LIQUID-LIQUID EXTRACTION DATA DONALD F. OTHNIER, ROBERT E. WHITE, AND EDWARD TRUEGER Polytechnic Institute, Brooklyn, N. Y. Considerable data of a physical-chemical nature form the fundamentals upon which the development of liquid-liquid extraction processes may be based. Among these data are the solubility relations-mutual solubility and distribution coefficients-for the constituents involved. These relations cannot yet be predicted but must be obtained experimentally. The usual extraction system involves three liquid components-one pair of immiscible liquids and two pairs of miscible liquids. When the three components are present in such quantities that two liquid phases exist, the common miscible liquid distributes itself between the immiscible p ~ in h accordance with the distribution law. The presence of the miscible liquid increases the solubilities of the immiscible pair in each other; in other
ONSIDERABLE data of a physical-chemical nature are
C
necessary for the development of liquid-liquid extract,ion processes and the design of equipment for them. A knowledge of the phase equilibrium relations (mutual solubility, distribution characteristics, and concentration characteristics) for the constituents involved allows the prediction of the applicability of the process and permits a mathematical treatment of the extraction methods that may be used. A liquid-liquid extraction process is concerned with a t least three liquids and is based on the transfer of one liquid, the solute, from a solution in a first liquid phase to another liquid phase in order to bring about any one of several effects. To avoid confusion, the liquid in which the solute is originally present will be termed the “diluent” and the other liquid will be termed the “solvent”. The diluent and the solvent are, of necessity, practically insoluble in each other. The solute, however, in the usual case (the only one considered here) is completely miscible with both the diluent and the solvent; and when added to a two-phase mixture of the two, it distributes itself in accordance with some partition law. The presence of the solute increases the solubility of the diluent in the solvent and of the solvent in the diluent. The driving force causing a n extraction process to proceed is measured, as with any diffusion process, by the distance the system is from equilibrium. The difference between the actual concentration of solute in one phase and the concentration which would be in equilibrium with that of the other phase is the force tending to dissolve (or release from solution) the solute. The algebraic sum of these differences of concentrations causes the process to go forward. Obviously, the extraction may proceed in either direction; and the terms “diluent” and “solvent” have to adjust themselves, depending on the operation in question.
Ternary Diagram or Mutual Solubility Boundary The solubility-composition relations of a three-component system are usually represented graphically on a triangular coordinate plot with one side as a base; the left vertex represents 100 per cent solvent, the right vertex, 100 per cent
words, the mutual soIubility increases. When two phases exist, they are mutually saturated and a plot of the compositions, on triangular coordinates, of these saturated phases give the so-called mutual solubility curve. Simple and rapid methods for determining accurate data for these relations have been developed through modification of previously developed methods. Several methods of carrelating the distribution data have been investigated in an effort to evaluate their advantages. Distribution and mutual solubility data and representative plots for a number of systems of acetic acid-watersolvent, acetone-water-solvent, and ethyl alcoholwater-solvent are given. These systems are of commercial importance since extraction processes involving them are used industrially and are the bases of many patents.
diluent, and the top vertex, 100 per cent solute. Other per cent lines for the respective components are laid off a t proportional distances along the altitude joining each vertex with the opposite side; the length of this altitude is taken as 100 per cent. The sum of the vertical distances to the three sides from any point within the triangle is also equal to 100 per cent, from geometric considerations; thus the plotting of the values for the percentages of any two compounds of a ternary system determines a point in the triangle, fixes the percentage of the third component, and checks the corresponding arithmetic. If the quantities of diluent, solvent, and solute present in a ternary mixture are such that two phases exist, each phase is said to be mutually saturated. A plot of the compositions of the two individual phases when in equilibrium with each other gives a mutual solubility curve, exemplified in Figure 1 for a typical acetic acid-water-solvent system. Any point located on the right branch, BMK, of this mutual solubility curve, represents a solution of solute in a diluent phase saturated with solvent; any point on the left branch, ASK, represents a solution of solute in a solvent phase saturated with diluent. No single-phase solution can have a composition represented by a point under this line; and points on or outside this curve represent all possible compositions which have a single phase. The area under the curve (having as a base the line joining the vertices of 100 per cent solvent and 100 per cent diluent) represents all mixtures of the three components having two phases. The nearer to the right branch of the curve a point in this two-phase region is, the more the amount of the diluent phase is in comparison with the amount of solvent phase. Conversely, the closer to the left boundary a point representing a given composition is, the higher the ratio of amount of solvent phase to amount of diluent phase. Point K , the intersection of the diluent and the solvent branches of the curve, is called the “plait point” and has some unique characteristics. It represents simultaneously a solvent and a, diluent phase, and is a point where both phases have the same composition and density. It is near but practically never on the crest of the curve, since the curve is 1240
October, 1941
INDUSTRIAL AND ENGINEERING CHEMISTRY
1241
points for the diagram, was devised by a combination and modification of some of these methods. The liquid mechanism is evident from Figure 2; but it should be noted that if one of the three liquids is added to any liquid composed of one, two, or all three, then the loci of the compositions of the mixtures formed by continuing this addition is a line joining the original composition and the vertex of the triangle c o r r e sponding t o 100 per cent of the liquid added.
