Ethylene

Not to be confused with ethane or ethyne.

Ethylene

Names
IUPAC name Ethene
Identifiers
CAS Number	74-85-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18153 Y
ChEMBL	ChEMBL117822 Y
ChemSpider	6085 Y
ECHA InfoCard	100.000.742
EC Number	200-815-3
KEGG	C06547 Y
PubChem CID	6325
UNII	91GW059KN7 Y
InChI InChI=1S/C2H4/c1-2/h1-2H2 Y Key: VGGSQFUCUMXWEO-UHFFFAOYSA-N Y InChI=1/C2H4/c1-2/h1-2H2 Key: VGGSQFUCUMXWEO-UHFFFAOYAE
SMILES C=C
Properties
Chemical formula	C 2H 4
Molar mass	7001280540000000000♠28.054 g·mol−1
Appearance	colorless gas
Density	1.178 kg/m3 at 15 °C, gas[1]
Melting point	−169.2 °C (−272.6 °F; 104.0 K)
Boiling point	−103.7 °C (−154.7 °F; 169.5 K)
Solubility in water	3.5 mg/100 mL (17 °C);[citation needed] 2.9 mg/L[2]
Solubility in ethanol	4.22 mg/L[2]
Solubility in diethyl ether	good[2]
Acidity (pKa)	44
Conjugate acid	Ethenium
Magnetic susceptibility (χ)	-15.30·10−6 cm3/mol
Structure
Molecular shape	D2h
Dipole moment	zero
Thermochemistry
Std molar entropy (So298)	219.32 J·K−1·mol−1
Std enthalpy of formation (ΔfHo298)	+52.47 kJ/mol
Hazards
Safety data sheet	See: data page ICSC 0475
EU classification (DSD) (outdated)	F+
R-phrases (outdated)	R12 R67
S-phrases (outdated)	(S2) S9 S16 S33 S46
NFPA 704	4 2 2
Flash point	−136 °C (−213 °F; 137 K)
Autoignition temperature	542.8 °C (1,009.0 °F; 815.9 K)
Related compounds
Related compounds	Ethane Acetylene Propene
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula C
₂H
₄ or H₂C=CH₂. It is a colorless flammable gas with a faint "sweet and musky" odour when pure.^[4] It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).

Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016^[5]) exceeds that of any other organic compound.^[6][7] Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths. Ethylene is also an important natural plant hormone and is used in agriculture to force the ripening of fruits.^[8] Ethylene's hydrate is ethanol.

Contents

• 
  1 Structure and properties
  


• 
  2 Uses
  
  
  
  • 
    2.1 Polymerization
    
  
  
  • 
    2.2 Oxidation
    
  
  
  • 
    2.3 Halogenation and hydrohalogenation
    
  
  
  • 
    2.4 Alkylation
    
  
  
  • 
    2.5 Oxo reaction
    
  
  
  • 
    2.6 Hydration
    
  
  
  • 
    2.7 Dimerization to butenes
    
  
  
  • 
    2.8 Niche uses
    
  
  
  • 
    2.9 Weapon
    
  
  
  
  


• 
  3 Production
  
  
  
  • 
    3.1 Industrial process
    
  
  
  • 
    3.2 Laboratory synthesis
    
  
  
  
  


• 
  4 Ethylene as a plant hormone
  
  
  
  • 
    4.1 History of ethylene in plant biology
    
  
  
  • 
    4.2 Ethylene biosynthesis in plants
    
  
  
  • 
    4.3 Ethylene perception in plants
    
  
  
  • 
    4.4 Ethylene response to salt stress
    
  
  
  • 
    4.5 Environmental and biological triggers of ethylene
    
  
  
  • 
    4.6 Corolla senescence
    
    
    
    • 
      4.6.1 List of plant responses to ethylene
      
    
    
    • 
      4.6.2 Commercial issues
      
    
    
    
    
  
  
  
  


• 
  5 Ligand
  


• 
  6 History
  
  
  
  • 
    6.1 Nomenclature
    
  
  
  • 
    6.2 Safety
    
  
  
  
  


• 
  7 References
  


• 
  8 Further reading
  


• 
  9 External links
  

Structure and properties

Orbital description of bonding between ethylene and a transition metal.

