Phenol, 2,4-dichloro-
- Formula: C6H4Cl2O
- Molecular weight: 163.001
- IUPAC Standard InChIKey: HFZWRUODUSTPEG-UHFFFAOYSA-N
- CAS Registry Number: 120-83-2
- 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: DCP; 2,4-Dichlorophenol; 4,6-Dichlorophenol; NCI-C55345; 1-Hydroxy-2,4-dichlorobenzene; 2,4-DCP; Rcra waste number U081; 1,3-Dichloro-4-hydroxybenzene; NSC 2879
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Phase change data
Go To: Top, 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
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 | 483.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 318.0 | K | N/A | Poeti, Faneli, et al., 1982 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 323. | K | N/A | Vorob'ev, Borisov, et al., 1981 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 318. | K | N/A | van de Lande, 1932 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.1 ± 0.1 | kcal/mol | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 317. to 344. K.; AC |
ΔvapH° | 13.9 ± 0.07 | kcal/mol | N/A | Mokbel, Pauchon, et al., 1995 | Based on data from 323. to 443. K. See also Verevkin, Emel'yanenko, et al., 2007.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 18.6 ± 0.07 | kcal/mol | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 278. to 315. K.; AC |
ΔsubH° | 16.8 ± 0.26 | kcal/mol | C | Ribeiro Da Silva, Ferrao, et al., 1994 | HCl (1:600 H2O); ALS |
ΔsubH° | 16.8 ± 0.26 | kcal/mol | C | da Silva, 1994 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.5 | 331. | GS | Verevkin, Emel'yanenko, et al., 2007 | Based on data from 317. to 344. K.; AC |
12.5 | 383. | N/A | Mokbel, Pauchon, et al., 1995 | Based on data from 323. to 443. K. See also Verevkin, Emel'yanenko, et al., 2007.; AC |
14.5 | 341. | A | Stephenson and Malanowski, 1987 | Based on data from 326. to 483. K. See also Stull, 1947 and Arro, Melder, et al., 1975.; AC |
8.7906 | 491. | N/A | Vorob'ev, Borisov, et al., 1981 | DH |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.9 | 491. | Vorob'ev, Borisov, et al., 1981 | 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 |
---|---|---|---|---|---|
326. to 483. | 5.26153 | 2330.829 | -39.935 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.8016 | 318.0 | Poeti, Fanelli, et al., 1982 | DH |
4.802 | 318. | Domalski and Hearing, 1996 | AC |
6.7902 | 323. | Vorob'ev, Borisov, et al., 1981 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.10 | 318.0 | Poeti, Fanelli, et al., 1982 | DH |
21.0 | 323. | Vorob'ev, Borisov, et al., 1981 | DH |
Gas Chromatography
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 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 |
---|---|---|---|---|---|
Capillary | SE-30 | 160. | 1170. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Capillary | SE-30 | 180. | 1165. | Shakirov, Tsypysheva, et al., 1988 | Column length: 20. m; Column diameter: 0.2 mm |
Capillary | SE-30 | 140. | 1160. | Korhonen, 1984 | |
Capillary | SE-30 | 160. | 1170. | Korhonen, 1984 | |
Capillary | SE-30 | 180. | 1181. | Korhonen, 1984 | |
Packed | Methyl Silicone | 150. | 1170. | Radecki, Grzybowski, et al., 1979 |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1183. | Grzybowski, Lamparczyk, et al., 1980 | Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | FFAP | 160. | 2151. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.35 mm |
Capillary | FFAP | 160. | 2151. | Korhonen, 1984 | |
Capillary | FFAP | 180. | 2131. | Korhonen, 1984 | |
Capillary | FFAP | 200. | 2145. | Korhonen, 1984 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1144.8 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | DB-1 | 1151. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 50. C @ 0. min, 10. K/min |
Capillary | DB-1 | 1148. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 50. C @ 0. min, 5. K/min |
Capillary | DB-5 | 1169. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-54 | 1156. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-54 | 1164. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-30 | 1168. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | SE-30 | 1147. | Korhonen, 1984 | 2. K/min; Tstart: 100. C |
Capillary | SE-30 | 1158. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1187.7 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Capillary | 5 % Phenyl methyl siloxane | 1164. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 2192.93 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 10. K/min; Tstart: 100. C |
