Multifunctional sulfone/fluorinated ester solvents
View Patent ↗Novel multifunctional sulfone/fluorinated ester compounds are described. These compounds may be useful as non-aqueous electrolyte solvents, specialty solvents, and starting materials and intermediates for synthesis of dyes, agricultural chemicals, and pharmaceuticals.
1. A process for forming a product compound as represented by the structure of the following formula
wherein R 1 is C 1 to C 4 fluoroalkyl; R 2 is C 1 to C 6 alkylene radical, optionally substituted with one or more ether oxygens; and R 3 is C 1 to C 6 alkyl, optionally substituted with one or more ether oxygens,
comprising the step of: combining, optionally in a solvent,
a)
wherein R 1 , R 2 and R 3 are as set forth above.
2. The process according to claim 1 wherein each R 1 is CF 3 , R 2 is CH 2 CH 2 , and R 3 is CH 3 .
3. The process according to claim 1 wherein each R 1 is CF 2 H, R 2 is CH 2 CH 2 , and R 3 is CH 3 .
4. The process according to claim 1 wherein the optional solvent is selected from the group consisting of dichloromethane, chloroform, ether, and tetrahydrofuran.
5. The process according to claim 1 further comprising admixing the product with an electrolyte salt, and optionally with a solvent component, to form an electrolyte composition.
6. The process according to claim 5 further comprising incorporating the electrolyte composition formed thereby into an electrochemical cell.
7. A composition comprising:
(a) a compound represented by the structure of the following formula:
wherein R 1 is C 1 to C 4 fluoroalkyl; R 2 is C 1 to C 6 alkylene radical, optionally substituted with one or more ether oxygens; and R 3 is C 1 to C 6 alkyl, optionally substituted with one or more ether oxygens; and
(b) at least one electrolyte salt.
8. The composition according to claim 7 further comprising at least one solvent component selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, ethylene carbonate, propylene carbonate, vinylethylene carbonate, fluoroethylene carbonate, 2,2,2-trifluoroethyl carbonate, and methyl 2,2,3,3-tetrafluoropropyl carbonate.
9. The composition according to claim 1 wherein the electrolyte salt is selected from the group consisting of lithium hexafluorophosphate, lithium bis(trifluoromethanesulfonyl)imide, lithium bis(perfluoroethanesulfonyl)imide, lithium tetrafluoroborate, lithium perchlorate, lithium hexafluoroarsenate, lithium trifluoromethanesulfonate, lithium tris(trifluoromethanesulfonyl)methide, lithium bis(oxalato)borate, Li 2 B 12 F 12-x H x where x is equal to 0 to 8, and mixtures of lithium fluoride and B(OC 6 F 5 ) 3 .
10. The composition according to claim 9 wherein the electrolyte salt is lithium hexafluorophosphate.
11. The composition according to claim 7 wherein R 1 is CF 3 , R 2 is CH 2 CH 2 , and R 3 is CH 3 .
12. The composition according to claim 7 wherein R 1 is CF 2 H, R 2 is CH 2 CH 2 , and R 3 is CH 3 .
13. An electrochemical cell comprising:
(a) a housing;
(b) an anode and a cathode disposed in said housing and in ionically conductive contact with one another;
(c) an electrolyte composition disposed in said housing and providing an ionically conductive pathway between said anode and said cathode, wherein the electrolyte composition comprises a composition represented by the structure:
and at least one electrolyte salt, wherein R 1 is C 1 to C 4 fluoroalkyl; R 2 is C 1 to C 6 alkylene radical, optionally substituted with one or more ether oxygens; and R 3 is C 1 to C 6 alkyl, optionally substituted with one or more ether oxygens; and
(d) a porous separator between said anode and said cathode.
14. The electrochemical cell according to claim 13 wherein R 1 is CF 3 , R 2 is CH 2 CH 2 , and R 3 is CH 3 .
15. The electrochemical cell according to claim 13 wherein R 1 is CF 2 H, R 2 is CH 2 CH 2 , and R 3 is CH 3 .
16. The electrochemical cell according to claim 13 wherein said electrochemical cell is a lithium ion battery.
17. An article comprising the electrochemical cell according to claim 13 .