INDUSTRIALand ENGINEERING CIIEMISTRY
EDITIO
N
V o l . 3 1 , C o n s e c u t i v e N o . 10 Published
by
the
AMERICAN CHEMICAL SOCIETY HARRISON E. HOWE,
Editor
MARCH 10, 1939
V O L U M E 17
N e w fighting p l a n e e q u i p p e d w i t l i e n g i n e s c o o l e d by glycol.
NUMBER 5
N o w a t e r is u s e d .
Industrial Applications o f the Glycols 1 H . B. McClure Carbide a n d C a r b o n C h e m i c a l s C o r p . , New York, Ν . Υ.
U
NTIL recently, many chemicals were known in tne laboratory 50 t o 100 years before t h e y were produced in commercial quantities. This condition is gradually being remedied by industry as its chemical needs become more numerous and complex, and the present-day average from "test tube t o tank car" is usually conceded t o be 7 years. Recently, a rec ord was set when the first tank car of a new plasticizer for a safety-glass resin was shipped only 3 years from the time it was first synthesized in t h e laboratory. Ethylene glycol was known (51, 52) in the laboratory for over 60 years before it was produced commercially (42). As soon as it became available in large quantities, how ever, research men found large markets for it and its derivatives, and its commercial uses multiplied quickly. In the decade since the first tank car of ethylene glycol was shipped, six different glycols (39) and fifty glycol derivatives have been made commercially available. Seventeen have already reached a stage of industrial importance (18) which re quires their shipment in tank-car quanti ties. T h e number of amine, ester, ether, and other derivatives of the glycols in creases almost monthly. To say that their industrial uses are legion would be conservative. A recent count indicated that there are 143 different applications for the glycols without con sidering their derivatives. Almost any object we see about us, if made within the last few years, has been affected in some manner during its manufacture by a glycol or a glycol derivative. Therefore, w e con fine ourselves here to the more important industrial uses. 1 Presented at the Glycol Symposium of the American Association for the Advancement of Science a t Richmond, Va.. December 27. 1938.
Antifreeze Uses
I n 1921, t h e Bureau of Standards drew up a set of requisites for a suitable auto mobile cooling system antifreeze (14)The primary requirement, of course, was that it should prevent freezing of the cool ant without injuring the engine and ra diator parts. Since ethylene glycol had these properties, in addition to being odor less and nonevaporating in water solutions and having n o effect o n lacquered finishes, it was synthesized commercially during the middle twenties (8, 9, 2JÇ). To adapt it t o automobile cooling system use, an inhibitor formula was made from a number of special ingredients in fractional percentages, particularly intended to protect the cooling system against the corrosive action of water (49). Water containing the inhibitor is 95 per cent less corrosive on iron and steel and 75 per cent less on aluminum and other radiator metals than plain water. Leakage and foaming have also been reduced to a point where the solution compares favorably with water. Under the registered trade-marks "Everready" "Prestone," this antifreeze is used by hundreds of thousands of motorists. T h e antifreeze uses of the glycols are not confined to automobile radiators. The antifreeze grade of ethylene glycol is also used in sprinkler systems for unheated buildings and in place of salt solutions in brine systems where corrosion is a factor. Propylene glycol is being used (29) in increasing quantities a s an antifreeze in brine systems for cooling milk and beer. Engine Coolant During the past ten years, a great deal of development work has been done on glycol-cooled aircraft motors (15, 16). In these, the ethylene glycol does not 149
function as an antifreeze but as a coolant (81). No water is used, as the jacket temperatures approximate 250° F.