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Mechanochemical Preparation of Phosphonium Salts and Phosphorus Ylides

Ames Laboratory

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Technology Marketing Summary

Researchers at Iowa State University and Ames Laboratory have developed a unique, solvent-free mechanochemical preparation method to prepare phosphonium salts and phosphorous ylides. The phosphorous ylides are then utilized in carrying out the solvent-free synthesis of desired organic compounds employing the Wittig-Horner reaction.

Description

This is a unique, solvent-free mechanochemical preparation method to prepare phosphonium salts and phosphorous ylides. The phosphorous ylides are then utilized in carrying out the solvent-free synthesis of desired organic compounds employing the Wittig-Horner reaction.

Benefits

The advantages include 1) Complete elimination of solvents from the reaction course, which would reduce the cost of the final product, and substantially reduce the hazardous and environmentally harmful chemical pollution and waste caused from the organic solvents (e.g. toluene, benzene, or hexane). 2) Extremely high selectivity of the chemical, and therefore, the relative absence of side products. 3) High yields of products (90% yields experienced). 4) Low processing temperatures close to ambient (no heat required). 5) Process should be scalable with simple and commercially available equipment.

Applications and Industries

* Simple, mechanochemical process for production of phosphonium salts and phosphorous ylides * Replaces traditional organic synthesis
* Suitable for chemical and pharmaceutical uses

More Information

This technology has been successfully demonstrated in the laboratory, and is available for licensing and commercial development.

Patents and Patent Applications
ID Number
Title and Abstract
Primary Lab
Date
Patent 6,730,812
Patent
6,730,812
Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins
The present invention provides a method of preparing a phosphonium salt of the formula [R.sup.1 R.sup.2 R.sup.3 P--CR.sup.4 R.sup.5 R.sup.6 ]X, comprising ball-milling a phosphine of the formula R.sup.1 R.sup.2 R.sup.3 P with a compound of the formula XCR.sup.4 R.sup.5 R.sup.6 ; a method of preparing a phosphorus ylide of the formula R.sup.1 R.sup.2 R.sup.3 P.dbd.CR.sup.4 R.sup.5, comprising ball-milling a phosphonium salt of the formula [R.sup.1 R.sup.2 R.sup.3 P--HCR.sup.4 R.sup.5 ]X in the presence of a base; and a method of preparing an olefin of the formula R.sup.4 R.sup.5 C.dbd.CR.sup.7 H or R.sup.4 R.sup.5 C.dbd.CR.sup.7 R.sup.8, comprising ball-milling a phosphorus ylide of the formula R.sup.1 R.sup.2 R.sup.3 P.dbd.CR.sup.4 R.sup.5 with a compound of the formula R.sup.7 C(O)H or R.sup.7 C(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.
Ames Laboratory 05/04/2004
Issued
Patent 7,105,714
Patent
7,105,714
Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins
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.
Ames Laboratory 09/12/2006
Issued
Technology Status
Technology IDDevelopment StageAvailabilityPublishedLast Updated
2847DevelopmentAvailable12/07/201003/04/2015

Contact AMES About This Technology

To: Stacy Joiner<joiner@ameslab.gov>