Cyclododecane
[CAS 294-62-2]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Cyclic hydrocarbon
• Name: Cyclododecane
• Molecular Formula: C₁₂H₂₄
• Molecular Weight: 168.32
• CAS Registry Number: 294-62-2
• EC Number: 206-033-9
• SMILES: C1CCCCCCCCCCC1

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*, 0.79 g/mL (Expl.)
• Melting point: 59 - 61 °C (Expl.)
• Boiling point: 247.0 °C 760 mmHg (Calc.)^*, 239 °C (Expl.)
• Flash point: 87.6±11.7 °C (Calc.)^*
• Index of refraction: 1.433 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H413
• Safety Statements: P264-P270-P273-P301+P312+P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Cyclododecane is a saturated cyclic hydrocarbon belonging to the family of cycloalkanes. It consists of a twelve-membered carbon ring with the molecular formula C₁₂H₂₄. The compound has attracted scientific and industrial interest because of its unique physical properties, particularly its ability to sublime under ambient conditions. Unlike many other temporary protective materials, cyclododecane gradually disappears without leaving measurable residues, making it valuable in applications where complete removal after use is required.

The compound was synthesized and investigated as part of the broader study of medium- and large-ring cycloalkanes during the development of modern organic chemistry. Research on cyclododecane contributed to a better understanding of conformational analysis, since twelve-membered rings possess considerable flexibility and can adopt multiple stable conformations. Studies of cyclododecane helped establish principles governing ring strain, molecular motion, and conformational equilibria in macrocyclic hydrocarbons. These investigations provided important information for the study of larger cyclic compounds and macrocyclic chemistry.

Industrial production of cyclododecane became established through catalytic processes that convert suitable hydrocarbon feedstocks into cyclic products. The availability of efficient manufacturing methods enabled the compound to be produced on a commercial scale, supporting its use as both a chemical intermediate and a specialty material. In industrial chemistry, cyclododecane has served as a starting material for the manufacture of cyclododecanone and cyclododecanol, which are important intermediates in the production of laurolactam. Laurolactam is subsequently polymerized to produce polyamide 12, commonly known as nylon 12, an engineering plastic valued for its mechanical strength, chemical resistance, and durability. Through this sequence of transformations, cyclododecane occupies an important position in the manufacture of high-performance polymer materials.

Beyond its role in chemical manufacturing, cyclododecane has become widely recognized for its applications in cultural heritage conservation. Conservators use the compound as a temporary consolidant and protective coating for fragile archaeological objects, works of art, fossils, and other delicate materials. Molten cyclododecane can be applied to the surface of an object, where it solidifies and provides temporary mechanical support during handling, transportation, cleaning, or treatment. After the conservation work has been completed, the material gradually sublimes under normal environmental conditions, eliminating the need for solvent removal and reducing the risk of introducing contaminants. This property has made cyclododecane an important tool in museum conservation and archaeological practice.

The compound has also been employed during excavation and recovery of fragile specimens. Archaeologists and paleontologists have used cyclododecane to stabilize delicate materials before removal from excavation sites. Temporary reinforcement provided by the solid hydrocarbon allows specimens to be transported more safely to laboratories or museums for further examination and conservation. Because the material eventually disappears through sublimation, it minimizes interference with later analytical or restoration procedures.

In addition to conservation, cyclododecane has been used as a temporary masking material in selected manufacturing and surface-treatment processes. Its ability to form a solid protective layer and subsequently sublime without leaving significant residue has been utilized where reversible protection of surfaces is desirable. These specialized applications take advantage of the compound's physical behavior rather than its chemical reactivity.

Cyclododecane has also served as a model compound in academic research. Because it is a relatively simple macrocyclic hydrocarbon, it has been studied extensively in investigations of conformational dynamics, molecular modeling, crystallography, and physical chemistry. Experimental and theoretical studies of cyclododecane have contributed to the understanding of flexible ring systems and have provided benchmark data for computational methods used to predict molecular structure and conformational behavior.

Today, cyclododecane remains important in both industrial chemistry and cultural heritage conservation. Its role as a precursor in the manufacture of nylon 12 intermediates and its unique ability to provide temporary, residue-free protection through sublimation have ensured its continued value across multiple scientific and technical disciplines.

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References

2026. Permeable reactive barriers for groundwater remediation: a comprehensive review. International Journal of Environmental Science and Technology.
DOI: 10.1007/s13762-025-06940-1

2025. Towards sustainable long-chain dicarboxylic acid production: challenges and opportunities. World Journal of Microbiology and Biotechnology.
DOI: 10.1007/s11274-025-04744-6

2025. Dosimetry and preclinical evaluation of long-term radiotoxicity following treatment with 212Pb alpha-radioimmunotherapy targeting CD20. EJNMMI Research.
DOI: 10.1186/s13550-025-01349-w