US 11,708,345 B2
Continuous method for preparing carbonate esters
Trevor L. Dzwiniel, Carol Stream, IL (US); and Krzysztof Pupek, Plainfield, IL (US)
Assigned to UCHICAGO ARGONNE, LLC, Chicago, IL (US)
Filed by UCHICAGO ARGONNE, LLC, Chicago, IL (US)
Filed on Mar. 23, 2021, as Appl. No. 17/209,742.
Application 17/209,742 is a continuation of application No. 16/812,628, filed on Mar. 9, 2020, granted, now 11,028,065.
Prior Publication US 2021/0276969 A1, Sep. 9, 2021
Int. Cl. C07D 317/40 (2006.01); B01J 31/02 (2006.01); C07C 69/96 (2006.01)
CPC C07D 317/40 (2013.01) [B01J 31/0232 (2013.01); C07C 69/96 (2013.01)] 16 Claims
OG exemplary drawing
 
1. A continuous process for preparing organic carbonate solvent of Formula (I):

OG Complex Work Unit Chemistry
comprising the steps of:
(a) contacting a first reactant with a reactive carbonyl source in reaction stream containing a catalyst flowing through a continuous flow reactor at a temperature in the range of about 20° C. to about 160° C., and at a flow rate providing a residence time in the range of about 0.1 minute to about 24 hours;
(b) optionally quenching any remaining reactive carbonyl source;
(c) collecting a reactor effluent exiting from the continuous flow reactor;
(d) recovering a crude product from the reactor effluent; and
(e) purifying the crude product to obtain the organic carbonate compound of Formula (I);
wherein:
the reactive carbonyl source is carbon dioxide; and the first reactant is an epoxide of Formula (III):

OG Complex Work Unit Chemistry
the catalyst comprises at least one material selected from the group consisting of a bicyclic amidine, an acid addition salt of a phosphazene, an acid addition salt of a bicyclic guanidine, a quaternary ammonium halide, and a quaternary phosphonium halide; and the catalyst is present in the reaction stream at a concentration of about 1 to 20 mol % relative to the epoxide;
Z is a covalent bond;
x is 1;
R and R1 are the same and are C1 to C4 fluoroalkyl comprising at least one fluoro substituent;
R2 is H;
R3 and R4 both are CH and are directly connected by the covalent bond Z.