INDUSTRY & BUSINESS Rubber — O l d a n d N e w
For centuries rubber bas come from- trees like that being tapped by this native on a Firestone plantation in Uiberia/ But with the world in turmoil^ natural rubber sources could b e cut off quickly. One likely
result would be early ^commercialization of synthetic natural rubbers like ,tKat made in this Gobdrich^Gulf Chemicals pilot plant at Avon Lake, Ohio
Polyisoprene Question: When? Rubber p e o p l e h a v e a c c e p t a b l e synthetic n a t u r a l r u b b e r s , but economics a n d d e m a n d a r e p r o b l e m s ITH the world in political turmoil, industry again takes a look at its raw materials position. Among items to consider: natural rubber. T h e r e are rumblings in the East Indies, threats of violence against plantation operators spawned by American troop movements in the Middle East. W h a t would h a p p e n should natural rubber supplies b e reduced or cut off completely? Offhand, these threats m a y b e just so much saber rattling, b u t they do raise a timely question: W h a t ' s the status of synthetic natural rubber—cis1,4-poly isoprene? How close is it to commercial reality? 16
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Assuming the polymer makes a normal peacetime growth, it's not slated to make a commercial debut until at least 1960. But a world rubber crisis would move things along at a faster pace. Isoprene, the needed monomer, could be had in 90 days. The rubber industry has solved m a n y technical problems related to polyisoprene and can offer a product to the market should there be a demand. Goodyear says it's suitable today if used on a 50-50 basis with natural rubber. Firestone says simply that polyisoprene is ready for commercial use and Goodrich-Gulf explains its process can b e frozen tomor-
row if immediate construction were necessary. Missing, then, are th^ plants to make synthetic natural r u b b e r in volume. And it might take one to two years to build such plants. Now, only E n jay makes commercial isoprene, and that by steam cracking higher hydrocarbons from refinery streams. Several t h o u s a n d tons a year are made, but Enjay uses most of it as a c o m o n o m e r with isobutylene to make butyl rubber. T h e supply is inadeq u a t e , the xorice too high, and the purity too low for polyisoprene. W h a t the r u b b e r industry will n e e d is isoprene in 97 rA ptirity or better—the so-called polymerization grade. Phillips Petroleum makes 9 9 ' r isoprene from the monomer it gets from Enjay and sells it for research and d e v e l o p m e n t on synthetic natural r u b b e r . This is the isoprene supply picture today. But the potential is vast for a n e w a n d large industry. Enjay says it could offer polymerization g r a d e isoprene in v o l u m e in 90 days, in fact has some available for sale now. Phillips plans to continue as an isoprene supplier. And m a n y others in the chemical, petroleum, and rubber industries have looked over the pro's a n d con's of making isoprene. Likely prospects: butadiene producers, w h o h a v e about 1.08 million short tons of annual capacity in the U. S.-about 300,000 tons more than u s e d now. Hon dry Process says its dehydrogenation process used to make b u t a d i e n e can also be used to make isoprene using an isopentane or p e n t e n e feed. And, the company points out, firms with its process could go ahead with isoprene production, should they desire, under existing rights p u r c h a s e d earlier. There is no need to re-negotiate contracts. Should isoprene be needed, then, it a p p a r e n t l y can be p r o d u c e d with existing facilities. It's u p to the r u b b e r companies to decide when the monomer is n e e d e d a n d i n what volume. Quite likely, they will want isoprene at about 15 to 20 cents a p o u n d , and to do this means at least a 25,000 to 30,000 ton-ayear isoprene plant. Butadiene-type processes, however, are not t h e only routes to isoprene. In fact, s o m e 25 different routes are known and six of t h e m look attractive on p a p e r : Starting points are isobutylene, isopentene, acetone, methanol, formald e h y d e , and acetylene. These routes are developmental prospects today, and some rubber industry people feel studies a r e not moving fast enough at
present. B u t t h e r e is much research work o n isoprene, and it is pro"bably too early to firm u p a route t o t h e m o n o mer. Suffice it to say t h a t today some p e o p l e feel t h e r u b b e r industry will h a v e n o s u p p l y problems should it issue a d e m a n d for polymerization g r a d e isoprene. • P o l y i s o p r e n e Situation. Almost everyone c o n c e r n e d with synthetic rubbers h a s done some lab w o r k on polyisoprene. Phillips, Shell, Firestone, Goodrich-Gulf, and Goodyear have synthesized it, but only t h e last three companies h a v e gone to t h e pilot plant stage. Their programs are very active and not d e n t e d in the least b y t h e c u r r e n t business recession. Firestone named its poly isoprene Coral, Goodrich p i c k e d Ameripol S N , and Goodyear likes Natsyn. Goodyear h a s gone so far a s to say it plans to start engineering a n d building a full scale production plant before the end of 1958, with an operational target date in late 1960. This plant would have a 2 5 , 0 0 0 to 30,000 t o n capacity per year. Today, the industry's capacity is entirely pilot plants, and t h e y are large enough t o e n a b l e the rubber companies to design full scale units from them. All o u t p u t today is geared for testing purposes; therefore it's tough to figure out how m u c h t h e industry will m a k e this year, since pilot plant o u t p u t could vary from as little as 50 p o u n d s to as much as 1 ton a day. None is sold commercially, so there's no list price. F o r poly isoprene to b e c o m e commercial it would h a v e to be priced t o compete with n a t u r a l rubber, w h i c h goes today for around 24 cents a p o u n d , subject to price variations up and down from year to year. Synthetic natural would s u p p l e m e n t natural r u b b e r a n d would have the same general use as natural, with heavy d u t y tires holding the most promise today. T h e big thing holding polyisoprene back today is the economic u n c e r t a i n t y . Predictions call for a r u b b e r shortage by .1965. N a t u r a l rubber production cannot b y t h a t time e x c e e d 2 million long tons a year—just a b o u t its present level. S h o u l d the shortage develop as expec!"·!, polyisoprene markets would start to o p e n in the early 1960's. A world upheaval, though, could change the natural rubber p i c t u r e overnight and m i g h t p r o p e l polyisoprene into a dynamic growth similar to the growth of SBR ( G R - S ) during World W a r II.
