Cyclododecane

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Cyclododecane
Structural formula of cyclododecane.svg
Cyclododecane 3D ball.png
Names
Preferred IUPAC name
Cyclododecane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.486 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 Yes check.svgY
    Key: DDTBPAQBQHZRDW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2
    Key: DDTBPAQBQHZRDW-UHFFFAOYAN
  • C1CCCCCCCCCCC1
Properties
C12H24
Molar mass 168.324 g·mol−1
AppearanceWhite waxy solid [1]
Density 0.855 g/cm3 [2]
Melting point 60.4 °C (140.7 °F; 333.5 K) [3]
Boiling point 244.0 °C (471.2 °F; 517.1 K) [2]
Structure [4]
Monoclinic
C2/m
D4 [5]
a = 13.27 Å, b = 8.28 Å, c = 5.44 Å
α = 90°, β = 99.5°, γ = 90°
589.7 Å3
2
Hazards
GHS labelling:
H413 [3]
P273, P501 [3]
Flash point 87.6 °C (189.7 °F; 360.8 K)
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 ?)

Cyclododecane is an organic compound with the chemical formula (CH2)12. [3] It is a waxy white solid at room temperature, [1] :17 and is soluble in nonpolar organic solvents.

It is an intermediate of Nylon 12, polyesters, and synthetic lubricating oils. [3] :8.1 It is also used as a temporary binder to stabilise fragile objects or to seal water-sensitive parts; it slowly sublimates over days or weeks without leaving any residue. [1] :17

Synthesis

Cyclododecane is produced industrially through catalytic trimerisation of butadiene to cyclododecatriene, followed by hydrogenation. [6]

Uses

It is a precursor to laurolactam, a precursor to the polymer Nylon 12. [7]

Formation of laurolactam Laurolactam formation 2.png
Formation of laurolactam

Cyclododecane is also an intermediate in production of flame retardants, detergents, and other chemicals.

Cyclododecane is also used as a volatile binding medium, a temporary binder for sealing and conservation of friable and structurally weak materials, e.g. during excavation and transport of archaeological objects and in art restoration, e.g. to protect water-sensitive parts during cleaning. [1] Due to its relatively slow evaporation in comparison with other volatile binding mediums the layer can last for several weeks. Very pure material has to be used so it does not leave any residue. Cyclododecane can be applied in molten state or dissolved in a nonpolar organic solvent. Other volatile binding mediums in use are camphene, tricyclene and with some limits menthol.

Environmental considerations

Cyclododecane is persistent in the environment, as it does not biodegrade easily. Cyclododecane is lipophilic, usually present in the environment as adsorbed on the surface of soil particles. It has the potential to bioaccumulate. Cyclododecane may cause long lasting harmful effects to aquatic life. [8]

Conformation

Cyclododecane has low ring strain. It adopts a [3333] conformation with square (D4) symmetry. [5] [9] [10] :Fig. 70 While highly stable, this conformation is not derivable from a diamond lattice, [10] unlike the lowest-energy conformations of cyclohexane, cyclotetradecane, and cyclohexadecane. [9] Monosubstituted cyclododecanes also typically adopt the [3333] conformation, [11] :5916 though more highly substituted cyclododecanes may adopt alternative conformations, such as [4332]. [12] :10583

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">Piperidine</span> Chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

<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">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.

<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, in which case pentanes refers to a mixture of them; 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.

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

Dibenzofuran is a heterocyclic organic compound with the chemical structure shown at right. It is an aromatic compound that has two benzene rings fused to a central furan ring. All the numbered carbon atoms have a hydrogen atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from coal tar, where it exists as a 1% component.

Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its freezing point is −94 °C and its boiling point is 49 °C. Cyclopentane is in the class of cycloalkanes, being alkanes that have one or more carbon rings. It is formed by cracking cyclohexane in the presence of alumina at a high temperature and pressure.

<span class="mw-page-title-main">Cyclohexane conformation</span> Structures of cyclohexane

Cyclohexane conformations are any of several three-dimensional shapes adopted by cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide range of compounds.

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

In chemistry, rotamers are chemical species that differ from one another primarily due to rotations about one or more single bonds. Various arrangements of atoms in a molecule that differ by rotation about single bonds can also be referred to as different conformations. Conformers/rotamers differ little in their energies, so they are almost never separable in a practical sense. Rotations about single bonds are subject to small energy barriers. When the time scale for interconversion is long enough for isolation of individual rotamers, the species are termed atropisomers. The ring-flip of substituted cyclohexanes constitutes a common form of conformers.

In chemistry, a molecule experiences strain when its chemical structure undergoes some stress which raises its internal energy in comparison to a strain-free reference compound. The internal energy of a molecule consists of all the energy stored within it. A strained molecule has an additional amount of internal energy which an unstrained molecule does not. This extra internal energy, or strain energy, can be likened to a compressed spring. Much like a compressed spring must be held in place to prevent release of its potential energy, a molecule can be held in an energetically unfavorable conformation by the bonds within that molecule. Without the bonds holding the conformation in place, the strain energy would be released.

