annual review
ROBERT KUNIN
Ion Exchange Advances in ion exchange technology during the past year are assessed in the context of seventeen years of progress.
New ion
exchange materials reported in the literature are presented and evaluated for both organic and inorganic industrial applications he first review of ion exchange T [IND.ENG.CHEM. (I), 41-5 (1948) ] covered the progress immedi40
ately following World War 11. T h e ion exchange resins based upon styrene and the acrylics were still primarily in the laboratory stage and most industrial applications involving ion exchange were based upon the siliceous and phenolic ion exchangers. For example, the sulfonated styrene-divinylbenzene cation exchange resins had just become available commercially. T h e weak acid acrylic cation exchange resins and the strong base quaternary ammonium anion exchange resins were essentially unknown to the field. T h e appearance of these new ion exchange resins, which closely followed the first Annual Review, resulted in many important developments in the fields of water treatment, hydrometallurgy, atomic energy, and chemical and pharmaceutical processing. One cannot overemphasize the importance of these ion exchange resins to the widespread use of supercritical boilers in electric power generation; the recovery of uranium from low grade ores ; the commercial development of atomic power; the recovery and purification of streptomycin, neomycin, vitamin B-12, and other pharmaceuticals ; the availability of
ultrapure rare earths and other space age metals; the widespread use of high purity liquid sugars; desalination of brackish waters; arialytical chemistry; and catalysis. Although it would be presumptuous of this reviewer to infer that ion exchange was the single key factor in successes achieved in these areas, it is generally conceded that ion exchange has been of major importance in each of these areas. A review of the literature and events during the past year reveals that ion exchange maintains its important role in each of the abovecited areas of utility and that various efforts are in progress to improve the position of ion exchange. For example, progress is being made in terms of improving the efficiencies and stabilities of ion exchange resins. New macroreticular ion exchange resins have been developed and unique areas of utility have been uncovered for them. Improved techniques and apparatus are being developed. Ion exchange continues to make progress in the refining of sugar and interest has been renewed in the use of ion exchange for the treatment of brackish waters and sewage effluents. A brief glance at the references cited in this review reveals the intense ion exchange activity in the U.S.S.R.,
Czechoslovakia, munist nations.
and
other
Com-
Reviews
Watts (5A) has written a n extensive review a n current ion exchange practices including a discussion of new ion exchange materials, techniques, and problems encountered in the field. A similar review has been made by Mikes ( 3 A ) . Tremillon ( 4 4 has reviewed some of the more important principles involved in the use of ion exchange. A Russian book describing the properties of ion exchange materials has been written by Chmutov ( 2 A ) , a Soviet authority in the field. Of particular interest is the monograph by AmphIett ( I A ) on inorganic exchangers, a n area of renewed interest. It is indeed unfortunate, however, that much of the recent work in this area has ignored the extensive work of Sante Mattson and his students who published extensively in the United States and Sweden from 1926 to
1946. Theory
Numerous studies are in progress in which attempts are being made to quantitatively account for the selectivity of ion exchange substances, particularly with respect to changes in the physical and chemical structure of the exchanger. Extensive thermodynamic studies were conducted by Boyd et al. (4B) and by Soldatov and Starobinets (26B-29B) on the sulfonated styrene-divinylbenzene cation exchangers of varying degrees of cross-linkage. Other selectivity investigations on similar cation