This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are connected by a double bond. All six atoms that comprise ethylene are coplanar. The H-C-H angle is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively rigid: rotation about the C-C bond is a high energy process that requires breaking the π-bond.

The π-bond in the ethylene molecule is responsible for its useful reactivity. The double bond is a region of high electron density, thus it is susceptible to attack by electrophiles. 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 is still used as a test of theoretical methods.^[9]

Uses

Major industrial reactions of ethylene include in order of scale: 1) polymerization, 2) oxidation, 3) halogenation and hydrohalogenation, 4) alkylation, 5) hydration, 6) oligomerization, and 7) hydroformylation. In the United States and Europe, approximately 90% of ethylene is used to produce ethylene oxide, ethylene dichloride, ethylbenzene and polyethylene.^[10] Most of the reactions with ethylene are electrophilic addition.

Main industrial uses of ethylene. Clockwise from the upper right: its conversions to ethylene oxide, precursor to ethylene glycol; to ethylbenzene, precursor to styrene; to various kinds of polyethylene; to ethylene dichloride, precursor to vinyl chloride.

Polymerization

See also: Ziegler–Natta catalyst and Polyethylene

Polyethylene consumes more than half of the world's ethylene supply. Polyethylene, also called polyethene, is the world's most widely used plastic. It is primarily used to make films in packaging, carrier bags and trash liners. Linear alpha-olefins, produced by oligomerization (formation of short polymers) are used as precursors, detergents, plasticisers, synthetic lubricants, additives, and also as co-monomers in the production of polyethylenes.^[10]

Oxidation

Ethylene is oxidized to produce ethylene oxide, a key raw material in the production of surfactants and detergents by ethoxylation. Ethylene oxide is also hydrolyzed to produce ethylene glycol, widely used as an automotive antifreeze as well as higher molecular weight glycols, glycol ethers and polyethylene terephthalate.

Main article: Wacker process

Ethylene undergoes oxidation by palladium to give acetaldehyde. This conversion remains a major industrial process (10M kg/y).^[11] The process proceeds via the initial complexation of ethylene to a Pd(II) center.

Halogenation and hydrohalogenation

Major intermediates from the halogenation and hydrohalogenation of ethylene include ethylene dichloride, ethyl chloride and ethylene dibromide. The addition of chlorine entails "oxychlorination," i.e. chlorine itself is not used. Some products derived from this group are polyvinyl chloride, trichloroethylene, perchloroethylene, methyl chloroform, polyvinylidene chloride and copolymers, and ethyl bromide.^[12]

Alkylation

Major chemical intermediates from the alkylation with ethylene is ethylbenzene, precursor to styrene. Styrene is used principally in polystyrene for packaging and insulation, as well as in styrene-butadiene rubber for tires and footwear. On a smaller scale, ethyltoluene, ethylanilines, 1,4-hexadiene, and aluminium alkyls. Products of these intermediates include polystyrene, unsaturated polyesters and ethylene-propylene terpolymers.^[12]

Oxo reaction

The hydroformylation (oxo reaction) of ethylene results in propionaldehyde, a precursor to propionic acid and n-propyl alcohol.^[12]

Hydration

Ethylene has long represented the major nonfermentative precursor to ethanol. The original method entailed its conversion to diethyl sulfate, followed by hydrolysis. The main method practiced since the mid-1990s is the direct hydration of ethylene catalyzed by solid acid catalysts:^[13]

C₂H₄ + H₂O → CH₃CH₂OH

Dimerization to butenes

Ethylene is dimerized by hydrovinylation to give n-butenes using processes licensed by Lummus or IFP. The Lummus process produces mixed n-butenes (primarily 2-butenes) while the IFP process produces 1-butene. 1-Butene is used as a comonomer in the production of certain kinds of polyethylene.

