightly sweeter than ethanol (drinking alcohol).[2] At room temperature it is a polar liquid and is used as an antifreeze, solvent, fuel, and as a denaturant for ethanol. It is also used for producing biodiesel via transesterification reaction. Methanol is produced naturally in the anaerobic metabolism of many varieties of bacteria, and is ubiquitous in the environment. As a result, there is a small fraction of methanol vapor in the atmosphere. Over the course of several days, atmospheric methanol is oxidized with the help of sunlight to carbon dioxide and water. Methanol burns in air forming carbon dioxide and water: 2 CH3OH + 3 O2 2 CO2 + 4 H2O A methanol flame is almost colorless in bright sunlight. Because of its toxic properties, methanol is frequently used as a denaturant additive for ethanol manufactured for industrial uses this addition of methanol exempts industrial ethanol from liquor excise taxation. Methanol is often called wood alcohol because it was once produced chiefly as a byproduct of the destructive distillation of wood.
CAS number PubChem ChemSpider RTECS number SMILES InChI
Methanol
IUPAC name methanol other names hydroxymethane methyl alcohol methyl hydrate wood alcohol carbinol Identifiers
1/CH4O/c1-2/h2H,1H3
Properties CH4 O 32.04 g mol1 colorless liquid 0.7918 g/cm3 97 C, 142.9 F (176 K)
Contents
1 History 2 Production 3 Applications 3.1 Feedstock 3.2 Fuel for vehicles 3.3 Other applications 4 Health and safety 4.1 Toxicity 4.2 Safety in automotive fuels 5 See also 6 Notes
Melting point
Boiling point 64.7 C, 148.4 F (337.8 K) Solubility in water Acidity (pKa) Viscosity Dipole moment MSDS EU classification miscible ~ 15.5 0.59 mPas at 20 C 1.69 D (gas) Hazards[1] External MSDS Flammable (F) Toxic (T)
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History
In their embalming process, the ancient Egyptians used a mixture of substances, including methanol, which they obtained from the pyrolysis of wood. Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of boxwood. It later became known as pyroxylic spirit. In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition.
12 C (54 F) (closed cup) Related compounds Related alcohols Ethanol Propanol Butanol Related compounds Chloromethane Methoxymethane Supplementary data page Structure and n, r, etc. properties Thermodynamic Phase behaviour data Solid, liquid, gas Spectral data UV, IR, NMR, MS (what is this?) (verify) (http://en.wikipedia.org /w/index.php?title=Methanol&diff=cur& oldid=266418673) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references Flash point
They also introduced the word methylene to organic chemistry, forming it from Greek methy = "wine" + hl = wood (patch of trees). Its intended origin was "alcohol made from wood (substance)", but it has Greek language errors: wrong Greek word used for the French word bois = "wood"; wrong Greek word combining order influenced by French usage. The term "methyl" was derived in about 1840 by back-formation from methylene, and was then applied to describe "methyl alcohol." This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature. The suffix -yl used in organic chemistry to form names of carbon groups, was extracted from the word "methyl."
In 1923 the German chemists Alwin Mittasch and Mathias Pier, working for BASF, developed a means to convert synthesis gas (a mixture of carbon monoxide, carbon dioxide, and hydrogen) into methanol. A patent was filed Jan 12 1926 (reference no. 1,569,775). This process used a chromium and manganese oxide catalyst, and required extremely vigorous conditionspressures ranging from 50 to 220 atm, and temperatures up to 450 C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures, the modern low pressure methanol (LPM) was developed by ICI in the late 1960s with the technology now owned[citation needed] by Johnson Matthey who is a leading licensor of methanol technology. The use of methanol as a motor fuel received attention during the oil crises of the 1970s due to its availability, low cost, and environmental benefits. By the mid-1990s, over 20,000 methanol "flexible fuel vehicles" capable of operating on methanol or gasoline were introduced in the U.S. In addition, low levels of methanol were blending in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol fueled vehicles. While the Methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished the interest in methanol fuels. In 2006 astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space, 300 billion miles across.
Production
Today, synthesis gas is most commonly produced from the methane component in natural gas rather than from coal. Three processes are commercially practiced. At moderate pressures of 4 MPa (40 atm) and high
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temperatures (around 850 C), methane reacts with steam on a nickel catalyst to produce syngas according to the chemical equation: CH4 + H2O CO + 3 H2 This reaction, commonly called steam-methane reforming or SMR, is endothermic and the heat transfer limitations place limits on the size of and pressure in the catalytic reactors used. Methane can also undergo partial oxidation with molecular oxygen to produce syngas, as the following equation shows: 2 CH4 + O2 2 CO + 4 H2 This reaction is exothermic and the heat given off can be used in-situ to drive the steam-methane reforming reaction. When the two processes are combined, it is referred to as autothermal reforming. The ratio of CO and H2 can be adjusted to some extent by the water-gas shift reaction, CO + H2O CO2 + H2, to provide the appropriate stoichiometry for methanol synthesis. The carbon monoxide and hydrogen then react on a second catalyst to produce methanol. Today, the most widely used catalyst is a mixture of copper, zinc oxide, and alumina first used by ICI in 1966. At 510 MPa (50100 atm) and 250 C, it can catalyze the production of methanol from carbon monoxide and hydrogen with high selectivity: CO + 2 H2 CH3OH It is worth noting that the production of synthesis gas from methane produces 3 moles of hydrogen for every mole of carbon monoxide, while the methanol synthesis consumes only 2 moles of hydrogen for every mole of carbon monoxide. One way of dealing with the excess hydrogen is to inject carbon dioxide into the methanol synthesis reactor, where it, too, reacts to form methanol according to the equation: CO2 + 3 H2 CH3OH + H2O Although natural gas is the most economical and widely used feedstock for methanol production, many other feedstocks can be used to produce syngas via steam reforming. Coal is increasingly being used as a feedstock for methanol production, particularly in China. In addition, mature technologies available for biomass gasification are being utilized for methanol production.
