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c 77 f 100 kpa y verify what is y n infobox references chemical compound propylene also known as propene is an unsaturated organic compound with the chemical formula ch 3 ch ch 2 it has one double bond and is the second simplest member of the alkene class of hydrocarbons it is a colorless gas with a faint petroleum like odor 4 propylene is a product of combustion from forest fires cigarette smoke and motor vehicle and aircraft exhaust 5 it was discovered in 1850 by a w von hoffmann s student john williams reynolds as the only gaseous product of thermal decomposition of amyl alcohol to react with chlorine and bromine 6 production edit steam cracking edit main article steam cracking the dominant technology for producing propylene is steam cracking using propane as the feedstock cracking propane yields a mixture of ethylene propylene methane hydrogen gas and other related compounds the yield of propylene is about 15 the other principal feedstock is naphtha especially in the middle east and asia 7 propylene can be separated by fractional distillation from the hydrocarbon mixtures obtained from cracking and other refining processes refinery grade propene is about 50 to 70 8 in the united states shale gas is a major source of propane olefin conversion technology edit in the phillips triolefin or olefin conversion technology propylene is interconverted with ethylene and 2 butenes rhenium and molybdenum catalysts are used 9 ch 2 ch 2 ch 3 ch chch 3 re mo catalyst 2 ch 2 chch 3 displaystyle ce ch2 ch2 ch3ch chch3 text re mo atop text catalyst 2ch2 chch3 the technology is founded on an olefin metathesis reaction discovered at phillips petroleum company 10 11 propylene yields of about 90 wt are achieved main article syngas to gasoline plus related is the methanol to olefins methanol to propene process it converts synthesis gas syngas to methanol and then converts the methanol to ethylene and or propene the process produces water as a by product synthesis gas is produced from the reformation of natural gas or by the steam induced reformation of petroleum products such as naphtha or by gasification of coal or natural gas fluid catalytic cracking edit high severity fluid catalytic cracking fcc uses traditional fcc technology under severe conditions higher catalyst to oil ratios higher steam injection rates higher temperatures etc in order to maximize the amount of propene and other light products a high severity fcc unit is usually fed with gas oils paraffins and residues and produces about 20 25 by mass of propene on feedstock together with greater volumes of motor gasoline and distillate byproducts these high temperature processes are expensive and have a high carbon footprint for these reasons alternative routes to propylene continue to attract attention 12 other commercialized methods edit on purpose propylene production technologies were developed throughout the twentieth century of these propane dehydrogenation technologies such as the catofin and oleflex processes have become common although they still make up a minority of the market with most of the olefin being sourced from the above mentioned cracking technologies platinum chromia and vanadium catalysts are common in propane dehydrogenation processes market edit propene production has remained static at around 35 million tonnes europe and north america only from 2000 to 2008 but it has been increasing in east asia most notably singapore and china 13 total world production of propene is currently about half that of ethylene research edit the use of engineered enzymes has been explored but has not been commercialized 14 there is ongoing research into the use of oxygen carrier catalysts for the oxidative dehydrogenation of propane this poses several advantages as this reaction mechanism can occur at lower temperatures than conventional dehydrogenation and may not be equilibrium limited because oxygen is used to combust the hydrogen by product 15 uses edit propylene is the second most important starting product in the petrochemical industry after ethylene it is the raw material for a wide variety of products polypropylene manufacturers consume nearly two thirds of global production 16 polypropylene end uses include films fibers containers packaging and caps and closures propene is also used for the production of chemicals such as propylene oxide acrylonitrile cumene butyraldehyde and acrylic acid in the year 2013 about 85 million tonnes of propylene were processed worldwide 16 propylene and benzene are converted to acetone and phenol via the cumene process overview of the cumene process propylene is also used to produce isopropyl alcohol propan 2 ol acrylonitrile propylene oxide and epichlorohydrin 17 the industrial production of acrylic acid involves the catalytic partial oxidation of propylene 18 propylene is an intermediate in the oxidation to acrylic acid in industry and workshops propylene is used as an alternative fuel to acetylene in oxy fuel welding and cutting brazing and heating of metal for the purpose of bending it has become a standard in bernzomatic products and others in mapp substitutes 19 now that true mapp gas is no longer available reactions edit propylene resembles other alkenes in that it undergoes electrophilic addition reactions relatively easily at room temperature the relative weakness of its double bond explains its tendency to react with substances that can achieve this transformation alkene reactions include polymerization and oligomerization