1/16/2020 How Benzene is Made

How to Convert an Alkane to an Alkene

•••

Updated April 20, 2018 By Claire Gillespie

An alkene represents an unsaturated hydrocarbon with double bonds, while an alkane

is a saturated hydrocarbon with only single bonds. To convert an alkane to an alkene,
requires that you remove hydrogen from the alkane molecule at extremely high
temperatures. This process is known as dehydrogenation.

TL;DR (Too Long; Didn't Read)

Converting an alkane hydrocarbon to an alkene involves dehydrogenation, an
endothermic process in which hydrogen is removed from the alkane molecule.

Properties of Alkanes
Alkanes are hydrocarbons, which means they contain only carbon and hydrogen
atoms. As saturated hydrocarbons, alkanes contain hydrogen in every available place.
This makes them fairly non-responsive, apart from when they react to and with
oxygen in the air (called burning or combustion). Alkanes contain only single bonds
and have similar chemical properties to each other and trends in physical properties.

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For example, as the molecular chain length grows, their boiling point increases.
Examples of alkanes include methane, ethane, propane, butane and pentane. Alkanes
are extremely combustible and useful as clean fuels, burning to produce water and
carbon dioxide.

Properties of Alkenes
Alkenes are also hydrocarbons, but they are unsaturated, meaning they contain
carbon-carbon double bonds, for example, there are one or more double bonds
between carbon atoms in the molecule. This makes them more reactive than alkanes.
Examples of alkenes include ethene, propene, but-1-ene and but-2-ene. Alkenes are
precursors to aldehydes, polymers, aromatics and alcohols. By adding steam to an
alkene, it becomes an alcohol.

Converting Alkenes to Alkanes

To convert an alkene to an alkane, you must break the double bond by adding
hydrogen to an alkene in the presence of a nickel catalyst, at a temperature of around
302 degrees Fahrenheit or 150 degrees Celsius, a process known as hydrogenation.

Converting Alkanes to Alkenes

Alkanes, like propane and isobutane become alkenes like propylene and isobutylene
through a chemical process called dehydrogenation, the removal of hydrogen, and the
reverse of hydrogenation.The petrochemical industry often uses this process to create
aromatics and styrene. The process is highly endothermic and requires temperatures
of 932 degrees F, 500 degrees C and above.

Common dehydrogenation processes include aromatization, in which chemists

aromatize cyclohexene in the presence of hydrogenation acceptors using the
elements sulfur and selenium, and the dehydrogenation of amines to nitriles using a
reagent like iodine pentafluoride. Dehydrogenation processes can also convert
saturated fats to unsaturated fats in the manufacturing of margarine and other foods.
The chemical reactions during dehydrogenation are possible at high temperatures
because the release of hydrogen gas increases the collapse of the system.

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How Benzene is Made

How Benzene is Made

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1/16/2020 How Benzene is Made

•••

Updated April 24, 2017 By Eric Bank, MBA, MS Finance

Benzene is the simplest hydrocarbon belonging to the class of organic compounds

known as aromatics. Its formula, C6H6, reflects its ring structure, in which all six
carbon atoms share electrons equally and the carbon-to-carbon linkages are
intermediate between single and double bonds. At room temperature, benzene is a
colorless liquid with the smell of 'sweet gasoline'. Benzene boils at 176.2 degrees
Fahrenheit and freezes below 41.9 degrees Fahrenheit. Benzene is a dangerous
chemical that is highly flammable and carcinogenic. It occurs naturally as a component
of crude oil, and there are several ways to prepare it.

Cracking Crude Oil

Preparing benzene from crude oil using heat is called cracking. Cracking is a multistep
process in which a facility vaporizes raw petroleum, adds steam and then briefly
passes the gaseous mixture through a furnace at temperatures between 1,300 and
1,650 degrees Fahrenheit. The resulting mixture of hydrocarbons is called raw
pyrolysis gas. Solvents, usually alcohols, then extract benzene and other aromatic
compounds, including methylbenzene. Finally, the dissolved compounds undergo
fractional distillation, which separates out the different components, including
benzene.

Reforming Naphtha
Naphtha refers to straight-chain, or aliphatic, hydrocarbons containing 5–10 carbon
atoms. Naphtha is derived primarily from petroleum and natural gas. To reform

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naphtha into benzene, reactors must first remove any sulfurous impurities and then
mix the naphtha with hydrogen at 930 degrees Fahrenheit, a process called
hydroforming. The gas passes over a catalyst, such as platinum or rhenium, under 5
atmospheres of pressure. This process converts aliphatic hydrocarbons to their
corresponding aromatic compounds. Benzene, formed from the six-carbon aliphatic
compound hexane, and the other hydrocarbons are then dissolved and distilled to
separate the different compounds.

