Higher alkane

Higher alkanes are alkanes having nine or more carbon atoms. Nonane is the lightest alkane to have a flash point above 25 °C, and is not classified as dangerously flammable.

The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions.

Synthesis

Uses

Alkanes from nonane to hexadecane (those alkanes with nine to sixteen carbon atoms) are liquids of higher viscosity, which are less suitable for use in gasoline. They form instead the major part of diesel, kerosene, and aviation fuel. Diesel fuels are characterised by their cetane number, cetane being an older name for hexadecane. However the higher melting points of these alkanes can cause problems at low temperatures and in polar regions, where the fuel becomes too thick to flow correctly. Mixtures of the normal alkanes are used as boiling point standards for simulated distillation by gas chromatography.[1]

Alkanes from hexadecane upwards form the most important components of fuel oil and lubricating oil. In latter function they work at the same time as anti-corrosive agents, as their hydrophobic nature means that water cannot reach the metal surface. Many solid alkanes find use as paraffin wax, used for lubrication, electrical insulation, and candles. Paraffin wax should not be confused with beeswax, which consists primarily of esters.

Alkanes with a chain length of approximately 35 or more carbon atoms are found in bitumen (asphalt), used (for example) in road surfacing. However, the higher alkanes have little value and are usually split into lower alkanes by cracking.

Names

Some alkanes have non-IUPAC trivial names:

Properties
See also: List of straight-chain alkanes

The properties listed here refer to the straight-chain alkanes (or: n-alkanes).

Nonane to hexadecane

This group of n-alkanes is generally liquid under standard conditions.[3]

Nonane Decane Undecane Dodecane Tridecane Tetradecane Pentadecane Hexadecane
Formula C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34
CAS number [111-84-2] [124-18-5] [1120-21-4] [112-40-3] [629-50-5] [629-59-4] [629-62-9] [544-76-3]
Molar mass (g/mol) 128.26 142.29 156.31 170.34 184.37 198.39 212.42 226.45
Melting point (°C) −53.5 −29.7 −25.6 −9.6 −5.4 5.9 9.9 18.2
Boiling point (°C) 150.8 174.1 195.9 216.3 235.4 253.5 270.6 286.8
Density (g/ml at 20 °C) 0.71763 0.73005 0.74024 0.74869 0.75622 0.76275 0.76830 0.77344
Viscosity (cP at 20 °C) 0.7139 0.9256 1.185 1.503 1.880 2.335 2.863 3.474
Flash point (°C) 31 46 60 71 79 99 132 135
Autoignition
temperature (°C)		 205 210 205 235 201
Explosive limits 0.9–2.9% 0.8–2.6% 0.45–6.5%

Heptadecane to tetracosane

From this group on, the n-alkanes are generally solid at standard conditions.

Heptadecane Octadecane Nonadecane Icosane Heneicosane Docosane Tricosane Tetracosane
Formula C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50
CAS number [629-78-7] [593-45-3] [629-92-5] [112-95-8] [629-94-7] [629-97-0] [638-67-5] [646-31-1]
Molar mass (g/mol) 240.47 254.50 268.53 282.55 296.58 310.61 324.63 338.66
Melting point (°C) 21 28–30 32–34 36.7 40.5 42 48–50 52
Boiling point (°C) 302 317 330 342.7 356.5 224 at 2 kPa 380 391.3
Density (g/ml) 0.777 0.777 0.786 0.7886 0.792 0.778 0.797 0.797
Flash point (°C) 148 166 168 176

Pentacosane to triacontane
Pentacosane Hexacosane Heptacosane Octacosane Nonacosane Triacontane
Formula C25H52 C26H54 C27H56 C28H58 C29H60 C30H62
CAS number [629-99-2] [630-01-3] [593-49-7] [630-02-4] [630-03-5] [638-68-6]
Molar mass (g/mol) 352.69 366.71 380.74 394.77 408.80 422.82
Melting point (°C) 54 56.4 59.5 64.5 63.7 65.8
Boiling point (°C) 401 412.2 422 431.6 440.8 449.7
Density (g/ml) 0.801 0.778 0.780 0.807 0.808 0.810

