Dodecane

aus Wikipedia, der freien Enzyklopädie
Zur Navigation springen Zur Suche springen

Die Dodecane sind eine Stoffgruppe aus der Gruppe der Alkane. Sie besteht aus 355 isomeren Verbindungen mit der Summenformel C12H26.[1]

Der lineare Vertreter ist das n-Dodecan.

Die folgende Tabelle gibt einen Überblick über alle konstitutionsisomeren Dodecane, gruppiert nach Anzahl der Kohlenstoffatome in der Hauptkette bzw. nach den Substitutenten:[2]

Substituenten Anzahl der C-Atome in der Hauptkette
12 11 10 9 8 7 6 5
--- n-Dodecan
Methyl

2-Methylundecan
3-Methylundecan
4-Methylundecan
5-Methylundecan
6-Methylundecan

2,2-Dimethyldecan
2,3-Dimethyldecan
2,4-Dimethyldecan
2,5-Dimethyldecan
2,6-Dimethyldecan
2,7-Dimethyldecan
2,8-Dimethyldecan
2,9-Dimethyldecan
3,3-Dimethyldecan
3,4-Dimethyldecan
3,5-Dimethyldecan
3,6-Dimethyldecan
3,7-Dimethyldecan
3,8-Dimethyldecan
4,4-Dimethyldecan
4,5-Dimethyldecan
4,6-Dimethyldecan
4,7-Dimethyldecan
5,5-Dimethyldecan
5,6-Dimethyldecan

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

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

2,2,3,3,4-Pentamethylheptan
2,2,3,3,5-Pentamethylheptan
2,2,3,3,6-Pentamethylheptan
2,2,3,4,4-Pentamethylheptan
2,2,3,4,5-Pentamethylheptan
2,2,3,4,6-Pentamethylheptan
2,2,3,5,5-Pentamethylheptan
2,2,3,5,6-Pentamethylheptan
2,2,3,6,6-Pentamethylheptan
2,2,4,4,5-Pentamethylheptan
2,2,4,4,6-Pentamethylheptan
2,2,4,5,5-Pentamethylheptan
2,2,4,5,6-Pentamethylheptan
2,2,4,6,6-Pentamethylheptan
2,2,5,5,6-Pentamethylheptan
2,3,3,4,4-Pentamethylheptan
2,3,3,4,5-Pentamethylheptan
2,3,3,4,6-Pentamethylheptan
2,3,3,5,5-Pentamethylheptan
2,3,3,5,6-Pentamethylheptan
2,3,4,4,5-Pentamethylheptan
2,3,4,4,6-Pentamethylheptan
2,3,4,5,5-Pentamethylheptan
2,3,4,5,6-Pentamethylheptan
2,4,4,5,5-Pentamethylheptan
3,3,4,4,5-Pentamethylheptan
3,3,4,5,5-Pentamethylheptan

2,2,3,3,4,4-Hexamethylhexan
2,2,3,3,4,5-Hexamethylhexan
2,2,3,3,5,5-Hexamethylhexan
2,2,3,4,4,5-Hexamethylhexan
2,2,3,4,5,5-Hexamethylhexan
2,3,3,4,4,5-Hexamethylhexan

Ethyl

3-Ethyldecan
4-Ethyldecan
5-Ethyldecan

3,3-Diethyloctan
3,4-Diethyloctan
3,5-Diethyloctan
3,6-Diethyloctan
4,4-Diethyloctan
4,5-Diethyloctan

3,3,4-Triethylhexan

Ethyl
und
Methyl

3-Ethyl-2-methylnonan
3-Ethyl-3-methylnonan
3-Ethyl-4-methylnonan
3-Ethyl-5-methylnonan
3-Ethyl-6-methylnonan
3-Ethyl-7-methylnonan
4-Ethyl-2-methylnonan
4-Ethyl-3-methylnonan
4-Ethyl-4-methylnonan
4-Ethyl-5-methylnonan
4-Ethyl-6-methylnonan
5-Ethyl-2-methylnonan
5-Ethyl-3-methylnonan
5-Ethyl-4-methylnonan
5-Ethyl-5-methylnonan
6-Ethyl-2-methylnonan
6-Ethyl-3-methylnonan
7-Ethyl-2-methylnonan

3-Ethyl-2,2-dimethyloctan
3-Ethyl-2,3-dimethyloctan
3-Ethyl-2,4-dimethyloctan
3-Ethyl-2,5-dimethyloctan
3-Ethyl-2,6-dimethyloctan
3-Ethyl-2,7-dimethyloctan
3-Ethyl-3,4-dimethyloctan
3-Ethyl-3,5-dimethyloctan
3-Ethyl-3,6-dimethyloctan
3-Ethyl-4,4-dimethyloctan
3-Ethyl-4,5-dimethyloctan
3-Ethyl-4,6-dimethyloctan
3-Ethyl-5,5-dimethyloctan
4-Ethyl-2,2-dimethyloctan
4-Ethyl-2,3-dimethyloctan
4-Ethyl-2,4-dimethyloctan
4-Ethyl-2,5-dimethyloctan
4-Ethyl-2,6-dimethyloctan
4-Ethyl-2,7-dimethyloctan
4-Ethyl-3,3-dimethyloctan
4-Ethyl-3,4-dimethyloctan
4-Ethyl-3,5-dimethyloctan
4-Ethyl-3,6-dimethyloctan
4-Ethyl-4,5-dimethyloctan
5-Ethyl-2,2-dimethyloctan
5-Ethyl-2,3-dimethyloctan
5-Ethyl-2,4-dimethyloctan
5-Ethyl-2,5-dimethyloctan
5-Ethyl-2,6-dimethyloctan
5-Ethyl-3,3-dimethyloctan
5-Ethyl-3,4-dimethyloctan
5-Ethyl-3,5-dimethyloctan
5-Ethyl-4,4-dimethyloctan
6-Ethyl-2,2-dimethyloctan
6-Ethyl-2,3-dimethyloctan
6-Ethyl-2,4-dimethyloctan
6-Ethyl-2,5-dimethyloctan
6-Ethyl-2,6-dimethyloctan
6-Ethyl-3,3-dimethyloctan
6-Ethyl-3,4-dimethyloctan

