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VOL. 37

U greatly p r e p o n d e r a t e s in the same position. Note that one is an animal fat and the other a vegetable fat. Application of the method to the hypothetical f a t of known constitution (No. 1) shows t h a t the mathenmtical process is a valid one. As will be described later, other investigators are in agreement with the results. It seems reasonable to conclude that for fats such as these, in which C16-Cls component acids predominate arid in which shorter or longer components are present in relatively small proportions, the process is likely to give a good representation of the actual structure. Shortly a f t e r the foregoing procedure was described in 1959, A. S. Richardson, in private correspondence, described a much simpler method of calculation giving the same results, which p r e s u m a b l y he will describe. Quite rece~ltly Yomlgs (6) has announced the diseovery and development of another process for determini~lg the proI)ortions of the glyceride types and isomers, based on separati(m by means of chromatogr a p h y of the products of partial oxidation of the u n s a t u r a t e d molecules. Analyses by Youngs confirm the accuracy of V a n d c r W a l ' s results. D u t t o n (7) has described recently the application of the counter-curt(rot distribution technique to the analysis of cocoa butter. Ilis article, when published, will contain references 1o other work by means of the same procedure. H a m m o n d (8) has employed the t e m p e r a t u r e gradient technique in resear(.h (m glyceride structure. His results also agree with those of V a u d e r Wal. I t should be obvious by now t h a t rather t h a n being

a helter-skelter, unpredictable, unordered mixture of triglyeeride components, the n a t u r a l f a t s are highly organized and quite predictable. problem is the T IlE END is notofyet. Another greatand animals can explanation how both plants produce such complicated but precisely organized substances as fats. This is p a r t l y the biochemist's and the enzymologist's job, but the m a t h e m a t i c a l relationships discussed in this p a p e r must be satisfied b y a n y system of synthesis they evolve. Indeed these individuals m a y v e r y profitably be guided thereby. F r o m the point of view of the chemist in industrial fats and oils a knowledge of the s t r u c t u r e of fats is as i m p o r t a n t as a road m a p to the traveller. Research heretofore has been done without real knowledge of the s t r u c t u r e of the substances involved and has therefore been carried on in a state of semiblindness. Now we shall be able to see where we are, what we have to work with, and what we can hope to achieve. The results should be better products, more economically produced, with advantages to all concerned.
REFEI~ENCES 1. I I i l d i t c h , T. P., " T h e C h e m i c a l C o n s t i t u t i o n of N a t u r a l F a t s , " 3 r d ed., J o h n W i l e y a n d Sons I n c . , N e w Y o r k ( 1 9 5 6 ) . 2. M a t t s o n , F. H., a n d Beck, L. W., J . Biol. Chem., 219, 735 (1956). 3. M a t t s o n , F. H., a n d L u t t o n , E. S., J . Biol. Chem., 288, 868 (]958). 4. K a r t h a , A. R. S., doctoral thesis, U n i v e r s i t y of l~Iadras, J u l y ] 9 4 9 ; J . A m . Oil C h e m i s t s ' Soc., 30, 280 ( 1 9 5 3 ) : J . A m . Oil C h e m i s t s ' Sot., 80, 326 ( 1 9 5 3 ) ; J . A m . Oil C h e m i s t s ' Sot., 31, 85 ( 1 9 5 4 ) . 5. V a n d e r "Wal, R. J., J . A m . Oil Chemists' Sot., 37, 18 ( ] 9 6 0 ) . 6. Y o u n ~ s , C. G., p a p e r p r e s e n t e d at the 5 1 s t a n n u a l md!etin~, A m e r i c a n Oil Chemists' Society, Dallas, Tex., A p r i l 4 - 6 , 1960. 7. D u t t o n , I t . J., Scholfield, C. R., and Mounts. T. L.. oal)er Ores e n t e d b e f o r e the D i v i s i o n of A g r i c u l t u r a l a n d Food C h e m i s t r y , A m e r i (.an C h e m i c a l Society Meeting, Cleveland. O., April 5 - 1 4 , 1960. 8. J o n e s , G. u a n d H a m m o n d , E. G., J . A m . Oil C h e m i s t s ' Soc.. in press.