—well above the boiling point of water. The chief advantage of high-temperature cooing is reduced frontal area. T h e small radiator required offers less resistance than an air-cooled engine of the same horsepower, resulting in greater speed. In addition, the weight of the engine is reduced as compared with a water-cooled engine, which requires more plumbing and a larger radiator. A plane with a hightemperature cooled engine provides better visibility than one with an air-cooled engine. The ship that finished third at the 1938 Cleveland air races had a glycolcooled motor, as had also the U. S. Army bomber that broke a speed record recently between Dayton and Buffalo while carrying a full load. The use of the glycols as high-temperature coolants has been extended to x-ray tubes, machine guns, and U. S. Army tanks. Low-Freezing Dynamites Surveys have indicated that, previous to the successful solution of the problem of frozen dynamite, 89 per cent of the accidents in handling dynamite occurred during the winter months and were the indirect result of freezing. Glycerol trinitrate freezes at moderately cool temperatures, both by itself and as an ingredient of dynamites. Frozen dynamite is relatively insensitive and cannot be detonated by a commercial blasting cap. The hazard arose when insufficient precautions were taken in thawing t h e frozen dynamite. Since the original invention of dynamite by Nobel in 1866, one of the important advances in the science of explosives has been the inclusion of freezing inhibitors in nitroglycerine dynamites, the most effec-
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M o d e m s m a l l dry e l e c t r o l y t i c r a d i o c o n d e n s e r s m a d e p o s s i b l e by e t h y l e n e glycol. tive of which is ethylene glycol dinitrate (2, 18,28,26,88). Although it was known 34 years ago (22) t h a t ethylene glycol dinitrate was t h e ideal antifreeze for glycerol trinitrate, it was not until t h e glycol became industrially available t h a t this use became significant (87), T o d a y mixtures of ethylene glycol and glycerol are nitrated with sulfuric and nitric acids t o form solutions of glycol dinitrate in glycerol trinitrate which do not freeze a t —87° F . These dynamites are slightly less sensitive to shock, but they can be detonated just as readily (5) and thermodynamically they are t h e equivalent of t h e straight glycerol product. Dynamites m a d e from diethyiene glycol (25, 40) are slightly superior in this respect, especially when cellulose nitrate is incorporated to form gelatin dynamites. Since a major portion of our mining, roadbuilding, and construction work is carried on at temperatures below t h e freezing point of glycerol nitrate, t h e commercial availability of glycol 12 years ago was welcomed b y t h e makers a n d users of dynamite. Electrolytic C o n d e n s e r s Solutions of boric acid in ethylene glycol are being widely used (41) to form the electrolyte in electrolytic condensers. These condensers resemble t h e familiar "jelly roll"—the cake portion being represented by two sheets of aluminum foil, and t h e jelly portion by a sheet of paper or cloth impregnated with t h e glycol-boric acid paste. Pure, low-chloride glycol is used because it will dissolve appreciable quantities of boric acid, giving one of t h e best nonvolatile, liquid conductors of electric current t h a t will not corrode aluminum. T h e nonconductor of t h e condenser is t h e film of aluminum oxide t h a t is anodically deposited on t h e surface of t h e aluminum foil. T h e function of t h e glycol paste is to give a more intimate contact between t h e oxide film a n d the other sheet of aluminum. T h e two sheets of aluminum, separated by a sheet of paper or cloth, are formed into a roll. This is impregnated a t elevated temperatures with t h e glycol solution of boric acid, which contains a trace of ammonia or ethanolamine t o prevent t h e acid from attacking t h e aluminum. W h e n t h e roll has cooled, a potential is applied across the poles of t h e condenser until a n adequate layer of t h e nonconducting aluminum oxide is formed. Should this oxide film become cracked or rup-
CHEMISTRY
tured in service, t h e subsequent passage of current through t h e condenser will again anodically oxidize t h e aluminum a n d restore t h e continuity of t h e film. T h u s , t h e condenser is self-healing. This condenser is less expensive t h a n t h e type which uses waxed paper as t h e nonconductor, and is m u c n more compact t h a a condensers made of alternate layers of aluminum a n d air. Without these compact condensers condensers t thata h a t are compact are used used to to eliminate " h u m , " the modern midget radio set would not be possible. These electrolytic condensers are also used extensively in household electric refrigerators t o a t t a i n a high initial torque when the motor s t a r t s under load. Induction motors were used previously, and it was necessary t o bring a special three-phase current to t h e home. As these new, less expensive condensers are perfected, they are meeting a wider acceptance by electrical engineers. Plasticizer A p p l i c a t i o n s All t h e lower members of t h e glycol family are soluble in water and compatible with gelatin glues; hence they are popular piasticizers for