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By: Alec

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Compound Name:
Kerosene
IUPAC Name:
Dodecane
Formula:
C12H26
Molar Mass:
170.34 g/mol
Density:
0.75 g/cm3 at 25°C (Liquid)
Melting Point:
-9.6°C
Boiling Point:
216.2°C



Background Information


Kerosene is a combustible, hydrocarbon liquid that is both thin and clear. Kerosene is also known as dodecane, which is its IUPAC name. Dodecane is an alkane with 12 carbons in a straight-chain of single bonds. Dodecane has 26 hydrogens in its total compound. Because of its tendency to produce flames and combust, kerosene is commonly found as a fuel nowadays or was found as a fuel at some point in time. Typically, kerosene is kept in a blue container to avoid the confusion of one thinking that kerosene is gasoline, which is much more flammable. Gasoline is typically held in a red container. In some parts of the world, it is legally required that each flammable liquid is placed in its proper color-coded container.


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Kerosene in Color-Coded Container
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Kerosene

Places of Existence and Obtaining Processes


Early processes found that heating coal in a retort led to the distillation which produced a thin, clear liquid known as kerosene. Other early processes in obtaining fuel consisted of heating oil shale and bitumen to extract the oil, which was then distilled. Today, kerosene is obtained from the fractional distillation of petroleum. The temperature range needed for this distillation to occur is 150 degrees Celsius to 275 degrees Celsius. If kerosene is directly distilled from crude oil, it requires some more treatment. The treatment occurs either in a Merox unit or a hydrotreater to reduce its sulfur content and its corrosiveness.

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Generic Distillation Process
Kerosene can be found fueling many different parts of the world. For instance, kerosene can be found in jet fuel, kerosene lamps and lanterns, kerosene space heaters, bi-fuel engines, kerosene portable stoves, and even as main components of fire acts used for entertainment.

Historical Discovery


Distilling crude oil/petroleum into kerosene dates back to the mid 800's. Persian scholar, Razi (Rhazes), wrote the process for distilling oil into kerosene and other hydrocarbon compounds. Razi was a phsician and chemist who used two different methods for the production of naft abyad ("white naphta"), or kerosene as we know it. One method involved using clay as an absorbant as the other used ammonium chloride as the absorbent. Razi continued with his distillation processes until the final product was safe to light when reaching a perfectly clear state. Razi was not the only man on track to making kerosene discoveries in his time; others produced kerosene from oil shale and bitumen by heating the rock to extract the oil, which was then distilled.

The modern discovery of kerosene can be credited to Abraham Gesner, a Canadian geologist. Gesner gave his groundbreaking demonstration in Charlottetwon, Prince Edward Island in 1846. By heating coal in retort, Gesner distilled a clear, thin fluid which to his discovery, made an excellent lamp fuel. He gave "his" liquid the name "kerosene", contradicting the Greek word keroselaion, which means wax-oil. Knowing that the cost of extracting kerosene from coal was rather high, Gesner took his idea to Newton Creek, Long Island in 1854 where he and a group of business men formed the North American Gas Light Company. Forming this company, Gesner and his business men assigned patents to his discovery. His patents, however, were not obtained until 1854, which is two years after James Young's US patent, despite the fact that Gesner had clear priority of the discovery. Gesner's processes were much cleaner and better smelling than those of Young. Therefore, Gesner's processes were put to use as the manufacturing of kerosene made way in New York in 1854 and continued in Boston.

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Abraham Gesner

Chemical Properties and Reaction Tendencies


As mentioned above, kerosene is a thin, clear liquid formed from hydrocarbons. Kerosene, or dodecane, has a density of .75 g/cm3. The flash point of kerosene is between 37 and 65 degrees Celsius. Its autoignition temperature is 220 dedgrees Celsius. Kerosene's heat of combustion can be found very similar to that of diesel, which is around 18,500 Btu/Ib. The higher heating value of kerosene 46.2 MJ/kg. Lastly, kerosene is immiscible in hot or cold water; however, kerosene is miscible in petroleum solvents.

Kerosene's reaction tendency is combustion. A combustion reaction is the sequence of exothermic chemical reactions between a fuel and an oxident accompanied by the production of heat and conversion of chemical species. In this case, the fuel is kerosene, and this example of a combustion reaction of kerosene, or dodecane, is shown below:


2C12H26(l) + 37O2(g) → 24CO2(g) + 26H2O(g)


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Kerosene Combustion Experiment

Structure


Bonding Types:
Kerosene, or dodecane, is consisted of 12 carbon atoms and 26 hydrogen atoms. Because carbon and hydrogen atoms are non-metals, the bonds are covalent.

Atom Arrangement:
The carbon atoms are arranged in a straight chain. The two outermost carbon atoms have three hydrogens attached to its atom. The ten middle carbons have two hydrogens each attached to its atom.

