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The preparation of 2 heptanol and investigations into methods for the preparation of alpha napthylisocyanate as preliminary syntheses for the determination of the properties of the urethanes of four isomeric heptyl alcohols

Citation

Thompson, Donald R. (1928) The preparation of 2 heptanol and investigations into methods for the preparation of alpha napthylisocyanate as preliminary syntheses for the determination of the properties of the urethanes of four isomeric heptyl alcohols. Bachelor's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-12062004-143231

Abstract

For a great many years certain reagents have been investigated which will convert alcohols into solid substances. The melting points of these solid substances were then determined and as a consequence the alcohols under consideration could be detected. There have been several reagents proposed, the most satisfactory of which have been phenylisocyanate and alpha naphthylisocyanate, up to the present time. Particularly with the phenylisocyanate it has been noted that with certain of the higher alcohols, the greater the number of carbon atoms there was in the chain, the lower the melting point of the solid derivative obtained, so that when it was attempted to secure solid derivatives of certain of these six and seven carbon atom alcohols it was found impossible to get a substance which was a solid at ordinary temperatures, and which would serve as a convenient means for the detection of the alcohols in question. Only very recently has alpha naphthylisocyanate been proposed and it seems to be a very promising reagent judging from the small amount of work which has been done and from the success that has been attained.

In connection with another research problem in the laboratory, it was desired to detect four heptyl alcohols, namely, 1 heptanol, 2 heptanol, 3 heptanol, and 4 heptanol. There were sufficient quantities of 3 heptanol and 4 heptanol accessible, ten grams of 1 heptanol were purchased from the Eastman Kodak Company, and it was found necessary to synthesize 2 heptanol as it could not be purchased at any of the leading dealers in organic chemicals. Alpha naphthylisocyanate is sold by the Eastman Company but the price is very high and as a sufficient quantity for this research would cost quite a sum it was decided to try to find satisfactory method for its preparation.

After the reagent and the alcohol had been prepared it was decided to convert the alcohols into the urethanes, purify them by recrystallization in ligroin, making a melting point determination of these urethanes, and finally subjecting each urethane to a nitrogen determination by the Kjeldahl method and comparing the nitrogen content found to that calculated from the formula of the particular urethane in question.

It was also decided to investigate other alcoholic derivatives is time permitted.

Item Type:Thesis (Bachelor's thesis)
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemical Engineering
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Lucas, Howard J.
Thesis Committee:
  • Unknown, Unknown
Defense Date:6 June 1927
Record Number:CaltechETD:etd-12062004-143231
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-12062004-143231
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:4811
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:08 Dec 2004
Last Modified:26 Dec 2012 03:12

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