US 12,441,673 B2
Catalysed synthesis of fluorinated alkenes and fluorinated alkene compositions
Viacheslav A. Petrov, Hockessin, DE (US); Jason R. Juhasz, Hockessin, DE (US); Luke David Simoni, Wilmington, DE (US); Drew Richard Brandt, West Chester, PA (US); and Jonathan P Stehman, Wilmington, DE (US)
Assigned to THE CHEMOURS COMPANY FC, LLC, Wilmington, DE (US)
Appl. No. 17/774,278
Filed by THE CHEMOURS COMPANY FC, LLC, Wilmington, DE (US)
PCT Filed Dec. 9, 2020, PCT No. PCT/US2020/063932
§ 371(c)(1), (2) Date May 4, 2022,
PCT Pub. No. WO2021/119078, PCT Pub. Date Jun. 17, 2021.
Claims priority of provisional application 62/945,388, filed on Dec. 9, 2019.
Prior Publication US 2022/0388929 A1, Dec. 8, 2022
Int. Cl. C07C 17/278 (2006.01); C09K 5/10 (2006.01); H01M 10/613 (2014.01); H01M 10/6567 (2014.01); H05K 7/20 (2006.01)
CPC C07C 17/278 (2013.01) [C09K 5/10 (2013.01); H01M 10/613 (2015.04); H01M 10/6567 (2015.04); H05K 7/203 (2013.01)] 15 Claims
OG exemplary drawing
 
1. A method of producing a fluoroolefin comprising: contacting a compound comprising formula (1),
RfCX1═CHCF3  (1)
wherein Rf is a linear or branched C1-C10 perfluorinated or polyfluorinated alkyl group; and wherein X1 is H, Br, Cl, or F; wherein the compound of formula (1) comprises at least one member selected from the group consisting of C4F9CH═CHCF3, (CF3)2CFCH═CHCF3, CF3CH═CFCF3, and CF3CH═CCICF3; with a fluorinated ethylene compound comprising formula (2),
CX2X3═CX4X5  (2)
wherein X2, X3, X4, and X5 are each independently H, Br, Cl, or F; and wherein at least three of X2, X3, X4, and X5 are F; wherein the fluorinated ethylene of formula (2) comprises at least one of CFCl═CF2; CFCl═CFCl, CFH═CF2 (HFO-1123), CFH═CFH (HFO-1132, and CF2=CH2(VF2); in the presence of a catalyst in an amount sufficient to form a composition comprising a compound of formula (3),
Rf(CF2)nCX6═CH(CF2)mCX7X8CFX9X10  (3)
wherein n is an integer from 0 to 10; wherein m is an integer from 1 to 10; wherein X6, X7, X8, X9, and X10 are each independently H, Cl, or F; and wherein the total number of each of H, Cl, and F represented by X6, X7, X8, X9, and X10 is the same as the total number of each of H, Cl, and F provided by X1, X2, X3, X4, and X5 in formulae (1) and (2), wherein the compound of formula (3) comprises at least one member selected from the group consisting of C4F9CH═CHCF2CFClCF3, C4F9CH═CHCF2CF2CF2Cl, (CF3)2CFCH═CHCF2CFClCF3, (CF3)2CFCH═CHCF2CF2CF2Cl, C2F5CH═CHC2F5, C2F5CF═CHCFClCF3, C2F5CF═CHCF2CF2Cl, C3F7CH═CClCF3 and C3F7CH═CClCF3.