Butylated Hydroxytoluene
- Formula: C15H24O
- Molecular weight: 220.3505
- IUPAC Standard InChI: InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
- IUPAC Standard InChIKey: NLZUEZXRPGMBCV-UHFFFAOYSA-N
- CAS Registry Number: 128-37-0
- 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: Phenol, 2,6-bis(1,1-dimethylethyl)-4-methyl-; p-Cresol, 2,6-di-tert-butyl-; Advastab 401; Antioxidant DBPC; Antioxidant KB; Antioxidant 29; Antioxidant 30; Antioxidant 4K; AO 29; AO 4K; Butylhydroxytoluene; BHT; BUKS; Catalin Antioxydant 1; Catalin CAO-3; Chemanox 11; CAO 1; CAO 3; Dalpac; Deenax; Di-tert-butyl-p-cresol; Di-tert-butyl-p-methylphenol; Di-tert-butylcresol; Dibunol; Dibutylated hydroxytoluene; DBPC; Impruvol; Ionol; Ionol (Antioxidant); Ionol CP; Ionol 1; Ionole; Nonox TBC; P 21; Parabar 441; Stavox; Sumilizer BHT; Sustane BHT; Tenamene 3; Tenox BHT; Topanol; Topanol O; Topanol OC; Vanlube PC; Vanlube PCX; Vianol; 2,6-Bis(1,1-dimethylethyl)-4-methylphenol; 2,6-Di-tert-butyl-p-cresol; 2,6-Di-tert-butyl-p-methylphenol; 2,6-Di-tert-butyl-4-methylphenol; 3,5-Di-tert-butyl-4-hydroxytoluene; 4-Hydroxy-3,5-di-tert-butyltoluene; 4-Methyl-2,6-di-tert-butylphenol; 2,6-Di-t-butyl-4-methylphenol; 2,6-Di-tert-butyl-1-hydroxy-4-methyl benzene; 2,6-di-Butyl-para-cresol; 2,6-di-tert-Butyl-methylphenol; o-Di-tert-butyl-p-methylphenol; Bht(food grade); Butylated hydroxytoluol; Dbpc(technical grade); DBMP; NCI-C03598; Paranox 441; 1-Hydroxy-4-methyl-2,6-di-tert-butylbenzene; 2,6-Di-terc.butyl-p-kresol; 2,6-Di-tert-butyl-4-cresol; 4-Methyl-2,6-di-terc. butylfenol; 4-Methyl-2,6-tert-butylphenol; Di-tert-Butylparamethylphenol; Di-tert-Butyl-4-methylphenol; 2,6-Di-t-butyl-p-cresol; Phenol, 2,6-di-tert-butyl-4-methyl-; 4-Methyl-2,6-di-t-butyl-phenol; Annulex BHT; Antrancine 8; Lowinox BHT; Nipanox BHT; Ralox BHT; Sustane; Vulkanox KB; BHT (butylated hydroxytoluene); 2,6-di-ter-butyl-4-methyl-phenol; 2,6-Di-tert-butyl-para-methylphenol; 2,6-di-tert-butyl-p-cresol (BHT); Butylated hydroxyl toluene (BHT); Dibutylhydroxytoluene; Dibutylcresol; 2,6-Bis(tert-butyl)-4-methylphenol; 2,6-Di(tert-butyl)hydroxytoluene; Ionol BHT; BHT Swanox; Agidol; 2,6-di-ter-butul-4-methyl-phenol; 4-Methyl-2,6-di-tert.-butylphenol; Di-ter-butyl p-cresol; butylated OH tolueno; Dibutyl-p-cresol; Ergotamine, dihydro-, monomethanesulfonate (salt); Hydagen DEO (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -296.9 | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -410. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -8916. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -418. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
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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.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 538.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 344. | K | N/A | Inozemtsev, Liakumovich, et al., 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Tfus | 342.86 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.25 K; TRC |
| Tfus | 343. | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.15 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 91.9 ± 3.2 | kJ/mol | C | da Silva, Matos, et al., 2001 | AC |
| ΔsubH° | 88.0 ± 0.8 | kJ/mol | GS | Verevkin, 1999 | Based on data from 298. to 338. K.; AC |
| ΔsubH° | 117.3 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
| ΔsubH° | 113.1 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 87.8 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 343. K.; AC |
| 61.5 | 373. | A | Stephenson and Malanowski, 1987 | Based on data from 358. to 536. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 359.0 to 535.7 | 5.05062 | 2451.662 | -49.846 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 86.8 ± 0.8 | 319. | GS | Verevkin, 1999 | Based on data from 298. to 338. K.; AC |
| 87.8 | 318. | GS | Stephenson and Malanowski, 1987 | Based on data from 303. to 343. K. See also Fel'dshtein and Kuz'minskii, 1971.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 19.85 | 341.7 | DSC | Verevkin, 1999 | AC |
| 23.85 | 343.7 | DTA | Inozemtsev, Liakumovich, et al., 1972 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= 2
By formula: C7H8O + C15H24O = 2C11H16O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.7 ± 1.8 | kJ/mol | Eqk | Nesterova, Verevkin, et al., 1985 | liquid phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.80 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (1 mg / 300 mg KBr DISC) $$ PURITY - ANALYTICAL; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLID (1.12% IN KBr DISC); PERKIN-ELMER (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1340, 10% IN CS2 FOR 1340-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F.,
No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols,
Bull. Soc. Chim. France, 1971, 3180-3187. [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]
Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D.,
Russ. J. Phys. Chem., 1972, 46, 6, 914. [all data]
Witschonke, 1954
Witschonke, C.R.,
Freezing point and purity data for some organic compounds,
Anal. Chem., 1954, 26, 562-4. [all data]
da Silva, Matos, et al., 2001
da Silva, Manuel A.V. Ribeiro; Matos, M. Agostinha R.; Miranda, Margarida S.; Sousa, M. Helena F.A.; dos Santos, Rui M. Borges; Bizarro, Magda M.; Simões, José A. Martinho,
Structural Chemistry, 2001, 12, 2, 171-181, https://doi.org/10.1023/A:1016600727116
. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemistry of phenols: buttress effects in sterically hindered phenols,
The Journal of Chemical Thermodynamics, 1999, 31, 11, 1397-1416, https://doi.org/10.1006/jcht.1999.0466
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Fel'dshtein and Kuz'minskii, 1971
Fel'dshtein, L.S.; Kuz'minskii, A.S.,
Kauch. Rezina, 1971, 30, 11, 15. [all data]
Nesterova, Verevkin, et al., 1985
Nesterova, T.N.; Verevkin, S.P.; Malova, T.N.; Pilshchikov, V.A.,
Study of an equilibrium of tert-alkylphenols (thermodynamic analysis of the alkylation of phenols by branched olefins),
Zh. Prikl. Khim. (Leningrad), 1985, 58, 827-833. [all data]
Cetinkaya, Lappert, et al., 1983
Cetinkaya, B.; Lappert, M.F.; Suffolk, R.J.,
Photoelectron spectra of some sterically hindered phenols and related compounds,
J. Chem. Res. Synop., 1983, 316. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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