[L
w
53
Ten to twenty cubic centimeters of solvent are measured into a 125-cc. Erlenmeyer flask; and diluent is added from a buret and agitated until the solution becomes.turbid. These amounts are converted by means of known densities of the three pure comonents from volume to weight units and then to percentages. h e y are recorded as the maximum solubility of diluent in solvent, since the turbidity indicates the formation of a second phase, the diluent layer. In Figure 2 the addition of B to A gives point Q, the point of solubility of B in A .
B 1.00
0.95
Y\
a
I YO.90
>
t ffl 2
g0.85
0.80
FIGURE 1. TYPICALTERNARYDIAGRAM SHOWING MUTUAL SOLUBILITY CURVE, TIELINES,AND CON JUG AT^ CURVE
seldom symmetrical because of different rates of change of mutual solubilities of the two phases with change of amounts of solute present. The plait point is also located where the radius of curvature of the curve has reached a temporary maximum-i. e., a flattening of the curve. various experiDETERMINATION OF TERNARY DIAGRAM. mental procedures for obtaining the data for ternary diagrams have been given (7, IO); and a more rapid and simple method, which permits the determination of a large number of
0.75 W T % SOLUTE
FIGURE4. DENSITYOF CONJUGATEPHASES FOR THOSE SYSTEMS REQUIRING THE SYNTHETIC METHODOF TIE-LINIDETERMINATION 26, methyl isobut 1 ketone. 30 di-n-butyl ether: 31,di-npropyrketone;’ 32,’n-amyl aloohol
One or two cubic centimeters of the solvent are added to the two-phase mixture and because of its consolute effect, a clear sohtion results. The addition of C (Figure 2) is along the line CQ, which is outside the solubility curve; point R may be taken as representing the final condition. The diluent is again added until turbidity results; and this addition of B is along the line RB to point S. The total amounts of the three liquids used at the end of this second ste again represent a mutua& saturated phase, and a second point, S , on the solubility curve is obtained. Successive additions of solute are made to give lines SC, U C , W C , etc.; and each time the resulting clear solution T, V, X , etc., is titrated with diluent to turbidity along lines TB, V B , X B , etc., t o give points U , W , Y , etc. Finally, turbidity no longer results from the addition of diluent, and only A B A 6 a single phase exists. This L is shown by the line from FIGURE2. GRAPHICAL REPRESENTATION OF FIGURE 3. GRAPHICAL REPRESENTATION OF Z to B , which does not inDETERMINATION OF TIE LINES DH~TERMINATION OF MUTUAL SOLUBILITY CURVE tersect the solubility curve.
