'FISHERIES RESEARCH BOARD OF CANADA

Translation Series No. 2653

Liquid-liquid equilibrium in systems with tricresyl phosphate II. The tricresyl phosphate-water- ,

organic acid systems

by V. Ababi, N. Bilba, and P. Onu

Original title: Echilibrul lichid-lichid in sisteme cu tricresylfosfat. II. Studiul sistemului tricresilfosfat-apa-acid organic

From: Analele Stiintifice Universitatii al I.Cuza, Iasi. Sect. 1C (The Scientific Annals of the University. I. Cuza, Iasi. Sect. 1C.), 12(2) : 105-114, 1966

Translated by the Translation Bureau( LC) Multilingual Services Division •

-Department- of the Secretary of State of Canada

Department of the Environment Fisheries Research Board of Canada

Freshwater Institute Winnipeg, Man.

1973

- 18 pages typescript

I

,.L

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TITLE IN ENGLISH - TITRE ANGLAIS

ABAABI^ V.., BZLBA$ N. & ONUj P.

INTO - EN

TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS)

TITRE EN LANGUE ETRANGERE (TRANSCRIRE EN CARACTÉRES ROMAINS)

Echil.i.brul lichid-lichid in sisteme eu tricresilfosfat. II.Studiul sistemului tricresilfosfat-apa - acid organic.

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I^,i.rynid-liQuid ernailibritun in systems with tricresyl phosphate.II. The tricresyl phosphate-watex^-organxc acid systems.

VOLUME

The Scientific Annals of the University T. Cuza., Iasi. Sect. 1C.

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Liquip LIQUID EQUILIBRIUM IN SYSTEMS WITH TRICRESYL PHOSPHATE . "ft. -TfiE-TiabRESYL PHOSPHATE --WATER . - ORGANIC ACID SYSTEMS.

Y. Abel., N. Bilba and P. Onu.

From 2 Analele Stiintifice IJniversitatii I. Culla, Iasi, Sect. 1C, vol. 12, ' No. 2, p. 105-114, 1966.

(Scientific Annals of the' University I. Cuza, Iasi, Sect. 10, Vol. 12, - 2,s4 105-114, 1966.)

Communication presented at the Republican Session of Chemistry, of Timi-- poara, g‘n:1 27730 1966.

The study of tbe _ phosphate in ternary glistens becomes

and the behaviour of the tricresyl

increasingly necessary because of its

multiple use in differeht economic fields. In a previous publication (1)

the main utilisations as 1.1e21 as the behaviour of the tricresyl phosphate

SOS-200-10-31

in systems with alcohol were specified. In order to expand the knowledge _ _

of the properties of the terparv mixtures with this component, as well as

the distribution of the different components nt equilibrium, the tricre-_ _

syl phoephate rwater- organic acid system is studied in this work. For

the third component of the system we uned acetic, propiontc, butyric, nor-

mal valerianic and iso-valerianic acids. _ - -

Experimental Part.

The experimental studies referred to the mutual solubility test

- of the components, as well as to the distribution of the re peetiye acids UtUI)liE r.)

oely

l'RADuct1.:, HON RrVISEE Infcrmm!itle% lcuktmoni

between the conjugated phases.

•For the systems with the acetic, propionic and butyric acids,

the lines of communication and the conjugated curve were esttblished.

These permitted the determination of the critical solution point,

as well as the composition of the corresponding mixture of the critical

point.

In the case of the tricresyl phosphate -water -acetic acid sys-

tem e some properties of the stratification phase were studied by using

the sectioning method, described in a series of publications by R.V. Mert-

lin and his collaborators.( 9,10,11.).

The experimental studies were acComplished using reagents puri-

fied beforehand, through repeated corrections. The degree of purity of the

reagents was controlled by determining the index of reeraction. (106) 20

The purified tricresyl phosphate, had the index of refraction n :1455745 20 D

value integrated between the limits of n t1.5510 - 1.5600, as indicated

in the literature. (7)

The organic acids used for the experiments had the following index 25 25.5

of refraction: acetic acid, n L37l0, propionic acid, n =1.38503 • 25 D 24.5 D

butyric acid, n =1.3967, n. valerieic acid, n m.1.4020 and the iso- D 25 D

valerianic acid, n =1.4013. D

The above specified values are similar to those indicated in the

literature.(8)

The determination of the mutual solubility as well as the distri-

bution at equilibriumwere determined at a temperature of 25%, maintained

constant with the help of a thermostat. For the determinations tspecial

test tubes were used, equipped with a ground-glass stopper, which allmed

a limited heat exchange with the outside.

