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Fuels and Lubricants 11/2/05 FUELS AND LUBRICANTS 11/2/05 Introduction A fuel is any substance that is burned or reacted to provide heat and other forms of energy. In 2000, an estimated 40% of the energy needs of the United States were supplied by oil or petroleum fuels. The rest was provided by natural gas (approximately 23%), coal (23%), nuclear power (8%) and other renewable sources (6.3% percent). In 2000, the US consumed a total of 1.0 x 1017 kJ of energy. This value corresponds to an average daily energy consumption per person of 1.0 x 106 kJ, which is roughly 100 times greater than the per capita food-energy needs. In addition to energy, petroleum is the source of numerous organic chemicals used to manufacture drugs, clothing, and many other products. Petroleum deposits are widely distributed throughout the world, but they are found mainly in North America, Mexico, Russia, China, Venezuela, and of course, the Middle East. Petroleum was formed in the Earth’s crust over the course of millions of years by the anaerobic (without oxygen) decomposition of animal and vegetable matter by bacteria. Unrefined petroleum, a viscous, dark-brown liquid, is often called crude oil. Crude oil is a complex mixture of compounds consisting mainly of hydrocarbons (compounds containing only hydrogen and carbon), a small amount of organic compounds containing sulfur, nitrogen, and oxygen, and some metallic compounds containing vanadium, nickel, iron and copper. Table I gives the percent by mass of the most common elements in a representative sample of crude oil. The graph shows the cost of crude oil over the past 30 years. Average crude oil prices over the past 30 years $70.00 Table I: Percent Composition of Crude Oil $60.00 Carbon 83.0 - 87.0% $50.00 Hydrogen 10.0 - 14.0% $40.00 Nitrogen 0.1 - 2.0% $30.00 Oxygen 0.05 - 1.5% $20.00 Sulfur 0.05 - 6.0% cost ($) per barrel $10.00 $0.00 1975 1980 1985 1990 1995 2000 2005 Table I indicates that crude oil consists largely of hydrocarbons. Hydrocarbons are an extremely broad class of organic compounds, and we’ll only be focusing on a few specific types in our discussion of fuels and lubricants. The next section provides some basic terms and definitions pertaining to hydrocarbons. Hydrocarbon Background Information Alkanes are hydrocarbons that contain carbon-carbon single bonds (no multiple bonds) and have the general chemical formula of CnH2n+2. The table below provides the parent names for alkanes as a function of the number of carbon atoms. Alkanes can be classified as a straight-chain, branched, or cyclic depending on their structure. Examples of each are presented below. 1 Table II: Simple Alkanes a. Straight-chain Alkanes: # of C atoms Parent Name H H H H H H H HCC H HCC C C C H 1 methane H H H H H H H 2 ethane Ethane Pentane 3 propane C H C 5H 12 2 6 4 butane CH3 CH3 CH3CH2CH2CH2CH3 5 pentane H H H H H H H H HCC C C C C C C H 6 hexane H H H H H H H H 7heptane Octane 8 octane C 8H 18 CH CH CH CH CH CH CH CH 9 nonane 3 2 2 2 2 2 2 3 10 decane For the straight-chain alkanes it is important that you be able to translate between the parent name (see Table II), the Lewis structure, and the molecular formula. Notice that the molecular formula can be written with the carbon atoms and their connected hydrogen atoms shown explicitly like in CH3CH2CH2CH3, or, in a more condensed way as in C4H10. For drawing the Lewis structures, follow the guidelines that carbon atoms form 4 Moo bonds and hydrogen forms only one bond. The simplest alkane is methane, CH4, a principle component of natural gas and classified as a greenhouse gas. Animal flatulation accounts for 17% of global methane emissions. A single cow is estimated to produce 600 L of methane every day. b. Branched Alkanes: The names and structures of the branched alkanes are H C CH H H3C H 3 3 CH3 H H more complicated than those of the straight-chain alkanes and C C C C H C C CH H C C CH are somewhat beyond the scope of our current discussion. It 3 3 3 3 H H H H is important that, given a Lewis structure of an alkane, you are 2,2,4-trimethylpentane 2-methylpentane able to classify it as straight-chain or branched. Isomers are (a.k.a. isooctane) (a.k.a. isohexane) compounds that have the same molecular formula, but different structures. In other words they have the same number and type of atoms, but the atoms are arranged differently. Notice that the branched alkanes shown above are each isomers of straight-chain alkanes. 