adhesives used in m a n y industries. In addition to being generally as effective as glycerol for this purpose, some glycols are superior for special applications. For example, when diethyiene glycol is used in the usual flour-base bookbinder's paste, i t causes less warping of t h e book covers on drying than glycerol. Because diglycol is a solvent for nitrocellulose, t h e diglycol pastes bite into bindings made of artificial leather and produce better anchorage. T h e glycols a n d glycerol (28) seem to be about equal in producing t h e desired resiliency in the glue-type rollers for printing presses. These rollers are made by heating together t h e desired proportion of plasticizer, gelatin glue, a n d water. W h e n t h e thick solution becomes homogeneous, it is poured into cylindrical molds a r o u n d t h e center steel shaft. On cooling, solidification takes place, a n d after removal from the mold, t n e print roll is ready to spread the ink evenly over the type face in t h e press. Hot glycol-gelatin glue solutions are also cast in sheets to form hectograph stencils. I n this process, the flexible glue sheet actually applies t h e ink t o t h e paper and makes possible a very economical substitute for printing presses in t h o u s a n d s of offices and schools. Sheets of glue, made flexible with glycols or glycerol, are used as stencils in sandblasting stone and glass (12). T h e sheet, wet on one side, is applied to t h e object to be etched. T h e inscription or design is then cut in t h e flexible glue sheet. T h e flexible glue is sufficiently strong a n d resilient to be unaffected by t h e highvelocity sand particles which gradually erode epitaphs a half inch deep in granite, or etch designs on glass. T h e glycols also form very satisfactory piasticizers for binders in composition cork. T h e mixture of ground cork and plasticized binder is tamped into cylindrical molds to form rods, which a r e subsequently cut into disks. Composition cork gaskets are cut from sheets of t h e glycolplasticized cork. M a n y different types of resin binders a r e used—gelatin glue, casein, or phenolic and alkyd resins. Although t h e polyglycols are solvents for nitrocellulose, t h e y are n o t used as piasticizers b y the lacquer i n d u s t r y be-
VOL. 17, NO. 5
cause of their high solubility in water. Many of their ether and ester derivatives, however, have extremely low vapor pressures and have been found very effective piasticizers for special applications. "Carbitoi"* phthalate a n d methyl "Carbitol" phthalate are unusually good piasticizers for resin films which m u s t be resistant2 to hydrocarbons. Methyl "Cellosolve" phthalate is one of the best cellulose acetate solvents and has a much lower vapor pressure t h a n dimethyl phthalate. Triethvlene glycol dihexoate (which is sold under t h e brand name of "Flexor'* plasticizer 3 G H ) has proved t o be one of t h e most effective piasticizers for the polyvinyl acetals used in safety glass because it maintains desirable flexibility at winter temperatures. Protective Coatings T h e glycols are dihydric alcohols; hence they react with polybasic acids to form resins. The reaction product of ethylene glycol and a dibasic acid, such as phthalic anhydride, is a resin, while t h a t of diethyiene glycol is a balsam-like solid. T h e greater the molecular weight of the polyalkylene glycol used, t h e lower is t h e melting point of t h e resulting resin. Since the alkyd plastics made from glycols are softer than the glycerol analogs, it is possible t o produce resins t h a t do not require t h e addition of piasticizers to a t tain flexibility. Although glycols are not so important industrially as glycerol i n the manufacture of resins for t h e paint, varnish, and lacquer industry, they are used to obtain special effects, and when glycerol prices are high, or when glycerol is difficult to obtain, the glycols can b e employed, at least as a partial substitute. In the field of protective coatings t h e ethers of the glycols have one of their major uses (7, 10, 11, 17, 82, 88, 84, 86). Although ethylene glycol boils a t 198° C . and is practically nonvolatile, its ethyl ether boils at 135° C. and is known as a medium-boiler in nitrocellulose lacquers, where its high solvent power permits t h e use of larger quantities of inexpensive hydrocarbon diluents t h a n do t h e alkyl acetates, such as butyl a n d a m y l acetate. T h e three most important of these glycol derivatives are Ceilosolve, butyl Cello* The words "Carbitoi/' "Ceilosolve," "Carboeeal," "Chlorex," and "Plexol" are registered trade-marks of Carbide and Carbon Chemicals Corp.