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exchange resins have been conducted by Klein et al. (17B), Strelow et al. (30B). and Whitney and Diamond (32B). A detailed stud>-of the p K and se1ectivit)- of an iminodiacetic acid chelating exchanger was reported by Leyden and Underwood (79B). Employing spectrophotometric techniques, Boyd et al. (3B) concluded that under special circumstances these ion exchange resins may extract salts by essentially a solvent extraction mechanism involving ion association complexes. Various studies on ion exchange in nonaqueous media with particular emphasis on the role of hydration and dielectric constant were described by Davies and Narebska ( 8 B ) , Davydov et al. (9B), Dickel and B u n d (IOB),Gupta (74B),Poitrenaud ( 2 I B ) ,and Savitskaya et al. (23B). A series of three related studies on the ion exchange properties of synthetic zirconium phosphates were reported by Ahrland and Albertsson (7B), Amphlett and Jones ( Z B ) , and Harkin et al. (I6B). Gustafson (75B) has made a detailed study of the hydrogen ion equilibrium for a cross-linked polymethacrylic acid copolymer in KaCl solutions. Freeman et al. ( I I B ) have presented a detailed study of the electrolyte uptake equilibria in low cross-linked cation and anion exchange resins. The gas phase adsorption of iodine by anion exchange resins was studied by Giona (12B), who found the resins able to vary xvith the particle size and the nature of exchangeable anions. Detailed physical studies on the pore structures of macroreticular or macroporous ion exchange resins were presented by K u n and Kunin (78B) and Millar et al. (2L)B). Diffusion controlled kinetics in ion exchange resins were reported by Bychkov et al. (5B),Golubev and Panchenkov ( I 3 E ) , and Smith and Dranoff (25B). The kinetics of ion exchange in a n iminodiacetic acid chelating ion exchange resin was found by Schwarz et al. (24B) and Varon and Rieman (31B) to be diffusion controlled. The columnar characteristics of ion exchange relating the concentration history with diameter, height. and flow rate were studied in detail by Chuprina ( 6 B ) , Cooney and Lightfoot (7B), and Rosset et al. (22B). 110
Water Conditioning
I n the area of water softening by means of ion exchange, no significant publications appeared during the past year ; however, unpublished reports reveal that there has been considerable interest in the use of sulfonic acid cation exchange resins for the softening of brackish waters used for the generation of steam required in the secondary recovery of oil in the oil fields. With respect to the deionization of water by ion exchange resins, a number of interesting developments are noteworthy. The use of polishing, regeneratable, mixed bed deionization units for preparing the high quality water required by the electronics industry has been described by Lorch (7C) and Rees et al. ( I Z C ) . T h e treatment of the steam condensate used in high pressure steam plants with a powdered ion exchange resin mixed bed filter has been reviewed in detail by Stafforini ( I S C ) . The powdered ion exchange filter serves to remove the traces of soluble electrolyte and colloida1 iron, copper, and silica. T h e use of deionization for treating the water circuits of nuclear reactors has bcen described in detail by Winkler and Schoenherr (78C)and Ganzha et al. (4C). Some problems encountered in Russia on the regeneration of the anion exchange resins used in deionization systems have been discussed by Prokhorova (7OC) and Smirnov et al. (74C). The advantages of using macroreticular anion exchangers for the treatment of surface waters have been cited by Wolniewicz ( I C ) . There has been renewed interest in the use of ion exchange for the deionization or desalination of brackish waters. TVhereas this technique is not normally considered for waters ~~
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AUTHOR Robert Kuni n is Research Associate, Research Laboratories, R ohm @ H a a s Co., and a leading authority on ion exchange as well as on several areas of polymer chemistry. H e has authored I g E C ’ s annual reviews of ion exchange for the past 77 years. T h i s review covers the pertinent literature published during the period f r o m M a y 7964 through M a y 7965. T h e author gratefulb acknowledges the assistance of D r . Erich Meitzner, M r s . Janice Brock, and the library s t a f of Rohm C3 H a a s Co. i n the preparation of this review.
