Benzoic acid
- Formula: C7H6O2
- Molecular weight: 122.1213
- IUPAC Standard InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-N
- CAS Registry Number: 65-85-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Benzenecarboxylic acid; Benzeneformic acid; Benzenemethanoic acid; Benzoesaeure GK; Benzoesaeure GV; Carboxybenzene; Dracylic acid; Phenylcarboxylic acid; Phenylformic acid; Retarder BA; Retardex; Salvo, liquid; Solvo, powder; Tenn-Plas; Acide benzoique; Benzoic acid, tech.; Kyselina benzoova; Benzoesaeure; Salvo powder; E 210; HA 1; HA 1 (acid); Phenylcarboxy; Benzenemethonic acid; Diacylic acid; Flowers of benjamin; Flowers of benzoin; Oracylic acid; Retarder BAX; NSC 149
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Condensed phase thermochemistry data
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -771.272 ± 0.048 | kcal/mol | Ccb | Gundry, Harrop, et al., 1969 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -770.968 kcal/mol; Corresponding ΔfHºliquid = -92.032 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -91.98 ± 0.12 | kcal/mol | Ccb | Corral, 1960 | ALS |
ΔfH°solid | -92.2 | kcal/mol | Ccb | Landrieu, Baylocq, et al., 1929 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -772. ± 1. | kcal/mol | AVG | N/A | Average of 17 out of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 39.606 | cal/mol*K | N/A | Kaji, Tochigi, et al., 1993 | DH |
S°solid,1 bar | 40.088 | cal/mol*K | N/A | Arvidsson, Falk, et al., 1976 | DH |
S°solid,1 bar | 40.055 | cal/mol*K | N/A | Furukawa, McCoskey, et al., 1951 | DH |
S°solid,1 bar | 40.110 | cal/mol*K | N/A | Davies and Staveley, 1957 | DH |
S°solid,1 bar | 40.80 | cal/mol*K | N/A | Parks, Huffman, et al., 1933 | Extrapolation below 90 K, 59.25 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
61.9 | 413. | Pacor, 1967 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
35.320 | 300. | Kaji, Tochigi, et al., 1993 | T = 19 to 312 K. Unsmoothed experimental datum.; DH |
35.141 | 298.902 | Sorai, Kaji, et al., 1992 | T = 15 to 305 K. Unsmoothed experimental datum.; DH |
34.950 | 296.29 | Moriya, Matsuo, et al., 1982 | T = 13 to 355 K. NBS SRM 29.; DH |
35.050 | 298.15 | Shakirov and Lyubarskii, 1980 | T = 20 to 300 K.; DH |
35.084 | 298.15 | Arvidsson, Falk, et al., 1976 | T = 6 to 341 K.; DH |
35.151 | 299.62 | Tatsumi, Matsuo, et al., 1975 | T = 12 to 304 K.; DH |
35.6 | 301. | Mosselman, Mourik, et al., 1974 | One temperature, T = 5 K. Value 5 J/mol*K.; DH |
35.086 | 298.15 | Konicek, Suurkuusk, et al., 1971 | DH |
40.010 | 298.15 | Justice, 1969 | As check on system. Only value at 298 K given.; DH |
35.167 | 299.99 | Suga and Seki, 1965 | T = 13 to 300 K. Value is unsmoothed experimental datum.; DH |
31.1 | 340. | David, 1964 | T = 298 to 373 K. Mean value. T = uncertain.; DH |
34.969 | 298.15 | Kolesov, Seregin, et al., 1962 | T = 22 to 310 K.; DH |
35.139 | 298.15 | Davies and Staveley, 1957 | T = 20 to 298 K.; DH |
35.801 | 298.15 | Popov and Kolesov, 1956 | T = 80 to 300 K.; DH |
35.088 | 298.15 | Ginnings and Furukawa, 1953 | T = 14 to 410 K.; DH |
35.088 | 298.15 | Furukawa, McCoskey, et al., 1951 | T = 13 to 410 K.; DH |
38.29 | 323. | Satoh and Sogabe, 1939 | T = 0 to 100 C. Mean value.; DH |
34.680 | 295.1 | Parks, Huffman, et al., 1933 | T = 93 to 295 K. Value is unsmoothed experimental datum.; DH |
37.09 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 200 C.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 522.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 522. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 523.18 | K | N/A | Burriel, 1931 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 523.59 | K | N/A | Burriel, 1931 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 395.2 ± 0.7 | K | AVG | N/A | Average of 18 out of 20 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 395.52 | K | N/A | Marsh, 1987 | Uncertainty assigned by TRC = 0.005 K; recommended as calibration standard; TRC |
Ttriple | 395.520 | K | N/A | Andon and Connett, 1980 | Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 395.52 | K | N/A | Ginnings and Furukawa, 1953, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 395.52 | K | N/A | Furukawa, McCoskey, et al., 1951, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 18.9 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 353. to 393. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 21.4 ± 0.9 | kcal/mol | AVG | N/A | Average of 13 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
