Bis(2-chloroethyl) ether
- Formula: C4H8Cl2O
- Molecular weight: 143.012
- IUPAC Standard InChIKey: ZNSMNVMLTJELDZ-UHFFFAOYSA-N
- CAS Registry Number: 111-44-4
- 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: s-Dichloroethyl ether; Ethane, 1,1'-oxybis[2-chloro-; Ether, bis(2-chloroethyl); β,β'-Dichlorodiethyl ether; β,β'-Dichloroethyl ether; Bis(β-chloroethyl) ether; Bis(chloro-2-ethyl) oxide; Chlorex; Di(β-chloroethyl) ether; DCEE; Khloreks; 1-Chloro-2-(β-Chloroethoxy)ethane; 2-Chloroethyl ether; 2,2'-Dichlorethyl ether; 2,2'-Dichlorodiethyl ether; 2,2'-Dichloroethyl ether; 2,2'-Dichlorodiethyl oxide; sym-Dichloroethyl ether; Chloroethyl ether; Clorex; Di(2-chloroethyl) ether; Dichloroether; Dichloroethyl ether; Dichloroethyl oxide; Dwuchlorodwuetylowy eter; Ether dichlore; ENT 4,504; Oxyde de chlorethyle; 1,1'-Oxybis(2-chloroethane); 1,5-Dichloro-3-oxapentane; 2,2'-Dichloorethylether; 2,2'-Dichlor-diaethylaether; 2,2'-Dicloroetiletere; Rcra waste number U025; UN 1916; Diethylene glycol dichloride; Ether, bis(chloroethyl); Beta,beta'-dichloroethyl ether; BCEE; NSC 406647
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Phase change data
Go To: Top, 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
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 |
---|---|---|---|---|---|
Tboil | 451.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 451. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 451.80 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 451. | K | N/A | Earp and Glasstone, 1935 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 226.25 | K | N/A | Tschamler, Richter, et al., 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
340.2 | 0.020 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
49.8 | 312. | A | Stephenson and Malanowski, 1987 | Based on data from 297. to 452. K. See also Stull, 1947.; AC |
45.237 | 273. | V | Gallaugher and Hibbert, 1937 | ALS |
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 |
---|---|---|---|---|---|
296.7 to 451.7 | 4.81729 | 1990.755 | -37.803 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.39 | 226.5 | Domalski and Hearing, 1996 | AC |
8.385 | 226.5 | Tschamler, 1948 | DH |
Gas Chromatography
Go To: Top, 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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 945.9 | Sun and Stremple, 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 325. C |
Capillary | OV-1 | 948. | Kostiainen, 2000 | 15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 280. C @ 10. min |
Capillary | SE-54 | 984. | Kostiainen, 2000 | 25. m/0.32 mm/0.25 μm, He, 40. C @ 1. min, 10. K/min, 280. C @ 10. min |
Capillary | Ultra-1 | 951.52 | Richmond and Pombo-Villar, 1997 | 25. m/0.32 mm/0.52 μm, 15. K/min, 320. C @ 10. min; Tstart: 35. C |
Capillary | DB-1 | 948. | D'agostino and Provost, 1988 | 15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 300. C @ 5. min |
Capillary | DB-5 | 984. | D'agostino and Provost, 1988 | 15. m/0.32 mm/0.25 μm, 50. C @ 2. min, 10. K/min, 300. C @ 5. min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 954. | Zenkevich, Eliseenkov, et al., 2011 | 25. m/0.20 mm/0.25 μm, Nitrogen, 6. K/min; Tstart: 40. C; Tend: 220. C |
Capillary | SE-54 | 989. | Harland, Cumming, et al., 1986 | He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 954. | Zenkevich and Chupalov, 1996 | Program: not specified |
Capillary | DB-1 | 948. | Tarjan, Nyiredy, et al., 1989 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 956. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | Carbowax 20M-TPA | 1536. | Szymanowski, Kusz, et al., 1990 | Chromosorb W AW DMCS, 100. C @ 1. min, 5. K/min; Column length: 1.6 m; Tend: 220. C |
Packed | Carbowax 20M-TPA | 1536. | Szymanowski, Kusz, et al., 1990, 2 | Chromosorb W AW DMCS, 100. C @ 1. min, 5. K/min; Column length: 1.6 m; Tend: 220. C |
Packed | Carbowax 20M-TPA | 1536. | Szymanowski, Kusz, et al., 1989 | Ar, Chromosorb W AW DMCS, 100. C @ 1. min, 5. K/min; Column length: 1.6 m; Tend: 220. C |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 156.2 | Donnelly, Abdel-Hamid, et al., 1993 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min |
References
Go To: Top, 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.
