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(196) Teuffert, U. S. Dept. Commerce, OTS Rept., PB 725, Rept. 179 (April 30, 1943). (197) Tietze, Ibid., 14998, FIAT Microfilm Reel C28, Frames 301-13 (April 9, 1937). (198) Timell, T., Svensk Papperstidn., 51, 254-8 (1948). Their Chemistry and Technology,” New York and London, (199) Truce, W. E., and Suter, C. &I., J. Am. Chem. Sac., 70, 3851-2 Interscience Publishers. 1949. (1948). (179) Severoceske Tukove Zavody (Drive Jiri Schicht) Rarodri Pod(200) Tsukervanik, I. P., and Poletaev, A. V., J . Gen. Chem. (U.S.S. nik, Brit. Patent 621,765 (April 19, 1949). R.), 17, 2240-3 (1948). (180) Shilov, E. A., and Kurakin, A. N., J . G a . Chem. (U.S.S.R.), (201) Ufimtsev, V. N., J . Applied Chem. (U.S.S.R.), 20, 1199-208 18, 2092-3 (1948). (1947). (181) Shuck, G. R., and Lingafelter, E. C., J. Am. C h a . Soc., 71, (202) Ibid:,-;283-5 (1947). 1325-7 (1949). (203) Ihid., 1286-7 (1947). (182) Sigwart, U. S. Dept. Commerce, PB Rept. 73911, FIAT Micro(204) Ufimtsev, V. N., J. Gen. Chem. (U.S.S.R.), 18, 1395-8 (1948). film Reel N87, Frames 4610-12 (May 10, 1932). (205) Wacek, A. V., and Kratzl, K., J . Pdgmer Sci., 3, 539-48 (1948). (183) Simon, Ibid., PB Rept. 657, Rept. 240 (March 31, 1942). (206) Weinmayr, V. (to E. I. du Pont de Nemours & Co.), U. S.Pat(184) Sisley, J. P., “Index of Sulfonated Oils and Modern Deterent 2,467,170 (April 12, 1949). gents,” Paris, Teintex, 1949. (207) Weissenborn, U. S. Dept. Commerce, UT$ Rept., PB 70428, Slinger. F. H.. Tatum. W. W.. and Imperial Chemical IndusFIAT Microfilm Reel E25, Frames 8 1 4 3 4 (May 11, 1944). tries, Ltd., Brit. Patent 619,034 (March 2, 1949). (208) Wendland, R. T., and Smith, C. H., Proc. North Dakota Acad. Smith, R. L., Crowley, D. J., and Waldo, P. G. (to SoconySei., 2, 40-3 (1949). Vacuum Oil Co., Inc.), U. S.Patent 2,463,497 (March 1 , (209) Wendland, R. T., Smith, C. E., and Muraca, R., J. Am. Chem. 1949). SOC., 71, 1593-5 (1949). Smyth, G. M. (to American Cyanamid Co.), Ibid., 2,454,679 (210) Wieland, T., Fischer, E., and Moewus, F., Ann., 561, 47-52 (Nov. 23, 1948). (1948). Spaeth, U. S. Dept. Commerce, 02“s Rept. , PB 70345, FIAT (211) Winkelmueller, U. S. Dept. Commerce, PB Rept. 74914, FIAT Microfilm Reel ‘216, Frames 18494-52 (Feb. 15, 1943). Microfilm Reel T31, Frames 4488-90,4511-714 (1936-37). (212) Wintringham, A. C., Moffatt, L. R., and Carland, R. (to AmerSpryskov,A. A.,J. Gen. Chem. (U.S.S.R.), 17, 591-600 (1947). ican Cyanamid Co.), U. 9. Patent 2,479,990 (Aug. 23, 1949). Ihid., 18, 98-102 (1948). (213) Witte, M. (to Allied Chemical & Dye Corp.), Ibid., 2,465,951 Ihzd., pp. 749-52. (March 29, 1949). Ihid., PP. 941-7. (214) Witte, M., and Welge, M., Ibid., 2,465,952 (March 29, 1949). Ibid., pp.1370-5. (215) Yakubovich, A. Y., andzinov’ev, Y. M., J. Gen. Chem. (U.S. Staudinger, H., el al., “FIAT Review of German Science 1939S.R.), 17, 202847 (1947). 1946, Preparative Organic Chemistry,” Part 111, Karl Zieg(216) Yoder, L., and Thomas, B. H., T m . ENG.CHEM.,41, 2286-9 ler, senior author, pp. 67-76, Wiesbaden, Office of Military (1949). Government for Germany Field Information Agencies (217) Yoder, L., and Thomas, B. H., J . Bid. Chem., 178, 363-72 Technical (British, French and U. S. A,), 1948. (1949). Tatum, W. W., and Imperial Chemical Industries, Ltd., Brit. Patent 621,713 (April 14, 1949). RECEIVED June 16, 1050 (177) Schowalter and Lien%acher, U. S. Dept. Commerce, OTS Rept., PB 70345, FIAT Microfilm Reel C16, Frames 1856266 (Feb. 17, 1942). (178) Schwartz, A. M., and Perry, J. W., “Surface Active Agents,
Other Unit Processes HAROLD J. GARBER UNIVERSITY
OF TENNESSEE, K N O X V I L L E , TENN.
T
HE summary presented in this review section deals with advances made in calcination, condensation, desulfurization, and reduction, as represented by the literature published on these topics during the past several years. Inasmuch as the literature dealing with reactions activated by electrical discharges for this period is not sufficiently extensive for inclusion here, reporting on the progress in this field is deferred. Following the pattern established in the previous review, the literature cited is limited to papers that disclose significant information. Papers that merely elucidate minor phases of the four processes discussed are not included in this report.
CALCINATION The literature for the review period discloses relatively few innovations in techniques in this field or in the operation of shaft or rotary kilns. Numerous details concerning some of the newer types of lime kilns and their points of departure from the older types were discussed by Block ( 6 A ) . A paper by Lacy (27.4) also dealt with modern vertical lime kilns, and included a tabulation of the functions of the operating zones, the use of producer gas as a heat source, and the factors that determine the production capacity and thermal requirements. The influence of the method of charging, particularly of undersize feed, on such operating features as production rate, slagging of the refractory, and failure of fans was discussed by Azbe ( S A ) . I n connection with the burning of dolomite in shaft-type kilns, Brumbaugh
( 7 A ) discussed rational methods for kiln design, selection of linings, thermal and material balances, and results of studies of movement of the charge during burning. Khodorov (22.4) reported data for experimental runs made on some automatically operated small shaft furnaces, emphasizing the advantages of low initial investment and operating charges for such units. Formulas, curves, and means for estimating the capacity of rotary kilns were discussed by Gibbs (IbA) and Atherton ( 1 A ) . Means of increasing the capacity of rotary kilns were proposed b y Khodorov (23A, 2 J A ) who made recommendations concerning such items as ratio of kiln diameter t o length, pitch, temperature gradients, and length of sintering zone to obtain maximum capacity. Results of experiments using an oxygen-enriched air blast in the operation of a kerosene-fired kiln to secure higher cement production capacity, among other benefits, were disclosed by Lur’e and Val’berg (MA, 34A). The thermodynamics of lime manufacture was discusaed by Gibbs (14A, 1 5 A ) , who indicated where energy dissipation occurs and presented means to approach perfect kiln operation. Ways to increase the thermal efficiency of rotary cement kilns, primarily by heat recuperation, lengthening the burning zone, reducing the moisture content of the feed, and addition of small amounts of sodium carbonate to the feed were considered by Jaspers ( I 7 A 19A). The influence of recuperator chains, gas velocity, average gas and stock temperature, and final moisture content of t h e product on the experimentally determined heat transfer coeffi-
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cient in the chain zone in rotary kilns was investigated by Khodorov and Diment (26A). Nordberg (S8A) showed how operation of two rotary kilns in series decreased the ratio of coal to cement by 27% with a decrease in over-all capacity of but 19%. Other papers dealt principally with decreasing fuel requirements: Davis ( 8 A ) described a kiln using pulverized fuel claimed to operate more efficiently than eny other existing type; de Junnemann (2OA) discussed the use of chain recuperators, automatic controls, addition of sodium carbonate, and use of blast furnace slag as a means to lower fuel consumption; and Azbe ( 2 A ) pointed out the merits of hot gas recirculatipn. Steps conducive to better performance of continuously operated kilns were discussed. Barnard ( 6 A ) showed how close control o n the flue gases can lead to uniform product, reduced ring formation, and longer lining life. Matouscheck (d7A) pointed out that production rates 2% below that a t which ring formation occurs lead to optimum kiln economy. Gibadlo (12A) cited methods of indirect heating for systems where direct contact between flue gases and product is not allowed. White (&A) revealed a process €or producing nodulized and pelleted products with a minimum of fines. Lellep (28A) disclosed a pretreatment process to prevent cracking and dusting of the feed. Ellerbeck ( 9 A ) patented a kiln for producing high grade lime and carbon dioxide. Azbe ( 4 A ) developed a multizoned countercurrent flow process for treating small stone feeds in a uniform fashion. Martin (%A) revealed details of a countercurrently operated multiple rotating hearth kiln. Geidelman (1OA) discussed methods for producing lime for t h e sugar industry employing low grade coals. Whitney and Hollingsworth (48A) reviewed methods for calcining phosphate rock without sintering the charge. Kite and Roberts ( M A ) described some calcination systems operated under fluidilred conditions. Lenhart (69A) discussed various features of continuously operated lime kilns and (30A) showed how currently plentiful anthracite fines can be used to lower operating costs. Kilns for manufacturing specialized products were discussed. Wassmer ( @ A )patented a kiln with two zones that can be used fo produce either white or gray cement, with economic operation in each case. Vahrub ( @ A ) dealt with the question of kiln design and suitable fuels for calcining magnesite. Lifshits (S1A) and Gezburg ( 1 1 A ) both concluded that calcination of metallurgical dolomite is best carried out with a wet, feed in rotary kilns. Keller ( 2 1 A ) revealed details of an electric arc process for calcining dolomitic rock. A patent granted to Maschinonfabrik Oerlikon (36A)reveals details for a cement kiln that uses both a combustion flame and an electric arc; a similar patent for calcining limestone was granted to Hashimoto and Mochinaga (16A). Phillipp (S9A) listed the operating details of a cement kiln located in Switzerland that is heated by an electric arc. A patent issued to Lonza Electrizitatswerke und chemische Fabriken A.-G. ( W A ) reveals details of a limestone kiln heated by an electric arc in which the gas flow prevents excessive temperature and minimizes nitrogen oxide formation.
