2-Propenoic acid, ethyl ester
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChI: InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3
- IUPAC Standard InChIKey: JIGUQPWFLRLWPJ-UHFFFAOYSA-N
- CAS Registry Number: 140-88-5
- 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: Acrylic acid ethyl ester; Ethyl acrylate; Ethyl propenoate; Ethyl 2-propenoate; CH2=CHCOOC2H5; Acrylate d'ethyle; Acrylic acid, ethyl ester (inhibited); Ethyl acrylate, inhibited; Ethylacrylaat; Ethylakrylat; Etil acrilato; Etilacrilatului; NCI-C50384; Acrylsaeureaethylester; Aethylacrylat; Akrylanem etylu; Carboset 511; Ethoxycarbonylethylene; Ethylester kyseliny akrylove; Rcra waste number U113; Ethyl ester of 2-propenoic acid; NSC 8263
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -79.21 | kcal/mol | N/A | Vilcu and Perisanu, 1980 | Value computed using ΔfHliquid° value of -370.6 kj/mol from Vilcu and Perisanu, 1980 and ΔvapH° value of 39.2 kj/mol from Vilcu, Perisanu, et al., 1975.; DRB |
| ΔfH°gas | -84.66 | kcal/mol | Ccb | Vilcu, Perisanu, et al., 1975 | ALS |
| ΔfH°gas | -78.35 | kcal/mol | N/A | Baroody and Carpenter, 1972 | Value computed using ΔfHliquid° value of -367.0 kj/mol from Baroody and Carpenter, 1972 and ΔvapH° value of 39.2 kj/mol from Vilcu, Perisanu, et al., 1975.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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°liquid | -88.58 | kcal/mol | Chyd | Vilcu and Perisanu, 1980 | |
| ΔfH°liquid | -94.03 | kcal/mol | Ccb | Vilcu, Perisanu, et al., 1975 | |
| ΔfH°liquid | -87.8 | kcal/mol | Ccb | Baroody and Carpenter, 1972 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -648.91 | kcal/mol | Ccb | Vilcu, Perisanu, et al., 1975 | Corresponding ΔfHºliquid = -94.61 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 373.0 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 373. | K | N/A | American Tokyo Kasei, 1988 | BS |
| Tboil | 372.5 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 9.37 | kcal/mol | V | Vilcu, Perisanu, et al., 1975 | ALS |
| ΔvapH° | 9.37 | kcal/mol | N/A | Vilcu, Perisanu, et al., 1975 | DRB |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.89 | 258. | Stull, 1947 | Based on data from 243. to 372. 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 |
|---|---|---|---|---|---|
| 243.7 to 372.7 | 4.26882 | 1366.06 | -52.678 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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
+
=
By formula: H2 + C5H8O2 = C5H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -32.5 ± 1.1 | kcal/mol | Chyd | Vilcu and Perisanu, 1980 | 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, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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 |
|---|---|---|
| ≤10.3 | PE | Morizur, Mercier, et al., 1982 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References, Notes
Data compiled by: Coblentz Society, Inc.
- GAS (30 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
- SOLUTION (5% IN CCl4 FOR 3800-1300, 5% IN CS2 FOR 1300-600, AND 5% IN CCl4 FOR 600-240 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty
- gas; IFS66V (Bruker); 3-Term B-H Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm-1 resolution - gas; IFS66V (Bruker); Boxcar Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm-1 resolution - gas; IFS66V (Bruker); Happ Genzel Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm-1 resolution - gas; IFS66V (Bruker); NB Strong Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm-1 resolution - gas; IFS66V (Bruker); Triangular Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm-1 resolution
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, NIST Free Links, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| 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 | NIST Mass Spectrometry Data Center, 1998. |
| NIST MS number | 290903 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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 | OV-101 | 100. | 676. | Horna, Táborský, et al., 1985 | N2; Column length: 19. m; Column diameter: 0.28 mm |
| Capillary | OV-101 | 120. | 678. | Horna, Táborský, et al., 1985, 2 | N2; Column length: 19. m; Column diameter: 0.28 mm |
| Capillary | OV-101 | 80. | 681. | Horna, Táborský, et al., 1985, 2 | N2; Column length: 19. m; Column diameter: 0.28 mm |
| Packed | SE-30 | 150. | 680. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
| Packed | SE-30 | 100. | 676. | Winskowski, 1983 | Gaschrom Q; Column length: 2. m |
| Packed | Apiezon L | 120. | 644. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
| Packed | Apiezon L | 160. | 648. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
| Packed | SE-30 | 150. | 684. | Ashes and Haken, 1975 | He, Celatom silanized (62-72 mesh); Column length: 3.7 m |
| Packed | SE-30 | 150. | 664. | Allen and Haken, 1970 | Celite 560 silanized; Column length: 3.7 m |
| Packed | SE-30 | 150. | 664. | Germaine and Haken, 1969 | Celite 560; Column length: 3.7 m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SP-1000 | 100. | 992. | Horna, Táborský, et al., 1985 | N2; Column length: 46. m; Column diameter: 0.23 mm |
