IP Library Granted Patent US 8,354,561
Granted Patent B2
US 8,354,561 · App. 12/928,909 · Granted Jan 15, 2013

Trimethylolpropane color improvement

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 8,354,561
App. No.
12/928,909
Granted
Jan 15, 2013
Kind
B2
Abstract

The present invention provides a process for improving the color of trimethylolpropane which comprises the steps of a) supplying a crude, aqueous base solution of trimethylolpropane, containing color causing impurities, and having a pH of less than about 9; b) contacting said base solution with an alkaline material for a period of time sufficient to increase the pH of said base solution to greater than 11 and at a sufficient temperature to allow the color causing impurities to react with said alkaline material; c) cooling the resulting solution from step (b) for a sufficient period of time; d) contacting said base solution of step (c) with an organic acid for a sufficient period of time to lower the pH thereof to less than about 9.5; e) extracting the trimethylolpropane from said base solution of step (d) with an organic solvent; f) separating the trimethylolpropane from said organic solvent; and g) purifying said trimethylolpropane from step f) to form a trimethylolpropane having a phthalic color of less than 0.20 and an acid wash color of less than 8.

Claims (15)

1. A process for improving the color of trimethylolpropane which comprises the steps of:

a) supplying a crude, aqueous base solution of trimethylolpropane, containing color causing impurities, and having a pH of less than about 9;

b) contacting said base solution with an alkaline material for a period of time sufficient to increase the pH of said base solution to greater than 11 and at a sufficient temperature to allow the color causing impurities to react with said alkaline material;

c) cooling the resulting solution from step (b) for a sufficient period of time;

d) contacting said base solution of step (c) with an organic acid for a sufficient period of time to lower the pH thereof to less than about 9.5;

e) extracting the trimethylolpropane from said base solution of step (d) with an organic solvent;

f) separating the trimethylolpropane from said organic solvent; and

g) purifying said trimethylolpropane from step (f) to form a trimethylolpropane having a phthalic color of less than 0.20 and an acid wash color of less than 8.

2. The process as set forth in claim 1 , wherein the alkaline material is selected from the group consisting of alkali metal hydroxides, alkaline earth hydroxides, and mixtures thereof.

3. The process as set forth in claim 2 , wherein the alkaline material is potassium or sodium hydroxide.

4. The process as set forth in claim 3 , wherein in step b) the temperature is from about 50° C. to about 150° C.

5. The process as set forth in claim 4 , wherein in step c) the cooling temperature is from about 10° C. to about 50° C.

6. The process as set forth in claim 5 , wherein in step b), the time is from about 1 minute to about 60 minutes.

7. The process as set forth in claim 6 , wherein in step d) the pH is from about 7 to about 9 and the organic acid is acetic acid.

8. In a process for the improvement of the color of trimethylolpropane (TMP) including the steps of preparing a crude aqueous solution of TMP containing color causing impurities, distilling the solution evaporating excess water from the same, extracting the TMP from the solution, and purifying the extracted TMP, the improvement which comprises the steps of adding an alkaline material to the crude TMP solution after the evaporation step to react with the color causing impurities, cooling the TMP solution and then adding an organic acid thereto to partially neutralize the TMP solution and then proceeding with the extraction and purification steps to form TMP with an improved color.

Assignments (7)
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT [RECORDED ON JUNE 21, 2024 AT REEL 067806, FRAME 0536] Recorded Apr 8, 2025
From: CANTOR FITZGERALD SECURITIES [AS THE COLLATERAL AGENT]
To: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
Reel/Frame 070773/0022 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2024
From: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 067806/0536 →
CHANGE OF NAME Recorded Aug 25, 2021
From: OXEA BISHOP LLC
To: OQ CHEMICALS BISHOP LLC
Reel/Frame 057311/0541 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 030795, FRAME 0445 Recorded Oct 12, 2017
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: OXEA CORPORATION; OXEA BISHOP, LLC
Reel/Frame 044203/0977 →
RELEASE OF SECURITY INTEREST Recorded Dec 21, 2015
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: OXEA CORPORATION; OXEA BISHOP, LLC
Reel/Frame 037341/0546 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Jul 15, 2013
From: OXEA CORPORATION; OXEA BISHOP, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030795/0378 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Jul 15, 2013
From: OXEA CORPORATION; OXEA BISHOP, LLC
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 030795/0445 →