Lecture on Alkanes

Alkanes are said to be "saturated" and this means that there are the maximum number of hydrogen atoms attached to each carbon.
There are no double bonds. This makes them better fuels, as they release more energy in a combustion reaction.
Alkanes are non-polar. The C-H bond is weakly polar, due to difference in electronegativity between C and H atoms, however due to
the symmetry of C-H bonds around the whole alkane, any dipoles are even in size and balance or cancel out. This means that alkanes
do not mix with water.
Alkanes have low melting or boiling points because of the very weak intermolecular forces between alkane molecules. Methane,
ethane, propane, and butane are gases at room temperature.
As the carbon chain gets longer, there are more electrons in a molecule. This means that there are more (relatively) stronger
intermolecular forces between the molecules. As a result, it takes more energy to break these forces, and thus the melting or boiling
points increase.
As the carbon chain increases in length, there are more intermolecular forces holding molecules together. This means that the
substance will become denser as the carbon chain increases. Oils are very viscous, and can have carbon chains of over 25 carbons!
* Alkanes are not very reactive and have little biological activity
* all alkanes are colorless and odorless non-polar compounds
* The relative weak London dispersion forces of alkanes result in gaseous substances for short carbon chains, volatile liquids
with densities around 0.7 g/mL for moderate carbon chains, and solids for long carbon chains.
* Alkanes containing 1 to 4 carbons are gases at room temperature, and those containing 5 to 17 carbons are colorless
liquids.
* High molecular weight alkanes (those with 18 or more carbons) are white, waxy solids.
* Ex. Apple skin, Paraffin wax, Petrolatum
* The most important property of alkanes and cycloalkanes is their almost complete lack of polarity.
* There is not a significant electronegativity difference between carbon and hydrogen, thus, there is not any significant bond
polarity. The molecules themselves also have very little polarity. A totally symmetrical molecule like methane is completely
non-polar, meaning that the only attractions between one molecule and its neighbors will be Van der Waals dispersion
forces. These forces will be very small for a molecule like methane but will increase as the molecules get bigger. Therefore,
the boiling points of the alkanes increase with molecular size.
* In general, both boiling and melting points of alkanes increase with increasing molecular weight.
* Because interactions between alkane molecules consist only of these very weak dispersion forces, the boiling points of
alkanes are lower than those of almost any other type of compound of the same molecular weight.
* As the number of atoms and the molecular weight of an alkane increase, the strength of the dispersion forces among
alkane molecules increases and consequently, boiling points increase.
* Three major sources of alkanes: Fossil fuels
* Natural gas- Consists of approx. 90-95% methane, 5-10% ethane, mixture of relatively low boiling alkanes- chiefly propane,
butane, 2-methylpropane.
* Petroleum- Thick, viscous liquid mixture of literally thousands of compounds. Formed from the composition of marine
plants and animals. Fuel automobiles, aircrafts, and trains greases and lubricants for machines Along with natural gas, raw
materials in manufacture of synthetic fibers, drugs, dyes etc.
Separation process in refining petroleum is fractional distillation.
1. Gases below 20C are taken off at the top of the distillation column. (LPG)
2. Napthas, bp 20C to 200 C, mixtures of C5 to C12 alkanes and cycloalkanes. Contains small amount of benzene, toluene,
xylene and other aromatic compounds.(gasoline)
3. Kerosene, bp 175C to 275C, is a mixtures of C9 to C15 hydrocrbons.
4. Fuel oil, bp 250C to 400C, C15 to C18 HC. (Diesel)
5. Lubricating oil and heavy oil distill from the column at temperature above 350C.
6. Asphalt is the black, tarry residue remaining after the removal of the other volatile fractions.
The process of fractional distillation
Separating molecules according to their boiling points.
1. Crude oil heated.
2. Enters column as a gas.
3. Larger molecules condense at the bottom where it is hottest.
4. Smaller molecules condense at the top where it is cooler.
Uses of different crude oil fractions
Gases - cooking and heating.
Petrol - car fuel.
Naphtha - lighter fuel.
Kerosene - aircraft fuel.
Diesel - lorry/train fuel.
Fuel oil - ship/power station fuel.
Bitumen - road/roof surfacing.
Cracking is the name given to breaking up large hydrocarbon molecules into smaller and more useful bits. This is achieved by using
high pressures and temperatures without a catalyst, or lower temperatures and pressures in the presence of a catalyst. The source
of the large hydrocarbon molecules is often the naphtha fraction or the gas oil fraction from the fractional distillation of crude oil
(petroleum). These fractions are obtained from the distillation process as liquids, but are re-vaporized before cracking.
Catalytic cracking
Modern cracking uses zeolites as the catalyst to give high percentages of hydrocarbons with between 5 and 10 carbon atoms -
particularly useful for petrol (gasoline).
In thermal cracking, high temperatures (typically in the range of 450°C to 750°C) and pressures (up to about 70 atmospheres) are
used to break the large hydrocarbons into smaller ones. Thermal cracking gives mixtures of products containing high proportions of
hydrocarbons with double bonds - alkenes.