Abstract: Methods of producing N,N-branched sulfamoyl fluoride compounds of the formula F-S(O)2-NR2 by contacting bismuth trifluoride with an N,N-branched sulfamoyl nonfluorohalide compound of the formula X-SO2NR2, wherein X=chlorine (Cl), bromine (Br), or iodine (I), and each R is, independently, a linear or branched alkyl, fluoroalkyl, alkenyl, fluoroalkenyl, alkynyl, or fluoroalkynyl with 1 to 12 carbon atoms, to fluorinate the N,N-branched sulfamoyl nonfluorohalide compound. This is a non-aqueous method, the purity of product is very high, and the desired product can be isolated in quantitative yield. The N,N-branched sulfamoyl fluoride compounds so produced are useful in various applications including as electrolyte solvents and additives in electrochemical devices, such as lithium batteries and capacitors, and in biological fields, among others.

Abstract: Processes for producing a N,N-dialkyl perfluoroalkyl-sulfonamide product of the formula Rf—S(O)2—NRaRb (I) in which Rf represents fully or partially fluorinated alkyl groups with carbon 1 to 12 and Ra and Rb represents linear or branched or cyclic alkyl, alkene or alkyne groups with carbon 1 to 12, wherein Ra=Rb or Ra?Rb. In some embodiments, a reaction proceeds by contacting a perfluoroalkylsulfonyl halide of the formula: X—S(O)2—Rf, (II), in which X represents F, Cl, Br or I, with dialkylamine of the formula HNRaRb, under conditions sufficient to produce the desired N,N-dialkyl perfluoroalkylsulfonamide product of Formula I. In some embodiments, the reaction is carried out using a solvent of Formula I.

Abstract: Processes for producing a N,N-dialkyl perfluoroalkyl-sulfonamide product of the formula Rf—S(O)2—NRaRb (I) in which Rf represents fully or partially fluorinated alkyl groups with carbon 1 to 12 and Ra and Rb represents linear or branched or cyclic alkyl, alkene or alkyne groups with carbon 1 to 12, wherein Ra=Rb or Ra?Rb. In some embodiments, a reaction proceeds by contacting a perfluoroalkylsulfonyl halide of the formula: X—S(O)2—Rf, (II), in which X represents F, Cl, Br or I, with dialkylamine of the formula HNRaRb, under conditions sufficient to produce the desired N,N-dialkyl perfluoroalkylsulfonamide product of Formula I. In some embodiments, the reaction is carried out using a solvent of Formula I.

Abstract: Methods for making high-purity LiFSI salts and intermediate products using one, the other, or both of a reactive-solvent removal/replacement method and an LiFSI purification method. In some embodiments, the reactive-solvent removal/replacement method includes using non-reactive anhydrous organic solvents to remove and/or replace one or more reactive solvents in a crude LiFSI. In some embodiments, the LiFSI purification method includes using anhydrous organic solvents to remove impurities, such as synthesis impurities, from a crude LiFSI. In some embodiments, crude LiFSI can be made using an aqueous-based neutralization process. LiFSI salts and products made using methods of the disclosure are also described, as are uses of such salts and products and electrochemical devices that include such salts and products.

Abstract: Methods for making high-purity LiFSI salts and intermediate products using one, the other, or both of a reactive-solvent removal/replacement method and an LiFSI purification method. In some embodiments, the reactive-solvent removal/replacement method includes using non-reactive anhydrous organic solvents to remove and/or replace one or more reactive solvents in a crude LiFSI. In some embodiments, the LiFSI purification method includes using anhydrous organic solvents to remove impurities, such as synthesis impurities, from a crude LiFSI. In some embodiments, crude LiFSI can be made using an aqueous-based neutralization process. LiFSI salts and products made using methods of the disclosure are also described, as are uses of such salts and products and electrochemical devices that include such salts and products.

