AZEOTROPIC
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.fw001
DATA Tables of azeotropes and nonazeotrope...
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AZEOTROPIC
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.fw001
DATA Tables of azeotropes and nonazeotropes compiled by L. H. Horsley and coworkers at the Dow Chemical Co. Included are a formula index, a bibliography, and three articles, "VaporLiquid Equilibrium Diagrams of Alcohol-Ketone Azeotropes as a Function of Pressure," "Graphical Method for Predicting Effect of Pressure on Azeotropic Systems," and "Graphical Method for Predicting Azeotropism and Effect of Pressure on Azeotropic Constants."
Number six of the Advances in Chemistry Series Edited by the staff of Industrial and Engineering Chemistry Published June 1952 by AMERICAN CHEMICAL SOCIETY 1155 Sixteenth Street, N.W. Washington, D. C.
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.fw001
Copyright 1952 by AMERICAN CHEMICAL SOCIETY
All Rights Reserved
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
Table of Azeotropes and Nonazeotropes L. H. HORSLEY
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch001
The Dow Chemical
Co., Midland,
Mich.
This table of azeotropes and nonazeotropes is a revision of the two previous tables published in Analytical Chemistry, August 1947 and July 1949 (167, 168), together with approximately 6000 new systems, bringing the total number of systems to over 14,000. The table is arranged in two parts: (1) table of binary systems and (2) table of ternary systems, followed by a formula index and bibliography. As in the previous tables, the individual systems are arranged according to empirical formula using the Chemical Abstracts system, except that inorganic compounds are listed first in alphabetical order, followed by organic systems in the order carbon, hydrogen, bromine, chlorine, fluorine, iodine, nitrogen, oxygen, sulfur. For a given binary system the lower order compound according to formula is chosen as the A-component and under each A-component the B-components are likewise arranged according to empirical formula. For ternary systems the same arrangement is used, using the lowest order formula as A-component, the next lowest order as B-component, and the highest order formula as C-component. To facilitate finding all systems containing a given component a formula index is included at the end of the tables listing the systems containing a given component. The following abbreviations are used in the table: Min. b.p. V-l. Vol. Mm. ~ >
° C.
23 39 55 125 150
-8 -11 -15 -32 -40
26 42 57 124 149
C, W e i g h t % Found Calcd. 30 33 39 54 64
34 36 40 55 63
A plot of A as a function of C from this table is shown in Figure 6. The experimental data are represented by the five points while the smooth curve is identical with the methanol-hydrocarbon curve in Figure 1. 321
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
rangeIN indicated areSERIES also 322 Similar curves and data for other systems over the pressure ADVANCES CHEMISTRY shown. In each case the curve is the same as the general curves of Figures 1 to 5, while the experimental points are for the particular system and for the pressure range indicated. In the same way, the 5-| A| curves of Figures 1 to 5 can be used to determine 5 and the azeotropic boiling point at any pressure from the value of | A| at that pressure. While the agreement between predicted and experimental values is far from perfect, the method has served as a valuable guide in estimating effect of pressure on azeotropic systems. It is recognized that it would be more convenient to be able to plot pressure instead of A as a function of C and 8. However, this would require a separate curve for each azeotrope, whereas the above method permits use of a single curve for a large group of systems.
Literature Cited
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
(1) Lecat, Ann. soc. sci. Bruxelles, 55B, 43 (1935). (2) Lecat, Compt. rend., 183, 880 (1926); 184, 816 (1927); 189, 990 (1929); Ann. soc. sci. Bruxelles, 47B, 39, 87 (1927); 48B, 1, 105 (1928); 49B, 28, 119 (1929); 55B, 43, 253 (1935); 56B, 41 (1936); Atti accad. nazl. Lincei, (6) 9, 1121 (1929); Z. anorg. allgem. Chem., 186, 119 (1930).