| Capillary | SP-1000 | 120. | 993. | Horna, Táborský, et al., 1985, 2 | N2; Column length: 46. m; Column diameter: 0.23 mm |
| Capillary | SP-1000 | 80. | 989. | Horna, Táborský, et al., 1985, 2 | N2; Column length: 46. m; Column diameter: 0.23 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 678. | Wu, Kuo, et al., 1991 | 50. m/0.32 mm/1.05 μm, He, 2. K/min, 260. C @ 40. min; Tstart: 40. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 683. | 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, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | DC-400 | 150. | 648. | Anderson, 1968 | Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 702. | de Souza, Vásquez, et al., 2006 | He, 35. C @ 3. min, 6. K/min; Column length: 13.5 m; Column diameter: 0.32 mm; Tend: 225. C |
| Capillary | OV-101 | 681. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 681. | Vinogradov, 2004 | Program: not specified |
| Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 664. | 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. | 677. | 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 | Carbowax 20M | 980. | Vinogradov, 2004 | Program: not specified |
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, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vilcu and Perisanu, 1980
Vilcu, R.; Perisanu, S.,
The ideal gas state enthalpies of formation of some monomers,
Rev. Roum. Chim., 1980, 25, 619-624. [all data]
Vilcu, Perisanu, et al., 1975
Vilcu, R.; Perisanu, S.; Ciocazanu, I.,
Heats of formation in the ideal gas state of some substances containing carbon, hydrogen and oxygen,
Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 105-112. [all data]
Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A.,
Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [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]
American Tokyo Kasei, 1988
American Tokyo Kasei,
TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [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]
Morizur, Mercier, et al., 1982
Morizur, J.-P.; Mercier, J.; Sarraf, M.,
2-Substituted-2,3-dihydro-4H-pyrans: Competition between 'Retro Diels-Alder' fragmentation and substituent loss,
Org. Mass Spectrom., 1982, 17, 327. [all data]
Horna, Táborský, et al., 1985
Horna, A.; Táborský, J.; Churácek, J.; Dufka, O.,
Chromatography of monomers. IV. Gas-liquid chromatographic studies of C1-C6 n-alkyl and C3-C6 isoalkyl acrylates and their hydrogen halide and halogen addition derivatives,
J. Chromatogr., 1985, 348, 141-149, https://doi.org/10.1016/S0021-9673(01)92447-1
. [all data]
Horna, Táborský, et al., 1985, 2
Horna, A.; Táborský, J.; Dufka, O.; Matousek, P.; Churácek, J.,
Chromatography of monomers. II. Glass capillary gas chromatography of C1-C18 alkyl esters of acrylic and methacrylic acids,
J. Chromatogr., 1985, 325, 367-378, https://doi.org/10.1016/S0021-9673(00)96047-3
. [all data]
Tiess, 1984
Tiess, D.,
Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30,
Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]
Winskowski, 1983
Winskowski, J.,
Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren,
Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041
. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Ashes and Haken, 1975
Ashes, J.R.; Haken, J.K.,
Gas chromatography of homologous esters. IX. Structure-retention increments of unsaturated esters,
J. Chromatogr., 1975, 111, 1, 171-187, https://doi.org/10.1016/S0021-9673(01)80159-X
. [all data]
Allen and Haken, 1970
Allen, I.D.; Haken, J.K.,
Gas chromatography of homologous esters. Part IV. Influence of stationary phase polarity on retention of unsaturated esters,
J. Chromatogr., 1970, 51, 415-422, https://doi.org/10.1016/S0021-9673(01)96890-6
. [all data]
Germaine and Haken, 1969
Germaine, R.W.; Haken, J.K.,
Gas chromatography of homologous esters. Part 2. Unsaturated esters,
J. Chromatogr., 1969, 43, 43-47, https://doi.org/10.1016/S0021-9673(00)99163-5
. [all data]
Wu, Kuo, et al., 1991
Wu, P.; Kuo, M.-C.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T.,
Free and glycosidically bound aroma compounds in pineapple (Ananas comosus L. Merr.),
J. Agric. Food Chem., 1991, 39, 1, 170-172, https://doi.org/10.1021/jf00001a033
. [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]
Anderson, 1968
Anderson, D.G.,
USe of Kovats retention indices and response factors for the qualitative and quantitative analysis of coating solvents,
J. Paint Technol., 1968, 40, 527, 549-557. [all data]
de Souza, Vásquez, et al., 2006
de Souza, M.D.C.A.; Vásquez, P.; del Mastro, N.L.; Acree, T.E.; Lavin, E.H.,
Characterization and cachaca and rum aroma,
J. Agric. Food Chem., 2006, 54, 2, 485-488, https://doi.org/10.1021/jf0511190
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [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]
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, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - 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.