Ethylene (
IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name: ethene) is a
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
which has the formula or . It is a colourless,
flammable
A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...
gas with a faint "sweet and
musk
Musk (Persian: مشک, ''Mushk'') is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial sub ...
y" odour when pure.
[ It is the simplest ]alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
(a hydrocarbon with carbon-carbon double bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
s).
Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonne
The tonne ( or ; symbol: t) is a unit of mass equal to 1000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton to distinguish it from the non-metric units of the short ton ( United State ...
s in 2016) exceeds that of any other organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
. Much of this production goes toward polyethylene
Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
, a widely used plastic
Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...
containing polymer
A polymer (; Greek '' poly-'', "many" + ''-mer'', "part")
is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
chains of ethylene units in various chain lengths. Ethylene is also an important natural plant hormone
Plant hormone (or phytohormones) are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, from embryogenesis, the regulation of organ size, pa ...
and is used in agriculture to force the ripening of fruits. The hydrate
In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...
of ethylene is ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
.
Structure and properties
This hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
has four hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
atom
Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons.
Every solid, liquid, gas, and ...
s bound to a pair of carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
atoms that are connected by a double bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
. All six atoms that comprise ethylene are coplanar
In geometry, a set of points in space are coplanar if there exists a geometric plane that contains them all. For example, three points are always coplanar, and if the points are distinct and non-collinear, the plane they determine is unique. Howe ...
. The H-C-H angle
In Euclidean geometry, an angle is the figure formed by two Ray (geometry), rays, called the ''Side (plane geometry), sides'' of the angle, sharing a common endpoint, called the ''vertex (geometry), vertex'' of the angle.
Angles formed by two ...
is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively weak: rotation about the C-C bond is a very low energy process that requires breaking the π-bond by supplying heat at 50°C.
The π-bond in the ethylene molecule is responsible for its useful reactivity. The double bond is a region of high electron density
In quantum chemistry, electron density or electronic density is the measure of the probability of an electron being present at an infinitesimal element of space surrounding any given point. It is a scalar quantity depending upon three spatial va ...
, thus it is susceptible to attack by electrophiles
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carri ...
. Many reactions of ethylene are catalyzed by transition metals, which bind transiently to the ethylene using both the π and π* orbitals.
Being a simple molecule, ethylene is spectroscopically simple. Its UV-vis spectrum
A spectrum (plural ''spectra'' or ''spectrums'') is a condition that is not limited to a specific set of values but can vary, without gaps, across a continuum. The word was first used scientifically in optics to describe the rainbow of colors i ...
is still used as a test of theoretical methods.
Uses
Major industrial reactions of ethylene include in order of scale: 1) polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...
, 2) oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
, 3) halogenation
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, ...
and hydrohalogenation, 4) alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
, 5) hydration Hydration may refer to:
* Hydrate, a substance that contains water
* Hydration enthalpy, energy released through hydrating a substance
* Hydration reaction, a chemical addition reaction where a hydroxyl group and proton are added to a compound
* ...
, 6) oligomerization
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
, and 7) hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon d ...
. In the United States
The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...
and Europe
Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a Continent#Subcontinents, subcontinent of Eurasia ...
, approximately 90% of ethylene is used to produce ethylene oxide
Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered Ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless a ...
, ethylene dichloride
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...
, ethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermedia ...
and polyethylene
Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
. Most of the reactions with ethylene are electrophilic addition
In organic chemistry, an electrophilic addition reaction is an addition reaction where a chemical compound containing a double or triple bond has a π bond broken, with the formation of two new σ bonds.March, Jerry; (1985). Advanced Organic Che ...
.
Polymerization
Polyethylene consumes more than half of the world's ethylene supply. Polyethylene, also called ''polyethene'' and ''polythene'', is the world's most widely used plastic. It is primarily used to make films in packaging
Packaging is the science, art and technology of enclosing or protecting products for distribution, storage, sale, and use. Packaging also refers to the process of designing, evaluating, and producing packages. Packaging can be described as a co ...
