2,3,3,3-Tetrafluoropropene

Chemical compound changed changed 477209907 2,3,3,3-Tetrafluorpropene Structural Formulae V.1.svg 150px skin-invert-image 2,3,3,3-Tetrafluoropropene-3D-balls.png 160 2,3,3,3-Tetrafluoropropene molecule bg-transparent 2,3,3,3-Tetrafluoroprop-1-ene HFO-1234yf; R1234yf; R-1234yf; 2,3,3,3-Tetrafluoropropylene correct chemspider 2057041 correct CAS 754-12-1 468-710-7 2776731 correct FDA P5N89242X3 3161 1/C3H2F4/c1-2(4)3(5,6)7/h1H2 FXRLMCRCYDHQFW-UHFFFAOYAB C=C(F)C(F)(F)F FC(=C)C(F)(F)F correct chemspider 1S/C3H2F4/c1-2(4)3(5,6)7/h1H2 correct chemspider FXRLMCRCYDHQFW-UHFFFAOYSA-N C3H2F4 114g/mol Colorless gas 1.1g/cm3 at 25°C (liquid); 4 (gas, relative, air is 1) -30 198.2mg/L at 24°C, 92/69/EEC, A.6 2.15, n-octanol/water, 92/69/EEC, A.8 6,067hPa at 21.1°C; 14,203hPa at 54.4°C 02 220 210 260 281 308+313 410+403 405 6.2% vol.; 12.3% vol. 2,3,3,3-Tetrafluoropropene, HFO-1234yf, is a hydrofluoroolefin (HFO) with molecular formula CH2=CFCF3. Its primary application is as a refrigerant with low global warming potential (GWP). As a refrigerant, it is designated R-1234yfSciance Fred The Transition from HFC- 134a to a Low -GWP Refrigerant in Mobile Air Conditioners HFO -1234yf https://www.epa.gov/sites/default/files/2014-09/documents/sciance.pdf 1 August 2018 General Motors Public Policy Center October 29, 2013 and marketed under the names Opteon YF by Chemours and as Solstice yf by Honeywell.Honeywell and Chemours Announce New Manufacturing Plants for HFO 1234yf https://www.aspenrefrigerants.com/news/all/honeywell-and-chemours-announce-new-manufacturing-plants-hfo-1234yf 26 July 2018 Aspen Refrigerants June 12, 2017 4 August 2020 https://web.archive.org/web/20200804000821/https://www.aspenrefrigerants.com/news/all/honeywell-and-chemours-announce-new-manufacturing-plants-hfo-1234yf dead R-1234yf is also a component of zeotropic refrigerant blend R-454B. HFO-1234yf has a GWP less than carbon dioxide,Hodnebrog Ø. Etminan M Fuglestvedt J.S Marston G Myhre G Nielsen C.J Shine K.P Wallington T.J 2008 Global warming potentials and radiative efficiencies of halocarbons and related compounds: A comprehensive review Reviews of Geophysics 51 2 300–378 10.1002/rog.20013 itself 1,430 times less potent than R-134a. For this reason, 2,3,3,3tetrafluoropropene is the pre-eminent replacement for R-134a in vehicular air conditioners. As of 2022, 90% of new U.S. vehicles are estimated to use HFO-1234yf.23 March 2022 StackPath https://www.vehicleservicepros.com/service-repair/underhood/article/21258649/meeting-the-challenge-of-r1234yf-service https://web.archive.org/web/20220326215032/https://www.vehicleservicepros.com/service-repair/underhood/article/21258649/meeting-the-challenge-of-r1234yf-service 2022-03-26 2022-05-28 www.vehicleservicepros.com Unlike previous vehicular refrigerants, 2,3,3,3tetrafluoropropene is flammable; how much risk this poses is discussed below. One drawback is it breaks down into short-chain perfluorinated carboxylic acids (PFCAs), which are persistent organic pollutants.Wang Ziyuan Wang Yuhang Li Jianfeng Henne Stephan Zhang Boya Hu Jianxin Zhang Jianbo Impacts of the Degradation of 2,3,3,3-Tetrafluoropropene into Trifluoroacetic Acid from Its Application in Automobile Air Conditioners in China, the United States, and Europe Environmental Science & Technology 30 January 2018 52 5 2819–2826 10.1021/acs.est.7b05960 29381347 2018EnST...52.2819W Adoption by automotive industry HFO-1234yf was developed by a team at DuPont, led by Barbara Haviland Minor, jointly with researchers at Honeywell.Recognizing excellence: Development of HFO-1234yf as the next generation refrigerant for the automotive industry http://www2.dupont.com/Sustainability/en_US/assets/downloads/2010_sg_award_brochure.pdf 2010 DuPont Excellence Awards Sustainable Growth 31 July 2018 3 2010 11 May 2011 