Catalytic Transfer Hydrogenation of Castor Oil

The main thickening agent or soap in multipurpose grease, lithium 12-hydroxystearate, is a chemical commodity for the auto industry. This compound is obtained from castor oil via a series of chemical transformations. The first step, hydrogenation of castor oil, has been developed into a laboratory e...

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Bibliographic Details
Published in:Journal of chemical education 2014-04, Vol.91 (4), p.575-578
Main Authors: Alwaseem, Hanan, Donahue, Craig J, Marincean, Simona
Format: Article
Language:English
Subjects:
Business
Carbon
Carbon dioxide
Carbon-carbon composites
Castor oil
Catalysis
College students
Comparative analysis
Fatty acids
Grease
Hydrogenation
Infrared spectroscopy
Lithium
Melting point
Melting points
NMR
Nuclear magnetic resonance
Oil
Organic chemistry
Ricinoleic acid
Students
Thickening
Thickening agents
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Summary:The main thickening agent or soap in multipurpose grease, lithium 12-hydroxystearate, is a chemical commodity for the auto industry. This compound is obtained from castor oil via a series of chemical transformations. The first step, hydrogenation of castor oil, has been developed into a laboratory experiment for second-year undergraduate organic chemistry. Students are introduced to catalytic transfer hydrogenation (CTH) as a method to reduce a carbon–carbon double bond in ricinoleic acid, the main fatty acid in castor oil. Students perform a comparative analysis based on calculation of several green metrics: atom economy, E factor, reaction mass efficiency, CO2 emissions, and costs. The product, hydrogenated castor oil, is characterized by several techniques: 1H NMR and IR spectroscopy, and melting point.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed300476u