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NATIONAL BUREAU OF STANDARDS REPORT NBS PROJECT
3 16 -1 1-0429 28 Ju l y 1969
NBS REPORT 10 070
SIXTEENTH REPORT ON A SURVEY OF THERMODYNAMIC PROPERTIES OF THE
COMPOUNDS OF THE ELEMENTS CHNOPS
George T. Armstrong and Eugene S. Domalsk i
Progress Report for the Per iod 1 January to 30 June 1969 to
Nat ional Aeronaut ics and Space Administrat ion Contract No. Admendment 4 tcr t 2- 7 J - ~
IMPORTANT NOTICE
NATIONAL BUREAU OF STANDARDS REPORTS are usually preliminary or progress accounting documents intended for use within the Government. Before material in the reports is formally published it is subjected to additional evaluation and review. For this reason, the publication, reprinting, reproduction, or open-literature listing of this Report, either in whole or in part, is not authorized unless permission is obtained in writing from the Office of the Director, National Bureau of Standards, Washington, D.C. 20234. Such permission is not needed, however, by the Government agency for which the Report has been specitically prepared if tnat agency wishes to reproduce additional copies for its own use.
U.S. D E P A R T ~ E ~ T OF COMMERCE NATIONAL BUREAU OF STANDARDS
FOREWORD
A study a t the National Bureau of Standards (NBS), of which t h i s is the s ix t een th progress report , has been undertaken t o meet the need of the National Aeronautics and Space Administration (NASA) f o r thermodynamic information on b io log ica l ly r e l a t e d mater ia l s important t o the space program f o r s eve ra l reasons. Among these reasons are the necess i ty of i n f e r r i n g the maximum account of u se fu l chemistry of incompletely access ib le environments, f o r which only l imited information is ava i lab le , the p o s s i b i l i t y of the occurrence of organic compounds na tu ra l ly synthesized under pr imit ive conditions, and the p o s s i b i l i t y of t h e o r e t i c a l l y recovering part of the pre- b io logica l h i s t o r y of the ear th .
This program i s being carried out under the technica l super- v i s ion of Dr. George Jacobs of NASA, and wi th the consul ta t ion of Dr. Harold Morowitz of the Yale University, Department of Molecular Biology and Biophysics, and Dr. C. W. Beckett of the NBS. cont rac t (Contract No. R-138) w a s i n i t i a t e d 1 May 1964 and extended by Amendments 1, 2, 3, and 4. This r epor t covers a port ion of work under Amendment 4. A s i g n i f i c a n t change i n the d i r e c t i o n of the p ro jec t occurred wi th the i n i t i a t i o n of Amendment 3. The work is now directed toward the presenta t ion of the ma te r i a l i n the form of a Handbook of Thermodynamic Data of I n t e r e s t i n the Biological Sciences. I n t h i s e f f o r t the work a t NES is coordinated wi th a r e l a t e d task a t the Texas A and M Thermodynamic Proper t ies Center under D r . R. A. Wilhoit
The
i
TABLE OF CONTENTS
F o r e w o r d . . . ..................... i
Report of Progress . . . . . . . . . . . . . . . . . . . . . 1 George T. Armstrong
Selected Heats of Combustion and Heats of Formation of Organic Compounds of Biological Interest . . . . . . . . . 2
Eugene So Domalski
ii
Report of Progress
George T. Armstrong
During t h i s report ing i n t e r v a l f u r t h e r progress w a s made on the s e l e c t i o n of hea t s of combustion of organic 'substances re levant t o the program. This work was done l a rge ly by D r , E. S. Domalski and h i s r e s u l t s f o r 115 organic compounds a r e presented as a chapter of t h i s progress report , beginning on page 2.
During t h i s i n t e r v a l arrangements were made t o have much of the tabulated r e s u l t s of t h i s work published by Academic Press, Inc. A manuscript deadline of Ju ly 1970 was accepted.
A por t ion of the funds of t h i s cont rac t are being used t o obtain evaluat ions of thermodynamic propert ies of aqueous so lu t ions of b io log ica l ly important compounds from the Texas A and M Thermodynamics Research Center. D r . R. A. Wilhoit i s the s c i e n t i s t i n charge of t h e i r contributions. This work was i n i t i a t e d i n May 1969. The thermo- dynamics Research Center has submitted t w o monthly progress reports . The f i r s t r epor t s cons i s t of bibl iographies on a c t i v i t y coe f f i c i en t s , partial molal enthalpies , p a r t i a l molal hea t capac i t ies , and osmotic coe f f i c i en t s of the simpler organic ac ids and alcohols.
1
Selected Heats of Combustion and Heats of Formation of
Organic Compounds of Biological I n t e r e s t
Eugene S. Domalski
I. Introduct ion
We r epor t here se lec ted values f o r the hea t s of combustion and
formation a t 298'K for the follawing classes of organic compounds:
a l i p h a t i c hydrocarbons, a l i c y c l i c hydrocarbons, aromatic hydro-
carbons, a l i p h a t i c alcohols, phenols, a l i p h a t i c d i - and polyols,
aldehydes, ketones, n -a l ipha t ic acids , hydroxy a l i p h a t i c ac ids , and
unsaturated a l i p h a t i c acids . The t o t a l number of compounds for which
se lec ted values have been made i n t h i s r epor t i s 115. Adding t o t h i s
t o t a l , the compounds s i m i l a r l y t r ea t ed i n NBS Report 9883 (73 organic
compounds), and NBS Report 9968 (321 organic compounds), we ob ta in
509 f o r a f i n a l t o t a l t o date.
w i l l be processed f o r the next report .
