US 11,685,707 B2
Method for making a di(aminoaryl)fluorene compound
Jonathan E. Meegan, Chester (GB); Victor Maruani, Lyons (FR); Vincent Schanen, Lyons (FR); and Paul Cross, York (GB)
Appl. No. 17/415,378
Filed by Cytec Industries Inc., Princeton, NJ (US)
PCT Filed Dec. 20, 2019, PCT No. PCT/US2019/067775
§ 371(c)(1), (2) Date Jun. 17, 2021,
PCT Pub. No. WO2020/132406, PCT Pub. Date Jun. 25, 2020.
Claims priority of provisional application 62/782,711, filed on Dec. 20, 2018.
Prior Publication US 2022/0064099 A1, Mar. 3, 2022
Int. Cl. C07C 209/84 (2006.01)
CPC C07C 209/84 (2013.01) 21 Claims
 
1. A method for making a di(aminoaryl)fluorene compound, comprising:
(a) reacting a fluorenone compound according structure (1):

OG Complex Work Unit Chemistry
with excess aminobenzene according to structure (II):

OG Complex Work Unit Chemistry
wherein:
each R1, R2, R3, R4, R12, and R13 is independently a group that is inert in the polymerization of epoxy compounds, and
R11 is H or (C1-C6)alkyl,
in the presence of an acid catalyst, in a liquid medium comprising ortho-dichlorobenzene and from which the di(aminoaryl)fluorene compound is crystallizable, to form a crude product mixture comprising the di(aminoaryl)fluorene compound, wherein the acid catalyst is soluble in the liquid medium and is selected from the group consisting of: (i) Lewis acids having an affinity for oxygen, and (ii) Brønsted acids,
(b) crystallizing di(aminoaryl)fluorene compound in the crude product mixture, and
(c) separating the product mixture into crystallized di(aminoaryl)fluorene compound and a filtrate.