Perfluorohexane

Last updated
Perfluorohexane
Perfluorohexane.png
Perfluorohexane-3D-vdW.png
Names
Preferred IUPAC name
Tetradecafluorohexane
Other names
FC-72,
Fluorinert FC-72,
Flutec PP1,
Perfluoro-compound FC-72
Identifiers
3D model (JSmol)
AbbreviationsPFH
ChEBI
ChemSpider
ECHA InfoCard 100.005.987 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6F14/c7-1(8,3(11,12)5(15,16)17)2(9,10)4(13,14)6(18,19)20 Yes check.svgY
    Key: ZJIJAJXFLBMLCK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6F14/c7-1(8,3(11,12)5(15,16)17)2(9,10)4(13,14)6(18,19)20
    Key: ZJIJAJXFLBMLCK-UHFFFAOYAE
  • FC(F)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F
Properties
C6F14
Molar mass 338.041845
AppearanceClear, colorless
Odor Odorless
Density 1.680 kg/m3 (Liquid)
Melting point −90 °C (−130 °F; 183 K)
Boiling point 56 °C (133 °F; 329 K)
Vapor pressure 30.9 kPa (25 °C)
Thermal conductivity 0.057 W/(m·K)
Viscosity 0.64 cP
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Lethal dose or concentration (LD, LC):
> 5 g/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Perfluorohexane (C6F14), or tetradecafluorohexane, is a fluorocarbon. It is a derivative of hexane in which all the hydrogen atoms are replaced by fluorine atoms. It is used in one formulation of the electronic cooling liquid/insulator Fluorinert for low-temperature applications due to its low boiling point of 56 °C and freezing point of −90 °C. It is odorless and colorless. Unlike typical hydrocarbons, the structure features a helical carbon backbone. [1]

Contents

Oxygen solubility

Because it is biologically inert and chemically stable, perfluorohexane has attracted attention in medicine. Like other fluorocarbons, perfluorohexane dissolves gases, including oxygen from the air, to a higher concentration than ordinary organic solvents. This effect is attributed to the weak intermolecular forces between perfluorohexane molecules, which allows "space" for gas molecules to partition into the liquid. Animals can be submerged in a bath of oxygenated perfluorohexane without drowning, as there is sufficient oxygen available in the solvent to allow respiration to continue. This effect has led to the experimental use of perfluorohexane in treating burn victims, as their lungs can be filled with either perfluorohexane vapor or in extreme cases liquid perfluorohexane, allowing breathing to continue without the problems normally seen with pulmonary edema that sometimes occur when the inside of the lungs have been burnt e.g. by inhalation of hot smoke. [2] [3] Research was particularly active on the topic of partial liquid ventilation (PLV) in the 1990s and early 2000s, however, perfluorohexane and other perfluorocarbons showed no significant improvement of patient outcomes in clinical trials. [4]

Alternatives

Perfluorohexane has extremely high global warming potential (GWP) of 9,300. This leads to a need to find low GWP alternative. Novec 649 was considered a good drop-in replacement in many applications due to its similar thermo-physical properties and having a global warming potential of 1. [5]

See also

Related Research Articles

<span class="mw-page-title-main">Hypoxia (medicine)</span> Medical condition of lack of oxygen in the tissues

Hypoxia is a condition in which the body or a region of the body is deprived of adequate oxygen supply at the tissue level. Hypoxia may be classified as either generalized, affecting the whole body, or local, affecting a region of the body. Although hypoxia is often a pathological condition, variations in arterial oxygen concentrations can be part of the normal physiology, for example, during strenuous physical exercise.

<span class="mw-page-title-main">Fluorocarbon</span> Class of chemical compounds

Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are commercial polymers, refrigerants, drugs, and anesthetics.

<span class="mw-page-title-main">Respiratory failure</span> Inadequate gas exchange by the respiratory system

Respiratory failure results from inadequate gas exchange by the respiratory system, meaning that the arterial oxygen, carbon dioxide, or both cannot be kept at normal levels. A drop in the oxygen carried in the blood is known as hypoxemia; a rise in arterial carbon dioxide levels is called hypercapnia. Respiratory failure is classified as either Type 1 or Type 2, based on whether there is a high carbon dioxide level, and can be acute or chronic. In clinical trials, the definition of respiratory failure usually includes increased respiratory rate, abnormal blood gases, and evidence of increased work of breathing. Respiratory failure causes an altered mental status due to ischemia in the brain.

