RESEARCH Step by Step
TILE When you need it, you'll find in Chemical Engineering Catalog pages and pages of tile facts from 22 companies. Consult CEC for data on acidproof brick tile . . . straight or radial chemical lining tile . . . carbon brick . . . corrosion-proof . . . weather-proof . . . fire-proof . . . hollow double-wall blocks. Yes, all this and much more in the pages of
cec
No matter what facts you may need, CEC is placed in process plants to help you find answers to process problems fast. Completely indexed six ways, CEC is your exclusive source of up-to-date facts about equipment, materials of construction, engineering services. Almost 100 pages of indexed materials connect you with the products and services of America's leading manufacturers who place their data in this big 2000-page volume. CEC is bound to serve you best . . . so use it often !
REÎNHOLD Pubushing Corporation 430 Park Avenue
2506
C&EN
MAY
2 1.
1956
First availability of D-erythrose-4-phosphate allows noteworthy biochemical discovery T H E FIRST SYNTHESIS of D-erythrose4-phpsphate was achieved early last year, as might be expected, by Clinton E. Ballou, Hermann O. L. Fischer, and D. L. MacDonald of the department of biochemistry, University of California [JACS 77, 5967 (1955)]. "As might be expected" because that group, led by Fischer, is the only one in the country working extensively on short chain, phosphorylated sugar derivatives, compounds which are extremely unstable and difficult to handle. (D-Erythrose-4-phosphate is stored and transported as the cyclohexylammonium salt of 4-phosphoryl-D-erythrose dimethyl acetal, from which it can be prepared readily when needed.) Such compounds, notably the phosphorylated, three-carbon sugar derivatives, are important intermediates in the Embden-Meyerhof scheme of alcoholic fermentation and glycolysis, in which glucose in human and animal muscle breaks down enzymatically to lactic acid. From this process comes the driving energy of muscular action. Five of these three-carbon intermediates have been synthesized by Ballou in Fischer's laboratory at California; their availability in quantity, and in a pure form, has helped greatly to develop and confirm the Embden-Meyerhof scheme. While the compounds occur naturally in muscles, they are difficult if not impossible to isolate in pure form and in practical amounts from fermentation juices or muscle extracts. The reason: They are extremely sensitive to chemical reagents and are present only in minute quantities at any given moment. • The Second Step. To return to Derythrose-4-phosphate: Just a few months after Fischer's laboratory made the compound available, D. B. Sprinson and his colleagues at Columbia University found that it could be condensed enzymatically with phosphoenolpyruvate to give a 90% yield of dehydroshikimic acid. The latter is a derivative of shikimic acid, a hydroaromatic compound prepared from a Japanese fruit. Both hydroaromatic and aromatic compounds occur widely in nature and have long been believed to be formed from carbohydrates.
Sprinson's work outlines for the first time a clearly defined chemical pathway via which that process can take place. Availability of r>erythrose-4-phosphate has also permitted confirmation of other biochemical reactions. Among them are the enzymatic formation of sedoheptulose, a seven-carbon sugar characteristic of the native avocado, and enzymatic formation of D-ribose, the five-carbon sugar present in many nucleic acid molecules. • Three-Carbon Intermediate. Shordy before the success with rnerythrose-4-phosphate, Ballou and Fischer had synttiesized D-glyceraldehyde-3phosphate [JAC S 77, 3329 (1955)], another important intermediate in glycolysis. Fischer and Erich Baer, at the University of Toronto, had synthesized racemic glyceraldehyde-3-phosphate in 1932. This compound proved to be of great use biochemically, but because of the steric specificity of biological systems, racemic substrates are generally undesirable and can give misleading results. For this reason, D-glyceraldehyde-3-phosphate, prepared enzymatically (from D-fructose-l,6-diphosphate), h a d been used occasionally in preference to the chemically prepared
University of California's H. O. L. Fischer—tris short chain, phosphorylated sugar derivatives permit confirmation of several biochemical reactions
18-Carbon straight-chain amine, 1 0 % , in light fuel oil
Rohm & Haas Primene J M - f , 1 0 % , in light fuel oil
For Highly Soluble Oil AdditivesP R I M E N E Amines Here's evidence of the solubility of PRIMENE amines in petroleum products. A free-flowing liquid, t h e 18-carbon PRIMENE aliphatic amine shown here dissolved readily in oil while a similar straightchain amine proved relatively insoluble. I n fuel oils, the PRIMENE amines also stabilize color, help prevent the formation of sludge, a n d are ash-free. I n motor oils, the PRIMENE amines exhibit excellent solubility a n d resistance to oxidative degradation. O t h e r suggested uses for PRIMENE alkyl amines or their derivatives include bactericides, fungicides, corrosion inhibitors, anti-oxidants, textile chemicals, and pharmaceuticals. Write today for information on t h e PRIMENE a n d other t-alkyl amines. PRIMENE is a trade-mark, Reg. U.S. Pat. Off. and in
ROHM & HAAS ALKYL AMINES PRIMENE 81-R: 12-15 carbon t-alkyl primary amine PRIMENE JM-T: 18-24 carbon t-alkyl primary amine t-Butylamine t-Octy!amine
Chemicals for Industry
ROHM S. HAAS C O M P A N Y WASHINGTON S0UAR2, PHILADELPHIA S, PA. Representatives in principal foreign countries
principal foreign countries MAY
2 1, 1 9 5 6 C & E N
2507
RESEARCH
•Kfe*sftftl-.ld
racemic form. Ballou and. Fischer's chemically prepared D-comp ouncL, however, is optically purre, completely a c tive biologically, anxl eliininates t h e need for the enzrymiatically prepared compound. For this and his earlier work o n t h e synthesis of carbohydrates and their derivatives, fermentation intermediates, and inositols [C&EN, page 207O (1949)], Fischer h a s received t h e Gold Adolph von Baeyer Medal of t h e Society of German Clierriists. The award was appropriate not only i n t h e scientific sense, but a~lso in a more personal sense, as von Baeyer WSLS t h e teacher of Emil Fischer, father and teacher of the recipient.
