Chemical intermediates and derivatives from oleyl alcohol

Several series of compounds were prepared from oleyl alcohol which may prove useful as lubricants and plasticizers. The reactions involved addition to the double bond and replacement of the hydroxyl moiety. One series of compounds is characterized l-R′, 9(10)R octadecane where l-R′ signifies the replacement of hydroxyl by ethoxy,tert-butylphenyl,tert-butoxy and phenyl. Examples of additions across the double bond 9(10)R, include hydrogen, methoxy,tert-butoxy,tert-butylphenyl, and phenyl. Other test series were 9(10)-R, 27(28)-R-hexatriacontane andbis 9(10)-R-octadecyl] ether where R signifies additions across a pair of double bonds. Additions in these series include methoxy, ethoxy,tert-butoxy,tert-butylphenyl, 2-ethylhexoxy, and phenyl. Derivatives of octadecane were fluid and several had fairly low pour points. The derivatives of hexatriacontane and dioctadecyl ether were either low-melting solids or liquids. Details concerning the synthesis and several physical properties are presented.