INDUSTRIAL A N D E N G I N E E R I N G CHENiISTRY
having a total dissolved solids content above 500 p.p.m.. this is not really a technical limitation. Contrary to prevalent misconceptions, this degree of salinity is not even an economic limitation in many situations. Ion exchange has been used to treat waters containing more than 2000 p.p.m. of dissolwxl solids, and the availability of several new ion exchange resins and new techniques has made ion exchange most attractive. I n view of the extreme flexibility of ion exchange, deioiiization by ion exchange resins is competitive with other techniques for the desalinization of brackish waters. Kuiiin and \’assiliou (6C) describe an ion exchange process for the treatment of brackish waters using weak electrolyte ion exchange resins. Ion exchange processes for the treatment of various waste effluents containing organic compounds such as 2,4-D, phenols, and amino acids have been studied by Aly and Faust (IC),Mehls (8C),Xarasaki et al. (9C).Rashkevich and Korchagin (71C),apd Stuchlik (17C). A study of the use of ion exchange for the removal of radioactivity from water was reported by Smal et al. ( I 3 C ) . Kunin and Preuss (5C)describe the use of a boron specific ion exchange resin for the removal ol objectionable traces of boron from water. A Russian stud) (3C) 011 resins used for the deionization of Jvater indicates that such treated water can be safely used for drinking purposes. .4 report by Baldwin (2C) describes a unique design for a fixed bed ion exchange unit in which the ion exchange resin is contained in an elastic envelope which can be dilatcd hydraulically to prevent channeling due to the expansion and contraction of the bed. Spinner and Hunter (ISC)describe a new semicontinuous method of operating a fixed bed utilizing a reciprocatins flow in alternating directions. Inorganic Chemistry land Hydrometallurgy
T h e ion exchange recovery of metals by adsorption and elution of various metals and metal complexes was studied by investigators throughout the world. .This includes studies by Mikhanosha et al. (6D) on chromium; Gavril’chenko et al. ( 2 0 ) on silver: Dadabaev (ID)on thal-
lium; Pie et al. ( 7 0 ) , Lloyd (50), and Gel’man et al. (30) on the radioactive transuranic elements. Other ion exchange hydrometallurgical processes reported include those of Yurkevich and Sviridovskaya ( I I D ) on tungsten, Tedesco and deRumi (700) on vanadium, and Plaksin (80) on platinum, iridium, gold, and the rare earths, An ion exchange process for converting COZ, SOZ, and phosphoric acid to their respective salts was described by Kunin (40). A review of various inorganic ion exchange separations in nonaqueous and mixed organic-aqueous solvents was reported by Prasilova (90).
V ERSAT ILlTY IN AN EXTRACTION COLUMN 8
Organic Chemistry and Biochemistry
Ion exchange techniques continue to be developed for various purposes in the fields of organic chemistry and biochemistry. Wymore (12E) has found dry ion exchange resins to be excellent and regeneratable desiccants for various solvents. Danilko et al. (3E) have employed ion exchange for the purification of rectified ethyl alcohol. Ol’shanova and Frolova (8E) have deacidified oils with anion exchange resins. Bors et al. ( I E ) have isolated various alkaloids with ion exchange resins. T h e ion exchange recovery and purification of glutamic acid from fermentation broths have been described by Tanaka and Aoki (IOE), Karklins and Ramina (5E), and Fujiyama (4E). Ion exchange processes for recovering and purifying antibiotics, vitamins, and enzymes were described by Trakhtenberg and K a n (77E), Kunin (6E), Chaiet (2E), Nakanishi (7E), and Sankyo Co., Ltd. (9E).
Designed for counter current and fractional liquid extraction, Chem Flow’s new Karr Column provides far greater efficiency with a smaller total column. Special design features enable the user to vary the degree of agitation by an integral speed control (30 to 510 strokes per minute), by amplitude variation (0 to 1%’’ stroke), and by a simple internal plate arrangement. The speed control is continuous and adjustable over the entire range while the column is in operation, Of particular interest is a feature that is unique to the Chem Flow Karr Column -varying degrees of agitation can be had in different sections of the column at the same time. This is accomplished by simple and quick internal adjustment of the plate spacing. Perfect correlation exists between pilot/laboratory use and production operation. Process scaleup can be done directly from laboratory data.
Food Technology
According to the Federal Register
(4F-6F),various ion exchange resins are listed as being acceptable under the Federal Food, Drug, and Cosmetic Act for use in the treatment of food if they are first subjected to prescribed preuse treatment and if the exchangers pass certain tests. McGarvey (7F) has prepared a detailed evaluation of a multiple bed ion exchange resin deionization process for the treatment of beet sugar juices and sirups. Anion exchange resin sugar decolorization studies have been described by Schneider (8F) and Chikin et al.
KARR RECIPROCATING PLATE EXTRACTION C O L U M N
Visit our Booth No. 3707 at the Exposition of Chemical Industries, New York Coliseum, Nov. 29 to Dec. 3.