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

3-Ethyl-2,2,3,4-tetramethylhexan
3-Ethyl-2,2,3,5-tetramethylhexan
3-Ethyl-2,2,4,4-tetramethylhexan
3-Ethyl-2,2,4,5-tetramethylhexan
3-Ethyl-2,2,5,5-tetramethylhexan
3-Ethyl-2,3,4,4-tetramethylhexan
3-Ethyl-2,3,4,5-tetramethylhexan
4-Ethyl-2,2,3,3-tetramethylhexan
4-Ethyl-2,2,3,4-tetramethylhexan
4-Ethyl-2,2,3,5-tetramethylhexan
4-Ethyl-2,2,4,5-tetramethylhexan
4-Ethyl-2,3,3,4-tetramethylhexan
4-Ethyl-2,3,3,5-tetramethylhexan
3,3-Diethyl-2,2-dimethylhexan
3,3-Diethyl-2,4-dimethylhexan
3,3-Diethyl-2,5-dimethylhexan
3,3-Diethyl-4,4-dimethylhexan
3,4-Diethyl-2,2-dimethylhexan
3,4-Diethyl-2,3-dimethylhexan
3,4-Diethyl-2,4-dimethylhexan
3,4-Diethyl-2,5-dimethylhexan
3,4-Diethyl-3,4-dimethylhexan
4,4-Diethyl-2,2-dimethylhexan
4,4-Diethyl-2,3-dimethylhexan

3-Ethyl-2,2,3,4,4-pentamethylpentan
3,3-Diethyl-2,2,4-trimethylpentan

Propyl

4-Propylnonan
5-Propylnonan

1-Methylethyl
(= Isopropyl)

4-(1-Methylethyl)nonan
5-(1-Methylethyl)nonan

Methyl
und
Propyl

2-Methyl-4-propyloctan
3-Methyl-4-propyloctan
4-Methyl-4-propyloctan
4-Methyl-5-propyloctan
2-Methyl-5-propyloctan
3-Methyl-5-propyloctan

Methyl
und
1-Methylethyl
(= Isopropyl)

2-Methyl-3-(1-methylethyl)octan
2-Methyl-4-(1-methylethyl)octan
3-Methyl-4-(1-methylethyl)octan
4-Methyl-4-(1-methylethyl)octan
4-Methyl-5-(1-methylethyl)octan
2-Methyl-5-(1-methylethyl)octan
3-Methyl-5-(1-methylethyl)octan

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

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

Ethyl
und
Propyl

3-Ethyl-4-propylheptan
4-Ethyl-4-propylheptan

Ethyl
und
1-Methylethyl
(= Isopropyl)

3-Ethyl-4-(1-methylethyl)heptan
4-Ethyl-4-(1-methylethyl)heptan

Ethyl,
Methyl
und
1-Methylethyl
(= Isopropyl)

3-Ethyl-2-methyl-3-(1-methylethyl)hexan
4-Ethyl-2-methyl-3-(1-methylethyl)hexan

3-Ethyl-2,4-dimethyl-3-(1-methylethyl)pentan
1,1-Dimethylethyl
(= tert-Butyl)
4-(1,1-Dimethylethyl)octan
(4-tert-Butyloctan)
1,1-Dimethylethyl
(= tert-Butyl)
und
Methyl

4-(1,1-Dimethylethyl)-2-methylheptan
4-(1,1-Dimethylethyl)-3-methylheptan
4-(1,1-Dimethylethyl)-4-methylheptan

3-(1,1-Dimethylethyl)-2,2-dimethylhexan

Verwendung[Bearbeiten | Quelltext bearbeiten]

In der Natur kommen Dodecan-Isomere beispielsweise bei der Amerikanischen Dickkopfelritze als Stoffwechselprodukte vor, bei denen n-Dodecan und 2,2,4,6,6-Pentamethylheptan biotransformiert werden, um somit die Bioakkumulation zu verhindern.[3] In der technischen Chemie wird eine Mischung aus Dodecan-Isomeren als Suspensionsmittel verwendet, vor allem für die katalytische Kettenpolymerisation von Olefinen (Polyolefine) mithilfe von Titaniumhalogenid-Materialien.[4]

Einzelnachweise[Bearbeiten | Quelltext bearbeiten]

  1. D. Bonchev: Chemical Graph Theory: Introduction and Fundamentals. CRC Press, 1991, S. 300 (eingeschränkte Vorschau in der Google-Buchsuche).
  2. slywalaate: Constitutional Isomers of Alkanes. In: Scribd. Abgerufen am 26. August 2017 (englisch).
  3. J. Tolls, J. van Dijk: Bioconcentration of n-dodecane and its highly branched isomer 2,2,4,6,6-pentamethylheptane in fathead minnows. In: Chemosphere. Band 47, Nummer 10, Juni 2002, S. 1049–1057, PMID 12137037.
  4. Patent EP0026655: Titanium halide material and production thereof. Veröffentlicht am 8. April 1981, Erfinder: Ian William Parsons, John Andrew Licchelli, Anthony David Caunt.