The results of the experimental measurements were expressed in all

cases in gravimetric percentages. (%)

3

The znutua7, solubility of thecGmronents of the tricres,yl pho5rhate -w'eLtP,r-._ .,. ._ ....._..,,._......__^.._._..^..TM.^....______or^anicacid -, stem ---^.^^^...._....

.The mutual solubility of the compcncrrts in the systems studied$

was detertnined according to the turbidi*^etric metiic^d, ttsed by us in former

publications .( 2 and ^). We determi.ned the^, indcx of refrac-;;ion of the

mixtures at ec}iiilibrium by usina an Abbe refractometer for thi s purpose.

The exoerimental results were represen.ted graphically in, a trian-

plar d-i.agram. (Fig. 1).

By anal,ysing the mi-ltual solubility curves, from fig. 1, we observe

In all oaa$es their displa.çement toward the water -o-rgania acid side of the

t^.argle which dispZa.ys a tendency of the acids to dissolve in the acrueous

layer Qf the systemR Of the anal_ysed acids, the acetic and propionïcc acids

sh_.owa more pronounced tendency. The surface of'the heterogerreous regiors

ses jr the fQllowing order; propi.onic. acid. < butyri: acid <aceti^ acid ^

Uo-valeri.ani.o aozd /,xz ualeriania acid.

Thl-a shczws that the. mutual sffIubïl:ity of thffcomponer_ts dcaes not, uarv

"gttlarly with the inçrease in molecular vreight of the cfir;,-mic: acd:d but an

iiqyorsion is orcated:. the sQlubility increases from the acet.ic acid ta the

ktxtyr-i.G acid and the propionic acid y and decreases- for the n-valeri anic- and

tso--tralerianic aoid.s.A. 5-tmi? ar invexss.-on- also takes place in tài.e case of the

s^yat.ems- with lQi^er alçohols. and thj.s7 demonstrates that thïs^ inversion =a

pr oduoed by the length Qf' the hydrocarbon, chaïn which. dètermine s the degree

q€, solubility of the aléohols or acide in water and in tricresvl phQsphate.

2• M'stribu-tion at ecrtiilibrium of the organic acids (107).

IKnowi.ng the theoretical and practical immortance of the data re-

gardj.ng the distribution of one of the components between th-- two Ia,yerz

found at eauiZibritnn , in the case of. the s,ystems.zaith acetic,. propionia

and butyric acids, their distribution. bet:,tcen, the aqueous and.. tr.icres,yl

phosphate phases were analysed.

1111.

For this purpose a graphical method was used e based on the know-

ledge of the index of refraction of the mixtures found at aquilibrium 4

described in a previous publication. (14)

The data obtainci lserved for the establishment of the lines of commu-

nication and conjugated curve, and with the help of these, the position of the

critical solution point as well as the composition of the corresponding mix-e

ture were determined.

To determine the composition of the aqueous phase which contained

more than 70% waters a diagram ( index of refraction-composition ) mas used

representing the dependence of the index of refraction of the water-organic

acid mixtures in accordance with the concentration of the organic acid.

Table 1 shows the results regarding the composition of the strati-

fied mixtures at equilibrium. In the saine Table the value of the partition

coefficient K is givene this coefficient representing the relationghip between

the concentration of the acid in the tricresyl phosphat layer (Gac)t and

its concentration in the aqueous layer.(Cac)a.

By studying the experimental data we deduce that while the acetic

and propionic acids show a tendency to pass into the aqueous layer, the bu-

tyric acid even at small concentrations passes preferably into the tricresyl

phosphate layer. In both cases the tendency to pass into the aqueous layer,

that is in the tricregyl phosphat layer, increases with the increase of the

concentration of the acid.

