Ethylene
From Free net encyclopedia
Ethylene (or IUPAC name ethene) is the simplest alkene hydrocarbon, consisting of four hydrogen atoms and two carbon atoms connected by a double bond. Because it contains a double bond, ethylene is called an unsaturated hydrocarbon or an olefin.
The molecule cannot twist around the double bond, and all six atoms lie in the same plane. The angle made by two carbon-hydrogen bonds in the molecule is 117°, very close to the 120° that would be predicted from ideal sp2 hybridization.
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Nomenclature
From 1795 on, ethylene was referred to as the olefiant gas (oil-making gas), because it combined with chlorine to produce the oil of the Dutch chemists (ethylene dichloride), first synthesized in 1795 by a collaboration of four Dutch chemists.
In the mid-19th century, the suffix -ene (a 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 word being modified. Thus, ethylene (C2H4) was the "daughter of ethyl" (C2H5). The name ethylene was used in this sense as early as 1852.
In 1866, the German chemist Augustus 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[1]. 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.
Chemistry
The double bond is a region of slightly higher electron density, and most of ethylene's chemistry involves other molecules reacting with and adding across its double bond. Ethylene can react with bromine, chlorine, and other halogens, to produce halogenated hydrocarbons. It can also react with water to produce ethanol, but the rate at which this happens is very slow unless a suitable catalyst, such as phosphoric or sulfuric acid, is used. Under high pressure, and, in the presence of a catalytic metal (platinum, rhodium, nickel), hydrogen will react with ethylene.
Production
Ethylene is produced in the petrochemical industry via steam cracking. In this process, gaseous or light liquid hydrocarbons are briefly heated to 750–950 °C, causing numerous free radical reactions to take place. Generally, in the course of these reactions, large hydrocarbons break down in to smaller ones and saturated hydrocarbons become unsaturated.
The result of this process is a complex mixture of hydrocarbons in which ethylene is one of the principal components. The mixture is separated by repeated compression and distillation.
Another process is catalytic cracking where it is used in oil refineries to crack large hydrocarbon molecules into smaller ones. Use of zeolite as a catalyst allows the cracking to be achieved at a lower temperature. It is an important way of separating alkenes from alkanes using a fractionating column.
Theoretical considerations
Although ethylene is a relatively simple molecule, its spectra is considered to be one of the most difficult to explain adequately from both a theoretical and practical perspective. For this reason, it is often used as a test case in computational chemistry. Of particular note is the difficulty in characterizing the ultraviolet absorption the molecule. Interest in the subtleties and details of the ethylene spectrum can be dated back to at least the 1950s.
Uses
- Chemistry
Ethylene is used primarily as an intermediate in the manufacture of other chemicals, especially plastics. Ethylene may be polymerized directly to produce polyethylene (also called polyethene or polythene), the world's most widely-used plastic. Ethylene can be chlorinated to produce ethylene dichloride (1,2-Dichloroethane), a precursor to the plastic polyvinyl chloride, or combined with benzene to produce ethylbenzene, which is used in the manufacture of polystyrene, another important plastic.
Smaller amounts of ethylene are oxidized to produce chemicals including ethylene oxide, ethanol, and polyvinyl acetate.
Ethylene was once used as an inhaled anesthetic, but it has long since been replaced in this role by nonflammable gases.
It has also been hypothesized that ethylene was the catalyst for utterances of the oracle at Delphi in ancient Greece.
Ethylene is used in greenhouses and is sprayed on crops to speed ripening.
Ethylene as a plant hormone
Ethylene functions as a hormone in plants. It stimulates the ripening of fruit, the opening of flowers, and the abscission (or shedding) of leaves. Its biosynthesis starts from methionine with 1-aminocyclopropane-1-carboxylic acid (ACC) as a key intermediate.
"Ethylene has been used in practice since the ancient Egyptians, who would gas figs in order to stimulate ripening. The ancient Chinese would burn incense in closed rooms to enhance the ripening of pears. It was in 1864, that leaks of gas from street lights showed stunting of growth, twisting of plants, and abnormal thickening of stems (the triple response)[see plant senescence](Arteca, 1996; Salisbury and Ross, 1992). In 1901, a russian scientist named Dimitry Neljubow showed that the active component was ethylene (Neljubow, 1901). Doubt discovered that ethylene stimulated abscission in 1917 (Doubt, 1917). It wasn't until 1934 that Gane reported that plants synthesize ethylene (Gane, 1934). In 1935, Crocker proposed that ethylene was the plant hormone responsible for fruit ripening as well as inhibition of vegetative tissues (Crocker, 1935). Ethylene is now known to have many other functions as well." - from (plant-hormones.info)
Location, Characteristics and Occasions for Synthesis Induction
- Directly induced by high levels of auxin
- Found in germinating seeds
- Induced by root flooding
- Induced by drought
- Synthesized in nodes of stems
- Synthesized in tissues of ripening fruits
- Synthesized in response to shoot environmental, pest, or disease stress
- Synthesized in senescent leaves and flowers
- Rapidly diffuses
- Inhibiting effects of ethylene on shoot growth (more specifically on stem elongation) reduced in the presence of light. Also ethylene levels are decreased by light
- The above may be because light induces auxin synthesis and moderate auxin levels inhibit ethylene. (speculative)
- Released in mature (and to a lesser extent immature cells) cells when they do not have enough minerals and water to support both themselves and any dependent cells. (speculative)
Effects
- Stimulates leaf and flower senescence
- Induces leaf abscission mainly in older leaves.
- Induces seed germination
- Induces root hair growth – this increases the efficiency of water and mineral absorption
- Stimulates epinasty – leaf petiole grows out, leaf hangs down and curls into itself
- Stimulates fruit ripening
- Induces the growth of adventitious roots during flooding
- Usually inhibits growth - although perhaps just shoot growth (speculative)
- Affects neighboring individuals
- Disease/wounding resistance
- Triple response when applied to seedlings – root ? and shoot growth inhibition and pronounced hypocotyl hook bending
- Inhibits stem swelling ? (Contradictory to the finding below – contradictory sources)
- Stimulates cell broadening (and lateral root growth)
- Interference with auxin transport (with high auxin concentrations)
- Directly or indirectly induces auxin at high levels (speculative)
- Inhibits the rate of metabolism of cells in the shoot so as to redirect resources to the root (speculative)
- Is a general indicator of poor root health. Strategy of senescent leaves may to funnel more resources to the root. (speculative)
- May be more active at night when root and mineral acquisition are, on average, lower (speculative)
- Just as a role of auxin may be to increase minerals and water by shoot growth, ethylene may do this by shoot senescence. Cytokinin and auxin hormones are released when conditions are favorable for growth, for example during the day. Ethylene and gibberellin (or brassinosteroid) may be released when the plant must either cut back in size, or survive on stored resources, for example during the night. (speculative)
- Induces flowering in pineapples
- In food production, some plants are considered ethylene producers, while others are considered ethylene sensitive.
External links
| Plant hormones | edit |
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Abscisic acid - Auxins - Cytokinins - Ethylene (Ethene) - Gibberellins |
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