US 9,809,529 B2
Process for producing low VOC coalescing aids
George J. Frycek, Midland, MI (US); Felipe A. Donate, Midland, MI (US); Edward D. Daugs, Midland, MI (US); Rebecca J. Wachowicz, Bay City, MI (US); and Jason L. Trumble, Bay City, MI (US)
Assigned to DOW GLOBAL TECHNOLOGIES LLC, Midland, MI (US)
Appl. No. 15/318,032
Filed by Dow Global Technologies LLC, Midland, MI (US)
PCT Filed Jun. 18, 2015, PCT No. PCT/US2015/036387
§ 371(c)(1), (2) Date Dec. 12, 2016,
PCT Pub. No. WO2015/200087, PCT Pub. Date Dec. 30, 2015.
Claims priority of provisional application 62/016,301, filed on Jun. 24, 2014.
Prior Publication US 2017/0129843 A1, May 11, 2017
Int. Cl. C07C 69/76 (2006.01); C07C 67/08 (2006.01); C07C 67/54 (2006.01)
CPC C07C 67/08 (2013.01) [C07C 67/54 (2013.01)] 13 Claims
 
1. A process for the preparation of a glycol ether ester, the process comprising (a) contacting in a reaction zone benzoic acid and/or benzoic acid anhydride with a glycol ether feed and a catalytic amount of phosphoric acid, to form a reaction mixture, under reaction conditions sufficient to produce a glycol ether ester product and water, wherein the feed comprises a glycol ether and butanal, and wherein the water and butanal are at least partially vaporized in the reaction zone and are passed to a separation zone providing a first crude product and having a butanal content of less than 5 ppm, and wherein the process is operated under conditions of temperature and pressure wherein the maximum temperature in the separation zone in step (a) is less than the boiling point of the reaction mixture.