Cyclododecanone 1,5,9-Cyclododecatriene

Cyclododecane Cyclododecanol Cyclododecanone 1,5,9-Cyclododecatriene c/s-Cyclododecene f/3/i5-Cyclododecene c/s-9-Cycloheptadecen-1-one 1,3-Cycloheptadiene Cycloheptanamine... 

Dodecanedioic Acid. Dodecanedioic acid (DDDA) is produced commercially by Du Pont ia Victoria, Texas, and by Chemische Werke Hbls ia Germany. The starting material is butadiene which is converted to cyclododecatriene usiag a nickel catalyst. Hydrogenation of the triene gives cyclododecane, which is air oxidized to give cyclododecanone and cyclododecanol. Oxidation of this mixture with nitric acid gives dodecanedioic acid (71). 

Cyclododecene may be prepared from 1,5,9-cyclododecatriene by the catalytic reduction with Raney nickel and hydrogen diluted with nitrogen, with nickel sulfide on alumina, with cobalt, iron, or nickel in the presence of thiophene, with palladium on charcoal, with palladimn chloride in the presence of water, with palladium on barium sulfate, with cobalt acetate in the presence of cobalt carbonyl, and with cobalt carbonyl and tri- -butyl phosphine. It may also be obtained from the triene by reduction with lithium and ethylamine, by disproportionation, - by epoxidation followed by isomerization to a ketone and WoliT-Kishner reduction, and from cyclododecanone by the reaction of its hydrazone with sodium hydride. ... 

Production. The main industrial syntheses start from compounds produced from cyclododecatriene either by ring expansion of cyclododecanone or by depolymerization of polyesters of 15-hydroxypentadecanoic acid (from 1,12-dodecanediol). 

Concerning other reactions that make use of nitrous oxide as the oxidant, a process developed by BASF is worth mentioning, which involves the synthesis of cyclododecanone, a raw material for Nylon-12 and Nylon 6-12 [12]. Cyclodode-canone is oxidized to 1,12-dodecanedioic acid by oxidative cleavage with nitric acid. It is currently made by a five-step sequence from cyclododecatriene. The first step of the new process is the synthesis of cyclododecatriene from butadiene, which is then reacted with nitrous oxide, to produce cyclododecadienone, which is finally hydrogenated to cyclododecanone. The yield to cyclododecanone is significantly higher than with the conventional process, waste is reduced and investment costs are lower. BASF already has a contracted customer and is building a plant due to come on stream in 2009. 

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