A f i n a l por t ion of about 100 compounds
2
11. Data on the Heats of Combustion and Formt ion of Various Classes of Organic Compounds
Al ipha t ic Hydrocarbons
Compound
methane
ethane
propane
n- bu t ane
n-pentane
n- pen t ane
e thy le ne
acetylene
Compound
cyclopropane
cyclobutane
cyc lope ntane
cyclohexane
cycloheptane
cyclooctane
mg 298OK kca l mol"
-212.80
-372.82
-530.60
-687.64
-845 . 16
-838 . 69
-337 . 23
-310.62
mz 298OK kca l mol-' Reference
-i7.88 1,2,3,32,237,240,243 I -20.23 [ 1,4,32 , 2451
-24.81 [1,4,32,245]
-30.14 [1,41
-34.99 [ 1,4,143 1 -41.46 [1,5,246,248]
+12,50 [1,6,7,32,2,37,242,244,245,252] +54,20 [ 1,8,32,33,244,245,252 I
A l i cyc l i c Hydrocarbons
298OK mg 298OK S ta t e kca l mol"' kcal mol" Reference
3
A r m t i c Hydrocarbons
Compound
benzene
benzene
naphtha le ne naphtha lene anthracene
anthracene
phenanthrene
phenanthrene
pyrene
S ta t e
C
mi 298OK kca l mol-'
. -789 006
-780.96
-1249.4
-1231.8
- 17 14.7 -1687,3
-1706.7
-1685.6
-1873.83
* 298°K kca l mol" Reference
+19.81 [ 1,23-37 I +11.71 [ 1,18,20,38-47 1 +35,6 [48-581
+18.0 [18,42,59-87]
+53.7 [48,55,57,88-921
+29.0 [38,59,60,65,77,
448.4 [48,55,901
+27.3 [38,65,80,83,87,
78,80,83,86,87,93-1001
94-97,99,100]
+27.44 [97,1011
t ri phe ny le ne C -2136.53 +33.72 [99,1011
chrysene C -2137.8 4-35.0 [99,1021
1 , 2- benzanthracene C -2144.0 3.41.2 [991
3,4-benzphenanthrene c -2147.3 444.5 [991
te tracene C -2141.1 -1-38.3 I991
perylene C -2334.60 i43.69 [ 101,103 J f luoranthrene C - 1892.14 4-45 . 75 [ 101,104 J
4
Aliphat ic Alcohols
Compound
methanol
methanol
e t ha no1
ethanol
1-propanol
2-propanol
1- butanol
2- butanol
2-me thyl-1-propanol
2-methyl-2-propanol
1- pentanol
1 - hexano 1
Compound
phenol
pyrocatechol
resorc inol
hydroquinone
o-cre s o l
m-cre s o l
p-cresol
2-e thy1 phenol
3-ethyl phenol
4-ethyl phenol
S ta t e
8
l i q
l i q l i q
l i q
1 i q
l i q
1 i q
l i q
l i q l i q
g
Sta t e
C
C
C
C
C
C
C
C
C
C
q, 298OK kca l molq1
-182.72
- 173.64
-336.86
-326.68
-482 . 75
-479 044
-639.53
-635.90
-637.93
-631 -92
-795.25
-951.70
Phe no1 s
mg, 298 OK k c a l molo1
-729.80
-683.0
-681.30
-681.78
-882 . 72
-885.25
-883 . 99
-1044.07
-1042 . 77
-1040 e 35
5
mgy 298OK kca l mol-' Re f'erence
-47.96 [32,105 , 112,237,238,2391
-57.04 [42,106-1111
-56.19 [32,105,237,239,240,241]
-66.37
-72.66
-75.97
-78.25
-81.88
-79.85
-85 . 86
-84.90
-90.81
mz, 298OK kca l mol-'
-39.45
-86.3
-87 . 95
-87.47
-48 . 90
-46 . 37
-47.63
-49 e 92
-51.22
-53.64
[42,109,111,113-1171
[ 17,42,111,118-1201
[17,111,118-120,126,127] [17,42,111,120-124,2473
111,1211
[17,42,111,118,3.20,121] [17,120,121,128,129]
[17,111, 118,120,123,1251
E 111,123]
Reference
[59,60,63,65, 102,130-1381
[60,102,137]
[60,102,139]
[63,102,134-137, 140-142,144,1451
[ 130-132,1463
[ 130- 132,138,146,147]
[ 130-132,1461
E 1481 11481 11483
Aliphatic Di- and Polyols
Compound
1,2-e thanediol
1,2-propanediol 2,3-propanediol 1,2,3-propanetriol
1,2,3,4-meso-butanetetrol
pentaerythritol xylitol L-arabitol D-mannit ol
(ethylene glycol)
(glycerol)
(me s o-erythri t 01)
dulcit ol
D-perseitol D-gluco-cr- he p t i te
1,lO-decanediol dipentaerythritol
State
1gq
1% lip 1 iq
C
C
C
C
C
C
C
C
C
C
q, 298OK kcal mol''
-284.35
-435 . 8 -431.0 -395 . 65 -500.22
-660.1 -612 . 8 -611.4 -722.97
-720.68
-835 . 2 -840 -4 -1526.20 - 1315 . 1
Mg, 298OR kcal mol'' Reference
-108.70 [98,137,149,1591511
-119 . 6 1150,1521
-124.4 [ 152 1 -159.76 [60,98,115,149,153]
-217.56
-220.0 -267.3 -268 . 7 -319 . 54 -321 . 83 -369.7 -364.5 -165.78 -375 . 9
[60,98,102, 137,155,1561 [ 137,1571
11581 [ 137 1
153,159-1611 [59,60,98,137, 153,1611
[1371 11621 11631 1 164 1
[59,60,98,102,137,
6
Compound
methanal
e thana l
e thana 1
1- p r opanal
2-butanal
1 -pent ana 1
5- hydroxy- 1- pentana 1
paraldehyde
he p t ana 1 octanal
benzaldehyde
salicylaldehyde
C ompound
2-propanone
2 - p r opanone
2-butanone
2- but anone
2 , 3 - but aned i one
3- pentanone
ace tophenone
benzophenone
S t a t e
g
g
l i q
1% 1 i q
l i q 1 i q
l i q
1 i q
l i q 1 i q
1 i q
Aldehydes
&tones
m:y 298 OK kcal m o l - 1
-134.4 -258.01
-278.77
-434.1 -592 . 2
-742
-697 . 1
-810. 0
- 1062.2
-1218 . 9
-843.2
-796.4
S t a t e
g
l i q
g
1 i q
l i q
1 i q
1 i q
C
7
&:, 298'K kcal m01-l
-435 . 32
-427.92
-590.20
-584.17
-493.71
-736.5
-991.60
-1556.2
%!, 298OK k c a l mol"