CONDENSATION The material reviewed under the general category of condensation is subdivided into small groups, with the interest focused upon one of the general types of compounds being condensed. CONDENSATION OF ESTERS WITH OTHER COMPOUNDS
Royals (83B) studied some condensations of the methyl esters of acetic and propionic acid in the presence of sodium methylate. Croxall and Fegley (I7B)and Croxall and Schneider (18B)investigated the condensation of methyl, ethyl, butyl, 2-ethyl butyl, %thy1 hexyl, and decyl carbonate with acetylene and monosubstituted acetylenes in the presence of sodium methylate and butyrate. Gakhokidze (66B)discussed his &dings concerning
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the condensation of the ethyl esters of formic, acetic, and propionic acid with acetone in the presence of potassium hydroxide. Gakhokidze and Guntsadze investigated the condensation of dimethyl malonate with acetone (66B)and the reaction between ethyl formate and diethyl acetonedicarboxylate (27B), both conducted in the presence of solid potassium hydroxide. Mittal (60B) reported the yields resulting from the condensation of 3,5-dinitro-2-chlorobenzaldehydewith some malonic esters in the presence of such organic bases as pyridine and quinoline. Fuson and Munn (24B)condensed ethyl malonate with 2’-methyl-3’,5’-dinitrochalcone. Harris and Levine (34B) prepared some 2-acetyl furan and acetyl-Pfuroyl methanes as examples of 8-diketones containing a furan nucleus, using sodium amide as the condensing agent. Frostick and Hauser (BSB) prepared some 8-keto esters as ethyl a-propionyl propionate, ethyl a-butyryl butyrate, ethyl a-isobutyryl isobutyrate, ethyl a-isovaleryl isovalerate, and methyl a-lauryl laurate by condensing the appropriate ester with various Grignard reagents in anhydrous ether. Skinner, Anderson, and Bogart (66%) investigated the condensation of a-carbethoxy-a-butyrolactoneswith amidines and guanidine. Harris and Levine (93B) Synthesized acetyl, propionyl, butyryl, caproyl, and benzoyl thenoylmethanes by condensing 2-acetyl thiophene with appropriate esters, using sodium and lithium amides as condensing agents. Hauser, Ringler, Swamer, and Thompson (S6B)described some condensations of phenyl benzoate with methylene ketones as 1-hydrinone and 1-tetralone, using sodium amide as the condensing medium. Gheorghiu and Budeanu (89B) investigated the condensation of benzoyl isothiocyanate with cyclohexanone oxime, methanone oxime, and camphor oxime. Hamell and Levine ( W B )studied the condensation of esters, employing lithium and some substituted lithium amides as the condensing medium. Yost and Hauser (81B)prepared ethyl a,a-diphenylbenzoyl acetate, using potassium amide for the condensing medium. Newman and Magerlein (6SB) reviewed the general field of glycidic ester condensations. Vila’ and Ballester (76B)investigated some condensations of ortho esters with compounds containing aetive methylene groups and showed that in such cases no condensing agents are required. CONDENSATIONS INVOLVING KETONES
Green and LaForge (SOB)studied the use of sodium hydride as a ketone condensing agent. Zellars and Levine (8SB) investigated the action of lithium amide as a condensing medium in the synthesis of @-keto esters and symmetrical B-diketones. Steck and Holland (708) synthesized ethyl a-ethoxalyl valerate, condensing butyl ethyl ketone in the presence of sodium methylate. Mariella and Kvinge ( @ B ) studied the competition between methylene groups in the condensation of unsymmetrical ketones. Munch-Petersen and Hauser (61B)investigated some acetylations of some a-alkoxy and a-aryloxy ketones. MBtayer and Epinay (48B) studied the condensation products resulting from the reaction of benzaldehyde and methyl ethyl ketone under conditions leading to synthesis of straight-chain ketones. Van Dorp and Arens (7‘4B)investigated the condensation of some ketones with hydroxy maleic anhydride in the presence of hydrogen chloride. Kharasch, McBay, and Urry (41B)showed how to synthesize some 1,4diketones by reaction of diacetyl peroxide with aliphatic ketones. Nazarov and Nagibina (66B)disclosed a method for synthesizing polycyclic ketones containing a cyclopentanone nucleus with an angular methyl group. Ardashev (2B)investigated the simultaneous condensation of acetone with aromatio amines and ethylene glycol to produce quinaldine derivatives. Bradsher, Brown, and Blue ( 8 B ) studied the reaction between acetophenone and some substituted benzaldehydes using sodium hydroxide in ethyl alcohol as the catalyst. Cologne and Dreux (16B)prepared some dihydropyran derivatives by the condensation of a-vinyl ketones. Dubois (2OB) investigated the effect
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of potassium hydroxide additions on the condensation of acetone and ethyl methyl ketone with acetaldehyde in methanol. Ipatieff and Idnn (38B)revealed details of a continuous process for converting alkyl ketones into polyalkylbenzene hydrocarbons in which aqueous ammonium halide solutions serve as the catalyst. Galitzenstein and Woolf (28B) disclosed details of a process for manufacturing acetylenic alcohols by condensing ketones with acetylene in the presence of potassium salts of primary and secondary alcohols. Bakalar (3B) patented a process for condensing aralkyl compounds with ketones in the presence of sulfuric and phosphoric acid. A patent issued to the Standard Oil Development Company (69B) disclosed a process and a suitable catalyst for condensing ketones and aldehydes in the vapor phase to produce unsaturated ketones and aldehydes. A patent granted to Roche Products, Ltd. (62B), revealed that zinc activated with iodine is an effective catalyst for condensing alkyl halides with a,p-unsaturated ketones. CONDENSATIONS OF ALDEHYDES
Slobodin, Rachinskiil, and Avtokratova (67B) studied the reversibility of the esteric condensation of aldehydes employing high temperatures and metal oxide catalysts. Villani and Nord investigated the influence of various metallic alkoxides on the course of condensation reactions of aldehydes and showed that by changing the metal, trimeric glycol esters could be produced instead of simple esters ( 7 6 B ) ; these same researchers ( 7 7 B ) investigated the catalytic action of aluminum and magnesium aluminum ethylate on the condensation of various nitroparaffins with aldehydes. Spasov and Ivanov (68B) studied the condensation of dichloroacetaldehyde with aromatic aldehydes and ammonia. Optimum conditions for condensing 6-bromopiperonal with malonic acid ( 5 8 B ) and various amides (69B)were investigated by Pandya and his co-workers. Pandya and his colleagues, in the course of studying the condensation of aldehydes and amides, reported on the reactions of heptaldehyde (60B),cinnanialdehyde (&‘E?), dihydrocinnamaldehyde (7B, 56B), and 5-chloro- and 3,5-dichlorosalicylaldehyde(54B, 55B). Caesar and Sachanen (IOB) investigated the condensation of formaldehyde and thiophene under acidic conditions. The condensation of chloral with p-chlorobenzenesulfonic acid ( 1 6 B ) and various acylanilides ( 6 B ) was investigated by Cook and Cook and Berlin, Shchukina and Sazanova. klacovski and Georgescu (4813) discussed the preparation of 2-carbamyI-4-nitrostilbine by the condensation of aromatic aldehydes using sodium methylate. The condensation of some amino aryl sulfones with aldehydes was investigated by Fel’dman and Syrkin (WdB). Hull (97B)obtained a patent for a process for carrying out aldol condensations, in which very high yields are obtained by careful control of the addition of the liquid acetaldehyde t o the caustic solution. Details of a process for manufacturing substituted dihydropyrans from m,p-unsaturated aldehydes were revealed in two patents granted to Whetstone (79B). General conditions for condensing aliphatic aldehydes with other compounds using fluorosulfuric acid were revealed in a patent granted to Kemp (4OB). CONDENSATION OF ALCOHOLS AND RELATED COMPOUNDS
Zal’kind and Kakhniashvili (8WB) investigated the condensation of benzyl alcohol with m- and o-dihydroxybenzene. Tsukervariik and Polctaev ( 7 3 B ) studied the condensation of some butyl and amyl alcohols with benzene and toluene. Cadwallader, Fookson, Biears, and Howsrd (BB) prepared an extensive series of substituted ttlcohols and ketones by carrying out aliphatic halide-carbonyl condensations in the presence of sodium. Wolk (8OB) gave details of an electrolytic process for manufacturing l,&butylene glycol from ethyl alcohol by an aldol condensation. Rertrand (6B)studied the condensation of 2,7-dibromoxanthydrol with urea, veronal, gardenal, and various alcohols. Becker and
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Barthell ( 4 B ) prepared an extensive series of glycol ethers of different phenols by condensing phenol with ethylene oxide. Carroll ( I f B )and Carroll and Mason ( I Z B ) patented a process for manufacturing monophenolic and monotolyl glyceryl ethers by Condensing phdnol or its homologs with glycerol, using an alkali metal salt of a low molecular weight fatty acid as a catalyst. Shishido, Nozaki, and Iwako (66B) investigated the effect of different solvents on the condensation of biacetyl with phenol and phenolic derivatives. CONDENSATION OF NITROGENOUS COMPOUNDS
Christen, Prijs, and Lehr ( f 4 B )investigated the condensation of biacetyl with primary aromatic amines in the presence of phosphoric acid. Petrov and Sapozhnikova ( 6 f B )investigated the reaction of acrylonitrile with piperylene and isoprene. Sallmann and Granacher (64B) patented a process for condensing amides with aldehydes and bisulfites. Jones ( 3 9 B ) studied the general synthesis of 2-hydroxypyrazines by condensing a-amino acid amides with appropriate compounds in ethyl alcohol saturated with ammonia. Adams and Schrecker ( 1 B ) carried out a thorough investigation of the activity of the 6-methyl group in 1substituted 2-pyridones in condensing reactions as a possible aid to the synthesis of cytisine. A patent issued to Imperial Chemical Industries, Ltd. ( f 9 B ) , reveals details for preparing a series of antimalarial compounds which involve the condensation of arylamines and halogen substituted pyrimidines. Kogan and Shchukina (42B) studied the condensation of quinolinic acid anhydride and chlorobenzene. Mann and Beeby ( 4 4 B ) prepared some 2,7-disubstituted compounds of 1,2,3,4-tetrahydrisoquinolineby condensing reactions involving the isoquinoline derivative with various primary amines. Weiss and Hauser ( 7 8 B ) carried out some acylation8 and carbethoxylations of quinaldine, using sodium and potassium amide as the condensing agent. Meyer and Bouchet (49B)investigated the condensation of 4-chloroquinaldine with compounds containing active methylene groups. Grignovskil ( S f B ) studied the activity of Raney nickel as a condensing medium in the formation of biacridines from chloroacridines. MISCELLANEOUS CONDENSATION REACTIONS