Abstract: Methods of removing target impurities from a crude lithium bis(fluorosulfonyl)imide (LiFSI) to make a purified LiFSI product. In some embodiments, a purification method includes contacting crude LiFSI with a first anhydrous organic solvent to create a solution containing LiFSI and the target impurity(ies), wherein the LiFSI is soluble and the impurity(ies) is/are substantially insoluble. In some embodiments, a second anhydrous organic solvent is added to the solution to precipitate the target impurity(ies), which is then filtered to obtain a filtrate. In some embodiments, solvent is removed from the filtrate to obtain a solid mass containing LiFSI, which may then be contacted with a third anhydrous organic solvent in which the LiFSI is insoluble. The LiFSI may then be isolated from the third anhydrous organic solvent to obtain the purified LiFSI product. Also disclosed are purified LiFSI products and electrochemical devices utilizing purified LiFSI products, among other things.

Abstract: Free-solvent-free lithium sulfonimide salt compositions that are liquid at room temperature, and methods of making free-solvent-free liquid lithium sulfonimide salt compositions. In an embodiment, the methods include mixing one or more lithium sulfonimide salts with one or more ether-based solvents and then removing the free solvent(s) under suitable vacuum, temperature, and time conditions so as to obtain a free-solvent-free liquid lithium sulfonimide salt composition that is liquid at room temperature. In an embodiment, the only solvent molecules that remain in the liquid lithium sulfonimide salt composition are adducted with lithium sulfonimide salt molecules. An example automated processing system for making free-solvent-free liquid lithium sulfonimide salts is also disclosed.

Abstract: Free-solvent-free lithium sulfonimide salt compositions that are liquid at room temperature, and methods of making free-solvent-free liquid lithium sulfonimide salt compositions. In an embodiment, the methods include mixing one or more lithium sulfonimide salts with one or more ether-based solvents and then removing the free solvent(s) under suitable vacuum, temperature, and time conditions so as to obtain a free-solvent-free liquid lithium sulfonimide salt composition that is liquid at room temperature. In an embodiment, the only solvent molecules that remain in the liquid lithium sulfonimide salt composition are adducted with lithium sulfonimide salt molecules. An example automated processing system for making free-solvent-free liquid lithium sulfonimide salts is also disclosed.

Abstract: The present invention provides a single-phase or homogeneous solution comprising a high concentration of a salt, in particular a lithium salt, in an organic solvent. Such a high salt content in organic solvent is useful in a variety of applications including, but not limited to, in electrical energy storage devices as well as other devices that can benefit from a low-volatility liquid electrolyte.

Abstract: A method of removing one or more target impurities from crude hydrogen bis(fluorosulfonyl)imide (HFSI) using a crystallization technique. In some embodiments, the method includes contacting the crude HFSI with at least one anhydrous solvent to create a solution. The solution is caused to have a temperature sufficient to cause HFSI in the solution to crystalize while the one or more impurities remain dissolved in the mother liquor of the solution. The crystalized HFSI and the mother liquor containing the one or more impurities are separated to obtained a purified HFSI product. Purified HFSI products are also disclosed, as are systems, such as secondary batteries, incorporating purified HFSI products.

Abstract: Methods for making high-purity LiFSI salts and intermediate products using one, the other, or both of a reactive-solvent removal/replacement method and an LiFSI purification method. In some embodiments, the reactive-solvent removal/replacement method includes using non-reactive anhydrous organic solvents to remove and/or replace one or more reactive solvents in a crude LiFSI. In some embodiments, the LiFSI purification method includes using anhydrous organic solvents to remove impurities, such as synthesis impurities, from a crude LiFSI. In some embodiments, crude LiFSI can be made using an aqueous-based neutralization process. LiFSI salts and products made using methods of the disclosure are also described, as are uses of such salts and products and electrochemical devices that include such salts and products.