https://web.archive.org/web/20110511063915/http://www2.dupont.com/Sustainability/en_US/assets/downloads/2010_sg_award_brochure.pdf dead DuPont Names Seven New DuPont Fellows http://www.dupont.com/corporate-functions/media-center/press-releases/dupont-names-seven-new-dupont-fellows.html 30 July 2018 DuPont Media Center July 17, 2014 https://web.archive.org/web/20180730170851/http://www.dupont.com/corporate-functions/media-center/press-releases/dupont-names-seven-new-dupont-fellows.html 30 July 2018 dead Their goal was to meet European directive 2006/40/EC, which went into effect in 2011 and required that all new car platforms for sale in Europe use a refrigerant in its AC system with a global warming potential (GWP) less than 150 times more potent than carbon dioxide.Directive 2006/40/EC of the European Parliament and of the Council of 17 May 2006 relating to emissions from air-conditioning systems in motor vehicles and amending Council Directive 70/156/EEC https://www.fluorocarbons.org/mac-directive-402006/ EFCTC 26 July 2018 26 July 2018 https://web.archive.org/web/20180726234049/https://www.fluorocarbons.org/mac-directive-402006/ dead HFO-1234yf was initially considered to have a 100-year GWP of 4, and is now considered to have a 100-year GWP lower than 1 (carbon dioxide has a GWP of 1.0).IPCC confirms HFO GWPs are less than 1 https://www.coolingpost.com/world-news/ipcc-confirms-hfo-gwps-are-less-than-1/ 26 July 2018 Cooling Post 3 Feb 2014Scientific Assessment of Ozone Depletion: 2014 Full Report 2014 World Meteorological Organization Global Ozone Research and Monitoring Project—Report No. 55 551 https://www.wmo.int/pages/prog/arep/gaw/ozone_2014/full_report_TOC.html Among the alternatives developed to comply with 2006/40/EC, HFO-1234yf had the lowest switching cost for automakers.Ansari Naushad A. Yadav Bipin Kumar Jitendra August 2013 Theoretical exergy analysis of HFO-1234yf and HFO-1234ze as an alternative replacement of HFC-134a in simple vapour compression refrigeration system International Journal of Scientific & Engineering Research 4 8 10.1.1.415.9796HFO-1234yf, New Dawn of Refrigerant Alternatives https://www.honeywell-refrigerants.com/india/?document=japan-air-conditioning-heating-refrigeration-news-april-2008&download=1 1 August 2018 JARN: Japan Air Conditioning, Heating & Refrigeration News April 25, 2008 40 4 1, 6, 24 It can be used as a "near drop-in replacement" for R-134a,Honeywell's low-global-warming refrigerant for vehicles approved for import, use by Japan regulators http://www51.honeywell.com/honeywell/news-events/press-releases-details/8.4.09Low-Global-WarmingRefrigerantforVehicles.html?c=31 26 July 2018 Honeywell August 4, 2009 26 July 2018 https://web.archive.org/web/20180726234159/http://www51.honeywell.com/honeywell/news-events/press-releases-details/8.4.09Low-Global-WarmingRefrigerantforVehicles.html?c=31 dead the previous automobile AC refrigerant, which has a 100-year GWP of 1430.P. Forster V. Ramaswamy P. Artaxo T. Berntsen R. Betts D.W. Fahey J. Haywood J. Lean D.C. Lowe G. Myhre J. Nganga R. Prinn G. Raga M. Schulz R. Van Dorland Solomon S. Miller H.L. Tignor M. Averyt K.B. Kristen Averyt Marquis M. Chen Z. Manning M. Qin D. Climate Change 2007: the physical science basis. Contribution of Working Group I to the fourth assessment report of the Intergovernmental Panel on Climate Change 2007 Cambridge University Press Cambridge, United Kingdom and New York, NY, USA en Chapter 2: Changes in atmospheric constituents and in radiative forcing https://www.ipcc.ch/publications_and_data/ar4/wg1/en/ch2.html 9 October 2016 1 December 2016 https://web.archive.org/web/20161201152606/http://www.ipcc.ch/publications_and_data/ar4/wg1/en/ch2.html deadAir conditioning in new vehicle models requires a greener gas https://www.autodata-group.com/ie/news/industry/air-conditioning-new-vehicle-models-requires-greener-gas/ 