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development of inorganic exchangers capable of being utilized at high temperatures. Zirconium phosphate gel appears to be the most popular inorganic exchanger from a research point of view. Details of its preparation have been described by Ahrland et al. ( I J ) , Materova and Skabichevskii ( 7 7 4 , and Clearfield and Stynes ( 4 J ) . Other inorganic exchangers based upon such materials as stannic phosphate, ferrocyanides, Catalysis and molybdates were described by Several recent studies on use of Inoue (U),Huys and Baetsle (7J), sulfonic acid cation exchange resins and Kourim et al. ( 7 7 J ) . as catalysts include those of AnSeidl and his associates (201, ZIJ) drianova (IG) on vapor phase esterihave reviewed the newer trends and fication; Tsvetkov (5G) on the approaches to the synthesis of ion alkylation of phenols ; Isagulyants exchange resins and have described and Safarov (3G) on the condensasome of the principles involved in tion of unsaturated hydrocarbons the preparation of macroreticular with carbonyl compounds ; Ghatge structures. Hopff et al. ( 6 J ) have (2G) on the preparation of polydescribed the details of the susesters; and Maros and Vanscopension-polymerization techniques. Szmerczanyi (4G) on the polyKokoshko et al. ( 7 0 4 have detailed condensation of maleic anhydride the synthesis of several n e ~ 7monwith various glycols. omers useful for the preparation of anion exchange resins. Several Membranes noteworthy studies on the st) reneVarious studies have been directed divinylbenzene sysrem have been made by Storey (23J) and IYiley toward the improvement of memr braqe electrodialytic processes, parand his associates (26J,27J). ticularly for the treatment of brackAnderson (2J) has prepared a ish water. Included are the memvery interesting contour map of the brane synthesis studies of Worsely anion exchange properties of the et al. ( 7 8 H ) ) Tombalakina et al. quaternary ammonium anion ex( 7 6 H ) , Tevlina and Kotlyarova change resins based upon chloromethylated and aminated styrene(15H), Sigodina et al. (7323)) Oda divinylbenzene copolymers. Several ( I I H ) , and Hodgdon and Boyack (5H).Fundamental studies on the other anion exchange resin syntheses diffusion and transport properties of have been described by Lloyd and ion exchange membranes were reDurocher (14J), Hatch and Lloyd ported by Suryanarayana and Joshi (5J), and Skondak and Nikolaev ( 7 4 H ) , Sen0 and Yamabe (12H), (22J). Rabek and Morawiec (79J) have synthesized a cation exchange Gregor and Peterson ( 3 H ) , Mandersloot ( 7 H ) , Oda and his associates resin based upon the sulfonation of (9H,IOH, 17H), Danilkin et al. a polybenzyl polymer. Ion exchange resins based upon phos( Z H ) , and Laeuger and Kuhn ( 6 H ) . The operation of an ion exchange phorous and arsenic functionality electrodialysis plant treating the have been described by Marhol entire water supply of Buckeye, ( 7 6 3 ) and Tevlina et al. (24J). Considerable effort is still being Ariz., was reviewed by Hammer ( 4 H ) . Various developments in the directed toward the development of use of ion exchange membranes in specific and chelating ion exchange fuel cells were reviewed by Berger structures. Veruovic (25J)has de(IH) and Matsuda et al. (8H). scribed the preparation of a condensed flavone having a high selecN e w Ion Exchange Materials tivity for ferric ions. Lewandowski and Szczepaniak (13.7) have preI n the development of new ion pared a noble metal-selective exexchange materials, much of the changer based upon a rhodanine effort has been directed toward structure. Selective exchangers the improvement of physical and based upon resorcinol and arsenic chemical stability, the synthesis of specific ion exchangers, and the acid have been described by Las(IF). A cation exchange resin (hydrogen cycle) process for the treatment of grape juice prior to fermentation for wine production has been studied by duPleiss ( 2 F ) . A cation exchange process for the removal of radioactive strontium from whole milk has been developed by the U. S. Department of Agriculture and described by Easterly et al. ( 3 F ) .
