IP Library Granted Patent US 12,515,212
Granted Patent B2
US 12,515,212 · App. 18/371,808 · Granted Jan 6, 2026

Processes for purifying polyether polyols using ion exchange resins

Inventors: Daniel R. Wagner (Pittsburgh, PA); Brian L Neal (Pittsburgh, PA)
Assignee: Covestro LLC
B01J47/026B01D3/10B01J39/12B01J41/10C08G18/48
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,515,212
App. No.
18/371,808
Granted
Jan 6, 2026
Kind
B2
Abstract

Processes for purifying polyether polyols via treatment with ion exchange resins. A mixture that includes the polyether polyol and alkali metal ions is passed through a first bed that includes a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to remove alkali metal ions from the mixture. Thereafter, the product is passed through a second bed comprising an anion exchange resin comprising quaternary ammonium groups and a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to thereby produce a purified polyether polyol.

Claims (20)

1 . A process for removing alkali metal ions from a polyether polyol, comprising: (a) passing a mixture comprising the polyether polyol and the alkali metal ions through a first bed comprising a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to remove alkali metal ions from the mixture; and (b) passing the product of step (a) through a second bed comprising an anion exchange resin comprising quaternary ammonium groups and a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to thereby produce a purified polyether polyol, wherein the first bed and the second bed are each free of a cation exchange resin that comprises sulfonic acid groups.

2 . The process of claim 1 , wherein the polyether polyol has a hydroxyl number of no more than 56 mg KOH/gram, measured according to ASTM D4274-16.

3 . The process of claim 2 , wherein the polyether polyol has a hydroxyl number of 25 to 35 mg KOH/gram, measured according to ASTM D4274-16.

4 . The process of claim 1 , wherein the mixture comprising the polyether polyol and the alkali metal ions is combined with a mixture comprising water and a polar organic solvent prior to passing the mixture comprising the polyether polyol and the alkali metal ions through the first bed, wherein a relative weight ratio of polar organic solvent and water in the mixture comprising water and polar organic solvent is within a range of 1:1 to 10:1.

5 . The process of claim 4 , wherein the mixture comprising water and polar organic solvent is present in an amount of 10 to 40% by weight, based on the total combined weight of (i) the mixture comprising water and polar organic solvent and (ii) the mixture comprising the polyether polyol and the alkali metal ions.

6 . The process of claim 1 , wherein at least one of a container that includes the first bed and a container that includes the second bed is operated liquid-full throughout the process.

7 . The process of claim 6 , wherein the liquid level in the container operated liquid-full throughout the process is maintained at a level that is at least 95% of the total container height throughout the process.

8 . The process of claim 1 , wherein cation exchange resin that comprises sulfonic acid groups is present in an amount of no more than 1% by weight, based on the total weight of ion exchange resin used in each bed.

9 . The process of claim 1 , further comprising removing organic solvent and water from the purified polyether polyol.

10 . The process of claim 9 , wherein the removing organic solvent and water from the purified polyether polyol comprises at least atmospheric distillation and vacuum distillation.

11 . The process of claim 9 , wherein, after removal of organic solvent and water, the purified polyether polyol has a 2M2P (2-Methyl-2-Pentenal) content of no more than 5 ppm, based on total weight of the polyether polyol, as measured by Headspace Gas Chromatography and Mass Spectrometry (HS GC-MS).

12 . The process of claim 9 , wherein, after removal of organic solvent and water, the purified polyether polyol has a 2M2P (2-Methyl-2-Pentenal) content of no more than 1 ppm, based on total weight of the polyether polyol, as measured by Headspace Gas Chromatography and Mass Spectrometry (HS GC-MS).

13 . The process of claim 12 , wherein the purified polyether polyol has an acid number of no more than 0.1 mg KOH/g measured according to ASTM D7253-16.

14 . The process of claim 12 , wherein the purified polyether polyol has an alkalinity, determined by visual titration, of no more than 0.2 meq/kg.