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]
Lecat, 1947
Lecat, M.,
Orthobaric Azeotropes of Sulfides,
Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]
Earp and Glasstone, 1935
Earp, D.P.; Glasstone, S.,
Dielectric polarisation and molecular-compound formation in solution,
J. Chem. Soc., 1935, 1935, 1709. [all data]
Tschamler, Richter, et al., 1949
Tschamler, H.; Richter, E.; Wettig, F.,
Mixtures of Primry Aliphatic Alcohols with Chlorex and Other Organic Substances. Binary Liquid Mixtures XII.,
Monatsh. Chem., 1949, 80, 749. [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]
Gallaugher and Hibbert, 1937
Gallaugher, A.F.; Hibbert, H.,
Studies on reactions relating to carbohydrates and polysaccharides. LV. Vapor pressures of the polyethylene glycols and their derivatives,
J. Am. Chem. Soc., 1937, 59, 2521-2525. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Tschamler, 1948
Tschamler, H.,
Uber binare flussige Mischungen I. Mischungswarment, Volumseffekte und Zustandsdiagramme von chlorex mit benzol und n-alkylbenzolen,
Monatsh. Chem., 1948, 79, 162-177. [all data]
Sun and Stremple, 2003
Sun, G.; Stremple, P.,
Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]
Kostiainen, 2000
Kostiainen, O.,
Gas Chromatography in Screening of Chemicals Related to the Chemical Weapons Convention
in Encyclopedia of Analytical Chemistry, Meyers, R.A., ed(s)., John Wiley Sons Ltd, Chichester, 2000, 963-979. [all data]
Richmond and Pombo-Villar, 1997
Richmond, R.; Pombo-Villar, E.,
Short communication. Gas chromatography-mass spectrometry coupled with pseudo-Sadtler retention indices, for the identification of components in the essential oil of Curcuma longa L.,
J. Chromatogr. A, 1997, 760, 2, 303-308, https://doi.org/10.1016/S0021-9673(96)00802-3
. [all data]
D'agostino and Provost, 1988
D'agostino, P.A.; Provost, L.R.,
Gas chromatographic retention indices of sulphur vesicants and related compounds,
J. Chromatogr., 1988, 436, 399-411, https://doi.org/10.1016/S0021-9673(00)94599-0
. [all data]
Zenkevich, Eliseenkov, et al., 2011
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N.; Ukolov, A.I.,
Identification of the products of nonregioselective organic reactions by chromatography - mass spectrometry: chloro derivatives of dialkyl ethers,
Rus. J. Anal. Chem., 2011, 66, 14, 1445-1454, https://doi.org/10.1134/S1061934811140218
. [all data]
Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E.,
The Kovats indexes of some organic micropollutants on an SE54 capillary column,
EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M.,
Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography,
J. Chromatogr., 1989, 472, 1-92, https://doi.org/10.1016/S0021-9673(00)94099-8
. [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]
Szymanowski, Kusz, et al., 1990
Szymanowski, J.; Kusz, P.; Dziwinski, E.,
Degradation and analysis of commercial polyoxyethylene glycol mono(4-alkylphenyl) ethers,
J. Chromatogr., 1990, 511, 325-332, https://doi.org/10.1016/S0021-9673(01)93295-9
. [all data]
Szymanowski, Kusz, et al., 1990, 2
Szymanowski, J.; Kusz, P.; Dziwinski, E.; Latocha, Cz.,
Degradation and analysis of oligooxyethylene glycol mono(4-tert.-octylphenyl) ethers in the presence of acetyl chloride,
J. Chromatogr., 1990, 502, 407-415, https://doi.org/10.1016/S0021-9673(01)89606-0
. [all data]
Szymanowski, Kusz, et al., 1989
Szymanowski, J.; Kusz, P.; Dziwinski, E.; Szewczyk, H.; Pyzalski, K.,
Degradation and Analysis of Polyoxyethylene Monoalkyl Ethers in the Presence of Acetyl Chloride and Ferric Chloride,
J. Chromatogr., 1989, 469, 197-208, https://doi.org/10.1016/S0021-9673(01)96455-6
. [all data]
Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F.,
Application of gas chromatographic retention properties to the identification of environmental contaminants,
J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I
. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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