In fig, 2 the distribution at equilibrium of 411e acids uas represen-

rhowinn the concentration of the aed in ted graphically on the abscissa,

the aqueous layer (Cac)a and on the ordinate, dlowin7 the concentration of

the acid in the tricresyl phosphat layer. (Cac)t.

k,

.4

Indice de

refracçie

As we can see by studying fig. 2., the curve which rtpi•eat'ia^t,s t21f!

distribution of the butyric acidp is situated above the diagonal e-ven in

sma11 concentrationse

a. Variation of the partition coefficient.

The partition coefficient varies between large limits,

Compoaiçia stratului1, superior

Acid3,

q ApüS.

Compoziçia stratuluip,, inferior Indice Coefic. de (108)

de refr. I repartiçie, I^^Acid Api

3 H. ^G.

a. Acid acetic

8,1015,0025,9035,5041,6053,5060,0063,2066,7067,4568,10

91,9085,0074,1064,5058,4046,5039,0035,2030,2028,8027,40

1,33871,34341,35031,35621,35951,35601,36991,37281.37671,37821,3304

1,102,805,307,809,60

14,1t)17,5521,1525,6027,3529,20

b. Acid propionic

6,306,60

11,6016,5019,6028,2036,6045,3052,0055,7056,10

93,7093,4088,4083,5080,4071,8063,0053,4044,4036,7034,70

1,33861,33891,34301,34721,34971,35631,36281,37051,37821,38631,3902

5 M

0,801,001,451,752,102,703,303,704,404,604,90

0,850,851,802,202,803,604,706,108,30

10,8013,10

4,504,85

10,8012,9017,1021,3027,7032,1037,7042,5045,20

C. Acid butiric

2,905,106,507,509,90

11,5012,7013,5014,3015,3016,201tJ,10

97,1094,9093,5092,5090,1088,5087,3086,5085,7084,7083,8053,70

4,3360 1 6,70 1,601,3379 12,90 2,301,3392 18,60 2,901,34C6 23,70 3,•101,3424 32,50 4,301,3439 38,80. 4,991,315O 43,90 5,991,3;57 47,30 7,001,346! 50,90 8,401,3673 53.20 9,901,3480 56,6,) 1 12,601,3-181 57,80 4 14,00

1,55101,54731,54161,53611,53201,52201,51431,50651,49691,49301,4890

1,54501,54421,53101,52561,51741,50851,49411,4S441,47241,-16101,4542

1,54101,52891,51791,50791,49101,47881,45331,46151,45301,44681,43691,4330

0.13i0.1860.2040.2200.2300.263

0.2920.3340.3330.4050.428

0,7140,7340,9310,7810,8720,7550.7570,7080,7250,7630,805

2,3102,5302,8603,1603,2803,3703,4503,5003,5603,4703,4903,460

Table1.Thew.r.composition of the l:iquid conjûgâtnd phases in the tricresyl phosphat-_. _ _.......,.__

t^ater-^r^7an_â.c acid^sÿste'^yat a temaoerature o.f._1.Co>tnosition of tEie tiz^ner layer, 2. Composition of the 1v:rer la.-er. 3. Acid'jr. 1•late.r. ÿ. Tndznt of rr.fractâon. 6. Partiti on coefficient.a. Acetic acid. b. Propionic acid. c. Butyric acid.

While for the acetic and propionic acids the coefficient IK1 in the case

of the butyric acid the value of the partition coefficient varies between

2.310 - 3.560 which indicates the pronounced tendency tif this acid to pass

into the tricresyl phosphate laver. In the system with acetic acid the parti-

tion coefficient increases continually with the increase of the concentration

of the acid in the mixture, while with the other analysed systems; we register

an irregular variation of it.( the coefficient) (109)

In fig. 3 the variation of the partition coefficient was represented

graphically depending on the concentration of the acids in the aqueous layer.

As wè can see, in the case of the system with butyric acid, the parti-

tion coefficient increases mith the increase of concentration of this acid

in the aqueous layer but only until the concentration of 14.30% butyric acid.

At bigger,concentrations of the butyric acid the partition coefficient decrea-

ses. In the case of the systems wi th the other acids, the limits of variation

of the partition coefficients are more restricted.

b. The lines of communication, conjugated curve and critical solution point.