-28 . 0
-39 . 72
-45 . 96 -53.0 -57 . 3
-70
-114.7 -164.2
-74.4
-80 . 0
-20.0
-66.9
Reference
1165 1 [166,1671
[ 168-171 J 1170-172 3 [ 172,1731
11741
E 175 1 1176-1781
[118,1731
1179 I 1180,1811
f 182-1841
q, 298OK kcal mol" Reference
-51.78 [32,185]
59.18 [ 115,170,171, 186,1871
-59.27 [ 188 1 -65.30 [17,19,189-1g.l]
-87 -44 [ 135,192-194 J -75.3 [17,120,168,195]
-34.07 [196-1991
-8.0 [77,78,127, 198-2011
n-Aliphatic Acids
Compound
methanoic a c i d (formic acid)
e thanoic acid (acetic acid)
propanoic a c i d (propionic acid)
n-butanoic a c i d (n-butyric acid)
n-pentanoic ac id (n-valeric acid)
n-hexanoic ac id (n-caproic acid)
n-heptanoic acid (enanthic ac id)
n-octanoic ac id (capryl ic acid)
n-nonanoic a c i d (pe largonic acid)
n-decanoic acid (capric acid)
n-decanoic a c i d (capric acid)
n-dodecanoic ac id ( l a u r i c acid)
n- dode canoic a c i d ( l a u r i c acid)
S t a t e
l i q
1 i q
1 i q
l i q
1 i q
l i q
l i q
l i q
l i q
1 i q
C
l i q
C
n-tetradecanoic acid l i q
n-tetradecanoic ac id c
n-hexadecanoic a c i d l i q
n-hexadecanoic a c i d c
(myristic acid)
(myristic acid)
(palmitic acid)
(palmitic acid)
mG, 298OK kcal . mol"
-60.86
-209.02
-365.03
-521.87
-678.12
-834.49
-990.81
- 114 7 00
-1303.62
-1460.10
- 1453.07
- 1772.02
- 1763.25
-2084 5 9
-2073.91
-239 7.52
-2384.76
8
2 9 8 O ~ kcal mol"
-1oi.51
-115.71
-122.07
-127.59
-133.71
- 139.7 1
-145.75
-151.93
-157.67
-163.56
- 170.59
-176.37
- 185.14
-188.53
-199 21
-200.34
-213.10
Reference
[113,114,202-205
[ 113,114 , 205- 2 10 I
[209,205,211-2131
[205,212,213]
1205,212-2151
[66,128,205,2141
[ 205,2141
[205,214,216,217]
t205 , 212-214,216,2 17 3
[ 2 14,2 2 2 ]
[60,153,212-2141
1214,2221
[ 154,214-2191
[214,222 3
[59,60,153,154, 214,216-218,2201
1205 , 215,222 1
[60,115,205,212,213, 2 14,2 16 , 2 17,2 20 3
n-Aliphatic Acids (continued)
e, 298OK q, 298'K Compound State kcal molo1 kcal mol" Reference
n-octadecanoic acid l i q -2710.12 -2 12 A7 r 205,214,2221 (stearic acid)
n- octadecanoic acid c -2696 . 12 -226.47 [59,60,62,115,153,205, (stearic acid) 212-214,217,220,221]
(arachidic acid)
(arachidic acid)
n-eicosanoic acid l i q -3022.71 - 224 . 6 1 E 2 14,222 3
n-eicosanoic acid C -3005.50 -241.82 [ 212-2141
n-docosanoic acid C -3337.3 -234 . 8 (behenic acid)
[ 154 1
9
Hydroxy Al ipha t ic Acids
Compound %, 298OK
S t a t e kea1 mol"
g l y c o l i c a c i d C -166.1 (hyd roxyace t i c acid)
(dihydroxyacetic acid) glyoxyl ic a c i d C -125.0
D-lactic ac id C -321.22
DL- lac t i c ac i d C -326 . 8
mesoxalic acid C -128 . 1 DL-@-hydroxybutyric acid l i q -487.2
hydroxyisobutyric ac id c -471.6
l e v u l i n i c ac id C -576.9 (4- ke t ovaler ic acid)
D-gluconic ac id C -594.9
D-galactonic ac id C 589.4
dihydroxybehenic acid c -3235.3
Lwz, 298OK kcal mol ' l
-158.6
-199.7
-165.86
-160.3
-290.7
-162.3
-177.9
-166.6
-379 . 3
-384.8
-336.8
Reference
[102,223]
202,2241
[2251 [ 115 , 2231
E2261
[ 115 1 [223,2271
[2281
10
Unsaturated Al ipha t ic Acids
Compound S t a t e
a c r y l i c a c i d l i q
cis -crotonic ac id 1 i q
t rans-cro t onic a c i d C
t i g l i c ac id C (cis -a, P -d i m e t h y l a c r y l i c acid)
angel ic a c i d C (trans-a, B-dimethylacrylic acid)
so rb ic ac id
hydrosorbic ac id
C
1 i q
undecylenic a c i d C
o l e i c ac id
o l e i c ac id
1 i q
C
e l a i d i c ac id C
e r u c i c ac id C
b r a s s i d i c ac id C
mg, 298'K kca l mol''
-327 -0
-498 -478 2 -626 ,, 2
-634.6
-744 . 2 -795 7 -1579.6
-2675.4 -2667 1 -2636 . 6 -3297.2 -3290.1
m?, 298'K kca l mol"' Reference
-91.8 67,230 1 -83 [2311 -102.9 [1991 -117.3 1199,232 1
-108.9 [ 199,232 1
-93.4 [66,199,2331 -110.2
-138.1 [ 199 1 -178.9 12341 -187.2 [ 115,199,234-2361 -217.7 [199,234,235]
-206 . 5 [ 154,2321 -213.6 [154,2321
11
111. Select ion of the Combustion Jhta
AliDhatic Hvdrocarbons
The hea ts of combustion and formation of. the selected values fo r
the a l i p h a t i c hydrocarbons are the same as those found i n reference 113.
methane - The combustion da ta of Rossini [2,3] were used t o make the
select ion. The e a r l y s tud ies on the heat of combustion of methane by
Andrews [240], Favre and Silbermann 12371, Thomsen 132,2431 and
Berthelot [2441 are of h i s t o r i c a l i n t e r e s t only.
ethane - The combustion da ta of Rossini [4] were used t o make the
se lec t ion .
