Undecane

Strukturformel von 2,2,3,3,4,4,-Hexamethylpentan, einem Isomer von Undecan
Strukturformel von 2,2,3,3,4,4,-Hexamethylpentan, einem Isomer von Undecan

Die Undecane bilden eine Stoffgruppe aus der Gruppe der Alkane. Namensgeber ist der lineare Vertreter Undecan. Die Undecane umfassen theoretisch 159 konstitutionsisomere bzw. 345 konstitutions- und konfigurationsisomere Verbindungen mit der Summenformel C11H24.[1][2] In öffentlich verfügbaren Datenbanken werden (Stand März 2024) zwischen 62 und 177 tatsächlich bekannte Isomere geführt.[3][4]

Verwendung

Die Isomere des Undecans finden in der Trennung von Alkylphenolen mittels Azeotroprektifikation Verwendung, bei der die Isomere als Schleppmittel benutzt werden.[5]

Konstitutionsisomere

Die folgende Tabelle gibt einen Überblick über alle theoretisch möglichen konstitutionsisomeren Undecane, gruppiert nach Anzahl der Kohlenstoffatome in der Hauptkette bzw. nach den Substituenten:

Substituenten Anzahl der C-Atome in der Hauptkette
11 10 9 8 7 6 5
--- n-Undecan
Methyl

2-Methyldecan
3-Methyldecan
4-Methyldecan
5-Methyldecan

2,2-Dimethylnonan
2,3-Dimethylnonan
2,4-Dimethylnonan
2,5-Dimethylnonan
2,6-Dimethylnonan
2,7-Dimethylnonan
2,8-Dimethylnonan
3,3-Dimethylnonan
3,4-Dimethylnonan
3,5-Dimethylnonan
3,6-Dimethylnonan
3,7-Dimethylnonan
4,4-Dimethylnonan
4,5-Dimethylnonan
4,6-Dimethylnonan
5,5-Dimethylnonan

2,2,3-Trimethyloctan
2,2,4-Trimethyloctan
2,2,5-Trimethyloctan
2,2,6-Trimethyloctan
2,2,7-Trimethyloctan
2,3,3-Trimethyloctan
2,3,4-Trimethyloctan
2,3,5-Trimethyloctan
2,3,6-Trimethyloctan
2,3,7-Trimethyloctan
2,4,4-Trimethyloctan
2,4,5-Trimethyloctan
2,4,6-Trimethyloctan
2,4,7-Trimethyloctan
2,5,5-Trimethyloctan
2,5,6-Trimethyloctan
2,6,6-Trimethyloctan
3,3,4-Trimethyloctan
3,3,5-Trimethyloctan
3,3,6-Trimethyloctan
3,4,4-Trimethyloctan
3,4,5-Trimethyloctan
3,4,6-Trimethyloctan
3,5,5-Trimethyloctan
4,4,5-Trimethyloctan

2,2,3,3-Tetramethylheptan
2,2,3,4-Tetramethylheptan
2,2,3,5-Tetramethylheptan
2,2,3,6-Tetramethylheptan
2,2,4,4-Tetramethylheptan
2,2,4,5-Tetramethylheptan
2,2,4,6-Tetramethylheptan
2,2,5,5-Tetramethylheptan
2,2,5,6-Tetramethylheptan
2,2,6,6-Tetramethylheptan
2,3,3,4-Tetramethylheptan
2,3,3,5-Tetramethylheptan
2,3,3,6-Tetramethylheptan
2,3,4,4-Tetramethylheptan
2,3,4,5-Tetramethylheptan
2,3,4,6-Tetramethylheptan
2,3,5,5-Tetramethylheptan
2,3,5,6-Tetramethylheptan
2,4,4,5-Tetramethylheptan
2,4,4,6-Tetramethylheptan
2,4,5,5-Tetramethylheptan
3,3,4,4-Tetramethylheptan
3,3,4,5-Tetramethylheptan
3,3,5,5-Tetramethylheptan
3,4,4,5-Tetramethylheptan

2,2,3,3,4-Pentamethylhexan
2,2,3,3,5-Pentamethylhexan
2,2,3,4,4-Pentamethylhexan
2,2,3,4,5-Pentamethylhexan
2,2,3,5,5-Pentamethylhexan
2,2,4,4,5-Pentamethylhexan
2,3,3,4,4-Pentamethylhexan
2,3,3,4,5-Pentamethylhexan

