1,4-Benzenedicarboxylic acid, dimethyl ester
- Formula: C10H10O4
- Molecular weight: 194.1840
- IUPAC Standard InChIKey: WOZVHXUHUFLZGK-UHFFFAOYSA-N
- CAS Registry Number: 120-61-6
- 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: Terephthalic acid, dimethyl ester; Dimethyl p-phthalate; Dimethyl terephthalate; Dimethyl 1,4-benzenedicarboxylate; Methyl 4-(carbomethoxy)benzoate; Dimethyl p-benzenedicarboxylate; Dimethylester kyseliny isoftalove; DMT; NCI-C50055; Dimethylester kyseliny tereftalove; Dimethyl ester of 1,4-benzenedicarboxylic acid; Terephthalate, dimethyl; 1,4-Benzenedicarboxylic acid, 1,4-dimethyl ester; Methyl p-(methoxycarbonyl)benzoate; NSC 3503; Dimethyl terphthalate
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -169.7 | kcal/mol | Ccb | Karyakin, Rabinovich, et al., 1978 | ALS |
ΔfH°solid | -175.10 ± 0.24 | kcal/mol | Ccb | Colomina, Laynez, et al., 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1106.99 ± 0.21 | kcal/mol | Ccb | Colomina, Laynez, et al., 1972 | Corresponding ΔfHºsolid = -175.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.40 | 298.15 | Elliott and Chris, 1968 | T = 30 to 200°C.; DH |
65.99 | 353. | Smith and Dole, 1956 | T = 80 to 190°C. Equation only.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 415.2 | K | N/A | Dozen, Fujishima, et al., 1978 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 413.80 | K | N/A | Elliott and Chris, 1968, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Tfus | 413.8 | K | N/A | Smith and Dole, 1956, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 413. | K | N/A | Shirley and Reedy, 1951 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 413. | K | N/A | Hennion and Kurtz, 1943 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 25.00 ± 0.07 | kcal/mol | C | Roux, Jimenez, et al., 1998 | ALS |
ΔsubH° | 25.00 ± 0.07 | kcal/mol | N/A | Victoria Roux, Jime´nez, et al., 1998 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15. | 428. | A | Stephenson and Malanowski, 1987 | Based on data from 413. to 523. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.81 ± 0.07 | 321. | ME | Victoria Roux, Jime´nez, et al., 1998 | Based on data from 311. to 330. K.; AC |
22.6 | 388. | N/A | Stephenson and Malanowski, 1987 | Based on data from 373. to 413. K.; AC |
21.1 | 393. | GS | Kraus, Beranek, et al., 1962 | Based on data from 373. to 413. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.6482 | 415.4 | Karyakin and Shvetsova, 1982 | DH |
7.5600 | 413.79 | Elliott and Chris, 1968 | DH |
7.6721 | 413.8 | Smith and Dole, 1956 | DH |
7.670 | 413.8 | Acree, 1993 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
18.4 | 415.4 | Karyakin and Shvetsova, 1982 | DH |
18.27 | 413.79 | Elliott and Chris, 1968 | DH |
18.5 | 413.8 | Smith and Dole, 1956 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 201.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 194.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.824 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K)=-20.2 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
0.824 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
0.640011 | ECD | Kuhn, Levins, et al., 1968 | Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.78 ± 0.03 | EI | Kuhn, Levins, et al., 1968 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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-6813 |
NIST MS number | 228185 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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 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 | Ultra-1 | 125. | 1461. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 150. | 1470. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 175. | 1480. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 200. | 1492. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Packed | OV-1 | 150. | 1468. | Fedoreev and Maksimov, 1977 | Gaschrom; Column length: 1.5 m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1475. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1469. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-ALLOY-5 | 1512. | Tsuge, Ohtan, et al., 2011 | 30. m/0.25 mm/0.25 μm, 40. C @ 2. min, 20. K/min, 320. C @ 13. min |
Capillary | Ultra-1 | 1468. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 1473. | Zenkevich, 2003 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1475. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Other | Methyl Silicone | 1475. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Sokolov, L.B.,