Szmuszkovicz and Modest (71B) employed a condensing reaction involving maleic anhydride to synthesize 7-methoxy-3,4benzophenanthrene. Chakravarti ( I S B ) prepared ethyl 2,4,4triniethylcyclopentanone-2carboxylate and 2,4,4-trimethylcyclopentanone by condensing reactions. Meek, Lorenzi, and Cristol ( 4 6 B ) investigated the condensation of l-pheny1-1,3butadiene with acrylic acid and acrolein. Meek and Ragsdale ( 4 7 B ) studied the condensation of piperylene with acrylonitrile and methyl acrylate. Hawkins and Bennett (96B) revealed details of a process for preparing ethers of chlorinated tetrahydropyrans. Eidus, Zelinskir, and Puzitskir (21B) investigated the influence of space velocity and feed composition on the hydrocondensation of ethylene and carbon monoxide; and Treves (72B) studied the catalytic effect of various ketones and alcohols on the oxidative condensation of 2-methoxy-4-nitrotoluene.
DESULFURIZATION Literature appearing during the review period dealing with the removal of compounds containing sulfur from gases and liquids by both chemical and physical means is treated in this section. DESULFURIZATION OF FUEL GASES
Marshall ( S I C ) presented a review of various wet and dry processes that have been utilized for removing sulfur compounds from fuel gas, including lime, iron oxide, activated carbon, liquid absorbants, and bacterial action, and concluded that the industrial trend is toward the use of small boxes charged with very active
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iron oxide. Ohlenschlager (342) presented a similar review, tabulating seventeen processes that can be used to remove hydrogen sulfide from coke oven gas. DRY METHODS
Means to desulfurize fuel and synthesis gas by dry methods were discussed by Perna and Dolgzalik (S8C) who described the preparation of porous catalysts impregnated with sodium carbonate and the hydroxides of titanium, cerium, nickel, and chromium and tabulated experimental data on the performance of these catalysts. Williamson and Gardside (47C) presented data on some laboratory scale experiments for two desulfurization processes using iron oxide powders under fluidized conditions. A patent granted to Henry Balfour and Co., Ltd. (4C),describes the preparation and utilization of a copperized steel wool catalyst which is effective a t elevated temperatures in converting organic sulfur to hydrogen sulfide and which partially oxidizes the hydrogen sulfide to sulfur dioxide. A patent assigned to Imperial Chemical Industries, Ltd. ( d I C ) , describes a pelleted manganese oxide catalyst that is effective a t elevated temperatures in removing organic sulfur and hydrogen sulfide from gases and vapors. The Gas, Light, and Coke Company secured a patent for a pelleted catalyst consisting of pure cobalt or nickel sulfide for removing organic sulfur from gases (18C). The preparation of some nickel and cobalt hydrogenation and chromium oxide and sulfide catalysts and the application of these in a two-stage gas desulfurization process are revealed in a patent that was assigned to the Gas Research Board (19C). A process and catalysts Consisting of carbonates, oxides, and hydroxides of alkaline earth metals and mixtures of these suspended on coke are discussed in a patent obtained by Derham and Johnson ( I 2 C ) . In two patents assigned to Compagnie pour la fabrication des compteurs et mathiel d'usines A gaz (IOC) details of a fluidized process for desulfurizing coal gas with iron oxide and active carbon and methods of regeneration are described. Brusset (QC) made some x-ray diffraction studies of active carbon suitable for desulfurizing coal gas and concluded that the average pore diameter of such carbon is less than 60 A. In a patent assigned to the Standard Oil Development Company by Owen (arc)a catalytic process for desulfurizing hydrocarbon synthesis gases is described, and the ,preparation of copper, aluminum, chromium, tungsten, mangnganese, molybdenum, and vanadium catalysts suspended on alumina is discussed. Haywood and Laidler (2%') disclosed that barium carbonate suspended on asbestos is a suitable catalyst for removing sulfur compounds from gases and is readily regenerated by air blowing. WET METHODS
Details concerning the removal of sulfur compounds from gases by wet methods in existing plants are discussed. Weitzel and Muldrew (46C) described a natural gas purification plant in which a mixture of diethanolamine, diethylene glycol, and water is used as the desulfurizing fluid. Albright (IC) discussed a similar plant in which diethanolamine is employed as the scrubbing medium. Eymann ( I 6 C )gave some operating details of a multistage process for removing hydrogen sulfide from gases in which an aqueous solution of ammonia is the absorbant. PATENTS
Blohm, Riesenfeld, and Frazier ( 6 C ) developed a process that utilizes an aqueous mixture of amines and monohydric alcohols. Udy (46C) disclosed means to promote the reaction between hydrogen sulfide and sulfur dioxide by passing the gases through an 'aqueous solution of alkali metal sulfites. Gollmar (20C) revealed a process that utilizes alkali metal carbonates and regeneration by countercurrent aeration under vacuum at relatively low temperatures. Mitchell and Gollmar (S2C) described a
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process in which regeneration of the absorbant liquid is accomplished by distillation under vacuum, permitting the use of coke quench water as the heating medium. Oldach (%C) disclosed complete details for a six-stage process that can utilize many aliphatic amines in oil as the absorbant. Denig ( 1 I C ) and Shaw ( @ C ) described five- and six-stage processes that combine many of the features disclosed in the patents of Mitchell and Gollmar. DESULFURIZATION OF PETROLEUM MATERIALS
The use of clays, alumina, and silica as percolation and catalytic contact agents was described. Ballard, Merritt, and Oosterhout (6C)reported results of some preliminary investigations on the desulfurization of some high-sulfur straight-run middle distillates by vapor contacting with No. 1 Riverside earths. Haresnape, Fidler, and Lowry (22C) studied the adsorption of different sulfur compounds on silica gel and evaluated thz relative retentivity of these sulfur compounds on the gel. Hockberger (24C) disclosed details of a process for desulfurizing triisobutylene by percolation through silica gel, and a similar process that utilizes dehydrated bauxite instead of silica was patented by Brandon ( 7 C ) . A patent granted to the Phillips Petroleum Company (S9C) disclosed operating details of a process for desulfurizing cracked gas distillates that uses a mixed silica-alumina catalyst. Details of processes that employ metallic contact catalysts were discussed. Hale, Simmons, and Whisenhunt ( S I C ) investigated the catalytic sweetening of high-sulfur crude oils, and determined the completeness of sulfur removal as a function of space velocity and operating temperature for several catalysts. Hoffman (26C) disclosed that the stability and life of desulfuriration catalysts consisting of oxides of cobalt and molybdenum on alumina are increased by the addition of small amounts of silica. Krug (28C)gave directions for preparing a desulfurization catalyst Consisting of boron phosphate and alumina. Nachod (332) patented a process employing a catalyst composed of lead and copper aluminosilicates, Strang (2C) disclosed operating details of a two-stage process for desulfurizing hydrocarbon gases that employs molybdenum bxide suspended on alumina. Engel (16C) patented a process for the vapor phase desulfurization of distillates that uses active carbon impregnated with alkali compounds. Hoover (26C) tabulated operating and cost information for the Airco-Hoover-Cooper sweetening process for converting mercaptans into noncorrosive disulfides and disclosed that a slurry of diatomaceous earth and cupric chloride serves as the catalyst. Processes for removing mercaptans by solvent extraction using methanol and sodium hydroxide mixtures were patented by Brown and Gerhold (8C) and Drennan ( I S C ) . Oosterhout (BC) was granted a patent for removing mercaptans from naphthas by extraction with aqueous solutions of srtlts of alkylsubstituted mononuclear aromatic monocarboxylic acids, as cumic acid. In a patent i s a e d to the Shell Development Company (&C), it was revealed that regeneration of alkali solutions used for desulfurizing is catalyzed by additions of such oxidizing agents as nitrodiamino-, nitrodihydroxy-, or nitroaminohydroxybenzene. In similar patents obtained by the Pure Oil Company (4OC) and Hoppel and Cauley (271'2) the oxidizing Catalysts are phenolic compounds capable of oxidizing to quinones such as tannic acid and pyrogallol. Fuqua ( 1 7 C ) discussed the Kascade column aa an improved mercaptan extraction unit, and presented operating data and costs for such a system operated with tannin solutions. Ayers and Lyon (SC) patented a process for removing sulfur and organic polysulfides that uses an alkali metal stannite solution. Desulfurization processes employing hydrogen fluoride are considered. Schneider and Feichtinger (4%) compared the sulfur-extracting ability of 98% hydrogen fluoride to that of sulfuric acid and potassium hydroxide solutions containing potassium isobutyrate a0 a solutizer. Lien, McCaulay, and Evering (SOC) studied and tabulated the selectivity of liquid hydrogen fluoride as a solvent for various organic sulfur com-
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pounds. Lien and Evering (29C)patented a high pressure process for desulfurizing aromatic hydrocarbons with liquid anhydrous hydrogen fluoride and disclosed means of regenerating the hydrogen fluoride. I n a patent granted to Elliott and Holm ( f 4 C )it was disclosed that a two-stage process consisting of an extraction by sulfur dioxide followed by a similar one by hydrogen fluoride is superior to the use of but one of these media.