<span class="mw-page-title-main">Extracorporeal membrane oxygenation</span> Technique of providing both cardiac and respiratory support

Extracorporeal membrane oxygenation (ECMO), is a form of extracorporeal life support, providing prolonged cardiac and respiratory support to persons whose heart and lungs are unable to provide an adequate amount of oxygen, gas exchange or blood supply (perfusion) to sustain life. The technology for ECMO is largely derived from cardiopulmonary bypass, which provides shorter-term support with arrested native circulation. The device used is a membrane oxygenator, also known as an artificial lung.

<span class="mw-page-title-main">Acute respiratory distress syndrome</span> Human disease

Acute respiratory distress syndrome (ARDS) is a type of respiratory failure characterized by rapid onset of widespread inflammation in the lungs. Symptoms include shortness of breath (dyspnea), rapid breathing (tachypnea), and bluish skin coloration (cyanosis). For those who survive, a decreased quality of life is common.

<span class="mw-page-title-main">Pulmonology</span> Study of respiratory diseases

Pulmonology, pneumology or pneumonology is a medical specialty that deals with diseases involving the respiratory tract. It is also known as respirology, respiratory medicine, or chest medicine in some countries and areas.

<span class="mw-page-title-main">Liquid breathing</span> Respiration of oxygen-rich liquid by a normally air-breathing organism

Liquid breathing is a form of respiration in which a normally air-breathing organism breathes an oxygen-rich liquid (such as a perfluorocarbon), rather than breathing air, by selecting a liquid that can hold a large amount of oxygen and is capable of CO2 gas exchange.

Fluorinert is the trademarked brand name for the line of electronics coolant liquids sold commercially by 3M. As perfluorinated compounds (PFCs), all Fluorinert variants have an extremely high Global Warming Potential (GWP), so should be used with caution (see below). It is an electrically insulating, stable fluorocarbon-based fluid, which is used in various cooling applications. It is mainly used for cooling electronics. Different molecular formulations are available with a variety of boiling points, allowing it to be used in "single-phase" applications, where it remains a liquid, or for "two-phase" applications, where the liquid boils to remove additional heat by evaporative cooling. An example of one of the compounds 3M uses is FC-72 (perfluorohexane, C6F14). Perfluorohexane is used for low-temperature heat-transfer applications due to its 56 °C (133 °F) boiling point. Another example is FC-75, perfluoro(2-butyl-tetrahydrofurane). There are 3M fluids that can handle up to 215 °C (419 °F), such as FC-70 (perfluorotripentylamine).

<span class="mw-page-title-main">Capnography</span> Monitoring of the concentration of carbon dioxide in respiratory gases

Capnography is the monitoring of the concentration or partial pressure of carbon dioxide (CO
2
) in the respiratory gases. Its main development has been as a monitoring tool for use during anesthesia and intensive care. It is usually presented as a graph of CO
2
(measured in kilopascals, "kPa" or millimeters of mercury, "mmHg") plotted against time, or, less commonly, but more usefully, expired volume (known as volumetric capnography). The plot may also show the inspired CO
2
, which is of interest when rebreathing systems are being used. When the measurement is taken at the end of a breath (exhaling), it is called "end tidal" CO
2
(PETCO2).

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”.

<span class="mw-page-title-main">Hypoxemia</span> Abnormally low level of oxygen in the blood

Hypoxemia is an abnormally low level of oxygen in the blood. More specifically, it is oxygen deficiency in arterial blood. Hypoxemia has many causes, and often causes hypoxia as the blood is not supplying enough oxygen to the tissues of the body.

<span class="mw-page-title-main">Alveolar lung disease</span> Medical condition

Alveolar lung diseases, are a group of diseases that mainly affect the alveoli of the lungs.

High-frequency ventilation is a type of mechanical ventilation which utilizes a respiratory rate greater than four times the normal value and very small tidal volumes. High frequency ventilation is thought to reduce ventilator-associated lung injury (VALI), especially in the context of ARDS and acute lung injury. This is commonly referred to as lung protective ventilation. There are different types of high-frequency ventilation. Each type has its own unique advantages and disadvantages. The types of HFV are characterized by the delivery system and the type of exhalation phase.

A pulmonary shunt is the passage of deoxygenated blood from the right side of the heart to the left without participation in gas exchange in the pulmonary capillaries. It is a pathological condition that results when the alveoli of parts of the lungs are perfused with blood as normal, but ventilation fails to supply the perfused region. In other words, the ventilation/perfusion ratio of those areas is zero.

