Propylene

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Propylene

Propene, also known as propylene, is an unsaturated

Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
organic compound

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
having the chemical formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
C

Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
₃H

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
₆. It has one double bond

Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds....
, and is the second simplest member of the alkene

Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
class of hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
s, and it is also second in natural abundance.

oom temperature

Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
, propene is a colourless, odourless gas, though when used as a fuel, it is mixed with minute quantities of foul-smelling sulfurous compounds (mercaptans) so that gas leaks can be readily detected.

Propene has a higher density and boiling point than ethylene

Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
due to its greater size.

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Properties

At room temperature

Temperature

Ethylene

Volatility (chemistry)

Volatility in the context of chemistry, physics and thermodynamics is a measure of the tendency of a substance to vaporize. It has also been defined as a measure of how readily a substance vaporizes....
. It lacks strongly polar bond

Polar bond

Polar bond may refer to:Polar bond* Chemical polarity* Covalent bond* Bond dipole moment* Partial charge* Dipoles#Molecular dipoles* Electronegativity...
s, yet the molecule has a small dipole moment

Dipole moment

Dipole moment refers to the quality of a system to behave like a dipole. Dipole moment is the measured polarity of a polar covalent bond. It is defined as the product magnitude of charge on the atoms and the distance between the two bonded atoms....
due to its reduced symmetry (its point group

Point group

In mathematics, a point group is a group of geometric symmetry leaving a point fixed....
is C_s

Point groups in three dimensions

In geometry, a point group in three dimensions is an isometry group in three dimensions that leaves the origin fixed, or correspondingly, an isometry group of a sphere....
).

Propene has the same empirical formula as cyclopropane

Cyclopropane

Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms....
but their atoms are connected in different ways, making these molecules structural isomers.

Synthesis

All propene is obtained from non-renewable sources; petroleum

Petroleum

Petroleum or crude oil is a naturally occurring, flammable liquid found in rock formations in the Earth consisting of a complex mixture of hydrocarbons of various molecular weights, plus other organic compounds....
or natural gas

Natural gas

Natural gas is a gas consisting primarily of methane. It is found associated with fossil fuels, in coal beds, as methane clathrates, and is created by methanogenic organisms in marshes, bogs, and landfills....
deposits (and coal to a lesser extent). It is a fossil fuel

Fossil fuel

Fossil fuels or mineral fuels are fossil source fuels, that is, carbon or hydrocarbons found in the earth?s Crust .Fossil fuel range from volatile materials with low carbon:hydrogen ratios like methane, to liquid petroleum to nonvolatile materials composed of almost pure carbon, like anthracite coal....
. Propene is extracted from these by fractional distillation during oil refining, but demand exceeds supply so most is manufactured by cracking

Cracking

Cracking may refer to:* Cracking, the formation of a fracture or partial fracture in a solid material* Fluid catalytic cracking, a catalytic process widely used in oil refineries for cracking large hydrocarbon molecules into smaller molecules...
. The products from this process contain a mixture of products and the propene is separated from the other products by fractional distillation

Fractional distillation

Fractional distillation is the separation of a mixture into its component parts, or fractions, such as in separating chemical compound by their boiling point by heating them to a temperature at which several fractions of the compound will evaporate....
.

Production and Uses

Propene is the raw material for the production of polypropylene

Polypropylene

Polypropylene or polypropene is a thermoplastic polymer, made by the chemical industry and used in a wide variety of applications, including packaging, textiles , stationery, plastic parts and reusable containers of various types, laboratory equipment, loudspeakers, automotive components, and polymer banknotes....
, a versatile polymer

Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
widely used in several different grades for packaging. Most propene is polymerized using Ziegler-Natta catalysis

Ziegler-Natta catalyst

A Ziegler-Natta catalyst is a reagent or a mixture of reagents used in the production of polymers of 1-alkenes . Ziegler-Natta catalysts are typically based on titanium compounds and organometallic chemistry aluminium compounds, for example triethylaluminium, 3Al....
, which produces isotactic

Tacticity

Tacticity is the relative stereochemistry of adjacent chirality centers within a macromolecule . The practical significance of tacticity rests in the link between tacticity and the physical properties of the polymer....
polypropylene. Along with benzene

Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, propene is a key feedstock in the cumene process

Cumene process

Cumene process is an industrial process for developing phenol and acetone from benzene and propylene. The term stems from cumene , the intermediate material during the process....
, a reaction carried out on industrial scales to produce acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
and phenol

Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
. Propene is also used during the production of many other chemical products such as isopropanol (propan-2-ol), acrylonitrile

Acrylonitrile

Acrylonitrile is the chemical compound with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities....
, and propylene oxide

Propylene oxide

Propylene oxide is a highly toxic flammable chemical compound. It is an epoxide having a molecular formula C3H6O. Other names include methyloxirane and 1,2-epoxypropane....
(epoxypropane).

The production of propene has remained static at around 35 million tonnes (Europe and North America only) from 2000 – 2008 but has been increasing in East Asia, most notably Singapore and China.Total world production of propene is currently about half that of ethylene

Ethylene

Reactivity

Propene resembles other alkenes in that it undergoes addition

Electrophilic addition

In organic chemistry, an electrophilic addition reaction is an addition reaction where, in a chemical compound, a pi bond is removed by the creation of two new covalent bonds....
reactions relatively easily at room temperature. The relative weakness of its double bond (which is less strong than two single bonds) explains its tendency to react with substances that can achieve this transformation.