Niche uses

An example of a niche use is as an anesthetic agent (in an 85% ethylene/15% oxygen ratio).^[14] It can also be used to hasten fruit ripening, as well as a welding gas.^[10][15]

Weapon

Ethylene can be used in production of sulfur mustard gas, a chemical weapon.

Production

Global ethylene production was 107 million tonnes in 2005,^[6] 109 million tonnes in 2006,^[16] 138 million tonnes in 2010 and 141 million tonnes in 2011.^[17] 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 and in China.^[18]

Industrial process

Ethylene is produced by several methods in the petrochemical industry. 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 is the feedstock, ethylene is the product. Ethylene is separated from the resulting mixture by repeated compression and distillation.^[12] Other technologies employed for the production of ethylene include oxidative coupling of methane, Fischer-Tropsch synthesis, methanol-to-olefins (MTO), and catalytic dehydrogenation.^[19]

Laboratory synthesis

Although of great value industrially, ethylene is rarely synthesized in the laboratory and is ordinarily purchased.^[20]
It can be produced via dehydration of ethanol with sulfuric acid or in the gas phase with aluminium oxide.^[21]

Ethylene as a plant hormone

An ethylene signal transduction pathway. Ethylene permeates the membrane and binds to a receptor on the endoplasmic reticulum. The receptor releases the repressed EIN2. This then activates a signal transduction pathway which activates a regulatory genes that eventually trigger an Ethylene response. The activated DNA is transcribed into mRNA which is then translated into a functional enzyme that is used for ethylene biosynthesis.

Ethylene serves as a hormone in plants.^[22] It acts at trace levels throughout the life of the plant by stimulating or regulating the ripening of fruit, the opening of flowers, and the abscission (or shedding) of leaves.
Commercial ripening rooms use "catalytic generators" to make ethylene gas from a liquid supply of ethanol. Typically, a gassing level of 500 to 2,000 ppm is used, for 24 to 48 hours. Care must be taken to control carbon dioxide levels in ripening rooms when gassing, as high temperature ripening (20 °C; 68 °F)^{[citation needed]} has been seen to produce CO₂ levels of 10% in 24 hours.^[23]

History of ethylene in plant biology

Ethylene has been used since the ancient Egyptians, who would gash figs in order to stimulate ripening (wounding stimulates ethylene production by plant tissues). The ancient Chinese would burn incense in closed rooms to enhance the ripening of pears. In 1864, it was discovered that gas leaks from street lights led to stunting of growth, twisting of plants, and abnormal thickening of stems.^[22] In 1901, a Russian scientist named Dimitry Neljubow showed that the active component was ethylene.^[24] Sarah Doubt discovered that ethylene stimulated abscission in 1917.^[25] Farmers in Florida would commonly get their crops to ripen in sheds by lighting kerosene lamps, which was originally thought to induce ripening from the heat. In 1924, Frank E. Denny discovered that it was the molecule ethylene emitted by the kerosene lamps that induced the ripening.^[26] It was not until 1934 that Gane reported that plants synthesize ethylene.^[27] In 1935, Crocker proposed that ethylene was the plant hormone responsible for fruit ripening as well as senescence of vegetative tissues.^[28]

Ethylene biosynthesis in plants

The Yang cycle

Ethylene is produced from essentially all parts of higher plants, including leaves, stems, roots, flowers, fruits, tubers, and seeds.
Ethylene production is regulated by a variety of developmental and environmental factors. During the life of the plant, ethylene production is induced during certain stages of growth such as germination, ripening of fruits, abscission of leaves, and senescence of flowers. Ethylene production can also be induced by a variety of external aspects such as mechanical wounding, environmental stresses, and certain chemicals including auxin and other regulators.^[29] The pathway for ethylene biosynthesis is named the Yang cycle after the scientist Shang Fa Yang who made key contributions to elucidating this pathway.