With the help of the data from Table 1, the lines of communication and

the conjugated curve were established for the systems with acetic, propionic

and butyric acids. The critical solution point of the systems is deduced

from the intersection of the conjugated curve with the reciprocal solubility

curve. For this purpose a graphical method was used as described by F. Othmer

E. White and E. Treuger. (5).

Fig. 4 is the graphic construction of the lines of communication and

conjugated curve for the tricresyl phosphat-water-acetic acid system, also of

the critical point C of the saine system.

The verification of the experimental data, on the basis of mhich the

lines of communication were established, were also done graphically by using

the method described by D.F. Othmer and P.E. Tobian.(6).

- 7

.••

56,30

53,50

42,40

I 5 Compozitia arnestecurilor,

1‘, Acid 7Ap:1 ; erricresilfosfat

13,10 30,60

23,00 23,50 •

55,80 1 1,80

,:hiètèsilfbsttit=àpà—Étèid ,!etic

propionic

Tiei1fôsfatr.apacid butiric

1. Sigtenul

4* • For' this purpose > in fig.. 5 > the variation of the report (1 - a)/a in accor-

dance- with Cl --b)/b in which (a) represents the percentage of acid in

the upper layer and CO the percental7e of tricresvl phosphate in the lower

layer> was represented in logarithmical coordinates.

As we can sem by studying fig. 5, in all cases the points ere placed

ôn- à straight line which shows the accuracy of the determination. Only in the

6ese Of' the butyric acid, the change of the inclination at a certain concen-

tration can be better observed, and this is because of the modification of

itg partition coefficient between the two layers.

The composition of the mixtures corresponding to the critical solution

pOints of all the studied systems, was also determined.

The data regarding the composition of these mixtures is given in Table .

ÀÉ lee Can gee, with the increase in molecular weight of the acid in

thé Mixture corresponding to the critical point, the quantity of water increa-

géà a:J1d the quantity Of acid decreases especially the tricresyl phosphat.

(110)

Table II The composition of the mixtures whIch correspond to the critical points. 1. System. 2. Tricresvl phosphate-water-acetic acid. 3. Tricresyl phosphate---water-propionic acid.Li. Tricresyl phosphate-water-butyric acid. 5. Composition of the mixtures, %. 6. Acid , 7. Water. 8. Tricresyl phosphat.

>

3. Study of the stratification field of the tricresyl phosohate--wate!r--acëtic acid system.^

For a detailed kno.•rJ.edge of the behaviour of the studied systemsp

in the case of the tricres,yl phosphat-water-acetic acid s,vstem, the field

of stratification was thoroughly studied. For this purpose the sectioning

method described by R.V. Plertlin and his collaborators, was used.(9,10,31)

From the above mentioned system, five sections were separated (I-V) represen-

ting the lines traced from the tip of the triangle which corresponds to the

acetic acid to the line representing the tricres.yl phosphat-water binary

system. The wei^_,ht ratio of the two components (water-tricresyl phosphate)

which corresponds to the five sections, had the following values:lr-10:90;

u.- 30:70; 11I.- 50:501 IV.-70t30; V.- 90:10. To the mixtures containing

the two components with constant composition, the acetic acid was added in

increasing proportion and within the limits of the stratification field.

After establishing the equilibrium , the index of refraction of the

mixtures represen.ting the two liquid phases was determined. In :a g. 6 , on

the basis of the experdinental data, the functional curves were established

for both phases of all sections. These represent the dependence of the index

of refraction on the percentage of the acetic acid in them9.xture.

Using the above mentioned graphical representation , a large number-

of lines of communication could be traced in the stratification field of the

tricres,yl phosphate-water-acetic acid s,ystem.(fig.7)

The binodal points of the reciprocal solubility curve were also de-

termined,by using extrapolation.In Table III, a series of experimental data

was given which was used to trace the line s of communication and for the de-

termining of the composition of the binodal points.