REDUCTION ELECTROLnlC PROCESSES
Experimental investigations on the electrolytic reduction of organic acids that were reported for the review period include the following: Swann, Wanderer, Schaffer, and Streaker (7’90) investigated the influence of cathode materials and their physical structure on the reduction of maleic acid to succinic acid in sulfuric acid and reported yields obtained for cathodes consisting of copper, zinc, cadmium, mercury, aluminum, tin, lead, bismuth, iron, cobalt, and nickel. Wibaut and Boer ( 9 8 0 ) described several cell arrangements that can be used to reduce 2- and 4-pyridine monocarbosylic acids to the corresponding methylpyridines. Iagaryshev and Aryamova ( 3 7 0 ) studied the reduction of oxalic acid in sulfuric acid, using lead, amalgamated lead, platinum, copper, and iron electrodes in a ceramic diaphragm-type cell. Some experiments on the reduction of crotonic acid in sulfuric acid solutions to butyric acid, butanol, and crotyl alcohol using lead cathodes were d_escribed by Dineen, Schwan, and Wilson ( 1 4 0 ) . LukBs and Sorm ( 5 8 0 ) investigated the electrolytic reduction of some keto acids as y-acetylbutyric, ypropionylbutyric, 7-e-diketocaprylic, p-acetylglutaric, and hydrochelidonic, and compared the reaction products obtained with those resulting from the Clemmensen reduction of these acids. Patents granted for processes involving the electrolytic reduction of organic acids and esters include the following: Dillon (1.90) disclosed details of a process for preparing Iactaldehyde from lactic acid; Hoffmann-La Roche and Company (278) described a cell and process for preparing sugars from polyhydroxy carboxylic acid lactones; details of a related process were revealed in a patent granted to Roche Products, Ltd. (660); and Spiegelberg ( 7 6 0 )disclosed features of B method for reducing pentanoic icid lactones to ribose. Electrolytic reduction of sugars was described. Sanders and Hales ( 6 9 D ) discussed the influence of current density, initial sugar concentration, ratio of cathode area to catholyte volume, alkalinity of catholyte, and temperature on the reduction rate of glucose in production-type cells. Belen’kaya and BelozerskiI ( 3 0 ) were also concerned with the optimum conditions for the electrolytic reduction of glucose and claimed that best results are obtained in cells equipped with nickel-aluminum or amalgamated lead cathodes and dense nonfilterable diaphragms such as porcelain, using sodium or lithium sulfate catholyte, and operated a t low current densities a t high pH and temperature with stirring. Creighton and Hales ( 1 1 0 ) revealed details of a process for reducing sugars in diaphragm-type cells equipped with amalgamated lead or zinc cathodes and in which the polyhydric alcohols produced are low in sorbitol content. Electrolytic reduction of nitrogenous compounds was treated by the following investigators: Dunet and Willemart (16D) studied the electrolytic reduction of phthalimide in water, dioxane, hydrochloric acid, methanol, and ethyl alcohol solutions and found that replacing dioxane by methanol and ethyl alcohol changes the product from hydroxyphthalimidine to methoxyand ethoxyphthalimidine. Szmaragd and Briner (810 )discussed the thermodynamics of the electrolytic reduction of pyridine to piperidine and investigated the influenee of the electrode material on the course of the reaction. Levchenko (560) studied the electrolytic reduetion of quinaldine in potassium hydroxideethyl alcohol solutions. Galinovsky and Schmid (880) studied the reduction of hydroxysparteine to sparteine.
Vol. 42, No. 9
Some miscellaneous electrolytic reductions that were reported are not classifiable in the previous categories. Takagi, Suzuki, and Imaeda ( 8 6 0 )found that p-thiocresol results when p-toluenesulfonyl chloride is reduced electrolytically in alcoholic sulfuric acid solutions. Lebedeva (540)investigated the effect of different metals as cathodes on the reduction of dimethylethynyl and dimethylvinyl carbinols. Bludworth, Robeson, and Truby ( 5 0 )disclosed details of an electrolytic process and cell for producing allyl alcohol from propenal. A patent assigned to Ward, Blenkinsop and Co., Ltd. (88D), reveals details for preparing pinacols and pinacolines by reduction of the appropriate ketones. In a patent issued to Hoffmann-LaRoche,Inc., ( 2 8 0 ) ,details of an electrolytic cell adaptable for many organic reductions in which the catholyte can be agitated without disturbing the liquid alkali metal amalgam cathode are disclosed. REDUCTIONS INVOLVING USE OF SODIUM
Watt and Moore ( 8 9 D )studied the reduction of bismuth iodide by sodium in anhydrous ammonia solutions and investigated the reducing power of sodium bismuthide. The sodium reduction of esters were considered by the following: Adkins and Gillespie ( 1 0 ) reduced ethyl oleate to oleyl alcohol; Kapron ( 4 6 0 ) investigated the reduction of ethyl butyrate and some ester-ketone and ester-aldehyde mixtures by sodium in acid media; Cason, Brewer, and Pippen (80) studied the sodium reduction of some alkyl-7-valerolactones and showed this to be a suitable means for preparing pure branched-chain alcohols; Kastens and Peddicord ( 4 8 0 ) discussed the sodium reduction of esters as an important commercial method for preparing alcohols of any desired chain length and degree of unsaturation. Patents involving sodium as a reducing agent were granted. Blinoff ( 4 0 )revealed details for a continuous process for preparing low molecular weight alcohols such as butanol and amyl alcohol by reducing esters with molten sodium under milling conditions. Anglaret (36D) patented a process for reducing esters and glycerides, involving the use of ammonium chloride and carbon dioxide to prevent the alcoholates produced from modifying the other reaction prod1 cts. A French patent ( 7 4 0 )disclosed details of a continuous process for reducing esters to alcohols in anhydrous media in equipment in which contact with air is avoided. Breivogel (60) revealed details of a process for reducing ketones to pinacoles with a special sodium-lead alloy. LITHIUM ALUMINUM HYDRIDE
Lithium rtluminum hydride and compounds related to it have become popular reducing agents with organic chemists. The utilization of lithium aluminum hydride to reduce esters was reported by the following investigators: Karrer, Portmann, and Suter ( 4 7 0 ) studied the reduction of some a-amino carboxylic acid esters, particularly the ethyl esters of alaline, leucine, and proline. Karrer and Portmann investigated some of the amino alcohols resulting from the reduction of arecoline, the ethyl ester of guvacine, and diethyl glutamate (46D) and studied the reduction of methyl tryptophanate ( 4 6 0 ) . Schmid and Karrer ( 7 1 0 ) reduced some toluenesulfonic esters. Bachmann and Dreiding (8D) carried out the reduction of methyl cis-2-methyl-2-carbomethoxycyclohexane acetate. Karrer and Banerjea ( 4 9 D ) studied the reduction of coumarin and o-coumaric acid. Reduction of oximes by lithium aluminum hydride was reported who reduced the oximes of enanthaldehyde, by Larrson (63D), benzaldehyde, and cyclohexanone among others, and Ruzicka, Kobelt, Hafligtr, and Prelog (67‘0),who prepared a large number of compounds containing polymethylenimine rings by the reduction of the corresponding cyclanone isoximes. Other reductions using lithium aluminum hydride as a reducing agent were reported. Nystrom and Brown ( 6 3 0 )carried out some reductions of nitrogenous compounds, halides, and quinones; Sampey and Cox (680) reduced anthracene and phenanthrene; Sroog, Chih, Short,
September 1950
INDUSTRIAL A N D ENGINEEJIING CHEMISTRY
and Woodburn ( 7 7 0 ) investigated the reduction of some chloro acid derivatives; Wooten and McKee (960) reduced phenanthridine; Zeiss, Slimowicz, and Pasternak (98D)reduced podo# a i rpic acid; Julian and Printy (410)studied the reduction of some oxindoles. The success of lithium aluminum hydride as a reducing agent suggested that similar compounds such as lithium and sodium borohydride might possess comparable desirable reducing properties. Chaikin and Brown (90) investigated the ability of sodium borohydride to reduce aldehydes, ketones, and acid chlorides and found that it reduces these compounds to alcohols, but has little reducing action on carboxylic acids and acid anhydrides and no effect a t all on esters and nitriles. Further investigations by Nystrom, Chaikin, and Brown (6.40) on the reducing action of lithium borohydride indicated that it is more active than sodium borohydride, but milder than lithium aluminum hydride, reducing aldehydes and ketones rapidly a t room temperature, while r e a c t ing slowly in the case of esters. INORGANIC COMPOUNDS
