2-Chloro-1,1-difluoroethylene

2-Chloro-1,1-difluoroethene.svg 150px 2-Chloro-1,1-difluoroethene 359-10-4 9283 206-625-7 9664 QGF1P560AW C(=C(F)F)Cl 1S/C2HClF2/c3-1-2(4)5/h1H HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2 1 1 2 -138.5 SynQuest Labs, Inc. https://synquestlabs.com/Product/ProductDetail/6023 synquestlabs.com -17.7 2-Bromo-1,1-difluoroethene 1-Chloro-1,2-difluoroethene (Z) and (E) isomers (R 1122a); 2-Chloro-1,1-difluoroethene (also known as R 1122, u-HCFC-1122 or HCFO-1122) is a toxic unsaturated hydrochlorofluorocarbon which can be written as CF2=CHCl. The HCFO portion of the name stands for hydrochlorofluoroolefin. Another constitutional isomer of it, 1-chloro-1,2-difluoroethylene, is known as HCFO-1122a.2903450010 1,1,1,2-Tétrafluoroéthane (HFC-134a) https://www.douane.gouv.fr/rita-encyclopedie/public/nomenclatures/ajaxArbreNomenclatureChild.action?dateCritere=01%2F07%2F2022&sidNomenclaturePere=106997 www.douane.gouv.fr fr Formation One way to make HCFO-1122 by way of dehydrochlorination, is to heat HCFC-132b to 600 °C, preferably with some carbon tetrachloride to get a 70% yield. CH2ClCClF2 → CHCl=CF2 + HClSicard Alexandre J. Baker R. Tom Fluorocarbon Refrigerants and their Syntheses: Past to Present Chemical Reviews 9 September 2020 120 17 9164–9303 10.1021/acs.chemrev.9b00719 32809811 221180753 A lower yield results if HCFC-132a (1,1-dichloro-2,2-difluoroethane) is used: CHCl2CHF2 → CHCl=CF2 + HCl When trying to make HFC-134a from HCFC-133a, some HCFO-1122 is produced as a side product by way of dehydrofluorination. CF3CH2Cl → CHCl=CF2 + HF (low yield) Properties Shape and size 2-Chloro-1,1-difluoroethene has a flat shape with all atoms in the same plane. The two fluorine atoms can be distinguished by whether one is closer to hydrogen or chlorine F(H) or F(Cl). The bond lengths are: C=C 1.303 Å, C-F(H) 1.321 Å, C-F(Cl) 1.320 Å, C-Cl 1.731 Å, C-H 1.083 Å. For bond angles: ∠CCF(H) 123.4°, ∠CCF(Cl) 126.1°, ∠CCH 128.3°, ∠CCCl 121°.Leung Helen O. Marshall Mark D. Messinger Joseph P. Knowlton Gregory S. Sundheim Kathryn M. Cheung-Lau Jasmina C. The microwave spectra and molecular structures of 2-chloro-1,1-difluoroethylene and its complex with the argon atom Journal of Molecular Spectroscopy 1 November 2014 305 25–33 10.1016/j.jms.2014.09.011 2014JMoSp.305...25L Spectrum The infrared spectrum includes strong absorption bands at v10 at 751.1 cm−1, v5 at 971.5 and 970.2 cm−1, v4 at 1200.7 cm−1, v3 at 1341.7 cm−1, and v2 at 1747.5 cm−1.Pietropolli Charmet Andrea Ceselin Giorgia Stoppa Paolo Tasinato Nicola The Spectroscopic Characterization of Halogenated Pollutants through the Interplay between Theory and Experiment: Application to R1122 Molecules 24 January 2022 27 3 748 10.3390/molecules27030748 35164013 8839295 free Weaker absorption bands are at v7 at 578.0 and 577.4 cm−1, v6 at 844.9and 842.8 cm−1 and v1 at 3135.9 cm−1. An estimate for radiative forcing potential is 0.098 W m2 ppbv−1 and global warming potential is between 1.5 and 4.5 on 100 year time frame. The lifetime in Earth's atmosphere is only 10 to 30 days mitigating the effect of pollution. Occurrence 2-Chloro-1,1-difluoroethene may be a contaminant in HFC-134a.张 永科 赵 景婵 郭 治安 张 彦凤 韩 冰 医用HFC-134a中微量杂质的定性、定量分析 应用化学 2007 24 11 10.3969/j.issn.1000-0518.2007.11.027 Qualitative and Quantitative Analyses of Micro-impurities in Medical HFC-134a It can form by the elimination of HCl or HF from other HCFCs such as HCFC-133a: CF3CH2Cl → CF2=CHCl + HF It can be removed from the mixture by various physical processes such as absorption, or chemical processes, that fluorinate, reduce or oxidize it.Manzer L.E. An overview of the commercial development of chlorofluorocarbon (CFC) alternatives Catalysis Today March 1992 13 1 13–22 10.1016/0920-5861(92)80183-N An example specification for medical use of HFC-134a