Abstract: Methods of removing target impurities from a crude lithium bis(fluorosulfonyl)imide (LiFSI) to make a purified LiFSI product. In some embodiments, a purification method includes contacting crude LiFSI with a first anhydrous organic solvent to create a solution containing LiFSI and the target impurity(ies), wherein the LiFSI is soluble and the impurity(ies) is/are substantially insoluble. In some embodiments, a second anhydrous organic solvent is added to the solution to precipitate the target impurity(ies), which is then filtered to obtain a filtrate. In some embodiments, solvent is removed from the filtrate to obtain a solid mass containing LiFSI, which may then be contacted with a third anhydrous organic solvent in which the LiFSI is insoluble. The LiFSI may then be isolated from the third anhydrous organic solvent to obtain the purified LiFSI product. Also disclosed are purified LiFSI products and electrochemical devices utilizing purified LiFSI products, among other things.

Abstract: Binary and ternary eutectic mixtures and corresponding electrolytes are disclosed. In some embodiments, binary eutectic mixtures and electrolytes each include a first salt, X1+Y1?, and a second salt, X2+Y2?, wherein each of X1+ and X2+ is an alkali metal cation and X1+ is different from X2+; and each of Y1? and Y2? is a sulfonimide anion and Y1? is different from Y2?. In ternary eutectic mixtures and electrolytes further include a third salt, X3+Y3?, wherein X3+ is different from each of X1+ and X2+. In some embodiments, the eutectic mixtures and electrolytes have melting points in a range of about 5° C. to about 70° C. Electrochemical devices containing such eutectic-mixture electrolytes are also disclosed.

Abstract: The present invention provides methods and processes for producing ?-fluoroalkyl ketones from non-fluoro ?-haloalkyl ketones using a fluorohydrogenate compound. In some embodiments, the fluorohydrogenate compound is an ionic liquid. One particular method of the invention utilizes a fluorohydrogenate ionic liquid compound of the formula: Q+[F.(HF)n], wherein Q30 is an onium cation and n is a number from 0 to 3.

Abstract: The present invention provides N-substituted glycinium bis(fluorosulfonyl)imide compounds and methods for producing and using the same. In particular, the N-substituted glycinium bis(fluorosulfonyl)imide compound is of the formula: wherein each of R1, R2 and R3 is independently selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, (heteroaryl)alkyl, heterocyclyl, and (heterocyclyl)alkyl; or R1 and R2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl, or a nitrogen-heteroaryl.

Abstract: The present invention provides an N-substituted glycinium (fluorosulfonyl)(trifluoromethylsulfonyl)imide compounds and methods for producing and using the same. In particular, the N-substituted glycinium (fluorosulfonyl)(trifluoromethylsulfonyl)imide compound is of the formula: wherein each of R1, R2 and R3 is independently selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, (heteroaryl)alkyl, heterocyclyl, and (heterocyclyl)alkyl; or R1 and R2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl, or a nitrogen-heteroaryl.

Abstract: The present invention provides a single-phase or homogeneous solution comprising a high concentration of a salt, in particular a lithium salt, in an organic solvent. Such a high salt content in organic solvent is useful in a variety of applications including, but not limited to, in electrical energy storage devices as well as other devices that can benefit from a low-volatility liquid electrolyte.

Abstract: The invention provides a method for producing fluorotrifluoromethylsulfonyl imide (FTFSI) by reacting non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) with hydrogen fluoride, where each X is independently a nonfluoro-halide, such as Cl, Br, or I.

Abstract: The present invention provides a method for producing ionic liquids without the use of a volatile solvent and/or water. In some embodiments, methods of the invention allow a continuous process for producing ionic liquids.

Abstract: The present invention provides methods and processes for producing ?-fluoroalkyl ketones from non-fluoro ?-haloalkyl ketones using a fluorohydrogenate compound. In some embodiments, the fluorohydrogenate compound is an ionic liquid. One particular method of the invention utilizes a fluorohydrogenate ionic liquid compound of the formula: Q+[F•(HF)n], wherein Q is an onium cation and n is a number from 0 to 3.