Ethylene is biosynthesized from the amino acid methionine to S-adenosyl-L-methionine (SAM, also called Adomet) by the enzyme Met Adenosyltransferase. SAM is then converted to 1-aminocyclopropane-1-carboxylic acid (ACC) by the enzyme ACC synthase (ACS). The activity of ACS determines the rate of ethylene production, therefore regulation of this enzyme is key for the ethylene biosynthesis. The final step requires oxygen and involves the action of the enzyme ACC-oxidase (ACO), formerly known as the ethylene forming enzyme (EFE). Ethylene biosynthesis can be induced by endogenous or exogenous ethylene. ACC synthesis increases with high levels of auxins, especially indole acetic acid (IAA) and cytokinins.

Ethylene perception in plants

Ethylene is perceived by a family of five transmembrane protein dimers such as the ETR1 protein in Arabidopsis. The genes encoding ethylene receptors have been cloned in the reference plant Arabidopsis thaliana and many other plants. Ethylene receptors are encoded by multiple genes in plant genomes. Dominant missense mutations in any of the gene family, which comprises five receptors in Arabidopsis and at least six in tomato, can confer insensitivity to ethylene.^[30]Loss-of-function mutations in multiple members of the ethylene-receptor family result in a plant that exhibits constitutive ethylene responses.^[31]DNA sequences for ethylene receptors have also been identified in many other plant species and an ethylene binding protein has even been identified in Cyanobacteria.^[22]

Ethylene response to salt stress

A large portion of the soil has been affected by over salinity and it has been known to limit the growth of many plants. Globally, the total area of saline soil was 397,000,000 ha and in continents like Africa, it makes up 2 percent of the soil.^[32] The amount of soil salinization has reached 19.5% of the irrigated land and 2.1% of the dry-land agriculture around the world.^[33] Soil salinization affects the plants using osmotic potential by net solute accumulation. The osmotic pressure in the plant is what maintains water uptake and cell turgor to help with stomatal function and other cellular mechanisms.^[33] Over generations, many plant genes have adapted, allowing plants’ phenotypes to change and built different mechanisms to counter salinity effects.

The plant hormone ethylene is a combatant for salinity in most plants. Ethylene is known for regulating plant growth and development and adapted to stress conditions. Central membrane proteins in plants, such as ETO2, ERS1 and EIN2, are used for ethylene signaling in many plant growth processes. ETO2, Ethylene overproducer 2, is a protein that when mutated it will gain a function to continually produce ethylene even when there is no stress condition, causing the plant to grow short and stumpy. ERS1, Ethylene response sensor 1, is activated when ethylene is present in the signaling pathway and when mutated, it loses a function and cannot bind to ethylene. This means a response is never activated and the plant will not be able to cope with the abiotic stress. EIN2, Ethylene insensitive 2, is a protein that activates the pathway and when there is a mutation here the EIN2 will block ethylene stimulation and an ethylene response gene will not be activated. Mutations in these proteins can lead to heightened salt sensitivity and limit plant growth. The effects of salinity have been studied on Arabidopsis plants that have mutated ERS1 and EIN4 proteins.^[34] These proteins are used for ethylene signaling again certain stress conditions, such as salt and the ethylene precursor ACC is allowing suppress of any sensitivity to the salt stress.^[34] Mutations in these pathways can cause lack of ethylene signaling, causing stunt in plant growth and development.

Environmental and biological triggers of ethylene

Environmental cues such as flooding, drought, chilling, wounding, and pathogen attack can induce ethylene formation in plants. In flooding, roots suffer from lack of oxygen, or anoxia, which leads to the synthesis of 1-aminocyclopropane-1-carboxylic acid (ACC). ACC is transported upwards in the plant and then oxidized in leaves. The ethylene produced causes nastic movements (epinasty) of the leaves, perhaps helping the plant to lose water.^[35]