requires under 5 ppm of HCFC-1122.Noakes Tim Medical aerosol propellants Journal of Fluorine Chemistry December 2002 118 1–2 35–45 10.1016/S0022-1139(02)00191-4 2002JFluC.118...35N Humans that have been anesthetized by halothane, convert some in the body to 2-chloro-1,1-difluoroethene and then exhale it.Sharp J. Howard Trudell James R. Cohen Ellis N. Volatile Metabolites and Decomposition Products of Halothane In Man Anesthesiology 1 January 1979 50 1 2–8 10.1097/00000542-197901000-00002 760598 27245452 free Reactions When irradiated by ultraviolet light at 192 nm, 2-Chloro-1,1-difluoroethene splits off hydrogen chloride to make a carbene: (difluorovinylidene) CF2=CHCl → CF2=C: + HCl.Huang Yibo Gordon Robert J. The ultraviolet photodissociation dynamics of 2-chloro-1,1-difluoroethylene The Journal of Chemical Physics 22 January 1997 106 4 1418–1420 10.1063/1.473290 1997JChPh.106.1418H Difluorovinylidene does not convert to difluoroacetylene (FC≡CF), but instead survives and reacts with other molecules.Brahms John C. Dailey William P. Difluoropropadienone as a source of difluorovinylidene and difluorodiazoethene Journal of the American Chemical Society May 1990 112 10 4046–4047 10.1021/ja00166a056 1990JAChS.112.4046B Also HF can be eliminated to yield chlorofluoroacetylene (ClC≡CF).Martínez-Núñez Emilio Vázquez Saulo Quasiclassical trajectory calculations on the photodissociation of CF2CHCl at 193nm: Product energy distributions for the HF and HCl eliminations The Journal of Chemical Physics 8 March 2005 122 10 104316 10.1063/1.1859276 15836324 2005JChPh.122j4316M free 2-Chloro-1,1-difluoroethene can be removed from HFC-134a by oxidation with potassium permanganate.Manzer L. E. The CFC-Ozone Issue: Progress on the Development of Alternatives to CFCs Science 6 July 1990 249 4964 31–35 10.1126/science.249.4964.31 17787623 1990Sci...249...31M 11822992 Alternately oxidation can occur with hydrogen peroxide. Fluoridation can occur with HF with a chromium trioxide catalyst, producing CF3CH2Cl. With fluorine around −60°C it forms CF3CHClF.Guglielmo Giorgio Gambaretto Giampaolo Process for purifying fluoroethanes and chlorofluoroethanes https://patents.google.com/patent/US5367103 22 November 1994 An argon complex with the molecule is known. The argon atom is out of the plane of the other atoms, on the side with the chlorine atom. When it is heated with cyclopentadiene at 170 °C, bicyclic norbornene derivatives are produced.Jacobson Barry M. Bartlett Paul D. Cycloaddition. XV. Competing mechanisms in the reactions of cyclopentadiene with trifluoroethylene and 2-chloro-1,1-difluoroethylene The Journal of Organic Chemistry March 1973 38 5 1030–1041 10.1021/jo00945a035 Wen heated with hydrogen, it is dechlorinated, and becomes the saturated 1,1-difluoroethane.Lacher J. R. Kianpour A. Oetting F. Park J. D. Reaction calorimetry. The hydrogenation of organic fluorides and chlorides https://webbook.nist.gov/cgi/cbook.cgi?ID=C359104&Mask=608 1500–1508 1956 52 Trichlorosilane reacts by adding across the double bond, mostly yielding trichloro-(2,2-difluoroethyl)silane. As 2-chloro-1,1-difluoroethene levels increase, more of trichloro-(2-chloro-2,2-difluoroethyl)silane and trichloro-(2-chloro-1,1-difluoroethyl)silane are produced.Bevan William I. Haszeldine Robert N. Middleton John Tipping Anthony E. Polyfluoroalkyl compounds of silicon. Part XII. Reactions of trichlorosilane with 2-chloro- and 2-bromo-1,1-difluoroethylene Journal of the Chemical Society, Dalton Transactions 1974 21 2305 10.1039/DT9740002305 Use 2-Chloro-1,1-difluoroethene is an intermediate in the manufacture of fluorosurfactants, fluorine-containing textile finishing agents, organic silicon fluorine modified resins and other fine chemicals containing fluorine. References Category:Hydrochlorofluorocarbons Category:Haloethenes