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MIT moves toward greener chemistry
Date:9/3/2010

ly done in two steps. First, three of the atoms in P4 are replaced with chlorine, resulting in PCl3 a phosphorus atom bound to three chlorine atoms.

Those chlorine atoms are then displaced by organic (carbon-containing) molecules, creating a wide variety of organophosphorus compounds such as those found in pesticides. However, this procedure is both wasteful and dangerous chlorine gas was used as a chemical weapon during World War I so chemists have been trying to find new ways to bind phosphorus to organic compounds without using chlorine.

A new reaction

Cummins has long been fascinated with phosphorus, in part because of its unusual tetrahedral P4 formation. Phosphorus is in the same column of the periodic table as nitrogen, whose most stable form is N2, so chemists expected that phosphorus might form a stable P2 structure. However, that is not the case.

For the past few years, Cummins' research group has been looking for ways to break P4 into P2 in hopes of attaching the smaller phosphorus molecule to organic compounds. In the new study, Cummins drew inspiration from a long overlooked paper, published in 1937, which demonstrated that P4 could be broken into two molecules of P2 with ultraviolet light. In that older study, P2 then polymerized into red posphorus.

Cummins decided to see what would happen if he broke apart P4 with UV light in the presence of organic molecules that have an unsaturated carbon-carbon bond (meaning those carbon atoms are able to grab onto other atoms and form new bonds). After 12 hours of UV exposure, he found that a compound called a tetra-organo diphosphane had formed, which includes two atoms of phosphorus attached to two molecules of the organic compound.

This suggests, but does not conclusively prove, that P2 forms and then immediately bonds to the organic molecule. In future studies, Cummins hopes to directly observe the P2 molecule, if it is indeed present.

Cummins
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Contact: Jessica Holmes
holmesj@mit.edu
617-253-2702
Massachusetts Institute of Technology
Source:Eurekalert

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