Cyclododecatriene

• Cyclododeca -1 ,5,9 -triene
• Cyclododecatriene
• CDT

• 4904-61-4 (unspecified)
• 4736-48-5 (Z, Z, Z)
• 676-22-2 (E, E, E)
• 2765-29-9 (E, Z, Z)
• 706-31-0 (E, E, Z)

Colorless to yellow liquid with a pungent odor

Liquid

0.8925 g · cm -3 ( E, Z, Z) 0.8895 g · cm -3 ( E, E, Z)

-1.5 ° C ( Z, Z, Z) 31-32 ° C. (E, E, E) -9 - 8 (E, Z, Z) -18 ° C. (E, E, Z)

108 ° C ( 2266 Pa) (Z, Z, Z) 237.5 ° C ( E, E, E) 224 ° C (E, Z, Z) 241.5 ° C ( E, E, Z)

0.1 mbar ( 20 ° C)

Practically insoluble in water (5 mg · l-1 at 20 ° C)

1.5005 (E, E, E) 1.5129 (E, Z, Z) 1.5061 (E, E, Z)

Risk

1780 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

1,5,9- cyclododecatriene (CDT ) is a chemical compound selected from the group of unsaturated cyclic hydrocarbons, specifically, the cycloalkenes, having three double bonds, which occurs in four isomeric forms.

Occurrence

Cyclododecatriene is a starting material and the main degradation product of hexabromocyclododecane ( HBCDD, CAS 25637-99-4 ).

Production and representation

The industrially important 1,5,9 -trans-trans -cis isomer [ (E, E, Z)- isomer ] can be obtained by cyclotrimerization of 1,3-butadiene with titanium tetrachloride and an organoaluminum co-catalyst:

Use

Cyclododecatriene is used as an intermediate in the production of chemical compounds, such as additives in building materials, fillers and insulating materials, resin for styrene -butadiene rubber, lubricants, fragrances, adhesives, and as a stabilizer and a plasticizer for thermoplastic polymers.

It serves as a starting material for the production of 1,12-dodecanedioic acid ( which is used in the production of polyamides ) by hydrogenation to cyclododecane, (2) followed by oxidation in the presence of boric acid. In this case, an alcohol (3a) and a ketone formed ( 3b ), which are further reacted with nitric acid to 1,12-dodecanedioic acid (4):

Safety

The vapors of 1,5,9 -cyclododecatriene can form (88 ° C, ignition temperature 244 ° C flash point) with air to form an explosive mixture.

Accident in the CDT production in Marl

In Germany CDT is produced by Evonik Industries in Marl Chemical Park. March 31, 2012 was a serious fire in the plant, as a result, two workers died. The cause of the fire, the overdose of a catalyst is assumed, according to investigations. The failure of the plant led to temporary shortages of supply of CDT -based products, which mainly affected the automotive and photovoltaic industry.