406.2 | 0.013 | Weast and Grasselli, 1989 | BS |
406. | 0.013 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.901 | 335. | N/A | Torres-Gomez, Barreiro-Rodriguez, et al., 1988 | DH |
15.1 ± 0.1 | 401. to 416. | N/A | Pena, Ribet, et al., 2003 | AC |
15.8 | 420. | A | Stephenson and Malanowski, 1987 | Based on data from 405. to 523. K.; AC |
16.2 | 368. to 428. | GS | Matsubara and Kuwamoto, 1985 | AC |
15.6 | 428. | I | Cramer, 1943 | AC |
16.2 | 416. | MM,A | Klosky, Woo, et al., 1927 | Based on data from 401. to 520. K.; AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.38 | 335. | Torres-Gomez, Barreiro-Rodriguez, et al., 1988 | DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369. to 522.4 | 4.47263 | 1771.357 | -127.484 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.326 | 298.15 | N/A | Torres-Gomez, Barreiro-Rodriguez, et al., 1988 | DH |
21.7 ± 0.48 | 340. to 410. | TG-TS | Selvakumar, Raghunathan, et al., 2009 | AC |
21.5 ± 0.1 | 307. | ME | Ribeiro da Silva, Monte, et al., 2006 | Based on data from 299. to 317. K.; AC |
22.1 ± 1. | 294. to 331. | ME | Ginkel, Kruif, et al., 2001 | AC |
21.6 ± 0.07 | 323. to 394. | GS | Zielenkiewicz, Perlovich, et al., 1999 | AC |
20.7 | 313. to 343. | TGA | Elder, 1997 | AC |
21.2 ± 0.2 | 311. | ME | Da Silva and Monte, 1990 | Based on data from 307. to 314. K.; AC |
20.9 ± 0.07 | 335. | C | Torres-Gomez, Barreiro-Rodriguez, et al., 1988 | AC |
21.7 ± 0.1 | 306. | QR | Glukhova, Arkhangelova, et al., 1985 | Based on data from 293. to 319. K.; AC |
22.7 ± 0.43 | 294. | N/A | Kaisersberger, Hädrich, et al., 1985 | AC |
21.0 | 368. to 428. | GS | Matsubara and Kuwamoto, 1985 | AC |
21.7 ± 0.5 | 293. to 313. | ME | Colomina, Jimenez, et al., 1982 | AC |
21.4 ± 0.01 | 353. | DM | de Kruif and Blok, 1982 | Based on data from 316. to 391. K.; AC |
21.3 ± 0.05 | 320. to 370. | C | Murata, Sakiyama, et al., 1982 | AC |
20. ± 0.5 | 369. | SG | Sachinidis and Hill, 1980 | Based on data from 344. to 395. K.; AC |
21.1 ± 0.69 | 281. to 323. | LE | Nowak, Szczepaniak, et al., 1978 | AC |
21.2 ± 0.38 | 293. to 318. | TE | DeKruif, van Ginkel, et al., 1975 | AC |
22.2 ± 0.05 | 296. | ME | Arshadi, 1974 | Based on data from 273. to 318. K.; AC |
21.1 ± 0.05 | 293. to 311. | TCM | de Kruif and Oonk, 1973 | AC |
21.3 ± 0.1 | 338. to 383. | ME | Malaspina, 1973 | AC |
21.3 ± 0.1 | 338. to 383. | C | Malaspina, 1973 | AC |
22. ± 0.07 | 293. to 308. | ME | Colomina, Monzon, et al., 1972 | AC |
20.7 ± 0.31 | 290. to 315. | ME,C | Wiedemann, 1972 | AC |
21.3 | 314. | N/A | Ashcroft, 1971 | Based on data from 299. to 329. K.; AC |
21.6 ± 0.2 | 367. | HSA | Melia and Merrifield, 1970 | Based on data from 324. to 392. K.; AC |
20.7 ± 0.41 | 303. | ME | Wiedemann and Waughna, 1970 | Based on data from 290. to 315. K. See also Zielenkiewicz, Perlovich, et al., 1999.; AC |
21.2 ± 0.1 | 363. | GS | Mertl, 1968 | Based on data from 348. to 378. K.; AC |
21.7 | 299. | ME | Davies and Kybett, 1965 | Based on data from 291. to 307. K.; AC |
20.1 ± 0.2 | 318. | TE | Wolf and Weghofer, 1938 | AC |
20.1 ± 0.2 | 318. | V | Wolf and Weghofer, 1938, 2 | ALS |
20.5 | 383. | T | Hirsbrunner, 1934 | Based on data from 333. to 389. K.; AC |
20.2 ± 0.1 | 364. | I | Klosky, Woo, et al., 1927 | Based on data from 377. to 394. K.; AC |
Entropy of sublimation
ΔsubS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
71.53 | 298.15 | Torres-Gomez, Barreiro-Rodriguez, et al., 1988 | DH |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.3035 | 395.52 | N/A | Ginnings and Furukawa, 1953 | DH |
4.3021 | 395.52 | N/A | Furukawa, McCoskey, et al., 1951 | DH |
4.061 | 396.9 | DSC | Brittain, 2009 | AC |
4.13 | 394.4 | DSC | Sharma, Kant, et al., 2003 | See also Sharma, Jamwal, et al., 2004.; AC |
4.09 | 395.4 | DSC | Roy, Riga, et al., 2002 | AC |
4.300 | 395.5 | N/A | Pitzer, Peiper, et al., 1984 | AC |
3.8791 | 395. | N/A | Pacor, 1967 | DH |
4.1396 | 395.0 | N/A | Andrews, Lynn, et al., 1926 | DH |
4.1587 | 395. | N/A | David, 1964 | Temperature not measured.; DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.88 | 395.52 | Ginnings and Furukawa, 1953 | DH |
10.88 | 395.52 | Furukawa, McCoskey, et al., 1951 | DH |