Reductions were carried out on inorganic compounds employing elements as the reducing agent. Lyon, Olson, and Lewis (690) described a process for preparing very pure silicon apectrographically free of metallic impurities, that involves the reaction of silicon tetrachloride with zinc vapor. Kroll, Anderson, Holmes, Yerkes, and Gilbert (610) discussed a large laboratory scale method for preparing zirconium metal sponge, in which magnesium is used to reduce zirconium chloride in a vacuum melting and distillation unit. I n a patent granted to the Westinghouse Electric International Company ( 9 1 0 ) details of a process for producing metallic thorium by reducing chlorides and oxychlorides of thorium with calcium are disclosed. Hurd ($40) described methods for preparing boron hydrides by the reducing action of aluminum, zinc, magnesium, sodium, sodium hydride, and calcium hydride on boron halides in hydrogen atmospheres. The use of carbon and silicon or compounds containing them an reducing agents was reported. Franck and Wallouch (%ID) described a vacuum process for reducing magnesia to magnesium with calcium carbide; in a related paper, Schneider and Hutt ( 7 2 0 ) studied the influence of temperature and particle sire in the reduction of magnesia with calcium carbide. Gel'd, Kologreeva, and Serebrennikov (980)determined the velocity of reduction of silica, using carbon, silicon carbide, ferrosilicon, and silicon as reducing agents. Vickery and Edwards ( 8 7 0 ) found that the vapor phase reduction of arsenic trioxide by carbon monoxide is much faster and more complete than the solid phase reduction. Reductions of inorganic compounds by hydrogen were reported. Wyss ( 9 7 D )investigated the kinetics of the reduction of titanium dioxide and some titanates in a closed system in which the temperature variation was linear with respect to time. A patent granted to the Westinghouse Electric International Company (900)revealed details for reducing ammonium molybdate to molybdenum. Tatievskaya, Antonov, and Chufarov (830, 8.40) studied the kinetics of the reduction of some oxides of manganese in hydrogen, and compared the reduction speeds with those obtained using carbon monoxide. Halla, Egartner, and Weil (NO)investigated the reduction of sodium tungstate and molybdate. Kubaschewski (680) investigated the possibility of reducing the chlorides of magnesium and aluminum to the metals. CATALYTIC HYDROGENATION OF ORGANIC COMPOUNDS
Starkey and Bremner (780) disclosed means for reducing furfural to furfuryl alcohol using a cobalt catalyst. Two patents assigned to the Iowa State College Research Foundation (994 400) revealed details for preparing 2-methylfuran by reducing
17616s
furfural and furfuryl alcohol using copper and chromium. Horning and Reisner (300)used a palladium catalyst for reducing some keto acids. Trenner and Bacher (860) investigated the production of erythritols by the catalytic reduction of esters of tartaric acid using copper and chromium. A patent issued to Sandos, Ltd. (TOO),revealed details for preparing a copper catalyst that is effective in the reduction of high molecular weight aliphatic acid esters to the corresponding alcohols. Pritchard ( 6 6 0 ) disclosed details of a process that employs nickel for reducing carboxylic diesters of 1,l-diglycols. Lolkema, Vlugter, and van Westen ( 6 7 0 ) revealed means of preparing hexitols and sorbitol from hydrolyzed starch in the presence of nickel. Mayo and Hurwitz (600) investigated the reduction of bromobenzene to biphenyl using lead. Knott (600) used nickel in the reduction of p-cycloylpropionitrile. Wilson (960) found that methylfuran reduces to tetrahydromethylfuran when nickel is used, but that propyl acetate production is favored with the use of cobalt, copper, and iron. Hull and Quarles (330)disclosed methods for preparing a very active and readily regenerated alcohol reducing catalyst containing copper, zinc, and nickel. MISCELLANEOUS REDUCTIONS
Hydrazine hydrate was used as the reducing agent in the material reported by the following: King and Nord ( 4 9 0 ) studied the reduction of thiophene aldehydes and ketones; Fand and Lutomski (19D)reduced 3-acetylpyridine; a general process for reducing carbonyl compounds to the corresponding methylene compounds with almost quantitative yields was revealed in a patent assigned to Merck and Co., Inc. (380). Investigations in which the emphasis was on reduction in general and in which many types of reductions were attempted with different agents in each case include the following: Sorm (760) studied the products resulting from the reduction of picolinic and nicotinic acids. Slabey and Wise (73D) reduced methyl cyclopropyl ketone to methylcyclopropylcarbinol. Newman, Underwood, and Reno11 (62D)attempted some reductions of 1,2-epoxydecane and styrine oxide. Jadot (390)investigated the products resulting from the reduction of some p-diketones to the corresponding diols. Hewett, Lermit, Openshaw, Todd, Williams and Woodward (860)investigated the products resulting from the reduction of arsacridine. Furst ($10)reduced 2-acetylpyridine to 2-ethylpyridine. Reductions employing metal alkoxides were reported. Campbell and Khanna (70) reduced some dibenzoethylenes to the corresponding biphenylacyls using aluminum isopropoxide. Jackman, Macbeth, and Mills (880)reduced some cyclic ketones using the aluminum alkoxides of isopropyl alcohol and butanol, and determined the relative proportions of the epimeric alcohols in the reaction products. n u n e t and Willemart ( l 7 D ) prepared some hydroxyphthalamidinecr by reducing phthalamide and its derivatives with magnesium methylate. Leekley ( 6 6 0 ) disclosed details of a process for simultaneously reducing and dimerizing acrylonitrile to adiponitrile using magnesium a h holates. Reductions were carried out using acid and metallic zinc or magnesium an the reducing agent. Wiemann and Glacet (98D) reduced m&vI oxide with acetic acid, magnesium, and zinc, and found that the reaction products contain, among other things, saturated ketones, ethylenic alcohols, diethylenic glycol, and furan-type compounds. Ihienne and Bichet (18D)reduced 9, IO-diphenyl-1 ,+anthraquinone to 9,10-diphenyl-1,4-diketo-1,2,3,4-tetrahydroanthracene using acetic acid and zinc and hydrogen iodide as the reducing agents. Clemmensen-type reactions were who studied the carried out by Clems, Raper, and Vipond (10D), reduction of 1-keto-octahydropyridocollineand Dev ( I g D ) , who investigated the reduction of ,9-(Z-p-cymoyl) propionic acid. Doak and Corwin ( 1 6 0 )discovered that the a-position is about 25 times more susceptible to reduction by hydrogen iodide than
INDUSTRIAL AND ENGINEERING CHEMISTRY
1766
the 0-position in iodopyrroles. Williniann and Schine ( 9 4 0 ) investigated the Bouveault-Blanc reduction of 8-ketal esters to the corresponding ketal alcohols. Mustafa (610) prepared cisdimethylstilbene by the reduction of 2,3-diphenyl butadiene with carried out the reduction picric acid. Karrer and Pletscher (440) of the methiodides of 2-methoxyphenanthroline. Howton and Golding ( S I D ) studied the products resulting from the reduction of a-phenacylpyridine. In a patent granted to Sweet (800) it is revealed that the sodium hydrosulfite reduction of 2-anthraquinone carboxylic acids is better accomplished in acid than alkaline media. Groombridge (2.40)patented a process for synthesizing carboxylic acids and esters by the catalytic reaction of chlorinated hydrocarbons with carbon monoxide and steam in the presence of metals that have a tendency to form metal carbonyls. In a French patent issued to I. G. Farbenindustrie A,-G. (560)details of a catalytic process for synthesizing esters of unsaturated carboxylic acids by reaction of substituted acetylenes with carbon monoxide were disclosed. Teter ( 8 5 0 ) patented a multistage process for reducing cobalt oxide with hydrogen followed by ammonia, and indicated that the cobalt produced by such reductions is useful as a catalyst in the synthesis of amines and nitriles from olefinR and ammonia.
