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Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins

United States Patent

September 12, 2006
View the Complete Patent at the US Patent & Trademark Office
Ames Laboratory - Visit the Iowa State University Research Foundation - Office of Intellectual Property & Technology Transfer Website
Mechanochemical Preparation of Phosphonium Salts and Phosphorus Ylides
The present invention provides a method of preparing a phosphonium salt of the formula [R.sup.1R.sup.2R.sup.3P--CR.sup.4R.sup.5R.sup.6]X, comprising ball-milling a phosphine of the formula R.sup.1R.sup.2R.sup.3P with a compound of the formula XCR.sup.4R.sup.5R.sup.6; a method of preparing a phosphorus ylide of the formula R.sup.1R.sup.2R.sup.3P.dbd.CR.sup.4R.sup.5, comprising ball-milling a phosphonium salt of the formula [R.sup.1R.sup.2R.sup.3P--HCR.sup.4R.sup.5]X in the presence of a base; and a method of preparing an olefin of the formula R.sup.4R.sup.5C.dbd.CR.sup.7H or R.sup.4R.sup.5C.dbd.CR.sup.7R.sup.8, comprising ball-milling a phosphorus ylide of the formula R.sup.1R.sup.2R.sup.3P.dbd.CR.sup.4R.sup.5 with a compound of the formula R.sup.7C(O)H or R.sup.7C(O)R.sup.8. The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.
Pecharsky; Vitalij K (Ames, IA), Balema; Viktor P (Ames, IA), Wiench; Jerzy W (Ames, IA), Pruski; Marek (Ames, IA)
Iowa State University Research Foundation, Inc. (Ames, IA)
10/ 744,932
December 22, 2003
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH AND DEVELOPMENT This invention was made in part with Government support under Contract Number W-7405-ENG-82 awarded by the Department of Energy (DOE). The Government may have certain rights in this invention.