Циклододецен

Description

Cyclododecene is an unsaturated macrocyclic hydrocarbon, a twelve-membered carbocyclic ring with one double bond (1-cyclododecene). Refers to intermediate products of petrochemical synthesis: key raw materials for the production of cyclododecanone and cyclododecanol, which are further converted into laurolactam (nylon-12 monomer) and dodecanedioic acid.

Basic Attributes

• CAS No: 1501-82-2
• Chemical formula: C12H22
• Molecular weight: 166.3
• Exact weight: 166.30
• EU number: 216-117-7
• HS code: 29021990
• XLogP3: 4.4572

Physico-chemical characteristics

• Appearance: liquid
• Density: 0.8776 g/cm3 at 20 °C
• Melting point: 99–99.5 °C (data for heptane solvent)
• Boiling point: 99 °C at 5 Torr pressure
• Flash point: 201°F (approx. 94°C)
• Refractive index: n20/D 1.485
• Solubility in water: insoluble; soluble in alcohol
• Steam pressure: 9.88×10⁻⁸ mm Hg. Art. at 25 °C

Scope of application

The main purpose is an intermediate petrochemical product: raw materials for the production of cyclododecanone and cyclododecanol, from which laurolactam (nylon-12 monomer) and dodecanedioic acid (via ozonolysis of the double bond) are further synthesized. Cyclododecanone and its derivatives are also used in perfumery as precursors to musky aromatic substances. Cyclododecene itself is used as a starting material in the reactions of epoxidation, hydration and oxidative cleavage at the double bond.

Safety Information

• WGK Germany: 1
• Hazard class code: R38 - skin irritant
• Safety instructions: 23-24/25
• Tags: Xi - irritating factor
• Stability: stable, flammable, incompatible with strong oxidizing agents

Storage and transportation conditions

Store in an airtight container in a cool, dry place, away from strong oxidizing agents. The substance is flammable - avoid contact with ignition sources. When working, use gloves and safety glasses to avoid skin irritation.

Place in the production chain

The industrial synthesis of cyclododecene is based on the cyclotrimerization of butadiene to cyclododecatriene followed by selective hydrogenation of two of the three double bonds - this route remains the main source of twelve-membered carbocycles in petrochemistry.

Further transformations

The oxidation of cyclododecene with atmospheric oxygen in the presence of catalysts produces a mixture of cyclododecanone and cyclododecanol (the so-called CA oil), which is separated and used separately: the ketone in the production of laurolactam, the alcohol in the production of dodecanedioic acid. The XLogP3 value of 4.4572 indicates a pronounced lipophilicity of the macrocycle, typical of twelve-membered carbocyclic structures.

Practical recommendation

When purchasing for petrochemical production, it is worth clarifying the content of accompanying isomers (cis/trans, position of the double bond) - the yield of the target cyclododecanone at the stage of catalytic oxidation depends on their proportion.