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ddition to the lower carbon emissions 51 ethanol combustion in an internal combustion engine yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of formaldehyde and related species such as acetaldehyde 52 this leads to a significantly larger photochemical reactivity and more ground level ozone 53 this data has been assembled into the clean fuels report comparison of fuel emissions 54 and show that ethanol exhaust generates 2 14 times as much ozone as gasoline exhaust 55 when this is added into the custom localized pollution index of the clean fuels report the local pollution of ethanol pollution that contributes to smog is rated 1 7 where gasoline is 1 0 and higher numbers signify greater pollution 56 the california air resources board formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group much like the conventional no x and reactive organic gases rogs 57 more than 20 of brazilian cars are able to use 100 ethanol as fuel which includes ethanol only engines and flex fuel engines 58 flex fuel engines in brazil are able to work with all ethanol all gasoline or any mixture of both in the united states flex fuel vehicles can run on 0 to 85 ethanol 15 gasoline since higher ethanol blends are not yet allowed or efficient brazil supports this fleet of ethanol burning automobiles with large national infrastructure that produces ethanol from domestically grown sugarcane the indian government has heavily promoted ethanol blending recently approving e100 for the first time 59 ethanol s high miscibility with water makes it unsuitable for shipping through modern pipelines like liquid hydrocarbons 60 mechanics have seen increased cases of damage to small engines in particular the carburetor and attribute the damage to the increased water retention by ethanol in fuel 61 ethanol was commonly used as fuel in early bipropellant rocket liquid propelled vehicles in conjunction with an oxidizer such as liquid oxygen the german a 4 ballistic rocket of world war ii better known by its propaganda name v 2 62 which is credited as having begun the space age used ethanol as the main constituent of b stoff under such nomenclature the ethanol was mixed with 25 water to reduce the combustion chamber temperature 63 64 the v 2 s design team helped develop u s rockets following world war ii including the ethanol fueled redstone rocket which launched the first u s astronaut on suborbital spaceflight 65 66 alcohols fell into general disuse as more energy dense rocket fuels were developed 64 although ethanol was used in recent experimental lightweight rocket powered racing aircraft 67 commercial fuel cells operate on reformed natural gas hydrogen or methanol ethanol is an attractive alternative due to its wide availability low cost high purity and low toxicity there is a wide range of fuel cell concepts that have entered trials including direct ethanol fuel cells auto thermal reforming systems and thermally integrated systems the majority of work is being conducted at a research level although there are a number of organizations at the beginning of the commercialization of ethanol fuel cells 68 ethanol fireplaces can be used for home heating or for decoration ethanol can also be used as stove fuel for cooking 69 70 energy content lower heating value of some fuels compared with ethanol fuel type mj l mj kg research octane number dry wood 20 moisture 19 5 methanol 17 9 19 9 108 7 71 ethanol 21 2 72 26 8 72 108 6 71 e85 85 ethanol 15 gasoline 25 2 33 2 105 liquefied natural gas 25 3 55 autogas lpg 60 propane 40 butane 26 8 50 aviation gasoline high octane gasoline not jet fuel 33 5 46 8 100 130 lean rich gasohol 90 gasoline 10 ethanol 33 7 47 1 93 94 regular gasoline petrol 34 8 44 4 72 min 91 premium gasoline petrol max 104 diesel 38 6 45 4 25 charcoal extruded 50 23 other uses edit ethanol is an important industrial ingredient with widespread uses as a precursor for other organic compounds such as ethyl halides ethyl esters diethyl ether acetic acid and ethyl amines as ethanol also has a low boiling point it is easy to remove from a solution that has been used to dissolve other compounds making it a popular extracting agent for botanical oils ethanol is found in paints tinctures markers personal care products such as mouthwashes perfumes and deodorants and wet specimen preservatives 73 polysaccharides precipitate from aqueous solution in the presence of alcohol and ethanol precipitation is used for this reason in the purification of dna and rna 74 because of its low freezing point of 114 c 173 f and low toxicity ethanol is sometimes used in laboratories with dry ice or other coolants as a cooling bath to keep vessels at temperatures below the freezing point of water 75 for the same reason it is also used as the active fluid in alcohol thermometers ethanol is also used