, carrier bags
Plastic shopping bags, carrier bags, or plastic grocery bags are a type of plastic bag used as shopping bags and made from various kinds of plastic. In use by consumers worldwide since the 1960s, these bags are sometimes called single-use bags, ...
and trash liners
"Liners" is a horticultural term referring to very young plants, usually grown for sale to retailers or wholesalers, who then grow them to a larger size before selling them to consumers. Liners are usually grown from seed, but may also be grown ...
. Linear alpha-olefins
In organic chemistry, alpha-olefins (or α-olefins) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary or alpha (α) position.''Petrochemical ...
, produced by oligomerization
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
(formation of short polymers) are used as precursors, detergents, plasticisers, synthetic lubricants
Synthetic oil is a lubricant consisting of chemical compounds that are artificially modified or synthesised. Synthetic lubricants can be manufactured using chemically modified petroleum components rather than whole crude oil, but can also be syn ...
, additives, and also as co-monomers in the production of polyethylenes.
Oxidation
Ethylene is oxidized
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
to produce ethylene oxide
Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered Ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless a ...
, a key raw material in the production of surfactant
Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...
s and detergent
A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more ...
s by ethoxylation
Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.
In the usual application, alcohols and phenols are converted in ...
. Ethylene oxide is also hydrolyzed to produce ethylene glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...
, widely used as an automotive antifreeze as well as higher molecular weight glycols, glycol ethers
Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while h ...
, and polyethylene terephthalate
Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods ...
.
Ethylene undergoes oxidation by palladium to give acetaldehyde
Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
. This conversion remains a major industrial process (10M kg/y). The process proceeds via the initial complexation of ethylene to a Pd(II) center.
Halogenation and hydrohalogenation
Major intermediates from the halogenation
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, ...
and hydrohalogenation of ethylene include ethylene dichloride
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...
, ethyl chloride
Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet ...
, and ethylene dibromide
1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula . Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a ...
. The addition of chlorine entails "oxychlorination In organic chemistry, oxychlorination is a process for making C-Cl bonds. In contrast with direct use of Cl2, oxychlorination uses hydrogen chloride in combination with oxygen.{{Ullmann, author=M. Rossberg , display-authors=et al., title=Chlorinated ...
", i.e. chlorine itself is not used. Some products derived from this group are polyvinyl chloride, trichloroethylene
The chemical compound trichloroethylene is a halocarbon commonly used as an industrial solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell. It should not be confused with the similar 1,1,1-trichloroethane, ...
, perchloroethylene
Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (and abbreviations such as "perc" or "PERC", and "PCE"), is a chlorocarbon with the formula Cl2C=CCl2 . It is a colorless li ...
, methyl chloroform
The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protoc ...
, polyvinylidene chloride
Polyvinylidene chloride, or polyvinylidene dichloride (PVDC), is a homopolymer of vinylidene chloride.
History
Ralph Wiley accidentally discovered polyvinylidene chloride polymer in 1933. He, then, was a college student who worked part-time at D ...
and copolymer
In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
s, and ethyl bromide
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor.
Prepara ...
.[
]
Alkylation
Major chemical intermediates from the alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
with ethylene is ethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermedia ...
, precursor to styrene
Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...
. Styrene is used principally in polystyrene
Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It is a ...
for packaging and insulation, as well as in styrene-butadiene
Styrene-butadiene or styrene-butadiene rubber (SBR) describe families of synthetic rubbers derived from styrene and butadiene (the version developed by Goodyear is called Neolite). These materials have good abrasion resistance and good aging st ...
rubber for tires and footwear. On a smaller scale, ethyltoluene
4-Ethyltoluene is an organic compound with the formula CH3C6H4C2H5. It is one of three isomers of ethyltoluene, the other two isomers being 3-ethyltoluene and 2-ethyltoluene. All are colorless liquids and all are used for the production of speci ...