Corolla senescence

The corolla of a plant refers to its set of petals. Corolla development in plants is broken into phases from anthesis to corolla wilting. The development of the corolla is directed in part by ethylene, though its concentration is highest when the plant is fertilized and no longer requires the production or maintenance of structures and compounds that attract pollinators.^[36][37] The role of ethylene in the developmental cycle is as a hormonal director of senescence in corolla tissue. This is evident as ethylene production and emission are maximized in developmental phases post-pollination, until corolla wilting.^[36] Ethylene-directed senescence of corolla tissue can be observed as color change in the corolla or the wilting/ death of corolla tissue. At the chemical level, ethylene mediates the reduction in the amount of fragrance volatiles produced. Fragrance volatiles act mostly by attracting pollinators. Ethylene's role in this developmental scenario is to move the plant away from a state of attracting pollinators, so it also aids in decreasing the production of these volatiles.

Ethylene production in corolla tissue does not directly cause the senescence of corolla tissue, but acts by releasing secondary products that are consistent with tissue aging. While the mechanism of ethylene-mediated senescence are unclear, its role as a senescence-directing hormone can be confirmed by ethylene-sensitive petunia response to ethylene knockdown. Knockdown of ethylene biosynthesis genes was consistent with increased corolla longevity; inversely, up-regulation of ethylene biosynthesis gene transcription factors were consistent with a more rapid senescence of the corolla.^[36]

List of plant responses to ethylene

• Seedling triple response, thickening and shortening of hypocotyl with pronounced apical hook.


• Stimulation of Arabidopsis hypocotyl elongation ^[38]
  


• In pollination, when the pollen reaches the stigma, the precursor of the ethene, ACC, is secreted to the petal, the ACC releases ethylene with ACC oxidase.


• Stimulates leaf senescence
  


• Stimulates senescence of mature xylem cells in preparation for plant use


• Induces leaf abscission
  


• Induces seed germination
  


• Induces root hair growth — increasing the efficiency of water and mineral absorption


• Induces the growth of adventitious roots during flooding


• Stimulates epinasty — leaf petiole grows out, leaf hangs down and curls into itself


• Stimulates fruit ripening
  


• Induces a climacteric rise in respiration in some fruit which causes a release of additional ethylene.


• Affects gravitropism
  


• Stimulates nutational bending


• Inhibits stem growth and stimulates stem and cell broadening and lateral branch growth outside of seedling stage (see Hyponastic response)


• Interference with auxin transport (with high auxin concentrations)


• Inhibits shoot growth and stomatal closing except in some water plants or habitually flooded ones such as some rice varieties, where the opposite occurs (conserving CO
  ₂ and O
  ₂)


• Induces flowering in pineapples
  


• Inhibits short day induced flower initiation in Pharbitus nil^[39] and Chrysanthemum morifolium^[40]
  

Commercial issues

Ethylene shortens the shelf life of many fruits by hastening fruit ripening and floral senescence. Ethylene will shorten the shelf life of cut flowers and potted plants by accelerating floral senescence and floral abscission. Flowers and plants which are subjected to stress during shipping, handling, or storage produce ethylene causing a significant reduction in floral display. Flowers affected by ethylene include carnation, geranium, petunia, rose, and many others.^[41]

Ethylene can cause significant economic losses for florists, markets, suppliers, and growers. Researchers have developed several ways to inhibit ethylene, including inhibiting ethylene synthesis and inhibiting ethylene perception. Aminoethoxyvinylglycine (AVG), Aminooxyacetic acid (AOA), and silver salts are ethylene inhibitors.^[42][43] Inhibiting ethylene synthesis is less effective for reducing post-harvest losses since ethylene from other sources can still have an effect. By inhibiting ethylene perception, fruits, plants and flowers don't respond to ethylene produced endogenously or from exogenous sources. Inhibitors of ethylene perception include compounds that have a similar shape to ethylene, but do not elicit the ethylene response. One example of an ethylene perception inhibitor is 1-methylcyclopropene (1-MCP).