Matignon 12453 are of h i s t o r i c a l i n t e r e s t only,
The e a r l y s tud ie s by Thomsen [321, and Berthelot and
propane - The combustion da ta of Rossini [4] were used t o make the
se lec t ion .
Matignon 12451 a r e of h i s t o r i c a l i n t e r e s t only.
The e a r l y s tud ies of Thmsen [321, and Berthelot and
n-pentane (E) - The cambustion da ta of Rossini 141 were used t o make
the se lec t ion . The more recent data of P i lcher and Chadwick [1431
are i n very good agreement w i t h the se lec t ion .
n-pentane ( l i q ) - The combustion data of Prosen and Rossini [5] were
used f o r the se lec ted value. The recent da ta of Good [2481 a r e i n
very good agreement with the select ion.
and Macheleidt E2461 w a s not used.
The e a r l i e r work of Roth
ethvlene - The combustion da ta Rossini and Jhuwlton [6], and the heat-
of-hydrogenation data of Kistiakawsky, Romeyn, Ruhoff , Smith, and
Vaughan [7] as corrected by Prosen and Rossini 12491 were used t o
obtain the se lec ted value.
[251] , Favre and Silbermann 12371 , Andrews [242] , Berthelot 12441 , Berthelot and Matignon 12453, Thomsen 1321, and Mixter 12521 are of
h i s t o r i c a l i n t e r e s t only.
The e a r l y s tud ies of Dulong 12501, Grassi
1 2
acetylene - The unpublished combustion da ta of Prosen and Rossini
c i t e d i n Wagman, JSilpatrick, P i tzer , and Rossini [8] w e r e chosen f o r
the se l ec t ed value. The early s t u d i e s of Thomsen [32], Ber the lo t [33,
2441, Ber the lo t and Matignon [245], and E x t e r E2521 are of h i s t o r i c a l
i n t e r e s t only.
Alicvclic Hvdrocarbons
The se l ec t ed values f o r t he hea ts of combustion and formation of
the a l i c y c l i c hydrocarbons are the same as those found i n reference [l].
cyclopropane - The combustion d a t a of Knowlton and Rossini 193 were
chosen i n preference t o the earlier work by Berthelot [244], and
Berthelot and Matignon 1245,2531 . cvclopentane - The Combustion d a t a of Johnson, Prosen, and Rossini
1131 were used i n preference t o the da ta of Kaarsemaker and Coops
[lo], and Spi tzer and Huffman 1121. The wark of Zubov 12541 as corrected
by Swietoslawski [17] i s of h i s t o r i c a l i n t e r e s t only.
cvclohexane - The combustion d a t a of Good and Smith 1201 and Johnson,
Prosen, and Rossini 1131 were used t o make the se lec t ion . The da ta
of Kaarsemaker and Coops [lo], Spi tzer and Huffman 1121, and Moore,
Renquist and Parks [19] were i n good agreement wi th the se lec t ion .
The works of Stohmann and Langbein [14,15], Zubov E161 as corrected by
Swietoslawski 1171, Roth and von Auwers [18] are of h i s t o r i c a l
i n t e r e s t only.
cycloheptane - The combustion da ta of Sp i t ze r and Huffman 1121 and
Kaarsemaker and Coops [lo] were averaged t o obta in the se l ec t ed value.
The d a t a of Zubov [16] as cor rec ted by Swietoslawski 1171 w a s not used.
cyclooctane - The combustion da ta of Kaarsemaker and Coops [lo], and
Sp i t ze r and Huffman [12] were averaged t o ob ta in the se l ec t ed value.
The d a t a of Schlgpfer 1213 and Ruzicka and Schlgpfer 1221 were not used.
13
A r o m a t i c Hvdrocarbons
benzene (E) - References E231 t o 1301 provided experimental d a t a on
the determination of the hea t of vapor iza t ion of benzene.
used the i d e a l hea t of vapor iza t ion a t 25OC df 8.10 k c a l mol
i n reference 113. -780.96 kca l mol , w e ca l cu la t e = -789.06 kca l mol f o r gaseous
benzene.
benzene, re ferences 1321 t o [37] were not used and are of h i s t o r i c a l
i n t e r e s t only . benzene ( E a ) - The combustion d a t a of Good and Smith 1201, and
Prosen, Gilmont, and Rossini [47] were used t o ob ta in the se l ec t ed
value.
were not used.
and are of h i s t o r i c a l i n t e r e s t only.
W e have -1 as
By combining t h e lat ter value with the A€$[C6H6(liq)]= -1 -1
The e a r l y s tud ie s on the heat of combustion of gaseous
The d a t a of Coops, Mulder, Dienske, and Smittenberg 145,463
References 1381 t o 1441 summarize the e a r l y s tud ies ,
naphthalene (E) - The sublimation pressures of naphthalene were
measured by Bradley and Cleasby 1481, Sherwood and Bryant 1491,
Miller [501, Z i l 'berman-Granovskaya 1511, Swan and Mack 1521 , Winstrom
and Kulp 1531, Allen 1541, Hoyer and 'Peperle 1551, Aihara 1561,
Sears and Hopke [571, and Shlyarenko, Martin, and Belyaeva 1581.
p lo t t ed ind iv idua l ly as l og P vs 1/T, these sets of da t a show genera l ly
poor agreement, but when considered as a whole, good agreement r e s u l t s ,
giving a reasonably s t r a i g h t l ine.
the vapor pressure data, w e ob ta in f o r t he heat of sublimation, 17.6
kca l mol-' a t 25OC. H (c)]=
-1231.8 kcal mol-', we ca l cu la t e A€$ = -1249.4 kca l mol
naphthalene.