, ethylanilines, 1,4-hexadiene, and aluminium
Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. I ...
alkyls. Products of these intermediates include polystyrene
Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It is a ...
, unsaturated polyester
Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...
s and ethylene-propylene terpolymers.[
]
Oxo reaction
The hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon d ...
(oxo reaction) of ethylene results in propionaldehyde
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.
Production
Propionalde ...
, a precursor to propionic acid
Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a liq ...
and n-propyl alcohol.[
]
Hydration
Ethylene has long represented the major nonfermentative precursor to ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
. The original method entailed its conversion to diethyl sulfate
Diethyl sulfate (DES) is a highly toxic, combustible, and likely carcinogenic chemical compound with the formula (C2H5)2SO4. It occurs as a colorless, oily liquid with a faint peppermint odor and is corrosive to tissue and metals. Diethyl sulfate ...
, followed by hydrolysis. The main method practiced since the mid-1990s is the direct hydration of ethylene catalyzed by solid acid catalyst
In acid catalysis and base catalysis, a chemical reaction is catalyzed by an acid or a base. By Brønsted–Lowry acid–base theory, the acid is the proton (hydrogen ion, H+) donor and the base is the proton acceptor. Typical reactions catalyze ...
s:
:C2H4 + H2O → CH3CH2OH
Dimerization to butenes
Ethylene is dimerized by hydrovinylation
In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene (). The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reactio ...
to give ''n''-butenes using processes licensed by Lummus or IFP. The Lummus process produces mixed ''n''-butenes (primarily 2-butene
But-2-ene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting ''cis''/''trans''-isomerism (also known as (''E''/''Z'')-isomerism); that is, it exists as two geometric isomers ''cis''-but-2-ene ((''Z'')-but-2-ene) and ...
s) while the IFP process produces 1-butene. 1-Butene is used as a comonomer In polymer chemistry, a comonomer refers to a polymerizable precursor to a copolymer aside from the principal monomer. In some cases, only small amounts of a comonomer are employed, in other cases substantial amounts of comonomers are used. Furthe ...
in the production of certain kinds of polyethylene
Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
.
Fruit and flowering
Ethylene is a hormone that affects the ripening and flowering of many plants. It is widely used to control freshness in horticulture
Horticulture is the branch of agriculture that deals with the art, science, technology, and business of plant cultivation. It includes the cultivation of fruits, vegetables, nuts, seeds, herbs, sprouts, mushrooms, algae, flowers, seaweeds and no ...
and fruit
In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering.
Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in particu ...
s. The scrubbing of naturally occurring ethylene delays ripening.
Niche uses
An example of a niche use is as an anesthetic agent
Anesthesia is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia (relief from or prevention of pain), paralysis (muscle relaxation), am ...
(in an 85% ethylene/15% oxygen ratio). Another use is as a welding gas.
Production
Global ethylene production was 107 million tonnes in 2005, 109 million tonnes in 2006, 138 million tonnes in 2010, and 141 million tonnes in 2011. By 2013, ethylene was produced by at least 117 companies in 32 countries. To meet the ever-increasing demand for ethylene, sharp increases in production facilities are added globally, particularly in the Mideast
The Middle East ( ar, الشرق الأوسط, ISO 233: ) is a geopolitical region commonly encompassing Arabian Peninsula, Arabia (including the Arabian Peninsula and Bahrain), Anatolia, Asia Minor (Asian part of Turkey except Hatay Pro ...
and in China
China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's most populous country, with a population exceeding 1.4 billion, slightly ahead of India. China spans the equivalent of five time zones and ...
.
Industrial process
Ethylene is produced by several methods in the petrochemical industry
The petrochemical industry is concerned with the production and trade of petrochemicals. A major part is constituted by the plastics (polymer) industry. It directly interfaces with the petroleum industry, especially the downstream sector.
Compan ...