1242
SOLVENT
I N D U S T R I A L A N D E N G I N E E R I N G CHEMISTRY
Vol. 33, No. 10
WATER
CURVESFOR SYSTEMS OF ACETICACID, WATER,AND SOLVENT FIGURE 5. MUTUALSOLUBILITY 3, Hexalin acetate; 6, butyl carbitol acetate; 7. b u t 1 diacetone ether; 10. di-n-butyl ether: 12, me%yl isobutyl ketone. 15, diisopropylcarbinol: 16, glyooi diaoetate
1, isopropyl ether: 2, rliisobutyl ketone; 4. methyloyolohexanone: 5 , butyl lactate: 11, octyl acetate; 14,isoamyl acetate
8, butyl acetate; 9 fenchone: 13, isophorone; I?, triacetin
The data sbtained by the titrations are for ternary mixtures containing a large percentage of solvent and always represent a solvent phase. When plotted on triangular paper, points are obtained, as in Figure 1, on the solvent side or branch, A S K , of the curve bounding the twophase area. T o determine points on the diluent side, BMK, the same procedure is followed, starting with a n initial measured quantity of diluent in the flask. Solvent and solute are then sucFIGURE6. MUTUALSOLWILITY CURVES FIGURE7. METUAL SOLUBILITY CURVES cessively added to give the FOR SYSTEMS OF ACETONE,WATER, AND FOR SYSTEMS OF ETHYL ALCOHOL, WATER, points representing all possible SOLVENT AND SOLVENT compositions of the diluent 20 tetrachloroethane. 21 xylene. 23, monochloro30, di-n-butyl ether; 31, di-n-propyl ketone; 32, 25. methyl isob;tyl ketGne: 26, furfural; behsene; n-amyl alcohol; 33, isoamyl alcohol phase. A similar plot of the lines 27, beneene to points A and C would indicate the paths of these additions. It is difficult t o determine exactly points near the plait line with reference to its intersections with the two branches point because of the little difference between composition and of the curve determines the amount of each layer. The disdensity of the two phases. A point in this vicinity may be tances from a point representing any composition inside the checked, if desired, as follows: solubility curve to the opposite ends of the tie line on which the point is located, are in inverse ratio to the weights of the A line is drawn from the diluent apex of the curve throu h a respective phases, the compositions of which are given by the point near or at the location of the plait point, as estimated 8om the previous data; and this line is extended to the opposite side coordinates of those points. Thus, in Figure 1, with point W of the triangle, at point U in Figure 1. A mixture of solvent and on tie line EWD representing the over-all composition of a solute alone, of composition indicated by U,is made by adding mixture of two phases, the right amounts of the two components. Pure diluent is titrated into it; and the resulting composition of the mixture must length EW - wt. diluent layer of compn. Il be on line BU,which is the locus of all points of ternary composilength W D wt. solvent layer of compn. E tion where the ratio of solute to solvent is the same as that in the original synthetic mixture. The intersection of line BU with the One interesting feature of a tie line is that all points on it, solubility line is determined by the appearance of turbidity. being made up of different ratios of the same two phases, will Several points near the plait point may be checked in this way to establish the curve definitely in this range. have the same vapor pressure. The individual vapor pressures of each of the three components are the same out of both Tie Lines, Distribution Curve, and Conjugate phases; and the total vapor pressures (the sum of the three Line partial vapor pressures) are also equal for both phases; otherwise any liquid would distill from a phase of higher A line connecting points on the opposite branches of the vapor pressure to one of lower vapor pressure. solubility curve, representing two coexisting phases, is called Since tie lines are not horizontal or parallel to each other, a “tie line”. Such a line is exemplified by ED and by SM in an infinite number would be required to show completely the Figure 1. Intermediate points on any tie line are in the twodistribution of solute between solvent and diluent a t all conphase region and represent a mixture with two phases having centrations. Instead, a distribution curve is often used to as their respective compositions the points at the terminals represent these equilibrium relations. This is a rectangular of the tie line. Furthermore, the position of a point on the
October, 1941
t
I N D U S T R I A L ANT) E N G I N E E R I N G C H E M I S T R Y
plot of the percentages of solute in the solvent phase against the percentages of solute in the coexisting or conjugate diluent phases. Either the tie lines or the distribution curve may be obtained directly from the other. The so-called conjugate line, drawn as FKL in Figure 1, represents the same data in a different manner on a diamondshape plot distorted from the 90" angles of the usual Cartesian coordinates to 60" angles. It is a plot of the percentage solute in the diluent phase against the percentage diluent in the coexisting solvent phase. Thus in Figure 1, point E represents a saturated solvent phase having 6 per cent water; and the corresponding or coexisting water phase, point D, contains 5 per cent solvent and is a t the other end of the tie line. By running along the 6 per cent water line and the 5 per cent solvent line, a n intersection a t point F is reached, to determine a point on the curve of solvent in water phase vs. water in solvent phase. This curve may be drawn mechanically by similar projection from the ends of other tie lines and extends from the solute vertex to the plait point K. A similar curve under the mutual solubility line extends from K through L. Points such as G are obtained by running along the line representing the amount of solvent (73 per cent in this case) in the solvent layer until it intersects the line representing the amount of water (55 per cent in this case) in the water layer. The whole curve, solvent in diluent phase vs. diluent in solvent phase, and solvent in solvent phase vs. diluent in diluent phase, is ordinarily of less use than the plot representing the distribution of solute. Branckner, Hunter, and Nash (3) and Bachman (1) have developed equations and plots similar to and depending on these relations; this work will be discussed in detail in a subsequent paper.