26 July 2018 Autodata 2017 7 April 2023 https://web.archive.org/web/20230407091147/https://www.autodata-group.com/ie/news/industry/air-conditioning-new-vehicle-models-requires-greener-gas/ dead HFO-1234yf can be handled very similarly to R-134a in repair shops, although it requires some different, specialized equipment due to its flammability.Gordon Jacques April 12, 2017 Real world experience with R1234yf: The new refrigerant is finally here; are you ready? https://www.autoserviceprofessional.com/article/97838/real-world-experience-with-r1234yf-the-new-refrigerant-is-finally-here-are-you 26 July 2018 Auto Service Professional August 2026 InternetArchiveBot Another issue affecting the compatibility between HFO-1234yf and R-134a-based systems is the choice of lubricating oil.Johnson Alec Understanding refrigerant oils https://refrigeranthq.com/understanding-refrigerant-oils/ 26 July 2018 Refrigerant HQ October 13, 2017 On July 23, 2010, General Motors announced that it would introduce HFO-1234yf in 2013 Chevrolet, Buick, GMC, and Cadillac models in the U.S.GM first to market greenhouse gas-friendly air conditioning refrigerant in U.S. https://media.gm.com/media/us/en/gm/home.detail.html/content/Pages/news/us/en/2010/July/0723_refrigerant.html 26 July 2018 GM Corporate Newsroom 2010-07-23 Shortly thereafter, Honeywell and DuPont announced that they would jointly build a manufacturing facility in Changshu, Jiangsu Province, China to produce HFO-1234yf."Automakers Go HFO", Chemical & Engineering News, July 26, 2010 In 2012, Cadillac produced the first American car using R-1234yf.Schaeber Steve February 27, 2017 R-1234yf at the 2017 PHL Auto Show https://macsworldwide.wordpress.com/2017/02/27/r-1234yf-at-the-2017-phl-auto-show/ 26 July 2018 MACS Worldwide Since then, Chrysler,David Zatz http://www.allpar.com/news/index.php/2013/10/chrysler-adopting-r1234yf Chrysler adopting R1234YF October 1, 2013 Allpar News 2018-06-16 en-US GMC,September 22, 2016 GMC hits the road with R-1234yf https://macsworldwide.wordpress.com/2016/09/22/gmc-hits-the-road-with-r-1234yf/ 26 July 2018 MACS Worldwide and FordSchaeber Steve August 17, 2016 Ford dealers selling their first MPVs with R-1234yf https://macsworldwide.wordpress.com/2016/08/17/ford-dealers-selling-their-first-mpvs-with-r-1234yf/ 26 July 2018 MACS Worldwide have all begun transitioning vehicles to R1234yf. Japanese automakers are also transitioning to R1234yf. Honda and Subaru began to introduce the new refrigerant with the 2017 models. From 2017 to 2018, BMW changed all of its models to R-1234yf. As of 2018, 50% of new vehicles from original equipment manufacturers (OEMs) are estimated to use R-1234yf.May 15, 2018 Ask the expert: How many light duty OEs use HFO-1234yf refrigerant? https://www.vehicleservicepros.com/in-the-bay/tools-equipment/air-conditioning-a-c-repair-service/r-1234yf-tools-and-equipment/article/21005163/tech-tip-current-list-of-oes-that-use-hfo1234yf-refrigerant 26 July 2018 Vehicle Service Pros In 2017, Honeywell opened a new plant in Geismar, Louisiana, to handle increased demand for the compound.Honeywell announces major investments to increase HFO-1234yf production in the United States https://www.honeywell.com/newsroom/pressreleases/2013/12/honeywell-announces-major-investments-to-increase-hfo-1234yf-production-in-the-united-states 26 July 2018 Honeywell December 10, 2013 26 July 2018 https://web.archive.org/web/20180726235518/https://www.honeywell.com/newsroom/pressreleases/2013/12/honeywell-announces-major-investments-to-increase-hfo-1234yf-production-in-the-united-states dead Honeywell starts up $300 million automotive refrigerant production facility in Louisiana https://www.honeywell.com/newsroom/pressreleases/2017/05/honeywell-starts-up-300-million-automotive-refrigerant-production-facility-in-louisiana 26 July 2018 