Hentriacontane to hexatriacontane
Hentriacontane Dotriacontane Tritriacontane Tetratriacontane Pentatriacontane Hexatriacontane
Formula C31H64 C32H66 C33H68 C34H70 C35H72 C36H74
CAS number [630-04-6] [544-85-4] [630-05-7] [14167-59-0] [630-07-9] [630-06-8]
Molar mass (g/mol) 436.85 450.88 464.90 478.93 492.96 506.98
Melting point (°C) 67.9 69 70–72 72.6 75 74–76
Boiling point (°C) 458 467 474 285.4 at 0.4 kPa 490 265 at 130 Pa
Density (g/ml) 0.781 at 68 °C[4] 0.812 0.811 0.812 0.813 0.814

Heptatriacontane to dotetracontane
Heptatriacontane Octatriacontane Nonatriacontane Tetracontane Hentetracontane Dotetracontane
Formula C37H76 C38H78 C39H80 C40H82 C41H84 C42H86
CAS number [7194-84-5] [7194-85-6] [7194-86-7] [4181-95-7] [7194-87-8] [7098-20-6]
Molar mass (g/mol) 520.99 535.03 549.05 563.08 577.11 591.13
Melting point (°C) 77 79 78 84 83 86
Boiling point (°C) 504.14 510.93 517.51 523.88 530.75 536.07
Density (g/ml) 0.815 0.816 0.817 0.817 0.818 0.819

Tritetracontane to octatetracontane
Triatetracontane Tetratetracontane Pentatetracontane Hexatetracontane Heptatetracontane Octatetracontane
Formula C43H88 C44H90 C45H92 C46H94 C47H96 C48H98
CAS Number [7098-21-7] [7098-22-8] [7098-23-9] [7098-24-0] [7098-25-1] [7098-26-2]
Molar mass (g/mol) 605.15 619.18 633.21 647.23 661.26 675.29
Boiling point (°C) 541.91 547.57 553.1 558.42 563.6 568.68
Density (g/ml) 0.82 0.82 0.821 0.822 0.822 0.823

Nonatetracontane to tetrapentacontane
Nonatetracontane Pentacontane Henpentacontane Dopentacontane Tripentacontane Tetrapentacontane
Formula C49H100 C50H102 C51H104 C52H106 C53H108 C54H110
CAS number [7098-27-3] [6596-40-3] [7667-76-7] [7719-79-1] [7719-80-4] [5856-66-6]
Molar mass (g/mol) 689.32 703.34 717.37 731.39 745.42 759.45
Boiling point (°C) 573.6 578.4 583 587.6 592 596.38
Density (g/ml) 0.823 0.824 0.824 0.825 0.825 0.826

Pentapentacontane to hexacontane
Pentapentacontane Hexapentacontane Heptapentacontane Octapentacontane Nonapentacontane Hexacontane
Formula C55H112 C56H114 C57H116 C58H118 C59H120 C60H122
CAS number [5846-40-2] [7719-82-6] [5856-67-7] [7667-78-9] [7667-79-0] [7667-80-3]
Molar mass (g/mol) 773.48 787.50 801.53 815.58 829.59 843.6
Boiling point (°C) 600.6 604.7  ? 612.6  ? 620.2
Density (g/ml) 0.826 0.826  ? 0.827  ? 0.827

See also

References
  1. ASTM D5399-09, Standard Test Method for Boiling Point Distribution of Hydrocarbon Solvents by Gas Chromatography
  2. Donald Mackay, Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, ISBN 1420044397, p. 206
  3. Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer Hartmut Höke "Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227
  4. Weast, Robert C., ed. (1982). CRC Handbook of Chemistry and Physics (63rd ed.). Boca Raton, Fl: CRC Press. p. C-561.
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