1243
TABLEI. DATAON SYSTEMS INVESTIGATED System No.
Solvent
Temp.,
O
--Figure No.TerEffPCnary tive diaDistn. concn. C. gram curve curve
Acetic Acid as Solutes 23-24 23-24 23-24 23-24 23-24 23-24 23-24 24 22! .5-24 24 .S * 0.5 23 22 e 24 .O =t0.5 23-24 24-25 24-25 24-25
1 2 3 4 5 6
7 8 9 10 11 12 13 14 15 16 17
as Solute0 25-20 25-26 25-20 25-26 25-26 25-26
5 5 5 5 5 5 5 5 5 5 5 5b 5 5 5 5 5
20 21 22 23 24 25 26 27
Acetone Tetrachloroethane Xylene Toluene Blonochlorobenzene Di-n-butyl ether Methyl isobutyl ketone Furfural Benzene
30 31 32 33
Ethyl Alcohol as Solutea Di-n-butyl ether 25-26 , 7 Di-n-propyl ketone 25-20 7 %-Amylalcohol 25-26 7 Isoamyl alcohol 7(6)
..... .....
.....
8 8
8 8
.... .. ..
8
8
8 8) 8 8 8
....
11 11 11 11
.... .. ..
11 11 11 11 11 11 11
.. . I
6 6
9 9
12 12
.. 6
9
12
9
.. 6
%I
9
..
..
90
12 12 12
1OC
13 13 13 13
%I 100
1oc lO(6)
Water was the diluent component in every case. b The data for this system agree closely with the corresponding data given in the Am. Inst. Chem. Engrs. Contest Problem for 1940. C Synthetic method. 5
or solvent concentration. I n the following description, however, it is assumed t h a t the solute concentration can be determined directly by analysis, as in the case of acetic acid distributed between water as a diluent and an organic solvent. Chemical analysis is often tedious, and in many cases one or more physical properties may be used instead as a basis of evaluating the amount of one of the liquids present.
a 60
ow
%50 21-40 +Z
:;30
""z,, g5
IO 0 WT.% A C E T I C A C I D I N W A T E R L A Y E R
About 20 cc. of solvent and an equal amount of diluent are placed in a flask; 5 cc. of solute
(acetic acid) are then added, and the mixture is vigorously shaken and allowed t o settle. A 1 , isopropyl ether. 2, rliisobutvl ketone. 4, 3, hexalin acetate; 9, frnchone; 11, Of each layer is removed, and the rnethvlryclohex,ino;Ir. 10, di-;-butyl &her. octyl acetate. 13 isophorone; 15, direspective arid concentrations are carefully det&proGylcarbinol 12, ðyl isobutyl kktone; 14,isoamyl acetad termined by titration. Another 5 cc. of arid are added, the mixture is again shaken and allowed to settle, and the acid concentration in each layer is determined on samples again removed for analysis. This proAnother curve, sometimes used but not here illustrated, is cedure is repeated with progressively smallc? additions of solute that of the partition or distribution coefficient os. the peruntil only a single phase exists; i. e., the mixture is in the comcentage of solute in one phase, usually the diluent. This coefpletely soluble region above the line of mutual solubility. ficient is the ratio of percentage solute in the solvent to perThis is shown in Figure 3 where L represents equal amounts of solvent and diluent. Acid is added in total percentage equal to centage in the diluent; it is not, as its name might indicate, a the length of line OL. Two layers are still present; titrating the constant. solvent layer gives a weight per cent of acid equal to the distance