Perfluoro(2-methyl-3-pentanone)

{{short description|Chemical compound}} {{chembox | verifiedrevid = 443675632 | ImageFileL1 = Novec-1230-2D-skeletal.png | ImageFileR1 = Novec-1230-3D-balls.png | PIN = 1,1,1,2,2,4,5,5,5-Nonafluoro-4-(trifluoromethyl)pentan-3-one | OtherNames = FK-5-1-12 (ISO name), C6K, perfluoro(2-methyl-3-pentanone), heptafluoroisopropyl pentafluoroethyl ketone, waterless water, dry water | Section1 = {{Chembox Identifiers | Abbreviations = FK | CASNo_Ref = {{cascite|correct|??}} | CASNo = 756-13-8 | PubChem = 2782408 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2062563 | SMILES = FC(F)(F)C(F)(C(=O)C(F)(F)C(F)(F)F)C(F)(F)F | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6F12O/c7-2(4(10,11)12,5(13,14)15)1(19)3(8,9)6(16,17)18 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RMLFHPWPTXWZNJ-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C=6|F=12|O=1 | Appearance = Clear, colorless liquid | Odor = Near odorless | Density = 1,610{{nbsp}}kg/m3 | MeltingPtC = −108 | BoilingPtC = 49 | Solubility = | Viscosity = 0.64{{nbsp}}cP | VaporPressure = 40.4{{nbsp}}kPa @ 25 °C | ThermalConductivity = 0.059 W/m-K }} }}

'''Perfluoro(2-methyl-3-pentanone)''' is a fluorinated ketone with the structural formula CF3CF2C(=O)CF(CF3)2, a fully-fluorinated analog of ethyl isopropyl ketone. It is used as an electronics coolant liquid and fire protection fluid sold commercially by 3M under brand names such as '''Novec 1230''', '''Novec 649''', and '''FK-5-1-12'''. It is also known as "waterless water" or "dry water".

==Applications== 3M produces perfluoro(2-methyl-3-pentanone) under different brand names of '''Novec 1230''' and '''Novec 649'''. These two products have different purity grades (>99% and >99.9%, respectively)<ref name="CERN-1">{{cite web |url= https://twiki.cern.ch/twiki/pub/LHCb/C6K/Novec_Memo_1.2.pdf |title= 3M Novec 649 as a replacement of C6F14 in liquid cooling systems |website= |publisher= CERN |access-date= April 8, 2021}}</ref> intended for different industrial applications.

===Novec 1230 and FK-5-1-12=== Novec 1230 is used as gaseous fire suppression agent in scenarios where water-based fire suppression (for example, from a fire sprinkler) would be impractical or where it could damage expensive equipment or property, such as museums, server rooms, banks, clean rooms and hospitals. It functions by rapidly removing heat to extinguish a fire before it starts; also, its density enables it to displace air and thereby deprive the fire of oxygen. Novec 1230 can be used in both total/partial/localized flooding systems, and directional spray-type applications; it is also used in portable extinguishers for specialized applications. The Patent for Novec 1230 as fire extinguishant ended on July 19, 2020.<ref>{{cite web |url= https://patents.google.com/patent/EP1261398B1/en?q=Novec1230&assignee=3M |title= Use of fluorinated ketones in fire extinguishing compositions |website= Google Patents |publisher= 3M Innovative Properties Co |access-date= April 8, 2021}}</ref> Since the expiry of the patent, multiple companies have brought equivalent products to market under the chemical name FK-5-1-12.