. A primary method is steam cracking (SC) where hydrocarbons and steam are heated to 750–950 °C. This process converts large hydrocarbons into smaller ones and introduces unsaturation. When ethane
Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petr ...
is the feedstock, ethylene is the product. Ethylene is separated from the resulting mixture by repeated compression
Compression may refer to:
Physical science
*Compression (physics), size reduction due to forces
*Compression member, a structural element such as a column
*Compressibility, susceptibility to compression
* Gas compression
*Compression ratio, of a ...
and distillation
Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...
. In Europe and Asia, ethylene is obtained mainly from cracking naphtha, gasoil and condensates with the coproduction of propylene, C4 olefins and aromatics (pyrolysis gasoline). Other technologies employed for the production of ethylene include oxidative coupling of methane
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate (chemistry), substrate change. Oxidation is the loss of Electron, electrons or an increase in the oxidation state, while reduction ...
, Fischer-Tropsch synthesis, methanol-to-olefins (MTO), and catalytic dehydrogenation.
Laboratory synthesis
Although of great value industrially, ethylene is rarely synthesized in the laboratory and is ordinarily purchased. It can be produced via dehydration of ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
with sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
or in the gas phase with aluminium oxide.
Biosynthesis
Ethylene is produced from methionine
Methionine (symbol Met or M) () is an essential amino acid in humans. As the precursor of other amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine plays a critical ro ...
in nature. The immediate precursor is 1-aminocyclopropane-1-carboxylic acid.
Ligand
is a well-studied complex of ethylene.">Chlorobis(ethylene)rhodium dimer is a well-studied complex of ethylene.
Ethylene is a fundamental ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electr ...
in transition metal alkene complexes. One of the first organometallic compounds, Zeise's salt
Zeise's salt, potassium trichloro(ethylene)platinate(II), is the chemical compound with the formula K platinum">PtCl3(C2H4).html" ;"title="platinum.html" ;"title="/nowiki>PtCl3(C2H4)">platinum.html"_;"title="/nowiki>platinum">PtCl3(C2H4)H2O.__Th ...
is a complex of ethylene. Useful reagents containing ethylene include Pt(PPh3)2(C2H4) and Rh2Cl2(C2H4)4. The Rh-catalysed hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon d ...
of ethylene is conducted on industrial scale to provide propionaldehyde
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.
Production
Propionalde ...
.
History
Some geologists and scholars believe that the famous Greek Oracle at Delphi
Delphi (; ), in legend previously called Pytho (Πυθώ), in ancient times was a sacred precinct that served as the seat of Pythia, the major oracle who was consulted about important decisions throughout the ancient classical world. The oracle ...
(the Pythia
Pythia (; grc, Πυθία ) was the name of the high priestess of the Temple of Apollo (Delphi), Temple of Apollo at Delphi. She specifically served as its oracle and was known as the Oracle of Delphi. Her title was also historically glossed i ...
) went into her trance-like state as an effect of ethylene rising from ground faults.
Ethylene appears to have been discovered by Johann Joachim Becher
Johann Joachim Becher (; 6 May 1635 – October 1682) was a German physician, alchemist, precursor of chemistry, scholar and adventurer, best known for his development of the phlogiston theory of combustion, and his advancement of Austrian cameral ...
, who obtained it by heating ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
with sulfuric acid; he mentioned the gas in his ''Physica Subterranea'' (1669). Joseph Priestley
Joseph Priestley (; 24 March 1733 – 6 February 1804) was an English chemist, natural philosopher, separatist theologian, grammarian, multi-subject educator, and liberal political theorist. He published over 150 works, and conducted exp ...
also mentions the gas in his ''Experiments and observations relating to the various branches of natural philosophy: with a continuation of the observations on air'' (1779), where he reports that Jan Ingenhousz
Jan (or John) Ingenhousz or Ingen-Housz FRS (8 December 1730 – 7 September 1799) was a Dutch-born British physiologist, biologist and chemist.
