This section is from the book "Alcohol, Its Production, Properties, Chemistry, And Industrial Applications", by Charles Simmonds. Also available from Amazon: Alcohol: Its Production, Properties, Chemistry, And Industrial Applications.
It is of interest to note that proposals for the manufacture of synthetic fusel oil have been put forward. In one method gasoline is chlorinated, and the resulting chlorinated hydrocarbons heated with methyl alcohol and a formate to 140-190o under pressure. The product obtained consists of monohydric alcohols of high boiling point, which, it is claimed, can be used as a substitute for fusel oil.4
In another process, a petroleum distillate boiling between 25° and 75°, containing pentanes and hexanes, is treated with chlorine so as to produce chiefly monochloro-derivatives. These are then heated with an acetate to 170-250° at a pressure of 300 lb. per square inch, the product furnishing a mixture of pentyi and hexyl alcohols. A further yield of these alcohols is obtained by hydro-lysing the olefines which are produced at the same time.5
By another method, the stearic acid ester of the higher alcohol is formed through the action of sodium stearate upon pentyl or hexyl chloride, and the alcohol obtained by hydrolysing the ester.6 Stearic acid and solid caustic soda are heated together in a jacketed vessel at 200-240°, and when the water has been expelled, a mixture of pentyl and hexyl chlorides is introduced at the bottom of the vessel. A part of the chlorides reacts with the sodium stearate, whilst another part is converted into olefines, and some distils unchanged. After separating the volatile products, the stearic ester remaining is cooled to about 150°, and decomposed by heating again with caustic soda to 200-240°. The resulting alcohol is then distilled off in the presence of a little water or steam.
1 Ber., 1907, 40, 1027.
2 Revista Acad. Sci. Madrid, 1904; 1, 217; see J. Chem. Soc. (Abst.), 1910, 98, [i], 350.
3 It has recently been shown that sugar, by fermentation under special conditions, can yield as much as 21 per cent. of glycerol. (K. Schweitzer, Helv. Chim. Acta, 1919, 2, 167.)
4 Brooks and Essex, U,S.P., 1221667, 1917.
5 U.S.P., 1214919, 1917.
6 B.P., 119249, 1917.
 
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