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The solubility of dotricontane and tetracosane in cis and trans decaphydronaphthalene Yip, Sun Wing 1941

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THE SOLUBILITY OF DOTRIAOONTANE AND TETRACOSANE IN CIS AND TRANS DECAHYDRONAPHTHALENE "by Sun Wing T i p A Thesis submitted i n P a r t i a l F u l f i l m e n t of The Requirements f o r the Degree of MASTER OF APPLIED SCIENCE i n the Department of CHEMISTRY The U n i v e r s i t y of B r i t i s h Columbia A p r i l , 1941. ACKPTOWLEDGEMMT The w r i t e r wishes to express M s app r e c i a t i o n and thanks to Dr. W. P. Seyer f o r h i s valuable and h e l p f u l suggestions given to him throughout t h i s research. CONTENTS Page X xntro due t ion • &«««.•»•« *•»*•*••••«•• 1 I I M a t e r i a l s used and I t s Preparation »«»»»*»«•»»•» 4 2. • 0xs Decalxn «.«.«•«•.•••..••«...»•«»«»»..» 4 2• Dotrxacontane »•»».««•«.»«««»«*.«•«««««««. 5 3. Determination of M e l t i n g Point ........... 7 I I I Apparatus used and Experimental Procedure ...... 9 1« C a p i l l a r y Method ............. 9 2* 33\il"b l^Eetlxod. 10 IV Resixlt s •«*••»•»*•«»••»*• « * « » « a » » » » o f t » * f t » * & 12 ¥ Treatment of Results ................... . • 17 71 Conclusion .............. 19 Sifrlio^rapii^r • «*•••• & «®*©6«©«*«*»«a&*»» SO j^ia^rams •«••*«••«• © • • *«• «.«*«&©•*» M e l t i n g Point Apparatus ..................... 7a Graphs 1. Weight percent D i c e t y l vs. Temperature ... 2. Mol percent D i c e t y l v s . Temperature ...... 3. Mol percent D i c e t y l i n various solvents vs« Temperature ...*«••.»*«•»............. 4. Log Mol f r a c t i o n D i c e t y l vs. R e c i p r o c a l of Temperature The S o l u b i l i t y of Dotriaoontane i n Cis Decalin I I n t r o d u c t i o n A considerable amount of information regarding the mutual s o l u b i l i t i e s of hydrocarbons are a v a i l a b l e i n the l i t e r a t u r e . About t h i r t y years ago Holde found that l i g h t hydrocarbons when added to petroleum caused the asphalt • • 1 p o r t i o n to be p r e c i p i t a t e d . In 1932 P i l a t and Godlewicz g extended t h i s idea and repeating the work of K l i n g treated a P o l i s h petroleum w i t h propane and p r e c i p i t a t e d most of the asphalt i n the crude. The remainder of the asphalt was p r e c i p i t a t e d by u s i n g methane at a pressure of 30 atmospheres. This work es t a b l i s h e d the f a c t that mutual s o l u b i l i t y of hydrocarbons was governed l a r g e l y by the molecular weights of s o l u t e and solvent. These f a c t s are very valuable to the o i l companies and already extensive use has been made by them i n i s o l a t i n g and p u r i f y i n g c e r t a i n petroleum f r a c t i o n s by u t i l i z i n g solvents of various s e l e c t i v e powers. In s p i t e of a l l t h i s information. , very l i t t l e was s t i l l known of the quantitative, nature concerning the mutual s o l u b i l i t i e s of hydrocarbons* 3 In 1936 Dr. Seyer and Fordyce i n i t i a t e d the study of the systems of d i c e t y l and butane and d i c e t y l and propane to provide q u a n t i t a t i v e data on the mutual s o l u b i l i t i e s of hydrocarbons. They found that the mutual s o l u b i l i t y : of hydrocarbons i s a f u n c t i o n of t h e i r molecular weights* Also from t h e i r curves of concentrations i n mole percent against the f r e e z i n g point temperatures they found that i n the neighborhood of 55°G there i s a change i n the curvature of the curve. From t h i s point downward s o l u b i l i t y changes r a p i d l y w i t h the temperature, i n d i c