PATENTS

      207.          BOWMAN, N. J., AND WEITKAMP, A. W.  (Standard Oil Co. of Indiana).  Separation of Alcohols.  United States Patent 2,594,481, Apr. 29, 1952.  Chem Abs., vol. 47, 1953, p. 1181.

Separation is based on the formation of adducts between urea and esters of mono-Me branched alcohols and acids of at least 5 C atoms, whereas esters of more highly branched alcohols do not form such adducts.  Thus, crude C₁₀ alcohol mixture (from the CO-H₂ reaction) acetylated with AcCl and the esters 23 stirred 1 hr. with urea 120, MeOH 4, and pentane 126 parts yields a solid adduct, which, washed with pentane, treated with H₂O, and extracted with Et₂O yields 15 parts decyl acetate.  The wash liquor can be retreated, as above, to give smaller amounts of the same ester, and the pure product is saponified to pure decyl alcohol.  The adduct formed after the 3d treatment with urea on hydrolysis yields pure 2-undecanol, and the wash fluid from this adduct yields mixed branched-chain alcohols.  Similarly, n-C₈H₁₇Oac forms a urea adduct in MeOH-isooctane mixture, whereas CH₁₁-CHMeOAc does not form such an adduct.  The heat of the reaction of urea with n-C₈H₁₇OH is 8.5 kcal, per mol, that of C₆H₁₃CHMeOAc only 1.3 kcal. Per mol.