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
GRAPHICAL METHOD FOR PREDICTING AZEOTROPISM
I I I I I I I I METHANOL - HYDROCARBONS
c
;
40
«0
60
KX> I20 IAI
_
TH ANI)L -1 YDm,AR
_
PR(IPANOS- HIORKJ 1RB m
too 60
>
40
5:
o
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
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IS
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: !U1AN )LS -1 IYDI I ;AR 301
20
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30
tin ANIIS
40
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40 0
-60 - 4 0
40
-I M
120
A
I I I I I I I I I HEXANOLS • HYDROCARBONS
ISOAMIfL ALCOHOLMlYDRODIETH1L DARBINOLH ,ARBOtIS
-
60
50 ,
10 I
YD 101:AR mIS
20 I I
30 I
I
40 I
I
SO I
I
,_,60 I
HEXANOLS •HYDROCARBONS
S
60
v
40 0
5f4rHYDR04PROPANOLSi OH HO O "CARBONS " ALLYL ALCO LLT TCARBONS
ETHANOl • HYDROCARBONS _
20
I I I I I I I I I I METHANOL -HYDROCARBONS
323
•60
32
-40
S
-20
60
I I I I I I I I I I I GLYCOL - HYDROCARBONS I
24
-40 I
V
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I
60 I
I
I
I
I
I
I
GLYCEROL -HYDROCARBONS
-40
-20
I I I I I I I I I PHENOL-HYDROCARBONS
16 •
I I I I I I I I GLYCOL - HYDROCARBONS
I I I I I I I I I I GLYCEROL •HYDROCARBONS
I
I
I
I
I
I
I
I
I
I
PHENOL-HYDROCARBONS
100 60
-i20
-60
Figure 1.
-40
40
60
120
-120 -60
-40
C-A and 5-|A| Curves for Alcohol-Hydrocarbon, Glycol-Hydrocarbon, and Phenol-Hydrocarbon Systems C. Azeotropic composition in weight % first component 5. Boiling point of lower boiling component minus azeotropic boiling point |A|. Absolute difference in boiling points of components A . Boiling point of first component minus boiling point of second component
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
324
ADVANCIS IN CHEMISTRY SERIES
1
;
:RESO
s
I I I I I I I I I I I I PYROCATECHIN-HYDROCARBONS^
HIOR DM IRBW
a
s. •
c
10
20
30
40
50
I A I
60
I I I I I I I I I I RESORCINOL - HYDROCARBONS
PYROIATEC1IN •HYDIOCAM m s ;
1 '
so s- HIORKf RBON!
00
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
s v 30 -20
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PROPIONIC ACID u : - HYDRO BUTYRIC ACID -iCARBONS H VALERIC ACID
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I I I I TT _ FORHC ACID-HYDROCARBON
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PROPIONIC ACID 1 1 DiiTVDip inn HYDRO-' u u r o i p i r»in CARBONS
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i
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Figure 2.
40
A
60
HJO -40 -20
20
•4* 40 « 60
- 6 0 -40 -20
C-A and 5-|A| Curves for Phenol-Hydrocarbon, Acid-Hydrocarbon, and Alcohol-Halide Hydrocarbon Systems
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
GRAPHICAL METHOD FOR PREDICTING AZEOTROPISM
I I I I I I I I I I CYCLOHEXANOl • HALIDE T T
' M I N I HALIDE ISOAMYL ALCOHOL HYDROTERT. AMYL ALCOHOLCARBON
1 11 11 1 Ii AN)LS -HALIDE 1 1 uvnonpADDnuc
325
_
HYDROCARBONS
s 10
20
30
40
TT
BUTANOLS - HALIDE
J .
SO.
