An investigation of the oxidative cleavage of the double bond

The following investigation was undertaken to find a method for the oxidative cleavage of the double bond, using oleic acid. The primary purpose of this investigation was to find a cheap method of splitting the double bond in oleic acid and obtaining the saturated fatty acids formed therefrom. The procedure used in the attempt to accomplish these results was the auto-oxidation of the oleic acid. This was carried out with and without a catalyst, and also, in the presence of a chemical oxidizing agent. The results from the runs, with and without a catalyst, were poor in that no split of the double bond took place, but in most cases more favorable results were obtained in the presence of catalysts. The results were positive in the one case in which the chemical oxidizing agent was used with the catalyst. This run gave a split of the double bond and warrants further investigation. 1. No split of the double linkage in oleic acid was obtained from its autoxidation over a period of four hundred twenty-five hours, with or without a catalyst. 2. The ozonide of oleic acid was not formed, although the presence of peroxide oxygen was detected. 3. Iron oxide (Fe₃O₄) was a positive autoxidation catalyst, whereas, vanadium pentoxide was a negative catalyst. 4. Cleavage of the double linkage was obtained when concentrated nitric acid was used as the oxidizing agent in presence of vanadium pentoxide as the catalyst. The split was very slight, as only 0.4 gram of suberic acid was isolated from 89.5 grams of oleic acid.

Name thesis:degree_name

M.S.

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Agricultural and Mechanical College and Polytechnic Institute

Year dc:date.issued

1941

Author dc:creator

• Hargis, Oscar Lee

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10919/104482

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/104482