When
Using a least squares treatment of
Combining t h i s w i th our se lec t ion , w[C 10 8 f o r gaseous -1
14
-ne (cl - The heat of c F b u s t i o n of naphthalene (c) w a s
measured by von Rechenberg 1591, Stohmann 160,611, RUbner [62],
Ber the lo t and Louguinine 1631, Berthelot and Recoura 1641, Berthelot
and Vieille [651, Fischer and Wrede 1661, R i ibe r and Schete l ig 1671,
Wrede [681, Dickinson 1691, Karrar and Fioroni 1711, Verkade and Coops
175,761, Beckers 1771, Bur r i e l 1781, Keffler 1791, Wlone and
Rossignoli 1801, SchlHpfer and Fioroni 1811, Huffman and E l l i s 1821,
Bender and Farber 1831, Speros and Rossini 1841, Prosen and Colomina
1851, Mackle and O ' H a r e [861, and Coleman and Pi lcher 1871. for the heat of combustion of naphthalene r e l a t i v e t o that of benzoic
a c i d w a s well-established by various experimenters as 1.5202 t o
1.5204. For a d iscuss ion of t h i s point see Verkade [741, Verkade,
Coops and Hartman 1731, Swietoslawski 1701, and Swietoslawski and
Starczewska 1723. If we take the value 1.5204, and the present ly
accepted value f o r benzoic a c i d (-nUb=26434 Jg
and apply the appropr ia te co r rec t ions ( fo r standard state condition,
LlnRT and c a l c u l a t i o n of &Hi), w e ob ta in f o r our se lec ted values AH: =
-1231.8 kcal mol-', and Lwp = +18.0 kca l mol-'*
The m l u e
-1 (vacuum) a t 25OC),
anthracene ( ~ 1 - Sublimation pressures have been measured by Bradley and
Cheasby 1481, Stevens 1881, Klochkov 1891, Inokuchi, Shiba, Handa, and
Akamatu 1901, Sears and Hopke 1571, N i t t a , Seki, and Momotani [91],
Kelly and R i c e [921, and Hoyer and Peperle 1551. examining the experimental data, we obtained a se l ec t ed hea t of sub-
l imation of 24.7 kca l mol . By combining the latter wi th
As a r e s u l t of
-1
~ [ C l 4 H l 0 ( c ) 1 = -1687.3 kca l mol-', we ca l cu la t e A€I: = -1714.7 kca l mol -1
f o r gaseous anthracene.
15
anthracene (c) - The heat of combustion of anthracene (c) w a s measured
by von Rechenberg 1591, Stohmann [60], Stohmann, Kleber, and Langbein
[381, Ber the lo t and V i e i l l e [65,100], Beckers [77], Bur r i e l 1781,
Wiegert [93], Klaproth [94], Milone andRossignoli 1803, Fr ies , Walter,
and S c h i l l i n g [95], Shchukarev and Shchukareva [96], Richardson and
Parks [97], Parks, West, Naylor, Fugii, and M c C l a i n e [981, Bender and
Farber 1831, Magnus, Harihann, and Becker 1991, Mackle and O ' H a r e
[86], and Coleman and P i l che r [87]. An average heat of combustion
derived from the da t a of t he last s i x inves t iga t ions [83,86,87,97,
98,991, mentioned c o n s t i t u t e s our se lec ted value.
-1687.3 kca l mol . @[C14Hlo(c) 1 =
-1
phenanthrene (d - Sublimation pressures were measured by Bradley and
Cleasby [48], Inokuchi, Shiba, Handa, and Akamatu 1901, and Hoyer and
Peperle (553.
25OC of 21.1 kca l mol-' from the da ta of Bradley and Cleasby 1481.
By combining AH(sub1imation) wi th ~ [C14H10(c ) ]= -1685.6 kca l mol
w e ca l cu la t e
From these da t a we derived the hea t of sublimation a t
-1 , = -1706.7 kca l mol-' f o r gaseous phenanthrene,
phenanthrene (c) - The heat of combustion of phenanthrene (c) w a s
measured by Stohmann, Kleber, and Iangbein 1381, Berthelot and
Viei l le [65,100], Klaproth 1941, Milone and Rossignoli [80],
Shchukarev and Shchukareva C961, F r i e s? Walter, and Sch i l l i ng [95],
Richardson and Parks [971, Bender and Farber 1831, Magnus, Hartmann
and Becker [99], and Coleman and Pi lcher 1871.
combustion derived from the da ta of the last three inves t iga t ions
[83,87,99], mentioned c o n s t i t u t e s our se lec ted value.
AHz[C H ( c ) ] s -1685.6 kcal mol-l.
An average hea t of
14 10
pvrene - The combustion da ta of Westrum and Wang [loll were prefer red
t o t h a t of Richardson and Parks [97] i n making t h e se lec t ion .
16
tr iphenvlene - The combustiondata of Westrum and Wong [ lo l l were
preferred t o t h a t of Magnus, Hartmann, and Becker [99] i n making the
se l ec t ion .
chrvsene - The combustion d a t a of Magnus, Hartmann, and Eecker 1993
were prefer red t o that of Stohmann 11021 i n making the se lec t ion .
pervlene - The combustion d a t a of Westrum and Wong [ lo l l were pre-
f e r r e d t o t h a t of Pongratz, and Griengl 11033 i n making the se lec t ion .
f luoranthrene - The combustion da ta of Westrum and Wong [ lo l l , and
Boyd, Christensen, and Pua [lo41 were averaged i n obtaining the se l ec t ed
.value e
Al ipha t i c Alcohols
methanol (e;Z - The combustion da ta of Rossini [lo51 on gaseous
methanol were chosen i n preference t o the e a r l y work of Thomsen 1321.
The da ta of Favre and Silbermann [237] are of h i s t o r i c a l i n t e r e s t
only.
measurements of Fiock, Ginnings, and Holton [239], DHvap a t 25OC =
8.95 kcal mol
The heat of vapor iza t ion of methanol a t 25°C w a s taken from the
-1 . Recent vaporization da ta by Wad& [112] are i n very
good agreement wi th the d a t a of Fiock, Ginnings, and Holton 12391.
