Fluorinated cyclic carbonates and compositions thereof
View Patent ↗Novel fluorinated cyclic carbonate 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 compound as represented by the following structure:
wherein R is a C 1 to C 4 fluoroalkyl group.
2. A compound according to claim 1 wherein R is CF 3 .
3. A compound according to claim 1 wherein R is CF 2 H.
4. A process for preparing a compound according to claim 1 comprising the step of combining, optionally in a solvent, glycerol 1,2-carbonate and (RfCO) 2 O or RfCOX, wherein Rf is a C 1 to C 4 fluoroalkyl and X is a halogen.
5. A process according to claim 4 wherein (RfCO) 2 O is (CF 3 CO) 2 O.
6. A process according to claim 4 wherein (RfCO) 2 O is (CF 2 HCO) 2 O.
7. A process according to claim 4 wherein the solvent is selected from the group consisting of dichloromethane, chloroform, ether and tetrahydrofuran.
8. A composition comprising a compound according to claim 1 in admixture with at least one electrolyte salt.
9. A composition according to claim 8 further comprising at least one co-solvent 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.
10. A composition according to claim 8 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 .
11. A composition according to claim 10 wherein the electrolyte salt is lithium hexafluorophosphate.
12. A composition according to claim 8 wherein R is CF 3 .
13. A composition according to claim 8 wherein R is CF 2 H.
14. An electrochemical cell comprising (a) a housing; (b) an anode and a cathode disposed within the housing; (c) a porous separator disposed within the housing between the anode and the cathode; and (d) an electrolyte composition disposed within the housing in contact with the anode, the cathode and the porous separator and providing an ionically-conductive pathway between the anode and the cathode, wherein the electrolyte composition includes at least one electrolyte salt and a compound according to claim 1 .
15. An electrochemical cell according to claim 14 wherein R is CF 3 .
16. An electrochemical cell according to claim 14 wherein R is CF 2 H.
17. An electrochemical cell according to claim 14 which is a lithium ion battery.
18. An article comprising an electrochemical cell according to claim 17 .