Dodecane

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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 Substituenten:[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

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

  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.