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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Phase change data
Go To: Top, 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 | Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 395.52 | K | N/A | Furukawa, McCoskey, et al., 1951 | 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, 2 | DH |
4.3021 | 395.52 | N/A | Furukawa, McCoskey, et al., 1951, 2 | 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, 2 | DH |
10.88 | 395.52 | Furukawa, McCoskey, et al., 1951, 2 | 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, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
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Calibrants for thermal analysis. measurement of their enthalpies of fusion by adiabatic calorimetry.,
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Ginnings, D.C.; Furukawa, G.T.,
Heat Capacity Standards for the Range 14 to 1200 K,
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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 410 K,
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Vapor pressure measurements in carrier gas containing ligand vapor using the transpiration technique,
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Klosky, Simon; Woo, Leo P.L.; Flanigan, Robert J.,
THE VAPOR-PRESSURE CURVE OF BENZOIC ACID,
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Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
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The design, construction, and testing of a new Knudsen effusion apparatus,
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Vapour pressures and enthalpies of sublimation of naphthalene and benzoic acid,
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de Kruif, C.G.; Blok, J.G.,
The vapour pressure of benzoic acid,
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Construction and testing of a sublimation calorimetric system using a Calvet microcalorimeter,
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A re-evaluation of the enthalpy of sublimation of some metal acetylacetonate complexes,
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DeKruif, van Ginkel, et al., 1975
DeKruif, C.G.; van Ginkel, C.H.D.; Voogd, J.,
Torsion-effusion vapour pressure measurements of organic compounds,
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Arshadi, Mohammed R.,
Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method,
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de Kruif, C.G.; Oonk, H.A.J.,
The determination of enthalpies of sublimation by means of thermal conductivity manometers,
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Malaspina, 1973
Malaspina, L.,
Microcalorimetric determination of the enthalpy of sublimation of benzoic acid and anthracene,
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Wiedemann, 1972
Wiedemann, H.G.,
Applications of thermogravimetry for vapor pressure determination,
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Ashcroft, 1971
Ashcroft, S.J.,
The measurement of enthalpies of sublimation by thermogravimetry,
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Vapour pressures of the tris(acetylacetonato) complexes of scandium(III), vanadium(III) and chromium(III),
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Mertl, I.,
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Davies, M.; Kybett, B.,
Sublimation and vaporization heats of long-chain alcohols,
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Uber sublimationswarmen,
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Hirsbrunner, 1934
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Uber das gleichgewicht der thermischen dissoziation der salicylsaure,
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Heat capacity standards for the range 14 to 1200°K,
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Furukawa, McCoskey, et al., 1951, 2
Furukawa, G.T.; McCoskey, R.E.; King, G.J.,
Calorimetric properties of benzoic acid from 0 to 410K,
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Brittain, Harry G.,
Vibrational Spectroscopic Studies of Cocrystals and Salts. 2. The Benzylamine-Benzoic Acid System,
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Deviations of binary organic eutectic melt systems,
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Thermodynamic Properties of Aqueous Sodium Chloride Solutions,
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Pacor, 1967
Pacor, P.,
Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis,
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Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
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David, 1964
David, D.J.,
Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters,
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Andon and Connett, 1980, 2
Andon, R.J.L.; Connett, J.E.,
Calibrants for thermal analysis. Measurement of their enthalpies of fusion by adiabatic calorimetry,
Thermochim. Acta, 1980, 42, 241-247. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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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