Interesterification of Edible Fats
W. Q. B R A U N , Wilson and Company, Chicago, Illinois
T H E L A S T T E N Y E A R S , rearranged lard has become a v e r y i m p o r t a n t shortening ingredient. I t is p r e p a r e d f r o m n a t u r a l lard by redistributing the f a t t y acid radicals among the triglyceride molecules. That esters can exchange acid groups has been ]Known for almost one h u n d r e d years. I n 1865, Friedel and Crafts, of F r i e d e l - C r a f t s reactions fame, heated a m i x t u r e of a m y l acetate and ethyl benzoate at 300~ in a sealed tube. W h e n they analyzed the contents of the tube, they found ethyl acetate and a m y l benzoate as well as the original a m y l acetate and ethyl benzoate (1). This classical experiment was the first demonstration of interesterification~ the exchange of aeyl and alkyl groups between esters: R C O O R ' + R " C 0 0 R ' " ~ R C O O W " -4- R " C O O R ' URING


water. F r e e alcohol and acid are formed. 3. Saponification is the splitting of an ester by alkali. Soap and alcohol are formed. 4. Alcoholysis is a displacement of the alcohol radical o f an ester by another alcohol. 5. Acidolysis is a displacement of the acid radical of an ester b y another acid.

Interesterification of Triglycerides
F a t s have three ester linkages per molecule. Therefore the interchange possibilities are many. Not only can the f a t t y acid groups exchange positions within the molecule, but each f a t t y acid can also trade places with a n y one of three f a t t y acids in another molecule:

Interesterification within Molecules CH2OCOR' CH2OCOR"


I n this discussion the t e r m interesterification will r e f e r only to an exchange of acid or alcohol groups by esters. This is sometimes also called ester interchange or transesterification. Although we are p r i m a r ily concerned with the interesterifieation of edible fats, it will be necessary to refer to a n u m b e r of related ester reactions f r o m time to time. 1. Esterificatio~ is the f o r m a t i o n of an ester and w a t e r f r o m an alcohol and acid. 2. Hydrolysis is the splitting of an ester b y





I t


Interesterification between Molecules
CHOCOR,' + CHOCOR" ~-I t Ctt~OCOI~' C H ~ O C O R "







