Ethylene

Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016[8]) exceeds that of any other organic compound.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.[12] 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.Linear alpha-olefins, produced by oligomerization (formation of short-chain molecules) are used as precursors, detergents, plasticisers, synthetic lubricants, additives, and also as co-monomers in the production of polyethylenes.[17] The hydroformylation (oxo reaction) of ethylene results in propionaldehyde, a precursor to propionic acid and n-propyl alcohol.To meet the ever-increasing demand for ethylene, sharp increases in production facilities are added globally, particularly in the Mideast and in China.[17] 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).[31] It can be produced via dehydration of ethanol with sulfuric acid or in the gas phase with aluminium oxide or activated alumina.[35] 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.[36] Ethylene appears to have been discovered by Johann Joachim Becher, who obtained it by heating ethanol with sulfuric acid;[37] he mentioned the gas in his Physica Subterranea (1669).[38] 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.)[41] 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.[50] "A key factor affecting petrochemicals life-cycle emissions is the methane intensity of feedstocks, especially in the production segment.[53] Both steam cracking and production from natural gas via ethane are estimated to emit 1.8 to 2kg of CO2 per kg ethylene produced,[54] totalling over 260 million tonnes a year.
NFPA 704 four-colored diamond Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazards (white): no code
Orbital description of bonding between ethylene and a transition metal
Diagram of uses of ethene
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 .
Chlorobis(ethylene)rhodium dimer is a well-studied complex of ethylene. [ 34 ]
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dimerligandtransition metal alkene complexesZeise's saltDelphiPythiaJohann Joachim BecherJoseph PriestleyJan Ingenhouszchlorine1,2-dichloroethaneGermanAugust Wilhelm von Hofmannalkanedivalentasphyxiantgroup 3 agentRediRipeGESTIS Substance DatabaseInstitute for Occupational Safety and HealthBibcodeWayback MachineThe Plant Cellarchive.todayNational Non-Food Crops CentreOil & Gas JournalNational GeographicRoyal Society of ChemistryAlkenesButenePenteneHexeneHepteneOcteneNoneneDeceneDehydrohalogenationhaloalkaneDehydration reactionalcoholSemihydrogenationalkyneBamford–Stevens reactionBarton–Kellogg reactionBoord olefin synthesisChugaev eliminationCope reactionCorey–Winter olefin synthesisGrieco eliminationHofmann eliminationHorner–Wadsworth–Emmons reactionHydrazone iodinationJulia olefinationKauffmann olefinationMcMurry reactionPeterson olefinationRamberg–Bäcklund reactionShapiro reactionTakai olefinationWittig reactionOlefin metathesisEne reactionCope rearrangementHydrogenationOxymercuration reactionHydroborationCyclopropanationEpoxidationDihydroxylationOzonolysisDiels–Alder reactionDehydrogenationFriedel-Crafts AlkylationFunctional groupsHydrocarbonsMethylPropylCyclopropylPentylMethyleneBridgeMethine1-PropenylCrotylAlleneCumulenePhenylBenzylCarbeneoxygenAcetalAlkoxyMethoxyEnol