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ropylene skeletal formula of propene propylene names preferred iupac name propene 1 2 identifiers cas number 115 07 1 y 3d model jsmol interactive image interactive image beilstein reference 1696878 chebi chebi 16052 y chembl chembl117213 y chemspider 7954 y echa infocard 100 003 693 ec number 204 062 1 gmelin reference 852 kegg c11505 y pubchem cid 8252 rtecs number uc6740000 unii aug1h506ly y un number 1077 in liquefied petroleum gas 1075 comptox dashboard epa dtxsid5021205 inchi inchi 1s c3h6 c1 3 2 h3h 1h2 2h3 y key qqonpfptgqhpma uhfffaoysa n y inchi 1 c3h6 c1 3 2 h3h 1h2 2h3 key qqonpfptgqhpma uhfffaoyaa smiles c cc cc c properties chemical formula c 3 h 6 molar mass 42 081 g mol 1 appearance colorless gas density 1 81 kg m 3 gas 1 013 bar 15 c 1 745 kg m 3 gas 1 013 bar 25 c 613 9 kg m 3 liquid melting point 185 2 c 301 4 f 88 0 k boiling point 47 6 c 53 7 f 225 6 k solubility in water 0 61 g m 3 magnetic susceptibility χ 31 5 10 6 cm 3 mol viscosity 8 34 µpa s at 16 7 c structure dipole moment 0 366 d gas hazards ghs labelling 3 pictograms signal word danger hazard statements h220 precautionary statements p210 p377 p381 p403 nfpa 704 fire diamond 1 4 1 flash point 108 c 162 f 165 k safety data sheet sds external msds related compounds related alkenes related groups ethylene isomers of butylene allyl propenyl related compounds propane propyne propadiene 1 propanol 2 propanol except where otherwise noted data are given for materials in their standard state at 25 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 10 1007 978 3 319 95489 9_1 isbn 978 3 319 95489 9 ashford s dictionary of industrial chemicals third edition 2011 isbn 978 0 9522674 3 0 pages 7766 9 1 2 3 product safety assessment psa propylene dow chemical co archived from the original on 2013 08 28 retrieved 2011 07 11 ghashghaee mohammad 2018 heterogeneous catalysts for gas phase conversion of ethylene to higher olefins rev chem eng 34 5 595 655 doi 10 1515 revce 2017 0003 s2cid 103664623 banks r l bailey g c 1964 olefin disproportionation a new catalytic process industrial engineering chemistry product research and development 3 3 170 173 doi 10 1021 i360011a002 lionel delaude alfred f noels 2005 metathesis kirk othmer encyclopedia of chemical technology weinheim wiley vch doi 10 1002 0471238961 metanoel a01 isbn 978 0 471 23896 6 schiffer zachary j manthiram karthish 2017 electrification and decarbonization of the chemical industry joule 1 1 10 14 bibcode 2017joule 1 10s doi 10 1016 j joule 2017 07 008 hdl 1721 1 124019 s2cid 117360588 amghizar ismaël vandewalle laurien a van geem kevin m marin guy b 2017 new trends in olefin production engineering 3 2 171 178 bibcode 2017engin 3 171a doi 10 1016 j eng 2017 02 006 de guzman doris october 12 2012 global bioenergies in bio propylene green chemicals blog wu tianwei yu qingbo roghair et al 2020 chemical looping oxidative dehydrogenation of propane a comparative study of ga based mo based v based oxygen carriers chemical engineering and processing process intensification 157 108137 bibcode 2020ceppi 15708137w doi 10 1016 j cep 2020 108137 issn 0255 2701 1 2 3 market study propylene 2nd edition ceresana december 2014 ceresana com retrieved 2015 02 03 budavari susan ed 1996 8034 propylene the merck index twelfth edition new jersey merck co pp 1348 1349 j g l fierro ed 2006 metal oxides chemistry and applications crc press pp 414 455 for example mapp pro heggs t geoffrey 2011 10 15 polypropylene in wiley vch verlag gmbh co kgaa ed ullmann s encyclopedia of industrial chemistry weinheim germany wiley vch verlag gmbh co kgaa pp o21_o04 doi 10 1002 14356007 o21_o04 isbn 978 3 527 30673 2 retrieved 2021 07 09 olivier bourbigou h breuil p a r magna l michel t espada pastor m fernandez delcroix d 2020 nickel catalyzed olefin oligomerization and dimerization pdf chemical reviews 120 15 7919 7983 doi 10 1021 acs chemrev 0c00076 pmid 32786672 s2cid 221124789 pubchem hazardous substances data bank hsdb 175 pubchem ncbi nlm nih gov retrieved 2021 07 09 bio based drop in smart drop in and dedicated chemicals duurzame bioplastics op basis van hernieuwbare grondstoffen guzman doris de 12 october 2012 global bioenergies in bio propylene green chemicals blog retrieved 2021 07 09 encyclopedia of chemical technology fourth edition 1996 isbn 0471 52689 4 v 20 page 261 marcelino n cernicharo j agúndez m et al 2007 08 10 discovery of interstellar propylene ch2chch3 missing links in interstellar gas phase chemistry the astrophysical journal 665 2 iop l127 l130 arxiv 0707 1308 bibcode 2007apj 665l 127m doi 10 1086 521398 s2cid 15832967 spacecraft finds propylene on saturn moon titan upi com 2013 09 30 retrieved 2013 11 12 cassini finds ingredient of household plastic on saturn moon spacedaily com retrieved 2013 11 12 nixon c a jennings d e bézard b vinatier s teanby n a sung k ansty t m irwin p g j gorius n cottini v coustenis a flasar f m 2013 09 30 detection of propene in titan s stratosphere the astrophysical journal 776 1 l14 arxiv 1309 4489 bibcode 2013apj 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