:Piperylene
{{Short description|1=Hydrocarbon compound (CH3−CH=CH−CH=CH2)}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 430877984
| Reference = [http://ptcl.chem.ox.ac.uk/MSDS/PI/piperylene.html Safety (MSDS) data for piperylene]. Retrieved 2007-11-14.
| ImageFile = Piperylene.svg
| ImageSize =
| ImageFile1 = Piperylene3D.png
| ImageSize1 =
| PIN = (3E)-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/cm3
| 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.
Reactions and occurrence
Piperylene is a typical diene. It forms a sulfolene upon treatment with sulfur dioxide.{{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 }}
Piperylene is the product of the decarboxylation of sorbic acid, a common anti-mold agent.{{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 }}
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.[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.