Method of manufacturing alkylene oxide adducts of an aliphatic alcohol

In a method of manufacturing alkylene oxide adducts of an aliphatic alcohol which comprises the steps of:

• a. admixing an alkylene oxide having 2 to 4 carbon atoms with the aliphatic alcohol in the presence of an acid catalyst selected from the group consisting of sulfuric acid, phosphoric acid and Friedel-Crafts catalysts to form an addition reaction mixture and
• b. distilling said reaction mixture to obtain an alcoholic distillate and a residue consisting essentially of an alkylene oxide adduct of the aliphatic alcohol;
• wherein said aliphatic alcohol is obtained by the liquid phase oxidation of a saturated aliphatic hydrocarbon having 8 to 20 carbon atoms in the presence of a boron compound by contacting with a molecular oxygen containing gas;
• the improvement comprising:
• i. combining said method of manufacturing alkylene oxide adducts with a method of manufacturing the aliphatic alcohol employed in step (a) which method comprises the steps of:
• a'. subjecting a saturated aliphatic hydrocarbon having 8 to 20 carbon atoms to oxidation by contacting said hydrocarbon with a molecular oxygen-containing gas in the liquid phase in the presence of a boron compound which is capable of forming a boric acid upon contact with water to form a reaction mixture containing a borate ester,
• b'. contacting said reaction mixture with water at a temperature between 20.degree. and 200.degree.C to form an organic layer and an aqueous layer, the weight ratio of water to said reaction mixture being between 10:1 to 1:10,
• c'. separating said layers,
• d'. subjecting said organic layer to saponification by contacting said organic layer with an aqueous alkali metal hydroxide,
• e'. adding a compound selected from the group consisting of orthoboric acid, metaboric acid, pyroboric acid and boric acid anhydride to the saponified organic layer to convert the alcohol in said organic layer into the corresponding borate ester,
• f'. distilling the resulting mixture of step (e') to obtain a crude borate ester residue and a distillate consisting essentially of unreacted hydrocarbon and volatile by-product,
• g'. recycling said distillate to oxidation step (a'),
• h'. contacting said residue with water at a temperature between 20.degree. to 200.degree.C to form a second organic layer and a second aqueous layer, the weight ratio of water to said residue being between 10:1 to 1:10,
• i'. separating said layers, and
• j'. distilling said second organic layer to obtain a product consisting essentially of said aliphatic alcohol;
• and
• ii. cycling 1 to 50% by weight of the distillate from step (b) of the method of manufacturing the alkylene oxide adducts to any of the steps (b'), (c'), (d'), (e') or (f') of the method of manufacturing the aliphatic alcohol.