T h e glycol-derwative plasticizer i n t h e bonding r e s i n of t h i s n e w s a f e t y g l a s s allows t h e g l a s s t o be b e n t a n d rolled if cracked b y i m p a c t .
The AMERICAN CHEMICAL SOCISTT assumes no responsibility for the statements and opinions advanced by contributors to its publications.
compact condensers thata are used to . ._ _._ _ __ __ . . _ year. w_ w w Edition monthly on the first; Analytical Edition monthly on the 15th; News Edition on the 10th and 20th. Acceptance for mailing at spécial rate of postage provided for in section 1103. Act of October 3, 1917, authorised July 13, 1918. SuBSCBXFTiov to nonmembers, IWDUBTKIAL AND ENGINEERING CHEUIBTBY complete, 86.00 per year; foreign postage $2,40, except to countries accepting mail at American domestic rates; Canada, 80 cents. Analytical Edition alone, $2.50 per year; foreign postage, 60 cents; Canada, 20 cents. News Edition alone, $1.50 per year (single copies, 10 cent·); foreign postage, 60 cents; Canada, 20 cents. Subscription», changes of address, and claims for lost copies should be sent to Charles L. Parsons, Secretary, 728 Mills Building, Washington. D . C .
MARCH 10, 1939
N E W S EDITION
151
solve, and Cellosolve acetate (10, 36). Their pleasant odor makes them particu larly desirable for brushing lacquers (34). The glycols and their ethers are used extensively in the manufacture of wood stains. In earlier days, the furniture industry used stains made by dissolving oil-soluble dyestuffs in hydrocarbon-type solvents. Although water-soluble dyestuffs were known to be superior to the oil-soluble colors, they were not widely employed for staining because of the tendency of their aqueous solutions to raise the grain of furniture woods. B y means of the glycols and their ethers, the water-soluble dyestuffs can be dissolved and applied to wood with a minimum of grain-raising difficulty. Textiles Of the several glycols and their deriva tives which have diversified uses through out the textile industry, diethylene glycol (19, 20, 21) is probably the most impor tant. When worsted fibers are scoured, they lose some of their natural oils and become slightly brittle. It is necessary, therefore, to coat them with a product that will per mit one fiber to pass over the other during the many mechanical operations involved in the processing of wool stock into yarn. All these operations are for the purpose of combing the woolen fibers parallel to each other and thereafter twisting them in order to gain strength. Unless the fibers are lubricated, there will be excessive breakage. Until the past few years, only natural vegetable and animal oils, such as olive oil and lard oil, were used for this purpose. As such oily lubricants must be completely removed by scouring before the finished yarn or fabric can be successfully bleached or dyed, the entire industry has been seeking a product that would lubri cate and yet be dissolved simply by im mersion in water. Diethylene glycol has proved (19, 21) the most suitable of the glycols for this purpose. Since it is com>letely water-soluble and yet has desirable ubricating properties, many drum car loads have been used by the worsted industry. Diethylene glycol also has an advantage over natural oils in that it is odorless, colorless, and does not become rancid when stored for a long time. During the early days of the present Spanish conflict, the supplies of olive oil were very limited. This shortage caused the National Association of Wool Manu facturers to start research on substitutes for olive oil. So far, the glycols and their water-soluble derivatives are showing great promise in this application. The glycols are used in many ways by the textile industry wherever a hygro scopic substance is needed (19), since they take up 25 to 50 per cent of their own weight of water at ordinary room humidi ties. When skeins of silk arrive from the Orient, they are coated with a sericin wax which must be softened before they can be unraveled and wound on bobbins for knitting and weaving. This softening is accomplished by immersing the skeins for several hours or overnight in a water emul sion of oils containing a hygroscopic sub stance, such as diethylene glycol. In textile sizing operations, glycols are added to the starch solutions to prevent the gums and starches from drying out and becoming brittle on the warps with subse quent flaking off and clogging of the loom equipment. This property of hygroscopicity has also led to their use in the formulation of textile printing pastes. These concentrated water solutions of dyestuffs and starches are picked up from a trough by a rotating engraved roll which subsequently applies the dye paste to the fabric. Diethylene glycol prevents ex
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E t h y l e n e glycol i s t h e major c o n s t i t u e n t of t h e " p e r m a n e n t " t y p e of antifreeze for a u t o m o t i v e cooling s y s t e m s .
