1,5,9-Cyclododecatriene manufacture

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Butadiene could also be trimerized to give cyclododecatriene. The trimer is again used by Hulls to manufacture nylon 12 and Vestamid . The codimerization of butadiene and ethylene is used by DuPont to manufacture 1,4-hexadiene, one of the monomers of EPDM (ethylene, propylene, diene, monomers) rubber. The role of the diene monomer in EPDM rubber is to provide with two double bonds of different reactivities. The more reactive, terminal double bond takes part in the polymerization with ethylene and propylene. The less reactive internal one is used later on for cross-linking. These important catalytic reactions are shown in Fig. 7.6. 

Cyclooctadiene (COD) is an intermediate for the manufacture of poly-octenamers, while 1,5,9-cyclododecatriene (CDT) is the starting material for the manufacture of dodecanoic acid and lauryl lactam. The latter is converted to the polyamide fiber Vestamide (DuPont). Both COD and CDT are made from butadiene (Equations 21 and 22). 

Nylon 12 is produced in U.S., Japan, and Europe with the original development coming from Europe. All current manufacturing processes of this polyamide, formed by ring opening polymerization of lauryl lactam, are based on cyclododecatriene. This ring compoimd can be obtained by... 

Multi-ton quantities of 1,5-hexadiene have been manufactured in alkene metathesis semi-works units and the process has been studied in a small specialty olefin pilot plant by the Phillips Company. Feedstocks for this process are the commerically available butadiene derivatives (1,5-cyclooc-tadiene and 1,5,9-cyclododecatriene). The use of excess ethylene and a... 

Butadiene could also be trimerized to give cyclododecatriene. The latter is used in the manufacture of nylon 12 polymers with trade names Quina and Vestamid . As shown by reactions 7.2.4 and 7.2.5, syntheses of both the polymers start with cyclododecatriene and involve multiple steps. 

The selective hydrogenation of mixtures of cyclododecatriene (CDT) isomers, easily available through cyclotrinmizatitm of butadiaie, represents a convenient route to cis- and trans-cyclododecene (CDE). These lattm- conqxMinds are of great practical importance because can be employed to prepare compounds such as 1,12-dodecandioic acid, 1,12-diaminododecane, 12-amminododecanoic acid lactam, which are monomers for polyamide manufacture, and cyclododecanecarboxilic acid, a pesticide, and its esters used as plasticizm. 

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