1,7-Octadiene
{{chembox
| Watchedfields =
| verifiedrevid =
| Name = 1,7-Octadiene
| ImageFile = 1,7-Octadiene.svg
| PIN = Octa-1,7-diene
| OtherNames =
|Section1={{Chembox Identifiers
| UNII_Ref =
| UNII = N4H29T34J2
| SMILES = C=CCCCCC=C
| ChEBI = 183652
| ChemSpiderID = 18338
| KEGG =
| InChI = InChI=1S/C8H14/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-8H2
| InChIKey = XWJBRBSPAODJER-UHFFFAOYSA-N
| ChEMBL =
| StdInChI_Ref =
| StdInChI =
| StdInChIKey_Ref =
| StdInChIKey =
| CASNo_Ref =
| CASNo = 3710-30-3
| UNNumber = 2309
| RTECS = RG5250000
| PubChem = 19460
| EINECS = 223-054-9
}}
|Section2={{Chembox Properties
| C=8|H=14
| Appearance = Colorless liquid
| Odor =
| Density = 0.746 g/mL at 25 °C
| Solubility =
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| MeltingPtC =
| MeltingPt_notes =
| BoilingPtC = 114-121
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|Section3={{Chembox Structure
| Dipole =
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|Section7={{Chembox Hazards
| ExternalSDS =
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| FlashPtC =
| FlashPt_notes =
| AutoignitionPtC =
| ExploLimits =
| GHSPictograms = {{GHS02}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|304|410|412}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}
| NFPA-H = | NFPA-F = | NFPA-R =
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|Section8={{Chembox Related
| OtherFunction_label = alkenes
and dienes
| OtherFunction = Isoprene
Chloroprene
| OtherCompounds = Butane
}}
}}
1,7-Octadiene is an organic compound with the formula {{chem2|(CH2\dCHCH2CH2)2}}. It is a colorless liquid that serves as a precursor to specialty polymers. It arises commercially by the dimerization of butadiene in the presence of hydrogen. Some of the 1,6-octadiene is also formed. 1,7-Octadiene can be converted to the diol by hydroformylation followed by hydrogenation of the dialdehyde. In a related process, 1,7-Octadiene undergoes hydrocyanation to give dinitrile, which can be hydrogenated to give 1,10-diaminodecane.{{cite book |doi=10.1002/14356007.a04_431.pub2 |chapter=Butadiene |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Dahlmann |first1=Marc |last2=Grub |first2=Joachim |last3=Löser |first3=Eckhard |pages=1–24 |isbn=978-3-527-30673-2 }}
Dimethyloctadienes
Structurally related octadienes bearing two methyl groups are of commercial interest. Such compounds are produced by pyrolysis of pinane, which is abundantly available from terpentine or related wood-derived chemicals.{{cite journal |doi=10.2533/chimia.2021.780 |title=From Pine to Perfume |date=2021 |last1=Sagorin |first1=Gilles |last2=Cazeils |first2=Emmanuel |last3=Basset |first3=Jean-François |last4=Reiter |first4=Maud |journal=CHIMIA |volume=75 |issue=9 |pages=780–787 |pmid=34526184 |doi-access=free }}
Research
The diene has also been the subject of many research papers. For example, with ethylene it undergoes a cross-enyne metathesis Diels–Alder reaction.{{cite journal |last1=Fustero |first1=S |last2=Bello |first2=P |last3=Miró |first3=J |last4=Simón |first4=A |last5=del Pozo |first5=C |title=1,7-octadiene-assisted tandem multicomponent cross-enyne metathesis (CEYM)-Diels-Alder reactions: a useful alternative to Mori's conditions |journal=Chemistry: A European Journal |date=27 August 2012 |volume=18 |issue=35 |pages=10991–7 |pmid=22851514 |doi=10.1002/chem.201200835}} It undergoes ring-closing metathesis to give cyclooctene.{{cite journal |doi=10.1002/(sici)1521-3773(19981002)37:18<2490::aid-anie2490>3.0.co;2-x |title=A Novel Class of Ruthenium Catalysts for Olefin Metathesis |date=1998 |last1=Weskamp |first1=Thomas |last2=Schattenmann |first2=Wolfgang C. |last3=Spiegler |first3=Michael |last4=Herrmann |first4=Wolfgang A. |journal=Angewandte Chemie International Edition |volume=37 |issue=18 |pages=2490–2493 |pmid=29711340 }} Plasma polymerized 1,7-octadiene films deposited on silica can produce particles with tuned hydrophobicity.{{cite journal |last1=Akhavan |first1=Behnam |last2=Jarvis |first2=Karyn |last3=Majewski |first3=Peter |title=Tuning the hydrophobicity of plasma polymer coated silica particles |journal=Powder Technology |date=November 2013 |volume=249 |pages=403–411 |doi=10.1016/j.powtec.2013.09.018}}
References
External links
- {{cite web |url=http://www.sigmaaldrich.com/catalog/product/aldrich/o2501?lang=en |title=1,7-Octadiene |publisher=Sigma-Aldrich |accessdate=20 April 2016}}
{{DEFAULTSORT:Octadiene, 1, 7-}}
{{Hydrocarbons}}
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