a t i n g the occurrence of two forms of d i c e t y l * Evidence f o r the existence of two forms of d i c e t y l was l a t e r found by measuring the r e f r a c t i v e index at various temperatures below i t s melting point. The t r a n s i t i o n point i s about 55°C. The f o l l o w i n g year Dr. Seyer 4 extended t h i s i n v e s t i g a t i o n by obtaining f r e e z i n g point data of s i x separate systems of d i c e t y l with some low molecular weight hydrocarbons. The hydrocarbons used were as f o l l o w s : dodecane, decane, octane, hexane, cyclohexane and benzene. From the curves of mole concentration against temperature f o r each system, there i s a tendency f o r a l l the curves to c o i n c i d e from the melting point of d i c e t y l on, u n t i l the concentration of t h i s substance f a l l s to about 40 mole percent, then the solute appears to exert i t s i n f l u e n c e i n determining the shape of the f r e e z i n g point curve. These systems also showed no e u t e c t i c point or, i f such a point e x i s t s , i t would l i e very close to the f r e e z i n g point of the solvent. Since the study of decahydronaphthalene or d e c a l i n i s of great t h e o r e t i c a l i n t e r e s t mainly because of i t s two isomers trans and c i s , i t i s intended to determine i n t h i s research the mutual s o l u b i l i t y of d i c e t y l i n c i s d e c a l i n . The primary object i s to f i n d whether a saturated d i c y l i c r i n g compound would have any serious a f f e c t on the s o l u b i l i t y of d i o e t y l , secondly, to see whether or not a e u t e c t i c point i s formed. Cis d e c a l i n was used because of i t s abnormal behavior as determined from the various p h y s i c a l properties such as v i s c o s i t y , vapour pressure and r e f r a c t i v e index measurements, whereas the trans d e c a l i n behaves quite r e g u l a r l y . Further i t i s hoped that the data obtained may 5 be used to check the equation of HiIdebrand . I I M a t e r i a l s used and I t s Preparation 1. D e c a l i n The deoalin was brought from Eastman Kodak Company which was about 50 percent t r a n s . The composition of the crude d e c a l i n i s found to vary. These v a r i a t i o n s are probably due to v a r i a t i o n s i n the hydrogenation process by which the d e c a l i n i s manufactured. The c i s d e c a l i n was separated from the trans by vacuum d i s t i l l a t i o n at a pressure of 8 mm. of Hg. A charge of about 2000 cc. of the crude d e c a l i n was introduced i n the s t i l l . The trans having a lower b o i l i n g point comes o f f i n the f i r s t f r a c t i o n s . The r e f r a c t i v e index of the various f r a c t i o n s were taken and those which contain high c i s were mixed together and the whole rerun f o r pure c i s . For f u r t h e r d e t a i l s and d e s c r i p t i o n of the d i s t i l l a t i o n apparatus r e f e r to the f o l l o w i n g theses: ' K i r k BASc Thesis 1935 Walker MASe Thesis 1937 Davenport MASc Thesis 1939 Then the high c i s f r a c t i o n s are r e c r y s t a l l i z e d f o r pure c i s . This i s done i n a p a r t i a l l y - e v a c u a t e d double-wall g l a s s f l a s k , u sing a platinum r e s i s t a n c e thermometer. By c o o l i n g a mixture high i n c i s , s o l i d c i s i s formed l e a v i n g the mother l i q u i d r e l a t i v e l y higher i n trans, t h i s i s of course assuming a binary system where there i s a e u t e c t i c p o i n t . The l i q u i d i s poured o f f l e a v i n g pure c i s w i t h entrained trans. This procedure was repeated u n t i l the 5 temperature of c i s