Piperylene or 1,3-pentadiene is an organic compound with the formula CH3−CH=CH−CH=CH2. 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.[2] It consists of two isomers, Z and E, but these are rarely distiguighed.
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| Names | |
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| Preferred IUPAC name
(3E)-Penta-1,3-diene | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.269 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1993 3295 1010 |
CompTox Dashboard (EPA) |
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| Properties | |
| C5H8 | |
| Molar mass | 68.117 g/mol |
| Appearance | Colorless liquid |
| Density | 0.683 g/cm3 |
| Melting point | −87 °C (−125 °F; 186 K) E-isomer |
| Boiling point | 42 °C (108 °F; 315 K) E-isomer |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225, H304, H315, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
| Flash point | < −30 °C (−22 °F; 243 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and formation
editThe dominant route to piperylene is by steam cracking of naphtha]]. This makes up about 10% of the C5 stream.[3]
Other routes
editPiperylene is a product of the decarboxylation of sorbic acid.[4]
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.[5]
Reactions
editPiperylene behaves as a typical diene. It forms a sulfolene upon treatment with sulfur dioxide.[6] It participates in Ziegler-Natta polymerization.[7] It is converted to 2-Methyltetrahydrofuran by reaction with water. It undergoes hydrocyanation.[3]
Piperylene can be deprotonated using butyl lithium, providing lithium pentadienyl.[8]
See also
editReferences
edit- ↑ Safety (MSDS) data for piperylene Archived 2007-10-11 at the Wayback Machine. Retrieved 2007-11-14.
- ↑ Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 978-3-527-30673-2.
- 1 2 Herrmann, Norman; Vogelsang, Dennis; Behr, Arno; Seidensticker, Thomas (2018). "Homogeneously Catalyzed 1,3-Diene Functionalization – A Success Story from Laboratory to Miniplant Scale". ChemCatChem. 10 (23): 5342–5365. doi:10.1002/cctc.201801362.
- ↑ Erich Lück, Martin Jager, Nico Raczek (2000). "Sorbic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_507. ISBN 3527306730.
{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link) - ↑ Piperylene Archived 2009-05-13 at the Wayback Machine at Shell Chemicals. Retrieved 2009-05-19.
- ↑ Robert L. Frank, Raymond P. Seven (1949). "Isoprene Cyclic Sulfone". Organic Syntheses. 29: 59. doi:10.15227/orgsyn.029.0059.
- ↑ Ricci, Giovanni; Pampaloni, Guido; Sommazzi, Anna; Masi, Francesco (2021). "Dienes Polymerization: Where We Are and What Lies Ahead". Macromolecules. 54 (13): 5879–5914. doi:10.1021/acs.macromol.1c00004.
- ↑ Seyferth, Dietmar; Pornet, Jacques (1980). "(2,4-Pentadienyl)trimethylsilane: A useful pentadienylation reagent". The Journal of Organic Chemistry. 45 (9): 1721–1722. doi:10.1021/jo01297a053.
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