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United States Department of Agriculture

Agricultural Research Service

Research Project: CRITICAL FLUIDS FOR PROCESSING AGRIMATERIALS Title: Increased Selectivity in the Formation of the Phenoxy Ether of Methyl Lesquerolate over Chloroalkyl-modified SBA-15-SO3H Catalysts

Authors
item Jackson, Michael
item Appell, Michael

Submitted to: Applied Catalysis A: Genera
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: November 2, 2009
Publication Date: December 22, 2009
Citation: Jackson, M.A., Appell, M.D. 2009. Increased selectivity in the formation of the phenoxy ether of methyl lesquerolate over chloroalkyl-modified SBA-15-SO3H catalysts. Applied Catalysis A: General. 373:90-97.

Interpretive Summary: In this research, we were able to prepare a new product from the seed oil from a native mustard, Lesquerella. Lesquerella holds promise as a new crop for the desert Southwest but, in order to be a viable new crop, new products must be manufactured using highly efficient means. We were able to improve the efficiency of the preparation of lesquerella derivatives by modifying the catalysts used in the process. This efficient preparation will allow for new uses for this novel seed oil, increasing its value to lesquerella growers and processors. Our new catalysts may have uses in other transformations of biomass and are new to the scientific community.

Technical Abstract: A novel synthetic catalysis was developed for selective modification of useful bioproducts from the oil of Lesquerella fendlerii, an agricultural commodity of increasing importance. Modification of the surface of the solid acid catalyst SBA-15-SO3H with the chloroalkyl groups CH2CH2Cl has improved the selectivity in the synthesis of the phenoxy ether of methyl 14-hydroxy-11-eicosenoate (methyl lesquerolate). A series of catalysts, SBA-15(EtCl)xSO3H where x = 0, 2, 4, 8, have been prepared and characterized by 13C CPNMR, surface properties and elemental analyses. Selectivity increased with increased loading of the chloroalkyl group. This selectivity can be attributed to the decrease in the rate of conversion of the phenoxy ether to the Friedel-Crafts adducts. This study demonstrates that synthetic approaches can develop novel catalysts to increase yields and selectivity for value-added bioproducts from new crops.

Last Modified: 11/22/2014
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