formation remains constant f o r quite awhile. This temperature was considered as the f r e e z i n g point of pure c i s d e c a l i n . To avoid supercooling, the sample was innoculated with^frozen c i s sample. The f i n a l f r e e z i n g point of the c i s d e c a l i n was taken as -43.22°C and was considered quite pure. 2. Dotriacontane or D i c e t y l The normal s t r a i g h t chain hydrocarbon d i c e t y l used i n t h i s work was synthesized from c e t y l i odide by the method 6 of S o r a b j i . The c e t y l i o d i d e was prepared from C P . c e t y l 7 al c o h o l according to the procedure of K r a f f t i n which hydrogen iodide.was passed repeatedly i n t o melted c e t y l a l c o h o l . The hydrogen iodide was prepared by the a c t i o n of water on phosphorous t r i - i o d i d e , the l a t t e r formed from white phosphorous and c r y s t a l s of i o d i n e . The hydrogen iodide gas l i b e r a t e d was passed through a red phosphorous absorption tower to remove as much f r e e i o d i n e as p o s s i b l e and f i n a l l y i n t o l i q u i d c e t y l a l c o h o l u n t i l the l a t t e r was completely saturated. The c e t y l i odide i s formed according to the r e a c t i o n c i 6 V H + H I 0 i 6 W + H2° The c e t y l a l c o h o l was then p u r i f i e d to some extent by washing w i t h d i s t i l l e d water repeatedly, using a f r e s h p o r t i o n each time and separating a f t e r each washing i n a separating funnel* The product was then r e o r y s t a l l i z e d from e t h y l a l c o h o l removing the l a s t traces of i o d i n e . The c e t y l iodide was then weighed and dissolved i n ether and an excess amount of sodium^neeessary to remove the iodine was added. Since the procedure of Sorab-ji ( l o c . e i t ) was followed i n t h i s part of the synthesis, there i s no need to repeat i t here. The f o l l o w i n g r e a c t i o n seems to take place: 2 G 1 6 H 3 3 r -+ 2 3* a G32 H66 + M The crude d i c e t y l was p u r i f i e d by repeated c r y s t a l -l i z a t i o n from g l a c i a l a c e t i c a c i d , followed by r e e r y s t a l l i z a t i o n from ether. For the f i n a l p u r i f i c a t i o n only g l a c i a l a c e t i c was used. The bulk of the a c i d was removed by siphoning and the r e s t by f i l t e r i n g the c r y s t a l s and a c i d through a Buchner funnel using s u c t i o n . To remove the l a s t trace of a c i d , d i s t i l l e d water was run repeatedly through the d i c e t y l c r y s t a l s u s i n g f r e s h portions each time; about 5 l i t e r s i n a l l were used. This removed a l l the a c i d , as water and g l a c i a l a c e t i c a c i d are exceedingly s o l u b l e . Then the d i c e t y l c r y s t a l s were d r i e d i n a vacuum desiccator f o r a few days, a f t e r which a melting point determination was made. The r e c r y s t a l l i z a t i o n was repeated u n t i l a constant melting point was obtained. F i f t e e n r e c r y s t a l l i z a t i o n s were made a f t e r the second melting point determinations and no increase i n melting point of the product was noted; The d i c e t y l was considered pure. 7 3» Determination of M e l t i n g Point The melting point of a s o l i d substance which does not sublime or decompose on heating to i t s melting point i s one of the best c r i t e r i a of p u r i t y . Hence t h i s method was used to determine the p u r i t y of the d i c e t y l . The procedure 8 used f o l l o w s that of P i p e r , the apparatus c o n s i s t i n g of a o. glass bulb w i t l u s i d e arm,holding about 150-200 cc. of concentrated sulphuric a c i d . I t i s f i t t e