cessive drying out in the troughs or in the pails in which the dye paste is stored. As a solvent for the dyes themselves, diethylene glycol performs another and perhaps more important function. From the standpoint of chemical structure, di ethylene glycol contains not only two alcohol groups but also an ether-oxygen atom. This combination makes it supe rior to glycerol as a dye solvent. Several glycol ethers are also used in important quantities, because of their dye solvent properties. Thus Cellosolve and Carbitol—the ethyl ethers of ethylene glycol and diethylene glycol, respectively—are the preferred solvents in textile printing for work with basic dyestuffs or the reduced type of vat dyes (19). The glycols are also excellent mutual solvents. A mutual solvent, or coupling agent, is a material which, when added to two normally immiscible substances, pro duces a single, homogeneous system of all three components. For example, potas sium oleate and other alkali soaps will not dissolve in mineral oil, yet when a small amount of diethylene glycol is added, a clear solution is obtained. This property of diglycol is extensively used throughout the textile industry in the formation of rayon coning oils, silk soaking oils, woolen and worsted lubricants, or wherever it is desirable to supply an oil which will emulsify itself when added to water. Many other industries make use of such oils. If it were not for the fact that leather is fat-liquored with this type of product, it would be brittle instead of pliable. The metal industry uses large quantities of cutting oils for lubricating and cooling the cutting tools of lathes, drill presses, and other metal-working ma chines. These soluble oils are essentially solutions of soaps in mineral oil. In many cases, the use of a glycol or a glycol ether is necessary to hold the soap in solution in the oil. This mutual solvent property is also made use of in the dry-cleaning indus try to make the soaps dissolve in the cleaning naphtha. An important application for diethylene glycol was developed several years ago. Cast-iron pipe joined by bell-and-spigot
joints packed with jute or hemp fiber has been widely used in this country since the beginning of the manufactured gas indus try. The condensate from manufactured gas kept the jute moist and prevented its drying out and shrinking. With the wide spread use of natural gas and dry manu factured gas, the joints dried out and leak age resulted. 2 "Carboseal" antileak, a mixture of glycols and other materials, is being widely applied (46) to cast-iron gas dis tribution systems t o moisten and swell the dried-out fibrous packing material and is saving the gas companies thousands of dollars annually in reduced unaccountedfor gas losses. Mains treated 6 years ago and without subsequent applica tions of Carboseal antileak still remain tight. It is conservatively estimated that the life of this treatment is at least 12 to 15 years. This swelling of certain textile fibers has led to other uses of the glycols—for ex ample, diethylene glycol will swell cellulose acetate rayon, with the result that dyestuffs are more readily and more evenly absorbed by the fiber. G a s Dehydration Another use of diethylene glycol which has become important is for the dehydra tion of natural gas which is pumped through transmission lines at high pres sures (1, 4, β, 43). Being very hydro scopic, diethylene glycol removes most of the water vapor from the gas, thus mini mizing corrosion and preventing clogging of the line owing to the formation of natural gas hydrates, high-melting-point solids which form in high-pressure gas at tem peratures up to 60 * F. when condensed water is present. Removal of the water vapor with diethylene glycol guarantees full line capacity during cold weather when peak load conditions exist. Diethylene glycol and monoethanolamine are being mixed together in several plants both to desulfurize and t o dehydrate the gas. This gives a dry noncorrosive sulfur-free gas having the characteristics required for most efficient and trouble-free transmis sion in long overland pipe lines.