To appreciate w h y lard lends itself so well to interesterifieation.A. The American Meat I n s t i t u t e played a m a j o r role in this. Nevertheless the contributions of Normann.50 _ 12. Interesterifieation had been used to make confectionery fats f r o m mixtures of coconut oil a n d vegetable fats (10). c. they interesterificd a v a r i e t y of f a t lnixtures. and hydrides are all very effective low-tern- . first disclosed by E c k e y (16).NOVEMBER. I n 1935. etc. its inability to incorporate enougb air into cake batters while these are being mixed. it is necessary to consider two characteristics of n a t u r a l lard.5% 10. Low-Temperature Interesterification Two technological advances finally triggered commercial lard interesterification.oleie 50. that is. N o r m a n n (5.6) and Van l~oon (7). were the pioneers in this field.C__mole% 10. W o r k i n g independently. 50 mole % of tristearin were intereslerified with 50 mole % of t r i o M n the equilibrium mixture should have the followinz ('mnposition: 50. is based on the melting point of the t r i s a t u r a t e d glycerides (11). The well-known B5mer test for lard adulteration.5% lO. instead of the more nmnerous alpha positions. B. and at 50~ they were so active that equilibrium was reached within 30 minutes (17). etc. Althongh randomized lard still contains a p p r o x i m a t e l y 25% disatnrated glyeerides. less t h a n 5% are of the beta pabnito type. cadmium.onsist of glycerides which were not present in the original mixture.oOCOR" Interesterificated fats were not an immediate commercial success.000 I t will be noted t h a t 75% of the imeresterificd fat: would .stearic --olcic steari(.~terification.000 A. -. u n a t t r a c t i v e appearance. This differentiates it f r o m directed interesterification which will be discussed later. beef f a t and coconut oil. The resultant product was comparable to good quality vegetable fat shortenings in appearance and creaming quality. The other is its poor creaming quality. b. sulfonic acids.oleic -. [t has been known for years that lard glycerides have unique properties. Interesterification in the liquid phase is often called r a n d o m interesterification.stearic -. coarse crystal s t r u c t u r e which gives it a dull. A. it was not applied to fats until the 1920's.50. glyceridea-a-a=l• glyceridea-a-b glyceridea-b-c -=3X =6• A. One of these is a large. Bailey (14) associated the crystallization habits of lard with its poor creaming power and a p p a r e n t l y was the first to use interestcrifieation for the purpose of b r e a k i n g up the responsible glyceride eonfignration. This leads to poor texture and volume in the baked cakes. beef fat and t r i b u t y r i n to simulate butter. tristearin and triacetin.3). One of these was the development and a p p r o v a l of effective antioxidants.9) studied the theoretical aspects of the reaction. zinc and their compounds. The p r o d u c t was handieapped b y the absenee of natural antioxidants like the toeophorols whieh occur in cottonseed and soybean oil but not in lard. V a n Loon.OO0 mole% Lard Interesterification Large-scale interesterification is a postwar development p r i m a r i l y concerned with lard. ~mall amonnts of interesterified lard were produced in the late 1920's (15).stearic = 1 • -. C. A m o n g those found to be effective were tin. The glyeeride composition of r a n d o m l y interesterified fats can be calculated with the following statistical formulas if the f a t t y acid compositions are known(4) : W h e r e A. m o l e % 10. The late A.~OCOR' CHOCOR" + CHOOOR' Ctt~OCOR' I I I I CH.B.A.t e m p e r a t u r e interesterifieation. Sodium and potassium and their lower aleoholates.000 If.50. Although interesterifieation has been known for nearly a century. Hilditch (12) was able to show t h a t most of the palmitic acid in lard is attached at the beta position of the glyceride molecule.. two E u r o p e a n industrial fats and oils chemists.5% 10. f'or example. and compounds of alkaline earth metals and alkali metals.olcic oMc . lead.5% 10. devised in 1913. D i s a t u r a t e d beta palmito stearo-glyeerides are now reeogMzed as the cause of the coarse crystal structure of lard.3 • 50.O0(I =. This of course is an extreme case. E. Since reaction rates increase with temperature. are the molar percentages of f a t t y acids a. Most n a t u r a l fats are closer to random distribution and therefore undergo less change d u r i n g interc. and Griin provided an excellent s t a r t i n g point for those who did later research in this field. The other was the discovery of l o w .50 = 3 • -. Griin (8.000 = 1 • 50.B. Included with the latter were the alkali metal alcoholates which are used extensively today. amides.oleie . I t is assumed t h a t the f a t t y acids regroup themselves among the glyceride molecules according to chance. IO.0(}(} stearic -. fat interesterifieation was originally carried out at temperatures as high as practicable. Some of his results were in good agreement wilh the theory of random arrangement.37. 1960 BRAUN: INTERESTERIF1CATIONOF EDIBLE 599 CH~OCOW' CH. Their search for catalytic materials was extensive. including positional isomers.50 stearic .12. were formed. A m o n g these were stearins and vegetable oils. Triglyceride analyses are not very exact. E v e n so it took hours to arrive at a random equilibrium at 200~ Eekey however was t r y i n g to direct the reaction a w a y from its usual randoln endpoint.50. but this a p p a r e n t l y was not a sizeable operation. I n the course of his work he forum that under the p r o p e r conditions some catalysts were still active below the melting point of fat. A f t e r N o r m a n n disclosed that fats can be interesterified.A. The rcaetion was carried on| in the absetme of air at about 200~ with sodium hydroxide plus glycerol as catalyst. This work has been eonfirmed with more refined teehniques (13). but they do indicate a completely randonl a r r a n g e m e n t at reaction equilibrium (2.50 _ 37. H i s analyses of interesterified mixt u r e s s h o w e d t h a t all of the t h e o r e t i c a l l y p o s s i b l e compounds.50.