d w i t h a glass tube wi t h a c a l i b r a t e d thermometer graduated i n 0.1°C i n s i d e i t . The diagram i n the next page i s perhaps s e l f explanatory. The bulb i s not s t i r r e d and by using a small flame and r e g u l a t i n g the r a t e of heating, i t i s p o s s i b l e w i t h care to repeat the melting points w i t h i n an accuracy of 0.1°C. The temperature at which the substance shows the f i r s t sign of melting i s taken as the melting point of the dicetyi. The f i n a l m elting point of the d i c e t y l was 69.55°C as measured by the c a l i b r a t e d mercury thermometer, i n c l u d i n g stem c o r r e c t i o n . This agrees w i t h that of Piper's ( l o c . c i t ) value 69.5°C to 69.7°C, yet d i f f e r i n g from the value of other 9 i n v e s t i g a t o r s . Hildebrand and Wachter pointed out that the melting point of d i c e t y l should be approximately 70°c and they obtained a melting point of 70°C. I f t h i s i s c o r r e c t , then the d i c e t y l must have contained some of the next lower hydrocarbon* i e . C„.,H- Since a f t e r f i f t e e n c r y s t a l l i z a t i o n s ox 64 the d i c e t y l showed no increase i n the melting p o i n t , i t was considered pure. 8 - , I t i s i n t e r e s t i n g to note that the ra t e of heating a f f e c t s the melting point as determined by t h i s method. Time must be allowed f o r the t r a n s f e r of heat through the w a l l of the c a p i l l a r y tube. Because the observations of thermometer and : sample are not simultaneous, the r a t e of heating must be slow enough to make the e r r o r from t h i s source n e g l i g i b l e . o o I t • -is found that the rate of heating of 0.1 — ,0.2 per minute i n the v i c i n i t y of the melting point gives very s a t i s f a c t o r y r e s u l t s . 9 I I I , Apparatus used and Experimental Procedure 1. C a p i l l a r y Method In determining the s o l u b i l i t y of the system d i c e t y l and c i s d e c a l i n by melting and f r e e z i n g points, the c a p i l l a r y tube method \ i s used. This method i s by f a r the most common and convenient of a l l . I t has the f u r t h e r advantage of r e q u i r i n g very small amounts of m a t e r i a l . However, t h i s i s not by any means the best method to be used and great accuracy must not be expected, though extreme care was taken at a l l times during the readings. The apparatus consisted of a side arm f l a s k p r e v i o u s l y described. Thin-walled c a p i l l a r i e s about 1 mm. i n diameter were made by heating and drawing out tubing that has pr e v i o u s l y been cleaned and d r i e d . About 0.5 gm. of d i c e t y l was weighed out ac c u r a t e l y i n a "weighing b o t t l e and enough c i s d e c a l i n was added to give a one percent solution., The mixture was then heated u n t i l the whole melts and the s o l u t i o n was s t i r r e d and shaken to promote mixing. When complete mixing was assured, the l i q u i d i s introduced i n t o weighed c a p i l l a r y tubes by c a p i l l a r y a c t i o n and the content i n the b o t t l e was desixsated f o r weighing. Both the c a p i l l a r i e s and the mixture i n the b o t t l e were weighed a c c u r a t e l y to get the cor r e c t weight of the mixture. The weight of the hydrocarbon was taken . to be constant, assuming, no evaporation, and by sub t r a c t i o n from the t o t a l weight, we get the weight of c i s d e c a l i n added, from which the weight percent of d i c e t y l was 10 c a l c u l a t e d . The length of the s o l i d i n the tube a/as about 2 mm. Then the tube was sealed and the mixture was shaken down to the end of