LITERATURE CITED C A W NATION
(1A) Atherton, C. R., Rock Products, 52, No. 6, 126, 135 (1949). (2A) Azbe, V. J., Ibid., 52, No. 2, 98-101 (1949). (3.4) Zbid., 52, NO.4, 121-3, 166-7, 169 (1949). (4-4) &be, V. J. (to Aabe Corp.), U. S. Patent 2,470,543 (May 17, 1949). (5-4)Barnard, C. H., Rock Products, 52, No. 8, 142-5, 180 (1949). (6A) Block, B., Socker Handl., 4,195-205 (1948). (7A) Brumbaugh, C. C., Chem. Eng. Progress, 44,881-6 (1948). (86) Davis, G. J., Inst. Fuel, Pulv. FueE Conf., June 1947, 8224. (9A) Ellerbeck, T. R., U. S. Patent 2,451,024 (Oct. 12, 1948). (10-4) Geidelman, M.M., Sakharnaya Prom., 20, No. 3, 26-9 (1947). (11.4) Gezburg, V. A., Ogneupwy, 13, 282-3 (1948). (12A) Gibadlo, F., Rock Products,52, No. 9, 63-4 (1949). (13A) Gibbs, R., Paper Ind. and Paper World, 30, 1614-16 (1948). (14.4) Zbid., 31, 1070-3 (1949). (15A) Gibbs, R., Rock Products, 53, No. 2, 118-21, 143 (1950). (16.4) Hashimoto, K., and Mochinaga, H. (to K. K. Hidachi Seisakujo), Japan. Patent 175,055 (July 29, 1948). (17A) Jaspers, M. J. M., Re*. mattiauz construction trav. publ., C , No. 409, 344-8 (1949). (HA) Ibid., NO. 410, 373-8 (1949). (19A) Ibid., NO. 411, 421-5 (1949). (20A) Junnemann, M. de, SOC.ing. Civil France Bull., 1947, 109-10. (21A) Keller, J., Swiss Patent 246,664 (Oct. 16, 1947). (22A) Khodorov, E. I., Tsement, 13,No. 2, 8-14 (1947). (23A) Ibid., 13, No. 9,8-13 (1947). (24A) Ibid., 14, NO. 1, 3-7 (1948). (25.4) Khodorov, E. I., and Diment, P. M., Ibid., 13, No. 3, 8-12 (1947). (268) Kite, R. P., and Roberts, E. J., Chem. Eng., 54, No. 12, 112-135 (1947). (27A) Lacy, G. R., Rock Products, 52, No. 6,120-1, 134-5 (1949). (%A) Lellep, 0. G., U. S. Patent 2,466,601 (April 5, 1949). (29A) Lenhart, W. B., Rock Products, 50, No. 11,86-7, 104 (1947). (30A) Ibid., 52, NO. 9, 70-3,85 (1949). (31A) Lifshits, M. A., Ogneupory, 13, 26-32 (1948). (32A) Lonza ElectrizitBtswerke und chemische Fabriken A.-G., Swiss Patent 251,381 (Aug. 2, 1948). (336) Lur’e, Y. S., and Val’berg, G. S., Tsement, 13, No. 1, 3-9 I1 \ _R47\ _ -,..
(34A) Ibid., 13, NO. 2, 3-8 (1947). (35A) Martin, W. S.,U. S. Patent 2,471,882 (May 31, 1949). (36A) Maschinenfabrik Oerlikon, Swiss Patent 252,976 (Oct. 16, 1948). (37.4) Matouscheck, F., Rev. m7 driaux construction trav. publ., C, 1948, 150-1. (38A) Nordberg, B., Rock Products, 50, No. 3.70-3 (1947). (39A) Phillipp, L. S., Ibid., 52, No. 3, 81-5 (1949). (40A) VaInrub, L. G., Ogneupory. 12, 166-73 (1947). (41A) Wassmer, H., Swiss Patent 264,189 (Dec. 1, 1948). (42A) White, F. S. (to Dorr Co.), U. S. Patent 2,465,410 (March 29, 1949). (43.4) Whitney, W. T., and Hollingsu-orth, C. A., IND.ENO.CHEW, 41, 1325-7 (1949).
Vol. 42, No. 9
CONDENSATION
Adams, R., and Schrecker, A. W., J . Am. Chem. Soc., 71,118695 (1949). Ardaahev, B.I., Zhur. Obschchel Khim., 19, 1656-63 (1949). Bakalar, A. B. (to Shell Development Co.), U. S. Patent 2,455,643 (Dec. 7, 1948). Becker, B.,and Barthell, E., Monatsh., 77, 80-5 (1947). Berlin, A. Y., Shchukina, M. N., and Sazanova, E. D., Zhur. Obschel Khim., 19, 677-82 (1949). Bertrand, J., Compt. rend., 225, 1331 (1947). Bhandari, R. R., and Pandya, K. C., J . Indian Chem. SOC.,26, 219-20 (1949). Bradsher, C. K., Brown, F. C., and Blue, W. B., J . Am. Chem. SOC.,71, 3570 (1949). Cadwallader, E. A,, Fookson, A., Mears, T. W., and Howard, F. L., J . Research Natl. Bur. Standards, 41, 111-18 (1948). Caesar, P. D., and Sachanen, A. N., IND. ENG.CHBY.,40, 9228 (1948). Carroll, M. F,, U. S. Patent 2,486,925 (Nov. 1, 1949). Carroll, M. F., and Mason, R. G., Zbid., 2,486,926 (Nov. 1, 1949). Chakravarti, R. N., J . Chem. SOC.,1947, 1028-9. Christen, F., Prijs, B., and Lehr, H., Helv. Chim. Acta, 32, 5662 (1949). Cologne, J., and Dreux, J., Compt. rend., 228, 582-3 (1949). Cook, W. A., and Cook, K. H., J. Am. Pharm. Assoe., 38, 23941 (1949). Croxall, W. J., and Fegley, M. F., J . Am. Chem. Soc., 71, 12012 (1949). Croxall, W. J., and Schneider, H. J., Zbid., 71, 1257-60 (1949). Curd, F. H. S., Davis, M. I., Rose, F. L., Tuey, G. A. P., and ImperiaI Chemical Industries, Ltd., Brit. Patent 587,550 (April 29, 1947). (20B) Dubois, J. E., Bull. SOC. chim. France, 1949, 66-8. (21B) Eidus, Y. T., Zelinskii, N. D., and Puzitskii, K. V., Izuesl. Akad. Nauk S. S. S.R.,Otdel, Khim. Nauk, 1949,110-14. (22B) Fel’dman, I. K., and Syrkin, 2. N., Zhur. Obahchel Khim., 19, 1369-73 (1949). (23B) Frostick, F. C., and Hauser, C. R., J . Am. Chem. SOC.,71,13502 (1949). (24B) Fuson, R. C., and Mum, G.,Zbid., 71, 1116 (1949). (25B) Gakhokidze, A. M., Zhur. Obshchet Khim., 17, 1327-31 (1947). (26B) Gakhokidze, A. M., and Guntsadze, A. P., Ibid., 17, 1640-1 (1947). (27B) Zbid., p. 1642. (28B) Galitaenstein, E. G., and Woolf, C. (to Distillers Co.), U. S. Patent 2,488,082 (Nov. 15, 1949). (29B) Gheorghiu, C. V., and Budeanu, C., Ann. sci. uniu. Jassy, 31, Pt. I (1948). (30B) Green, N., and LaForge, F. B., J. Am. Chem. Soc., 70, 2287-8 (1948). (31B) Grignovskiy, A. M., Zhur. Obshchel Khim., 17, 1124-8 (1947). (32B) Hamell, M., and Levine, R., J . Org. Chem., 15, 162-8 (1950). (33B) Harris, S. R., and Levine, R., J . Am. Chem. Soc., 70, 3360-1 (1948). (34B) Ibid., 71, 1120-1 (1949). (35B) Hauser, C. R., Ringler, B. I., Swamer, F. W., and Thompson, D. F., Ibid., 69, 2649-51 (1947). (36B) Hawkins, P. A., and Bennett, N. (to Imperial Chemical Industries), U. S.Patent 2,439,928 (April 20. 1948). (37B) Hull, D. C. (to Eastman Kodak Co.), Zbid., 2,468,710 (April 26, 1949). (38B) Ipatieff, V. N., and Linn, C. B. (to Universal Oil Products Co.), Zbid., 2,431,754 (Dec. 2, 1947). (39B) Jones, R. G., J . Am. Chem. Soo., 71, 78-81 (1949). (40B) Kemp, W. E. (to Dominion Tar and Chemical Co.), Can. Patent 445,094 (Nov. 18, 1947). (41B) Kharasch, M. S., McBay, H. C . , and Urry, W. H., 2. Am. Chem. Soc., 70, 1269-74 (1948). (42B) Kogan, I. M., and Shchukina, L. A,, Zhur. Priklad. Khim., 19, 925-30 (1946). (43B) Macovski, E., and Georgescu, J., Compt. rend. acad. sci. Roumanie, 8, 75-6 (1946-47). (44B) Mann, F. G., and Beeby, M. H., Nature, 162,337-8 (1948). (45B) Mariella, R. P., and Kvinge, V., J . Am. Chem. Soc., 70, 3126-8 (1948). (460) Meek, J. S., Lorenzi, F. J., and Cristol, S.J., Zbid., 71, 1830-2 (1949). (47B) Meek, J. S., and Ragsdale, J. W., Zbid., 70, 26024 (1948). (48B) Metayer, M., and Epinay, N., Compt. rend., 226, 1095-7 (1948). (49B) Meyer, A,, and Bouchet, G., Ibid., 227,345-7 (1948). (50B) Mittal, D. S.,Proc. Wail. Acad. Sci. India, 15A, 10-11 (1946). (51B) Munch-Petersen, J., and Hauser, C. R., J . Am. Chem. Soc., 71, 770-3 (1949). (52B) Saaarov, I. N., and Nagibina, T. D., Zhur. Obshchel Khim., 18, 1090-6 (1948).
