Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Dehydrogenation of Secondary Alcohols with Reduced Copper. V. Catalytic Dehydrogenation of sec-Butyl Alcohol
Kazuaki Kawamoto
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1961 Volume 34 Issue 6 Pages 799-803


It was confirmed that ethyl methyl ketone and 5-methyl-3-heptanone are produced from sec-butyl alcohol with reduced copper alone. Two distinct types of reduced copper were prepared by precipitation with sodium hydroxide and with potassium carbonate. They differ somewhat in their ability to promote dehydrogenation of sec-butyl alcohol and differ greatly in their power to bring about condensation. The copper catalyst prepared with potassium carbonate acts to dehydrogenate sec-butyl alcohol at all the temperatures examined (185∼325°C), giving ethyl methyl ketone, but the catalyst prepared with sodium hydroxide acts to dehydrogenate and to condense simultaneously at a certain temperature (220°C), giving 5-methyl-3-heptanone along with ethyl methyl ketone, and this affords a new synthetic method for 5-methyl-3-heptanone. sec-Butyl alcohol was converted into ethyl methyl ketone in 94∼96% yield with no side reaction by passing it over these catalysts at 325°C.

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