Cyclododecane

Last updated

Contents

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 0.79 g/cm3
Melting point 60.4 °C (140.7 °F; 333.5 K) [2]
Boiling point 247.0 °C (476.6 °F; 520.1 K) [2]
Hazards
GHS labelling:
H413 [2]
P273, P501 [2]
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. [2] 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. [2] :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. [3]

Uses

It is a precursor to laurolactam, a precursor to the polymer Nylon 12. [4]

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. [5]

Related Research Articles

<span class="mw-page-title-main">Paint</span> Pigment applied over a surface that dries as a solid film

Paint is a liquid pigment that, after applied to a solid material and allowed to dry, adds a film-like layer, in most cases to create an image, known as a painting. Paint can be made in many colors and types. Most paints are either oil-based or water-based, and each has distinct characteristics.

<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">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<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.

<span class="mw-page-title-main">Pyrolysis</span> Thermal decomposition of materials at elevated temperatures in an inert atmosphere

The pyrolysis process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere.

<span class="mw-page-title-main">Flux (metallurgy)</span> Chemical used in metallurgy for cleaning or purifying molten metal

In metallurgy, a flux is a chemical cleaning agent, flowing agent, or purifying agent. Fluxes may have more than one function at a time. They are used in both extractive metallurgy and metal joining.

<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.

Volatile organic compounds (VOCs) are organic compounds that have a high vapor pressure at room temperature. High vapor pressure correlates with a low boiling point, which relates to the number of the sample's molecules in the surrounding air, a trait known as volatility.

<span class="mw-page-title-main">Destructive distillation</span> Chemical process

Destructive distillation is a chemical process in which decomposition of unprocessed material is achieved by heating it to a high temperature; the term generally applies to processing of organic material in the absence of air or in the presence of limited amounts of oxygen or other reagents, catalysts, or solvents, such as steam or phenols. It is an application of pyrolysis. The process breaks up or 'cracks' large molecules. Coke, coal gas, gaseous carbon, coal tar, ammonia liquor, and coal oil are examples of commercial products historically produced by the destructive distillation of coal.

A binder or binding agent is any material or substance that holds or draws other materials together to form a cohesive whole mechanically, chemically, by adhesion or cohesion.

<span class="mw-page-title-main">Pressure-sensitive adhesive</span> Type of non reactive adhesive

Pressure-sensitive adhesive is a type of nonreactive adhesive which forms a bond when pressure is applied to bond the adhesive with a surface. No solvent, water, or heat is needed to activate the adhesive. It is used in pressure-sensitive tapes, labels, glue dots, stickers, sticky note pads, automobile trim, and a wide variety of other products.

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

Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

Air-free techniques refer to a range of manipulations in the chemistry laboratory for the handling of compounds that are air-sensitive. These techniques prevent the compounds from reacting with components of air, usually water and oxygen; less commonly carbon dioxide and nitrogen. A common theme among these techniques is the use of a fine (100–10−3 Torr) or high (10−3–10−6 Torr) vacuum to remove air, and the use of an inert gas: preferably argon, but often nitrogen.

<span class="mw-page-title-main">2-Vinylpyridine</span> Chemical compound

2-Vinylpyridine is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group in the 2-position, next to the nitrogen. It is a colorless liquid, although samples are often brown. It is used industrially as a precursor to specialty polymers and as an intermediate in the chemical, pharmaceutical, dye, and photo industries. Vinylpyridine is sensitive to polymerization. It may be stabilized with a free radical inhibitor such as tert-butylcatechol. Owing to its tendency to polymerize, samples are typically refrigerated.

<span class="mw-page-title-main">Conservation and restoration of feathers</span> Process of protecting feathers

The conservation and restoration of feathers is the practice of maintaining and preserving feathers or featherwork objects, and requires knowledge of feather anatomy, properties, specialized care procedures, and environmental influences. This practice may be approached through preventive and/or interventive techniques.

The conservation and restoration of lacquerware prevents and mitigates deterioration or damage to objects made with lacquer. The two main types of lacquer are Asian, made with sap from the Urushi tree, and European, made with a variety of shellac and natural resins. Lacquer can be damaged by age, light, water, temperature, or damaged substrate.

<span class="mw-page-title-main">Conservation and restoration of paintings</span> Preservation of heritage collections

The conservation and restoration of paintings is carried out by professional painting conservators. Paintings cover a wide range of various mediums, materials, and their supports. Painting types include fine art to decorative and functional objects spanning from acrylics, frescoes, and oil paint on various surfaces, egg tempera on panels and canvas, lacquer painting, water color and more. Knowing the materials of any given painting and its support allows for the proper restoration and conservation practices. All components of a painting will react to its environment differently, and impact the artwork as a whole. These material components along with collections care will determine the longevity of a painting. The first steps to conservation and restoration is preventive conservation followed by active restoration with the artist's intent in mind.

<span class="mw-page-title-main">Agents of deterioration</span> Major causes of damage to cultural heritage

The 'ten agents of deterioration' are a conceptual framework developed by the Canadian Conservation Institute (CCI) used to categorise the major causes of change, loss or damage to cultural heritage objects. Also referred to as the 'agents of change', the framework was first developed in the late 1980s and early 1990s. The defined agents reflect and systematise the main chemical and physical deterioration pathways to which most physical material is subject. They are a major influence on the applied practice of conservation, restoration, and collection management, finding particular use in risk management for cultural heritage collections.

Cultural heritage collections contain many materials known to be hazardous to the environment and to human health. Some hazardous substances may be an integral part of the object, applied as a treatment after the object was made or the result of material degradation. The toxicity of such objects in heritage collections can also determine their historic and scientific value. Consequently, management of these materials within collecting organisations can be complex in terms of health and safety.

References

  1. 1 2 3 4 Rowe, Sophie; Rozeik, Christina (2008). "The uses of cyclododecane in conservation". Studies in Conservation. 53: 17–31. doi:10.1179/sic.2008.53.Supplement-2.17. S2CID   192201300.
  2. 1 2 3 4 5 6 "Cyclododecane". PubChem . National Center for Biotechnology Information . Retrieved 1 September 2021.
  3. Arpe, Hans-Jürgen. Industrielle Organische Chemie (in German). p. 291. ISBN   978-3-527-31540-6.
  4. 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.
  5. "Cyclododecane". European Chemicals Agency.