September 1950
INDUSTRIAL AND ENGINEERING CHEMISTRY
(53B), Newman, M. S., and Magerlein, B. J., 070.Reactions, 5, 413-40 (1949). ,-- -_, Nigam, R. G. S., and Pandya, K. C., Proc. I d a n Acad. Sd., 29A, 56-63 (1949). Ibid., pp. 364-6. Pandya, K. C., and Bhandari, R. R., J. Indian Chem. SOC.,24, 185-8 (1947). Ibid., p. 209. Pandya, K. C., Pandya, R. B., and Sethi, R. L., Proc. Indian Acud. Sci., 27A, 240-3 (1948). Pandya, K. C., and Sethi, R. L., J . Indian Chem. SOC.,25, 1457 (1948). Pandya, K. C., and Sodhi, H. S., Proc. Indian A d . Sci., 27A, 196-201 (1948). Petrov, A. A., and Sapozhnikova, A. F., zhus. Obshchef Khim., 18, 424-9 (1948). Roche Products, Ltd., Brit. Patent 617,482 (Feb. 7,1949). Royals, E. E., J. A m . Chem. SOC.,70,489-91 (1948). Sallmann, R., and Griinacher, C. (to Ciba Ltd.), U. S. Patent 2,479,782 (Aug. 23, 1949). Shishido, K., Noraki, H. Z., and Iwako, To,J . A m . Chem. SOC., 71, 2037-41 (1949). Skinner, G. S., and Anderson, E., and Bogart, R. F., Ibid., 71, 1482-3 (1949). Slobodin, Y. M., Rachinskii, F. Y., and Avtokratova, 0. D., Zhur. Obshchel:Khim., 17,584-90 (1947). Spasov, A., and Ivanov, I., Annuatre univ. Sofia, Facult6 sd., 44,Lime 2,157-61 (1947-48). Standard Oil Development Co., Brit. Patent 610,752 (Oct. 20, 1948). Steck, E. A., and Holland, A. J., J. A m . Chem. Soc., 70, 440 11948). Szmusakovicz, J., and Modeit, E. J., Ibid., 70,25424 (1948). Treves, G. R., Ibid., 70, 875-6 (1948). Tsukervanik, I. P., and Poletaev, A. V., Zhur. Obshchel Khim., 17, 2240-3 (1948). Van Dorp, D. A,, and Arens, J. F., Rec. trav. chim., 67,459-68 (1948). Vil&,J. P., and Balleater, M., Anales real soc. espafi.$8. g quim., 45B, 87-8 (1949). Villani, F. J., and Nord, F. F., J . A m . Chem. Soc., 69, 2605-7 (1947). I M . , p. 2608. Weiss, M. J., and Hauser, C. R., J . A m . Chem. SOC.,71, 2023-6 (1949). Whetstone, R. R. (to Shell Development Co.), U. S. Patents 2,479,283, 2,479,284 (Aug. 11, 1949). Wolk, I. L. (to Phillips Petroleum Co.), Ibid., 2,419,515 (April 22, 1947). Yost, R. El., and Hauser, C. R., J . A m . Chem. SOC.,69, 2325-8 (1947). Zal'kind, Y. S., and Kakhniashvili, A., Zhur. Obshchel Khim., 19,717-19 (1949). Zellars, G. R., and Levine, R., J . Org. C h m . , 13, 160-3 (1948)DESULFURIZATION
r
(1C) Albright, J. C., Petroleum Engr., 21C, No. 2, 21-30 (1949). (2C) Anglo-Iranian Oil Co., Ltd., and Strang, L. C., Brit. Patent 602,097 (May 20, 1948). (3C) Ayere, G. W., and Lyon, P. (to Pure Oil Co.), U. S. Patent 2,435,732 (Feb. 10, 1948). (4C) Balfour & Co., Ltd., Henry, Burns, W. L., and Bureau, A. C., Brit. Patent 601,094 (April 27, 1948). (5C) Ballard, W. P., Merritt, N. A., and Oosterhout, J. C. D., IND. ENB.CHEM.,41, 2856-60 (1949). (6'2) Blohm, C. L., Riesenfeld, F. C., and Frazier, H. D. (to Fluor Corp.), U. S. Patent 2,445,468 (July 20, 1948). (7C) Brandon, R. C. (to Standard Oil Development Co.), Ibid., 2,436,550 (Feb. 24,1948). (8C) Brown, K. M., and Gerhold, C. G. (to Universal Oil Productg , Co.), Ibid., 2,437,348 (March 9, 1949). (9C) Brusset, H., Compt. rend., 227, 843-5 (1948). (1OC) Compagnie pour la fabrication des compteurs et materiel d'usines h gaz, French Patents 935,311 (June 16, 1948) and 935,357 (June 17, 1948). (11C) Denig, F. (to Koppers Co.), U. S. Patent 2,458,505 (Jan. 11, 1949). (12C) Derhem, L. J., and Johnson, F. J., Brit. Patent 613,651 (Dec. 1, 1948). (13C) Drennan, H. E. (to Phillips Petroleum Co.), U. S. Patent 2,452,040 (Oct. 26, 1948). (14C) Elliott, L. P., and Holm, M. M. (to California Research Corp.), Ibid., 2,440,258 (April 27, 1948). (15C) Engel, W. F. (to N. V. Bataafsche Petroleum Maatschappij), Dutch Patent 61,745 (Oct. 15,1948).
1167
(16C) Eymann, C., Uas-u. Wasserfach, 90,505-12, 534-8, 568-70, 577-81 (1949). Fuqua, F.'D., Petroleum Processing, 3,1050-1 (1948). Gas, Light, and Coke Co., Griffith, R. H., Newling, W. B. S., and Plant, J. H. G., Brit. Patent 600,787 (April 19, 1948). Gas Research Board and Eastwood, A. H., Ibid., 605,838 (July 30, 1948). (2OC) Gollmar, H. A. (to Koppers Co.), U. 8. Patent 2,490,799 (Dec. 13, 1949). (21C) Hale, J. H., Simmons, M. C., and Whisenhunt, F. P., IND. ENQ.CHEM.,41, 2702-8 (1949). (22C) Hareenape, D., Fidler, F. A., and Lowry, R. A., Ibid., 41, 2691-7 (1949). (23'2) Haywood, F. W., and Laidler, D. 5. (to Wild-Barfield Electric Furnaces), U. S. Patent 2,444,930 (July 13,1948). (24C) Hockberger, W. G. (to Standard Oil Development Co.), Ibid., 2,469,726 (May 10,1949). (25C) Hoffman, H. C. (to Union Oil Go. of California), Ibid., 2,437,533 (March 9, 1948). Hoover, C. O., PetroZeun Refiner, 27, 355-9 (1948). Hoppel, J., and Cauley, S. P. (to Socony-Vacuum Oil Co.), U. 8.Patent 2,453,067 (Nov. 2, 1948). Krug, R. C. (to Atlantic Refining Co.), Ibid., 2,441,493 (May 11, 1948). Lien, A. P., and Evering, B. L. (to Standard Oil Co. of Indiana), Ibid., 2,464,520 (March 15, 1949). ENG. Lien, A. P., McCaulay, D. A., and Evering, B. L., IND. CHEM.,41,2698-702 (1949). Marshall, J. R., Gas World,129, No. 3338, Coking Sect., 105-14 (1948). Mitchell, J., and Gollmar, H. A. (to Koppers Co.), Brit. Patent 605,633 (July 28, 1948). Nachod, F. C. (to Atlantic Oil Refining Co.), U. S. Patent 2,422,982 (June 8,1948). Ohlenschlager, W., Chem. Tech., 1, 160-7 (1949). Oldach. C. S. (to E. I. du Pont de Nemoure & Co.), U.S. Patent 2,475,334 (July 5, 1949). (36C) Oosterhout, J. C. D. (to Texas Co.), Ibid., 2,439,670 (April 13. 1948). (37C) Owen, J. J. (to Standard Oil Development Co.), Ibid., 2,468,510 (April 26, 1949). (38C) Perna, F., and Doleralik, V., Paliva, 30,2-7 (1950). (39'2) Phillipe Petroleum Co., Brit. Patent 614,636 (Dec. 20, 1948). (40C) Pure Oil Co., Ibid., 629,914 (Sept. 30, 1949). (41C) Reynolds, P. W., Grudgings, D. M., and Imperial Chemical Industries, Ltd., Ibid., 615,770 (Jan. 11, 1949). (42C) Schneider, K., and Feichtinger, H., Angew. Chem., B20, 12-16 (1948). (43'2) Shaw, J. A. (to Koppera Co.), U. S. Patent 2,490,840 (Dec. 13, 1949). (44C) Shell Development Co., Brit. Patent 597,655 (Jan. 30,1948). (45C) Udy, M. J., Ibid., 599,073 (March 4, 1948). (46C) Weitzel, H. P., and Muldrew, W. E., Gas Age, 102, No. 7, 77,120,122, 124 (1948). (47C) Williamson, R. H., and Gardside, J. E., Inst. Gas Engrs., Commun. 357 (1949). REDUCTION
Adkins, H.. and Gillespie, R. H., Org. Syntheses, 29, 80-2 (1949). Bachmann, W. E., and Dreiding, A. S., J. A m . C h a . SOC.,71, 3222-3 (1949). Belen'kaya, N. G., and BelorerskiI, N. A,, Zhur. ObshcheZ Khim., 19, 1664-8 (1949). Blinoff, V. (to Societe anon. d'innovatione chimique dite: Sinnova au Sadic), U. 8. Patent 2,460,969 (Feb. 8, 1949). Bludworth, J. E., Robeson, M. O., and Truby, H. A. (to Celanese Corp. of America), Ibid., 2,462,301 (Feb. 22,1949). Breivogel. P. J. (to White Laboratories). Ibid.. 2,477,216 (June 28, 1949). (7D) Campbell, N., and Khanna, N., Nature, 161,565 (1948). (8D) Cason, J., Brewer, P. B., and Pippen, E. L., J. Org. Chem., 13, 239-48 (1948). (9D) Chaikin, 5. W., and Brown, W. ?., J. A m . Chem. SOC.,71, 122-5 (1949). (10D) Clems, G. R., Raper, R., and Vipond, H. J., J . Chem. Soc.. 1949, 2095-7. (11D) Creighton, H. J., and Hales, R. A. (to Atlas Powder Co.), U.S. Patent 2,458,895 (Jan. 11, 1949). (12D) Dev, S., J . Indian Chem. SOC., 26, 31-3 (1949). (13D) Dillon, C. S., Brit. Patent 611,674 (Nov. 2, 1948). (14D) Dineen, E., Schwan, T. C., and Wilson, C. L., J . EIectroclwn. SOC.,96, 226-33 (1949). (15D) Doak, K. W., and Corwiii, A. H., J. A m . Chem. Soc., 71, 169-63 (1949).
