Fluorinated alkyl sulfates

We recently prepared various types of differently fiuorinated alkyl sulfate ILs and discovered that the hydrophobicity was dependent on the content ratio of the fluorine on the alkyl sulfate anion and 2,2,3,3,4,4,5,5-octafiuoropentyl sulfate salts showed hydrophobic properties. Melting point and viscosity were also dependent on the fluorine contents of the anionic part, while conductivity was determined by the cationic part and not influenced by the fluorine contents. Efficient lipase-catalyzed transesterificafion was demonstrated using hydrophobic 1-butyl-3-methylimidazolium 2,2,3,3,4,4,5,5-octafiuoropentyl sulfate ([bmim][C5E8]) as solvent (Eig. 6). ... 

Another approach to get new liquid crystals is the lateral fluorination of the stilbazole ligands,337 which is a common and highly effective tool to exert control over mesomorphism, crystal phase stability, and physical properties. Other modifications include the use of more alkoxy substituents and other alkyl sulfate anions.338-344 Ionic silver amino complexes also display liquid crystalline behavior at rather low temperatures they are of the form [Ag(NH2 -CJl +OJX (X = N03, n = 6,8,10,12,14 X = BF4, = 8,10,12,14).345... 

At the end of the 1990s statistics show that the non-ionic surfactants achieved the highest growth in production rates world-wide, though anionic surfactants (anionics) maintained the dominant position in the surfactant market. Today they are produced in a larger variety by the petrochemical industry than all other types of surfactants. Their production spectrum covers alkyl sulfates (ASs), secondary alkane sulfonates (SASs) and aryl sulfonates and carboxylates via derivatives of partly fluorinated or perfluorinated alkyl surfactants to compounds with an alkylpolyglycolether substructure combined with an anionic moiety such as alkylether sulfates (AESs), phosphates, phosphonates or carboxylates. 

Addition to atkenes. Although this reagent has been studied mainly for electrophilic fluorination,1 it does add to alkenes to give cis-selective vic-fluoro alkyl sulfates with some preference for anft -Markovnikov addition. The adducts can be converted into fluoro ethoxysulfates by reaction with (C2H5)jO+BF4 .2... 

Tsukada Y, Iwamoto K, Eurutani H, et al. Preparation of novel hydro-phobic fluorine-substituted-alkyl sulfate ionic liquids and application as an efficient reaction medium for lipase-catalyzed reaction. Tetrahedron Utters. 2006. 47, 1801-1804. 

Surfactants used in the polymerization are water-soluble, halogenated surfactants. They are in particular fluorinated surfactant such as ammonium, substituted ammonium, quarternary ammonium, or alkali metal salts of perfluorinated or partially fluorinated alkyl carboxylates, monoalkyl phosphate esters, alkyl ether or polyether carboxylates, alkyl sulfonates, and alkyl sulfates. 

IC-MS has also been applied for the characterization of ionic liquids (IL) and for the investigation of their long-term stability under process-like conditions. The term ionic liquid commonly refers to a class of molten salts that are by definition liquid below 100 °C. They usually consist of bulky organic cations such as alkylated imidazole, pyrrole, or pyridine derivatives, or quatemized alkyl amines and alkyl phosphines. Common counterions are halides, alkyl sulfates, fluorinated hydrocarbons, carboxylic acids, or amino acids [268]. The physical and chemical properties of ILs are customizable by different cation-anion combinations and by the length of the alkyl chain of the cation. Depending on the... 

In addition to the organic solvents described above, there are quite a few more organic compounds considered as solvent candidates for Li-ion battery electrolytes. In many cases, these molecules are more appropriate as additives instead of solvents due to the inferior physical and electrochemical properties of the resulting electrolyte if such molecules are used in high concentration. These molecules include the non-fluorinated and fluorinated varieties of alkyl sulfates [113], alkyl sulfites [21, 59, 63], alkyl phosphates [66], and phosphazenes [84]. Some of them have been employed as SEI formation additives or flame retardant additives and will be discussed in the respective sections of Chap. 9. 

All lation. In alkylation, the dialkyl sulfates react much faster than do the alkyl haHdes, because the monoalkyl sulfate anion (ROSO ) is more effective as a leaving group than a haHde ion. The high rate is most apparent with small primary alkyl groups, eg, methyl and ethyl. Some leaving groups, such as the fluorinated sulfonate anion, eg, the triflate anion, CF SO, react even faster in ester form (4). Against phenoxide anion, the reaction rate is methyl triflate [333-27-7] dimethyl sulfate methyl toluenesulfonate [23373-38-8] (5). Dialkyl sulfates, as compared to alkyl chlorides, lack chloride ions in their products chloride corrodes and requires the use of a gas instead of a Hquid. The lower sulfates are much less expensive than lower bromides or iodides, and they also alkylate quickly. 

Fluorination with Alkali Metal Fluorides, Sodium and potassium fluorides react with alkyl hydrogen sulfates and with acid chlorides to produce organic fluorides ... 

The Insertion of a fluorine atom is performed by electrophllicaHy treating an unactivated or deactivated position such as the vinylic with CF.)OF. A selective sulfation is effected in the order of alkyl over phenolic hydroxyl groups using dicyclohexylcarbodlimide and sulfuric acid in dimethylformamide ° Oxiranes are formed from carbonyl groups using methylene bromide and lithium or lithium amalgam. ... 

Keratin hydrolysates (->proteins) and - surfactants such as - fatty alcohol ether sulfates, - al-kylpolyglucosides and fluorinated surfactants (- perfluoro alkyl compounds) are used as basic protein foaming agents in the formulation of fire extinguishing foams. 

---