two men indicted for cfc smuggling into u.s

1
cal complex about 20 miles from Kobe, near Osaka. A fine chemicals plant there shut down because of water shortages, says a spokesman. But there was little damage at the site. The complex also houses fine chemicals research and envi- ronmental health science labs. Spokesmen for Hoechst, Exxon Chemical, Schering-Plough, and Searle, Monsanto's drug division—all of which have sales offices in Osaka—report their facilities suffered little or no structural damage. And they have accounted for their employees. George Peaff Two men indicted for CFC smuggling into U.S. A federal grand jury in Miami has in- dicted two men for illegally importing 126 tons of chlorofluorocarbons (CFCs) for sale in the U.S. The case is the largest seizure yet of illegally imported ozone-depleting chemicals, says the U.S. Attorney's Of- fice in Miami. The accused men face up to 20 years in jail and fines of more than $2 million if convicted. A black market in CFCs has devel- oped as supplies of the soon-to-be- banned chemicals decrease and their prices increase. The federal govern- ment set up an interagency task force last year to try to curtail the illegal ac- tivity (C&EN, Oct. 31,1994, page 4). "We've been very concerned for quite a while," says Stephen R. Seidel, director of the Environmental Protec- tion Agency's Stratospheric Protection Division. "This is the first major case, so we are extremely pleased. We antic- ipate there will be more." Under the Montreal Protocol on Sub- stances That Deplete the Ozone Layer, industrialized nations must phase out CFC production by Jan. 1, 1996 (stock- piled or recycled CFCs can still be used after that). In the U.S., EPA requires any company that produces or imports the chemicals to have a permit called a con- sumption allowance. And Congress has imposed an excise tax—cufrently $5.35 per lb—on the sale of ozone-depleting chemicals to encourage users to switch to substitutes. The Miami indictment charges Adi Dara Dubash and Homi N. Patel with conspiring to violate EPA and Internal Revenue Service regulations. They alleg- edly imported seven shipping contain- ers, each filled with 1,200 cylinders— each cylinder containing 30 lb of CFC-12 (CC1 2 F 2 )—under the pretext that the chemicals were just passing through the U.S. on the way to Mexico. "It's perfectly legal to bring CFC-12 into the U.S. without EPA consumption allowances if you are not going to sell it here," notes George H. White II, the Customs Service special agent in Miami who investigated the case. "In this in- stance, [Dubash and Patel] had all the paperwork completed as if they were going to ship it back out to a foreign company. But when the truck showed up to take the containers out of the bonded facility here in Miami, we fol- lowed and found they did not take them to a shipping company." The Alliance for Responsible Atmo- spheric Policy, a coalition of CFC users and producers, has urged industry and the public to be suspicious of CFCs of- fered for sale at prices below the excise tax. "We hope to see more of these indict- ments so people realize the government is serious," says David J. Stirpe, alliance ex- ecutive director. "The black market re- duces the incentive to shift to alterna- tives and penalizes legitimate companies who are complying with U.S. laws." Pamela Zurer Long, stable acetylenic carbon chains prepared They said it couldn't be done, so Rich- ard J. Lagow did it. In a paper published last week in Sci- ence [267, 362 (1995)], Lagow, a chemis- try professor at the University of Texas, Austin, and 10 coworkers reveal how they synthesized and identified a new material consisting of linear chains of 300 to 500 "naked" carbon atoms. Unlike the carbon atoms in diamond, graphite, or fullerenes, those in Lagow's carbon chains are sp-hybridized, so the chains contain alternating single and tri- ple bonds. Another group reported acet- ylenic carbon chains of this sort, with as many as 32 carbon atoms, as far back as 1972. But linear chains with hundreds of sp-hybridized carbon atoms were thought to be too unstable to prepare and isolate because of their reactivity. Lagow stabilizes these long acetylenic chains, whose structure has been con- firmed by a variety of techniques, by capping each end with a trifluoromethyl (CF 3 ), nitrile (C^N), or other group. His results, accumulated over 10 years, indi- cate the capped chains are surprisingly stable. The chains also have very useful prop- erties. They are highly soluble in most or- ganic solvents—"a novel feature for any form of carbon," he notes—and thus might be used to make carbon coatings. Because of their triple bonds, the chains pack more electron density than any oth- er form of carbon or known organic com- pound. So they might be the ultimate in molecular wires for molecular electronic devices. And since they have less thermal stability than graphite or diamond, they might be excellent precursors for dia- mond synthesis and graphite coatings. Lagow's team, which includes collab- orators at the University of Southern California and Texas A&M University, College Station, prepares linear "sp" carbon by laser vaporization of graph- ite—the same technique used by some groups to prepare fullerenes. Using a laser to vaporize graphite in the pres- ence of CF 3 or C=N radicals in his lab leads to carbon chains capped with CF 3 or C=N groups. When these capping radicals are absent, fullerenes such as C 60 and C 70 form. The team concludes from its experi- ments that laser vaporization produces unstable carbon-chain diradical species. When free radicals are present, they cap the carbon-chain species and allow their isolation. But in the absence of capping radicals, the acetylenic chains condense to form fullerenes or particu- late material known as fullerene soot. Lagow (left) and one of his coworkers, graduate student Han-Chao Wei. JANUARY 23,1995 C&EN 7

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Page 1: Two men indicted for CFC smuggling into U.S

cal complex about 20 miles from Kobe, near Osaka. A fine chemicals plant there shut down because of water shortages, says a spokesman. But there was little damage at the site. The complex also houses fine chemicals research and envi­ronmental health science labs.