112
INDUSTRIAL A N D E N G I N E E R I N G CHEMISTRY
tovski et al. (72J). Chelating exchangers based upon 4-acetoxystyrene and divinylbenzene have been described by Packham ( 78J). Various redox polymers have been synthesized by Baistrocchi and Grossi ( 3 4 and Manecke and Storck (75J). A review of redox resins has been prepared by Kadlec and Brodsky (9J). Testing Methods
Committee D-19 of the American Society For Testing Materials (ASTM) has two active task groups studying the establishment of standard methods for evaluating various ion exchange materials. The work of these groups is beginning to bear fruit and their efforts should be most valuable to all those interested in ion exchange. Verteshev and Komarovskii ( 4 K ) have developed an experimental apparatus for hydraulically grading ion exchange resins. Nuclear magnetic resonance methods for studying ion exchange resins have been described by deVilliers and Parrish ( I K ) and Dinius and Choppin (ZK). A dilatometer useful for ion exchange studies has been developed by John Thompson, Ltd. (3K). The thermal stability of ion exchange resins has been studied by Erofeev et al. (7L) and Skorokhod et al. (3L). The radiation stability of anion exchange resins has been studied by Kiseleva et al. (2L). Two recent reviews on the characteristics and applications of liquid ion exchangers were prepared by Haeupke and Itrolf ( 4 M ) and Green (3M). Several studies on the extraction of metal complexes by liquid anion exchangers were presented by Arai et al. ( 7 M ) on vanadium, by Davidson and Jameson ( Z M ) on the platinum group, by Jenkins and Wain (5M)on molybdenum, and by Zangen (tTAM)on the trans-plutonium elements. REFERENCES Reviews
(1A) Amphlett, C. B., “Inorganic Ion Exchangers,” Elsevier, New York, 1964. (2A) Chmutov, K. V., “Investig-ation of the Properties of Ion-Exchange Materials“ (Russia), Xauka, Moscow, 1964. (3A) Mikes, J., .bfu,g. Kern. Lafija 19 (61, 303 (1964). (4.4) Tremillon, B., Bull. I n , f ~ m . Sci. Tech. (Paris) 50 (8j), 5 (1964). (SA) Watts, A . B.? Chem. Proc. Eng. 45, 4 (1961). Theory
(1B) Ahrland, S., Albertsion, J., Acta Chern. Scand. 18, 1861 (1964).
(2B) Amphlett, C. B., Jones, P. J.: J . Inorg. iVucl. Chem. 26, 1759 (1964).
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(3B) Boyd, G. E.,Lindenbaum, S., Larson, Q. V., Innrg. Chem. 3, 1437 (1964). (4B) Boyd, G. E Vaslow, F., Lindenbaum, S., J . Phys. Chem. 68, z90 (1964). (5B) Bychkov, N. V. Znamenskii, Yu. P., Kasperovich A. I. Isslei. Suoistu Ionoobmen. Materialou, Aka;. Nairk &SR, Inst. Fir. Khim.1964, p. 30. (6B) Chuprina, L. F., Irv. V sshikh Uchebn. Zauedenii, Tekhnol. Legkoi Prom. 1964 p. 20. (7B) Gooney, D . O., Lightfoot, E. N., IND.ENG. CHEM. FUND.4, 233 (1965). (8B) Davies, C. W., Narebska, A,, J . Chem. Sot. 1964.,. D. 4169. (9B) Dabydov A. T Skoblionok, R . F., Lisovina, G. M., Isslid. Sao& Ionoobmen. Materialov, Akad. Nauk SSSR, Inst. Fir. Khim., 1964, p. 79. (10B) Dickel, G. Bunzl, K., Makromol. Chem. 79, 54 (1964). (11B) Freeman D. H . Patel V. C.,Buchanan, T. M., J . Phys. Chem: 69, 1477 (1465). (12B) Giona, A. R., Brit. Chem. Eng. 10, 8 2 (1965). (13B) Golubev