the tube* The c a p i l l a r y tube <»as then immersed i n t o the bath with the sample adjacent to the thermometer and the whole heated u n t i l melting occurred. The rate of heating was regulated so that the temperature r i s e M S l e s s than 0.2° per minute i n the v i c i n i t y of the melting p o i n t . The temperature where a l l the c r y s t a l s disappear was noted. The bath was cooled u n t i l the white c r y s t a l s of d i c e t y l appeared, upon which the bath was heated again slowly u n t i l the l a s t trace of c r y s t a l s i n the tube j u s t disappeared. The temperature at t h i s point was taken as the f r e e z i n g point of the mixture. The procedure was repeated w i t h two other c a p i l l a r i e s of the same mixture u n t i l the readings agreed with one another. The point of disappearance of the c r y s t a l s was f a i r l y sharp. More c i s d e c a l i n was added and the procedure repeated as above. 2. Bulb Method o For temperature readings below 30 0 the bulb method was used. Thick-walled uniform bulbs of 2 cm. diameter were blown of pyrex gla s s tube and sealed to about 9 cm. stems of 3 mm. tubing. The d i c e t y l was weighed i n a weighing b o t t l e and c i s d e c a l i n was added as before. A f t e r the mixing was complete, the s o l u t i o n was poured i n t o the bulb p r e v i o u s l y cleaned by means of a fine-drawn glass funnel. The content i n the bulb was frozen and the. end was sealed o f f . 11 For more, accurate determinations the frozen bulb should be evacuated so that, upon melting, the hydrocarbons would be under t h e i r own vapour pressure. The bulb was then placed i n a water bath e l e c t r i c a l l y heated and mechanically s t i r r e d . The f r e e z i n g point was determined as before and appeared to be f a i r l y sharp. For readings between zero and 10°C, an acetone bath was used i n a p a r t i a l l y evacuated dewar f l a s k . Dry i c e was added to lower the temperature of the bath. Temperature readings were taken by a platinum r e s i s t a n c e thermometer and no c o r r e c t i o n was needed. 12 IT Results Table I . Wt. of Wt. of . Wt. Percent Mol. Percent Freezing P t . D i c e t y l C i s Decalin of D i c e t y l of D i c e t y l o c ( g m s v ) ( - g m s v ) " ' 100.0 100.0 69.55 0.4301 0.0062 98.58 95.51 68.69 0.4286 0.0218 95.16 85.77 67.68 0.4276 0.0373 91.98 77.85 66.58 0.4266 0.0452 90.42 74.32 66.08 0.4256 0.0686 86.12 65.54 64.40 0.4246 0.1031 80.47 55.80 62.80 0.4252 0.1097 79.49 ' 54.25 62.41 0.4241 0.1419 74.93 47.82 61.06 0.4230 0.2565 62.25 33.58 56.68 0.4227 0.4207 50.12 52.21 0.4223 0.5850 41.92 18 »12 49.26 0.4209 0.9596 30.49 11» 8 5 44.05 0.4195 1.3196 24.12 8.83 41.20 0.4178 1.7050 19.68 6.98 39.21 0.0320 0.1497 17.61 6 • 15 38 . 52 0.4169 2.4231 14.68 5.01 36.80 0.4162 2.5860 13.86 4.70 36.16 13 gable I . (eont.) Wt. O f ) i e e t y l (gras*) . Wt. of Cis Decalin, Wt. Percent of D i c e t y l Mol. Percent of D i c e t y l Freezing P t . °C 0.4147 3.9917 9.41 3.08 32.95 0.3773 4.9830 7.04 2.26 30.55 0.0324 0*7201 . 4.31 1.36. 26.50 0.0306 0.8540 3.46 1.086 24.75 0,0141 0*5603 2.46 0.76 23.05 0.0119 0.7889 1.49 0.46 19.65 0.0104 1.0839 0.95 0.29 16.45 0.0161 3.0751 0.52 • 0.16 13.25 0.0112 11.3021 0.10 0*03 3.20 0.00 0.00 -41.22 Table I I . , Mol. Percent Freezing P t . Log,JST 1 v i n " of D i c e t y l : °c 1 0 ^ 100.0 69.55 95*51 68.69 85.77 67.68 77.85 66.58 74.32 66.08 65.54 64.40 55.80 62.80 54.25 62.41 47.82 61.06 33.58 56.68 23.55 52.21 18.12 49.26 11.85 44.05 8.83 41.20 6.98 39.21 6.15 38.52 5.01 36.80 4*70 36.16 1.98005 29.26 1.93334 29.35 1.89126 29.44 1.87111 29.49 1.81651 29.63 1.74663 29.77 1.73440 29*81 1.67961 29.93 1.52608 30.33 1.37199 30.74 1.25816 31.03 1.07372 31.36 0.94596 31.82 0.84386 32.02 0.78887 32.10 0.69984 32.27 0.67210 32.34 I 15 gable I I . . (cont.) Mol. Percent F r e e z i n g P t . log,nlS 1 of D i c e t y l o c i U « 3.08 32.95 0.48855 32.68 2.26 30.55 0.35411 32.94 1.36 26.50 0.13354 33.38 1.086 24.75 0.03583 33.58 0.76 23.05 -0.11919 33.77 0.46 19.65 -0.33724 34.17 0.29 16.45 -0.53760 34.54 0.16 13.25 -0.79588 34.93 0.03 3.20 -1.52288 36.20 0.00 -41.22 f a b l e I I I . ST L f Tm (°abs.) T (°abs.) 0! (°C) ; .4.