Perfluorodecalin

Last updated
Perfluorodecalin
Perfluorodecaline.svg
Perfluorodecalin-3D-balls.png
Names
Preferred IUPAC name
Octadecafluorodecahydronaphthalene
Other names
Flutec PP6
F-decalin
Perflunafene
Identifiers
3D model (JSmol)
AbbreviationsPFD
ChEBI
ChemSpider
ECHA InfoCard 100.005.631 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-192-4
KEGG
PubChem CID
UNII
  • InChI=1S/C10F18/c11-1-2(12,5(17,18)9(25,26)7(21,22)3(1,13)14)6(19,20)10(27,28)8(23,24)4(1,15)16 X mark.svgN
    Key: UWEYRJFJVCLAGH-UHFFFAOYSA-N X mark.svgN
  • trans-isomer:FC1(F)C(F)(F)C(F)(F)[C@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C1(F)F
  • cis-isomer:FC1(F)C(F)(F)C(F)(F)[C@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@]2(F)C1(F)F
Properties
C10F18
Molar mass 462
AppearanceClear, colorless liquid
Density 1.917
Boiling point 142 °C (288 °F; 415 K)
10 ppm
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
None
Flash point None
None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Perfluorodecalin ( C 10 F 18) is a fluorocarbon, a derivative of decalin in which all of the hydrogen atoms are replaced by fluorine atoms. It is chemically and biologically inert and stable up to 400 °C. Several applications make use of its ability to dissolve gases.

Contents

Manufacture

It is manufactured by the fluorination of tetralin or decalin with cobalt(III) fluoride in the Fowler process. For most applications, several steps of purification are required after reaction.

Isomers

Perfluorodecalin exhibits cis-trans isomerism, as the tertiary fluorines atoms on the bridge carbon atoms can be either on the same side as each other (cis-isomer) or on opposite sides (trans-isomer). Both isomers are chemically and biologically inert and are very similar in their physical properties. The most notable difference is in the melting point, which is −3.6 °C for the cis-isomer, +18 °C for the trans-isomer, and −6.7 °C for a 50/50 mixture. [1]

Medical applications

Of all the perfluorocarbons, perfluorodecalin has probably seen the most interest in medical applications. Most applications utilize its ability to dissolve large amounts of oxygen (100 mL of perfluorodecalin at 25 °C can dissolve 49 mL of oxygen at STP [2] ).

Perfluorodecalin was an ingredient in Fluosol, an artificial blood product developed by Green Cross Corporation in the 1980s. It is also being studied for use in liquid breathing. Perfluorodecalin can be applied topically, to provide extra oxygen to a specific location, to accelerate wound healing. Organs and tissues can be stored for longer in oxygenated perfluorodecalin; the "two-layer method" uses perfluorodecalin and UW solution to preserve tissue for pancreas transplants. [3]

It is an ingredient of Perftoran, a blood substitute that also contains perfluoro-N-(4-methylcyclohexyl)-piperidine along with a surfactant, proxanol-268. It was developed in Russia and as of 2005 was marketed there. [4]

Other applications

Due to its gas-carrying capacity, perfluorodecalin has been used to enhance oxygen delivery during cell culture. [5] Perfluorodecalin has also been shown to dramatically enhance in vivo microscopy resolution of airspace-containing tissues such as mesophyll. Mounting leaves in perfluorodecalin significantly improves the optical qualities of the leaf, thereby enabling high-resolution imaging over twofold deeper into the mesophyll, compared with using water. The physiological impact of mounting the specimen in perfluorodecalin is also minimal compared to water. [6]

Perfluorodecalin is partially miscible with hydrocarbons [7] which makes it an attractive inert anti-solvent for some specialized applications, such as self-organization of perovskite nanocrystals into supercrystals (also known as superlattices). [8]

This compound is sometimes used to dissolve Teflon AF [9] (not to be confused with other Teflons, as PTFE, PFA and FEP).

