2-Pyrrolidinone, 1-methyl-
- Formula: C5H9NO
- Molecular weight: 99.1311
- IUPAC Standard InChIKey: SECXISVLQFMRJM-UHFFFAOYSA-N
- CAS Registry Number: 872-50-4
- 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: M-Pyrol; N-Methyl-α-pyrrolidinone; N-Methyl-α-pyrrolidone; N-Methyl-γ-butyrolactam; N-Methyl-2-pyrrolidinone; N-Methyl-2-pyrrolidone; N-Methylpyrrolidinone; N-Methylpyrrolidone; NMP; 1-Methyl-2-Pyrrolidinone; 1-Methyl-2-pyrrolidone; 1-Methyl-5-pyrrolidinone; 1-Methylpyrrolidinone; 2-Pyrrolidone, 1-methyl-; 1-Methylazacyclopentane-2-one; 1-Methylpyrrolidone; N-Methylpyrrolidone-(2); N-Methylpyrrolid-2-one; Methylpyrrolidone; 1-Methylazacyclopentan-2-one; Agsolex 1; N 0131; N-Methyl-gamma-butyrolactam; Micropure ultra; NSC 4594
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -50.39 ± 0.13 | kcal/mol | Ccr | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values |
Condensed phase thermochemistry 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:
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°liquid | -63.51 ± 0.13 | kcal/mol | Ccr | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -714.16 ± 0.11 | kcal/mol | Ccr | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values; ALS |
ΔcH°liquid | -715.0 ± 0.1 | kcal/mol | Ccb | Kozina and Skuratov, 1959 | ALS |
ΔcH°liquid | -715.6 | kcal/mol | Ccb | Skuratov, Kozina, et al., 1958 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
98.57 | 298.15 | Steele, Chirico, et al., 1990 | DH |
73.57 | 298. | Marchidan and Ciopec, 1978 | T = 298 to 461 K.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 475.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 721.7 | K | N/A | Gude and Teja, 1994 | Uncertainty assigned by TRC = 0.5 K; by the flow method; TRC |
Tc | 721.8 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 44.61 | atm | N/A | Gude and Teja, 1994 | Uncertainty assigned by TRC = 0.25 atm; by the flow method; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.22 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.06 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.8 | kcal/mol | EB | Chylinski, Fras, et al., 2004 | Based on data from 352. to 378. K.; AC |
ΔvapH° | 13.12 ± 0.031 | kcal/mol | V | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values; ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
354.7 | 0.013 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.8 | 395. | N/A | Palczewska-Tulinska and Oracz, 2007 | Based on data from 380. to 475. K.; AC |
12.7 | 345. | GS | Linek, Wichterle, et al., 1996 | Based on data from 330. to 373. K.; AC |
12.8 | 350. | EB | Kneisl and Zondlo, 1987 | Based on data from 340. to 476. K.; AC |
11.4 | 425. | EB | Kneisl and Zondlo, 1987 | Based on data from 340. to 476. K.; AC |
11.8 | 376. | A | Stephenson and Malanowski, 1987 | Based on data from 361. to 477. K. See also Dykyj, 1972.; AC |
13.2 | 295. | A | Stephenson and Malanowski, 1987 | Based on data from 291. to 299. K.; AC |
11.8 | 403. | N/A | Bludilina, Baev, et al., 1979 | Based on data from 333. to 473. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.33 | 248.5 | Lisicki and Jamróz, 2000 | AC |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1646. | Nishimura, Yamaguchi, et al., 1989 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1678. | Pozo-Bayon M.A., Ruiz-Rodriguez A., et al., 2007 | 30. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 4. K/min, 250. C @ 15. min |
Capillary | Stabilwax | 1660. | Cros S., Lignot B., et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 240. C @ 10. min |
Capillary | Stabilwax | 1660. | Cros, Lignot, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 240. C @ 10. min |
Capillary | DB-Wax | 1665. | Aubert, Günata, et al., 2003 | 30. m/0.32 mm/0.5 μm, 40. C @ 3. min, 2. K/min, 245. C @ 20. min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 1045.5 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
Capillary | MDN-5 | 1045. | van Loon, Linssen, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min |
Capillary | MDN-5 | 1043. | van Loon, Linssen, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min |