YL,which is laid off. Y is projected t o the left to an intersection with the mutual solubility line at P , which is thus the solvent Analytic Determination of Distribution Curve end of the tie line. Similarly, the diluent layer is titrated to give and Tie Lines a value LZ for its percentage of acid; this pwcentage is laid off on the altitude and projected t o the intersection with the mutual If the chemical or other analysis for any one of the three solubility line at pomt N ,t h e diluent end of the line. Other tie components in both phases may be readily made, the distrilines, P'N', etc., are similarly determined. I t is obvious that since point 0 is known, only one of the points P or N would have bution data are determined by analyzing for that component t o be determined t o fix the tie line. Determination of both serves in each layer of various two-phase mixtures of the three. If as a check, since all three points must fall on the tie line. either the diluent or the solvent is more readily determined than the solute, the solute composition is then picked from The respective solute concentrations in each of a pair of the triangular diagram a t the determined value of the diluent conjugate layers when plotted against each other locate a OF ACETICACIDBETWEEN WATER AND SOLVENT FIGURE 8. D~STRIBUTION
INDUSTRIAL AND ENGINEERING CHEMISTRY
1244
TABLE 11. -Weightper CentinsystemSolvent Acetic acid Water Isopropyl Ether as Solvent (23-240 C.) 50.3 31.05 16.7 13.25 41.85 3.5 4.6 5.12 69.0 60.2 48.4 45.2 50.5 11.1
36.8 45.1 48.4 48.1 47.3 37.6 40.0 41.5 25.1 30.7 35.0 39.5 36.8 48.0
13.0 23.8 34.9 38.6 10.85 58.8 55.4 53.4 6.19 9.1 11.6 15.3 12.8 40.9
Diisobutyl Ketone as Solvent (23-24'' C.) 71.07 60.1 51.04 46.5 42.05 38.86 36.42 33.75 31.5 28.15 25.5 24.35 24.26 23.2 21.93 20.39 19.0 17.8 16.6 16.23 15.78 15.39 14.68 2.525 2.394 3.34 2.87 2.38 5.5 7.45 6.35 9.43 9.32
24.64 32.7 39.34 42.38 45.35 46.95 48.3 50.0 51.2 53.15 54.6 55.3 55.3 55.94 57.0 57.4 57.0 58.5 59.4 59.3 59.4 59.43 59.74 52.4 51.9 56.6 56.4 54.5 60.85 59.6 58.8 60.1 59.55
4.29 7.2 9.62 11.12 12.6 14.19 15.27 16.36 17,35 18.7 19.88 20.4 20.44 20.86 21.07 22.21 24.0 23.7 24.0 24.5 24.75 25.17 25.58 45.2 45.7 40.06 41.6 43,15 30.75 33.02 34.94 30.5 31.75
Hexalin Acetate as Solvent (23-240 C.) 36.0 24.7 16.65 12.43 8.55 7.36 6.06 5.12 4.4 3.9 3.1 76.1 57.1 49.0 46.7 41.3 38.4 36.4 33.45 30.9 24.6
a
41.6 44.5 46.6 47.5 46.2 45.7 44.35 43.4 41.9 40.45 38.5 19.2 31.5 35.34 35.35 38.8 39.9 40.6 40.7 42.5 44.6
22.4 30.75 36.7 40.0 45.2 46.9 49.6 51.5 63.6 55.7 58.4 4.74 11.4 15.6 17.9 19.9 21.7 23.0 25.85 26.55 30.88
MUTUAL SOLUBILITY
-Weight PercentinsystemSolvent Acetic acid Water Methylcyclochexanone as Solvent (23-24O C.) 44.15 27.36 20.03 11.17 15.55 18.75 15.5 13.8 12.5 11.17 9.94 8.67 7.035 22.05 85.6 75.1 67.8 58.4 51.7 45.15 43.1 37.2 34.85 37.5 35.5
28.8 33.0 31.3 30.21 31.8 31.5 31.25 30.9 30.7 30.7 30.0 28.78 26.07 31.45 9.72 16.18 21.16 25.2 27.58 29.44 29.85 30.2 30.65 31.8 31.9