in removing several stains as it is considered a universal solvent its molecular structure allows for the dissolving of both polar hydrophilic and nonpolar hydrophobic compounds it can be used to dissolve oils 76 inks 77 and other substances chemistry edit this section needs more citations please help improve this section by adding citations to reliable sources unsourced material may be challenged and removed november 2024 learn how and when to remove this message further information ethanol data page ethanol is a 2 carbon alcohol its molecular formula is ch 3 ch 2 oh the structure of the molecule of ethanol is ch 3 ch 2 oh an ethyl group linked to a hydroxyl group which indicates that the carbon of a methyl group ch 3 is attached to the carbon of a methylene group ch 2 which is attached to the oxygen of a hydroxyl group oh it is a constitutional isomer of dimethyl ether ethanol is sometimes abbreviated as etoh using the common organic chemistry notation of representing the ethyl group ch 2 ch 3 with et physical properties edit ethanol burning with its spectrum depicted ethanol is a volatile colorless liquid that has a slight odor it burns with a smokeless blue flame that is not always visible in normal light the physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain ethanol s hydroxyl group is able to participate in hydrogen bonding rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight such as propane 78 ethanol s adiabatic flame temperature for combustion in air is 2082 c or 3779 f 79 ethanol is slightly more refractive than water having a refractive index of 1 36242 at λ 589 3 nm and 18 35 c or 65 03 f 80 the triple point for ethanol is 150 20 k 81 solvent properties edit ethanol is a versatile solvent miscible with water and with many organic solvents including acetic acid acetone benzene carbon tetrachloride chloroform diethyl ether ethylene glycol glycerol nitromethane pyridine and toluene its main use as a solvent is in making tincture of iodine cough syrups etc 80 82 it is also miscible with light aliphatic hydrocarbons such as pentane and hexane and with aliphatic chlorides such as trichloroethane and tetrachloroethylene 82 ethanol s miscibility with water contrasts with the immiscibility of longer chain alcohols five or more carbon atoms whose water miscibility decreases sharply as the number of carbons increases 83 the miscibility of ethanol with alkanes is limited to alkanes up to undecane mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature about 13 c for dodecane 84 the miscibility gap tends to get wider with higher alkanes and the temperature for complete miscibility increases ethanol water mixtures have less volume than the sum of their individual components at the given fractions mixing equal volumes of ethanol and water results in only 1 92 volumes of mixture 80 85 mixing ethanol and water is exothermic with up to 777 j mol 86 being released at 298 k hydrogen bonding in solid ethanol at 186 c hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air the polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds notably sodium and potassium hydroxides magnesium chloride calcium chloride ammonium chloride ammonium bromide and sodium bromide 82 sodium and potassium chlorides are slightly soluble in ethanol 82 because the ethanol molecule also has a nonpolar end it will also dissolve nonpolar substances including most essential oils 87 and numerous flavoring coloring and medicinal agents the addition of even a few percent of ethanol to water sharply reduces the surface tension of water this property partially explains the tears of wine phenomenon when wine is swirled in a glass ethanol evaporates quickly from the thin film of wine on the wall of the glass as the wine s ethanol content decreases its surface tension increases and the thin film beads up and runs down the glass in channels rather than as a smooth sheet azeotrope with water edit at atmospheric pressure mixtures of ethanol and water form an azeotrope at about 89 4 mol ethanol 95 6 ethanol by mass 88 97 alcohol by volume with a boiling point of 351 3 k 78 2 c 172 7 f 89 at lower pressure the composition of the ethanol water azeotrope shifts to more ethanol rich mixtures 90 the minimum pressure azeotrope has an ethanol fraction of 100 90 and a boiling point of 306 k 33 c 91 f 89 corresponding to a pressure of roughly 70 torr 9 333 kpa 91 below this pressure there is no azeotrope and it is possible to distill absolute ethanol from an ethanol water mixture 91 flammability edit an ethanol water solution will catch fire if heated above a temperature called its flash point and an ignition source is then applied to it 92 for 20 alcohol by mass about 25 by volume this will occur at about 25 c 77 f the flash point of pure ethanol is 13 c 55 f 93 but may be influenced very slightly by atmospheric composition