Submitted to: Green Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/27/2010
Publication Date: 9/22/2010
Publication URL: http://hdl.handle.net/10113/46826
Citation: Carpenter, C.A., Kenar, J.A., Price, N.P. 2010. Preparation of saturated and unsaturated fatty acid hydrazides and long chain C-glycoside Ketohydrazones. Green Chemistry. 12(11):2012-2018. DOI: 10.1039/c0gc00372g. Interpretive Summary: There are potentially large domestic markets for new detergents made from renewable agricultural materials. This paper describes green technology to make chemicals from vegetable oils. The chemicals described (fatty acid hydrazides) are useful intermediates for the preparation of sugar-based detergents that are described in an accompanying publication. We have obtained excellent yield of these compounds even when using natural plant oils (corn oil, sesame oil, olive oil) as starting materials. An economic, simple route to these compounds will allow their production as renewable "green" chemicals that can be used to make a new sugar-based detergents that are being development by ARS.
Technical Abstract: A method is described to prepare both saturated and unsaturated fatty acid acyl hydrazides using lipase as a catalyst. Hydrazides were generated from fatty acid methyl esters as well as directly from vegetable oils, and an organic co-solvent was not needed to maintain the integrity of the unsaturated fatty acids. Both C. antarctica and M. miehei lipase were used to catalyze the reaction and provided the desired acyl hydrazides with similar yields of 82.8% and 84.6%, respectively. Analysis of the products by MALDI-TOF-MS and GC-MS fragmentation pathways shows pure products free of starting methyl esters or triacylglycerols. These hydrazide molecules can be used as building blocks to produce naturally derived C-glycoside surfactants, whereby, the sugar moiety servers as the polar head group while the hydrazide alkyl chain is the non-polar component.