Hydroquinone
- Formula: C6H6O2
- Molecular weight: 110.1106
- IUPAC Standard InChIKey: QIGBRXMKCJKVMJ-UHFFFAOYSA-N
- CAS Registry Number: 123-31-9
- 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: 1,4-Benzenediol; p-Benzenediol; p-Dihydroxybenzene; p-Dioxybenzene; p-Hydroquinone; p-Hydroxyphenol; Arctuvin; Benzohydroquinone; Benzoquinol; Diak 5; Eldopaque; Eldoquin; Hidroquinone; Hydroquinol; HE 5; Phiaquin; Quinol; Tecquinol; Tenox HQ; 1,4-Dihydroxybenzene; 4-Hydroxyphenol; p-Dioxobenzene; Hydrochinone; Benzene, p-dihydroxy-; Black and White Bleaching Cream; Derma-Blanch; Hydrochinon; Hydroquinole; Idrochinone; NCI-C55834; Tequinol; USAF EK-356; 1,4-Dihydroxy-benzeen; 1,4-Dihydroxy-benzol; 1,4-Dihydroxybenzen; 1,4-Diidrobenzene; UN 2662; Dihydroquinone; Aida; Eldopacque; Eldopaque forte; Eldoquin forte; Solaquin forte; p-Dihydroquinone; Black & White Bleaching Cream; 1,4-Benzenediol (hydroquinone); Artra (Salt/Mix)
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Phase change data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 558.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 558.2 | K | N/A | Krupatkin and Rozhentsova, 1971 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 445.0 | K | N/A | Bret-Dibat and Lichanot, 1989 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 445. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 443.5 | K | N/A | Krupatkin and Rozhentsova, 1971 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 445.98 | K | N/A | Sabbah and Buluku, 1991 | Uncertainty assigned by TRC = 0.03 K; TRC |
Ttriple | 445.5 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.3 K; obtained from cooling curve in absence of air; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 20.2 ± 0.2 | kcal/mol | N/A | Verevkin and Kozlova, 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.50 ± 0.13 | kcal/mol | C | Sabbah and Buluku, 1991, 2 | ΔHfusion =21.09±0.4 kJ/mol; ALS |
ΔsubH° | 22.5 | kcal/mol | N/A | Sabbah and Buluku, 1991, 2 | DRB |
ΔsubH° | 22.5 ± 0.1 | kcal/mol | C | Sabbah and Buluku, 1991, 2 | AC |
ΔsubH° | 23.70 ± 0.40 | kcal/mol | C | Magnus, 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = 24.8 kcal/mol; ALS |
ΔsubH° | 24.800 | kcal/mol | V | Coolidge and Coolidge, 1927 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
558.2 | 0.961 | Weast and Grasselli, 1989 | BS |
558. | 0.961 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.8 | 463. | A | Stephenson and Malanowski, 1987 | Based on data from 448. to 559. K.; AC |
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 |
---|---|---|---|---|---|
432.3 to 559. | 5.8890 | 3049.481 | -40.485 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.04 ± 0.31 | 332. | N/A | Chen, Oja, et al., 2006 | Based on data from 325. to 339. K.; AC |
22.4 ± 0.1 | 334. | C | Sabbah and Buluku, 1991, 2 | AC |
24.21 | 341. to 400. | GS | Bender, Bieling, et al., 1983 | AC |
24.8 ± 0.2 | 342. | ME,TE | de Kruif, 1981 | AC |
24.81 | 313. | N/A | Magnus, 1956 | Based on data from 298. to 346. K.; AC |
23.7 ± 0.4 | 351. | V | Wolf and Weghofer, 1938 | ALS |
24.81 | 326. to 345. | QF | Coolidge and Coolidge, 1927 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.3337 | 444.95 | N/A | Bret-Dibat and Lichanot, 1989, 2 | DH |
6.508 | 445.1 | N/A | Verevkin and Kozlova, 2008 | AC |
6.329 | 453. | N/A | Bret-Dibat and Lichanot, 1989, 2 | AC |
6.4794 | 445.5 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
6.479 | 445.1 | C | Andrews, Lynn, et al., 1926, 2 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14. | 444.95 | Bret-Dibat and Lichanot, 1989, 2 | DH |
14.6 | 445.5 | Andrews, Lynn, et al., 1926, 2 | DH |
IR Spectrum
Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (0.5% IN KBr PELLET); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLID (SPLIT MULL); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Phase change data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1852 |
NIST MS number | 228148 |
References
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Krupatkin and Rozhentsova, 1971
Krupatkin, I.L.; Rozhentsova, E.P.,
Some properties of systems with latent liquid immiscibility,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1700. [all data]
Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A.,
Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee,
Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0
. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Sabbah and Buluku, 1991
Sabbah, R.; Buluku, E.N.L.E.,
Thermodynamic stury of the three isomers of dihydroxybenzene,
Can. J. Chem., 1991, 69, 481. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds,
J. Am. Chem. Soc., 1926, 48, 1274. [all data]
Verevkin and Kozlova, 2008
Verevkin, Sergey P.; Kozlova, Svetlana A.,
Di-hydroxybenzenes: Catechol, resorcinol, and hydroquinone,
Thermochimica Acta, 2008, 471, 1-2, 33-42, https://doi.org/10.1016/j.tca.2008.02.016
. [all data]
Sabbah and Buluku, 1991, 2
Sabbah, R.; Buluku, E.N.L.E.,
Thermodynamic study of three isomers of dihydroxybenzene,
Can. J. Chem., 1991, 69, 481-488. [all data]
Magnus, 1956
Magnus, A.,
Die resonanzenergien der parachinone Aui grund der prazisionsmessungsen ihrer verbrennungswarmen durch herrn gerhard wittwer,
Z. Phys. Chem. (Neue Folge), 1956, 9, 141-161. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Coolidge and Coolidge, 1927
Coolidge, A.S.; Coolidge, M.S.,
The sublimation pressures of substituted quinones and hydroquinones,
J. Am. Chem. Soc., 1927, 49, 100-104. [all data]
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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Chen, Oja, et al., 2006
Chen, Xu; Oja, Vahur; Chan, W. Geoffrey; Hajaligol, Mohammad R.,
Vapor Pressure Characterization of Several Phenolics and Polyhydric Compounds by Knudsen Effusion Method,
J. Chem. Eng. Data, 2006, 51, 2, 386-391, https://doi.org/10.1021/je050293h
. [all data]
Bender, Bieling, et al., 1983
Bender, R.; Bieling, V.; Maurer, G.,
The vapour pressures of solids: anthracene, hydroquinone, and resorcinol,
The Journal of Chemical Thermodynamics, 1983, 15, 6, 585-594, https://doi.org/10.1016/0021-9614(83)90058-7
. [all data]
de Kruif, 1981
de Kruif, C.G.,
Thermodynamic properties of 1,4-benzoquinone (BQ), 1,4-hydroquinone (HQ), 1,4-naphthoquinone (NQ), 1,4-naphthohydroquinone (NHQ), and the complexes BQ--HQ 1:1, NQ--HQ 1:1, NQ--NHQ 2:1, and NQ--NHQ 1:1,
J. Chem. Phys., 1981, 74, 10, 5838, https://doi.org/10.1063/1.440898
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Bret-Dibat and Lichanot, 1989, 2
Bret-Dibat, P.; Lichanot, A.,
Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase,
Thermochim. Acta, 1989, 147(2), 261-271. [all data]
Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Notes
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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