etherEpoxidePeroxyHydroperoxyDioxiranesEthylenedioxyMethylenedioxycarbonylAcetylAcryloylBenzoylAldehydeKeteneKetoneReductoneCarboxylAcetoxyAnhydrideOrthoesterNitrogenEnamineAmmoniumHydrazoNitreneHydrazoneImidateAmidineCarbamateNitrileIsonitrileCyanateIsocyanateNitrateNitriteNitrosoNONOatePhosphorusPhosphatePhosphodiesterPhosphonatePhosphitePhosphonousPhosphinatePhosphine oxidePhosphinePhosphoniumPhosphaalkenePhosphaalkynePhosphaalleneSulfurSulfideSulfoniumPersulfideDisulfideSulfenic acidThiosulfinateSulfoxideThiosulfonateSulfinic acidSulfoneSulfonic acidThioketoneThioesterThionoesterThioxanthateXanthateBoronic acidBorinic acidSeleniumSelenolSelenonic acidSeleninic acidSelenenic acidSeloneTelluriumTellurolTelluroketoneFluoroethylTrifluoromethylTrichloromethylTrifluoromethoxyHypervalent iodineVinyl halideIodideAcyl halideChloridePerchlorateIsothiocyanatePhosphoramidesSulfenyl chlorideSulfonamideThiocyanateSulfinylamineschemical classificationchemical nomenclatureinorganicorganicMolecules detected in outer spaceMoleculesDiatomicAluminium monochlorideAluminium monofluorideAluminium(II) oxideArgoniumCarbon cationCarbon monophosphideCarbon monosulfideCarbon monoxideCyano radicalDiatomic carbonHelium hydride ionHydrogen chlorideHydrogen fluorideHydroxyl radicalIron(II) oxideMagnesium monohydrideMethylidyne radicalNitric oxideImidogenSulfur mononitridePhosphorus monoxidePhosphorus mononitridePotassium chlorideSilicon carbideSilicon monoxideSilicon monosulfideSodium chlorideSodium iodideSulfanylSulfur monoxideTitanium(II) oxideTriatomicAluminium(I) hydroxideAmino radicalCarbonyl sulfideChloroniumDiazenyliumDicarbon monoxideEthynyl radicalHydrogen cyanideHydrogen isocyanideHydrogen sulfideHydroperoxylIron cyanideMagnesium cyanideNitrous oxideNitroxylMethylidynephosphanePotassium cyanideTrihydrogen cationSodium cyanideSodium hydroxideSulfur dioxideThioxoethenylideneTricarbonAmmoniaIsocyanic acidCyanoethynylFormaldehydeFulminic acidHydrogen peroxideIsothiocyanic acidMethyl cationMethyl radicalPropynylidyneProtonated hydrogen cyanideThioformaldehydeTricarbon monoxideTricarbon monosulfideThiocyanic acidButadiynylCarbodiimideCyanamideCyanoacetyleneCyanomethylCyclopropenylideneFormic acidMethoxy radicalSilaneAcetonitrileCyclopropenoneDiacetyleneFormamideKetenimineMethanethiolMethanolMethyl isocyanidePentynylidynePropynalAcrylonitrileVinyl cyanideCyanodiacetyleneGlycolonitrileHexatriynyl radicalPropyneMethylamineMethyl isocyanateVinyl alcoholAcetic acidAminoacetonitrileEthanimineGlycolaldehydeHexapentaenylideneMethylcyanoacetyleneMethyl formateAcroleinAcetamideCyanohexatriyneDimethyl etherMethyldiacetyleneOctatetraynyl radicalEthanethiolPropionitrileN-MethylformamideAcetoneBenzeneBenzonitrileBuckminsterfullereneC70 fullereneCyanodecapentayneEthyl formateMethyl acetateMethyl-cyano-diacetyleneMethyltriacetyleneButyronitrilePyrimidineDeuteratedHeavy waterHydrogen deuterideAnthraceneDihydroxyacetoneMethoxyethaneGlycineGrapheneHemolithinLinear C5Naphthalene cationPyreneSilylidyneAbiogenesisAstrobiologyAstrochemistryAtomic and molecular astrophysicsCircumstellar dustCircumstellar envelopeCosmic dustCosmic rayCosmochemistryDiffuse interstellar bandEarliest known life formsExtraterrestrial lifeExtraterrestrial liquid waterForbidden mechanismHomochiralityIntergalactic dustInterplanetary mediumInterstellar mediumPhotodissociation regionIron–sulfur world theoryKerogenMolecules in starsNexus for Exoplanet System ScienceOuter spacePAH world hypothesisPseudo-panspermiaPolycyclic aromatic hydrocarbonRNA world hypothesisSpectroscopyTholinGeneral 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