Capillary | OV-101 | 1012. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | DB-5 | 1034. | Savel'eva, Zenkevich, et al., 2003 | 25. m/0.20 mm/0.33 μm, Helium, 40. C @ 1. min, 5. K/min, 270. C @ 15. min |
Capillary | RTX-5 | 1083. | Sies A., Hirsch R., et al., 2002 | 20. m/0.18 mm/0.4 μm, He, 20. C @ 3.5 min, 40. K/min, 290. C @ 0.5 min |
Capillary | BP-1 | 1009. | Health Safety Executive, 2000 | 50. m/0.22 mm/0.75 μm, He, 5. K/min; Tstart: 50. C; Tend: 200. C |
Capillary | DB-5 | 1042. | Berdague, Denoyer, et al., 1991 | 60. m/0.32 mm/1.0 μm, He, 3. K/min; Tstart: 40. C; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1002. | Savelieva and Zenkevich I., 2003 | Program: not specified |
Capillary | Methyl Silicone | 1034. | Savelieva and Zenkevich I., 2003 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1662. | Beck, Higbee, et al., 2008 | 60. m/0.32 mm/0.25 μm, Helium, 30. C @ 4. min, 2. K/min, 200. C @ 30. min |
Capillary | Innowax | 1679. | Petersen, Poll, et al., 1998 | 30. m/0.25 mm/0.25 μm, 40. C @ 10. min, 6. K/min, 240. C @ 25. min |
Capillary | Carbowax 20M | 1652. | Liardon and Ledermann, 1980 | H2, 2. K/min; Column length: 39. m; Column diameter: 0.30 mm; Tstart: 60. C; Tend: 220. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP Innowax FSP | 1678. | Tasdemir, Demirci, et al., 2003 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of ideal-gas enthalpies of formation for key compounds,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]
Kozina and Skuratov, 1959
Kozina, M.P.; Skuratov, S.M.,
The enthalphy of polymerization of N-substituted lactames,
Dokl. Akad. Nauk SSSR, 1959, 127, 561-563. [all data]
Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D.,
Heats of combustion of cyclic compounds,
Bull. Chem. Thermodyn., 1958, 1, 21. [all data]
Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M.,
Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry,
J. Therm. Anal., 1978, 14, 131-150. [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]
Gude and Teja, 1994
Gude, M.T.; Teja, A.S.,
The Critical Properties of Several n-Alkanals, Tetralin and NMP,
Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Series No. 2, p.174-83. [all data]
Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J.,
The critical properties of thermally stable and unstable fluids. II. 1986 results,
AIChE Symp. Ser., 1990, 86, 279, 122-7. [all data]
Chylinski, Fras, et al., 2004
Chylinski, Krzysztof; Fras, Zbigniew; Malanowski, Stanislaw K.,
Vapor-Liquid Equilibrium for Propylene Glycol + 2-(2-Hexyloxyethoxy)ethanol and 1-Methyl-2-pyrrolidone + 1-Methoxypropan-2-ol «8224»,
J. Chem. Eng. Data, 2004, 49, 1, 18-23, https://doi.org/10.1021/je034096z
. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Palczewska-Tulinska and Oracz, 2007
Palczewska-Tulinska, Marcela; Oracz, Pawel,
Vapor Pressures of 1-Methyl-2-pyrrolidone, 1-Methyl-azepan-2-one, and 1,2-Epoxy-3-chloropropane,
J. Chem. Eng. Data, 2007, 52, 6, 2468-2471, https://doi.org/10.1021/je700398k
. [all data]
Linek, Wichterle, et al., 1996
Linek, Jan; Wichterle, Ivan; Marsh, Kenneth N.,
Vapor-Liquid Equilibria for N- Methyl-2-pyrrolidone + Benzene, +Toluene, +Heptane, and +Methylcyclohexane,
J. Chem. Eng. Data, 1996, 41, 6, 1212-1218, https://doi.org/10.1021/je9601826
. [all data]
Kneisl and Zondlo, 1987
Kneisl, Philip; Zondlo, John W.,
Vapor pressure, liquid density, and the latent heat of vaporization as functions of temperature for four dipolar aprotic solvents,
J. Chem. Eng. Data, 1987, 32, 1, 11-13, https://doi.org/10.1021/je00047a003
. [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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Bludilina, Baev, et al., 1979
Bludilina, V.I.; Baev, A.K.; Matveev, V.K.; Gaidym, I.L.; Shcherbina, E.I.,
Zh. Fiz. Khim., 1979, 53, 1052. [all data]
Lisicki and Jamróz, 2000
Lisicki, Zygmunt; Jamróz, Malgorzata E.,
(Solid + liquid) equilibria in (polynuclear aromatic+ tertiary amide) systems,
The Journal of Chemical Thermodynamics, 2000, 32, 10, 1335-1353, https://doi.org/10.1006/jcht.2000.0685
. [all data]
Nishimura, Yamaguchi, et al., 1989