Commercial growers of bromeliads, including pineapple plants, use ethylene to induce flowering. Plants can be induced to flower either by treatment with the gas in a chamber, or by placing a banana peel next to the plant in an enclosed area.

Chrysanthemum flowering is delayed by ethylene gas^[44] and growers have found that carbon dioxide 'burners' and the exhaust fumes from inefficient glasshouse heaters can raise the ethylene concentration to 0.05 ppmv causing delay in flowering of commercial crops.

Ligand

Ethylene is a ligand in organometallic chemistry. One of the first organometallic compounds, Zeise's salt is a complex of ethylene. Useful reagents containing ethylene include Pt(PPh₃)₂(C₂H₄) and Rh₂Cl₂(C₂H₄)₄. The Rh-catalysed hydroformylation of ethylene is conducted on industrial scale to provide propionaldehyde.

History

Some geologists and scholars believe that the famous Greek Oracle at Delphi (the Pythia) went into her trance-like state as an effect of ethylene rising from ground faults.^[45]

Ethylene appears to have been discovered by Johann Joachim Becher, who obtained it by heating ethanol with sulfuric acid;^[46] he mentioned the gas in his Physica Subterranea (1669).^[47]Joseph Priestley 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 saw ethylene synthesized in the same way by a Mr. Enée in Amsterdam in 1777 and that Ingenhousz subsequently produced the gas himself.^[48] The properties of ethylene were studied in 1795 by four Dutch chemists, Johann Rudolph Deimann, Adrien Paets van Troostwyck, Anthoni Lauwerenburgh and Nicolas Bondt, who found that it differed from hydrogen gas and that it contained both carbon and hydrogen.^[49] This group also discovered that ethylene could be combined with chlorine to produce the oil of the Dutch chemists, 1,2-dichloroethane; this discovery gave ethylene the name used for it at that time, olefiant gas (oil-making gas.)^[50]

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 (C
₂H
₄) was the "daughter of ethyl" (C
₂H
₅). The name ethylene was used in this sense as early as 1852.^{[citation needed]}

In 1866, the German chemist August Wilhelm von Hofmann 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.^[51] 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 nomenclature. However, by that time, the name ethylene was deeply entrenched, and it remains in wide use today, especially in the chemical industry.^{[citation needed]}

Following experimentation by Luckhardt, Crocker, and Carter at the University of Chicago,^[52] ethylene was used as an anesthetic.^[53][4] 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.^{[citation needed]}

Nomenclature

The 1979 IUPAC nomenclature rules made an exception for retaining the non-systematic name ethylene,^[54] however, this decision was reversed in the 1993 rules^[55] and remains unchanged in the newest 2013 recommendations^[56] so the IUPAC name is now ethene. Note that in the IUPAC system, the name ethylene is reserved for the divalent 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 is still prevalent among chemists in North America.

Safety

Like all hydrocarbons, ethylene is an asphyxiant and combustible. It is listed as an IARC class 3 carcinogen as there is no evidence at present that it causes cancer in humans.^[57]

References

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12. 
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    ^ Naim Kosaric, Zdravko Duvnjak, Adalbert Farkas, Hermann Sahm, Stephanie Bringer-Meyer, Otto Goebel and Dieter Mayer in "Ethanol" Ullmann's Encyclopedia of Industrial Chemistry, 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_587.pub2
    


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Further reading

.mw-parser-output .refbegin{font-size:90%;margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{list-style-type:none;margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li,.mw-parser-output .refbegin-hanging-indents>dl>dd{margin-left:0;padding-left:3.2em;text-indent:-3.2em;list-style:none}.mw-parser-output .refbegin-100{font-size:100%}

• 
  Chang C, Stadler R; Stadler (July 2001). "Ethylene hormone receptor action in Arabidopsis". BioEssays. 23 (7): 619–27. doi:10.1002/bies.1087. PMID 11462215.
  