Applications
Methanol is a common laboratory solvent. It is especially useful for HPLC and UV/VIS spectroscopy due to its low UV cutoff.
Feedstock
The largest use of methanol by far is in making other chemicals. About 40% of methanol is converted to formaldehyde, and from there into products as diverse as plastics, plywood, paints, explosives, and permanent press textiles. Also in the early 1970s, a methanol to gasoline process was developed by Mobil for producing gasoline ready for use in vehicles. One such industrial facility was built at Motunui in New Zealand in the 1980s. In the 1990s, large amounts of methanol were used in the United States to produce the gasoline additive methyl tert-butyl ether (MTBE). While MTBE is no longer marketed in the U.S., it is still widely used in other parts of the world. In addition to direct use as a fuel, methanol (or less commonly, ethanol) is used as a component in the transesterification of triglycerides to yield a form of biodiesel.
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Other chemical derivatives of methanol include dimethyl ether, which has replaced chlorofluorocarbons as an aerosol spray propellant, and acetic acid. Dimethyl ether, or "DME" also can be blended with liquified petroleum gas (LPG) for home heating and cooking, and can be used as a diesel replacement transportation fuel.
Other applications
Methanol is a traditional denaturant for ethanol, thus giving the term methylated spirit.[3] Methanol is also used as a solvent, and as an antifreeze in pipelines and windshield washer fluid. In some wastewater treatment plants, a small amount of methanol is added to wastewater to provide a food source of carbon for the denitrifying bacteria, which convert nitrates to nitrogen to reduce the denitrification of sensitive aquifers. During World War II, methanol was used as a fuel in several German military rocket designs, under name M-Stoff, and in a mixture as C-Stoff.
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Methanol was used as an automobile coolant antifreeze in the early 1900s.[4] Methanol is used as a denaturing agent in polyacrylamide gel electrophoresis. Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, allowing them to be miniaturized to an unprecedented degree. This, combined with the relatively easy and safe storage and handling of methanol may open the possibility of fuel cell-powered consumer electronics, such as for laptop computers and mobile phones.[5] Methanol is also a widely used fuel in camping and boating stoves. Methanol burns well in an unpressurized burner, so alcohol stoves are often very simple, sometimes little more than a cup to hold fuel. This lack of complexity makes them a favorite of hikers who spend extended time in the wilderness. Methanol is mixed with water and injected into high performance diesel engines for and increase of power and a decrease in exhaust gas temperature. This is called water methanol injection.
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result is known as methylated spirit or "meths" (UK use). The latter should not be confused with meth, a common U.S. abbreviation for methamphetamine.
See also
Liquid fuels Methanol fuel List of Stoffs Methanol (data page) Methanol economy Deuterated methanol Prnu methanol tragedy Dimethyl ether
Notes
1. ^ "The Emergency Response Safety and Health Database: Systematic Agent: METHANOL" (http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750029.html#er) . Centers for Disease Control and Prevention. http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750029.html#er. Retrieved 26 August 2009. 2. ^ a b National Institute for Occupational Safety and Health (August 22, 2008). "The Emergency Response Safety and Health Database: Methanol" (http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750029.html) . http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750029.html. Retrieved March 17, 2009. 3. ^ http://www.slate.com/id/2245188/ 4. ^ http://pubs.acs.org/doi/abs/10.1021/ie50257a020 5. ^ Sandy Berger (September 30, 2006). "Methanol Laptop Fuel" (http://www.compukiss.com/populartopics /tech_gadgetshtm/article887.htm) . CompuKiss. http://www.compukiss.com/populartopics/tech_gadgetshtm /article887.htm. Retrieved 2007-05-22. 6. ^ a b Vale A (2007). "Methanol". Medicine 35 (12): 633-4. doi:10.1016/j.mpmed.2007.09.014 (http://dx.doi.org /10.1016/j.mpmed.2007.09.014) . 7. ^ a b c d e f Schep LJ, Slaughter RJ, Vale JA, Beasley DM (Sep 30 2009). "A seaman with blindness and confusion" (http://www.bmj.com/cgi/content/full/339/sep30_1/b3929) . BMJ 339: b3929. doi:10.1136/bmj.b3929 (http://dx.doi.org/10.1136/bmj.b3929) . PMID 19793790 (http://www.ncbi.nlm.nih.gov /pubmed/19793790) . http://www.bmj.com/cgi/content/full/339/sep30_1/b3929. 8. ^ McMartin KE, Martin-Amat G, Noker PE, Tephly TR (March 1979). "Lack of a role for formaldehyde in methanol poisoning in the monkey" (http://linkinghub.elsevier.com/retrieve/pii/0006-2952%2879%2990149-7) . Biochem. Pharmacol. 28 (5): 6459. doi:10.1016/0006-2952(79)90149-7 (http://dx.doi.org/10.1016
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