Recently, it has found active use in microencapsulated form<ref>{{Cite journal|last1=Alexandra|first1=Sertsova|last2=Sergei|first2=Krasilnikov|last3=Lee|first3=Sang-Sup|last4=Kim|first4=Jong-Sang|date=2019-10-31|title=The Effect of Epoxy Resin on the Properties of Encapsulated Fire Extinguishing Agent|journal=Fire Science and Engineering|language=English|volume=33|issue=5|pages=19–27|doi=10.7731/KIFSE.2019.33.5.019|issn=1738-7167|doi-access=free}}</ref><ref>{{Cite web|title=WO2020189900A1|url=https://worldwide.espacenet.com/patent/search/family/071141873/publication/WO2020189900A1?q=WO2020189900A1|access-date=2021-08-28|website=worldwide.espacenet.com}}</ref><ref>{{Cite patent|number=RU2776377C1|title=Способ получения стабильного микрокапсулированного огнетушащего агента на основе перфторкетона|gdate=2022-07-19|invent1=Серцова|invent2=Красильников|inventor1-first=Александра Анатольевна|inventor2-first=Сергей Валерьевич|url=https://patents.google.com/patent/RU2776377C1/ru}}</ref> in the manufacture of fire-extinguishing composite materials.<ref>{{Citation|title=Пожаротушащий композиционный материал на основе микрокапсулированного Novec 1230| date=21 June 2020 |url=https://www.youtube.com/watch?v=GUtWKFjMSNM| archive-url=https://ghostarchive.org/varchive/GUtWKFjMSNM?url=https://www.youtube.com/watch?v=GUtWKFjMSNM| archive-date=2021-10-23|language=en|access-date=2021-08-28}}{{cbignore}}</ref> Samsung SDI is using this product to extinguish fires in the early stages of modular high-capacity storage systems (ESS) based on lithium-ion batteries<ref>{{Cite AV media |url=https://www.youtube.com/watch?v=x6_TGOMLipg |title=MFA TECH - LiPo battery pack protection with fire extinguishing cover |date=2024-06-05 |last=Sergei Krasilnikov |access-date=2025-08-28 |via=YouTube}}</ref> for solar panels and electric vehicles. In August 2019, Samsung SDI officially announced<ref>{{Cite web|last=Su-hyun|first=Song|date=2019-10-24|title=Samsung SDI demonstrates fire-safe ESS|url=http://www.koreaherald.com/view.php?ud=20191024000784|access-date=2021-08-28|website=The Korea Herald|language=en}}</ref> its investment of $169 million into fire-extinguishing composite materials based on microencapsulated Novec 1230. The firm later reported that UL9540A testing for this product was passed.

===Novec 649=== Novec 649 is a low-temperature heat-transfer fluid. It has been used as a full-immersion fluid in a proof of concept data center cooling system by Intel and SGI.<ref>{{cite web |url= http://www.itworld.com/hardware/413707/intel-and-sgi-test-full-immersion-cooling-servers |title= Intel and SGI test full-immersion cooling for servers |website= ITworld |publisher= |access-date= April 8, 2021 |archive-url= https://archive.today/20140410121852/http://www.itworld.com/hardware/413707/intel-and-sgi-test-full-immersion-cooling-servers |archive-date=2014-04-10 |url-status=dead}}</ref> Due to its relatively low {{convert|49|°C|°F|1}} boiling point, it is used as a heat transfer fluid in two-phase immersion cooling systems. Within these systems evaporative cooling is utilized to remove excess heat generated from immersed technology. The heat is then removed from the vaporous Novec 649 using a condensing loop typically running cold water. Novec 649 is also being considered to be used for cooling silicon photomultiplier (SiPM) sensors to {{convert|-40|°C|°F}} in single-phase configuration as part of Large Hadron Collider’s high luminosity upgrade.<ref name="CERN-3">{{cite web |url=https://agenda.infn.it/event/17801/contributions/99220/attachments/67167/82428/LHCbSiPMWorkshop.pdf |title= Silicon Photomultipliers in the Scintillating Fibre Tracker at the LHCb experiment |website= |publisher= CERN |access-date= April 10, 2021}}</ref>

Traditional perfluorocarbon (PFC) based compounds used for cooling, such as Fluorinert, display high global warming potentials (GWPs), typically 5,000 to 10,000 times that of CO2.<ref name="CERN-1" /> Novec 649 was chosen as a good drop-in replacement due to it having similar thermo-physical properties to Fluorinert FC-72 (perfluorohexane, C6F14) while exhibiting a very low global warming potential of 1.<ref name="CERN-1" /><ref name="CERN-2">{{cite web |url=https://indico.cern.ch/event/444246/attachments/1151300/1652860/FI_presentation_8.09.2015.pdf |title= 3M Novec fluids as alternative to perfluorocarbons for detector cooling at CERN |website= |publisher= CERN |access-date= April 8, 2021}}</ref>

