{{Short description|1=Hydrocarbon compound (CH3–CH=CH–CH=CH2)}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 430877984 | Reference = <ref>[http://ptcl.chem.ox.ac.uk/MSDS/PI/piperylene.html Safety (MSDS) data for piperylene] {{Webarchive|url=https://web.archive.org/web/20071011110901/http://ptcl.chem.ox.ac.uk/MSDS/PI/piperylene.html |date=2007-10-11 }}. Retrieved 2007-11-14.</ref> | ImageFile = Piperylene.svg | ImageSize = | ImageFile1 = Piperylene3D.png | ImageSize1 = | PIN = (3''E'')-Penta-1,3-diene | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | CASNo_Ref = {{cascite|correct|CAS}} | index1_label = ''trans'' | CASNo = 504-60-9 | CASNo1 = 2004-70-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = FW963NF88B | EINECS = 207-995-2 | PubChem = 62204 | RTECS = RZ2464000 | UNNumber = 1993 3295 1010 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 56020 | SMILES = C/C=C/C=C | InChI = 1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+ | InChIKey = PMJHHCWVYXUKFD-SNAWJCMRBX | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = PMJHHCWVYXUKFD-SNAWJCMRSA-N | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 74165 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=5 | H=8 | MolarMass = 68.117 g/mol | Appearance = Colorless liquid | Density = 0.683 g/cm<sup>3</sup> | MeltingPtC = -87 | MeltingPt_notes = E-isomer | BoilingPtC = 42 | BoilingPt_notes = E-isomer | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|304|315|319|335}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|301+310|302+352|303+361+353|304+340|305+351+338|312|321|331|332+313|337+313|362|370+378|403+233|403+235|405|501}} | FlashPt = < | FlashPtC = −30 | AutoignitionPt = | ExploLimits = | PEL = }} }}
'''Piperylene''' or '''1,3-pentadiene''' is an organic compound with the formula {{chem2|CH3\sCH\dCH\sCH\dCH2}}. It is a volatile, flammable hydrocarbon. It is one of the five positional isomers of pentadiene. It is one of several industrially significant 1,3-dienes, but it has received much less attention than butadiene and isoprene.<ref>{{cite book |last1=Schmidt |first1=Roland |last2=Griesbaum |first2=Karl |last3=Behr |first3=Arno |last4=Biedenkapp |first4=Dieter |last5=Voges |first5=Heinz-Werner |last6=Garbe |first6=Dorothea |last7=Paetz |first7=Christian |last8=Collin |first8=Gerd |last9=Mayer |first9=Dieter |last10=Höke |first10=Hartmut |title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Hydrocarbons |date=2014 |pages=1–74 |doi=10.1002/14356007.a13_227.pub3 |isbn=978-3-527-30673-2 }}</ref> It consists of two isomers, Z and E, but these are rarely distiguighed.
==Synthesis and formation== The dominant route to piperylene is by steam cracking of naphtha]]. This makes up about 10% of the C5 stream.<ref name=Herrmann>{{cite journal |last1=Herrmann |first1=Norman |last2=Vogelsang |first2=Dennis |last3=Behr |first3=Arno |last4=Seidensticker |first4=Thomas |title=Homogeneously Catalyzed 1,3-Diene Functionalization – A Success Story from Laboratory to Miniplant Scale |journal=ChemCatChem |date=2018 |volume=10 |issue=23 |pages=5342–5365 |doi=10.1002/cctc.201801362}}</ref>
===Other routes=== Piperylene is a product of the decarboxylation of sorbic acid.<ref name=Ullmann>{{cite encyclopedia|author=Erich Lück, Martin Jager, Nico Raczek|title=Sorbic Acid|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|location=Weinheim|year=2000|doi=10.1002/14356007.a24_507|isbn=3527306730 }}</ref>
Piperylene is obtained as a byproduct of ethylene production from crude oil, combustion of biomass, waste incineration and exhaust gases. It is used as a monomer in the manufacturing of plastics, adhesives and resins.<ref>[http://www.shell.com/home/content/chemicals/products_services/our_products/lower_olefins/piperylene/product_overview/piperylene_overview.html Piperylene] {{webarchive|url=https://web.archive.org/web/20090513042134/http://www.shell.com/home/content/chemicals/products_services/our_products/lower_olefins/piperylene/product_overview/piperylene_overview.html |date=2009-05-13 }} at Shell Chemicals. Retrieved 2009-05-19.</ref>
==Reactions== Piperylene behaves as a typical diene. It forms a sulfolene upon treatment with sulfur dioxide.<ref>{{cite journal |doi=10.15227/orgsyn.029.0059|title=Isoprene Cyclic Sulfone |journal=Organic Syntheses |year=1949 |volume=29 |page=59|author=Robert L. Frank, Raymond P. Seven }}</ref> It participates in Ziegler-Natta polymerization.<ref>{{cite journal |last1=Ricci |first1=Giovanni |last2=Pampaloni |first2=Guido |last3=Sommazzi |first3=Anna |last4=Masi |first4=Francesco |title=Dienes Polymerization: Where We Are and What Lies Ahead |journal=Macromolecules |date=2021 |volume=54 |issue=13 |pages=5879–5914 |doi=10.1021/acs.macromol.1c00004}}</ref> It is converted to 2-Methyltetrahydrofuran by reaction with water. It undergoes hydrocyanation.<ref name=Herrmann/>
Piperylene can be deprotonated using butyl lithium, providing lithium pentadienyl.<ref>{{cite journal |last1=Seyferth |first1=Dietmar |last2=Pornet |first2=Jacques |title=(2,4-Pentadienyl)trimethylsilane: A useful pentadienylation reagent |journal=The Journal of Organic Chemistry |date=1980 |volume=45 |issue=9 |pages=1721–1722 |doi=10.1021/jo01297a053}}</ref>
==See also== * Butadiene * Cyclopentadiene * Isoprene
==References== {{Reflist}}
Category:Alkadienes Category:Conjugated dienes
{{hydrocarbon-stub}} {{Hydrocarbons}}