V. S., Panchenkov, G. M., Zh. Fiz. Khim. 38’, 1010 (1964). (14B) Gupta, A. R., J . Phys. Chem. 69, 341 (1965). (15B) Gustafson, R. L., Ibid., 68, 1563 (1964). (16B) Harkin, J. P., Nancollas, G. H., Paterson, R., J . Inorg. h‘ucl. Chem. 26, 305 (1964). (17B) Klein, G. Villena-Blanco, M., Vel meulen, T., IND, ENG. &EM. PROCESSDESIGNDEVELOP.3, 280 (1964). (IXB’I Kun, K. A,, Kunin, R., J . Polymer Sci. B2, ‘-Sa? (1964). (19B) Leyden D. E.. Underhood, A . L., J . Phys Cham. 68, 2693 (1964). (20B) Millar, J. R., Smith D. G., Marr, W. E., Kressman, T. R . E,, J . Chim. SOc. 1964, p. 2740. (21B) Poitrenaud, C., Bull. Inform. Sci. Tech. (Paris) 1964 (85), 25 (1964). (22B) Rosset, R., Tremillon, B., Fould, H., Ibid., p. 101. (23B) Savitskaya, E. M., Lou, C. H., Bruns, B. P., Ionoobmen. Sorbenty u Prom,, Akad. iVnuk SSSR, Inst. Fiz.-Khim, 1963, p. 11. (24’5) Schwarz, A,, Marinsky, J. A,, Spiegler, K . S.> J . Phqs, Chem. 6 8 , 918 (1964). (25B) Smith, T. G., Dranoff, J. S., IND.EKC. CHEDL. FUNDAMENTALS 3,195 (1964). (26B). Soldatov, V. S., Starobinets, G. L., Issled. Suoistv Ionoobmen. Materialov, Akad. hrauk SSSR, Inst. Fiz. Khim. 1964, p. 36. (27B) Soldatov, V. S., Starobinets, G. L., Zh. Fir. Khim.38, 6 8 1 (1964). (28B) Starobinets, G. L., Novitskaya, L. V., Kolloidn. Zh. 26, 105 (1964). (29B) Starobinets, G. L., Soldatov, V. S., Zk. Fir. Khim. 38, 992 (1964). (30B) Stielow F. W., Rethemeyer, R., Bothma, C . J. C., Ani?. Chem. 37,106 (1965). (31B) Varon, A,, Rieman, W., 111, J . Phys. Chem. 68, 2716 (1964). (32B) Whitnev D. C., Diamond, R . M., J . Inorg. Nucl. Chem. Z?, 219 (1965). ~
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0
h),
Water Conditioning (1C) Aly, 0. M . , Faust, S. D., J . Am. Water Works Assoc. 57, 221 (1965). Tribune CEBEDEAU (Center (2C) Baldwin P Belge Etude bot. ~ U X 17, ) 248 (1964). (3C) Chumburidze B. I,, Saldadze, K . M., Issled. Suoistu Ionoobmen,’ Materialov, Akad. Nauk SSSR, Inst. Fiz. Khim, 1964, p. 173. (4C) Ganzha V. D., Konoplev, K. A,, Trenin. V. D.. Shirov, V. T . , At. Energ. (USSR) 16, 456 (1964). (5C) Kunin, R . Preuss, A. F., IND. EKG. CHEhi. PROD.RES.D E ~ E L D3,304 P. (1964). (6C) Kunin R., Vassiliou, B., IKD. END. CHEM. PROCESS DESIONDEVELOP. 3, 404 (1964). (7C) Lorch, W. F., Chem. Proc. Eng. 45, 20 (1964). (8C) Mehls, K . F. H., Dechema Monograjh. 52, 895
(i965). (9C) Narasaki, H . , Ito, N., Kanayama, T., Sakurai, S., Tokyo Kogyo Shikensho Hokuku 59, 464 (1964). (1OC) Prokhorova, A. M., Teploenergetika 11, 70 (1 964). (11C) Rashkevich, I. I., Korchagin, L. V., Koks i Khim. 1965, p. 40. (12C) Rees, E., Halff, A,, Reid, A,, McCormack, A., J.A.W.W.A. 56, 301 (1964). (13C) Smal Z Bulanda, J., Horski, J., Siemaszko, A,, Nuklednika‘9, 733 (1964). (14C) Smirnov A. S., Peremyslova, E. S., l\.liropol’skii, M. U., ’Talalaeva, A. V., Plasticheskie Massy 1964, p. 33. (15C) Spinner, I. H., Hunter, R. F., Can. J . Chem. E n .p, . 42., 28 (1964). . (16C) Stafforini, P., Termotecnica (Milan) 18, 376 (1964). (17C) Stuchlik, H., Fenolove Odpadni Vody 1962, p. 77. (18C) Winkler, R., Schoenherr, A,, Kernenergie 7, 741 (1964). (l9C) Wolniewicz, E,, Z. Texlil. Ind. 66, 746 (1964).