Capillary | DB-Wax | 2184.21 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 5. K/min; Tstart: 100. C |
Capillary | DB-Wax | 2192.08 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 10. K/min; Tstart: 50. C |
Capillary | DB-Wax | 2182.99 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 5. K/min; Tstart: 50. C |
Capillary | FFAP | 2120. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | FFAP | 2096. | Korhonen, 1984 | 2. K/min; Tstart: 100. C |
Capillary | FFAP | 2104. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 1165. | Zenkevich, Moeder, et al., 2004 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 3. min, 3. K/min, 280. C @ 20. min |
Capillary | Ultra-1 | 1138. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Capillary | SE-30 | 1143. | Ibrahim and Suffet, 1988 | N2, 50. C @ 8. min, 5. K/min, 275. C @ 10. min; Column length: 60. m; Column diameter: 0.32 mm |
Capillary | SE-54 | 1163. | Harland, Cumming, et al., 1986 | He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane with 5 % Ph groups | 1188. | Robinson, Adams, et al., 2012 | Program: not specified |
Capillary | Polydimethyl siloxane with 5 % Ph groups | 1193. | Robinson, Adams, et al., 2012 | Program: not specified |
Capillary | Methyl Silicone | 1160. | Yu and Zazhi, 2005 | Program: not specified |
Capillary | PTE-5 | 1189. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | Ultra-2 | 1189. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | SE-30 | 1183. | Peterson, 1992 | Program: not specified |
Capillary | SE-30 | 1144. | Ibrahim and Suffet, 1988 | N2; Column length: 60. m; Column diameter: 0.32 mm; Program: 50C(8min) => 3C/min => 150C => 35C/min => 275C (10min) |
Capillary | OV-1 | 1140. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1140. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Superox 0.6; Carbowax 20M | 2098. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 2098. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 196.3 | Donnelly, Abdel-Hamid, et al., 1993 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min |
Capillary | DB-5 | 196.53 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Phase change data, Gas Chromatography, 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]
Poeti, Faneli, et al., 1982
Poeti, G.; Faneli, E.; Braghetti, M.J.,
A differential scanning calorimetric study of some phenol derivatives,
Therm. Anal., 1982, 24, 2, 273, https://doi.org/10.1007/BF01913681
. [all data]
Vorob'ev, Borisov, et al., 1981
Vorob'ev, G.I.; Borisov, N.N.; Novikova, G.A.; Efimova, V.L.,
Physicochemical properties of 2,4-dichloro-1-(4-nitrophenoxy)benzene,
Khim. Prom. (Moscow), 1981, (12), 728. [all data]
van de Lande, 1932
van de Lande, L.M.F.,
The Action of Sodium Methylate on SOme Derivatives of m-Dichlorobenzene,
Recl. Trav. Chim. Pays-Bas, 1932, 51, 98-113. [all data]
Verevkin, Emel'yanenko, et al., 2007
Verevkin, Sergey P.; Emel'yanenko, Vladimir N.; Klamt, Andreas,
Thermochemistry of Chlorobenzenes and Chlorophenols: Ambient Temperature Vapor Pressures and Enthalpies of Phase Transitions,
J. Chem. Eng. Data, 2007, 52, 2, 499-510, https://doi.org/10.1021/je060429r
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Mokbel, Pauchon, et al., 1995
Mokbel, I.; Pauchon, V.; Jose, J.,
Vapor pressures and sublimation pressures of 2,4-dichlorophenol, 2,6-dichlorophenol, and 2,4,6-trichlorophenol,
ELDATA: Int. Electron. J. Phys. Chem. Data, 1995, 1, 1, 53. [all data]
Ribeiro Da Silva, Ferrao, et al., 1994
Ribeiro Da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Jiye, F.,
Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry,
J. Chem. Thermodyn., 1994, 26, 839-846. [all data]
da Silva, 1994
da Silva, M.,
Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry,
The Journal of Chemical Thermodynamics, 1994, 26, 8, 839-846, https://doi.org/10.1006/jcht.1994.1100
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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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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
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Arro, Melder, et al., 1975
Arro, J.; Melder, L.; Tamvelius, H.,
Trudy Tallinskogo Politekhnicheskogo Instit., 1975, 390, 37. [all data]
Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M.,
A differential scanning calorimetric study of some phenol derivatives,
J. Therm. Anal., 1982, 24(2), 273-279. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
