Decene

from Wikipedia, the free encyclopedia

In chemistry, the decenes belong to the group of alkenes . It consists of several isomeric compounds with the empirical formula C 10 H 20 and a double bond . Theoretically there are 377 structural isomers .

properties

The linear (unbranched) representatives are 1-decene , 2-decene , 3-decene , 4-decene and 5-decene .

linear decene
Surname 1-decene 2-decene 3-decene 4-decene 5-decene
other names Decylene dec
-1-en 		Dec-2-en Dec-3-en Dec-4-en Dec-5-en
Structural formula Dec-1-ene 200.svg (E) -dec-2-ene.svg( trans )

(Z) -dec-2-ene.svg( cis ) 		(Z) -3-decene structural formula V1.svg( cis )

(E) -3-decene structural formula V1.svg( trans ) 		(Z) -4-decene structural formula V1.svg( cis )

(E) -4-decene structural formula V1.svg( trans ) 		(Z) -5-decade structural formula V1.svg( cis )

(E) -5-decade structural formula V1.svg( trans )
CAS number 25339-53-1
872-05-9 6816-17-7
20348-51-0 ( cis )
20063-97-2 ( trans )		 19398-37-9
19398-86-8 ( cis )
19150-21-1 ( trans )		 19689-18-0
19398-88-0 ( cis )
19398-89-1 ( trans )		 19689-19-1
7433-78-5 ( cis )
7433-56-9 ( trans )
PubChem 13381 32899 140483 88039 23916
Molecular formula C 10 H 20
Molar mass 140.27 g mol −1
Physical state liquid
Brief description colorless liquid
with a characteristic odor 		colorless liquid colorless liquid
Melting point −66.3 ° C
  • −112 ° C ( cis )
  • −73 ° C ( trans )
boiling point 172 ° C
  • 174 ° C ( cis )
  • 173 ° C ( trans )
 171 ° C
  • 170 ° C ( cis )
  • 171 ° C ( trans )
density 0.74 g cm −3 0.76 g cm −3 0.76 g cm −3 0.74 g cm −3 0.74 g cm −3
solubility
  • practically insoluble in water
  • soluble in ethanol
GHS
labeling
02 - Highly / extremely flammable 08 - Dangerous to health 09 - Dangerous for the environment
02 - Highly / extremely flammable 08 - Dangerous to health
02 - Highly / extremely flammable 07 - Warning
H and P phrases 226-304-315-411 226-304 226-315-319-335
273-301 + 330 + 331-302 + 352-331 210-233-240-280-301 + 310-331
303 + 361 + 353-370 + 378-403 + 235-405-501 		261-305 + 351 + 338

Extraction and presentation

Linear decenes can be prepared by the partial reduction of alkylacetylenes, with only the trans form (for example in the case of 5-decene) being formed , depending on the reaction conditions . The cis - olefins , however, can be prepared from the trans olefins by chlorination of the latter, elimination of hydrogen chloride , followed by dechlorination of Chlorolefins with sodium in liquid ammonia are produced. In addition, 1-decene can be isomerized almost completely to decenes with internal double bonds by heating with sodium and a little chlorotoluene . Various other synthesis variants are also known. They are also formed in the pyrolysis of organic compounds such as 1-chlorodecane , 1-Fluordecan , 1-Bromodecane and triolein .

use

1-Decene is used as a comonomer and as an intermediate in the production of a number of other compounds for flavors, perfumes, pharmaceuticals, colors, oils and resins. The hydrogenated poly-1-decene (E 907) synthesized from the compound is approved as a coating agent for sugar confectionery and dried fruits .

Occurrence

1- and 2-decene are found in cigarette smoke , 1- and 4-decene in shale oils .

Individual evidence

  1. ↑ Dieter Wolber: Chemistry is not that difficult ... Basics . BoD - Books on Demand, 2014, ISBN 978-3-7322-8509-9 , pp. 281 ( limited preview in Google Book search).
  2. ^ Alkene - OEIS , accessed May 17, 2017.
  3. ↑ a b c d e f Entry for CAS no. 872-05-9 in the GESTIS substance database of the IFA , accessed on September 12, 2013(JavaScript required) .
  4. ↑ a b Entry on cis-2-decene at TCI Europe, accessed on May 16, 2017.
  5. ↑ a b Data sheet trans-5-Decene, 99% from Sigma-Aldrich , accessed on May 16, 2017 ( PDF ).
  6. ↑ a b c d e f g h William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 142 ( limited preview in Google Book search).
  7. ↑ David R. Lide, George William Anthony Milne: Handbook of data on common organic compounds . CRC Press, 1995, ISBN 0-8493-0404-0 , pp. 984 ( limited preview in Google Book Search).
  8. ^ A b c Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2008, ISBN 978-0-8155-1990-4 , pp. 161 ( limited preview in Google Book search).
  9. ^ Richard J. Lewis, Sr .: Hawley's Condensed Chemical Dictionary . 15th edition. Wiley-Interscience, 2007, ISBN 978-0-471-76865-4 (English).
  10. ^ F. Asinger: Mono-Olefins Chemistry and Technology . Elsevier, 2013, ISBN 978-1-4831-6096-2 , pp. 202, 1036 ( limited preview in Google Book search).
  11. ^ Carlyle J. Stehman, Newell C. Cook, William C. Percival, Frank C. Whitmore: Hydrocarbons. XI. Synthesis of Nineteen Decenes. In: Journal of the American Chemical Society . 72, 1950, p. 4163, doi: 10.1021 / ja01165a089 .
  12. ↑ GV Isagulyants, OD Sterligov, AP Barkova, IP Yakovlev, MA Panfilova, LK Maslova, NA Eliseev: Composition of olefin FORMED in the dehydrogenation of n-decane over aluminum-platinum catalysts. In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 33, 1984, p. 1869, doi: 10.1007 / BF00948632 .
  13. ^ Serban C. Moldoveanu: Pyrolysis of Organic Molecules Applications to Health and Environmental Issues . Elsevier, 2009, ISBN 978-0-08-093215-6 , pp. 249 ( limited preview in Google Book search).
  14. ↑ OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 1-Decene , accessed on November 6, 2014.
  15. ^ Entry on Decene in the Hazardous Substances Data Bank , accessed June 3, 2017.
  16. ↑ Sarastro GmbH: Ordinance on the admission of additives to food to ... BoD - Books on Demand, 2012, ISBN 3-86471-742-6 , p. 46 ( limited preview in Google Book search).
  17. ↑ Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke, Second Edition . CRC Press, 2016, ISBN 978-1-4665-1552-9 , pp. 18 ( limited preview in Google Book search).
  18. ^ Thomas Aczel: Mass Spectrometric Characterization of Shale Oils A Symposium . ASTM International, 1986, ISBN 978-0-8031-0467-9 , pp. 11 ( limited preview in Google Book search).