A f t e r the f a t has been interesterified. Howew. N o n r a n d o m interesterification has m a n y possibilities. Therefore cooling curves or single point dilatometrie measurements are generally used. the methyl esters must be removed. and other extraneous materials which will react with sodium methoxide. the catalyst is destroyed. the catalyst m a y be inactivated either with water or acid. The alkaline water also removes most of the color bodies formed d u r i n g the reaction. more catalyst is required. Special precautions are necessary when the alkali metals and hydrides arc used. I t has a number of advantages over the old high-temperature methods. and the d a n g e r of thermal damage to the f a t is greatly reduced. I t seems likely that these materials are actually precursors of the real catalyst.r high. it m a y f o r m nitrogen oxides which can detonate spontaneously (18).26). 37 p e r a t u r e catalysts. After the catalyst has been destroyed. ICIonoglycerides lV[onoglycerides m a y be p r e p a r e d either by the esterification of f a t t y acids with glycerol or the glycerolysis of triglycerides. This removes them f r o m the reaction and upsets the equilibrium of the liquid phase. which contains 25% s a t u r a t e d acids. . These served as nuclei for the f o r m a t i o n of more of the same crystals (25. I n the t e m p e r a t u r e range of 60 to 85~ the reaction reaches equilibrium within t h i r t y minutes a f t e r the color change occurs. The course of the reaction can be followed b y cloud-point determinations. Directed interesterification is relatively slow because of the lower t e m p e r a t u r e s used and the time required for crystallization. L a r d which has been filtered and v a c u u m dried but not refined requires about 0. p r e p a r a t i o n of lard shortening. According to Eckey. This coating effect has been overcome by the use of a dispersion of liquid sodium-potassium alloy. and sodium methoxide is the most p o p u l a r of these. the p r i m a r y application at the present time is concerned witb be carried out in ope. and creaming properties if they are continued nntil a r a n d o m equilibrium exists. The resultant f a t also has a better plastic range because it is lower in disaturated mono-unsaturated glycerides (27). r a n d o m endpoint if the f a t is allowed to crystallize d u r i n g the reaction. This color p r o b a b l y is due to the sodium-glyceride compound believed to be the true catalyst. P a t e n t s have also been g r a n t e d for its use in p r e p a r ing other shortenings (21. which in t u r n forms more trisaturates in an effort to regain equilibrium.24). confectionery fats. I f the fat is to be used as a food. Sodium methoxide is easier to handle. There have been instances where open containers have ignited in moist atmospheres. The cooling curve of lard has a characteristic h u m p which disappears a f t e r interesterification. The catalyst concentration should be kept as low as practicable to p r e v e n t excessive losses resulting f r o m saponification by the sodium radical and m e t h y l ester formation by the methyl radical.600 T~E JOURNAL OF Tile AMERICAN OIL CHEMISTS' SOCIETY VOL. free f a t t y acids. i kettles. The f a t should take on a reddish brown hue a few minutes a f t e r the catalyst has been added.. as well as confectionery fats which contain coconut oil (23. it would have contained only about 1. IIowever as with r a n d o m interesterification. crystal structure. The t r i s a t u r a t e d glycerides crystallize first. The alcoholates are the most convenient to use. Solid catalysts like sodium metal and sodium methoxide tend to become coated. Eckey was able to get 19% t r i s a t u r a t e d glycerides f r o m cottonseed oil. but its use also requires care because the reaction between water and sodium methoxide is very exothermic. W i t h m a n y fats either the melting point or cloud point can be used to follow the reaction. These liquid spherical particles slough off the coating as it is formed. W i t h lard these determinations are of no value since interesterifieation changes the melting point of lard only slightly. The reaction ~. and m a r g a r i n e s (16)' as well as the removal of saturated f a t t y acids from oils. W h e n sodium amide ages. E c k e y (17) f o u n d t h a t interesterification can be directed away f r o m its usually I I --I CH2OH mono- I Both alcoholysis and interesterification occur.5% t r i s a t u r a t e d glycerides and more t h a n 40% disaturated mono-unsaturated glycerides. W h e n w a t e r is used the saponified acids can be removed with conventional refining equipment. conventional shortening. I f it does not appear. I f this f a t had been r a n d o m l y interesterified. Consequently it has to he firmed u p with about 10% of t r i s a t u r a t e d glyeerides.and low-temperature interesterifications have the same effect on glyceride composition. and as a result the f a t is always exposed to active catalyst (27). equilibrium is reached more quickly.20% sodium methoxide. F a t s which are to be interesterified should be low in moisture. peroxides. This is done while the f a t is still in a semisolid state because a n y rise in temp e r a t u r e while the catalyst is active will reverse the reaction. W a t e r plus carbon dioxide has been recommended to reduce saponification (27). compounds of sodium with nmterials much more acidic t h a n alcohol will not bring about interesterification at low temperatures. which slows down the reaction still more. which p r o b a b l y is a compound of the alkali metal and a glyceride. A m o n g them are the p r e p a r a t i o n of shortenings. because hydrogen is liberated. W h e n the desired a m o u n t of trisaturates has been formed. Directed interesterification has also been used to separate d i s a t u r a t e d mono-unsaturated glycerides. To accomplish this. The use of sodium methoxide for low-temperature lard interesterification has been patented (19. W i t h directed interesterifieation the t r i s a t n r a t e d glycerides are one of the reaction products.20). CH2OH CHOH CH20H glycerol CH2OCOR CH2OCOR CH2OCOR + CHOCOR CH2OH diglyceride At § C H O C O R __~ C H O H CH2OCOR tri- Directed Interesterification A r a n d o m a r r a n g e m e n t of f a t t y acids is not always the most desirable one. Glycerolysis is generally used for the p r e p a r a t i o n of food grade emulsifiers. catalyst was added to chilled oils in which most of the crystals were disaturated monou n s a t u r a t e d glycerides. These come out readily d u r i n g steam deodorization. This continues until most of the saturated acids have been precipitated.22). the lard is sent t h r o u g h a series of heat exchangers to lower the temp e r a t u r e gradually. R a n d o m l y r e a r r a n g e d lard is softer and has a lower melting point t h a . A f t e r the catalyst has been added. the f a t is melted so t h a t the soaps can be removed.

