27854-30-4

Usage

Uses

Used in Industrial Processes:
2H,2H,3H,3H-Perfluorononanoic acid is used as a surfactant, lubricant, and stain repellent in industrial processes for its unique properties that enhance the performance of various products.
Used in Textile Industry:
In the textile industry, 2H,2H,3H,3H-perfluorononanoic acid is used as a water and oil repellent finish to make fabrics resistant to stains and liquids, improving their durability and ease of maintenance.
Used in Paper and Packaging Industry:
2H,2H,3H,3H-Perfluorononanoic acid is used in the paper and packaging industry to provide water and oil resistance, enhancing the performance and durability of packaging materials.
Used in Coatings and Adhesives:
As a component in coatings and adhesives, 2H,2H,3H,3H-perfluorononanoic acid contributes to improved water and oil resistance, making these products more effective in various applications.
However, due to the potential environmental and health risks associated with 2H,2H,3H,3H-perfluorononanoic acid, there is an ongoing effort to regulate and phase out its use in various industries to minimize its impact on human health and the environment.

InChI:InChI=1/C9H5F13O2/c10-4(11,2-1-3(23)24)5(12,13)6(14,15)7(16,17)8(18,19)9(20,21)22/h1-2H2,(H,23,24)

Upstream product

• 124-38-9 carbon dioxide 
• 76598-01-1 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl magnesium iodide 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 64-18-6 formic acid 
• 25291-17-2 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene 
• 38550-44-6 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-iodononan-1-ol 
• 80806-68-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol 

Downstream Products

• 1233933-13-5 N-[4-(1,3-dioxacyclopent-2-yl)benzyl]-2H,2H,3H,3H-perfluorononamide 
• 1262770-54-6 2,5-dioxopyrrolidine-1-yl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate 
• 1256282-38-8 (2S,4R)-dibenzyl 4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoyloxy)pyrrolidine-1,2-dicarboxylate 
• 1137672-93-5 N,N'-(2,4,6-triethyl-1,3-phenylene)bis(methylene)bis(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanamide) 

Relevant academic research and scientific papers

Thermomorphic metal scavengers: A synthetic and multinuclear NMR study of highly fluorinated ketones and their application in heavy metal removal

The preparation of a ketone with two long chain perfluoroalkyl groups is reported via the coupling reaction of a perfluorinated alkylzinc reagent and a perfluoro-acid chloride. This ketone has been investigated in the heterogeneous removal of heavy metals M2+ (M = Sn, Cd, Pb, Hg) and As5+ from aqueous solutions and removal of these metals from organic solvents using the unique thermomorphic properties of the fluorous ketone. In addition, a comprehensive 13C NMR study of one of the intermediates in the synthesis, 2H,2H,3H,3H-perfluoronanoic acid, has allowed the determination of all 1JC-F and 2JC-F coupling constants. Also reported is the crystal structure of the acid CF3(CF2)5CH2CH2CO2H.

Enhanced activity of fluorinated quaternary ammonium surfactants against Pseudomonas aeruginosa

A novel series of fluorinated quaternary bisammonium surfactants has been synthesized in view to optimize their antimicrobial activities against Pseudomonas aeruginosa. As compared with commercial references, most of the new surfactants synthesized exhibit an enhanced activity which is discussed as a function of the nature of the spacer group between the quaternized nitrogen atoms and of the nature of the connector function between the nitrogen atoms and the perfluorinated carbon chains. It appears that the fluorinated "Gemini" surfactants bearing an amide connector can be an interesting alternative to hydrocarbon ammonium salts as preservatives and disinfectants against P. aeruginosa.

Synthesis and surface properties of new semi-fluorinated sulfobetaines potentially usable for 2D-electrophoresis

New semi-fluorinated amidosulfobetaines, homologs of hydrocarbon amidosulfobetaines (ASB) commonly used in two-dimensional gel electrophoresis (2DE), were prepared in three steps from 2-F-alkylethyl iodide or F-alkyl iodide. Their synthesis was described and their air-water interface properties were investigated and compared with their perhydrogenated counterpart properties. The influence of the relative lengths of the perfluorinated and hydocarbonated moieties was discussed. 2DE of a rat testicular membrane fraction was performed comparatively using one of these fluorinated sulfobetaines and its hydrocarbon homolog; these preliminary results showed the great potential of the semi-fluorinated sulfobetaines in proteomic analysis.

Preparation and liquid crystalline behaviour of a series of semifluorinated allylic monomers

A series of smectic liquid-crystalline 4,4'-biphenyl derivatives incorporating a perfluorinated segment and an allylic part have been prepared and their mesomorphic properties investigated. The preparation of these compounds has been done from 2-F-butylethyl iodide, the 2-F-hexylethyl iodide or the 2-F-octylpropanoic acid. The physical properties of these novel fluorinated materials are commented and illustrated in comparison with four homologous allylic series previously described. The choice of the molecular design of these monomers allows us to obtain dimorphism and high mesomorphic range determined from differential thermal analysis and the light microscopy.

Selective mono- and di{(perfluoroalkyl)acylation} of ferrocene

The selective synthesis of mono- and 1,1′-di{(perfluoroalkyl)acylated} ferrocenes by Friedel-Crafts acylation with (perfluoroalkyl)acyl halides is described. The acyl derivatives were further converted to the corresponding (perfluoroalkyl)alkyl ferrocenes by reduction of the carbonyl group with LiAlH4/AlCl3. Electrochemical studies of all the obtained substituted ferrocenes were carried out to assess the influence of the perfluoroalkyl ponytails on their redox behavior.

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Preparation and mesomorphic properties of highly fluorinated materials incorporating S-ethyl-lactate

The synthesis of three different chiral short molecular weight compounds have been reported. The overall compounds incorporate a linear perfluorinated tail and S-ethyl-Iactate as chiral moiety. Each compound differ to the other by one molecular parameter: a spacer carbonyloxy or oxycarbonylmethoxy or by the presence or not of an ester function between the two aromatic rings of the mesogenic core. The synthesis have been carried out from 2-F-hexylethyliodide or 2-F-hexylethanol. The mesomorphic properties have been characterized by light microscopy and by differential thermal analysis showing the peculiar effect of the spacer. The two biphenyl derivatives exhibit liquid crystal properties over a wide temperature range. The mesophase for both compounds is smectic of type A. However, the introduction of an ester function in the core contribute to enhance the melting temperature and suppress the liquid crystal behavior.

Synthese des isocyanates de 2-F-alkylethyle

Isocyanates are extremely important compounds in organic synthesis but their preparation is not always easy.One of the most convenient methods uses the acids as intermediates.In the F-alkyl series it is sometimes difficult to obtain them.We have optimized an efficient synthetic route to 2-F-alkylethyl isocyanates.