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Evans and Haken, 1989
Evans, M.B.; Haken, J.K.,
Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds,
J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5
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Shakirov, Tsypysheva, et al., 1988
Shakirov, L.G.; Tsypysheva, L.G.; Suleimamova, R.A.; Naimushin, A.I.; Tsypyshev, O.Yu.,
Gas chromatographic determination of the products of the synthesis of chlorine-substituted salicylic acids,
Zh. Anal. Khim., 1988, 43, 143-146. [all data]
Korhonen, 1984
Korhonen, I.O.O.,
Gas-liquid chromatographic analyses. XXXI. Retention increments of isomeric chlorophenols on low-polarity (SE-30) and polar (FFAP) capillary columns,
J. Chromatogr., 1984, 315, 185-200, https://doi.org/10.1016/S0021-9673(01)90736-8
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Radecki, Grzybowski, et al., 1979
Radecki, A.; Grzybowski, J.; Lamparczyk, H.; Nasal, A.,
Relationships between retention indices and substituent constants of phenols on polar stationary phases,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1979, 2, 9, 581-582, https://doi.org/10.1002/jhrc.1240020911
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Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A.,
Relationship between the retention indices of phenols on polar and non-polar stationary phases,
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Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P.,
Use of incremental models to estimate the retention indexes of aromatic compounds,
Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946
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Gerbino and Castello, 1995
Gerbino, T.C.; Castello, G.,
Prediction of programmed temperature retention indices on capillary columns of different polarities,
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Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
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Weber, 1986
Weber, L.,
Utilization of the Sadtler standard RI system in micropollution analyses,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 446-451, https://doi.org/10.1002/jhrc.1240090806
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Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
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Zenkevich, Moeder, et al., 2004
Zenkevich, I.G.; Moeder, M.; Koeller, G.; Schrader, S.,
Using new structurally related additive schemes in the precalculation of gas chromatographic retention indices of polychlorinated hydroxybiphenyls on HP-5 stationary phase,
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Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
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Ibrahim and Suffet, 1988
Ibrahim, E.A.; Suffet, I.H.,
Freon FC-113, an Alternative to Methylene Chloride for Liquid-Liquid Extraction of Trace Organics from Chlorinated Drinking Water,
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Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E.,
The Kovats indexes of some organic micropollutants on an SE54 capillary column,
EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]
Robinson, Adams, et al., 2012
Robinson, A.L.; Adams, D.O.; Boss, P.K.; Heymann, H.; Solomon, P.S.; Trengove, R.D.,
Influence of geographic origine on the sensory characteristics and wine composition of Vitus viniferas cv. Cabernet Sauvignon wines from Australia (Supplemental data),
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Yu and Zazhi, 2005
Yu, H.; Zazhi, J.,
Relationship between chromatogram retention index and toxicity of chlorinated phenols and chlorinated benzenes to Guppy,
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Nakano, Fujimori, et al., 1992
Nakano, T.; Fujimori, K.; Takaishi, Y.; Okuno, T.,
GC/MS-SIM analysis of polychlorobenzenes, polychlorophenols and polychloronaphthalenes,
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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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Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F.,
Application of gas chromatographic retention properties to the identification of environmental contaminants,
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Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions 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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