Perflunafen

Structural formula
	Structure without stereochemistry
General
Non-proprietary name	Perflunafen
other names	Perfluorodecalin; Perfluoroperhydronaphthalene; PERFLUORODECALIN ( INCI ) ;
Molecular formula	C 10 F 18
External identifiers / databases
EC number	206-192-4
ECHA InfoCard	100.005.631
PubChem	9386
ChemSpider	13888074
Wikidata	Q413677
properties
Molar mass	462.08 g mol −1
Physical state	liquid
density	1.9456 g cm −3 (20 ° C); 1.94 g cm −3 (cis / trans at 25 ° C);
Melting point	−7 ° C to −10 ° C; −6.5 ° C (cis); −174.9 ° C (trans);
boiling point	140 ° C or 142 ° C; 141.5 ° C (cis / trans);
Refractive index	1.3145 (25 ° C) (cis / trans)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	50 mg kg −1 ( LD 50 , mouse , iv )
Global warming potential	7977 (based on 100 years)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Perflunafen (perfluorodecalin) is a chemical compound from the group of perfluorocarbons .

properties

Perflunafen is a colorless, inert liquid and not miscible with water. It has a high density and is considered non-toxic. However, the compound is stable in the air and has a high global warming potential .

use

Perflunafen is used in certain eye operations, for example to remove displaced lenses ( lens luxation ) from the vitreous humor , or as part of the so-called pars plana vitrectomy , to unfold the retina and put it back again. Perflunafen is used in cosmetics to improve combability, among other things. The literature describes the possible suitability of perflunafen as a blood substitute and as a contrast medium for ultrasound examinations , also for skin preparations for the treatment of wounds and burns, and for fluid ventilation . For vaccines to be encapsulated in glass microspheres , Perflunafen could be used as an inert carrier solution. It is used as a reaction medium for organic and organometallic syntheses. It is also used for gas modification of lubricants and for testing the environmental quality of sea and ground water.

Isomerism

There are two isomers of Perflunafen, the cis and the trans form. The technical product used contains both isomers in approximately the same concentration.

cis
trans

Trade names

Basic substance: Flutec PP6

Medical finished preparations for ophthalmology: DK-Line (D), Vitreo Deca (D), RT Decalin (D)

Individual evidence

↑ Entry on PERFLUORODECALIN in the CosIng database of the EU Commission, accessed on December 28, 2019.
↑ ^a ^b ^c Pharmaceutical Substance List, 12th Edition 2001, Advertising and Sales Association of German Pharmacists
↑ ^a ^b ^c ^d ^e Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 ( books.google.com ).
↑ ^a ^b Data sheet perfluorodecalin from Sigma-Aldrich , accessed on November 28, 2012 ( PDF ).
^ Entry on Perflunafen in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on August 5, 2016.
↑ G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).
↑ Keith P. Shine et al .: Perfluorodecalin: global warming potential and first detection in the atmosphere . In: Atmospheric Environment 39 (9), 2005, 1759–1763, doi: 10.1016 / j.atmosenv.2005.01.001 .
↑ Wen-Tien Tsai: Environmental Property Modeling of Perfluorodecalin and its Implications for Environmental Fate and Hazards . In: Aerosol and Air Quality Research 11, 2011, 903-907, doi: 10.4209 / aaqr.2010.12.0106 .
↑ Marina Bährle-Rapp: Springer Lexicon Cosmetics and Body Care . Springer-Verlag, 2012, ISBN 978-3-642-24688-3 ( p. 434 in the Google book search).
↑ ^a ^b B. Gschrey, W. Schwarz, T. Kimmel, B. Zeiger, S. Reitz: Implementation of the IPCC Guidelines for National Greenhouse Gas Inventories 2006 in the inventory survey of fluorinated greenhouse gases (HFCs, PFCs, SF ₆ , NF ₃ ) (PDF), in: Climate Change 17/2015, Ed .: Umweltbundesamt, p. 111 ff.
↑ Wen-Tien Tsai: Environmental Property Modeling of Perfluorodecalin and its Implications for Environmental Fate and Hazards . In: Aerosol and Air Quality Research . tape 11 , 2011, ISSN 1680-8584 , p. 903 , doi : 10.4209 / aaqr.2010.12.0106 .
^ Hans-Georg Mack, Heinz Oberhammer: The gas-phase structures of trans- and cis-perfluorodecalin. In: Journal of Molecular Structure 197, 1989, pp. 321-328, doi: 10.1016 / 0022-2860 (89) 85172-5 .

[CosIng-1] Entry on PERFLUORODECALIN in the CosIng database of the EU Commission, accessed on December 28, 2019.

[PSL-2] Pharmaceutical Substance List, 12th Edition 2001, Advertising and Sales Association of German Pharmacists

[Yaws-3] Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 ( books.google.com ).

[Sigma-4] Data sheet perfluorodecalin from Sigma-Aldrich , accessed on November 28, 2012 ( PDF ).

[ChemID-5] Entry on Perflunafen in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on August 5, 2016.

[6] G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).

[7] Keith P. Shine et al .: Perfluorodecalin: global warming potential and first detection in the atmosphere . In: Atmospheric Environment 39 (9), 2005, 1759–1763, doi: 10.1016 / j.atmosenv.2005.01.001 .

[8] Wen-Tien Tsai: Environmental Property Modeling of Perfluorodecalin and its Implications for Environmental Fate and Hazards . In: Aerosol and Air Quality Research 11, 2011, 903-907, doi: 10.4209 / aaqr.2010.12.0106 .

[9] Marina Bährle-Rapp: Springer Lexicon Cosmetics and Body Care . Springer-Verlag, 2012, ISBN 978-3-642-24688-3 ( p. 434 in the Google book search).

[Gschrey-10] B. Gschrey, W. Schwarz, T. Kimmel, B. Zeiger, S. Reitz: Implementation of the IPCC Guidelines for National Greenhouse Gas Inventories 2006 in the inventory survey of fluorinated greenhouse gases (HFCs, PFCs, SF ₆ , NF ₃ ) (PDF), in: Climate Change 17/2015, Ed .: Umweltbundesamt, p. 111 ff.

[11] Wen-Tien Tsai: Environmental Property Modeling of Perfluorodecalin and its Implications for Environmental Fate and Hazards . In: Aerosol and Air Quality Research . tape 11 , 2011, ISSN 1680-8584 , p. 903 , doi : 10.4209 / aaqr.2010.12.0106 .

[12] Hans-Georg Mack, Heinz Oberhammer: The gas-phase structures of trans- and cis-perfluorodecalin. In: Journal of Molecular Structure 197, 1989, pp. 321-328, doi: 10.1016 / 0022-2860 (89) 85172-5 .