IWMEfflKWEra CHEMICAL
PLANTS
IMPROVING SECURITY GAO suggests Department of Homeland Security be given more authority RISKY BUSINESS The New York City skyline is seen behind a chemical plant in a New Jersey area nicknamed "the most dangerous two miles in America."
A
LTHOUGH THE DEPARTMENT
of Homeland Security has taken steps to shield the chemical sector from terrorist attacks, the Government Accountability Office finds that much more needs to be done. DHS has tagged 3,400 chemical facilities that, if attacked, would pose great harm to human life and health. Yet, GAO notes in a recent report, current laws give D H S only limited authority to regulate security at those plants. DHS has had to rely on industry's voluntary efforts,
and GAO says, "The extent to which companies are addressing security is unclear." GAO suggests that Congress consider legislation giving DHS the mantle to require industry to address security at its facilities. "We agree with GAO that DHS should have the authority over security of the nation's critical infrastructure, including the chemical sector," says Chris VandenHeuvel, American Chemistry Council spokesman. VandenHeuvel says ACC supports rapid passage of "tough legislation that focuses solely on security, not on issues that divert attention from antiterrorism, such as unhelpful provisions that would let government bureaucrats interfere with
O R G A N O M E T A L L I C S
OLEFIN METATHESIS Highly active, water-soluble catalyst promises greener, cheaper processes
TWEAKED A polytethylene glycol) chain makes this catalyst soluble in water and organic solvents.
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O
LEFIN METATHESIS IS AL-
ready regarded as an important way to make carboncarbon bonds, but the reaction could become even more practical, thanks to a new, highly active, water-soluble catalyst. T h e catalyst, developed by California Institute of Technology Q Q l_l chemistry Nobel Laureate Robert H. Grubbs 'n and grad student Soon Hyeok Hong, shows "unprecedented activity" in several olefin metathesis reactions in water (J. Am. Chem. Soc, published online Feb. 25, dx.doi. org/10.1021/ja05845k). Because olefin metathesis is widely used in industry, the reagent could make these processes more environmen-
C & E N / MARCH 6, 2006
tally friendly and less expensive. In olefin metathesis, two carbon-carbon double bonds react to form two new carbon-carbon double bonds, exchanging substituents attached to the carbon atoms in the process. It can lead to substituent swapping, ring closure, diene formation, or polymerization. The reaction relies on a catalyst, and until now, no watersoluble catalyst has been stable enough to efficiently mediate the reaction in aqueous solution. G r u b b s and H o n g added a polyethylene glycol) or PEG chain to the commercially available Hoveyda-Grubbs second-generation catalyst. This small change leads to a significant alteration in the
company production processes." He is alluding to inherently safer technologies (1ST) that GAO says can potentially "lessen the consequences of a terrorist attack by reducing the chemical risks present at facilities." GAO suggests that DHS and EPA study ISTs security benefits. But Nicholas A. Ashford, professor of technology policy at Massachusetts Institute of Technology, points out that 12 years ago EPA "sponsored research at M I T on the advantages of using 1ST, which it unfortunately ignored." Sen. James M. Inhofe (R-Okk), chairman of the Environment & Public Works Committee, however, released a statement calling 1ST "a concept that environmental special interests have been promoting. It is not a solution for improving security, and DHS opposes its use as such." But, asks Greenpeace spokesman Rick Hind, "if 1ST could prevent both a terrorist attack and a Bhopal-type accident, who would Oppose it?"—LOIS EMBER
catalyst's chemistry, rendering it soluble in both water and certain organic solvents. Grubbs thinks the P E G causes the catalyst to form micellelike structures in aqueous solution. These structures, he adds, probably protect the metal center and account for the catalyst's stability. Ring-closing metathesis reactions carried out in aqueous solution with Grubbs and Hong's catalyst proceed exceptionally well, resulting in good to excellent yields of five- and six-membered rings. The catalyst also is highly active in cross-metathesis and in ring-opening metathesis polymerization reactions. "This is critical and timely progress in catalytic olefin metathesis," comments Boston College chemistry professor Amir H. Hoveyda. It's "an advance that paves the way for this powerful reaction to be applied to many important transformations that must be carried out in water."—BETHANY HALFORD WWW.CEN-0NLINE.ORG
