I. The Catalytic Decomposition of n-Butyl Alcohol. The Equilibrium Between the Three Normal Butenes. II. The Use of Crotonaldehyde in the Synthesis of Lepidine

Author: Rose, Robert Selden

Year: 1933

Degree: Dissertation (Ph.D.)

Advisor: Lucas, Howard J.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/72bp-qf22

Abstract

I.

n-Butyl alcohol has been dehydrated at 350-450° with various catalysts. Soda lime, sodium aluminate and sodium hydroxide are without effect. Kaolin, tungsten oxide on asbestos and thorium oxide on asbestos, give good results. The compositions of the butene mixtures so obtained have been determined.

l-Butene and 2-butene respectively have been passed over pumice stone impregnated with phosphoric acid at 350, 400 and 500°. Equilibrium has been reached at 350 and 400°, and equilibrium constants and free energies have been calculated for the reactions:

(1) l-butene ⇄ trans 2-butene

(2) l-butene ⇄ cis 2-butene

(3) trans 2-butene ⇄ cis 2-butene

II.

The synthesis of lepidine has been attempted in three ways, using crotonaldehyde as a starting material:

(1) By preparing an aldehyde-ammonia from B-phenyl butyracetal and ammonia, followed by ring closure with the use of AlCl3.

(2) By the condensation of aniline with B-chlor butyracetal.

(3) By ring closure of B-phenyl butyric bromamide, with the use of AlCl3.

A new compound, B-phenyl butyric bromamide has been prepared.

A new method for the preparation in good yield of B-phenyl butyric acid has been outlined.

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