that peptides could have participated in the origin of life on Earth. How life actually began probably is an unanswerable question. "Even if we make self-reproducing systems in test tubes, it doesn't mean that that's how life started" on Earth, Kauffman points out. Adds Rebek, "The debate over [this discovery's] relevance to prebiotic chemistry hasn't even begun yet." Ghadiri's group is already working on other peptide systems that have autocatalytic self-replicative properties. Aside from the prebiotic twist, he sees this as "the beginning of a very exciting period" as chemists learn how to design ever more sophisticated molecules that catalyze their own synthesis. Ron Dagani
Rexene rebuffs latest Huntsman buyout offer The board of directors of Rexene last week rejected Huntsman Corp.'s second bid to buy the polyethylene, polypropylene, and styrene producer. The new bid was for $15 per share, or about $287 million, a 7% increase over Huntsman's previous offer. Huntsman's latest proposal, made Aug. 1, also included the assumption of about $175 million in debt, which values the deal at about $462 million. But unlike Huntsman's first bid (C&EN, July 29, page 6), the second was made "unconditional," which means that Huntsman would forego an investigation of Rexene's books. According to Huntsman, Rexene's operations are worth more to it "than a pure financial analysis would dictate": It sees synergies and efficiencies in merging Rexene into Huntsman. On Aug. 2, when news of the sweetened bid reached Wall Street, Rexene's shares climbed $1V2, closing at $133/4. Rexene's board had until Aug. 8 to respond to Huntsman's newest tender, but unanimously rejected it on Aug. 5 as not being "in the best interest of the company's stockholders." Andrew J. Smith, Rexene's chairman and chief executive officer, says the company's strategic investment program—which includes expansion and modernization of its Odessa, Texas, plant—"is targeted to achieve profitable growth."
"We believe that this additional capacity—coupled with our ongoing actions to expand global market opportunities, reduce manufacturing costs, and improve margins—will yield significantly enhanced stockholder value," Smith says. In response to Rexene's latest rejection, Huntsman Chairman and CEO Jon M. Huntsman calls Rexene's decision "clearly harmful to the best interests of Rexene's shareholders." He adds that Huntsman Corp. will "continue to consider our options." Huntsman contends that Rexene's previously announced strategic investment program was already reflected in the $9V4 price of Rexene's stock on July 17, the date of his company's first offer. "It's a matter of simple arithmetic," says Huntsman. "Would Rexene's shareholders rather have $9 or $15?" He also points to Rexene's poor earnings so far this year. "Perhaps no company in the chemical industry has experienced such a dramatic reduction in earnings on a year-to-year basis,"
Huntsman: still considenng options
says Huntsman. He mentions that Rexene's earnings per share for secondquarter 1996 was 39 cents, compared with $1.07 per share for the same period in 1995. In making the second bid for Rexene, Huntsman said his firm's preferred method of growth is through friendly acquisitions. Huntsman alluded to making a nonfriendly bid for Rexene if the second offer was rejected: "It is in [a friendly] spirit that we decided to
make one last attempt to complete this acquisition directly with the Rexene board of directors prior to considering other options." The deal for Rexene represents Huntsman Corp.'s third potential failure this year in making a friendly takeover. Sterling Chemicals rejected Huntsman's overture in April, and talks between Deltech Corp. and Huntsman were ended in May. George Peaff
Two major metallocene joint ventures formed Two major deals were announced last week pitting metallocene catalyst rivals Dow Chemical and Exxon against each other in licensing linear low-density polyethylene technology. One joint venture links Dow Chemical with BP Chemicals; the other, Exxon Chemical with Union Carbide. The Dow-BP Chemicals' venture will combine Dow's Insite metallocene technology with BP's Innovene highproductivity gas-phase polyethylene technology, introduced early last year (C&EN, Jan. 23, 1995, page 8). The combined technology will be licensed to other polyethylene producers. The two companies began joint development of Insite and Innovene technologies in the second half of 1995. Working at BP's pilot plant in Lavera, France, near Marseilles, the two companies say they have proved out the combined technology, and they will soon expand trials to BP's semicommercial plant in Lavera, leading up to commercial-scale trials in 1997. The technology package will be ready for 1997 commercial delivery, say the companies, essentially as a "drop-in" package for retrofitting existing gasphase plants or for designing new ones. And the polyethylene produced can be processed on existing equipment, obviating the need for capital investment by polymer converters. BP already has 23 Innovene licensees with a combined manufacturing capacity of nearly 7.7 billion lb per year of polyethylene. The venture between Exxon Chemical and Union Carbide is remarkably similar to that of Dow and BP. It combines Exxon's metallocene technology with Carbide's Unipol process for producing polyethylene—again with the aim of liAUGUST 12,1996 C&EN
9
NEWS OF THE WEEK censing the combined technologies. The as-yet-unnamed venture seems to be further along than the Dow-BP venture in terms of commercialization. Exxon and Carbide say they have been negoti ating the deal for a year and plan to have the venture operational by the end of 1996. And Exxon has a plant in Mont Belvieu, Texas, that the company says can supply catalyst for 3 billion lb per year of polyethylene production, with additional investment in the plant com ing later this year. The two partners claim that the pro cess technology, which includes Exxon's supercondensed-mode reactor technol-
ogy, can double the output of Carbide's Unipol process reactors. Carbide cur rently has 46 Unipol licensees with 18.3 billion lb of annual capacity. In both joint ventures, although com bining technologies for licensing, the participants will keep their polyethyl ene production operations separate. The market potential for the technol ogies is huge. The polyethylene mar ket, currently at about 84 billion lb per year, is predicted to grow about 4% per year over the next decade to a total of probably more than 123 billion lb by 2005, with linear low-density polyeth ylene growing at twice that rate.
New route to amino alcohols developed A direct and efficient route to 1,2-amino alcohols from readily available ep oxides has been devised by chemists at Harvard University. Already drawing rave reviews from organic chemists, the reaction provides an immediately useful alternative to existing methods for making the important synthetic in termediates. "It begins to rival nature's elegance in producing the active site of an en zyme," comments Paul J. Reider, vice president for process research at Merck Research Laboratories in Rahway, N.J. Chemistry professor Eric N. Jacobsen and graduate students Jay F. Larrow and Scott E. Schaus developed the reac tion, which involves ring-opening of terminal epoxides with trimethylsilyl azide in the presence of a chiral catalyst [/. Am. Chem. Soc, 118, 7420 (1996)]. When a racemic mixture of epoxides
reacts in the presence of a single enantiomer of the catalyst, one epoxide enantiomer reacts more rapidly than the other. The strategy—called kinetic resolu tion—uses a chemical reaction to sepa rate enantiomers. It is useful when the racemic material is inexpensive and the enantiopure product is very valuable. Enantiopure 1,2-amino alcohols are hard to make. Jacobsen's reaction com plements a route from alkenes reported earlier by the group of chemistry pro fessor K. Barry Sharpless at Scripps Re search Institute (C&EN, Feb. 19, page 6). A "spectacular contribution," Sharp less says of Jacobsen's work. The reac tion's simplicity, he adds, guarantees its rapid adoption. Jacobsen's chiral catalyst is chromi um complexed with a tetradentate salen (from salicylide ethylenediami-
Catalyst controls which epoxide enantiomer reacts TMSO
{R,R) complex TMSN3
Q
Q
L^R
{S,S) complex TMSN3
+ R^
