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Perfluoro(2-methyl-3-pentanone)

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Perfluoro(2-methyl-3-pentanone)
Names
Preferred IUPAC name
1,1,1,2,2,4,5,5,5-Nonafluoro-4-(trifluoromethyl)pentan-3-one
Other names
FK-5-1-12 (ISO name),
C6K,
perfluoro(2-methyl-3-pentanone),
heptafluoroisopropyl pentafluoroethyl ketone,
waterless water,
dry water
Identifiers
3D model (JSmol)
Abbreviations FK
ChemSpider
ECHA InfoCard 100.103.448 Edit this at Wikidata
  • InChI=1S/C6F12O/c7-2(4(10,11)12,5(13,14)15)1(19)3(8,9)6(16,17)18 checkY
    Key: RMLFHPWPTXWZNJ-UHFFFAOYSA-N checkY
  • FC(F)(F)C(F)(C(=O)C(F)(F)C(F)(F)F)C(F)(F)F
Properties
C6F12O
Molar mass 316.046 g·mol−1
Appearance Clear, colorless
Odor Near odorless
Density 1,610 kg/m3
Melting point −108 °C (−162 °F; 165 K)
Boiling point 49 °C (120 °F; 322 K)
Vapor pressure 40.4 kPa @ 25 °C
Thermal conductivity 0.059 W/m-K
Viscosity 0.64 cP
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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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)[1] intended for different industrial applications.

Novec 1230 and FK-5-1-12

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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.[2] 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[3][4] in the manufacture of fire-extinguishing composite materials.[5] 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 for solar panels and electric vehicles. In August 2019, Samsung SDI officially announced[6] 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

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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.[7] Due to its relatively low 49 °C (120.2 °F) 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 −40 °C (−40 °F) in single-phase configuration as part of Large Hadron Collider’s high luminosity upgrade.[8]

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.[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.[1][9]

Environmental safety

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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.[10] The Globally Harmonized System of Classification and Labeling of Chemicals (GHS) classifies this chemical as H412 - Harmful to aquatic life with long lasting effects.[11] Photolysis in sunlight, hydrolysis and hydration may be a significant sink of Novec 649/1230 in the environment.[12] It has very short estimated atmospheric lifetime of around 4 to 15 days.[13]

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.[14] It degrades to Trifluoroacetic acid (TFA) via photolytic degradation in sunlight.

See also

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References

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  1. ^ a b c "3M Novec 649 as a replacement of C6F14 in liquid cooling systems" (PDF). CERN. Retrieved April 8, 2021.
  2. ^ "Use of fluorinated ketones in fire extinguishing compositions". Google Patents. 3M Innovative Properties Co. Retrieved April 8, 2021.
  3. ^ Alexandra, Sertsova; Sergei, Krasilnikov; Lee, Sang-Sup; Kim, Jong-Sang (2019-10-31). "The Effect of Epoxy Resin on the Properties of Encapsulated Fire Extinguishing Agent". Fire Science and Engineering. 33 (5): 19–27. doi:10.7731/KIFSE.2019.33.5.019. ISSN 1738-7167.
  4. ^ "WO2020189900A1". worldwide.espacenet.com. Retrieved 2021-08-28.
  5. ^ Пожаротушащий композиционный материал на основе микрокапсулированного Novec 1230, archived from the original on 2021-10-23, retrieved 2021-08-28
  6. ^ Su-hyun, Song (2019-10-24). "Samsung SDI demonstrates fire-safe ESS". The Korea Herald. Retrieved 2021-08-28.
  7. ^ "Intel and SGI test full-immersion cooling for servers". ITworld. Archived from the original on 2014-04-10. Retrieved April 8, 2021.
  8. ^ "Silicon Photomultipliers in the Scintillating Fibre Tracker at the LHCb experiment" (PDF). CERN. Retrieved April 10, 2021.
  9. ^ "3M Novec fluids as alternative to perfluorocarbons for detector cooling at CERN" (PDF). CERN. Retrieved April 8, 2021.
  10. ^ "Environmental properties of Novec 1230 Fluid" (PDF). 3M. Retrieved April 8, 2021.
  11. ^ "COMPOUND SUMMARY 3-Pentanone, 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-". PubChem. Retrieved April 8, 2021.
  12. ^ "Hydrolysis and Atmospheric Oxidation Reactions of Perfluorinated Carboxylic Acid Precursors" (PDF). University of Toronto. Retrieved April 8, 2021.
  13. ^ "Technical Brief, Environmental properties of Novec 1230 Fluid" (PDF). 3M. Retrieved April 8, 2021.
  14. ^ "3M to Exit PFAS Manufacturing by the End of 2025".
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