499 (1952). and Lutton.693 (1941). J. See. to indicate the limitations in the data. S. Ir O. S. Interesterifieation and allied ester reactions are also (19553. Griln. U. E. The distilled products have a monoglyeeride content of 90% or more.531-2... A. K.. American Meat Institute (1953). " I n d u s t r i a l Oil and Fat Products. p. W. Vol. E. Eekey.. 600. J. Bailey. U. S. W. E. J. A.C.. G.065. ~6. Interscience Publishers. medical records from the United States are not directly comparable to those from I n d i a where few people ever see a doctor.. E.916 (1926). and I~eGee.442. U. K. S. Ihlwew~r. T. Bailey. Pormo. 559 (1913). 90 ( 1 9 4 6 ) . M. Gooding. C.378. 31. F o r example. E. Norris. Desnuelle. because of its limited solubility. p. 681. Mutual solvents have been proposed to increase the monoglyceride content (29). New York ( 1 9 5 1 ) . The reaction should be halted before a n y cooling occurs. 40. Eckey. Nahr. F. and Crafts. but most concentrates are made by molecularly distilling mono.. these p r o g r a m s arc of vital concern in ternls of the health of the nation. and Mattil.wes between experimental animals and h m n a n beings in the ways iu which blood vessels react to the (tietary factors presumed to lead to atheroselerosis and heart disease. 3. F i r s t of all.and diglyeeride mixtures. L. New York (1945). 26.. Eckey. 1183 (1948). 5. P a t e n t 2.. Patent 2. Wille.783. Phosphoric acid has been recommended for destroying the alkaline catalyst (30). 2. Genussm. Dutch P a t e n t 16. T. mono-. Bioehem.742 (1950). 11.. 4. New York (1954). of which fats are one class. 7. chem. to (tarry into our tissues the fat-soluble vitamins which are so imporlarlt to health. Normann. 14. S. A.442.625.." Interscience Publishers Inc. U. 28. These applications were reviewed by F o r m o in the 1954 A... 2. I t ranges f r o m 22. Patent 2. E. E. Umschau 80.855. S..949 (1943).807 (1946).538 (1948). Soc.158 24. in addition. 30. Illinois [TH[N TIlE PAST FEW Yb'ARS all of us in the fats and oils i n d u s t r y have become acutely aware of the research indicating a relationship between heart disease and dietary fats.215 (1925).. 834. Oil (!hem. 1. A. n. otherwise glycerol will d r o p out of solution and reduce the yield of monoglyeerides. RE~'ERENCES 1. Ad. BSmer. RATHMANN..311 (1958). there is no doubt that fats are excellent foods.703 (1927). g. The product has a r a n d o m distribution of the r e m a i n i n g acids. 1960 BRAUN: I N T E R E S T E R I F I C A T I O N OF E D I B L E 601 equilibrium there is an essentially r a n d o m m i x t u r e of glycerol. 15.513 (1932). E. 12. Griin. Vienna (1936). p... E. " I n d u s t r i a l Oil and Fat Products. Pat. Patent 2. 186 ( 1 9 5 3 ) . Patent 2.006. and Van Akkeren. and Ott. Proceedings of the Fifth Research Conference. W. 827 (1925). Interscience Publishers Inc. [... P a t e n t 2..378. Bailey..151 (1957).536-7 (1948). and Eng. Kronig.251. 10. M:. George M. Am.521. Dietary Fat and Heart Disease DOROTHY M..5% at 200~ to 40% at 250~ (28).. J. 21. Argo. which contain low molecular weight acids. 23. The usual high-temperature interesterification catalysts are effective. W. Statistics are being amassed in all p a r t s of the world on local incidences of various diseases. U. A. Friedel.. Ad. 99 ( 1 9 3 5 ) . They are highly concentrated sources of energy and contribute much to the enjoyment we get out of our meals. ]~]ckey. P. U. 17. A. Vol.. Coehran. R. There are v e r y serious limitations to the accuracy of such data and consequently they m u s t be i n t e r p r e t e d with caution. C." 2nd e d . 