Cyclododecatriene
Encyclopedia
Cyclododecatriene C12H18 is a cycloalkene
with three alkene
groups. The 1,3,5-trans-trans-cis isomer
has some industrial importance and is obtained by cyclotrimerization of butadiene with titanium tetrachloride
and an organoaluminium
co-catalyst :
This compound is the raw material for the production of dodecanedioic acid
(4) through hydrogenation
to cyclododecane (2) followed by air oxidation in the presence of boric acid
at elevated temperatures to a mixture of the alcohol
(3a) and the ketone
(3b). In the final step this mixture oxidized further by nitric acid
:
The acid is used in the production of polyamide
s.
Cycloalkene
A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Unless the rings are very large, cycloalkenes are...
with three alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
groups. The 1,3,5-trans-trans-cis isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
has some industrial importance and is obtained by cyclotrimerization of butadiene with titanium tetrachloride
Titanium tetrachloride
Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is an unusual example of a metal halide that is highly volatile...
and an organoaluminium
Organoaluminium
Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium bond. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the...
co-catalyst :
This compound is the raw material for the production of dodecanedioic acid
Dodecanedioic acid
Dodecanedioic acid is a dicarboxylic acid mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitor, surfactant, and engineering plastics....
(4) through hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
to cyclododecane (2) followed by air oxidation in the presence of boric acid
Boric acid
Boric acid, also called hydrogen borate or boracic acid or orthoboric acid or acidum boricum, is a weak acid of boron often used as an antiseptic, insecticide, flame retardant, as a neutron absorber, and as a precursor of other chemical compounds. It exists in the form of colorless crystals or a...
at elevated temperatures to a mixture of the alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
(3a) and the ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
(3b). In the final step this mixture oxidized further by nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
:
The acid is used in the production of polyamide
Polyamide
A polyamide is a polymer containing monomers of amides joined by peptide bonds. They can occur both naturally and artificially, examples being proteins, such as wool and silk, and can be made artificially through step-growth polymerization or solid-phase synthesis, examples being nylons, aramids,...
s.