Decylketene dimer

If desired, decylketene dimer can be isolated at this point by filtering the reaction mixture and concentrating the filtrate. The mixture should be handled at all times under anhydrous conditions. The filtration should be carried out by the inverted filtration method.2 Difficulties are usually encountered in the filtration step since the amine salt frequently separates as a gel. Seeding the ether solution of lauroyl chloride with triethylamine hydrochloride usually aids in preventing this gel formation. It is necessary to rinse the amine salt several times with ether to extract the dimer, which is usually contaminated with traces of triethylamine hydrochloride. 

Laurone has been prepared by hydrating and decarboxylating decylketene dimer.3 It has also been prepared by distilling calcium laurate 4 by heating lauric acid with phosphorus pent-oxide 5 by heating barium laurate under reduced pressure 6 by the ester condensation of ethyl laurate with sodium ethoxide 7 or of methyl laurate with sodium hydride 8 followed by ketonic hydrolysis by catalytic ketonization of lauric acid over a chromate catalyst 9 or by passing lauric acid over thorium dioxide at 400°.10... 

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