285. 207 ( 1 8 6 5 ) .535 (1948). and Clark. U.315 (1951). Patent 2.. Oue of the bits of evidence linking heart disease with dietary fats has come fronl population and epidemiclerical studies. Thus. 301. U. Paterson. 33. and Nelson. 2. W. "Chemic und Technolog-ie der Fette..332 (1939). Most commercial monoglyceride mixtures are p r e p a r e d at about 200~ with sodium hydroxide as catalyst and contain 40 to 45% a l p h a monoglycerides plus about 4% beta monoglycerides. W. 8. U. and to discuss the interpretations and hypotheses on which c u r r e n t clinical research is based. Abbott. In addition. Oil and Soap ~8. See. L.309. Quimby. 30. G. Vr U. S. J. the foods people eat. U.182. 11. My purposes in the present review are to outline the nature of the evidence now available.S. E. German P a t e n t 417. and Bailey.. and StMnsby. 13. P. Ztschr. Barsky. F. P a t e n t 2. S. W...310 (1958). Hilditeh. 34..571. J. W. Lr. S. 25. Feuge.. S. Besides the potential effects on our markets. 18. E... Lipid materials. Encyclopedia of Chemical Technology. British Patent 574.. R. 1. S. S. tIawley. Nelson. Patent 2.'ells and life as we know it would be impossible without these f a t t y materials. A. H. and Kuhhnann.483 (1953). 16. Chem. Patent 2. p. S.. S. Chr. Patent 2.. Short Course (34). and Naudet. Patent 2.726. pp. and l~iehardson.. 32. W. and the conditions u n d e r which they live. S. there is no doubt that fats are excellent foods.. Z.. R. The reaction can be carried out u n d e r reduced pressure in a vessel equipped with a fractionating column through which the lower molecular weight acids are continuously removed as they are freed (32).. A similar result can be obtained by using monoesters instead of the free acids (32.. Untersuch. reliable d i e t a r y histories are difficult to obtain so the information available generally relates to the quantities of food available in the mar- . A. see.. H. M. W. and ourselves. Am. The reaction cannot be driven to completion by adding an excess of glycerol. Mattil. M.873. J. A. K.O. 259 (1946). 18. S.. U.. 22.. Xg. 9. U. Reissue 23.442.NOVEMBER. Therefore available data are inconclusive to the extent that they provide at least some degree of s u p p c r t for each of several points of view. di-. 6. Chem.. U.. Am. W.607 (1945).520 (1936). Moffett Research Laboratories. F. Eckey. m a y be modified by displacing the short chain acids with longer chain acids (31). 33. This is a controversial tel)it and an a(qive area of research. Cochran.. M. Gil Chem. and Hohnan. Corn Products Company. Ind. 29. 12. O. Oil Chem. chim. Annalen 183. C. our families. S. C. There are i m p o r t a n t differe. and triglycerides. Acidolysis plus Interesterification F a t s like coconut oil. Van Loon.. V a n d e r Wal. 20. angew. F. Bull. 29 ( 1 9 5 6 ) . As a m a t t e r of fact a certain amount of fat is necessary to provide the essential f a t t y acids which W our bodies are unable to synthesize and. 88. 250 (1923).442. 19. Inc. used quite extensively in the m a n u f a c t u r e of paints and plasticizers.. 289 (1946)." Julius Springer. P a t e n t 2.33).855. 31. D. Steffen. are importarlt constituents of all living (. Eckey. L.. P~tent 2. D. recent clinical studies have clearly shown that there arc i m p o r t a n t differences in the way in which our bodies metabolize fats f r o m different sources and that these differences m a y be associated with the development of coronary heart disease. British P a t e n t 249. 548 (195:(). 1~. \V.. Normann. 27. S. M. 29. W. J. Limprich. J. Oil ~r Sea0 23. Patent 2. R. A.