A co r rec t ion f o r dimer and tetramer formation w a s made t o the vapor-
i z a t i o n da ta using the study of Weltner and P i t z e r [238], amounting
t o 0.13 k c a l mol
process :
-1 . This gives mvap a t 25O= 9.08 kca l mol-' f o r the
CH30H(liq) = C%OH(g, monomer) . methanol ( l i q ) - Our se lec t ed value f o r the hea t of combustion of
CH3(xl(liq) i s obtained by combining the value f o r the hea t of combus-
t i o n of CH30H(g) wi th the heat of vaporization of the l i qu id to the
gaseous monomer. The recent da t a of Chao and Rossini [lll] is i n
good agreement wi th our s e l ec t ion . The earlier work of Stohmann,
17
Kleber, and Langbein [1061, Richards and Davis 1421, Roth [107],
Roth and Banse 11081, Roth and mller 11091 and I. 6. Farbenfabriken
[l lO] has not been used.
etha no1 (e ) - The combustion da ta of Rossini '[105] on gaseous e thanol
were chosen i n preference t o the earlier d a t a of Thomsen [32].
da ta of Andrews 12401 and Favre and Silbermann [237] are only of
h i s t o r i c a l i n t e r e s t . The heat of vapor iza t ion of e thanol a t 25OC
w a s taken from the measurements of Fiock, Ginnings, and Holton [239],
AHvap a t 25OC = 10.13 kca l mol . [112]are i n very good agreement with the d a t a of Fiock, Ginnings,
and Holton [239].
w a s introduced from the d a t a of Coburn, and Grunwald E2411 amounting
to0.05 kca l mol-',
CH3CH20H(g,monomer), Mvap a t 25OC = 10.18 kcal mol
The
-1 Recent vapor iza t ion da ta by Wadsu
A co r rec t ion f o r the presence of dimeric e thanol (g)
ILence, f o r the process: CH CH OH(1iq) = 3 2-1 .
e m - Our s e l e c t i o n f o r the heat of combustion w a s obtained
by combining, the value f o r t he heat of combustion of CH3CH20H(g)
wi th the heat of vaporization of the l i qu id t o the gaseous momomer.
The recent da t a of Chao and Rossini 11111 an? i n good agreement wi th
our se lec t ion .
Emery and Benedict [1151, Atwater and Rosa [116], Atwater and S n e l l
11171, Roth and Muller [lo91 and Richards and Davis [42] wrre not used.
The earlier da ta of Berthelot and Matignon [113,114],
1-propanol - The combustion d a t a of Chao and Rossini [lll] and
Snelson and Skinner [119] were averaged t o ob ta in the se l ec t ed value.
The earlier da t a were not used.
2- proDa no1 - The combustion da ta of Chao and Rossini [lll], Snelson
and Skinner [119], and Parks, Mosley
t o obta in the se l ec t ed value. The earlier d a t a w e r e not used.
and Peterson [190] were averaged
18
l-butanol - The combustion d a t a of Verkade and Coops [123], Chao
and Rossini 11111, Skinner and Snelson 11211, Mosselman and Dekker 12471,
and Gundry, Head, and Lewis E1221 were averaged t o ob ta in the se l ec t ed
value. The e a r l y d a t a of Zubov 11201 and th$l co r rec t ion of the l a t te r
by Swietoslawski [17] was not used.
11241 appeared not negative enough by a t least one k i l o c a l o r i e per
mole, and hence, were not used.
The combustion da ta of Tjebbes
2-butanol - The cambustion d a t a of Chao and Rossini 11111, and Skinner
and Snelson 11211 were averaged t o obta in the se lec t ion .
m thv1-l-DroQanol - The combustion da ta of Chao and Rossini [I111
and Skinner and Snelson 11211 were averaged t o ob ta in the se lec ted
value. The earlier da ta w a s not used.
1-Dentanol - The combustion da ta of Verkade and Coops 11231, Chao and
Rossini 11111, and Gundry, Harrop, Head, and L e w i s [125] were averaged
t o ob ta in the se l ec t ed value. The earlier d a t a w e not used.
l-hexanol - The combustion da ta of Verkade and Coops 11231, and Chao
and Rossini 11111, were averaged t o obta in the se l ec t ed value.
phenol - The hea t of combustion of phenol w a s measured by von Rechenberg
1591, Stohmann 160,1021 Ber the lo t and Louguinine 1431, Berthelot and
Vieille 1651, Andon, Biddiscombe, Cox, Handley, Harrop, Herington, and
Martin 11301, Cox [ 131,1321, Karlsson 11331, Manchester 1 1341, Parks,
Manchester, and Vaughan 11353, Stohmann, Rodatz, and Herzberg 11361,
Stohmann and Langbein 11371, and Badoche 11381. of Andon, e t al. 11301 f o r our se lec ted value.
W e have used the da t a
19
Pvrocaterhol - The combustion da ta of &Stohmann 11021, and Stohmann and
Langbein [137] were obtained using an oxygen bomb calorimeter, and
are prefer red t o the d a t a of Stohmarm 1601 i n which the potassium
chlorate-oxidative mixture technique was used. The d a t a i n re ferences
11021 and 11371 are the same. The heat of combustion ca lcu la ted from
the latter w a s found t o be -684.9 kca l mol-' a f t e r a l l ca r r ec t ions were
applied.
the heat of combustion of phenol found by Stohmann and Langbeinwas 2
t o 3 kca l mol-' more negative than our present ly se l ec t ed value f o r
phenol.
This w a s reduced t o -683.0 kca l mol-'. because the value f o r
r e so rc ino l - The combustion d a t a of Desai, Wilhoit, and Zwolinski
11391 w a s chosen i n preference t o the earlier combustion data.
hvdroquinone - The combustion d a t a of P i l che r and Sutton 11421 w a s
chosen i n preference t o any o ther combustion data.
o -creso l - The combustion da ta of Andon, Biddiscombe, Cox, Handley,
Harrop, Herington, and Martin 11301, and Cox 1131,1321 were chosen
i n preference t o the data of Stohrnann, Rodatz, and Herzberg 11461.
m-cresol - The combustion d a t a of Andon, Biddiscombe, Cox, Handley,
Harrop, Herington, and Martin 11301, and Cox 1131,1321 were chosen
i n preference t o the earlier data.
p-cresol - The combustion da ta of Andon, Biddiscombe, Cox, Handley,
Harrop, Herington, and Martin 11301, and C o x 1131,1321 were chosen
i n preference t o the da ta of Stohmann, Rodatz and Herzberg 11461.