<span class="mw-page-title-main">Ring strain</span> Instability in molecules with bonds at unnatural angles

In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated.

Noncovalent solid-phase organic synthesis (NC-SPOS) is a form of solid-phase synthesis whereby the organic substrate is bonded to the solid phase not by a covalent bond but by other chemical interactions.

<span class="mw-page-title-main">Salt bridge (protein and supramolecular)</span> Combination of hydrogen and ionic bonding in chemistry

In chemistry, a salt bridge is a combination of two non-covalent interactions: hydrogen bonding and ionic bonding. Ion pairing is one of the most important noncovalent forces in chemistry, in biological systems, in different materials and in many applications such as ion pair chromatography. It is a most commonly observed contribution to the stability to the entropically unfavorable folded conformation of proteins. Although non-covalent interactions are known to be relatively weak interactions, small stabilizing interactions can add up to make an important contribution to the overall stability of a conformer. Not only are salt bridges found in proteins, but they can also be found in supramolecular chemistry. The thermodynamics of each are explored through experimental procedures to access the free energy contribution of the salt bridge to the overall free energy of the state.

<span class="mw-page-title-main">Jack D. Dunitz</span> British chemist (1923–2021)

Jack David Dunitz FRS was a British chemist and widely known chemical crystallographer. He was Professor of Chemical Crystallography at the ETH Zurich from 1957 until his official retirement in 1990. He held Visiting Professorships in the United States, Israel, Japan, Canada, Spain and the United Kingdom.

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

Cyclododecatrienes are cyclic trienes with the formula C12H18. Four isomers are known for 1,5,9-cyclododecatriene. The trans,trans,cis-isomer is a precursor in the production of nylon-12.

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

Cyclooctane is a cycloalkane with the molecular formula (CH2)8. It is a simple colourless hydrocarbon, but it is often a reference compound for saturated eight-membered ring compounds in general.

Cycloheptane, synonym suberane, is a cycloalkane with the molecular formula C7H14. It is a poorly water soluble organic liquid (melting point –12 deg C, solubility in water <30 mg /liter at 25 deg C), and is used as a nonpolar solvent for the chemical industry and as an intermediate in the manufacture of chemicals and pharmaceutical drugs. It can be prepared by Clemmensen reduction from cycloheptanone. Cycloheptane vapour is irritating to the eyes and may cause respiratory depression if inhaled in large quantity.

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

Laurolactam is an organic compound from the group of macrocyclic lactams. Laurolactam is mainly used as a monomer in engineering plastics, such as nylon-12 and copolyamides.

References

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  2. 1 2 ECHA REACH
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  4. Dunitz, JD; Shearer, HMM (1960). "Die Strukturen der mittleren Ringverbindungen III. Die Struktur des Cyclododecans". Helvetica Chimica Acta. 43 (1): 18–35. doi:10.1002/hlca.19600430104.
  5. 1 2 Atavin, EG; Mastryukov, VS; Allinger, NL; Almenningen, A; Seip, R (September 1989). "Molecular structure of cyclododecane, C12H24, as determined by electron diffraction and molecular mechanics". Journal of Molecular Structure. 212: 87–95. doi:10.1016/0022-2860(89)85069-0.
  6. Arpe, Hans-Jürgen (12 March 2007). Industrielle Organische Chemie (in German). John Wiley & Sons. p. 291. ISBN   978-3-527-31540-6.
  7. Schiffer, T.; Oenbrink, G. (2009). "Cyclododecanol, Cyclododecanone, and Laurolactam". Ullman's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a08_201.pub2. ISBN   978-3527306732.
  8. "Cyclododecane". European Chemicals Agency.
  9. 1 2 Wilen, Samuel H.; Eliel, Ernest Ludwig; Mander, Lewis N. (1994). Stereochemistry of organic compounds. New York: Wiley. p. 769. ISBN   9780471016700.
  10. 1 2 Dragojlovic, Veljko (September 2015). "Conformational analysis of cycloalkanes". ChemTexts. 1 (3). doi:10.1007/s40828-015-0014-0.
  11. Khorasani, Sanaz; Fernandes, Manuel A.; Perry, Christopher B. (5 December 2012). "Do 12-Membered Cycloalkane Rings Only Exist As One Conformation in the Solid-State? A Detailed Solid-State Analysis Involving Polymorphs of N,N'-Biscyclododecyl Pyromellitic Diimide". Crystal Growth & Design. 12 (12): 5908–5916. doi:10.1021/cg300765b.
  12. Skibinski, Maciej; Wang, Yi; Slawin, Alexandra M. Z.; Lebl, Tomas; Kirsch, Peer; O'Hagan, David (4 November 2011). "Alicyclic Ring Structure: Conformational Influence of the CF2 Group in Cyclododecanes". Angewandte Chemie International Edition. 50 (45): 10581–10584. doi:10.1002/anie.201105060.