Piperazine
- Formula: C4H10N2
- Molecular weight: 86.1356
- IUPAC Standard InChIKey: GLUUGHFHXGJENI-UHFFFAOYSA-N
- CAS Registry Number: 110-85-0
- 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: Hexahydropyrazine; Antiren; Diethylenediamine; Diethyleneimine; Dispermine; Eraverm; Lumbrical; Piperazidine; Pipersol; Pyrazine hexahydride; Pyrazine, hexahydro-; Uvilon; Worm-A-Ton; Wurmirazin; 1,4-Diazacyclohexane; 1,4-Piperazine; 1,4-Diethylenediamine; Hexahydro-1,4-diazine; Piperazine, anhydrous; Asca-Trol No. 3; Piperazin; UN 2579; Vermex; Upixon; NSC 474
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- 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, Phase change data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 25. ± 6.3 | kJ/mol | Ccb | An, Zhang, et al., 1981 | ALS |
ΔfH°gas | 21.2 | kJ/mol | N/A | Bedford, Beezer, et al., 1963 | Value computed using ΔfHsolid° value of -45.6±1.6 kj/mol from Bedford, Beezer, et al., 1963 and ΔsubH° value of 66.8 kj/mol from An, Zhang, et al., 1981.; DRB |
Phase change data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 419.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 418.15 | K | N/A | Anderson and Shimanskaya, 1969 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 415.15 | K | N/A | Aroney and Le Fevre, 1960 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 383.2 | K | N/A | Anonymous, 1957 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 383.46 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 384.55 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 384.6 | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 661. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 58.00 | bar | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2.00 bar; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.738 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.29 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 67.0 ± 6.3 | kJ/mol | E | An, Zhang, et al., 1981 | ALS |
ΔsubH° | 66.8 | kJ/mol | N/A | An, Zhang, et al., 1981 | DRB |
Reaction thermochemistry data
Go To: Top, Gas 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: 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: C4H10N2 + C2H5N = C6H15N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 86. ± 2. | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: 3H2 + C4H4N2 = C4H10N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 207.2 ± 2.8 | kJ/mol | Chyd | Hafelinger and Steinmann, 1977 | liquid phase; solvent: Acetic acid |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
An, Zhang, et al., 1981
An, X.-W.; Zhang, Z.-L.; Wang, S.-N.; Yan, J.-Q.; Hu, R.-H.,
Investigation on bond energies: the heat of combustion of hippuric acid, piperazine and azacycloheptane,
Acta Chim. Sin., 1981, 39, 485-492. [all data]
Bedford, Beezer, et al., 1963
Bedford, A.F.; Beezer, A.E.; Mortimer, C.T.,
Heats of formation and bond energies. Part X. 1,2,5,6-tetrahydropyridine, piperidine, and piperazine,
J. Chem. Soc., 1963, 2039-2043. [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]
Anderson and Shimanskaya, 1969
Anderson, A.A.; Shimanskaya, M.V.,
Gas-Liquid Chromatography of some Aliphatic and Heterocyclic Polyfunctional Amines: II. Solution Thermodyn. of Amines in Fix. Phas.,
Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1969, No. 5, 527. [all data]
Aroney and Le Fevre, 1960
Aroney, M.; Le Fevre, R.J.W.,
Molecular polarizability. The conformation of various n-substituted anilines, piperidines, and piperazines,
J. Chem. Soc., 1960, 1960, 2161. [all data]
Anonymous, 1957
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Carnegie-Mellon Univ., 1957. [all data]
Witschonke, 1954
Witschonke, C.R.,
Freezing point and purity data for some organic compounds,
Anal. Chem., 1954, 26, 562-4. [all data]
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.,
Thermocynamic Properties and Ideal-Gas Enthalpies of Formation for Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino) ethylene, N,N'-Bis(2-hydroxyethyl)ethylenediamine, and 1,2,4-Tr,
J. Chem. Eng. Data, 1997, 42, 1037-52. [all data]
Dalin, Bobylev, et al., 1988
Dalin, A.R.; Bobylev, V.A.; Suslikov, V.F.; Kamskaya, O.I.; Tereshchenko, G.F.,
Nucleophilic cleavage and the formation of saturated heterocycles. VII. Kinetic and thermochemical study of reactions of aziridine with ethylene amines,
J. Gen. Chem. USSR, 1988, 58, 1868-1871. [all data]
Hafelinger and Steinmann, 1977
Hafelinger, G.; Steinmann, L.,
Heat of hydrogenation of compounds containing isolated and conjugted C=N bouble bonds,
Angew. Chem. Int. Ed. Engl., 1977, 16, 47-48. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ρc Critical density - 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.