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

Patent · Tue Sep 12 00:00:00 EDT 2006

OSTI ID:1175910

Pecharsky, Vitalij K; Balema, Viktor P; Wiench, Jerzy W; Pruski, Marek

The present invention provides a method of preparing a phosphonium salt of the formula [R¹R²R³P--CR⁴R⁵R⁶]X, comprising ball-milling a phosphine of the formula R¹R²R³P with a compound of the formula XCR⁴R⁵R⁶; a method of preparing a phosphorus ylide of the formula R¹R²R³P--CR⁴R⁵, comprising ball-milling a phosphonium salt of the formula [R¹R²R³P --HCR⁴R⁵]X in the presence of a base; and a method of preparing an olefin of the formula R⁴R⁵C--CR⁷H or R⁴R⁵C--CR⁷R⁸, comprising ball-milling a phosphorus ylide of the formula [R¹R²R³P--CR⁴R⁵ with a compound of the formula R⁷C(O)H or R⁷C(O)R⁸. 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.

• Research Organization: Iowa State Univ., Ames, IA (United States); Ames Laboratory (AMES), Ames, IA (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: W-7405-ENG-82
• Assignee: Iowa State University Research Foundation, Inc. (Ames, IA)
• Patent Number(s): 7,105,714
• Application Number: 10/744,932
• OSTI ID: 1175910
• Resource Relation: Patent File Date: 2003 Dec 22
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY