Process for preparation of hydrofluoroalkenes by selective catalytic consecutive hydrodefluorination
AssigneeUniversity of Ottawa
InventorsRalph Thomas BAKER, Nicholas Orlando ANDRELLA
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Abstract
The present application provides a hydrodefluorination process for the preparation of hydrofluoroalkenes by catalyzed substitution of one or more F atoms of a C2-C30 fluoroalkene, or a C2-C10 fluoroalkene, with one or more H atoms using a hydride source, such as a silane, and copper catalyst. During this process at least one C—F bond in the fluoroakene is converted to a C—H bond. The process is useful in the manufacture of hydrofluoroalkenes, such as hydrofluoroalkenes employed as, for example, refrigerants and blowers. Also provided are precatalyst compositions for performing the process, and formulations manufactured from hydrofluoroalkenes produced using the process.
Claims20
A process for hydrodehalogenation of a fluoroalkene comprising treating a fluoroalkene with a hydride source and a catalyst of Formula VIII
- LxMyHz VIII
- where each L is, independently, a monodentate, bidentate, tridentate, or tetradentate phosphorous, nitrogen, oxygen, sulfur or carbon-based ligand or combination thereof, of the general formula PR3, NR3, SR2, OR2, :CR2 where each R is independently;
- H, alkyl, aryl, silyl, alkoxy, amino, or halogen;
- M is a metal;
- and
- x is an integer from 1 to 4;
- y is 1;
- z is an integer from 1 to 4;
- and
- the sum of z+x is less than or equal to 4.
A compound of Formula IX
- where each of R4, R5 and R6 are each independently H, halogen, alkyl, alcohol, OR′, NR′3, SH, SR′, fluorothioether, silyl, ═CR′2, —C(R′)═CR′, —C≡CR′, phenyl, —C(O)R′, —C(O)H, —OC(O)OR′, —C(O)OR′, —C≡N, —N≡C, —NO2, —O5H4N, —S(O)R′, —S(O)2R′, —SC≡N, —B(OR′)2, and their fluorovariants respectively, where R′ is an alkyl or alkenyl group;
- L is a monodentate, bidentate, tridentate, or tetradentate phosphorous, nitrogen, oxygen, sulfur or carbon-based ligand or combination thereof, of the general formula PR3, NR3, SR2, OR2, :CR2 (carbene) where each R is independently H, alkyl, aryl, silyl, alkoxy, amino, or halogen;
- and
- x is an integer from 1 to 4.
Dependencies are inferred from the claim text.