2,2,4-trimethylpentane is an isomer of octane (both have the molecular formula, C8H18) and 2-methylpentane is an isomer of hexane (C6H14). c. Cyclic Alkanes: H H H H C We won’t focus much on cyclic alkanes in our discussion here. Notice that the H H C C generic formula for cyclic alkanes becomes CnH2n rather than the CnH2n+2 that is mentioned H C C H C above. This is because in going from a straight-chain alkane to a cyclic alkane, the two end H H hydrogens must be removed so that the ends of the chain can be tied together with a carbon- H H carbon bond to make a loop. cyclohexane d. Other Hydrocarbons: Alkenes are hydrocarbons that contain carbon-carbon double bonds. The simplest alkene is 2 ethene or ethylene with the formula, C2H4. Alkynes contain carbon-carbon triple bonds with the simplest alkyne being C2H2, ethyne or acetylene. Hydrocarbons that contain any multiple bonds (double or triple) are known as unsaturated hydrocarbons, while those with only single bonds are known as saturated hydrocarbons. Another common class of hydrocarbons that contains a ring structure is the aromatic hydrocarbons. Aromatic hydrocarbons are not cyclic alkanes because alkanes contain only single bonds between carbons, and the aromatic hydrocarbons feature multiple bonds. Benzene is the prototypical aromatic hydrocarbon and it is shown below. There are other more complicated aromatics that contain benzene rings. One might conclude, based on the Lewis structure of benzene shown below, that benzene consists of alternating single and double bonds with the single bonds being longer than the stronger double bonds. However, experiments show that all of the bonds in benzene are the same length. Benzene has more than one valid Lewis structure (i.e., there is resonance). Thus, the best description of the structure of benzene is a hybrid (average) of the two resonance contributors. Aromatic Hydrocarbons: Benzene’s resonance contributors: H H H H H C H H C C H H C C C C C H C H H C H C C C C C C C C C H C H H C C H C C C C H H H H C H H C H H H Benzene Naphthalene Fractional Distillation of Petroleum The refining of petroleum begins with the separation of the crude oil into groups of compounds with distinct boiling point ranges. Since crude petroleum contains literally thousands of hydrocarbon compounds, separation of the crude into pure compounds is neither feasible nor necessary. Rather, the petroleum fractions that are obtained are often mixtures of hundreds of hydrocarbons with boiling points within certain ranges. The physical properties of petroleum fractions determine their eventual end use. Table III lists common fractions obtained from crude oil with their approximate boiling ranges. Those compounds containing sulfur and nitrogen are generally undesirable in commercial petroleum products and are often removed by additionally refining the petroleum fractions obtained through distillation. Table III: Petroleum Fractions Fraction Carbon Atoms in chain Boiling Pt. Range (°C) Uses Natural gas C1-C4 -161 to 20 Fuel and cooking gas Petroleum ether C5-C6 30-60 Solvent for organic compounds Ligroin C7 20-135 Solvent for organic compounds Gasoline C6-C12 30-180 Automobile fuels Kerosene C11-C16 170-290 Rocket and jet engine fuels, domestic heating Heating Fuel Oil C14-C18 260-350 Domestic heating and fuel for electricity production Lubricating Oil C15-C24 300-370 Lubricants for automobiles and machines Paraffins C20 and up Low-melting solids Candles, matches Asphalt C30 and up Gummy residues Surfacing roads, fuel 3 To accomplish the separation, the dark brown, thick crude oil is heated to about 400oC to convert it into a mixture of hot vapor and fluid that is fed into the bottom of a fractional distillation tower. The distilling tower is divided into horizontal zones of different temperatures. The unvaporized, liquid portion of the feed is drawn off at the bottom of the tower as the tar and asphalt fractions. In the distillation tower the temperature decreases the further up the tower the vapor goes. Therefore, different components condense at various points within the tower; the volatile, lower boiling petroleum fractions remaining in the vapor phase longer than the less volatile, higher boiling fractions. After condensing, the liquid fractions are drawn off and collected. The lightest, most volatile hydrocarbons do not condense and are drawn off at the top of the tower as gases (See Figure I). Figure I: Distillation Tower Lowest Boiling Natural Gas Fractions Petroleum Ether Ligroin Gasoline Kerosene/Jet Fuels Heating Oil Lube Oil Crude Oil Paraffins Highest Boiling Fractions Asphalt For more information about oil refining, go to http://science.howstuffworks.com/oil-refining.htm.
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