BORON goes
eoÉimerciài I
HBHHU
at new down HMNNHMI T O D A Y S ELEMENTAL BORON , S DEFERENT Through research and production progress, amorphous elemental boron is now available in commercial volume at realistic commercial prices. Today's product is a useful commercial chemical, no longer a research curiosity. In the Military, elemental boron is being used in Ordnance applications for flares, fuses, ignitors, and propellant mixtures. Commercially, it is used in boridesfor high temperature applications, and with plastics for lightweight neutron shields. ^ere|never|wa5.ia|b8.tter|time^ lthan|now|ioflooklintolthefpo?f itenjtja Ép^lttieflastestfgrow.ing| ^GhfecMyqûMteqûïrèmënltsmfôi^ lei e me η ta iboro.nfka ndiaslaii
Built-in Durability Chemical treatment gives cotton and other natural fibers improved resistance to mildewing and w&ath&ring JTROTECTION
OF
^STATURAL
3FIBEKS
against t h e ravages of mildew arxd outdoor weathering has long been a. foremost problem of t h e textile industry. A new attack on the problem h a s now been devised b y National Cylinder Gas, working in cooperation witb. t h e Southern Research. Imstitate. Although NCG declines to reveal the exact c h e m i cal nature of its process, it does s a y that it involves an organic copper compound that chemically modifies thie cellulose molecule. Copper compounds have long been used as preservatives o£ cellulose. Copp er naphthenate, Eor example, has been widely em.ployed as a. preservative of canvas, xope 3 a n d w o o d . The n e w treatment, which will b e available t o the textile industry sliortly, is primarily intended for the; treatment of cotton, although it might be used o n linen, rayon, burlap, a n d sisal. It: might also be effective in the treatment of wood, paper, and other cellulosic materials.
When cotton is treated by this method, the copper becomes permanently b o n d e d to t h e cellulose. At the same t i m e , t h e cellulose becomes insoluble i n conventional cellulose solvents such as cuprammonium compounds and cixpriethylenediamine. Futhermore, NCG-treated cotton will not hydrolyze readily even in concentrated hydrochloric acid, which rapidly disintegrates untreated cotton. Because of the permanent bond between the copper and cellulose, special fillers or binders a r e not required to prevent the preservative from being removed by weathering. • Extensive Testing. For the past six years, the N C G process has been studied a t SRI, under the leadership of Edward Abrams, head of the textile section. The process itself was originally devised by Robert R. Bottoms at t h e National Cylinder Gas laboratories i n Crestwood, Ky. N C G says the process is the most effective chemical method available for preservation of cellulose. F o r example, NCG-treated fabric, after seven months of weathering, is reported t o have 2 0 % greater breaking strength than a copper naphthenate treated sample and 3 0 % greater than the untreated fabric. In soil burial tests, untreated fabric completely disintegrates after seven to 14 days while NCG-treated fabric maintains as much as 9 5 % of its breaking strength after 14 weeks of soil burial. The N C G preservative is neither a skin irritant nor a skin sensitizer. Cotton clothing can, therefore, be made completely mildew resistant without hazard t o t h e wearer. Furthermore, t h e compound is odorless a n d does not change t h e feel of the cloth. Although i t imparts a light brown color t o the fabric, this effect can b e minimized by further treatment. The n e w N C G process is expected to b e particularly useful in the treatment of fabrics for tents, sandbags, awnings, convertible tops, and camouflage materials. It might also be of value in military uniforms designed for the tropics.
luLiiiLiLLJ .
;:· / / you want to know mpre.'about elemental boron; contact :'··,..''... ;, -.-.•.Cales.Development Department
ÎÂmmcanJtyasti S Chemcal (Mjwntàm - 3030.W/Sixth St; \39 Park Averiue .'v'rLos Angeles 54 New York 16 ' DLinkirk 2-8231 OXford 7-0544.·; '
2508
C&EN M A Y
2 I,
1956
After one week of b u r i a l hu fertile soil a t 80° F . and 9 5 % relative humidity, mildew attack is evident tbrougjiout the background of untreated cotton duck, while "NTCG," treated w i t h NTational Cylinder Gas' process, is unaffected