20
Aliphat ic D i - and Polvols
1.2-ethanediol. (ethylene p l v c o l l - The combustion d a t a of Parks,
West, Naylor, F u j i i , and McClaine 1981 were preferred f o r the
se lec ted value t o the earlier data.
1 , 2 - ~ r o ~ a n e d i o l - The combustion da ta of Moureu and Dode [150] were
preferred t o that of Louguinine [152].
1.2 .3-uro~enet r io l . (e lvcerol) - The combustion data of Parks, West,
Naylor, F u j i i , and McClaine [981 were chosen i n preference t o the
earlier combustion data .
1.2.3,4-meso-butanetetrol. (meso-erythritol) - The combustion da ta of
Parks, West, Naylor, F u j i i , and M c C l a i n e 1981 were chosen i n preference
t o the e a r l i e r combustion da ta ,
p e n t a e r y t h r i t o l - The combustion da ta of Medard and Thomas 11571 were
preferred t o the da ta of Stohmann [137]-,
D-manni tol, - The combustion data
M c C l a i n e [98] were preferred t o any data published before 1900 ( references [59,60,102,137,153,159,161]). The recent combustion d a t a .
of Baer and Flehmig [160] are i n poor agreement with our se lec ted value
by 6 t o 7 kca l m o l and the 6 t o 7 kca l mol-' could be the ove ra l l uncer ta in ty i n the
experiment .
of Parks, West, Naylor, F u j i i and
-1 Details of t h e i r ca lo r ime t r i c da ta are scant,
d u l c i t o l
McClaine
- The combustion da ta of Parks, West, Naylor, F u j i i , and
[98] were chosen' i n preference t o the earlier cambustion data.
21
Alde hvde s
e thana l (E) - The heat-of-hydrogenation da ta .of Dolliver, Gresham,
Kistiakmsky, Smith, and Vaughan [167] w a s used as the b a s i s of our
s e l ec t ed value rather than the e a r l y combustion of Ber the lo t and
T)gier 11661 . i e t b n a l (1 - The heat of vapor iza t ion of e thana l as determined by
-1 Coleman and DeVries [169], 6.24 kcal mol the heat of formation of gaseous ethanal. The combustion d a t a of
Berthelot andDelepine [170,171], and Roth and mller C1681 was not
used,
a t 25OC, was combined with
1-propanal - The combustion d a t a of Tjebbes 11721 were used t o obta in
the se lec t ion . The d a t a of Berthelot and Delepine [170,171] were not
used.
1-butanal - The combustion d a t a of Tjebbes 11721 and Nicholson [173]
were averaged t o make the se lec t ion .
paraldehvde - The combustion d a t a of Fletcher, Mortimer, and Spr inga l l
E1781 were used t o obta in the se lec ted value. The same da ta are given
earlier by Cass, Spr inga l l , and White [1771, but shuw AI@ t o be more
negative by 0.2 kca l mol . The combustion d a t a of Louguinine 11763
were not used.
-1
heptanal - The combustion da ta of Nicholson [173] were chosen i n pre-
ference t o the da t a of Louguinine 11181,
benzaldehvde - The combustion d a t a of Landrieu, Baylocq, and Johnson
[180] were chosen i n preference to the da t a of Stohmann, Rodatz, and
Herzberg [18110
22
salicvlaldehvde - The combustion da ta of Delepine and Riva ls [182] were
chosen i n preference t o the da ta of Ber the lo t and Rivals [183] and
Rivals [184].
Ketones
2 - pr opanone (a ) - The combustion da ta of Miles and Hunt [185] were chosen i n preference t o the e a r l y data of Thomsen [32l0
2-propanone ( l i q ) - The heat of vaporization was taken from the da ta
of Pennington and Kobe [187], AH&p a$ 25OC = 7.40 kca l mol
lat ter value was combined wi th the heat of combustion of gaseous
2-propanone. The combustion da ta of Berthelot and Delepine [170,171],
Emery and Benedict [115], and Taylor, H a l l , and Thomas [186]were not
used.
-1 . The
2-butanone (lh) - The combustion d a t a of Sinke and Oetting [191]
were chosen i n preference to any previous work.
2.3-butanedione - The combustion da ta of Nicholson, Szwarc, and Taylor
11931, and Parks, Manchester, and Vaughan 11351 were averaged t o make
the se lec t ion .
[192] were not used.
The da ta of Spr inga l l and White 11941 and Landrieu
3-pentanone - The combustion da ta of Roth and Mller 11681 and
Louguinine [195] w e r e averaged t o obta in the se lec ted value. The
da ta of Zubov [12.0] as c m r e c t e d by SwietosLawski [17] were not used.
acetophenone - The combustion da ta of Colomina, Latorre, and Perez-
Ossorio [196,197] were chosen i n preference t o the e a r l y combustion
da ta of Stohmann [1991 , and Stohmann, Rodatz, and Herzberg 11981 . 23
benzoDhenone - The combustion da ta of Colcnnina, Cambeiro, Perez-Ossorio,
and Latorre [200], and Parks, Mosley, and Peterson [127] were averaged
f o r the se lec t ion .
and Blatt [201], Stohmann, Rodatz, and Herzberg [198], and Stohmann
[199] were not used.
The d a t a of Beckers [77], Bur r i e l [781, Landrieu,
n-Aliphat ic Acids
methanoic acid. (formic a c i d 1 - The combustion d a t a of Sinke [204] were used t o obta in the se l ec t ed value. The da ta of Lebedeva [205l are i n
exce l l en t agreement wi th the se lec t ion . The da ta of Berthelot [2021, Berthelot and Matignon [113,114], and Jahn [203] were not used,
ethanoic acid. (acetic acid) - The combustion da ta of Evans and Skinner
[206] were used t o obta in the se lec ted value. The da ta of Lebedeva
[205] a r e i n exce l l en t agreement with the se l ec t ion .