9.82 | 395. | Pacor, 1967 | DH |
10.5 | 395.0 | Andrews, Lynn, et al., 1926 | DH |
11. | 395. | David, 1964 | Temperature; DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
4.3169 | 395.527 | crystaline, I | liquid | Andon and Connett, 1980, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.92 | 395.527 | crystaline, I | liquid | Andon and Connett, 1980, 2 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gundry, Harrop, et al., 1969
Gundry, H.A.; Harrop, D.; Head, A.J.; Lewis, G.B.,
Thermodynamic properties of organic oxygen compounds. 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol,
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Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Corral, 1960
Corral, L.B.,
Investigaciones termoquimicas sobre los acidos toluicos y dimetilbenzoicos,
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Landrieu, Baylocq, et al., 1929
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Etude thermochimique dans la serie furanique,
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Kaji, Tochigi, et al., 1993
Kaji, K.; Tochigi, K.; Misawa, Y.; Suzuki, T.,
An adiabatic calorimeter for samples of mass less than 0.1 g and heat capacity measurements on benzoic acid at temperatures from 19 K to 312 K,
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Arvidsson, Falk, et al., 1976
Arvidsson, K.; Falk, B.; Sunner, S.,
A small sample low temperature adiabatic heat capacity calorimeter with an automatic data acquisition system,
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Furukawa, McCoskey, et al., 1951
Furukawa, G.T.; McCoskey, R.E.; King, G.J.,
Calorimetric properties of benzoic acid from 0 to 410K,
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Davies and Staveley, 1957
Davies, T.; Staveley, L.A.K.,
The behaviour of the ammonium ion in the ammonium salt of tetraphenylboron by comparison of the heat capacities of the ammonium, rubidium, and potassium salts,
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Thermal data on organic compounds. XI. The heat capacities,
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Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis,
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An automated adiabatic calorimeter for the temperature range 13 K to 530 K The heat capacities for benzoic acid from 15 K to 305 K and of synthetic sapphire from 60 K to 505 K,
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Low temperature adiabatic calorimeter with a built-in cryo-refrigerator,
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An adiabatic calorimeter for high-resolution heat capacity measurements in the temperature range from 12 to 300 K,
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A precise drop heat capacity calorimeter for small samples,
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Adiabatic calorimeter of small volume for the determination of true heat capacity over the range 12-340K,
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Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
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Sublimation and vaporisation processes of S(-) efaroxan hydrochloride,
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Vapor pressure measurements in carrier gas containing ligand vapor using the transpiration technique,
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THE VAPOR-PRESSURE CURVE OF BENZOIC ACID,
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Vapor Pressure Measurements of Sc(tmhd) 3 and Synthesis of Stabilized Zirconia Thin Films by Hybrid CVD Technique Using Sc(tmhd) 3 , Zr(tmhd) 4 , and Al(acac) 3 [tmhd, 2,2,6,6-tetramethyl-3,5-heptanedione; acac, 2,4-pentanedione] as Precursors,
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The need for temperature control in effusion experiments (and application to heat of sublimation determination),
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Sublimation measurements of pharmaceutical compounds by isothermal thermogravivletry,
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Notes
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- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔsubS Entropy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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