==Environmental safety== Novec 649/1230 does not deplete ozone (ODP 0) and has a global warming potential of 1 (over 100 years), equivalent to that of carbon dioxide.<ref>{{cite web |url= https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf |title= Environmental properties of Novec 1230 Fluid |website= |publisher= 3M |access-date= April 8, 2021 |archive-date= January 23, 2021 |archive-url= https://web.archive.org/web/20210123180357/https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf |url-status= dead }}</ref> The Globally Harmonized System of Classification and Labeling of Chemicals (GHS) classifies this chemical as H412 - Harmful to aquatic life with long lasting effects.<ref>{{cite web |url= https://pubchem.ncbi.nlm.nih.gov/compound/Perfluoro_2-methyl-3-pentanone#section=Hazards-Identification |archive-url= https://web.archive.org/web/20210410142653/https://pubchem.ncbi.nlm.nih.gov/compound/Perfluoro_2-methyl-3-pentanone#section=Hazards-Identification |url-status= dead |archive-date= April 10, 2021 |title= COMPOUND SUMMARY 3-Pentanone, 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)- |website= PubChem |publisher= |access-date= April 8, 2021}}</ref> Photolysis in sunlight, hydrolysis and hydration may be a significant sink of Novec 649/1230 in the environment.<ref>{{cite web |url= https://tspace.library.utoronto.ca/bitstream/1807/35854/3/Jackson_Derek_A_201306_PhD_thesis.pdf |title= Hydrolysis and Atmospheric Oxidation Reactions of Perfluorinated Carboxylic Acid Precursors |website= |publisher= University of Toronto |access-date= April 8, 2021}}</ref> It has very short estimated atmospheric lifetime of around 4 to 15 days.<ref>{{cite web |url= https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf |title= Technical Brief, Environmental properties of Novec 1230 Fluid |website= |publisher= 3M |access-date= April 8, 2021 |archive-date= January 23, 2021 |archive-url= https://web.archive.org/web/20210123180357/https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf |url-status= dead }}</ref>

Novec 649/1230 is classified as a PFAS substance. In December 2022, 3M announced that it would cease production of all PFAS products by 2025, including Novec 649/1230.<ref>{{cite web | url=https://news.3m.com/2022-12-20-3M-to-Exit-PFAS-Manufacturing-by-the-End-of-2025 | title=3M to Exit PFAS Manufacturing by the End of 2025 }}</ref> It degrades to Trifluoroacetic acid (TFA) via photolytic degradation in sunlight.

== References == <references />

== External links ==

*[https://www.3m.co.uk/3M/en_GB/novec-uk/applications/fire-suppression/ 3M Novec 1230 Website] *[https://www.3m.com/3M/en_US/company-us/all-3m-products/~/3M-Novec-649-Engineered-Fluid/?N=5002385+3290667401&rt=rud 3M Novec 649 product page] *[https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf Technical Brief, Environmental properties of Novec 1230 Fluid] {{Webarchive|url=https://web.archive.org/web/20210123180357/https://multimedia.3m.com/mws/media/311627O/3mtm-novectm-1230-fire-protection-fluid-environmental-prop.pdf |date=2021-01-23 }} *[https://multimedia.3m.com/mws/media/569865O/3m-novec-engineered-fluid-649.pdf Data Sheets of Novec 649 Fluid] *[https://multimedia.3m.com/mws/mediawebserver?mwsId=SSSSSuUn_zu8l00x482xNx29Mv70k17zHvu9lxtD7SSSSSS-- MSDS for Novec 1230] *[https://patents.google.com/patent/EP1261398B1/en?q=Novec1230&assignee=3M Patent for Novec 1230] *[https://www.epa.gov/snap/substitutes-total-flooding-agents United States Environmental Protection Agency Substitutes in Total Flooding Agents] *[https://twiki.cern.ch/twiki/pub/LHCb/C6K/Novec_Memo_1.2.pdf 3M Novec 649 as a replacement of C6F14 in liquid cooling systems]

Category:Coolants Category:Fire suppression agents Category:Ketones Category:Liquid dielectrics Category:Perfluorinated compounds Category:3M brands Category:Greenhouse gases