1,7-Octadiene

Last updated
1,7-Octadiene
1,7-Octadiene.svg
Names
Preferred IUPAC name
Octa-1,7-diene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.959 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 223-054-9
PubChem CID
RTECS number
  • RG5250000
UNII
UN number 2309
  • InChI=1S/C8H14/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-8H2
    Key: XWJBRBSPAODJER-UHFFFAOYSA-N
  • C=CCCCCC=C
Properties
C8H14
Molar mass 110.200 g·mol−1
AppearanceColorless liquid
Density 0.746 g/mL at 25 °C
Boiling point 114–121 °C (237–250 °F; 387–394 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H225, H304, H410, H412
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Related compounds
Related alkenes
and dienes
Isoprene
Chloroprene
Related compounds
 Butane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,7-Octadiene is an organic compound with the formula (CH2=CHCH2CH2)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. [1]

Contents

Conversion of butadiene to 1,10-difunctionalized decanes OctadieneToDecanes.svg
Conversion of butadiene to 1,10-difunctionalized decanes

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. [2]

Formation of dimethyloctadienes Dimethyloctadienes.svg
Formation of dimethyloctadienes

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. [3] It undergoes ring-closing metathesis to give cyclooctene. [4] Plasma polymerized 1,7-octadiene films deposited on silica can produce particles with tuned hydrophobicity. [5]

References

  1. ↑ Dahlmann, Marc; Grub, Joachim; Löser, Eckhard (2011). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–24. doi:10.1002/14356007.a04_431.pub2. ISBN   978-3-527-30673-2.
  2. ↑ Sagorin, Gilles; Cazeils, Emmanuel; Basset, Jean-François; Reiter, Maud (2021). "From Pine to Perfume". CHIMIA. 75 (9): 780–787. doi:10.2533/chimia.2021.780. PMID   34526184.
  3. ↑ Fustero, S; Bello, P; Miró, J; Simón, A; del Pozo, C (27 August 2012). "1,7-octadiene-assisted tandem multicomponent cross-enyne metathesis (CEYM)-Diels-Alder reactions: a useful alternative to Mori's conditions". Chemistry: A European Journal. 18 (35): 10991–7. doi:10.1002/chem.201200835. PMID   22851514.
  4. ↑ Weskamp, Thomas; Schattenmann, Wolfgang C.; Spiegler, Michael; Herrmann, Wolfgang A. (1998). "A Novel Class of Ruthenium Catalysts for Olefin Metathesis". Angewandte Chemie International Edition. 37 (18): 2490–2493. doi:10.1002/(sici)1521-3773(19981002)37:18<2490::aid-anie2490>3.0.co;2-x. PMID   29711340.
  5. ↑ Akhavan, Behnam; Jarvis, Karyn; Majewski, Peter (November 2013). "Tuning the hydrophobicity of plasma polymer coated silica particles". Powder Technology. 249: 403–411. doi:10.1016/j.powtec.2013.09.018.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.