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, Gas phase ion energetics data, Gas Chromatography, 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 |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H6O2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.94 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.93 ± 0.01 | S | Oikawa, Abe, et al., 1985 | LBLHLM |
7.95 ± 0.05 | PI | Potapov, Kardash, et al., 1972 | LLK |
7.95 ± 0.03 | PI | Potapov and Sorokin, 1971 | LLK |
8.44 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
De-protonation reactions
C6H5O2- + =
By formula: C6H5O2- + H+ = C6H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 350.4 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 343.1 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-1 | 180. | 1327. | Radecki and Grzybowski, 1978 | Chromosorb W HMDS (100-120 mesh); Column length: 2.1 m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1334. | Grzybowski, Lamparczyk, et al., 1980 | Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 2693. | Shiratsuchi, Shimoda, et al., 1993 | 60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min |
Capillary | DB-Wax | 2693. | Shiratsuchi, Shimoda, et al., 1993 | 60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1241. | Xian, Chen, et al., 2006 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (3 min) 6 0C/min -> 150 0C (1 min) 10 0C/min -> 250 0C (10 min) |
Capillary | SE-30 | 1334. | Peterson, 1992 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 220.6 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | DB-5 | 207.49 | Williams and Horne, 1995 | He, 60. C @ 2. min, 5. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tend: 270. C |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, 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
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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,
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Verevkin and Kozlova, 2008
Verevkin, Sergey P.; Kozlova, Svetlana A.,
Di-hydroxybenzenes: Catechol, resorcinol, and hydroquinone,
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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,
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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
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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,
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Bender, Bieling, et al., 1983
Bender, R.; Bieling, V.; Maurer, G.,
The vapour pressures of solids: anthracene, hydroquinone, and resorcinol,
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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,
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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,
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Oikawa, Abe, et al., 1985
Oikawa, A.; Abe, H.; Mikami, N.; Ito, M.,
Electronic spectra and ionization potentials of rotational isomers of severaldDisubstituted benzenes,
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Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [all data]
Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V.,
Photoionization and ion-molecule reactions in quinones and alcohols,
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Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes,
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Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
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Radecki and Grzybowski, 1978
Radecki, A.; Grzybowski, J.,
Linear relationship between retention indices and chemical structure of phenols,
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Grzybowski, Lamparczyk, et al., 1980
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Relationship between the retention indices of phenols on polar and non-polar stationary phases,
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Isolation and identification of volatile flavor compounds in nonfermented coarse-cut sausage. Flavor as a quality factor of nonfermented sausage. 1,
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Xian, Q.-M.; Chen, H.-D.; Zou, H.-H.,
Allelopathic activity of volatile substance from submerged macrophytes on Microcystin aeruginosa,
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Peterson, 1992
Peterson, K.L.,
Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols,
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Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
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Analysis of aromatic hydrocarbons in pyrolytic oil derived from biomass,
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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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