-575. - ... . 3873.7 342.55 1.0 342.55 69.55 0.9 341.20 68.20 0.8 339.67 66.67 0.7 337.93 64.93 0*6 335.97 62.97 0*5 333.67 60.67 0.4 330.91 57.91 0.3 327.42 54.42 0.2 322.61 49.61 0.1 314.72 41.72 0.05 307.22 34.22 I f » 17.722 Kg Cal/mol. 17 V Treatment of Results The mole f r a c t i o n of d i c e t y l was computed f o r each reading. From,-results, curves were p l o t t e d as shown i n f i g u r e (1) and (2) r e s p e c t i v e l y . Figure (1) showed the f r e e z i n g point curve of d i c e t y l i n c i s d e c a l i n on.basis of weight percent d i c e t y l . The curve i n f i g u r e (2) was p l o t t e d on^mole percent d i c e t y l b a s i s . Also a p l o t was made of d i c e t y l i n cyclohexane i n f i g u r e (3), so as to compare w i t h the d i c e t y l - c i s d e c a l i n curve, the former r e s u l t s being taken from Dr. Seyer Ts experimental data ( l o c . c i t ) . I t w i l l be noted that the two curves almost run p a r a l l e l from 0.5 N down. Since the two samples of d i c e t y l used were of s l i g h t l y d i f f e r e n t melting point, i t i s r a t h e r hard to say whether the two t r a n s i t i o n p o i n t s are the same or not. The s o l u b i l i t y data was also p l o t t e d w i t h l o g - ^ of mole f r a c t i o n as ordinates and the r e c i p r o c a l of the absolute temperature as abscissa i n f i g u r e (4). Since the l a t e n t heat i s a f u n c t i o n of the temperature and assuming Raoult's law to hold over d i f f e r e n t i a l p o r t i o n s of the curves, i t i s p o s s i b l e to c a l c u l a t e the heats of f u s i o n at d i f f e r e n t temperature. Hildebrand ( l o c . c i t ) derived the f o l l o w i n g equation f o r the s o l u b i l i t y of s o l i d s . l o g * = ~ L f (| ~ | ) (1) 4.575 m where N - mole f r a c t i o n of solute s l a t e n t heat of f u s i o n T m - melting point of d i c e t y l °K 18 • \ Garner proposed the f o l l o w i n g equation f o r the l a t e n t heat of f u s i o n of the even p a r a f f i n hydrocarbons f o r the ex form: Q, x .6085n - 1.75 (2) where n = number of carbon atoms. For d i c e t y l Q, = 17.722 Kg Cal/mol. By s u b s t i t u t i n g t h i s value i n t o equation (1) and as s i g n i n g d i f f e r e n t value f o r N, the corresponding values f o r T i s c a l c u l a t e d ( T a b l e l l . ) . The. curve of N versus T gave us the "Ideal Curve" as shown i n graph 3. This was compared to the experimental curve. Garner, Bibber and King ( l o c . c i t ) pointed out that the higher hydrocarbons a l l e x i s t i n two enantiotropic forms cx and 6 • The & form i s stable at the melting point end changes i n t o the 6 form at temperatures a few degrees below the m e l t i n g point. The t r a n s i t i o n temperature of pure d i c e t y l was found to be 63.5°C. I t w i l l be noted that from f i g u r e (2) the curve changes i t s curvature at about 61°C. This may be taken as the t r a n s i t i o n point of the o< i n t o (3 form. As can be seen from the curve, near the f r e e z i n g point of the d e c a l i n , the s o l u b i l i t y of the d i c e t y l i s extremely small. No e u t e c t i c was detected even w i t h a .03 molec . percent d i c e t y l , i n d i c a t i n g p o s s i b l y a mixed -c r y s t a l type of curve. 