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INDUSTRIAL AND ENGINEERING CHEMISTRY
VOL. 17, NO. 5
T A B L E I. NAMB Ethylene glycol Diethylene glycol Triethylene glycol Tetraethylene glycol Propylene glycol Di propylene glycol 1,3-Butylène glyool Methyl Celloeolve Diethyl Celloeolve Celloeolve solvent Butyl Celloeolve Phenyl Celloeolve Benzyl Celloeolve Methyl Carbitol Diethyl Carbitol Carbitol solvent Butyl Carbitol Dimetboxytetraglyco Methyl Celloeolve acetate Celloeolve acetate Glycnl diacetate Carbitol acetate Butyl Carbitol acetate Ethylene diamine Diethylene triamine Triethylene tetranaine Monoethanolamine Diethanolamine Triethanolamine Phenyl diethanolamine Ethyl phenyl ethanolamine Phenyl ethanolamine M onoisopropanolamine Triisopropanolami ne Diethylaminoethanol Hydroxy ethyl ethylene diamine Tetraethylene pentamine Ethylene chlorohydrin Propylene chlorohydrin Di glycol chlorohydrin Ethylene dichloride Propylene dichloride Triglycol dichloride Dichloroethyl ether Diohloroieopropyl ether • At 50 mm. b At 5 mm.
PHYSICAL PROPERTIES OF INDUSTRIAL GLYCOLS A N D T H E I R D E R I V A T I V E S BoiUNO VAPOR SOLUBILITY, % B T W T . A T 2 0 * C . POUKOS SP. G R . MOL Water ΡκκββτπΜΒ, F L A S H p a s e G A L . , In Ρτ.. FORMULA WT. Ρτ. water 20 C. 20° C. 2 0 / 2 0 ° C 760 M M . in ο Pm Mm. Hg HOCHsCHsOH 62.07 197.2 1.1155 0.12 9.3 240 Misoible Miscible 9.3 290 244.8 0.01 1.1184 106.12 HOCHtCHtOCHiCHsOH Miscible Miscible Miscible 9.4 330 287.3 J$ï ί^ ^«ΰΙ&ν
(32) Reid, E. W., IND. ENO. CHEM., 26. 21
(1934). (33) Reid. E. W., and Davidson, J. G., Ibid,, 19. 977 (1927). (34) Reid. E. W.. and Davidson. J. G.. Paint, Varnish Production Mgr., 33,6 (1929). (35) Reid, E. W.. and Fife. H. R., IND. EMO. CHBM., 22. 513 (1930).
(36) Reid, E. W., and Hofmann, H. E., Ibid,, 20, 497 (1928). (37) Rinkenbach, W. H., Chem. Met. Eng„ 34, 296 (1927). (38) Rinkenbach, W. H., IND. ENO. CHBM.,
18, 1195 (1926). (39) Ibid., 19, 474 (1927). (40) Ibid.. 19, 925 (1927). (41) Ruben, S., U. S. Patent 1,891.207 (December 13. 1932). (42) Taylor, C. Α., and Rinkenbach, W. Ή.. IND. ENO. CHBM., 18, 676 (1926).