2,2,3,3,4,4-Hexamethylpentan

Ethyl

3-Ethylnonan
4-Ethylnonan
5-Ethylnonan

3,3-Diethylheptan
3,4-Diethylheptan
3,5-Diethylheptan
4,4-Diethylheptan

Ethyl
und
Methyl

3-Ethyl-2-methyloctan
3-Ethyl-3-methyloctan
3-Ethyl-4-methyloctan
3-Ethyl-5-methyloctan
3-Ethyl-6-methyloctan
4-Ethyl-2-methyloctan
4-Ethyl-3-methyloctan
4-Ethyl-4-methyloctan
4-Ethyl-5-methyloctan
5-Ethyl-2-methyloctan
5-Ethyl-3-methyloctan
6-Ethyl-2-methyloctan

3-Ethyl-2,2-dimethylheptan
3-Ethyl-2,3-dimethylheptan
3-Ethyl-2,4-dimethylheptan
3-Ethyl-2,5-dimethylheptan
3-Ethyl-2,6-dimethylheptan
3-Ethyl-3,4-dimethylheptan
3-Ethyl-3,5-dimethylheptan
3-Ethyl-4,4-dimethylheptan
3-Ethyl-4,5-dimethylheptan
4-Ethyl-2,2-dimethylheptan
4-Ethyl-2,3-dimethylheptan
4-Ethyl-2,4-dimethylheptan
4-Ethyl-2,5-dimethylheptan
4-Ethyl-2,6-dimethylheptan
4-Ethyl-3,3-dimethylheptan
4-Ethyl-3,4-dimethylheptan
4-Ethyl-3,5-dimethylheptan
5-Ethyl-2,2-dimethylheptan
5-Ethyl-2,3-dimethylheptan
5-Ethyl-2,4-dimethylheptan
5-Ethyl-2,5-dimethylheptan
5-Ethyl-3,3-dimethylheptan

3-Ethyl-2,2,3-trimethylhexan
3-Ethyl-2,2,4-trimethylhexan
3-Ethyl-2,2,5-trimethylhexan
3-Ethyl-2,3,4-trimethylhexan
3-Ethyl-2,3,5-trimethylhexan
3-Ethyl-2,4,4-trimethylhexan
3-Ethyl-2,4,5-trimethylhexan
3-Ethyl-3,4,4-trimethylhexan
4-Ethyl-2,2,3-trimethylhexan
4-Ethyl-2,2,4-trimethylhexan
4-Ethyl-2,2,5-trimethylhexan
4-Ethyl-2,3,3-trimethylhexan
4-Ethyl-2,3,4-trimethylhexan
3,3-Diethyl-2-methylhexan
3,3-Diethyl-4-methylhexan
3,4-Diethyl-2-methylhexan
3,4-Diethyl-3-methylhexan
4,4-Diethyl-2-methylhexan

3-Ethyl-2,2,3,4-tetramethylpentan
3-Ethyl-2,2,4,4-tetramethylpentan
3,3-Diethyl-2,2-dimethylpentan
3,3-Diethyl-2,4-dimethylpentan

Propyl 4-Propyloctan
1-Methylethyl
(=Isopropyl) 		4-(1-Methylethyl)octan
Methyl
und
1-Methylethyl
(=Isopropyl)

2-Methyl-3-(1-methylethyl)heptan
2-Methyl-4-(1-methylethyl)heptan
3-Methyl-4-(1-methylethyl)heptan
4-Methyl-4-(1-methylethyl)heptan

2,2-Dimethyl-3-(1-methylethyl)hexan
2,3-Dimethyl-3-(1-methylethyl)hexan
2,4-Dimethyl-3-(1-methylethyl)hexan
2,5-Dimethyl-3-(1-methylethyl)hexan

2,2,4-Trimethyl-3-(1-methylethyl)pentan
2,3,4-Trimethyl-3-(1-methylethyl)pentan

Methyl
und
Propyl

2-Methyl-4-propylheptan
3-Methyl-4-propylheptan
4-Methyl-4-propylheptan

Butyl 4-tert-Butylheptan

Einzelnachweise

  1. ↑ Sascha Kurz: Anzahl von Strukturisomeren der Alkane. Universität Bayreuth, 11. Mai 2005 (uni-bayreuth.de [PDF]).
  2. ↑ Number of n-node unrooted steric quartic trees; number of n-carbon alkanes C(n)H(2n+2) taking stereoisomers into account. In: On-Line Encyclopedia of Integer Sequences. Abgerufen am 21. März 2024.
  3. ↑ Chemical Identifier Search | c11h24. Abgerufen am 14. März 2024.
  4. ↑ NIST Office of Data and Informatics: Search Results. Abgerufen am 14. März 2024 (englisch).
  5. ↑ Patent US4349419: Process for separation of alkyl phenols by azeotropic distillation. Veröffentlicht am 14. September 1982, Erfinder: Kazunori Takahata, Katsuo Taniguchi, Tadaaki Fujimoto.‌

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