Thermodynamics of the synthesis of isomeric poly(phenylenephthalamides),
Vysokomol. Soedin. Ser. B, 1978, 20, 662-666. [all data]
Colomina, Laynez, et al., 1972
Colomina, M.; Laynez, J.L.; Perez-Ossorio, R.; Turrion, C.,
Enthalpies of combustion and formation of six methyl esters of benzene carboxylic acids,
J. Chem. Thermodyn., 1972, 4, 499-506. [all data]
Elliott and Chris, 1968
Elliott, J.H.; Chris, M.D.,
Some thermodynamic properties of high purity dimethyl terephthalate,
J. Chem. Eng. Data, 1968, 13, 475-479. [all data]
Smith and Dole, 1956
Smith, C.W.; Dole, M.,
Specific heat of synthetic high polymers. VII. Polyethylene terephthalate,
J. Polym. Sci., 1956, 20, 37-56. [all data]
Dozen, Fujishima, et al., 1978
Dozen, Y.; Fujishima, S.; Shingu, H.,
Structures and fusion parameters of methoxycarbonyl-benzenes and -naphthalenes,
Thermochim. Acta, 1978, 25, 2, 209, https://doi.org/10.1016/0040-6031(78)85008-4
. [all data]
Elliott and Chris, 1968, 2
Elliott, J.H.; Chris, M.D.,
Some thermodynamic properties of high purity dimethyl terephthalate,
J. Chem. Eng. Data, 1968, 13, 475. [all data]
Smith and Dole, 1956, 2
Smith, C.W.; Dole, M.,
Specific heat of synthetic high polymers VII. Polyethylene terephthalate,
J. Polym. Sci., 1956, 20, 37. [all data]
Shirley and Reedy, 1951
Shirley, D.A.; Reedy,
Alkylation with Long Chain p-Toluenesulfonates. III. Reaction of n-Octadecyl p-Toluenesulfonate with p-Tolylmagensium Bromide,
J. Am. Chem. Soc., 1951, 73, 4886. [all data]
Hennion and Kurtz, 1943
Hennion, G.F.; Kurtz, R.A.,
Some Friedel-Crafts Type ALkylations with Boron Trifluoride,
J. Am. Chem. Soc., 1943, 65, 1001. [all data]
Roux, Jimenez, et al., 1998
Roux, M.A.; Jimenez, P.; Davalos, J.Z.; Turrion, C.; Afeefy, H.Y.; Liebman, J.F.,
Enthalpies of formation of methyl benzenecarboxylates,
J. Chem. Soc. Faraday Trans., 1998, 94, 887-890. [all data]
Victoria Roux, Jime´nez, et al., 1998
Victoria Roux, María; Jime´nez, Pilar; Dávalos, Juan Z.; Turrión, Concepción; Afeefy, Hussein Y.; Liebman, Joel F.,
Enthalpies of formation of methyl benzenecarboxylates,
Faraday Trans., 1998, 94, 7, 887-890, https://doi.org/10.1039/a800401c
. [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]
Kraus, Beranek, et al., 1962
Kraus, M.; Beranek, L.; Kochloeff, K.; Bazant, V.,
Chem. Prum., 1962, 12, 649. [all data]
Karyakin and Shvetsova, 1982
Karyakin, N.V.; Shvetsova, K.G.,
Thermodynamics of reactions of 1,4-butanediol with terephthalic acid and its derivatives,
Deposited Doc. SPSTL 861 Khp-D82, 1982, 14pp. [all data]
Acree, 1993
Acree, William E.,
Thermodynamic properties of organic compounds,
Thermochimica Acta, 1993, 219, 97-104, https://doi.org/10.1016/0040-6031(93)80486-T
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y.,
Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions,
Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [all data]
Kuhn, Levins, et al., 1968
Kuhn, W.F.; Levins, R.J.; Lilly, A.C., Jr.,
Electron affinities and ionization potentials of phthalate compounds,
J. Chem. Phys., 1968, 49, 5550. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]
Herrmann, Dufka, et al., 1986
Herrmann, F.; Dufka, O.; Churacek, J.,
Fused-Silica Capillary Gas Chromatography-Mass Spectrometry of Some Dicarboxylic Acids Present in Condensation-Type Polymers I. Dimethyl Esters,
J. Chromatogr., 1986, 360, 79-88, https://doi.org/10.1016/S0021-9673(00)91653-4
. [all data]
Fedoreev and Maksimov, 1977
Fedoreev, S.A.; Maksimov, O.B.,
The study of the composition of aromatic esters by gas-liquid chromatography,
Solid Fuel Chem. (Engl. Transl.), 1977, 17-22. [all data]
Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses,
J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Tsuge, Ohtan, et al., 2011
Tsuge, S.; Ohtan, H.; Watanabe, C.,
Pyrolysis - GC/MS Data Book of Synthetic Polymers, Elsevier, 2011, 420. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Zenkevich, 2003
Zenkevich, I.G.,
Criteria for Evaluation of Elution Order of Isomeric Organic Compounds,
Zh. Phys. Khim. (Rus.), 2003, 77, 1, 92-98. [all data]
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]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid EA Electron affinity Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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