Icosane

Last updated
Icosane
Eicosane.png
Icosane 3D ball.png
Names
Preferred IUPAC name
Icosane [1]
Other names
Eicosane
Identifiers
3D model (JSmol)
1700722
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.653 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-018-1
MeSH eicosane
PubChem CID
UNII
  • InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3 Yes check.svgY
    Key: CBFCDTFDPHXCNY-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCCCCCCCCCCCCCC
Properties
C20H42
Molar mass 282.556 g·mol−1
AppearanceColorless, waxy crystals
Odor Odorless
Melting point 36 to 38 °C; 97 to 100 °F; 309 to 311 K
Boiling point 343.1 °C; 649.5 °F; 616.2 K
log P 10.897
31 μmol Pa−1 kg−1
Thermochemistry
602.5 J K−1 mol−1 (at 6.0 °C)
Std molar
entropy
(S298)
558.6 J K−1 mol−1
Hazards
NFPA 704 (fire diamond)
0
1
0
Flash point >113 °C (235 °F; 386 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Icosane (alternative spelling eicosane) is an alkane with the chemical formula C20H42. It has 366,319 constitutional isomers.

Contents

Icosane has little use in the petrochemical industry, as its high flash point makes it an inefficient fuel. n-Icosane (the straight-chain structural isomer of icosane) is the shortest compound found in paraffin waxes used to form candles.

Icosane's size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. It is a colorless, non-polar molecule, nearly unreactive except when it burns. It is less dense than and insoluble in water. Its non-polar trait means it can only perform weak intermolecular bonding (hydrophobic/van der Waals forces).

Icosane's phase transition at a moderate temperature makes it a candidate phase change material, or PCM which can be used to store thermal energy and control temperature.

It can be detected in the body odor of persons suffering from Parkinson's disease. [2]

Naming

IUPAC currently recommends icosane, [3] whereas Chemical Abstracts Service and Beilstein use eicosane. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.

<span class="mw-page-title-main">Functional group</span> Set of atoms in a molecule which augment its chemical and/or physical properties

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

<i>Cis</i>–<i>trans</i> isomerism Pairs of molecules with same chemical formula showing different spatial orientations

Cistrans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides. Cistrans isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. Cis-trans notation does not always correspond to EZ isomerism, which is an absolute stereochemical description. In general, cistrans stereoisomers contain double bonds that do not rotate, or they may contain ring structures, where the rotation of bonds is restricted or prevented. Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes. Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used.

<span class="mw-page-title-main">Hexane</span> Chemical compound

Hexane is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14.

Isobutane, also known as i-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colourless, odourless gas. It is the simplest alkane with a tertiary carbon atom. Isobutane is used as a precursor molecule in the petrochemical industry, for example in the synthesis of isooctane.

<span class="mw-page-title-main">Cycloalkane</span> Saturated alicyclic hydrocarbon

In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.

<span class="mw-page-title-main">Carbocation</span> Ion with a positively charged carbon atom

A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium CH+
3
, methanium CH+
5
and vinyl C
2
H+
3
cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountered.

<span class="mw-page-title-main">Open-chain compound</span> Type of organic molecule with a linear structure

In chemistry, an open-chain compound or acyclic compound is a compound with a linear structure, rather than a cyclic one. An open-chain compound having no side chains is called a straight-chain compound. Many of the simple molecules of organic chemistry, such as the alkanes and alkenes, have both linear and ring isomers, that is, both acyclic and cyclic, with the latter often classified as aromatic. For those with 4 or more carbons, the linear forms can have straight-chain or branched-chain isomers. The lowercase prefix n- denotes the straight-chain isomer; for example, n-butane is straight-chain butane, whereas i-butane is isobutane. Cycloalkanes are isomers of alkenes, not of alkanes, because the ring's closure involves a C-C bond. Having no rings, all open-chain compounds are aliphatic.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

Butene, also known as butylene, is an alkene with the formula C4H8. The word butene may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation.

<span class="mw-page-title-main">Chirality (chemistry)</span> Geometric property of some molecules and ions

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

<span class="mw-page-title-main">Conformational isomerism</span> Different molecular structures formed only by rotation about single bonds

In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds. While any two arrangements of atoms in a molecule that differ by rotation about single bonds can be referred to as different conformations, conformations that correspond to local minima on the potential energy surface are specifically called conformational isomers or conformers. Conformations that correspond to local maxima on the energy surface are the transition states between the local-minimum conformational isomers. Rotations about single bonds involve overcoming a rotational energy barrier to interconvert one conformer to another. If the energy barrier is low, there is free rotation and a sample of the compound exists as a rapidly equilibrating mixture of multiple conformers; if the energy barrier is high enough then there is restricted rotation, a molecule may exist for a relatively long time period as a stable rotational isomer or rotamer. When the time scale for interconversion is long enough for isolation of individual rotamers, the isomers are termed atropisomers. The ring-flip of substituted cyclohexanes constitutes another common form of conformational isomerism.

<span class="mw-page-title-main">Neopentane</span> Chemical compound

Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure.

<span class="mw-page-title-main">Isopentane</span> Chemical compound

Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon with five carbon atoms, with formula C
5
H
12
or CH(CH
3
)
2
(C
2
H
5
)
.

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.

<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.

<span class="mw-page-title-main">Chemical compound</span> Substance composed of multiple elements that are chemically bonded

A chemical compound is a chemical substance composed of many identical molecules containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken and/or new bonds formed.

<span class="mw-page-title-main">Pagodane</span> Chemical compound

Pagodane is an organic compound with formula C
20
H
20
whose carbon skeleton was said to resemble a pagoda, hence the name. It is a polycyclic hydrocarbon whose molecule has the D2h point symmetry group. The compound is a highly crystalline solid that melts at 243 °C, is barely soluble in most organic solvents and moderately soluble in benzene and chloroform. It sublimes at low pressure.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 59. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Trivedi, Drupad K.; Sinclair, Eleanor; Xu, Yun; Sarkar, Depanjan; Walton-Doyle, Caitlin; Liscio, Camilla; Banks, Phine; Milne, Joy; Silverdale, Monty; Kunath, Tilo; Goodacre, Royston; Barran, Perdita (2019). "Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum". ACS Central Science. 5 (4): 599–606. doi:10.1021/acscentsci.8b00879. PMC   6487537 . PMID   31041379.
  3. "Table 11 Basic numerical terms (multiplying affixes)". IUPAC . Retrieved 2011-02-16.
  4. "Footnote for Table 11". IUPAC . Retrieved 2011-02-16.