C12, C8 Monomers

Daicel-Evonik offers the world's widest range of technically available cyclic C8 and C12 building blocks.

All our products are based exclusively on the dimerization and trimerization of butadiene, from which the product families of C8 and C12 rings are developed.

These are widely used in the areas of

• coatings and plastics
• fragrances
• flavors
• flame retardation
• light protection
• solvents, and as
• chemical intermediates

The latest addition to our family of C12 products is cyclododecene, produced by a new, patented process.

We are continually improving our existing production processes to consolidate our leading position in the large-scale production of ring-shaped C8 and C12 synthesis components.

Cyclododecatriene （CDT） -C12 Rings

The triple-unsaturated cyclic hydrocarbon cyclododecatriene （CDT） is a colorless liquid at room temperature, with a characteristic terpene-like odor. It has a boiling point of 263.5°C.

CDT is formed by catalytic trimerization of butadiene.

Of the possible isomers of CDT, only the cis, trans, trans-1,5,9 isomer is industrially important. The triple-unsaturated character of the C12 ring permits a wide range of chemical reactions, making CDT one of the most important starting materials for cyclic and linear compounds with 12 carbon atoms. Moreover, these reactions can be selectively controlled so as to allow reaction of only one or two of the double bonds.

• the product obtained on complete hydrogenation of CDT is cyclododecane, a chemical intermediate that is converted in a number of synthetic steps to laurolactam, the monomer of polyamide 12 （VESTAMID®L）.
• if this complete hydrogenation is followed by oxidative ring-opening, the product is 1,12-dodecanedioic acid, an important monomer in the production of plastics and coatings.
• selective hydrogenation leads to the monofunctional cyclododecene.
• CDT is an important raw material in the manufacture of brominated flame retardants, which are used mainly in plastics, for example, polystyrene.
• it is also used in the production of fragrances and odorants for the perfume industry.

Cyclododecanol （CDOL） -C12 Rings

The secondary alcohol cyclododecanol （CDOL） is a colorless solid with a pronounced camphor-like odor. It is readily soluble in organic solvents but has only limited solubility （0.004% by weight） in water.

CDOL is produced by boric-acid catalyzed oxidation of cyclododecane.

• CDOL is an intermediate in the synthesis of laurolactam, the monomer of polyamide 12 （VESTAMID® L）. Laurolactam itself is synthesized from cyclododecane, with cyclododecanol, cyclododecanone and cyclododecanone oxime as intermediates in successive steps.
• oxidative ring cleavage of CDOL gives 1,12-dodecanedioic acid, also an important component for polymer synthesis.
• the fragrance industry uses CDOL to a large extent for synthesis of macrocyclic perfume ingredients with a musky note.
• fragrances of a woody character are also produced using CDOL.

Cyclododecanone （CDON） -C12 Rings

The cyclic aliphatic ketone cyclododecanone （CDON） is a colorless solid with a melting point of 61°C.

CDON is formed by dehydrogenation of cyclododecanol.

• CDON is an intermediate in the synthesis of laurolactam, the monomer for polyamide 12 （VESTAMID® L）. The synthesis of laurolactam starts with cyclododecane, which is converted sequentially into cyclododecanol, cyclododecanone and cyclododecanone oxime
• it is also used in UV absorbers.
• in the perfume industry, CDON is used particularly in the production of well-known musk perfumes.
• fragrances of a woody character are also produced using CDOL.

Cyclododecene （CDEN） -C12 Rings

The singly unsaturated cyclic hydrocarbon cyclododecene （CDEN） is the latest member of our C12 family of products. CDEN is a colorless liquid with a boiling point of 241°C.

CDEN is formed by selective hydrogenation of cyclododecatriene. We have developed for this purpose a new and highly economical process for selective hydrogenation of cyclododecatriene.

• CDEN is a chemical intermediate for production of plastics.
• it is used in the synthesis of aromatic principles, for example, for production of musk fragrances and perfumes with a woody note.

1,12-Dodecanedioic Acid （DDA） -C12 Rings

The linear dicarboxylic acid 1,12-dodecanedioic acid （DDA） has a melting point of 125°C. It is virtually insoluble in water at room temperature.

DDA is formed by oxidative cleavage of cyclododecanol or cyclododecanone with nitric acid.

• the most important area of application of DDA is for production of polyamides such as polyamide 612 （VESTAMID® D） or specialty polyamides such as TROGAMID® CX, and of polyesters.
• DDA is also used in the production of hotmelt adhesives and coatings.
• DDA finds application in corrosion inhibitors.
• DDA also serves as a starting material in the fragrance industry.

1,5-Cyclooctadiene （COD） -C8 Rings

The doubly unsaturated cyclic hydrocarbon cis, cis-1,5-cyclooctadiene （COD） is a colorless liquid with a pungent odor and a boiling point of 151°C.

COD is formed by the dimerization of butadiene.

COD is an important starting material for synthesis of cyclic C8 compounds. By the use of appropriate reaction engineering, chemical reactions can be carried out selectively at one or both of the double bonds.

• thus selective hydrogenation can be used to produce cyclooctene, the monomer of polyoctenamer.
• bromination produces an effective flame retardant for plastics.
• COD also serves in the fragrance industry for production of fragrances with an earthy note.

Cyclooctene （COE） -C8 Rings

The singly unsaturated cyclic hydrocarbon cyclooctene （COE） is a colorless liquid with a boiling point of 145°C.

COE is formed by selective hydrogenation of cyclooctadiene.

• we produce COE mainly for the manufacture of polyoctenamer by ring-opening polymerization.
• ozonolysis of COE yields suberic acid.
• various perfumes are obtained via a number of intermediate stages.
• thermolysis of COE yields 1,7-octadiene, which is also used industrially.

Cyclooctane （COAN） -C8 Rings

The saturated cyclic hydrocarbon cyclooctane （COAN） is a colorless liquid with a boiling point of 151°C and a freezing point of 12°C.

COAN is formed by catalytic hydrogenation of 1,5-cyclooctadiene, which is easily obtained by the dimerization of butadiene.

• COAN is very easily soluble in apolar substances. It can be used as a solvent whenever the special chemical inertness of saturated cyclic hydrocarbons is required.

Vinylcyclohexene （VCH） -C8 Rings

The doubly unsaturated cyclic hydrocarbon 4-vinylcyclohexene （VCH） is a colorless liquid with a boiling point of 126°C and a pungent odor.

VCH is formed by dimerization of butadiene.

• VCH is a precursor in the production of flame retardants.
• it is hydrogenated to ethylcyclohexane, a solvent for apolar substances.
• it also serves as an intermediate in the synthesis of specialty chemicals.

Ethylcyclohexane （ECH） -C8 Rings

The fully saturated hydrocarbon ethylcyclohexane （ECH） is distinguished by an unusual property: with a freezing point of -111°C and a boiling point of 131°C, it has an extraordinarily long liquid range of 242 K.

ECH is formed by catalytic hydrogenation of 4-vinylcyclohexene, a dimerization product of butadiene. We supply ECH of average purity 85%, the other component present being ethylbenzene.

• thanks to its saturated character, ECH is an outstanding solvent for apolar substances.