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Inorganic Chemistry & Hydrometallurgy (1D) Dadabaev, A. Yu. Milusheva M. A. Sushchenko S. N Tr. Z&t. Met. i dbogashch.: Akad. Nhuk k a z . SSR11, 129 (1964). (2D) Gavril’chenko A . I., Dranitskaya, R. ?d., Vasserman., L. I,.’Ukr. Khim. Z h . 30. 1113 (1964). , (3D) Gel’man, A. D., Mefod’eva, M. P., Kiseleva, E D. Glazunov M. P., Kodochigov, P. N., PeretrLkhin, V. F.: Radiokhzmiya 6 , 35 (1964). (4D) Kunin, R., IND.ENG. CHEY.56, 35 (1964). (5D) Lloyd, M. H., Nuclear Sci. Eng. 17, 452 (1963). (6D) Mikhanosha, E. S., Yudin, A. V., Barboi, V. M., Im. Vysshtkh Uchebn. Zauedenii, Tekhnol. Legkoi Prom. 1964 p. 97. (7D) Pie VV. L., Joy-ce, A. I$’., Martens, R. 1.8 IND. ~ N G . CHEY. PROCESS DESIGNDEVELOP.39 314 (1964). (8D) Plaksin, I. N., Izu. Akad. Xuuk SSSR, Met. i Gorn. Delo 1964. D. 32. (9D) Prasilova, J., Chem. Listy 58, 401 (1964). (10D) Tedesco, P. H., deRumi, V. A.M. B., AJinidad 21, 106 (1964). (11D) Yurkerich, Yu. N., Sviridovskaya, R. M., Sb. Tr. Vses. Nauchn. Issled. Inst. Tverd. Splavou 1964, p. 245. I
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Organic a n d Biochemistry (1E) Bors, G., Ionescu, I., Ioanid, N., Furmacia 12, 479 (1964). (2E) Chaiet, L., U. S. Patent 3,163,637 (Dec. 29, 1964). (3E) Danilko, G. V., Egorov A. S. Danilyak, N. I., Kaminskii, R. S., Fermen/na>a i’ Spirt. Prom. 30, 29 (1964). (4E) Fujiyama, Y . , et al., German Patent 1,169,954 (Aug. 4, 1962). (5E) Karklins, R., Ramina, L., Mikrobiol. Protesessy i PrOiZv., Akad. hratik Latu. SSR, Inst. Mikrobiol. 1964, p. 67. (6E) Kunin, R., U. S. Patent 3,147,245 (Sept. 1, 1964). (7E) Nakanishi, K., et al., U. S. Patent 3,135,667 (June 2, 1964). (8E) Ol’shanova K. M., Frolova, G. V., Rybn. Khoz. 40, 85 (lb64). (9E) Sankvo Co., Ltd., British Patent 937,327 (Sept. 18, 1964). (10E) Tanaka, M., Aoki, Y . , U. S. Patent 3,173,949 (March 16, 1965). (11E) Trakhtenberg, D. M., Kan, A . M., Antibiotiki 10, 38 (1965). (12E) Wymore, C. E,, J . Inorg. Nucl. Chem. 26, 855 (1964). Food Technology (1F) Chikin, G. A,, Meleshko, V. P., Kleiman, hf. B., Polishchuk, F. M., Sakhar. Prom. 38, 105 (1964). (2F) duPleiss, C. S., S. A/rican J . 4 7 . Sci. 7, 3 (1964). (3F) Easteily D. G., Edmondson, L. F., Avants, J. K., Sadldr, A. M., J . Dairy Sci. 47, 549 (1964). (4F) Federal Register 29, 6278 (1964). (5F) Ibid., p. 9708. (6F) ~~,Ibid.. 30. 32 (1965). . (7F) McGarvey, F. X., J . Am. Soc. S q n r Beet Tech. 133 252 (1964). (8F) Schneider, F.; Zuckw 17, 149 (1964). I
I
Catalysis (lG) Andrianova, T. I., Kinetika i Kalaliz 5, 927
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