Butanedioic acid, methylene-, dimethyl ester
- Formula: C7H10O4
- Molecular weight: 158.1519
- IUPAC Standard InChI: InChI=1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
- IUPAC Standard InChIKey: ZWWQRMFIZFPUAA-UHFFFAOYSA-N
- CAS Registry Number: 617-52-7
- 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: Succinic acid, methylene-, dimethyl ester; Dimethyl itaconate; Itaconic acid, dimethyl ester; Methylenesuccinic acid, dimethyl ester; Dimethyl methylenesuccinate; Butanedioic acid, 2-methylene-, dimethyl ester; Dimethyl 2-methylenesuccinate
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 481.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 381.2 | 0.015 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 67.0 | 357. | A | Stephenson and Malanowski, 1987 | Based on data from 342. to 481. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 342.5 to 481. | 6.41284 | 2871.257 | -33.212 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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 compiled by: John E. Bartmess
De-protonation reactions
C7H9O4- + =
By formula: C7H9O4- + H+ = C7H10O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 1458. ± 17. | kJ/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Acid: CH2=C(CO2Me)CH2CO2Me. Between MeSH, tBuSH. |
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 |
|---|---|---|---|---|---|
| Capillary | Ultra-1 | 100. | 1061. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 125. | 1059. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 150. | 1057. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 75. | 1065. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1096.5 | Tret'yakov, 2008 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
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.
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]
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]
Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R.,
Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions,
J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045
. [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]
Tret'yakov, 2008
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2008. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔrG° Free energy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.