19 71 Conclusion 1. The c i s d e c a l i n used had a f r e e z i n g point of -41.22°c. 2. The d i c e t y l a f t e r f i f t e e n r e e r y s t a l l i z a t i o n s from g l a c i a l a c e t i c a c i d had a melting point of 69.55°C, agreeing with that of P i p e r . 3. The s o l u b i l i t y of d i c e t y l i n c i s d e c a l i n was determined. 4. The a f f e c t of a saturated d i e y l i e r i n g compound on the d i c e t y l i s almost the same as that of a mono-cylic r i n g compound. 20 Bibliography 1. S. Y. P i l a t and M. Godlewicz, Oel und Kohle, 11, 655 (1935) 2. K l i n g , German Patent 362, 458 3. W. F. Seyer and R. Fordyce, J . A. C. S. 58, 2029 (1936) 4. W. F. Seyer, J . A. C. S. 60, 827 (1938) 5. Hildebrand, <J. A. C. S. 59, 794 (1937) 6. S o r a b j i , J . Chem.Soc. 47, 39 (1885) 7. K r a f f t , Ber. 19, 2219 (1886) 8. P i p e r , C h i b n a l l , Hopkins, P o l l a r d , Smith and Williams, Biochemical Jo u r n a l , 25, 2072 (1931) 9. Hildebrand and Wachter, J . Ghem. Soc. 51, 2487 (1929) 10. Garner, Bibber and King, J . Ghem. Soc. 1533 (1931) 3 $ ' % « ^ • o -o— D0  -3&nj-V33cfW-3J_ o *0~r 1 -rJ ; , 4 - 1 ^ - — - , -_rj 1- ! _ J . M I j : 1 M t : : B ± t f M r 1-rhK-fxHtJ-r! 1 - . i - - 1 -< t . — l • - - { - i - _ r M . t .- ! ! . \ , I" _'. 4- _ o -4 1 " ~ T ( " , T i T ! i - > M 4 T - J — - , _ ' , , , • , | ; • -I i -' f ! - r • i - j i I - f- , . i ' i i I i " t 1 i - 1 i \ ' \ i ' 1 . t : : i • ~ I TTtTl- rrrv i : 1 ; '-;Ml- ; - " J - J ^ ~ ] _ ; j - i i " ; • I! ' , r I T H — ' - \ _ x ; 4 4 t ; - ; - M H : : • - i \ t i • : - - - ; - " i ! • i ; :px:L|:i.JX!-"]TLCLLp"LG; ]f|Ht@M X \ I i * • | 1 ~ ! - r ; | \ ! i 1 — i • -• . ' ' i ^--1 1 Z_l t ' - ' h i 4 - . 1 1 1 ' i 1 1 1 ! i i 4 ^ ! ; , I'1 -\ - } ! 1 ; : J -L t- , t M 4 #4M4 : i \ i M i i M i i J , - ^ . . ^ ... . r . „ . . . , - r » . . f . r v _ . r „ ....... 1 - . : ) i :o'"H;M~H~ w \ < M M : . L • •; • i \ . : , - i i 1 \ - ' \ f ; g ; _ i - " . . . r . - . ! . ! . 1 \ . i h ; L i I i < \ r ; ! i ^ ! - ' — — -rQJ 4 4 ~ 4 ' t 4 ~ • fTTi • • > , ' r " H i j 1 - i ; i ; * ' - - i ' i ! ; ! • 1 ( M i . 1 i i i ' i i M " : i : • i \ • ! i I"1- \ ... .. - r -h- ! - ! *: M ;. :;±3: 1 i !, J \ - r. . « . f . - J ! 1 . I f f l i j M : I t q : t - i . ; — i 4- :. M L 4JX... , J T O \ i l f f i 4 : f " - f a x ! 4 J ^ T f ^ • ' [ _j t , 1 '< "-1 • i i ,1 i i I : M : • i • ; J > - i 1 J u " _ L . }__ 1 4pt ~;~4H- 4 ~ 1 r>-T•>;"''<!'r-<-~<'fV,"^r~:~ i 1 J .. - j " i 1 t i FFn:a4LD4:]:.r^:|;M::|F^ •frH" 1 i i.-l -+ 1, f . ! . r [ i - -1 ' ' ! ( • ' ! , . - , ! i • f . . , ' i_ • 1 • > - , - \ WW .j44_4|.!4|4 -l,-T- m T! •(. i T'i n "i , r . r ! r h ' ~ " \ i MriikMH' • T ( T ' ; T " I 1 T - j - . ^ - r i - r r . . . . . . . . I \ \ \ M i i t i M i i M ~ ! i _ i _ ; r , \ : : i ; i"Ti j . ' i- .' M J M M i 1 M f M M \ f L 1 f 1 4 f • • ! - i , 4 ' ! . . . A i ::L::'M':/:r;' t • '..1 ! j I . 1 - i • TiXOTX' -LVi - ' - ' - J - j 'p ..o;'.'. ! 1 ! t 1 ! z r j - j; i A i :\ i ; - - i I . ' ! l i t -I i j r L J _ ; i > j _ • , \ L i i T » : r ^ ! - h . -1 ! < i * , i : H T F R : H T i - - ! - ! - ! i 1 r • i- I , - - 1 i ', 'r i 2.9C V y 1 3 oo, J./O | ; 3.zo\ - 1 i 1 ; 1 . ! t 1 • f T i > . ••" 1 ' I i • i ' "1" \~r i 1 i 1 \ : i f M - 1 | - 1 1 l j ! - H - 1 r - j- n - 1 - ' [ i 1 I - ' f t - - f -! - ! - T - ' i I I i ' ' i t ' l l 1 i > — r i i i i i 2.0 / . a / . £ /o o.a 0.4 0.2. 0.0 .0.2 -0.4--OJQ - / o -1.4-

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