US 12,110,267 B2
Methods for vicinal diol separation
Dennis J. Miller, Okemos, MI (US); Carl T. Lira, East Lansing, MI (US); Lars Peereboom, Haslett, MI (US); Scott F. Parker, Fowlerville, MI (US); Thomas D. Dionise, Lansing, MI (US); and William G. Killian, East Lansing, MI (US)
Assigned to BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY, East Lansing, MI (US)
Appl. No. 17/283,090
Filed by BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY, East Lansing, MI (US)
PCT Filed Oct. 7, 2019, PCT No. PCT/US2019/054998
§ 371(c)(1), (2) Date Apr. 6, 2021,
PCT Pub. No. WO2020/076699, PCT Pub. Date Apr. 16, 2020.
Claims priority of provisional application 62/742,642, filed on Oct. 8, 2018.
Prior Publication US 2021/0340088 A1, Nov. 4, 2021
Int. Cl. C07C 29/92 (2006.01); B01J 19/00 (2006.01); B01J 19/18 (2006.01); C07C 29/09 (2006.01); C07C 29/88 (2006.01); C07C 31/20 (2006.01)
CPC C07C 29/92 (2013.01) [B01J 19/0066 (2013.01); B01J 19/1862 (2013.01); C07C 29/095 (2013.01); C07C 29/88 (2013.01); C07C 31/202 (2013.01); C07C 31/205 (2013.01); C07C 31/207 (2013.01)] 23 Claims
OG exemplary drawing
 
1. A method for separating polyols, the method comprising:
feeding to a reactor:
(i) a first polyol reactant having 2 to 10 carbon atoms and comprising at least two hydroxyl groups on adjacent carbon atoms,
(ii) a second polyol reactant different from the first polyol reactant, having 2 to 10 carbon atoms, and comprising at least two hydroxyl groups on adjacent carbon atoms,
(iii) an acetalization reactant comprising at least one of an aldehyde having 1 to 10 carbon atoms and a ketone having 3 to 10 carbon atoms,
(iv) a first acetalization product comprising a reaction product between the first polyol reactant and the acetalization reactant, and
(v) optionally water;
forming in the reactor via an acid-catalyzed reaction:
(i) optionally further first acetalization product comprising a reaction product between the first polyol reactant and the acetalization reactant,
(ii) a second acetalization product comprising a reaction product between the second polyol reactant and the acetalization reactant, and
(iii) water;
separating a reactor product mixture comprising the first acetalization product, the second acetalization product, the first polyol reactant, and the water into (i) a water-immiscible product comprising the first acetalization product and the second acetalization product, and (ii) an aqueous product comprising the first polyol reactant and the water;
separating the water-immiscible product into (i) a first product comprising the first acetalization product, and (ii) a second product comprising the second acetalization product; and
hydrolyzing the second product to form the second polyol reactant from the second acetalization product.