He is best known for discovering photosynthesis by showing that light is essential to the process ...
saw ethylene synthesized in the same way by a Mr. Enée in Amsterdam in 1777 and that Ingenhousz subsequently produced the gas himself. The properties of ethylene were studied in 1795 by four Dutch
Dutch commonly refers to:
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* Dutch people ()
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Dutch may also refer to:
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* Pennsylvania Dutch Country
People E ...
chemists, Johann Rudolph Deimann, Adrien Paets van Troostwyck, Anthoni Lauwerenburgh and Nicolas Bondt, who found that it differed from hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
gas and that it contained both carbon and hydrogen. This group also discovered that ethylene could be combined with chlorine
Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
to produce the ''oil of the Dutch chemists'', 1,2-dichloroethane
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...
; this discovery gave ethylene the name used for it at that time, ''olefiant gas'' (oil-making gas.) The term olefiant gas is in turn the etymological origin of the modern word "olefin", the class of hydrocarbons in which ethylene is the first member.
In the mid-19th century, the suffix ''-ene'' (an Ancient Greek root added to the end of female names meaning "daughter of") was widely used to refer to a molecule or part thereof that contained one fewer hydrogen atoms than the molecule being modified. Thus, ''ethylene'' () was the "daughter of ethyl
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* Ethyl group, an organic chemistry moiety
* Ethyl alcohol (or ethanol)
* E ...
" (). The name ethylene was used in this sense as early as 1852.
In 1866, the German
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chemist August Wilhelm von Hofmann
August Wilhelm von Hofmann (8 April 18185 May 1892) was a German chemist who made considerable contributions to organic chemistry. His research on aniline helped lay the basis of the aniline-dye industry, and his research on coal tar laid the g ...
proposed a system of hydrocarbon nomenclature in which the suffixes -ane, -ene, -ine, -one, and -une were used to denote the hydrocarbons with 0, 2, 4, 6, and 8 fewer hydrogens than their parent alkane
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...
. In this system, ethylene became ''ethene''. Hofmann's system eventually became the basis for the Geneva nomenclature approved by the International Congress of Chemists in 1892, which remains at the core of the IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
nomenclature. However, by that time, the name ethylene was deeply entrenched, and it remains in wide use today, especially in the chemical industry.
Following experimentation by Luckhardt, Crocker, and Carter at the University of Chicago, ethylene was used as an anesthetic. It remained in use through the 1940s use even while chloroform was being phased out. Its pungent odor and its explosive nature limit its use today.
Nomenclature
The 1979 IUPAC nomenclature rules made an exception for retaining the non-systematic name ''ethylene''; however, this decision was reversed in the 1993 rules, and it remains unchanged in the newest 2013 recommendations, so the IUPAC name is now ''ethene''. In the IUPAC system, the name ''ethylene'' is reserved for the divalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with other atoms when it forms chemical compounds or molecules.
Description
The combining capacity, or affinity of an ...
group -CH2CH2-. Hence, names like ''ethylene oxide'' and ''ethylene dibromide'' are permitted, but the use of the name ''ethylene'' for the two-carbon alkene is not. Nevertheless, use of the name ''ethylene'' for H2C=CH2 (and propylene for H2C=CHCH3) is still prevalent among chemists in North America.
Safety
Like all hydrocarbons, ethylene is a combustible asphyxiant
An asphyxiant gas, also known as a simple asphyxiant, is a nontoxic or minimally toxic gas which reduces or displaces the normal oxygen concentration in breathing air. Breathing of oxygen-depleted air can lead to death by asphyxiation (suffocation) ...
. It is listed as an IARC IARC may refer to:
* International Aerial Robotics Competition
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The Israel Amateur Radio Club (IA ...
class 3 carcinogen, since there is no current evidence that it causes cancer in humans.
See also
* RediRipe, an ethylene detector in fruit.
References
External links
International Chemical Safety Card 0475
MSDS
{{Authority control
Alkenes
General anesthetics
Monomers
Commodity chemicals
Petrochemicals
Industrial gases
Organic compounds with 2 carbon atoms