Honeywell May 16, 2017 Honeywell and DuPont hold most patents issued for HFO-1234yf and remained the pre-eminent manufacturers in 2018.Marwa Stefen HFO-1234yf market 2018 global share and projections: Honeywell and Chemours https://theaerospacenews.com/hfo-1234yf-market-2018-global-share-and-projections-honeywell-and-chemours/204170/ 26 July 2018 The Aerospace News July 26, 2018 https://web.archive.org/web/20180726235811/https://theaerospacenews.com/hfo-1234yf-market-2018-global-share-and-projections-honeywell-and-chemours/204170/ 26 July 2018 dead Flammability Although the product is classified slightly flammable by ASHRAE, several years of testing by SAE International proved that the product could not be ignited under conditions normally experienced by a vehicle. Lewandowski Thomas A. Additional risk assessment of alternative refrigerant R-1234yf prepared for SAE International cooperative research program CRP1234-4 https://www.sae.org/standardsdev/tsb/cooperative/crp_1234-4_report.pdf SAE International 26 July 2018 July 24, 2013 Tests conducted in 2008 indicated that ignition requires temperatures exceeding 900 C F on and mixture with PAG oil.http://www.aa1car.com/library/hfo-1234yf_info_honeywell.pdf HFO-1234yf Low GWP Refrigerant Update Spatz Mark Minor Barbara July 2008 Once in flame, 2,3,3,3tetrafluoropropene releases highly corrosive and toxic gaseous hydrogen fluoride and carbonyl fluoride.Feller Michael Lux Karin Hohenstein Christian Kornath Andreas 2014-04-01 Structure and Properties of 2,3,3,3-Tetrafluoropropene (HFO-1234yf) https://www.degruyter.com/document/doi/10.5560/znb.2014-4017/html?lang=en Zeitschrift für Naturforschung B en 69 4 379–387 10.5560/znb.2014-4017 1865-7117 subscription In August 2012, Mercedes-Benz showed that the substance ignited in simulated head-on collisions. A senior Daimler engineer who ran the tests, stated "We were frozen in shock, I am not going to deny it. We needed a day to comprehend what we had just seen." When researchers sprayed 2,3,3,3tetrafluoropropene and A/C compressor oil onto a car's hot engine, the mixture burned in two out of three times.Hetzner Christiaan Coolant safety row puts the heat on Europe's carmakers https://uk.reuters.com/article/uk-europe-cars-refrigerant/coolant-safety-row-puts-the-heat-on-europes-carmakers-idUKBRE8BB0HE20121212 https://web.archive.org/web/20180726233831/https://uk.reuters.com/article/uk-europe-cars-refrigerant/coolant-safety-row-puts-the-heat-on-europes-carmakers-idUKBRE8BB0HE20121212 dead July 26, 2018 26 July 2018 Reuters December 12, 2012 In September, Daimler issued a press release, proposed a recall of cars using the refrigerant, and continued to use older refrigerants in its own designs.Bolduc Douglas A. August 8, 2013 German officials provide mixed ruling on Honeywell refrigerant Despite fire risk, agency does not seek recall of cars using HFO-1234yf http://europe.autonews.com/article/20130808/ANE/130809861/german-officials-provide-mixed-ruling-on-honeywell-refrigerant 26 July 2018 Automotive News Europe subscription The German automakers argued for development of carbon dioxide refrigerants, which they argued would be safer. In October 2012, SAE International established a new Cooperative Research Project, CRP1234-4, to extend its previous testing and investigate Daimler's claims. The investigation concluded that R-1234yf did not increase the estimated risk of vehicle fire exposure, because "the refrigerant release testing completed by Daimler was unrealistic" and "created extreme conditions that favored ignition".A heated row over coolants https://www.economist.com/business/2013/08/31/a-heated-row-over-coolants 26 July 2018 The Economist August 31, 2013 Germany's Kraftfahrt-Bundesamt Kraftfahrt-Bundesamt (KBA, Federal Motor Transport Authority) de also conducted its own tests. In their August 2013 report