Percent Composition by Number:
Carbon: 12/38 = 31%
Hydrogen: 26/38 = 69%

Percent Composition by Mass:
Carbon: 12 mol C * (12.01g) = (144.12 g) / (170.34 g) = 84.6%
Hydrogen: 26 mol C * (1.01g) = (26.26 g) / (170.34 g) = 15.4%

Important Uses


Heating and Lighting
Replacing whale oil, kerosene was at one time the fuel widely used in kerosene lamps and lanterns. Kerosene, as most know, is a major fire risk. Two out of every five New York City fires were caused by defective kerosene lamps in 1880. In today's world, kerosene lamps and lanterns are replaced by the light bulb and flashlights powered by batteries. As far as being used as a cooking fuel, kerosene is restricted to portable stoves for hikers and to less developed countries. In heating, kerosene is used as the fuel in portable stoves, and is sold in some filling stations. During some power failures, kerosene may be used as a heat source. Because of carbon monoxide gas build-up, using portable heaters fueled by kerosene is not recommended for closed indoor areas.


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Transportation
During the 1900s, kerosene was used as cheap tractor fuel. Being that gasoline is more expensive, tractor engines would initially start on gasoline and switch over to kerosene after the engine warmed up. Kerosene is used as the fuel of smaller horsepower motors built by companies such as Yamaha, Suzuki, and Tohatsu. The kerosene engines built by these companies are bi-fuel motors that start on gasoline and switch to kerosene, similar to the tractor engines mentioned above. In today's world, kerosene's place in fueling the transportation lies in jet engines. One form of jet kerosene fuel known as RP-1 is burned with liquid oxygen as rocket fuel.

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Kerosene-Fueled Jet A1 Engine

Entertainment
Kerosene can also be found in the entertainment industry. During some fire performances such as fire breathing, fire juggling, and fire dancing, kerosene plays the important "fueling key". When burnt in free air, kerosene burns with a low flame temperature. Thus, the risk is lower and the performer has a "safety net" to fall back on if coming in contact with the flame. Methanol was once used for such entertaining activities. However, the flames methanol produced were less impressive to viewers, and on a more concerning level, methanol is highly toxic for the optical nerves and cause blindness when swallowed. Therefore, kerosene took its place in today's lifetime.


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Health Hazards


Inhalation:
If one happens to inhale kerosene, it causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath, a burning in the chest, headache, nausea, weakness, restlessness, and drowsiness.

Ingestion:
If one happens to inhale kerosene, it causes irritation to the gastrointestinal tract. Symptoms may include nausea, vomiting and diarrhea. Ingestion may cause damage to the lungs.

Skin Contact:
If kerosene comes into contact with the skin, irritation can occur. Symptoms may include redness, itching, and pain.

Eye Contact:
If kerosene comes into contact with the eyes, severe irritation and pain can occur.


3-D Model


To see the 3-D molecule of dodecane, download iMoll and click on the link above to open and view the file.

References


Websites:
"Kerosene." Wikipedia. Web. 22 Oct. 2010. http://en.wikipedia.org/wiki/Kerosene.
"Dodecane." Wikipedia. Web. 22 Oct. 2010. http://en.wikipedia.org/wiki/Dodecane.
"Dodecane." ChemBlink. Web. 23 Oct. 2010. http://www.chemblink.com/products/112-40-3.htm.
"DODECANE." Web. 23 Oct. 2010. http://www.jtbaker.com/msds/englishhtml/d8752.htm.
"Kerosene Fuel Oil United Paraffin." ECONOMICexpert. Web. 26 Oct. 2010. http://www.economicexpert.com/a/Kerosene.htm.




Images:
Ball and Stick Structure of Dodecane: http://rpmedia.ask.com/ts?u=/wikipedia/commons/thumb/7/7b/Dodecane-3D-balls-B.png/300px-Dodecane-3D-balls-B.png
Kerosene Container: http://www.wmbarr.com/Images/ProductImages/KEROSENE.jpg
Kerosene Liquid: http://www.blackwaterfuels.co.uk/images/liquid2.jpg
Generic Distillation Process: http://www.ktf-split.hr/glossary/image/distillation.gif
Abraham Gesner: http://www.thelampworks.com/images/tr_gesner.jpg
Kerosene Combustion Reaction: http://i.ytimg.com/vi/nnPrpZQh5DQ/0.jpg
Kerosene Lantern: http://www.wordjourney.com/images/kerosene-lamp.jpg
Jet Engine: http://www.mycleansky.com/images/jetengine.jpg
Fire Breather: http://www.squidoo.com/whatisfirebreathing



3-D Molecule:
To save the file: http://www.journal.chemistrycentral.com/content/supplementary/1752-153x-1-31-s1/Jmol/examples/MS/dodecaneJ/dodecane.mol
Actual website found: http://www.journal.chemistrycentral.com/content/supplementary/1752-153x-1-31-s1/Jmol/examples/MS/dodecaneJ/index.html