By analysing the distribution of the lines of communication , their

constant deviation from the tricresyl phosphat-jater line towards the criti-

cal solution point , is discovered. (^1)

Nr. lini ilor

de legâturà

2 ' Nutrarul sectiunilor

I II I IV I v

3. Compozitia punctelor binodale

iendicele de refr al punctelor b inodale

Stra zul de e.solveru I II

S tratul 5. apos

7,9 10,3 11,0 13,6 17,2 21,1 23,4 28,2 29,4 35,1 34,4 40,7 39,1 45,8 43,4 5,2 47,0 53,7 50,1 56,8 52,9 59,6 55,0 61,9 57,1 - 58,8 - -

12,75 17,19 26,60 34,80 42,20 48,00 53,10 57,58 60,70 63,50 65,80 67,00 67,90 68,60 68,81

• 68,90

2 , 95 1,3425 134.50

5,50 1,3510

8,10 1,3555 10,50 , 1,3600

13,10 1,3635

15,30 1,3665

17,40 1,3600

20,00 1,3714

22,00 1,3734

24,80 1,3755

96,70 1,3775 99,80 • 1 38.-,0

32,10 1,3825

34,60 1,3846

36,90 1,3865

1,5475 1,5450 1,5400 1,5350 1,5300 1,5250 1,5200 1,5150 1,5 . 00 1,5050 1,5000 1,4950 1,4900 1,4850 1,4800 1,4750

1 2 3

5 6 7 8 9

10 11 12 13 14 15

. 16

3.9 5,1 7,8

11,0 14,1 17,1 10,7 22,2 21,6 26,8 28,9 30,8 32,8 34,5 36,0 37,4

6.0 8,3

13,4 18,0 22,4 26,8 30,8 34,6 37,9 40,7 43,3 45,5 47,5 49,2 50,8 52,2

11,8 16,0 24,9 32,8 39,3 45,4 50,3 54,7 58,9 62,2 64.6

This indicates at the slme time, a uniform variation of the index of refrac-

tion of the solutions, depending on their composition.

The intersection of the tuo loops resulted by folding the functio-

nal curves, made possible the study of the composition of the mixtures which

correspond to the critical point ) also in this we. . As we can see, by studying

fig. 6, the mixture which corresponds to the critical point Cy contains

acetic acid, which is close to the value determined graphically, by using the

method described by D.F. Othmer, E. White and E. Treuger.(5)

Table III The percentage of the acetic acId- in the mixtures which correspondsto the

sections ard the binndal points.

1. Nimber of communication lines. 2. Number of sections. 3. Composition of the binodal points. 4. Index of refraction of the binodal points. S. Aqueous layer. 6. Solvent layer.

Conclusions

The following conclusions were found by studying the tricresyl phosphate-.

-wateri.organic acid system:

ià The Mutual selubility of the components varies according to the

substance of the organic acid. The surface of the heterogeneous region

increases in the following ar der: propionic acid <butyric acid < acetic

acid< iso-valerianic acid <n-valerianic acid.

2. The partition coefficient of the acid varies within large limits

between the conjugated phases, and generally increases with the increase of

the concentration of acid in the aqueous layer. In the case of the system (112)

with butyric acid at equilibrium, it passes preferably into the tricresvl

phosphat layer. The partition coefficient of the butyric acid varies between

the limits: 2.31 - 3.56.

3. For the systems with acetic, propionic and butyric acids, the lines

of communication, conjugnted curve and critical solution point were determined.

The composition of the mixtures which correspond to the critical point is mo-

dified according to the substance of the acid. Passing from the acetic acid

to the butyric acid the concentration of acid and tricresyl phosphate decrea-

ses while the concentration of water increases.

L. The properties of the stratification field were studied in the

case of the tricresyl phosphate-water-acetic acid system $ by using the sec-

tioning method described by R.V. Nertlin and his collaborators. 4y observing

the lines of communication it is discovered that the properties of the stra-

tification field modify regularly, which dhows that between the components

of the system, there are no physical or chemical interactions which could

modify the properties of the mixture.

5. 1y using the sectioning method,the composition of the mixture whiseh

corresponds to the critical point was verifiedend the values which were

found were similar to those established by using the method described by

D.F. Othmer, E. white and E. Treuger.

The General Chemistry anl Technology Laboratory University u Al. I. Cuza "

1.

2.

3.

8.