Spokesmen for Hoechst, Exxon Chemical, Schering-Plough, and Searle, Monsanto's drug division—all of which have sales offices in Osaka—report their facilities suffered little or no structural damage. And they have accounted for their employees.

George Peaff

Two men indicted for CFC smuggling into U.S. A federal grand jury in Miami has in­dicted two men for illegally importing 126 tons of chlorofluorocarbons (CFCs) for sale in the U.S.

The case is the largest seizure yet of illegally imported ozone-depleting chemicals, says the U.S. Attorney's Of­fice in Miami. The accused men face up to 20 years in jail and fines of more than $2 million if convicted.

A black market in CFCs has devel­oped as supplies of the soon-to-be-banned chemicals decrease and their prices increase. The federal govern­ment set up an interagency task force last year to try to curtail the illegal ac­tivity (C&EN, Oct. 31,1994, page 4).

"We've been very concerned for quite a while," says Stephen R. Seidel, director of the Environmental Protec­tion Agency's Stratospheric Protection Division. "This is the first major case, so we are extremely pleased. We antic­ipate there will be more."

Under the Montreal Protocol on Sub­stances That Deplete the Ozone Layer, industrialized nations must phase out CFC production by Jan. 1, 1996 (stock­piled or recycled CFCs can still be used after that). In the U.S., EPA requires any company that produces or imports the chemicals to have a permit called a con­sumption allowance. And Congress has imposed an excise tax—cufrently $5.35 per lb—on the sale of ozone-depleting chemicals to encourage users to switch to substitutes.

The Miami indictment charges Adi Dara Dubash and Homi N. Patel with conspiring to violate EPA and Internal Revenue Service regulations. They alleg­

edly imported seven shipping contain­ers, each filled with 1,200 cylinders— each cylinder containing 30 lb of CFC-12 (CC12F2)—under the pretext that the chemicals were just passing through the U.S. on the way to Mexico.

"It's perfectly legal to bring CFC-12 into the U.S. without EPA consumption allowances if you are not going to sell it here," notes George H. White II, the Customs Service special agent in Miami who investigated the case. "In this in­stance, [Dubash and Patel] had all the paperwork completed as if they were going to ship it back out to a foreign company. But when the truck showed up to take the containers out of the bonded facility here in Miami, we fol­lowed and found they did not take them to a shipping company."

The Alliance for Responsible Atmo­spheric Policy, a coalition of CFC users and producers, has urged industry and the public to be suspicious of CFCs of­fered for sale at prices below the excise tax. "We hope to see more of these indict­ments so people realize the government is serious," says David J. Stirpe, alliance ex­ecutive director. "The black market re­duces the incentive to shift to alterna­tives and penalizes legitimate companies who are complying with U.S. laws."

Pamela Zurer

Long, stable acetylenic carbon chains prepared They said it couldn't be done, so Rich­ard J. Lagow did it.

In a paper published last week in Sci­ence [267, 362 (1995)], Lagow, a chemis­try professor at the University of Texas, Austin, and 10 coworkers reveal how they synthesized and identified a new material consisting of linear chains of 300 to 500 "naked" carbon atoms.

Unlike the carbon atoms in diamond, graphite, or fullerenes, those in Lagow's carbon chains are sp-hybridized, so the chains contain alternating single and tri­ple bonds. Another group reported acet­ylenic carbon chains of this sort, with as many as 32 carbon atoms, as far back as 1972. But linear chains with hundreds of sp-hybridized carbon atoms were thought to be too unstable to prepare and isolate because of their reactivity.

Lagow stabilizes these long acetylenic chains, whose structure has been con­firmed by a variety of techniques, by

capping each end with a trifluoromethyl (CF3), nitrile (C^N), or other group. His results, accumulated over 10 years, indi­cate the capped chains are surprisingly stable.

The chains also have very useful prop­erties. They are highly soluble in most or­ganic solvents—"a novel feature for any form of carbon," he notes—and thus might be used to make carbon coatings. Because of their triple bonds, the chains pack more electron density than any oth­er form of carbon or known organic com­pound. So they might be the ultimate in molecular wires for molecular electronic devices. And since they have less thermal stability than graphite or diamond, they might be excellent precursors for dia­mond synthesis and graphite coatings.

Lagow's team, which includes collab­orators at the University of Southern California and Texas A&M University, College Station, prepares linear "sp" carbon by laser vaporization of graph­ite—the same technique used by some groups to prepare fullerenes. Using a laser to vaporize graphite in the pres­ence of CF3 or C=N radicals in his lab leads to carbon chains capped with CF3

or C=N groups. When these capping radicals are absent, fullerenes such as C60 and C70 form.

The team concludes from its experi­ments that laser vaporization produces unstable carbon-chain diradical species. When free radicals are present, they cap the carbon-chain species and allow their isolation. But in the absence of capping radicals, the acetylenic chains condense to form fullerenes or particu­late material known as fullerene soot.

Lagow (left) and one of his coworkers, graduate student Han-Chao Wei.

JANUARY 23,1995 C&EN 7