T
15
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
I I I I I GLYCOL • HAUDE" -HYDROCARBONS
24
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A
10
30
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15
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40
*
20
25
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A
1
15
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1
30
CRESOLS-HAIIDF HYDROCARBONS
L HYDROCARBONS
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20
1 111 1
c
1 11 1 1 PHENOL-HAUDE
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•
0 16
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HYDROCARBON -
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K
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PENTANOLS - HALIDE T T HYDROCARBONS - I .oo
T
HYDROCARBONS
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20
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-20
20
40
A
60
I I I I I I I I PYROCATECHIN - HAUDE HYDROCARBONS
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-20
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30
r
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FORMIC ACID-HAUDE I I HYDROCARBONS
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T FORMIC ACID • HAUDE -HYDROCARBONS
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1 1 11 11 1 1 1 ACETIC ACIO-HALIDE 1 l _ HYDROCARBONS -
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0
20
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60
Figure 3. C-A and 5-|A| Curves for Alcohol-Halide Hydrocarbon, Glycol-Halide Hydrocarbon, Phenol-Halide Hydrocarbon, and Acid-Halide Hydrocarbon Systems J
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
ADVANCES IN CHEMISTRY SERIES
326
3
PROPIONIC ACID] NAUDE-H BUTYRIC ACID [ HYDRO
1 1 1 1 1 1 1 ~ METHANOL - ESTERS
*
y
14 VALERIC ACID J CARBONS
>S
• O
10
20
c
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
40
SO
I A 1
60
PROPIONIC ACID HAUDEBUTYRIC ACID HYDRO- VALERIC ACID CARBON > >
-60
30
-40
-40
0
ft
10
lft20
2ft
I A I
30
0
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I 1 1 1 1 1 METHANOL-ESTERS
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ft
1
10
15
20
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1 1 1 1 1 1 1 ETHANOL• ESTERS
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40
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60
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1 1 1 1 1 1 ~ ETHANOl- ESTERS
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' PROPANOLS • ESTERS
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1 1 1 1 1 1 MITANOLS - ESTERS
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1 1 1 1 1 ESTERS - HEXANOLS
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v 20
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-
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1 L
PROPANOLS [ESTERS ALLYL ALCOHOL
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t
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1 1 1 1 6LYC0L- ESTERS
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c
II 1 1 1 1 1 ~ GLYCEROL-ESTERS
A
II 1 1 II i : GLYCEROL -ESTERS
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1 OXALIC ACID ESTERS MONO- I* BENZOIC ACID ESTERS JPHENOIS {; ACETIC ACID ESTERS
I I I I I I PHENOLS ESTERS I
40
A
6)0
-90-20
Figure 4. C-A and 5-|A| Curves for Acid-Halide Hydrocarbon, Alcohol-Ester, Glycol-Ester, and Phenol-Ester Systems
In AZEOTROPIC DATA; Advances in Chemistry; American Chemical Society: Washington, DC, 1973.
GRAPHICAL METHOD FOR PREDICTING AZEOTROPISM
111
i
METHANOL 1 - ETHANOL PROPANOLS -ETHERS " BUTANOLS
20 c
M
M
30
1
40
M i n i
*
15
Publication Date: June 1, 1973 | doi: 10.1021/ba-1952-0006.ch004
-20
\ \
V
40
&
60
M M 1 PHENOLS • KETONES
i
-60 16
s\ 20
WATER-ETHERS, ACETALS f_
20
\
20
10
0
M
M
a 30
0 -60
J_ 12
40
60
60
100^120
20
40
1 GLYCOL • ETHERS M
-40
-20
M
0
M 11 M M ALCOHOLS •PHENOLS
6
>
c
M
HO
i i 1 GLYCOL • KETONES
s
4
-20
•20
\
0
-40
c
40
6
-60
20
30
40
12 M
I
,AI
60
•V
M
25
60
O -30
HO
20
1
GLYCOL - ETHERS i
HEXANOLS " M M HEPTANOLS -ETHERS
c
ALCOHOLS •ETHERS
-30
1
HEXANOLS-ETHEUS MEPTANOLS-
50 ... 60
M
327
s. 40
60
M
60
tOO . 120
0
15
1 A
M 1
c
; SLYCOL - KETONES
M
M
M
20
25
( A t
30
M
ALCOHOLS •PHENOLS
v
-40
t
M
C
M
-20 M
1 M
1
ALCOHOLS - KETONES
s, 15 C
20
25
1 A 1
30
1 1 1 PHENOLS - KETONES
20 M
M
25
30
1
. ALCOHOLS-KETONES
60
\
40 0 -30
y -20
HO