- 11

• 1UU3.»..QRAFLE '

„ 1. A b i b i V. (,1 :1111 b.;i „estuilikt,e Ji,c,tuicle.-,liquide les e:vec • )1,ompl,tee •ee ,(-uttb•

2. A bi.bi V. i P p A. - 411 •.,siatemtclui iletatcy ,:acid ic-a pa- ào I ve 1. 1. W.L• -4 (1960), p. 429.

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4. A I) u V. j )\1 eh. - euctiu/ •ca-;k1 lc: -a pci cal ( usincç • .5,tudia thuv .B.eibes-Bolyai iuj. •Ste.rie,s Cht.unia, .1 (1963), p, 429.

5. Othmec F. D., -NV h .i '.t ç E., 'T:f.e g e - xl ruction data. 1nc.1. Eng.. Chu. ,(.1-n.4.13.i.s..tr.), L ,33 • 19,411, .p.

P. Othiller J. s :E. P. - line es-lei-elution. Eng. Chem. 3-4„( 942),

"'"'e•

't k . ■ s K. - Chen-tie, 3'er:ha:a:IDS; ie e'er Iretc ;mac he s. Leipzig,

Manus:do/ ingicencb.i 1, :Ed.. 1-ehnic,à. .Bue., 1951, p. 354 ; 407 ; 626; 582.

• .iegraphv

Liquid-liquid equilibrium in sy.steras wit.h tricresyl phosphate.

The study of the lactic acid-water-organic solve.nt tœnlar.v s:vstem.

The study of the ethylene e2oro1iydrin --Ilate•-oresanic solvent system.

The study of th e acrylic .a.cid -water -organic .solvent system.

The manual of the chemical e:ng,ineer.

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10. Mertslin, N.V., et al. On the property of the strati- fication of ternary systems comprising a dominant binary system. 111. Journal of Physical Chemistry, XXXV, N0.12 (1961). 2770.

•* •

9. Mepua ii H fl.J3. ki .1( p au( -,a ii. 14.-0 x za.7.11 paec.icoeii if a rpoii- alux cutuem D'K.f.nomelotull'xintylo o6outvi...cnç:remy. 1. XXXV, 11, (195.1) ..c:r.p..2&15.

11. Mertsl in, N.V., et al. fication of ternary systems compr •1. Journal of Physical Chemistry,

On the property of the strati ising a dominant binary system. XXXVI, No.II (1962). 2491.

FD^

- 12 -

A D ET1C

Fig. 1

L&

Tf2lCR£S1L- ^^

FOSFAT '

Mutual solubility of the components in the tricresyl bho^hat rater-organicacid system.

A. Water. B. Tricresyl phosphat. C. Acetic acid,l. Acetic acid. 2. Propionic acid. 3. Butyric acid. 4. n-valerianic acid.5. Iso valerianic acid.

:t

so

20

10

e.

,v

130 f ,

so 0. 10 20 30 „ 40 — LC4A Z

n

Fig. 2

Distribution of the acids at egrilibrium.

1. Acetic acid. 2. Propionic acid. 3. Butyric acid.

I 4,

r m

, I

10 20 34 44

Fig. 3

Variation of the partition coefficient depending on the concentration of — the acids in the aqueous laver.

1. Acetic acid. 2. Propionic acid. 3. Butyric acid.

r.z,C,U3K- ^ ,r w.47

Fig. !t

Lines of communicâtion,_ con ju.r,,ated curveand critical solution point ofthe tricresyl pho sphat-water -organic ac id s,stem.

1. Water. 2. tricresfl phosphat. 3 Acetic acid.

Fig. 5

Variation of the report (1 -a)/a in accordance vith (1 - b)/b.

1. Acetic acid. 2. Fropionic acid. 3. ilutyric acid.

N ,V

\

• • /

/ \ \

Ill A

\ \ ,!

N \

\X"

1

70 fa 20 30 40 %,4CiD ACE 77C

re SO •

/5 i rin

—

e5:-.ta0

bera

1,47ou

1,4500

1,43J0

i4/00

1,390Q

(ea mgo M417

• F1. 6

Functional curves of the index of refraction for both phases of the sectiôns.

_2. Acetic acid. •

3.I--- ,

ACID r4CE7lC

ITR1CR1^$!L -

FOSFRT

Fig.?

Mutual solubilit,y curve and Lines of communication in the tricres,yl phosphate^rat^r^ acetic_acid sÿstem at a temperature of 25'G.

1. Water. 2. Tricresyl phosphat.3. Acetic acid.