(43) Taylor, F. B . , OU Weekly (August 15. 1935). (44) Trusler, R. B., OU as Fat Industries, 12, 338 (1928). (45) Watson, P. B., U. S. Patent 1,534,752 (April 21, 1925). (46) Williams, D. B., Ibid., 2,094,691 (Octo ber 5, 1937). (47) Wilson, A. L., IND. ESQ. CHEM.. 22,
143 (1930). (48) Ibid., 27, 867 (1935). (49) Wilson, W. H., Automotive Ind., €5, 84-7 (1931). (50) Wood. W. R., and Storrs, B. D., An. Petroleum Inst. (May 24, 1938). (51) Wurt*. Annuals, 104. 174 (1857). (52) Wurts, Compt. rend., 45, 228 (1857).
B a l t i m o r e Meeting Abstracts
•t&éférî
jF\
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* * * » » * * *
" " D O R N in Baltimore--Raised Every- D where," refers to t h e chamberlain (FT. for umbrella) of course. Chemists coming to Baltimore t o attend the spring meeting of t h e AMERICAN CHEMICAL S O -
CIETY, April 3 t o 7, need n o t bring theirs with them, except if they fear the effect of overcalcification due t o prolonged e x posure. The world-famous Hagerstown (Md.) Almanac promises weather for t h e week which will be "fair," subject of course to April's temperamental moods. Our Weather Bureau, in true spirit of hospitality, likewise promises i t s best efforts to keep Old Sol shining. From time immemorial t h e reputation of our state and city for hospitality has been national. "There is a subtle something, hard t o describe—bonhomie, good fellowship—which seems to pervade the very atmosphere of the city." In contrast t o this, fearing that our readers might find it of their o w n accord and accuse us of witholding facts, we quote from Rees* Cyclopedia (1800): "The gaol in this city (Baltimore) is a large building which presents a handsome exterior, that attracts the attention of visitors." Though local chemists know nothing of t h e interior, w e are assured that ο α - , where a is χ
the attraction t o , and χ the proximity of, the interior. The Local Committee Student Membership Awards HE T nually
ENO. CHKM.. 17, 1117 (1925).
(10) Davidson, J. G.. Ibid.. 18, 669 (1926). (11) Davidson. J. G., and Reid, E. W.f Ibid., 20. 199 (1928). (12) Dept. Commerce, U. S. Bur. Standards, Letter Cire. 230 (May 3 , 1927). (13) Dept. Commerce, Serial 2935 (May. 1929). (14) Dept. Commerce, U. S. Bur. Standards, Letter Cire. 28 (December, 1921). (15) Frank, G. W., Aviation (June 1, 1929). (16) Frank, G. W.. S.A.E. Journal (October. 1929).
Lehigh
AMERICAN
(17) Fuller. H. C , IND. ENO. CHEM., 16, 624
(1924). (18) Harry. R. G.. Mfg. Chemist, 8.355 (No vember, 1937) ; Lawrie. J. W„ -Glyc erol and the Glycol»," A. C. S. Mono graph No. 44, New York, Chemical Catalog Co., 1928. (19) Harvey, N . D., Am. Dyeetuff Reptr., 19, 242 (April 14, 1930). (20) Ibid., 19, 185 (March 17, 1930). (21) Harvey, N . D., Textile World, 80, 966 (September 12, 1931). (22) Henry. Ber., 3, 529 (1870). (23) Hibbert. H., U. S. Patent 1,213,367 (January 23, 1917). (24) Ibid., 1,213,368 (January 23, 1917).
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Valley
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SOCIETY
an
awards student membership in the SOCIETY t o those seniors in t h e colleges within t h e section who rank t h e highest for their four years' work. A t the February meeting of t h e section, the following received t h e award: Norma Arnold. Cedar Crest College: Kenneth Betz, Albright College: John D . Cawley, Lafayette College; Frederick Charles Moesel, Lehigh University; and Frank lin Hamm, Muhlenberg College. These students were selected by the chemical faculties of the colleges as the highest ranking student in chemistry in each institution. Student Membership in A. C. S. Awarded
R College, Richmond, Ind., has been awarded the first annual "David Worth OBERT WISSLER, a senior at Earlham
Dennis Award in Chemistry," which is student membership in t h e AMERICAN CHEMICAL· SOCIETY and the choice of one
of the SOCIETY'S journals.
