2-Hexyne

2-Hexyne
Names
Preferred IUPAC name
Hex-2-yne
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.015 Edit this at Wikidata
EC Number
  • 212-117-6
UNII
  • InChI=1S/C6H10/c1-3-5-6-4-2/h3,5H2,1-2H3
    Key: MELUCTCJOARQQG-UHFFFAOYSA-N
  • CCCC#CC
Properties
C6H10
Molar mass 82.146 g·mol−1
Density 0.7317
Melting point −88 °C (−126 °F; 185 K)[1]
Boiling point 83.8 °C (182.8 °F; 356.9 K)[2]
1.4135
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H304, H315, H319
P210, P233, P240, P241, P242, P243, P264, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, P501
Related compounds
Related compounds
 3-Hexyne, 1-Hexyne
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Hexyne is an organic compound that belongs to the alkyne group. Just like its isomers, it also has the chemical formula of C6H10.

Reactions

2-Hexyne can be semihydrogenated to yield 2-hexene or fully hydrogenated to hexane.[3] With appropriate noble metal catalysts it can selectively form cis-2-hexene.[4]

2-Hexyne can act as a ligand on gold atoms.[5]

With strong sulfuric acid, the ketone 2-hexanone is produced. However this reaction also causes polymerization and charring.[6]

Under heat and pressure 2-hexyne polymerizes to linear oligomers and polymers. This can be hastened by some catalysts such as molybdenum pentachloride with tetraphenyl tin. However Ziegler–Natta catalysts have no action as the triple bond is hindered.[7]

References

  1. ^ Campbell, Kenneth N.; Eby, Lawrence T. (October 1941). "The Reduction of Multiple Carbon—Carbon Bonds. III. Further Studies on the Preparation of Olefins from Acetylenes 1,2". Journal of the American Chemical Society. 63 (10): 2683–2685. doi:10.1021/ja01855a050.
  2. ^ Hennion, G. F.; Sheehan, J. J. (June 1949). "1,2-Hexadiene". Journal of the American Chemical Society. 71 (6): 1964–1966. doi:10.1021/ja01174a017.
  3. ^ Ulan, Judith G.; Maier, Wilhelm F. (September 1989). "Mechanism of 2-hexyne hydrogenation on heterogeneous palladium". Journal of Molecular Catalysis. 54 (2): 243–261. doi:10.1016/0304-5102(89)80220-2.
  4. ^ Schrock, Richard R.; Osborn, John A. (April 1976). "Catalytic hydrogenation using cationic rhodium complexes. II. The selective hydrogenation of alkynes to cis olefins". Journal of the American Chemical Society. 98 (8): 2143–2147. doi:10.1021/ja00424a021.
  5. ^ Zuccaccia, Daniele; Belpassi, Leonardo; Rocchigiani, Luca; Tarantelli, Francesco; Macchioni, Alceo (5 April 2010). "A Phosphine Gold(I) π-Alkyne Complex: Tuning the Metal−Alkyne Bond Character and Counterion Position by the Choice of the Ancillary Ligand". Inorganic Chemistry. 49 (7): 3080–3082. doi:10.1021/ic100093n. PMID 20222666.
  6. ^ Thomas, Robert J.; Campbell, Kenneth N.; Hennion, G. F. (March 1938). "Catalytic Hydration of Alkylacetylenes 1". Journal of the American Chemical Society. 60 (3): 718–720. doi:10.1021/ja01270a061.
  7. ^ Higashimura, Toshinobu; Deng, Yun Xiang; Masuda, Toshio (March 1982). "Polymerization of 2-hexyne and higher 2-alkynes catalyzed by MoCl 5 Ph 4 Sn and WCl 6 Ph 4 Sn 1". Macromolecules. 15 (2): 234–238. Bibcode:1982MaMol..15..234H. doi:10.1021/ma00230a005.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.