Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides
First Claim
1. A process for the preparation of a bis(fluoroalkylsulfonyl)imide salt comprising the step of reacting at least two equivalents of a fluoroalkylsulfonyl halide (wherein the fluoroalkyl is substantially fluorinated) with one equivalent of ammonia and at least three equivalents of a non-nucleophilic base at a temperature and for a time sufficient to yield the imide salt, provided that if the fluoroalkylsulfonyl halide is a perfluoroalkylsulfonyl halide, the alkyl group has at least 2 carbon atoms.
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Abstract
A method for preparing fluoroalkylsulfonyl imides by reacting a fluoroalkylsulfonamide with a fluoroalkylsulfonyl halide or a fluorosulfonyl halide in the presence of a non-nucleophilic base. One reaction is:
Z--R.sub.f --SO.sub.2 NH.sub.2 +Z--R'"'"'.sub.f --SO.sub.2 --X+2B(Z--R.sub.f
--SO2)(Z--R'"'"'f --SO2)N-.BH+ +BHX,
where each Z is a fluorine atom or a polymerizable organic functional group, Rf and R'"'"'f are fluoroalkylene groups optionally containing catenary oxygen or nitrogen, X is a halogen atom, and B is a non-nucleophilic base.
Unsymmetrical imides and polymeric imides can be prepared.
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Citations
8 Claims
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1. A process for the preparation of a bis(fluoroalkylsulfonyl)imide salt comprising the step of reacting at least two equivalents of a fluoroalkylsulfonyl halide (wherein the fluoroalkyl is substantially fluorinated) with one equivalent of ammonia and at least three equivalents of a non-nucleophilic base at a temperature and for a time sufficient to yield the imide salt, provided that if the fluoroalkylsulfonyl halide is a perfluoroalkylsulfonyl halide, the alkyl group has at least 2 carbon atoms.
- View Dependent Claims (2, 3, 4)
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4. The process of claim 3 further comprising contacting the bis(fluoroalkylsulfonyl)imide salt with an inorganic base having an alkali metal cation M+, volatilizing the non-nucleophilic base B, and isolating the resulting bis(fluoroalkylsulfonyl)imide salt of the formula (Z--Rf SO2)2 N-.M+ by filtration, evaporating volatile components from the residue, followed by solvent extraction of the filtrate and removal of the solvent.
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5. A process for preparing a bis(fluoroalkylsulfonyl)imide which comprises contacting a sulfonamidofluoroalkylenesulfonyl halide of the formula X--SO2 --Rf --SO2 NH2 with a non-nucleophilic base at a temperature and for a time sufficient to produce a polymeric fluoroalkylsulfonimide having the repeat unit .paren open-st.SO2 --Rf --SO2 N- .paren close-st.n, wherein n is an integer greater than 1 and X is a halogen atom.
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6. A process for preparing a polymeric fluoroalkylsulfonimide comprising a reaction step characterized by the reaction scheme:
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space="preserve" listing-type="equation">H.sub.2 NSO.sub.2 --R.sub.f --SO.sub.2 NH.sub.2 +X--SO.sub.2 --R'"'"'.sub.f --SO.sub.2 --X+4B.paren open-st.SO.sub.2 --R.sub.f --SO.sub.2 N.sup.- --SO.sub.2 --R'"'"'.sub.f N.sup.-).sub.n 2BH.sup.+ +2B.HX,wherein n is an integer greater than 1 and X is a halogen atom.
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7. A process for preparing a polymeric fluoroalkylsulfonimide comprising a reaction step characterized by the reaction scheme:
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space="preserve" listing-type="equation">X--SO.sub.2 --R.sub.f --SO.sub.2 --X+NH.sub.3 +3B.paren open-st.SO.sub.2 --R.sub.f --SO.sub.2 --N.sup.- .paren close-st..sub.n +2B.HX,wherein n is an integer greater than 1, Rf is a fluoroalkylene group, B is a non-nucleophilic base and X is a halogen atom. - View Dependent Claims (8)
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Specification