oxidation halogenation hydrohalogenation alkylation hydration hydroformylation complexes of transition metals edit foundational to hydroformylation alkene metathesis and polymerization are metal propylene complexes which are intermediates in these processes propylene is prochiral meaning that binding of a reagent such as a metal electrophile to the c c group yields one of two enantiomers polymerization edit see also polypropylene the majority of propylene is used to form polypropylene a very important commodity thermoplastic through chain growth polymerization 16 in the presence of a suitable catalyst typically a ziegler natta catalyst propylene will polymerize there are multiple ways to achieve this such as using high pressures to suspending the catalyst in a solution of liquid propylene or running gaseous propylene through a fluidized bed reactor 20 oligomerization edit in the presence of catalysts propylene will form various short oligomers it can dimerizes to give 2 3 dimethyl 1 butene and or 2 3 dimethyl 2 butene 21 or trimerise to form tripropylene environmental safety edit propene is a product of combustion from forest fires cigarette smoke and motor vehicle and aircraft exhaust 5 it is an impurity in some heating gases observed concentrations have been in the range of 0 1 4 8 parts per billion ppb in rural air 4 10 5 ppb in urban air and 7 260 ppb in industrial air samples 8 in the united states and some european countries a threshold limit value of 500 parts per million ppm was established for occupational 8 hour time weighted average exposure it is considered a volatile organic compound voc and emissions are regulated by many governments but it is not listed by the u s environmental protection agency epa as a hazardous air pollutant under the clean air act with a relatively short half life it is not expected to bioaccumulate 8 propene has low acute toxicity from inhalation and is not considered to be carcinogenic chronic toxicity studies in mice did not yield significant evidence suggesting adverse effects humans briefly exposed to 4 000 ppm did not experience any noticeable effects 22 propene is dangerous from its potential to displace oxygen as an asphyxiant gas and from its high flammability explosion risk bio propylene is the bio based propylene 23 24 it has been examined motivated by diverse interests such a carbon footprint production from glucose has been considered 25 more advanced ways of addressing such issues focus on electrification alternatives to steam cracking storage and handling edit propene is flammable propene is usually stored as liquid under pressure although it is also possible to store it safely as gas at ambient temperature in approved containers 26 occurrence in nature edit propene is detected in the interstellar medium through microwave spectroscopy 27 on september 30 2013 nasa announced the detection of small amounts of naturally occurring propene in the atmosphere of titan using infrared spectroscopy 28 29 30 the detection was made by a team led by nasa gsfc scientist conor nixon using data from the cirs instrument 31 32 on the cassini orbiter spacecraft part of the cassini huygens mission its confirmation solved a 32 year old mystery by filling a predicted gap in titan s detected hydrocarbons adding the c 3 h 6 species propene to the already detected c 3 h 4 propyne and c 3 h 8 propane 33 see also edit los alfaques disaster inhalant abuse 2014 kaohsiung gas explosions 2020 houston explosion titan moon references edit general principles rules and conventions nomenclature of organic chemistry iupac recommendations and preferred names 2013 blue book cambridge the royal society of chemistry 2014 p 31 doi 10 1039 9781849733069 00001 isbn 978 0 85404 182 4 moss g p web version p 14 3 locants nomenclature of organic chemistry iupac recommendations and preferred names 2013 london queen mary university section p 14 3 4 2 d retrieved 23 august 2024 propylene pubchem ncbi nlm nih gov retrieved 14 december 2021 propylene 1 2 morgott david 2018 01 04 the human exposure potential from propylene releases to the environment international journal of environmental research and public health 15 1 66 doi 10 3390 ijerph15010066 issn 1660 4601 pmc 5800165 pmid 29300328 rasmussen seth c 2018 introduction in rasmussen seth c ed acetylene and its polymers 150 years of history springerbriefs in molecular science cham springer international publishing pp 1 19 doi 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jennings d e flasar f m kunde v g nixon c a segura m e romani p n gorius n albright s brasunas j c carlson r c mamoutkine a a guandique e kaelberer m s aslam s achterberg r k 2017 06 20 composite infrared spectrometer cirs on cassini applied optics 56 18 5274 5294 bibcode 2017apopt 56 5274j doi 10 1364 ao 56 005274 issn 2155 3165 pmid 29047582 maguire w c hanel r a jennings d e kunde v g samuelson r e august 1981 c3h8 and c3h4 in titan s atmosphere nature 292 5825 683 686 doi 10 1038 292683a0 issn 1476 4687 v t e alkenes alkenes ethene c 2 h 4 propene c 3 h 6 butene c 4 h 8 pentene c 5 h 10 hexene c 6 h 12 heptene c 7 h 14 octene c 8 h 16 nonene c 9 h 18 decene c 10 h 20 polyenes preparations dehydrohalogenation from haloalkane dehydration reaction from alcohol semihydrogenation from alkyne bamford stevens reaction barton kellogg reaction boord olefin synthesis chugaev elimination cope reaction corey winter olefin synthesis grieco elimination hofmann elimination horner wadsworth emmons 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