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<i>Cis</i>–<i>trans</i> isomerism Pairs of molecules with same chemical formula showing different spatial orientations

Cistrans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides. Cistrans isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. Cis-trans notation does not always correspond to EZ isomerism, which is an absolute stereochemical description. In general, cistrans stereoisomers contain double bonds that do not rotate, or they may contain ring structures, where the rotation of bonds is restricted or prevented. Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes. Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used.

<span class="mw-page-title-main">Peptide bond</span> Covalent chemical bond between amino acids in a peptide or protein chain

In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 of one alpha-amino acid and N2 of another, along a peptide or protein chain.

Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group -NH
2
but is rather a secondary amine. The secondary amine nitrogen is in the protonated form (NH2+) under biological conditions, while the carboxyl group is in the deprotonated −COO form. The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate. It is encoded by all the codons starting with CC (CCU, CCC, CCA, and CCG).

<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.

A period 2 element is one of the chemical elements in the second row of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of the elements as their atomic number increases; a new row is started when chemical behavior begins to repeat, creating columns of elements with similar properties.

<span class="mw-page-title-main">Decalin</span> Chemical compound

Decalin, a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives.

<span class="mw-page-title-main">Prins reaction</span> Chemical reaction involving organic compounds

The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on reaction conditions. With water and a protic acid such as sulfuric acid as the reaction medium and formaldehyde the reaction product is a 1,3-diol (3). When water is absent, the cationic intermediate loses a proton to give an allylic alcohol (4). With an excess of formaldehyde and a low reaction temperature the reaction product is a dioxane (5). When water is replaced by acetic acid the corresponding esters are formed.

A polyproline helix is a type of protein secondary structure which occurs in proteins comprising repeating proline residues. A left-handed polyproline II helix is formed when sequential residues all adopt (φ,ψ) backbone dihedral angles of roughly and have trans isomers of their peptide bonds. This PPII conformation is also common in proteins and polypeptides with other amino acids apart from proline. Similarly, a more compact right-handed polyproline I helix is formed when sequential residues all adopt (φ,ψ) backbone dihedral angles of roughly and have cis isomers of their peptide bonds. Of the twenty common naturally occurring amino acids, only proline is likely to adopt the cis isomer of the peptide bond, specifically the X-Pro peptide bond; steric and electronic factors heavily favor the trans isomer in most other peptide bonds. However, peptide bonds that replace proline with another N-substituted amino acid are also likely to adopt the cis isomer.

<span class="mw-page-title-main">Perfluorohexane</span> Chemical compound

Perfluorohexane, or tetradecafluorohexane, is a fluorocarbon. It is a derivative of hexane in which all of 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.

Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.

<span class="mw-page-title-main">FC-75</span> Chemical compound

FC-75 is a fluorocarbon derivative of tetrahydrofuran with the chemical formula C8F16O. It is practically insoluble in water.

<span class="mw-page-title-main">Carbon–fluorine bond</span> Covalent bond between carbon and fluorine atoms

The carbon–fluorine bond is a polar covalent bond between carbon and fluorine that is a component of all organofluorine compounds. It is one of the strongest single bonds in chemistry, and relatively short, due to its partial ionic character. The bond also strengthens and shortens as more fluorines are added to the same carbon on a chemical compound. As such, fluoroalkanes like tetrafluoromethane are some of the most unreactive organic compounds.

<i>trans</i>-Cyclooctene Chemical compound

trans-Cyclooctene is a cyclic hydrocarbon with the formula [–(CH2)6CH=CH–], where the two C–C single bonds adjacent to the double bond are on opposite sides of the latter's plane. It is a colorless liquid with a disagreeable odor.

The Fowler process is an industry and laboratory route to fluorocarbons, by fluorinating hydrocarbons or their partially fluorinated derivatives in the vapor phase over cobalt(III) fluoride.

<span class="mw-page-title-main">Fluorine</span> Chemical element, symbol F and atomic number 9

Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reactive, as it reacts with all other elements except for the light inert gases.

