1,1-Dichlorotetrafluoroethane

1,1-Dichlor-1,2,2,2-tetrafluorethane.svg File:1,1-Dichloro-1,2,2,2-tetrafluoroethane.png 1,1-Dichloro-1,2,2,2-tetrafluoroethane R114a; CFC-114a 374-07-2 9392 206-774-8 8AWA8IET6R 9775 1S/C2Cl2F4/c3-1(4,5)2(6,7)8 BAMUEXIPKSRTBS-UHFFFAOYSA-N C(C(F)(Cl)Cl)(F)(F)F 2 2 4 3.4 -56.6 1.3092 at 0 °C 2.78 137 mg/L benzene, diethyl ether, ethanol 1.455 g/cu cm (as a liquid under pressure) 1640 mm Hg 1,1-Dichloro-1,2,2,2-tetrafluoroethane https://pubchem.ncbi.nlm.nih.gov/compound/1_1-Dichloro-1_2_2_2-tetrafluoroethane#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 07 09 Danger 335 336 370 420 260 261 264 270 271 304+340 308+316 319 321 403+233 405 501 502 CFC-114 1,1-Dichlorotetrafluoroethane is a chlorofluorocarbon also known as CFC-114a or R114a by American Society of Heating, Refrigerating, and Air Conditioning Engineers.Deiters Ulrich K Some remarks on the nomenclature of refrigerants Fluid Phase Equilibria May 1997 132 1–2 265–270 10.1016/S0378-3812(96)03232-3 1997FlPEq.132..265D It has two chlorine atoms on one carbon atom and none on the other. It is one of two isomers of dichlorotetrafluoroethane, the other being 1,2-dichlorotetrafluoroethane, also known as CFC-114. Formation 1,1-Dichlorotetrafluoroethane can be made free from other isomers by reacting trichlorotrifluoroethane (CFC-113 or CFC-113a) with antimony pentachloride.Gumprecht William Henry Longoria John Mark Christoph Frank J. Process for manufacture of 1,1-dichlorotetrafluoroethane https://patents.google.com/patent/EP0426343A1/en en 8 May 1991 Trichlorotrifluoroethane can also be reacted with sulfur tetrafluoride or dichlorodifluoromethane with aluminium fluoride catalyst to yield 1,1-dichlorotetrafluoroethane. The use of aluminium in the catalyst favours the asymmetric molecules.Bozorgzadeh H Kemnitz E Nickkho-Amiry M Skapin T Winfield J.M Conversion of 1,1,2-trichlorotrifluoroethane to 1,1,1-trichlorotrifluoroethane and 1,1-dichlorotetrafluoroethane over aluminium-based catalysts Journal of Fluorine Chemistry January 2001 107 1 45–52 10.1016/S0022-1139(00)00350-X 2001JFluC.107...45B It can also be made in a reaction of tetrachloroethylene with hydrogen fluoride and chlorine, but this results in a mixture. Fluorinating 1,2-dichlorodifluoroethylene with fluorine produces a small amount of 1,1-dichlorotetrafluoroethane, but mostly tetrachlorotetrafluorobutene and some other chloroflurocarbons, so is not a good way.Haszeldine R. N. 849. Fluoro-olefins. Part I. The synthesis of hexafluorobuta-1 : 3-diene Journal of the Chemical Society (Resumed) 1952 4423 10.1039/JR9520004423 Properties 1,1-Dichlorotetrafluoroethane has a close boiling point (3.6°C) to the isomer 1,2-dichlorotetrafluoroethane (3.8°C), and so is difficult to separate by distillation.10.1246/cl.1994.571 Determination of 1,2-dichlorotetrafluoroethane (CFC-114) Concentration in the Atmosphere 1994 Chen Limin Makide Yoshihiro Tominaga Takeshi Chemistry Letters 23 3 571–574 Also in a gas chromatograph, it is hard to distinguish from the symmetric 1,2 isomer. Critical properties include critical temperature 145.7°C, critical pressure 4.92 MPa and critical density of 0.82 g/ml.Bruno Thomas J. Spectroscopic Library for Alternative Refrigerant Analysis 1990 U.S. Department of Commerce, National Institute of Standards and Technology https://books.google.com/books?id=PuI9AQAAIAAJ&dq=%221,1-Dichlorotetrafluoroethane%22&pg=PA1 en 25–27 1,1-Dichlorotetrafluoroethane does not ignite in air. Reactions 1,1-Dichlorotetrafluoroethane reacts with hydrogen when heated at 300 