Jump to content

Piperylene: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{chembox}} (changes to verified and watched fields - updated 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'Verifiedfields') per Chem/Drugbox validation (report errors or [[us...
m short description, chem formatting
Tags: Mobile edit Mobile app edit iOS app edit
 
(26 intermediate revisions by 17 users not shown)
Line 1: Line 1:
{{Short description|1=Hydrocarbon compound (CH3−CH=CH−CH=CH2)}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
Line 8: Line 9:
| ImageFile1 = Piperylene3D.png
| ImageFile1 = Piperylene3D.png
| ImageSize1 =
| ImageSize1 =
| IUPACName = 1,3-Pentadiene
| PIN = (3''E'')-Penta-1,3-diene
| OtherNames = Penta-1,3-diene
| OtherNames =
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| Abbreviations =
| Abbreviations =
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| index1_label = ''trans''
| CASNo = 504-60-9
| CASNo = 504-60-9
| CASNo1 = 2004-70-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FW963NF88B
| EINECS = 207-995-2
| EINECS = 207-995-2
| PubChem = 62204
| PubChem = 62204
⚫
| RTECS = RZ2464000
⚫
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| UNNumber = 1993 3295 1010
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 56020
| ChemSpiderID = 56020
| SMILES = C/C=C/C=C
| SMILES = C/C=C/C=C
| InChI = 1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
| InChI = 1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
| InChIKey = PMJHHCWVYXUKFD-SNAWJCMRBX
| InChIKey = PMJHHCWVYXUKFD-SNAWJCMRBX
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
| StdInChI = 1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PMJHHCWVYXUKFD-SNAWJCMRSA-N
| StdInChIKey = PMJHHCWVYXUKFD-SNAWJCMRSA-N
⚫
| RTECS =
| MeSHName =
| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI =
| ChEBI = 74165
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
| KEGG =
}}
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C =5|H=8
| C=5 | H=8
| MolarMass = 68.117 g/mol
| MolarMass = 68.117 g/mol
| Appearance = Colorless liquid
| Appearance = Colorless liquid
| Density = 0.683 g/cm<sup>3</sup>
| Density = 0.683 g/cm<sup>3</sup>
| MeltingPtC = -87
| MeltingPtC = -87
| MeltingPt_notes = E-isomer
| Melting_notes =
| BoilingPtC = 42
| BoilingPtC = 42
| BoilingPt_notes = E-isomer
| Boiling_notes =
| Solubility =
| Solubility =
| SolubleOther =
| SolubleOther =
Line 49: Line 53:
| pKb = }}
| pKb = }}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| EUClass =
| EUIndex =
| MainHazards =
| MainHazards =
| NFPA-H =
| NFPA-H =
| NFPA-F =
| NFPA-F =
| NFPA-R =
| NFPA-R =
| NFPA-O =
| NFPA-S =
| RPhrases = {{R11}} {{R36}} {{R37}} {{R38}}
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| SPhrases = {{S16}} {{S26}} {{S36}} {{S37}} {{S39}}
| HPhrases = {{H-phrases|225|304|315|319|335}}
| RSPhrases =
| 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}}
| FlashPtPrefix = <
| FlashPt = <
| FlashPtC = −30
| FlashPtC = −30
| AutoignitionPt =
| AutoignitionPt =
Line 67: Line 70:
}}
}}


'''Piperylene''' or '''1,3-pentadiene''' is an [[organic compound]] with the formula {{chem2|CH3\sCH\dCH\sCH\dCH2}}. It is a [[Volatile organic compound|volatile]], flammable [[hydrocarbon]]. It is one of the five [[positional isomer]]s of [[pentadiene]].
'''Piperylene''' is a volatile, flammable [[hydrocarbon]] consisting of a five carbon chain with two [[double bond]]s. It is obtained as a byproduct of [[ethylene]] production from crude oil.

==Reactions and occurrence==
Piperylene is 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>

Piperylene is the product of the decarboxylation of [[sorbic acid]], a common anti-mold agent.<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 used as a [[monomer]] in the manufacture 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] at Shell Chemicals. Retrieved 2009-05-19.</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>
Piperylene is colorless.<ref>http://msds.chem.ox.ac.uk/PI/piperylene.html</ref>


==See also==
==See also==
Line 78: Line 85:


==References==
==References==
{{Reflist}}
<references/>


[[Category:Dienes]]
[[Category:Alkadienes]]
[[Category:Hydrocarbons]]
[[Category:Conjugated dienes]]


{{hydrocarbon-stub}}
{{hydrocarbon-stub}}
{{Hydrocarbons}}

Latest revision as of 02:19, 12 October 2022

Piperylene[1]
Names
Preferred IUPAC name
(3E)-Penta-1,3-diene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.269 Edit this at Wikidata
EC Number
  • 207-995-2
RTECS number
  • RZ2464000
UNII
UN number 1993 3295 1010
  • InChI=1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+ ☒N
    Key: PMJHHCWVYXUKFD-SNAWJCMRSA-N ☒N
  • InChI=1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
    Key: PMJHHCWVYXUKFD-SNAWJCMRBX
  • C/C=C/C=C
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:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
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).
☒N verify (what is checkY☒N ?)

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.

Reactions and occurrence

[edit]

Piperylene is a typical diene. It forms a sulfolene upon treatment with sulfur dioxide.[2]

Piperylene is the product of the decarboxylation of sorbic acid, a common anti-mold agent.[3]

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.[4]

See also

[edit]

References

[edit]
  1. ^ Safety (MSDS) data for piperylene. Retrieved 2007-11-14.
  2. ^ Robert L. Frank, Raymond P. Seven (1949). "Isoprene Cyclic Sulfone". Organic Syntheses. 29: 59. doi:10.15227/orgsyn.029.0059.
  3. ^ 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)
  4. ^ Piperylene Archived 2009-05-13 at the Wayback Machine at Shell Chemicals. Retrieved 2009-05-19.
Stub icon

This article about a hydrocarbon is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Piperylene&oldid=1115558858"