INDUSTRIAL AND ENGINEERING CHEMISTRY Dunet, A., and Willemart, A., Bull. soc. chim. France, 1948, 887-9. Ibid., pp. 1045-6. atienne, A., and Bichet, G., Compt. rend., 229, 1154-6 (1949). Fand, T. I., and Lutomski, C. F., J . Am. Chem. Soc., 71, 2931 (1949). Franck, H. H., and Wallouch, R., 2. anorg. Chem., 257,316-39 (1948). Furst, A., J . A m . Chem. Soc., 71, 3550-1 (1949). Galinovsky, F., and Schmid, H., Monatah., 79, 322-4 (1948). Gel’d, P. V., Kologreeva, A. G., and Serebrennikov, N. N., Zhur. Priklad. Khim., 21,1261-71 (1948). Groombridge, W. H., Brit. Patent 621,520 (April 11, 1949). Halls, F., Egartner, L., and Weil, R., Momtah., 78, 155-62 (1948). Hewett, C. L.,Lermit, L. J., Openshaw, H. T., Todd, A. R., Williams, A. H., and Woodward, F. N., J . Chem. Soc., 1948, 292-5. Hoffmann-Ls Roche & Co., A,-G., Swiss Patent 258,581 (May 16, 1949). Hoffmann-LaRoche, Inc., Brit. Patent 599,140 (March 5,1948). Holdren. R. F. (to Iowa State College Research Foundation), U.S. Patent 2,445,714 (July 20, 1948). Homing, E. C., and Reisner, D. B., J. A m . Chem. Soc., 71. 1036-7 (1949). Howton, D. R., and Golding, D. R. V., J. Org. Chem., 15, 1-7 (1950). Huang-Minion (to Merck and Co.), U. S. Patent 2,471,697 (May 31, 1949). Hull, D. C., and Quarles, J. F. (to Eastman Hodak Co.), Ibid., 2,475,965 (July 12, 1949). Hurd, D. T., J . A m . Chem. SOC.,71,20-2 (1949). I. G. Farbenindustrie A.-G., French Patent 930,368 (Jan. 23, 1948). Institut Technique d’ E’tudes et de Recherches des Corps Gras and Anglaret, P., French Patent 930,269 (Jan. 21, 1948). Izgaryshev, N. A., and Aryamova, I. I., Zhur. Obshchet Khim., 18,337-44 (1948). Jackman, L. M., Macbeth, A. K., and Mills, J. A,, J . Chem. SOC.,1949, 2641-6. Jadot, J., Bull. soc. chim. belges, 57, 346-54 (1948). Johns, I. B., and Burnette, L. W. (to Iowa State College Research Foundation), U. s. Patent 2,458,857 (Jan. 11, 1949). Julian, P. ,L,, and Printy, H. C., J . A m . Chem. Soc., 71, 3206-7 (1949). Kapron, J., Ann. chim., [12] 3, 117-44 (1948). Karrer, P., and Banerjea, P., Helu. Chim. Acta, 32, 1692-3 1‘1949).
(44D) (45D) (46D) (47D)
Karrer,P., and Pletacher, A,, Ibid., 31,786-94 (1948). Harrer, P., and Portmann, P., Zbid., 31, 2088-92 (1948). Ibid., 32, 1034-9 (1949). Karrer, P., Portmann, P., and Suter, M., Z b X , 31, 1617-23 (1948). (48D) Kastens, M. L., and Peddicord, H., IND.ENG. C H ~ M .41, , 438-46 (1949). (49D) King, W. J., and Nord, F. F., J . Org. Chem., 14, 638-42 (1949). (SOD) Knott, E. B., J. Chem. Soc., 1948, 186-8. (5lD) Kroll, W. J., Anderson, C. T.. Holmes, H. P., Yerkes, L. A, and Gilbert, H. L., J . Electrochem. Soc., 94, No. 1, 1-20 (1 948). (52D) Kubaschewski, O., Z. Melallkunde, 39, 18-22 (1948). (53D) Larrson, E., Svensk. K e n . Tid., 61, 242-3 (1949). (54D) Lebedeva, A. I., Zhur. Obshchel Khim., 18, 1161-7 (1948). (55D) Leeltley, R. M. (to E. I. du Pont de Nemours & Co.), U. S. Patent 2,439,308 (April 6, 1948). (56D) Levchenko, V . V., Zhur. Obshchel Khim., 18,1245-8 (1948). (57D) Lolkema, J., Vlugter, J. C., and van Westen, H. A,, Dutch Patent 60,685 (March 15, 1948). (58D) Lukes, R., and germ, F., Collection Czechosloa. Chem. Commum., 13,585-91 (1948).
Vol. 42, No. 9
(59D) Lyon, D. W., Olson, C. M., and Lewis, E. D., J . Electrochem. SOC.,96, 359-63 (1949). (60D) Mayo, F. R., and Hurwitz, M. D., J . A m . Chem. Soc., 71,776-9 (1949). (6lD) Mustafa, A., Zbid., 71,1878-9 (1949). (62D)Newman, M. S., Underwood, G., and Renoll, M. W., IW., 71, 3362-3 (1949). (63D) Nystrom, R. F., and Brown, W. G., Ibid., 70,3738-40 (1948). (64D) Nystrom, R. F., Chaikin, S. W., and Brown, W. G., Zbid., 71. 3245-6 (1949). (65D) Pritchard, W. W. (to E. I. du Pont de Nemoura & Co.), U. S. Patent 2,456,315 (Dec. 14, 1948). (66D) Roche Products, Ltd., Brit. Patent 607,540 (Sept. 1, 1948). (67D) Ruzicka, L., Kobelt, M., HPfliger, O., and Prelog, V., H e b . Chim. Acta, 32, 544-52 (1949). (68D) Sampey, J. R., and Cox, J. M., J. A m . C h . SOC.,71, 1507 (1949). (69D) Sanders, M. T., and Hales, R. A., J . Electrochem. SOC.,96, 24153 (1949). (70D) Sandoz, Ltd., Swiss Patent 256,230 (Feb. 16, 1949). (71D) Schmid, H., and Karrer, P., Helo. Chim. Acta, 32, 1371-8 (1949). (72D) Schneider, A., and Hutt, G., Z . anorg. Chem., 257, 289-316 (1948). (73D) Slabey, V. A., and Wise, P. H., J . Am. Chem. Soc., 71, 3252-3 (1949). (74D) SOC.anon. d’innovations chimiques dite: Sinnova ou Sadic. French Patent 932,001 (March 10, 1948). (75D) h r m , F., Collection Czechoslou. Chem. Communs., 13, 57-73 (1948). (76D) Spiegelberg, H. (to Hoffmann-La Roche), U. 8. Patent 2,457,933 (Jan. 4, 1949). (77D) Sroog, C. E., Chih, C. M., Short, F. A., and Woodburn, H. M., J . A m . Chem, Soc., 71, 1710-11 (1949). (78D) Starkey, F., and Bremner, J. G. M. (to Imperial Chemical Industries), Brit. Patent 605,922 (Aug. 3, 1948). (79D) Swann, S., Wanderer, K. H., Schaffer, H. J., and Streaker, W. A., J . Electrochem. SOC.,96, 353-8 (1949). (80D) Sweet, A. J. (to Allied Chemical and Dye Corp.), U. S,Patent 2,445,699 (July 20, 1948). (81D) Szmaragd, S., and Brinor, E., Helv. Chim. Acta, 32, 553-63 (1949). (82D) Takagi, S., Suzuki, T., and Imaeda, K., J . Pharm. Soc. Japan, 69, 358-61 (1949). (83D) Tatievskaya, E. P., Antonov, V. X., and Chufarov, G. I., Doklady Akad. Nauk S.S.S.R.,68,561-4 (1949). (84D) Tatievskaya, E. P., Antonov, V. IC.,and Chufarov, G. I., ICvest. Akad. Nauk S.S.S.R., Otdel, Tekh. Nauk, 1948, 371-83. (85D) Teter, J. W. (t,oSinclair Refining Co.), U. S. Patent 2,437,487 (March 9. 1948). (86D) Trenner, H: R., and Bacher, F. A., J . A m . Chem. Soc., 71, 2352-5 (1949). (87D) Vickery, R. C., and Edwards, R. W., Metalhrgia, 37, 3100-11 (1948). (88D) Ward, Blenkinsop and Co., Ltd., Dickenson, H. G., and Weias, J., Brit. Patent 629,042 (Sept. 9, 1949). (89D) Watt, G . W., and Moore, T. E., J . A m . Chem. Soc., 70, 11971200 (1948). (SOD) Westinghouse Electric International Co., Brit. Patent 609,487 (Oct. 1, 1948). (91D) Ibid., 623,160 (May 12, 1949). (92D) Wibaut, J. P., and Boer, H., Rec. trav. chim., 68, 72-6 (1949). (93D) Wiemann, J., and Glacet, C . , Compt. rend., 226, 923-5 (1948). (94D) Willimann, L., and Schinz, H., Helu. Chim. Acta, 32, 2151-64 (1949). (95D) Wilson, C. L., J . A m . Chem. SOC.,70, 1313-15 (1948). (96D) Wooten, W. C., and McKee, R. L., Ibid., 71, 2946 (1949). (97D) Wyss, R., Ann. chim., I121 3, 215-42 (1948). (98D) Zeiss, H. H., Slimowicr, C. E., and Pasternak, V. Z., J . Am. Chem. Soc., 70, 1981-2 (1948). RECEIYED July 10, 1950.
End of Third Annual Unit Processes Review (Reprints of this or the first and second Unit Processes Reviews may be purchased for 50 cents each from the Reprint Department, American Chemical Society, 1155 Sixteenth St., N. W., Washington 6, D. C.)