Toluene Dispropotionation
Methylbenzene, also known as toluene, is a byproduct of naphtha reformation but is
of limited commercial value. Processing plants can convert toluene into the more
valuable hydrocarbons benzene and xylene. A toluene-hydrogen mixture passes over
a catalyst—usually zeolite, a mineral containing aluminosilicates—under conditions of
15–25 atmospheres of pressure and 800–900 degrees Fahrenheit. Equipment then
distills the resulting hydrocarbon mixture to separate the benzene, toluene and
xylene fractions. The toluene is recycled for further disproportionation.

Toluene Hydrodealkylation
An alternative method to prepare benzene from toluene is hydrodealkylation.
Reactors compress toluene and hydrogen to pressures between 20 and 60
atmospheres and heat the mixture to temperatures between 930 and 1,220 degrees
Fahrenheit. In the presence of a catalyst, a reaction converts the mixture to benzene
and methane. Suitable catalysts include chromium, molybdenum and platinum. The
leftover hydrogen is recycled, and the benzene is separated out by distillation. This
method results in a conversion rate of 90 percent.

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Chemical Formula for Propane

Chemical Formula for Propane

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•••

Updated October 25, 2018 By A.P. Mentzer

Propane is a fossil fuel and a component of natural gas. Over millions of years it
formed from the organic remains of organisms and is mined from underground
deposits. Propane gas is an organic compound made of three molecules of carbon
atoms bonded with eight hydrogen atoms. The type of carbon-carbon carbon-
hydrogen bonds determines the structure of propane molecules, which follows the
same pattern as other types of natural gasses like methane and butane.

TL;DR (Too Long; Didn't Read)

TL;DR (Too Long; Didn't Read)
The chemical formula of propane is C3H8.

Propane Classification
Propane is classified as an organic compound because it contains carbon. It is further
categorized as a hydrocarbon because it belongs to a group of organic compounds
that are made of only carbon and hydrogen. More specifically, propane is a type of
hydrocarbon called an alkane. The atoms in alkane molecules are held together by
single covalent bonds, and carbon atoms always form four covalent bonds.

Chemical Formula of Propane

Alkanes follow a general formula with a set ratio of carbon atoms to hydrogen atoms:
C_nH2_n+2. The simplest alkane is methane, otherwise known as natural gas. It
contains one carbon atom bonded to four hydrogen atoms. For methane, n = 1, so the
number of hydrogen atoms it has is equal to 2(1)+2 which equals 4. Ethane contains
two carbon atoms bonded together, and each carbon is bonded to three hydrogen
atoms for a total of six hydrogen atoms. Propane has chain of three carbon atoms,
with a chemical formula of C3H8, because a chain of three carbons require 2(3)+2
hydrogen atoms, which equals eight. Butane, another common alkane used as fuel in
hand-held gas torches, has four carbon atoms bonded with ten hydrogen atoms, with a
chemical formula of C4H10.

Propane Structure
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Alkanes can be structured as either straight chain or branched chain. Propane is a

straight-chain alkane, with the carbon atoms structured C-C-C. The middle carbon
shares one bond with each of the end carbons and has two hydrogen atoms. The end
carbons each share a bond with the central carbon atom and are each bonded with
three hydrogen atoms. In terms of individual carbon atoms, propane can be expressed
as CH3CH2CH3, which is equivalent to C3H8 but makes propane's structure more
explicit.

Properties of Propane
In addition to the structural similarities shared by straight-chain alkanes, they also
share similar properties. Propane and other hydrocarbons are non-polar. This
property dictates that they can only mix with other non-polar substances. For
example, oils and other fuels are made from a mixture of hydrocarbons. They will not
mix with a polar substance such as water; the attraction between the molecules
makes oil and water separate. With straight-chain alkanes, boiling point and melting
point increase as the number of carbon molecules increases. The propane boiling
point is −44 degrees Fahrenheit (−42 degrees Celsius) and the melting of −306
degrees Fahrenheit ( −189 degrees Celsius). Methane, with only one carbon, has a
lower boiling point than propane at −164 degrees Celsius. Octane has eight carbons
and a boiling point of 98 degrees Celsius.

Uses of Propane
Because of its low boiling point, propane is normally found in its gaseous state. When
the correct amount of pressure and temperature are applied to propane, it goes
through a process called liquefaction that forces propane gas into its liquid state.
Propane can be stored as a liquid in pressurized tanks well above its boiling point.
Liquified propane gas is used as a heating fuel that is burned to power furnaces and
hot water heaters. It is also used as a cooking fuel for outdoor gas grills and gas-
powered camping cooking stoves. Propane gas is also a component in propellants used
in aerosol cans. Propane is also used as a component in some types of adhesives,
sealants and paint.

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