IP Library Granted Patent US 9,533,936
Granted Patent B1
US 9,533,936 · App. 15/183,289 · Granted Jan 3, 2017

Removal of fatty acid from esterified propoxylated glycerin

Inventors: Leopold Strecker (Warren, NJ); David Rowe (Indianapolis, IL); Dana Overman (Roswell, GA); Louie Flowers (Greenville, NC); Aaron Milhouse (Neeses, SC); Chess Mizell (Sanford, MI)
Assignee: CHOCO FINESSE LLC
C07C67/54A23D9/007A23G1/36A23V2002/00
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Quick Facts
Patent No.
US 9,533,936
App. No.
15/183,289
Granted
Jan 3, 2017
Kind
B1
Abstract

An esterified propoxylated glycerin process is improved by the incorporation of a vacuum distillation step whereby unreacted fatty acids are removed in a form suitable for direct reuse in a further esterification. The esterified propoxylated glycerin produced is low in color and has a low content of free fatty acid, making it suitable for use as a reduced calorie fat substitute in various food products.

Claims (21)

1. A method of refining an esterified propoxylated glycerin product comprised of esterified propoxylated glycerin and unreacted fatty acid, comprising subjecting the esterified propoxylated glycerin product to conditions whereby at least a portion of the unreacted fatty acid is volatilized under vacuum in the absence of added water and separated from a liquid phase comprised of the esterified propoxylated glycerin.

2. The method of claim 1 , wherein the esterified propoxylated glycerin product is heated at a temperature of from about 200° C. to about 300° C.

3. The method of claim 1 , wherein the esterified propoxylated glycerin product is heated at a temperature of from about 220° C. to about 280° C.

4. The method of claim 1 , wherein the esterified propoxylated glycerin product is subjected to a pressure of not more than about 1 mm Hg.

5. The method of claim 1 , wherein the esterified propoxylated glycerin product is subjected to a pressure of not more than about 0.1 mm Hg.

6. The method of claim 1 , wherein the esterified propoxylated glycerin product is subjected to said conditions for less than about 5 minutes.

7. The method of claim 1 , wherein the esterified propoxylated glycerin product is subjected to a pressure of not more than about 1 mm Hg at a temperature of from about 220° C. to about 280° C.

8. The method of claim 1 , wherein the esterified propoxylated glycerin product is subjected to a pressure of not more than about 0.1 mm Hg at a temperature of from about 240° C. to about 270° C.

9. The method of claim 1 , wherein a thin liquid film of the esterified propoxylated glycerin product is formed on a heated surface under vacuum.

10. The method of claim 1 , wherein the method is carried out in a centrifugal still.

11. The method of claim 10 , wherein the centrifugal still comprises a heated rotating disk and the esterified propoxylated glycerin product has a residence time on the heated rotating disk of less than about 5 seconds.

12. The method of claim 10 , wherein the centrifugal still comprises a heated rotating disk and the heated rotating disk is maintained at a temperature of from about 220° C. to about 280° C.

13. The method of claim 10 , wherein the centrifugal still comprises a vacuum chamber and the vacuum chamber is maintained at a pressure of less than about 1 mm Hg.

14. The method of claim 10 , wherein the centrifugal still comprises a heated rotating disk maintained at a temperature of from about 240° C. to about 270° C. and a vacuum chamber maintained at a pressure of less than about 0.1 mm Hg, the esterified propoxylated glycerin product having a residence time on the heated rotating disk of less than about 5 seconds.

15. The method of claim 1 , wherein the method is carried out in a wiped or falling film evaporator.

16. The method of claim 1 , wherein the liquid phase obtained following separation of at least a portion of the unreacted fatty acid comprises no more than 0.5 weight % free fatty acid, calculated as oleic acid.

17. The method of claim 1 , wherein the esterified propoxylated glycerin product initially is comprised of from 1 to about 20 weight % unreacted fatty acid, calculated as oleic acid.

18. The method of claim 1 , wherein the esterified propoxylated glycerin product is obtained by reacting propoxylated glycerin with an excess of fatty acid.

19. The method of claim 1 , wherein the esterified propoxylated glycerin product has been subjected to a bleaching step prior to separation of the unreacted fatty acid.

20. The method of claim 1 , wherein unreacted fatty acid separated from the liquid phase is recycled for use in esterifying propoxylated glycerin to produce esterified propoxylated glycerin.

21. The method of claim 1 , wherein unreacted fatty acid separated from the liquid phase is directly recycled for use, without further refinement or purification, in esterifying propoxylated glycerin to produce esterified propoxylated glycerin.

Assignments (3)
SECURITY INTEREST Recorded Jan 15, 2026
From: EPOGEE, LLC; LINUS TECHNOLOGY OPCO, INC.; LINUS TECHNOLOGY MERGERSUB, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 073489/0314 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2019
From: CHOCO FINESSE, LLC
To: EPOGEE, LLC
Reel/Frame 049173/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2016
From: STRECKER, LEOPOLD; ROWE, DAVID; OVERMAN, DANA; FLOWERS, LOUIE; MILHOUSE, AARON; MIZELL, CHESS
To: CHOCO FINESSE LLC
Reel/Frame 038938/0282 →