US 11,858,875 B2
Propenylamines and methods of making and using same
William M. Lamanna, Stillwater, MN (US); Michael J. Bulinski, Stillwater, MN (US); Sean M. Smith, Woodbury, MN (US); Alexandre R. Monteil, St. Paul, MN (US); Michael G. Costello, Afton, MN (US); and John G. Owens, Woodbury, MN (US)
Assigned to 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
Filed on Jul. 27, 2022, as Appl. No. 17/874,851.
Application 17/874,851 is a division of application No. 16/326,464, granted, now 11,479,525, previously published as PCT/US2017/047720, filed on Aug. 21, 2017.
Claims priority of provisional application 62/377,879, filed on Aug. 22, 2016.
Prior Publication US 2022/0380296 A1, Dec. 1, 2022
Int. Cl. C07C 209/68 (2006.01); C07D 295/067 (2006.01); C09K 5/10 (2006.01); H01M 8/04029 (2016.01); H01M 8/04701 (2016.01); H05K 7/20 (2006.01)
CPC C07C 209/68 (2013.01) [C07D 295/067 (2013.01); C09K 5/10 (2013.01); H01M 8/04029 (2013.01); H01M 8/04701 (2013.01); H05K 7/20218 (2013.01)] 3 Claims
 
1. A method of making a composition, the method comprising:
contacting a perfluorinated allylamine of general formula (2) with an active isomerization catalyst;

OG Complex Work Unit Chemistry
carrying out a selective catalytic isomerization to form a 1-propenylamine of general formula (1);

OG Complex Work Unit Chemistry
wherein each Rf1 and Rf2 comprises:
(i) independently a linear or branched perfluoroalkyl group having 1-8 carbon atoms and optionally comprises one or more catenated heteroatoms; or
(ii) bonded together to form a ring structure having 4-8 carbon atoms and that
optionally comprises one or more catenated heteroatoms, and
wherein the selectivity for formation of the E isomer of formula (1) is at least 60 wt. %, based on the total weight of the propenylamine in the composition.