Perfluoro(2-methyl-3-pentanone): Difference between revisions

{{short description|Chemical compound}}

| 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 ([[International Organization for Standardization|ISO]] name),<br>C6K,<br>perfluoro(2-methyl-3-pentanone),<br>heptafluoroisopropyl pentafluoroethyl ketone,<br>waterless water,<br>dry water

| 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

}}

| C=6|F=12|O=1

| Appearance = Clear, colorless

| 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 [[fluorocarbon|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 [[museum]]s, [[server room]]s, [[bank]]s, [[clean room]]s and [[hospital]]s. 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 [[Micro-encapsulation|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> in the manufacture of fire-extinguishing composite materials.<ref>{{Citation|title=Пожаротушащий композиционный материал на основе микрокапсулированного Novec 1230|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 battery|lithium-ion batteries]] for [[Solar panel|solar panels]] and [[Electric vehicle|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 [[Immersion cooling|full-immersion fluid]] in a proof of concept data center cooling system by [[Intel]] and [[Silicon Graphics International|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/5q8hd |archive-date=2014-04-10 |url-status=dead}}</ref> As it boils off easily due to its {{convert|49|°C|°F|1}} boiling point, it is used in two-phase immersion cooling system with a condensing loop running cold water. Effects of [[evaporative cooling]] was utilized to remove additional heat. 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|Large Hadron Collider’s]] [[High Luminosity Large Hadron Collider|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 [[Fluorocarbon#Nomenclature|perfluorocarbon]] (PFC) based compounds used for cooling, such as [[Fluorinert]], display high [[global warming potential]]s (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 layer|ozone]] ([[ozone depletion potential|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}}</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 |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 reaction|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}}</ref>

Novec 649/1230 is classified as a [[Per- and polyfluoroalkyl substances|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.

== See also ==

*[[Fire protection fluid]]

*[[Immersion cooling]]

*[[Liquid dielectric]]

*[[Hydrofluoroether]]

*[[Fluorinert]]

== 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]

*[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]

{{3M|state=expanded}}

[[Category:Coolants]]

[[Category:Liquid dielectrics]]

[[Category:Perfluorinated compounds]]

[[Category:3M brands]]

[[Category:Greenhouse gases]]