<span class="mw-page-title-main">Fluorine-19 nuclear magnetic resonance spectroscopy</span> Analytical technique

Fluorine-19 nuclear magnetic resonance spectroscopy is an analytical technique used to detect and identify fluorine-containing compounds. 19F is an important nucleus for NMR spectroscopy because of its receptivity and large chemical shift dispersion, which is greater than that for proton nuclear magnetic resonance spectroscopy.

<span class="mw-page-title-main">Hexafluorobenzene</span> Chemical compound

Hexafluorobenzene, HFB, C
6
F
6
, or perfluorobenzene is an organofluorine compound. In this derivative of benzene, all hydrogen atoms have been replaced by fluorine atoms. The technical uses of the compound are limited, although it has some specialized uses in the laboratory owing to distinctive spectroscopic properties.

Perfluoromethyldecalin is a fluorocarbon liquid—a perfluorinated derivative of the hydrocarbon methyldecalin. It is chemically and biologically inert. It is mainly of interest as a blood substitute, exploiting the high solubility of air in this solvent.

1,2-Difluoroethane is a saturated hydrofluorocarbon containing an atom of fluorine attached to each of two carbons atoms. The formula can be written CH2FCH2F. It is an isomer of 1,1-difluoroethane. It has a HFC name of HFC-152 with no letter suffix. When cooled to cryogenic temperatures it can have different conformers, gauche and trans. In the liquid form these are about equally abundant and easily interconvert. As a gas it is mostly the gauche form.

References

  1. "Flutec PP Fluorocarbon Liquids", ISC Chemicals Ltd, table E5-2/4
  2. "Perfluorodecalin" (PDF). F2 Chemicals Ltd.
  3. For instance, Witkowski, P.; Liu, Z.; Guo, Q.; Poumian-Ruiz, E.; Cernea, S.; Herold, K.; Hardy, M.A. (2005). "Two-Layer Method in Short-Term Pancreas Preservation for Successful Islet Isolation". Transplantation Proceedings. 37 (8): 3398–401. doi:10.1016/j.transproceed.2005.09.050. PMID   16298606.
  4. Maevsky, E; Ivanitsky, G; Bogdanova, L; Axenova, O; Karmen, N; Zhiburt, E; Senina, R; Pushkin, S; Maslennikov, I; Orlov, A; Marinicheva, I (2005). "Clinical results of Perftoran application: present and future". Artificial Cells, Blood Substitutes, and Biotechnology. 33 (1): 37–46. doi:10.1081/BIO-200046654. PMID   15768564. S2CID   39902507.
  5. King, A. T.; Mulligan, B. J.; Lowe, K. C. (1989). "Perfluorochemicals and Cell Culture". Nature Biotechnology. 7 (10): 1037–1042. doi:10.1038/nbt1089-1037. S2CID   25329991.
  6. Littlejohn, George R.; Gouveia, João D.; Edner, Christoph; Smirnoff, Nicholas; Love, John (2010). "Perfluorodecalin enhances in vivo confocal microscopy resolution of Arabidopsis thaliana mesophyll" (PDF). New Phytologist. 186 (4): 1018–25. doi: 10.1111/j.1469-8137.2010.03244.x . hdl:10026.1/9344. PMID   20374500.
  7. Bernardo-Gil, Gabriela S.; Soares, Luis J. S. (July 1, 1987). "Mutual binary solubilities: perfluorodecalin/hydrocarbons". Journal of Chemical & Engineering Data. 32 (3): 327–329. doi:10.1021/je00049a014. hdl: 1822/16619 . ISSN   0021-9568.
  8. Baranov, Dmitry; Toso, Stefano; Imran, Muhammad; Manna, Liberato (2019-02-07). "Investigation into the Photoluminescence Red Shift in Cesium Lead Bromide Nanocrystal Superlattices". The Journal of Physical Chemistry Letters. 10 (3): 655–660. doi:10.1021/acs.jpclett.9b00178. ISSN   1948-7185. PMC   6477804 . PMID   30676762.
  9. "Teflon AF". Sigma Aldrich.