Patents May Come Easier Patents on d r u g intermediates may be easier to get if a decision by the U. S. Court of Customs and Patents Appeals becomes final. Involved in the case a r e Ciba and a group of C-19,14hydroxy androstenes that Ciba wants p a t e n t e d as steroid intermediates. T h e Patent Office refuses a patent on the chemicals on the grounds that claims were "lacking in utility." But, says t h e court in effect: T h e fact that these chemicals can b e used as intermediates to produce potentially valuable e n d products—in this case steroids that may be pharmaceutically valuable—is proof enough of t h e usefulness of the compounds. T h e Patent Office has asked for an extension of time in which to file for a rehearing or reconsideration. It takes the position that intermediates per s e aren't patentable, t h a t the end product made from these intermediates must b e shown to b e useful before a p a t e n t can be issued. Within the d r u g industry the ruling is hailed as a "landmark in the law." Until now, the discoverer of n e w intermediates sometimes spent years testing end products for proof of pharmacological activity in order to patent the intermediates. Often, in the interval, other companies have come up with the same chemicals and so clouded any patent position o n the intermediates. Industry n o w sees quicker protection available on such chemicals. • The Court A r g u e s . Actually, t h e court points out, t h e r e are two points of law involved: First, an invention, to b e p a t e n t a b l e , must b e "useful." On this point the court sees no argument, since the chemicals seem to be useful for m a k i n g steroids. Second, the law requires the patent application to state clearly how to " m a k e , construct, or use" the invention. Ciba's statement t h a t the intermediates can b e used to make steroids chemically resembling pharmacologically active compounds, along with an outline o n how to m a k e steroids from these intermediates, satisfies this requirement of the law, says the court. Sharply different interpretations triggered the Patent Commission's rejection of Ciba's application, and a lengthy dissenting opinion from one of the court judges. The argument here: To b e patentable, an intermediate must be capable of b e i n g used to m a k e something for which a good use can be pinpointed. It isn't enough that the e n d
product m a y possibly b e valuable somed a y or h a s value in research. "Mere possibility of utility" isn't enough. E v e r y chemical has a possibility of becoming useful eventually, say the dissenting opinion; to allow patents on all of them would start a rush to the Pate n t Office. This opinion, too, terms the majority ruling an invitation to "go ahead and experiment," in the h o p e that success m a y some day come, although there's n o guarantee of finding an active steroid. Further, says the dissenting j u d g e , in cases involving complex chemicals and involved scientific points, it has been the practice of the court in t h e past to go along with the scientific experts of the P a t e n t Office, except w h e r e errors on the part of these, experts c a n be clearly shown. T h e dissenting opinion declares no such errors h a v e b e e n found. • M o r e P r o b l e m s . Even if the court decision stands, more problems are at h a n d . Upjohn already has a patent on s o m e of these chemicals by virtue of claims t h a t are somewhat different from Ciba's. But Upjohn's application was filed after Ciba's, so Ciba's becoming eligible for a patent on these chemicals, too, sets up an interference situation.
Freeport Sells Oil Interests Freeport Sulphur this month is completing arrangements to sell its oil a n d gas interests at L a k e Washington, L a . T h e buyer—for $100 million in cash—is Magnolia Petroleum, southwest affiliate of Socony Mobil. Magnolia will put up part of the money and finance the rest against future production. Freeport expects to add $73.7 million to its coffers after paying taxes connected with the transaction. W h a t lies behind the sale? Essentially, it will h e l p pay for growth. F r e e p o r t president L a n g b o u r n e M. Williams puts it this way: "Freeport and its subsidiaries h a v e under way a major program of expansion and diversification, not only in sulfur b u t also in nickel and cobalt. While the financing of these projects has been arranged, the financial resources of the company have as a result been to a large extent committed. "The sale of our Lake Washington oil and gas properties, therefore, not only will enable us to pursue vigorously our activities in all these fields b u t will p u t us once again in an excellent position to take advantage of opportunities for future growth." JULY
2 8.
1958
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