Ber the lo t and Matignon [113,114] , Roth E2071 , Schjanberg [208,2091 and S t u l l [210] were not used, although only the da ta of Roth [2071
-1 appeared t o devia te from the s e l e c t i o n by more than 0.3 kcal mol
The d a t a of
propanoic acid. (propionic acid) - The combustion d a t a of Lebedeva
[2051 were chosen i n preference t o the previous data.
n-butanoic acid. (n-butvric ac id) - The combustion da ta of Lebedeva
[2051 were chosen i n preference t o the e a r l y data.
n-pentanoic ac id , (n-valeric ac id) - The combustion da ta of kbedeva
[2051, and Adriaanse, Dekker, and Coops [214] w e r e averaged t o obta in
the se l ec t ed value.
w e l l w i th the e a r l y work of Stohmann, Kleber, Langbein, and Offenbauer
1212,2131,
The da ta of Hancock, Watson, and Gilby 12151 agree
Data from the la t ter three re ferences were not used.
24
n-hexanoic a c i d , (n-caproic a c i d 1 - The combustion da ta of Lebedeva
[205], and Adriaanse, Dekker, and Coops 12141 were averaged t o obta in
the se l ec t ed value.
[128] were not used.
The da ta of Fischer and Wrede 1661, and Louguinine
n-heptanoic acid. (enanthic ac id) - The combustion da ta of Iebedeva
[2051, and Adriaanse, Dekker, and Coops 12143 were averaged t o obta in
the se l ec t ion .
n-octanoic ac id . (caprvlic acid). - The combustion d a t a of Lebedeva
12051 and Adriaanse, Dekker, and Coops [214] were averaged t o obta in
the selected value. The da ta of Louguinine [216,217] were not used.
n-nonanoic acid. (PelarPonic acid) - The combustion da ta of Lebedeva
12051, and Adriaanse, Dekker, and Coops 12141 were averaged t o obta in
the se lec t ion . The e a r l y d a t a [212,213,216,217] were not used.
n-deca noic acid. (car, r i c acid)(c) - The combustion da ta of Adriaanse,
Dekker, and Coops 12141 w e r e chosen i n preference t o the earlier data.
n-dodecanoic ac id . ( l a u r i c ac id) (c) - The Combustion da ta of Adriaanse,
Dekker, and Coops [2141 were chosen i n preference t o the earlier data.
n-tetradecanoic ac id , (MY r i s t ic acid)(c) - The combustion d a t a of
Adriaanse, Dekker, and Coops C2141 w a s used t o ob ta in the se l ec t ed
value. The d a t a of Swain, S i l b e r t , and Mi l le r [220], although not
as precise, are i n good agreement wi th the se lec t ion .
combustion d a t a [59,60,153,154,216,217,218] w e r e not used.
The e a r l y
n-hexadecanoic ac id . (polmitic ac id) ( l iq ) - The hea t of fus ion as
determined by Adriaanse, Dekker, and Coops [214,222] was s e l ec t ed i n
preference t o the da t a of Lebedeva [205],
25
n-hexadecanoic ac id . (pa l m i t i c acid)(c) - The combustion da ta of
Adriaanse, Dekker, and Coops 12141 were used t o obta in the se lec ted
value i n preference t o the da ta of Lebedeva 22053. The da ta of
Swain, S i l b e r t , and Miller 12201, although not as precise as e i t h e r
of the above da ta i s i n good agreement wi th the da ta of Adriaanse,
Dekker and Coops 12141. Data p r io r t o the above [60,115,212,213,
216,2171 were not used.
n-octade,canoic ac id , (stearic ac id) I l i a ) - The fus ion da ta of
Lebedeva 12051, and Adriaanse, Dekker, and Coops 1214,2221 were
averaged t o obta in the se lec ted value, AH(fusion) a t 25OC = 14.0 kea1
m o l . -1
n-octadecanoic ac id . (st earic acid) (d - The combustion da ta of
Lebedeva 12051, and Adriaanse, Dekker, and Coops 12141 were averaged
t o obta in the se l ec t ed value.
and Miller [220] are too pos i t i ve by about 2.2 kca l mol-',
t o the above 159,60,62,115,153,212,213,217,221] were not used.
The combustion d a t a of Swain, S i l b e r t ,
Data p r i o r
n-eicosanoic ac id . (arachidic acid) (c) - The combustion da ta of Adriaanse,
Dekker, and Coops 12141 were preferred t o the earlier work.
Wydroxv Al ipha t ic Acids
g l v c o l i c acid. (hydroxvacetic acid1 - The combustion da ta of Louguinine
12231, and Stohmann [102]were averaged t o obta in the selected value.
g lyoxyl ic acid. (dihydroxvacetic acid') - The combustion data of
Berthelot 12021 are t h e same as Berthelot and Matignon 12241.
DL-lactic a c i d - The combustion da ta of Emery and Benedict 11151 and
Louguinine [223] were averaged t o obtain the se l ec t ed value.
26
hvdroxvisobutvric ac id - The later combustion d a t a of Louguinine [223]
w a s preferred t o the earlier work by the same author [2271.
Unsaturated Al ipha t ic Acids
acrylic ac id - The combustion da ta of Moureu and Boutaric [230], and
Riiber and Schete l ig 1671 were averaged t o ob ta in the se lec ted value.
t i e l i c ac id - The combustion da ta of Stohmann I1991 and Stohmann
[232] are the same.
angel ic ac id - The combustion da ta of Stohmann [199] and Stohmann
[232] are the same.
so rb ic ac id - The combustion da ta of Fischer and Wrede 1661 were chosen i n preference t o the da ta of Stohmann [199] and Osipov [233].
o l e i c ac id (c> - The combustion data of Keff le r and McLean E2361 were
chosen i n preference t o previous data.
e la idic acid - The combustion da ta of Keffler [234,235] were chosen i n
preference t o the data of Stohmann [199].
e ruc ic ac id - The combustion da ta of Stohmann and Iangbein [154] are the same as Stohmann [2321.
b r a s s i d i c ac id -- The combustion da ta of Stohmann and Langbeing [154] are the same as Stohmann [232],
27
IV. References
[ 11 "Selected Values of Hydrocarbons and Related Compounds", American Petroleum I n s t i t u t e Research Pro jec t 44, Thermodynamics Research Center, Texas A and M University, College Station, Texas (Loose- leaf da ta shee ts , ex t an t 1969).
[2]
[3]
Rossini, F. D., J. Research NBS 5, 37-49 (1931).
Rossini, F. D., J. Research NBS L, 329-330 (1931).
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