Nishimura, O.; Yamaguchi, K.; Mihara, S.; Shibamoto, T.,
Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree,
J. Agric. Food Chem., 1989, 37, 1, 139-142, https://doi.org/10.1021/jf00085a033
. [all data]
Pozo-Bayon M.A., Ruiz-Rodriguez A., et al., 2007
Pozo-Bayon M.A.; Ruiz-Rodriguez A.; Pernin K.; Cayot N.,
Influence of eggs on the aroma composition of a sponge cake and on the aroma release in model studies on flavored sponge cakes,
J. Agric. Food Chem., 2007, 55, 4, 1418-1426, https://doi.org/10.1021/jf062203y
. [all data]
Cros S., Lignot B., et al., 2005
Cros S.; Lignot B.; Bourseau P.; Jaouen P.,
Reverse osmosis for the production of aromatic concentrates from mussel cooking juices: a technical assessment,
Desalination, 2005, 180, 1-3, 263-269, https://doi.org/10.1016/j.desal.2005.01.008
. [all data]
Cros, Lignot, et al., 2005
Cros, S.; Lignot, B.; Bourseau, P.; Jaouen, P.; Prost, C.,
Desalination of mussel cooking juices by electrodialysis: effect on the aroma profile,
J. Food Eng., 2005, 69, 4, 425-436, https://doi.org/10.1016/j.jfoodeng.2004.08.036
. [all data]
Aubert, Günata, et al., 2003
Aubert, C.; Günata; Ambid, C.; Baumes, R.,
Changes in physicochemical characteristics and volatile constituents of yellow- and white-fleshed nectarines during maturation and artificial ripening,
J. Agric. Food Chem., 2003, 51, 10, 3083-3091, https://doi.org/10.1021/jf026153i
. [all data]
Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D.,
Volatile constituents of Perique tobacco,
Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]
van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J.,
Identification and olfactometry of French fries flavour extracted at mouth conditions,
Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Savel'eva, Zenkevich, et al., 2003
Savel'eva, E.I.; Zenkevich, I.G.; Radilov, A.S.,
Identification the Products of Chemical Neutralization of O-Isobutyl-S-(2-diethylaminoethyl)methylthiophosphonate in the Composition of Bitumen-Salt Matrices,
Zh. Anal. Khim. (Rus.), 2003, 58, 2, 135-145. [all data]
Sies A., Hirsch R., et al., 2002
Sies A.; Hirsch R.; Löscher R.; Tablack P.; Guth H.,
Direct thermal desorption and Fast-GC-TOF-MS for a rapid quality control of hazelnuts, 10th Weurman Flavour Research Symposium, 24 - 28 June 2002, Beaune, France, 2002. [all data]
Health Safety Executive, 2000
Health Safety Executive,
MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography
in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]
Berdague, Denoyer, et al., 1991
Berdague, J.-L.; Denoyer, C.; Le Quéré, J.-L.; Semon, E.,
Volatile components of dry-cured ham,
J. Agric. Food Chem., 1991, 39, 7, 1257-1261, https://doi.org/10.1021/jf00007a012
. [all data]
Savelieva and Zenkevich I., 2003
Savelieva, E.; Zenkevich I.,
Analisi GC/MS di agenti chimici nervini,
Laboratorio 2000, 2003, 17, 6/7, 24-26. [all data]
Beck, Higbee, et al., 2008
Beck, J.J.; Higbee, B.S.; Marrill, G.B.; Roitman, J.N.,
Comparison of volatile emissions from undamaged and mechanically damaged almonds,
J, Sci. Food Argic., 2008, 88, 8, 1363-1368, https://doi.org/10.1002/jsfa.3224
. [all data]
Petersen, Poll, et al., 1998
Petersen, M.A.; Poll, L.; Larsen, L.M.,
Comparison of volatiles in raw and boiled potatoes using a mild extraction technique combined with GC odour profiling and GC-MS,
Food Chem., 1998, 61, 4, 461-466, https://doi.org/10.1016/S0308-8146(97)00119-2
. [all data]
Liardon and Ledermann, 1980
Liardon, R.; Ledermann, S.,
volatile components of fermented soya hydrolysate. II. Composition of basic fraction,
Z. Lebensm. Unters. Forsch., 1980, 170, 3, 208-213, https://doi.org/10.1007/BF01042542
. [all data]
Tasdemir, Demirci, et al., 2003
Tasdemir, D.; Demirci, B.; Demirci, F.; Dönmez, A.A.; Baser, K.H.C.; Rüedi, P.,
Analysis of the Volatile Components of Five Turkish Rhododendron Species by Headspace Solid-Phase Microextraction and GC-MS (HS-SPME-GC-MS),
Z. Naturforsch., 2003, 58c, 797-803. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature 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 ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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