15 . A process for producing a polyether polyol, comprising: (a) adding an alkylene oxide onto an H-functional starter in the presence of an alkali metal catalyst to produce an alkali metal-containing crude polyol comprising a mixture comprising the polyether polyol and alkali metal ions; (b) passing the mixture through a first bed comprising a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to remove alkali metal ions from the mixture; and (c) passing the product of step (b) through a second bed comprising an anion exchange resin comprising quaternary ammonium groups and a cation exchange resin comprising carboxylic acid and/or phosphonic acid groups to thereby produce a purified polyether polyol, wherein the first bed and the second bed are each free of a cation exchange resin that comprises sulfonic acid groups.

16 . The process of claim 13 , wherein the polyether polyol has a hydroxyl number of no more than 56 mg KOH/gram, measured according to ASTM D4274-16.

17 . The process of claim 15 , wherein cation exchange resin that comprises sulfonic acid groups is present in an amount of no more than 1% by weight, based on the total weight of ion exchange resin used in each bed.

18 . The process of claim 15 , further comprising removing organic solvent and water from the purified polyether polyol.

19 . The process of claim 18 , wherein, after removal of organic solvent and water, the purified polyether polyol has a 2M2P (2-Methyl-2-Pentenal) content of no more than 5 ppm, based on total weight of the polyether polyol, as measured by Headspace Gas Chromatography and Mass Spectrometry (HS GC-MS).

20 . The process of claim 18 , wherein, after removal of organic solvent and water, the purified polyether polyol has a 2M2P (2-Methyl-2-Pentenal) content of no more than 1 ppm, based on total weight of the polyether polyol, as measured by Headspace Gas Chromatography and Mass Spectrometry (HS GC-MS).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2023
From: WAGNER, DANIEL R.; NEAL, BRIAN L.
To: COVESTRO LLC
Reel/Frame 064998/0362 →
Continuity (2)
Provisional Application 63379175 · Oct 12, 2022
Related Publication 20240123438A1 · Apr 18, 2024
References Cited (28)
US 3458436A · Martinola et al. · 1969 [cited by applicant]
US 4985551A · Perry · 1991 [cited by examiner]
US 4994627A · Cuscurida et al. · 1991 [cited by applicant]
US 5254227A · Cawlfield et al. · 1993 [cited by applicant]
US 5342541A · Chavez et al. · 1994 [cited by applicant]
US 5410093A · Dorai · 1995 [cited by applicant]
US 5416241A · Ruszkay · 1995 [cited by applicant]
US 5468840A · Tsutsui et al. · 1995 [cited by applicant]
US 5516885A · Gorzynski et al. · 1996 [cited by applicant]
US 5962749A · Parsons et al. · 1999 [cited by applicant]
US 6037381A · Beer et al. · 2000 [cited by applicant]
US 6827858B2 · Bader et al. · 2004 [cited by applicant]
US 6878802B2 · Ciprian et al. · 2005 [cited by applicant]
US 9040753B2 · Chen · 2015 [cited by applicant]
US 9040754B2 · Osborne et al. · 2015 [cited by applicant]
US 9353039B2 · Den Heeten et al. · 2016 [cited by applicant]
US 10131743B2 · Lorenz et al. · 2018 [cited by applicant]
US 10544158B1 · Loveday et al. · 2020 [cited by applicant]
US 20010011147A1 · Krueger et al. · 2001 [cited by applicant]
US 20130274421A1 · Kim et al. · 2013 [cited by applicant]
US 20140018459A1 · Shutov et al. · 2014 [cited by applicant]
US 20150158976A1 · Dorai et al. · 2015 [cited by applicant]
US 20190106369A1 · Schubert et al. · 2019 [cited by applicant]
US 20210130544A1 · Wood et al. · 2021 [cited by applicant]
CN 102336902A · 2012 [cited by applicant]
Kirk-Othmer Encyclopedia of Chemical Technology; Fourth Edition; vol. 14;; Imaging Technology to Lanthanides; John Wiley & Sons; pp. 760-770; Ion Exchange. [cited by applicant]
De Lucas et al; Separation Science and Technology; 30(1); pp. 125-140, Copyright 1995 by Marcel Dekker, Inc. [cited by applicant]
Ionescu, Mihail; Chemistry and Technology of Polyols for Polyurethanes; Copyright 2005, Rapra Technology Limited, Shawbury, Shrewsbury, Shropshire, SY4, 4NR, UK; p. 132. [cited by applicant]