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HandWiki. 1,3-Butadiene. Encyclopedia. Available online: https://encyclopedia.pub/entry/29501 (accessed on 16 September 2026).
HandWiki. 1,3-Butadiene. Encyclopedia. Available at: https://encyclopedia.pub/entry/29501. Accessed September 16, 2026.
HandWiki. "1,3-Butadiene" Encyclopedia, https://encyclopedia.pub/entry/29501 (accessed September 16, 2026).
HandWiki. (2022, October 17). 1,3-Butadiene. In Encyclopedia. https://encyclopedia.pub/entry/29501
HandWiki. "1,3-Butadiene." Encyclopedia. Web. 17 October, 2022.
1,3-Butadiene
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The content is sourced from: https://handwiki.org/wiki/Chemistry:1,3-Butadiene

1,3-Butadiene is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a monomer in the production of synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene. Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance.

cumulated diene 12-butadiene 13-butadiene

References

  1. Caventou, E. (1863). "Ueber eine mit dem zweifach-gebromten Brombutylen isomere Verbindung und über die bromhaltigen Derivate des Brombutylens". Justus Liebigs Annalen der Chemie 127: 93–97. doi:10.1002/jlac.18631270112.  https://dx.doi.org/10.1002%2Fjlac.18631270112
  2. Armstrong, H. E.; Miller, A. K. (1886). "The decomposition and genesis of hydrocarbons at high temperatures. I. The products of the manufacture of gas from petroleum". J. Chem. Soc. 49: 74–93. doi:10.1039/CT8864900074.  https://dx.doi.org/10.1039%2FCT8864900074
  3. Simple Things Won't Save the Earth, J. Robert Hunter https://books.google.com/books?id=7yHlAgAAQBAJ&pg=PA23&dq=butadiene+dependence+on+natural+rubber&hl=pt-BR&sa=X&redir_esc=y#v=onepage&q=butadiene%20dependence%20on%20natural%20rubber&f=false
  4. Sun, H.P. Wristers, J.P. (1992). Butadiene. In J.I. Kroschwitz (Ed.), Encyclopedia of Chemical Technology, 4th ed., vol. 4, pp. 663–690. New York: John Wiley & Sons.
  5. Beychok, M.R. and Brack, W.J., "First Postwar Butadiene Plant", Petroleum Refiner, June 1957.
  6. Herbert, Vernon, "Synthetic Rubber: A Project That Had to Succeed", Greenwood Press, 1985, ISBN:0-313-24634-3
  7. J. Grub, E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2.  https://dx.doi.org/10.1002%2F14356007.a04_431.pub2
  8. Kirshenbaum, I. (1978). Butadiene. In M. Grayson (Ed.), Encyclopedia of Chemical Technology, 3rd ed., vol. 4, pp. 313–337. New York: John Wiley & Sons.
  9. E. B. Hershberg, John R. Ruhoff (1937). "1,3-Butadiene". Org. Synth. 17: 25. doi:10.15227/orgsyn.017.0025.  https://dx.doi.org/10.15227%2Forgsyn.017.0025
  10. "4-Vinylcyclohexene". IARC. http://monographs.iarc.fr/ENG/Monographs/vol60/mono60-13.pdf. Retrieved 2009-04-19. 
  11. J. E. Nyström, T. Rein, J. E. Bäckvall (1989). "1,4-Functionalization of 1,3-Dienes via Palladium-Catalyzed Chloroacetoxylation and Allylic Amination: 1-Acetoxy-4-diethylamino-2-butene and 1-Acetoxy-4-benzylamino-2-butene". Org. Synth. 67: 105. doi:10.15227/orgsyn.067.0105.  https://dx.doi.org/10.15227%2Forgsyn.067.0105
  12. Arthur C. Cope, Elbert C. Herrick (1950). "cis-Δ4-Tetrahydrophthalic Anhydride". Org. Synth. 50: 93. doi:10.15227/orgsyn.030.0093.  https://dx.doi.org/10.15227%2Forgsyn.030.0093
  13. Reiss, Guido J. (2010). "Redetermination of (η4-s-cis-1,3-butadiene)tricarbonyliron(0)". Acta Crystallographica Section E 66: m1369. doi:10.1107/S1600536810039218.  http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3009352
  14. "NPI sheet". http://www.npi.gov.au/database/substance-info/profiles/16.html. 
  15. Grosse, Yann; Baan, Robert; Straif, Kurt; Secretan, Béatrice; El Ghissassi, Fatiha; Bouvard, Véronique; Altieri, Andrea; Cogliano, Vincent (2008). "Carcinogenicity of 1,3-butadiene, ethylene oxide, vinyl chloride, vinyl fluoride, and vinyl bromide" (in English). The Lancet Oncology 8 (8): 679–680. doi:10.1016/S1470-2045(07)70235-8. ISSN 1470-2045. https://www.thelancet.com/journals/lanonc/article/PIIS1470204507702358/fulltext. 
  16. http://www.atsdr.cdc.gov/substances/toxsubstance.asp?toxid=81
  17. Health Effects https://www.osha.gov/SLTC/butadiene/index.html
  18. http://www.nrdc.org/health/diseaseclusters/
  19. Fowles, J; Dybing, E (4 September 2003). "Application of toxicological risk assessment principles to the chemical constituents of cigarette smoke". Institute of Environmental Science and Research (New Zealand: Centers for Disease Control and Prevention) 12 (4): 424–430. doi:10.1136/tc.12.4.424. PMID 14660781. PMC 1747794. http://tobaccocontrol.bmj.com/content/12/4/424. Retrieved 12 October 2014. 
  20. Landrigan, PJ (1990). "Critical assessment of epidemiologic studies on the human carcinogenicity of 1,3-butadiene". Environmental Health Perspectives 86: 143–147. doi:10.1289/ehp.9086143. PMID 2205484.  http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1567758
  21. "1,3-Butadiene CAS No. 106-99-0". Report on Carcinogens. http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s025buta.pdf. 
  22. Melnick, Ronald L.; Kohn, Michael C. (1995). "Mechanistic data indicate that 1,3-butadiene is a human carcinogen". Carcinogenesis 16 (2): 157–63. doi:10.1093/carcin/16.2.157. PMID 7859343.  https://dx.doi.org/10.1093%2Fcarcin%2F16.2.157
  23. "Archived copy". http://www.environment-agency.gov.uk/business/topics/pollution/27.aspx. 
  24. EPA website http://www.epa.gov/ttn/atw/hlthef/butadien.html
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