to the European Union, the KBA concluded that while R-1234yf was potentially more hazardous than R-134a, it did not constitute a serious danger. A 2024 CFD study in the International Journal of Refrigeration found R-1234yf stayed below its 6.2% LFL in simulated automotive evaporator leaks, while R-290 exceeded its 2.1% LFL at every monitoring point.CFD Study: A3 R-290 Formed Flammable Zones in Auto AC Leaks — A2L R-1234yf Did Not https://servicemag.org/news/cfd-flammable-zones-a2l-r1234yf-automotive-leaks ServiceMag 2026-05-23 2026-05-28Wang Linlin He Yu etal Simulation of diffusion of combustible refrigerants R1234yf and R290 leakage in automotive air conditioning International Journal of Refrigeration 2024 10.1016/j.ijrefrig.2024.07.012 Writing for Auto Service Professional, Gordon Jacques summarized the controversy: "The flammability issue has attracted a lot of attention, prompting the industry to conduct some serious third-party testing. The bottom line is this: The refrigerant will burn, but it takes a lot of heat to ignite it and it burns slowly. Almost every other fluid under the hood will light more easily and burn hotter than R1234yf, so the industry has determined that with proper A/C system design, it does not increase the chances of fire in the vehicle." Mixing HFO-1234yf with 10–11% R-134A is in development to produce a hybrid gas under review by ASHRAE for classification as A2L which is described as "virtually non-flammable". These gases are under review with the names of R451A and R451B. These mixes have GWP of ~147.https://www.coolingpost.com/world-news/r134a-alternative-is-virtually-non-flammable/ R134a alternative is "virtually non-flammable" Cooling Post 30 November 2014 en-GB 2017-06-09 Other additives have been proposed for lowering the flammability of HFO-1234yf, such as trifluoroiodomethane, which has a low GWP due to its short atmospheric lifetime, but is slightly mutagenic.US6969701B2 Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane https://patents.google.com/patent/US6969701B2/en Google patents 26 July 2018 In the environment In open atmosphere, R-1234yf degrades to trifluoroacetic acid (TFA(A)), which may accumulate in water.Kauffeld Michael June 11, 2021 Environmental impact of HFO refrigerants & alternatives for the future https://www.openaccessgovernment.org/hfo-refrigerants/112698/ Global Access Government 10.1021/es902481f Ozone and TFA Impacts in North America from Degradation of 2,3,3,3-Tetrafluoropropene (HFO-1234yf), A Potential Greenhouse Gas Replacement 2010 Luecken Deborah J. Waterland Robert L. Papasavva Stella Taddonio Kristen N. Hutzell William T. Rugh John P. Andersen Stephen O. Environmental Science & Technology 44 1 343–348 19994849 2010EnST...44..343L Hurley M.D Wallington T.J Javadi M.S Nielsen O.J 2008 Atmospheric chemistry of CF3CF=CH2: Products and mechanisms of Cl atom and OH radical initiated oxidation Chemical Physics Letters 450 4–6 263–267 10.1016/j.cplett.2007.11.051 Other HFOs have been show to produce HFC-23 as a secondary atmospheric breakdown product.McGillen Max December 11, 2023 Ozonolysis can produce long-lived greenhouse gases from commercial refrigerants Proceedings of the National Academy of Sciences 120 51 e2312714120 10.1073/pnas.2312714120 38079548 10742373 2023PNAS..12012714M free Hansen Christopher February 5, 2023 Photodissociation of CF3CHO provides a new source of CHF3 (HFC-23) in the atmosphere: implications for new refrigerants. 10.21203/rs.3.rs-199769/v1 https://www.researchsquare.com/article/rs-199769/v1 HFC-23 is a very potent greenhouse gas with a GWP100 of 14,800. However, HFO-1234yf has not been found to form HFC-23. See also 1,3,3,3-Tetrafluoropropene (HFO-1234ze) References Category:Fluoroalkenes Category:Refrigerants Category:Automotive chemicals Category:Trifluoromethyl compounds Category:Hydrofluoroolefins