• 
  Millenaar FF, van Zanten M, Cox MC, Pierik R, Voesenek LA, Peeters AJ; Van Zanten; Cox; Pierik; Voesenek; Peeters (2009). "Differential petiole growth in Arabidopsis thaliana: photocontrol and hormonal regulation". New Phytol. 184 (1): 141–52. doi:10.1111/j.1469-8137.2009.02921.x. PMID 19558423.CS1 maint: Multiple names: authors list (link)
  


• 
  Schaller, George E (2012). "Ethylene and the regulation of plant development". BMC Biology (published 20 February 2012). 10 (9): 9. doi:10.1186/1741-7007-10-9. PMC 3282650. PMID 22348804. Retrieved February 20, 2012.
  

External links

Wikimedia Commons has media related to Ethylene.

• International Chemical Safety Card 0475


• 
  European Chemicals Bureau Datasheet^{[permanent dead link]}
  


• Speculations Towards a General Plant Hormone Theory


• MSDS

v t e Alkenes
Ethene ( C 2H 4 ) Propene ( C 3H 6 ) Butene ( C 4H 8 ) Pentene ( C 5H 10 ) Hexene ( C 6H 12 ) Heptene ( C 7H 14 ) Octene ( C 8H 16 ) Nonene ( C 9H 18 ) Decene ( C 10H 20 )

v t e Functional groups
Only carbon, hydrogen, and oxygen Hydrocarbons Allene Alkene (Allyl, Vinyl) Alkyl (Methyl, Ethyl, Propyl, Butyl, Pentyl) Alkyne Benzyl Carbene Cumulene Methylene bridge Methylene group Methine Phenyl Other Acetoxy Acetyl Acryloyl Acyl Aldehyde Alkoxy (Methoxy) Benzoyl Carbonyl Carboxyl Carboxylic anhydride Dioxirane Epoxide Ester Ether Ethylenedioxy Hydroxy Ketone Methylenedioxy Peroxide (Organic) Ynone Only one element apart from C, H, O Nitrogen Amine Azo compound Cyanate Hydrazone Imide Imine Isocyanate Isonitrile Nitrene Nitrile Nitro compound Nitroso compound Organic amide Oxime Phosphorus Phosphonate Phosphonous Sulfur Disulfide Sulfone Sulfonic acid Sulfoxide Thial Thioester Thioether Thioketone Thiol Selenium Selenol Selenonic acid Seleninic acid Selenenic acid Tellurium Tellurol Other Isothiocyanate Phosphoramide Sulfenyl chloride Sulfonamide Thiocyanate
See also chemical classification, chemical nomenclature (inorganic, organic)

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argonium Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen (molecular) Nitrogen monohydride Nitrogen sulfide Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide Triatomic Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon sulfide Thiocyanic acid Five atoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal Nine atoms Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60 fullerene, buckyball) C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Methylacetylene N2D+ Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidine
Related	Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin
Category:Astrochemistry Portal:Astrobiology

v t e General anesthetics (N01A)
Inhalational	Chloroethane (ethyl chloride)‡ Chloroform‡ Cyclopropane‡ Desflurane Diethyl ether‡ Enflurane Ethylene‡ Fluroxene‡ Halothane# Isoflurane# Methoxyflurane Methoxypropane‡ Nitrous oxide# Sevoflurane Trichloroethylene‡ Vinyl ether‡ Xenon
Injection	Phenols Fospropofol Propofol# Opioids Morphine# Oxycodone Anileridine‡ Embutramide‡ Fentanyl# Alfentanil Phenoperidine Remifentanil÷ Sufentanil Arylcyclohexylamines Esketamine Ketamine# Phencyclidine‡ Tiletamine Neuroactive steroids Alfadolone Alfaxalone Hydroxydione Others Propanidid‡
#WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

v t e Plant hormones
24-Epibrassinolide Abscisic acid Auxins Cytokinins Ethylene Gibberellins
Brassinosteroids Florigen Jasmonates Karrikins Plant peptide hormones Polyamine Salicylic acid Strigolactones