such as pressure and humidity ethanol mixtures can ignite below average room temperature ethanol is considered a flammable liquid class 3 hazardous material in concentrations above 2 35 by mass 3 0 by volume 6 proof 94 95 96 flash points of ethanol water mixtures 97 95 98 ethanol mole fraction temperature c f 1 84 5 184 1 95 2 64 147 95 2 35 60 140 95 94 3 51 5 124 7 95 5 43 109 97 6 39 5 103 1 95 10 31 88 97 20 25 77 95 30 24 75 97 50 20 68 97 95 70 16 61 97 80 15 8 60 4 95 90 14 57 97 100 12 5 54 5 97 95 93 natural occurrence edit ethanol is a byproduct of the metabolic process of yeast as such ethanol will be present in any yeast habitat ethanol can commonly be found in overripe fruit 99 ethanol produced by symbiotic yeast can be found in bertam palm blossoms although some animal species such as the pentailed treeshrew exhibit ethanol seeking behaviors most show no interest or avoidance of food sources containing ethanol 100 ethanol is also produced during the germination of many plants as a result of natural anaerobiosis 101 ethanol has been detected in outer space forming an icy coating around dust grains in interstellar clouds 102 minute quantity amounts average 196 ppb of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers 103 auto brewery syndrome also known as gut fermentation syndrome is a rare medical condition in which intoxicating quantities of ethanol are produced through endogenous fermentation within the digestive system 104 production edit 94 denatured ethanol sold in a bottle for household use ethanol is produced both as a petrochemical through the hydration of ethylene and via biological processes by fermenting sugars with yeast 105 which process is more economical depends on prevailing prices of petroleum and grain feed stocks sources edit world production of ethanol in 2006 was 51 gigalitres 1 3 10 10 us gal with 69 of the world supply coming from brazil and the u s 16 brazilian ethanol is produced from sugarcane which has relatively high yields 830 more fuel than the fossil fuels used to produce it compared to some other energy crops 106 sugarcane not only has a greater concentration of sucrose than corn by about 30 but is also much easier to extract the bagasse generated by the process is not discarded but burned by power plants to produce electricity bagasse burning accounts for around 9 of the electricity produced in brazil 107 in the 1970s most industrial ethanol in the u s was made as a petrochemical but in the 1980s the u s introduced subsidies for corn based ethanol 108 according to the renewable fuels association as of 30 october 2007 131 grain ethanol bio refineries in the u s have the capacity to produce 7 billion us gallons 26 000 000 m 3 of ethanol per year an additional 72 construction projects underway in the u s can add 6 4 billion us gallons 24 000 000 m 3 of new capacity in the next 18 months 47 in india ethanol is made from sugarcane 109 sweet sorghum is another potential source of ethanol and is suitable for growing in dryland conditions the international crops research institute for the semi arid tropics is investigating the possibility of growing sorghum as a source of fuel food and animal feed in arid parts of asia and africa 110 sweet sorghum has one third the water requirement of sugarcane over the same time period it also requires about 22 less water than corn the world s first sweet sorghum ethanol distillery began commercial production in 2007 in andhra pradesh india 111 ethanol has been produced in the laboratory by converting carbon dioxide via biological and electrochemical reactions 112 113 co 2 h 2 o ch 3 ch 2 o h side products hydration edit ethanol can be produced from petrochemical feed stocks primarily by the acid catalyzed hydration of ethylene it is often referred to as synthetic ethanol c 2 h 4 h 2 o c 2 h 5 oh the catalyst is most commonly phosphoric acid 114 115 adsorbed onto a porous support such as silica gel or diatomaceous earth this catalyst was first used for large scale ethanol production by the shell oil company in 1947 116 82 the reaction is carried out in the presence of high pressure steam at 300 c 572 f where a 5 3 ethylene to steam ratio is maintained 117 118 this process was used on an industrial scale by union carbide corporation and others it is no longer practiced in the us as fermentation ethanol produced from corn is more economical 119 in an older process first practiced on the industrial scale in 1930 by union carbide 116 817 120 but now almost entirely obsolete ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate which was hydrolyzed to yield ethanol and regenerate the sulfuric acid 121 c 2 h 4 h 2 so 4 c 2 h 5 hso 4 c 2 h 5 hso 4 h 2 o h 2 so 4 c 2 h 5 oh fermentation edit this section needs more citations please help improve this section by adding citations to reliable sources unsourced material may...