27.1 39.6 48.7 58.0 52.65 49.8 53.2 55.3 56.8 58.1 60.2 62.55 66.0 46.5 4.68 8.61 11.00 16.42 20.64 25.41 27.12 32.34 34.45 30.8 32.6
Butyl Lactate as Solvent (23-24' C.) 61.4 47.16 43.9 39.63 36.1 31.4 22.52 19.88 15.95 13.84 13.0 11.8 9.74 8.85 7.8 7.24 80.0 77.4 68.65 56.9 65.1
13.25 13.94 14.2 14.54 14.8 15.25 15.08 15.25 15.12 14.76 14.81 14.2 13.44 12.7 12.05 12.02 3.5 5.05 8.65 12.87 13.32
25.35 36.9 41.9 45.83 49.1 53.3 62.35 64.87 68.93 71.42 72.2 74.0 76.62 78.43 80.2 80.75 16.5 17.56 22.65 30.23 31.54
Butyl Carbitol Acetate a8 Solvent (23-24' C . ) 72.9 59 I74 40.55 36.43 29.75 25.79 23.2 19.84 17.68 14.96 12.18 10.81 10.34 9.37 8.24 7.52 7.37 5.94 5.22 4.71 4.26 92.0 85.7 78.2 75.0
12.76 18.48 23.41 24.05 24.34 24.44 24.54 24.52 24.43 24.06 23.32 22.74 22.55 21.93 20.06 20.28 21.1 18.33 16.96 16.04 15.17 3.55 7.54 11.94 12.4
14.38 23.41 36.05 39.5 45.9 49.76 52.26 55.65 57.9 61.0 64.5 66.45 67.15 68.7 71.2 72.24 72.5 75.75 77.8 79.2 80.5 4.54 6 76 9.84 12.58
DATAFOR
SYSTEMS WITH ACETIC ACID AND WATER
-WeightPerCentinSystemSolvent Acetic acid Water Butyl Diacetone Ether as Solvent (23-24' C.) 25.42 24.8 15.35 10.69 8.10 6.39 5.2 4.15 3.15 74.0 63.9 56.4 47.8 41.15 36.7 32.81 28.22 25.1 23.6 22.2 20.9 16.92 15.43 14.8
38.5 42.6 44.55 44.25 43.0 41.1 39.7 37.4 34.15 19.25 25.97 30.5 34.25 37 0 38.4 39.7 41.0 41.9 42.25 42.6 42.9 63.6 44.1 43.8
36.12 32.55 40.3 45.06 48.9 52.5 55.1 58.3 62.7 0.75 10.2 13.52 18.0 21.85 24.85 27.5 30.8 33.0 34.15 2Fi.2 36.2 39.4 40.4 41.4
Butyl Acetate as Solvent (24' C . ) 34.45 24.80 16.38 9.16 2.36 0.00 100.00 86.10 73.30 59.90 46.78
34.45 37.20 38.20 36.76 21.20 0.00 0.00 9.58 18.28 25.65 31.12
30.3 38.00 45.42 54.08 76.44 100.00 0.00 4.32 8.42 14.45 23.10
Fenchone as Solvent (23.5-24' C.) 93.14 84.02 78.fi7 74.39 70.19 66.70 63.19 59.50 57.41 54.23 51.84 48.60 44.66 41.06 32.82 31.90 29.00 0.56 0.97 2.27 2.31 2.42
5.20 12.63 16.83 19.96 23.00 25.48 27.78 30.16 31.45 33.30 84.64 36. 43 38.46 40.05 44.17 44.50 46.10 15.15 25.96 46.32 46.83 54.22
1.66 3.35 4.50 5.65 6.81 7.82 9.03 10.34 11.14 12.47 13.R2 14.97 16.88 18.89 23.01 23.50 24.90 84.29 73.07 51.41 50.86 43.36
Triacetin as Solvent (24-25' C.) 94.4 82.4 70.0 57.3 37.4 57.2 58.4 50.8 97.5 5.5
1.7 7.5 12.8 15.7 17.2 15.7 14.8 16.9 0.0 0.0
Vol. 33, No. 10
3.9 10.1 17.2 27.0 45.4 27.1 26.8 32.3 2.5 94.5
-WeightPerCentinSystemSolvent Acetic acid Water Di-n-butyl Ether as Solvent (24.8 i 0.5' C.) 0.185 0.0 99.81 1.72 1.06 0.75 0.51 0.44 7.17 5.38 4.66 24.0 21.5 17.6 14.3 12.88 11.99 11.18 10.68 9.55 98.1 55.9 47.0 40.8 32.7 30.4 28.2 24.9 23.8 21.8 21.1 79.7 74.2 57.7 54.2 50.7 93.4
59.9 55.3 49.6 44.5 43.6 68.2 56.9 64.1 62.8 64.5 67.1 68.5 68.8 69.4 69.4 69.8 69.5 0.0 39.5 46.5 51.2 57.0 58.6 59.9 62.2 62.9 64.0 64.6 19.4 24.6 38.2 40.8 44.1 6.3
38.3 43.6 49.7 65.0 56.0 24.6 27.7 31.2 13.2 14.0 15.3 17.2 18.31 18.6 19.35 19.48 20.9 1.9 4.57 6.40 8.00 10.37 11.03 11.8 12.9 13.3 14.1 14.4 0.84 1.2 4.1 4.99 5.27 0.39
Octyl Acetate as Solvent (230 C.) 100.0 0.0 0.0 79.3 59.8 41.4 25.1 18.0 13.3 10.8 7.7 5.4 3.3 2.4 1.8 0.9 0.7 0.1