v t e Binary compounds of hydrogen
Alkali metal hydrides	LiH NaH KH RbH CsH	Lithium hydride, LiH ionic metal hydride Beryllium hydride Left (gas phase): BeH2 covalent metal hydride Right: (BeH2)n (solid phase) polymeric metal hydride Borane and diborane Left: BH3 (special conditions), covalent metalloid hydride Right: B2H6 (standard conditions), dimeric metalloid hydride Methane, CH4 covalent nonmetal hydride Ammonia, NH3 covalent nonmetal hydride Water, H2O covalent nonmetal hydride Hydrogen fluoride, HF covalent nonmetal hydride
Alkaline earth hydrides	Monohydrides BeH MgH CaH SrH BaH Dihydrides BeH2 MgH2 CaH2 SrH2 BaH2
Group 13 hydrides	Boranes BH3 B2H6 B2H2 B2H4 B4H10 B5H9 B5H11 B6H10 B6H12 B10H14 B18H22 Alanes AlH3 Al2H6 Gallanes GaH3 Ga2H6 Indiganes InH3 In2H6 Thallanes TlH3 Tl2H6
Group 14 hydrides	Linear alkanes CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 more... Linear alkenes C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 more... Linear alkynes C2H2 C3H4 C4H6 C5H8 C6H10 C7H12 C8H14 C9H16 C10H18 more... Silanes SiH4 Si2H6 Si3H8 Si4H10 Si5H12 Si6H14 Si7H16 Si8H18 Si9H20 Si10H22 more... Silenes Si2H4 Silynes Si2H2 SiH Germanes GeH4 Ge2H6 Ge3H8 Ge4H10 Ge5H12 Stannanes SnH4 Sn2H6 Plumbanes PbH4 CH CH2 CH3 C2H Cycloalkanes Cycloalkenes Annulenes Many more
Pnictogen hydrides	Azanes NH3 N2H4 N3H5 N4H6 N5H7 N6H8 N7H9 N8H10 N9H11 N10H12 more... Azenes N2H2 N3H3 N4H4 Phosphanes PH3 P2H4 P3H5 P4H6 P5H7 P6H8 P7H9 P8H10 P9H11 P10H12 more... Phosphenes P2H2 P3H3 P4H4 Arsanes AsH3 As2H4 Stibanes SbH3 Bismuthanes BiH3 HN3 NH radical
Hydrogen chalcogenides	Polyoxidanes H2O H2O2 H2O3 H2O4 H2O5 H2O6 H2O7 H2O8 H2O9 H2O10 more... Polysulfanes H2S H2S2 H2S3 H2S4 H2S5 H2S6 H2S7 H2S8 H2S9 H2S10 more... Selanes H2Se H2Se2 Tellanes H2Te H2Te2 Polanes PoH2 HO HO2 HO3 H2O+–O– H2S=S (HS)2S+–S– HS HDO D2O T2O
Hydrogen halides	HF HCl HBr HI HAt
Transition metal hydrides	ScH2 YH2 YH3 TiH2 ZrH2 HfH2 VH VH2 NbH NbH2 TaH CrH CrH2 CrHx NiH PdHx (x < 1) FeH FeH2 FeH5 CuH ZnH2 CdH2 HgH2
Lanthanide hydrides	LaH2 LaH3 LaH10 CeH2 CeH3 PrH2 PrH3 NdH2 NdH3 SmH2 SmH3 EuH2 GdH2 GdH3 TbH2 TbH3 DyH2 DyH3 HoH2 HoH3 ErH2 ErH3 TmH2 TmH3 YbH2 YbH2.5 LuH2 LuH3
Actinide hydrides	AcH2 ThH2 Th4H15 PaH3 UH3 NpH2 NpH3 PuH2 PuH3 AmH2 AmH3 CmH2

v t e GABAA receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423 Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Fospropofol Propofol Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (niacinamide) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

Authority control	BNE: XX534539 BNF: cb12062004j (data) GND: 4140264-9 LCCN: sh85045433 NDL: 00562060 SUDOC: 028875109

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