to 600°C with a palladium catalyst in a hydrodechlorination. The main reaction product is 1,1,1,2-tetrafluoroethane, but also 1-chloro-1,2,2,2-tetrafluoroethane (CF3CHClF) and 1,1,1-trifluoroethane are formed.Karpinski Zbigniew Early Kintu d'Itri Julie L. Catalytic Hydrodechlorination of 1,1-Dichlorotetrafluoroethane by Pd/Al2O3 Journal of Catalysis December 1996 164 2 378–386 10.1006/jcat.1996.0394 1,1-Dichlorotetrafluoroethane reacts with alkali metals, alkaline earths and aluminium. When heated with hydrogen over a nickel catalyst, 1,1-dichlorotetrafluoroethane is dechlorinated with replacement by hydrogen to yield a mixture of CF3CHClF and the dimer CF3CClFCClFCF3.Tomioka Satoshi Mori Tohru Ueda Wataru Morikawa Yutaka Ikawa Tsuneo A Novel Hydrodechlorinative Dimerization of Chlorofluorocarbons over Supported Ni Catalysts Chemistry Letters October 1991 20 10 1825–1826 10.1246/cl.1991.1825 Use CFC-114a was used in aerosol propellants, blowing agents, and in polyolefin foams. There was also use in refrigerants. Production was banned in by the Montreal Protocol. CFC-114a is a possible intermediate in the production of HFC-134a which can be produced by hydrogenation.Suh Dong Jin Park Tae-Jin Lee Byung-Gwon Park Kun-You Synthesis of HFC-134a by isomerization and hydrogenation Korean Journal of Chemical Engineering January 1996 13 1 75–81 10.1007/BF02705892 97614597 Atmosphere thumb|300px|left|Mixing ratio of CFC-114a in air (red). Also CFC-114 in black The ozone depletion potential of 1,1-dichlorotetrafluoroethane is 0.72.Davis Maxine E. Bernard François McGillen Max R. Fleming Eric L. Burkholder James B. UV and infrared absorption spectra, atmospheric lifetimes, and ozone depletion and global warming potentials for CCl₂FCCl₂F (CFC-112), CCl₃CClF₂ (CFC-112a), CCl₃CF₃ (CFC-113a), and CCl₂FCF₃ (CFC-114a) Atmospheric Chemistry and Physics 1 July 2016 16 12 8043–8052 10.5194/acp-16-8043-2016 2016ACP....16.8043D 102078043 free 1983/df193a7b-14de-427c-a539-238701f9e3b3 free The estimated lifetime in the atmosphere is about 100 years. The radiative efficiency is 0.28 Wm−2ppb−1. Global warming potential in 20 years is 6750. The atmospheric concentration of CFC-114a is not usually measured separately from CFC-114 due to difficulties in distinguishing them apart. In 1978 atmospheric levels of CFC-114a were 0.35 ppt. By 2020 the level was up to 1.13 ppt.Western Luke M. Vollmer Martin K. Global increase of ozone-depleting chlorofluorocarbons from 2010 to 2020 Nature Geoscience 3 April 2023 309–313 16 4 10.1038/s41561-023-01147-w 2023NatGe..16..309W 257941769 https://research-information.bris.ac.uk/en/publications/9e103fef-e61c-49c7-a1a3-902540ec1d7c 1 1983/9e103fef-e61c-49c7-a1a3-902540ec1d7c free CFC-114a appears to be emitted into the atmosphere is South East Asia.Laube Johannes C. Mohd Hanif Norfazrin Martinerie Patricia Gallacher Eileen Fraser Paul J. Langenfelds Ray Brenninkmeijer Carl A. M. Schwander Jakob Witrant Emmanuel Wang Jia-Lin Ou-Yang Chang-Feng Gooch Lauren J. Reeves Claire E. Sturges William T. Oram David E. Tropospheric observations of CFC-114 and CFC-114a with a focus on long-term trends and emissions Atmospheric Chemistry and Physics 9 December 2016 16 23 15347–15358 10.5194/acp-16-15347-2016 2016ACP....1615347L 54195362 free The atmospheric natural destruction of CFC-114a is by reaction with atomic oxygen, or breakup by ultraviolet light. As of 2014 about 250 tons per year of CFC-114a were being put into the atmosphere. References Category:Chlorofluorocarbons Category:Chlorofluoroalkanes Category:Haloethanes