<span class="mw-page-title-main">Pulmonary contusion</span> Internal bruise of the lungs

A pulmonary contusion, also known as lung contusion, is a bruise of the lung, caused by chest trauma. As a result of damage to capillaries, blood and other fluids accumulate in the lung tissue. The excess fluid interferes with gas exchange, potentially leading to inadequate oxygen levels (hypoxia). Unlike pulmonary laceration, another type of lung injury, pulmonary contusion does not involve a cut or tear of the lung tissue.

Fluorous chemistry involves the use of perfluorinated compounds or perfluorinated substituents to facilitate recovery of a catalyst or reaction product. Perfluorinated groups impart unique physical properties including high solubility in perfluorinated solvents. This property can be useful in organic synthesis and separation methods such as solid phase extraction. In practice, a perfluorinated alkyl group is incorporated into an otherwise conventional organic reagent as an affinity tag. These reagents can then be separated from organic solvents by extraction with fluorinated solvents such as perfluorohexane.

Hydrofluoroethers (HFE) are a class of organic solvents. As non-ozone-depleting chemicals, they were developed originally as a replacement for CFCs, HFCs, HCFCs, and PFCs. They are typically colorless, odorless, tasteless, low toxicity, low viscosity, and liquid at room temperature. The boiling point of HFEs vary from 50 °C to nearly 100 °C. Although 3M first developed HFEs, other manufacturers have begun producing them.

<span class="mw-page-title-main">Airway pressure release ventilation</span> Pressure control mode of mechanical ventilation

Airway pressure release ventilation (APRV) is a pressure control mode of mechanical ventilation that utilizes an inverse ratio ventilation strategy. APRV is an applied continuous positive airway pressure (CPAP) that at a set timed interval releases the applied pressure. Depending on the ventilator manufacturer, it may be referred to as BiVent. This is just as appropriate to use, since the only difference is that the term APRV is copyrighted.

<span class="mw-page-title-main">Liquid ventilator</span> Medical device

A liquid ventilator is similar to a medical ventilator except that it should be able to ensure reliable total liquid ventilation with a breatheable liquid ·. Liquid ventilators are prototypes that may have been used for animal experimentations but experts recommend continued development of a liquid ventilator toward clinical applications.

Modes of mechanical ventilation are one of the most important aspects of the usage of mechanical ventilation. The mode refers to the method of inspiratory support. In general, mode selection is based on clinician familiarity and institutional preferences, since there is a paucity of evidence indicating that the mode affects clinical outcome. The most frequently used forms of volume-limited mechanical ventilation are intermittent mandatory ventilation (IMV) and continuous mandatory ventilation (CMV). There have been substantial changes in the nomenclature of mechanical ventilation over the years, but more recently it has become standardized by many respirology and pulmonology groups. Writing a mode is most proper in all capital letters with a dash between the control variable and the strategy.

References

  1. John A. Gladysz and Markus Jurisch "Structural, Physical, and Chemical Properties of Fluorous Compounds" in István T. Horváth (Ed.) Topics in Current Chemistry 2011 "Fluorous Chemistry" doi : 10.1007/128_2011_282
  2. De Abreu, MG; Quelhas, AD; Spieth, P; Brauer, G; Knels, L; Kasper, M; Pino, AV; Bleyl, JU; Hubler, M; Bozza, F; Salluh, J; Kuhlisch, E; Giannella-Neto, A; Koch, T (Feb 2006). "Comparative effects of vaporized perfluorohexane and partial liquid ventilation in oleic acid-induced lung injury". Anesthesiology. 104 (2): 278–89. doi: 10.1097/00000542-200602000-00013 . PMID   16436847. S2CID   30310674.
  3. Bleyl, JU; Ragaller, M; Tscho, U; Regner, M; Hubler, M; Kanzow, M; Vincent, O; Albrecht, M (Jun 2002). "Changes in pulmonary function and oxygenation during application of perfluorocarbon vapor in healthy and oleic acid-injured animals". Critical Care Medicine. 30 (6): 1340–7. doi:10.1097/00003246-200206000-00034. PMID   12072692. S2CID   20292926.
  4. Kacmarek, Robert M.; Wiedemann, Herbert P.; Lavin, Philip T.; Wedel, Mark K.; Tütüncü, Ahmet S.; Slutsky, Arthur S. (2006-04-15). "Partial Liquid Ventilation in Adult Patients with Acute Respiratory Distress Syndrome". American Journal of Respiratory and Critical Care Medicine. 173 (8): 882–889. doi:10.1164/rccm.200508-1196OC. ISSN   1073-449X. PMID   16254269.
  5. "3M Novec 649 as a replacement of C6F14 in liquid cooling systems" (PDF). CERN. Retrieved April 8, 2021.