294-62-2 Usage
Description
Cyclododecane (CDD) is an explosive cyclic alkane that is moderately inert, consisting solely of hydrogen and carbon compounds, and is non-polar. It is a colorless, translucent compound with a wax-like consistency and good film-forming properties. At room temperature, cyclododecane is stable and commonly sold in the form of irregularly formed crystals. It has a boiling point of 243°C and a melting point of 58-61°C. One of its most attractive properties is that it sublimes, eliminating the need for additional chemical procedures to remove it.
Uses
Used in Conservation Industry:
Cyclododecane is used as a temporary fixative, consolidant, barrier layer, and masking material in various fields of specialization. As a consolidant, it protects fragile ceramics during movement, allowing packaging and handling without damage. It also serves as a temporary adhesive that can be removed without causing any damage.
Used in Aqueous Treatment:
Cyclododecane is employed as a fixative for moisture-sensitive media on paper during the process of aqueous treatment. Its non-polar quality allows it to protect materials that are solvent-sensitive during local solvent treatment.
Used in Transportation and Cleaning:
At room temperature, cyclododecane forms a typically rigid solid, making it useful for securing friable substrates or flaking paint during transportation or cleaning.
Used in Mold Making:
Cyclododecane is used to isolate the surface of an object when making a mold.
Used in Organic Synthesis:
Cyclododecane is used as an intermediate for the production of chemicals used to make polyamides, polyesters, synthetic lubricating oils, and nylon 12. It is also used as a high-purity solvent.
Used in Pesticide Emulsification:
An emulsion of cyclododecane can be used to emulsify pesticides.
Used as a Mothproofing Agent:
Cyclododecane is also utilized as a mothproofing agent.
Application Methods
Cyclododecane can be applied as a solvent solution or a melt. There should be a consideration of the substrate when selecting an application methods. Cyclododecane is generally reapplied between treatments for works of art paper.
Cyclododecane melts at about 60oC and can applied with a wax-melting stylus, heated spatula, melting the compound, and spraying machine. A rheostat may be used to control the temperatures of the tools used to apply cyclododecane.
Brush application should not be used unless a solvent is added at lower melting point. Cyclododecane will solidify and form a film after cooling. On the other hand, an immediate transition in temperature will form a dense, homogeneous film.
Cyclododecane can be dissolved in aromatic and non-polar solvents and applied by syringe, brush, or aerosol-spray. However, it is almost impossible to produce uniform films and numerous applications are needed to build up the film.
Treatment Considerations
It is important to evaluate the aims of the treatment and the stability of object. Also, sensitivity of object to hydrocarbon or to heat should be considered. Although CDD is comparatively transparent, areas that are normally covered with the compound have reduced clarity.
Health Effects
Contact of cyclododecane with the skin may cause rash or irritation while it can cause irritation and discomfort to the eye or a blurring vision. To avoid inhalation exposure through vapors, one should wear a respirator. Eye protection such as goggles and safety glasses is recommended to avoid contact through spraying or splashing of the material. In addition, gloves should always be used when handling cyclododecane solvents. As a volatile material, cyclododecane should be stored away from flames and sparks, which might ignite it. Moreover, it should not be mixed with strong oxidants.
Synthesis Reference(s)
Tetrahedron Letters, 36, p. 3897, 1995 DOI: 10.1016/0040-4039(95)00593-2
Check Digit Verification of cas no
The CAS Registry Mumber 294-62-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 294-62:
(5*2)+(4*9)+(3*4)+(2*6)+(1*2)=72
72 % 10 = 2
So 294-62-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2
294-62-2Relevant articles and documents
Saltiel,J.,Ng Lim,L.-S.
, p. 5404 - 5405 (1969)
Diastereomeric cyclic tris-allenes
Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.
, p. 2497 - 2499 (2013)
Both diastereomers of the tris-allene, cyclododeca-1,2,5,6,9,10-hexaene have been obtained using a triple cyclopropylidene-allene rearrangement. On the NMR timescale, one has D3 symmetry, and is the smallest hydrocarbon synthesised to have this symmetry, and the second has C2 symmetry.
Discrimination of Rotational Isomeric States in Cycloalkanes by Solid-State CP-MAS 13C NMR Spectroscopy
Moeller, Martin,Gronski, Wolfram,Cantow, Hans Joachim,Hoecker, Hartwig
, p. 5093 - 5099 (1984)
The solid-state behavior of three cycloalkanes, cyclododecane, cyclotetraeicosane, and cyclohexatriacontane, was investigated by means of temperature dependent magic angle cross-polarization 13C NMR experiments.For the two smaller ring molecules a state of high internal mobility like the "rotator phase" in n-alkanes was detected.It could be correlated with a phase transition in the solid state visible by means of DSC.In the case of (CH2)12 this is 151 K below the melting point, and in the case of (CH2)24 it is 25 K below the melting transition.The CP-MAS 13C NMR spectra show a transition from the fast exchange to the slow exchange regime of magnetically nonequivalent states.By comparison with X-ray diffraction data the well-resolved resonance signals for the low-temperature phases were assigned to molecular segments distinguished by the rotational isomeric states of the carbon-carbon bonds.Chemical shift differences due to conformational isomerism were as large as 12 ppm; thus, they exceed "packing effects" by far.
Sustainable System for Hydrogenation Exploiting Energy Derived from Solar Light
Ishida, Naoki,Kamae, Yoshiki,Ishizu, Keigo,Kamino, Yuka,Naruse, Hiroshi,Murakami, Masahiro
supporting information, p. 2217 - 2220 (2021/02/16)
Herein described is a sustainable system for hydrogenation that uses solar light as the ultimate source of energy. The system consists of two steps. Solar energy is captured and chemically stored in the first step; exposure of a solution of azaxanthone in ethanol to solar light causes an energy storing dimerization of the ketone to produce a sterically strained 1,2-diol. In the second step, the chemical energy stored in the vicinal diol is released and used for hydrogenation; the diol offers hydrogen onto alkenes and splits back to azaxanthone, which is easily recovered and reused repeatedly for capturing solar energy.
Hydrogenation of 1,5,9-Cyclododecatriene in a Three-Phase System in the Presence of Nickel Nanoparticles Supported on NаX Zeolite
Nebykov,Popov, Yu. V.,Mokhov,Shcherbakova,Zotov, Yu. L.
, p. 110 - 115 (2021/03/18)
The hydrogenation of 1,5,9-cyclododecatriene in the presence of nanostructured Ni catalysts, supported with NaX zeolite, in a flow-through reactor at atmospheric hydrogen pressure was investigated. Nickel nanoparticles on the support surface were prepared by chemical reduction of the precursor (NiCl2) with NaBH4 and NH2NH2. The effect exerted on the yield of hydrogenation products by the nominal residence time of the gas phase in the reaction zone and by the process temperature was considered, and the catalyst operation life was analyzed. The catalysts showed high activity and allowed preparation of cyclododecane in ~100% yield at a process temperature of up to 160°С.