IP Library Granted Patent US 8,455,699
Granted Patent B2
US 8,455,699 · App. 13/569,621 · Granted Jun 4, 2013

Production and separation of glycerol-related products using various feed stocks

Inventors: Patrick G. Hatcher (Suffolk, VA); Zhanfei Liu (Norfolk, VA); Elodie Salmon (Norfolk, VA)
Assignee: Old Dominion University Research Foundation
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Quick Facts
Patent No.
US 8,455,699
App. No.
13/569,621
Granted
Jun 4, 2013
Kind
B2
Abstract

Disclosed are processes for producing glycerol-related products. One process for producing glycerol-related products comprises introducing glycerol and an alkylation reagent to a substantially oxygen free environment. Another process for producing glycerol-related products comprises introducing a glycerol and tetramethylammonium hydroxide to a substantially oxygen free environment.

Claims (31)

1. A process for producing glycerol-related products comprising:

introducing a feedstock and an alkylation reagent to a substantially oxygen free environment;

hydrolyzing at a temperature at or above 200° C. one or more lipid glycerides in the feedstock;

methylating one or more fatty acids in the feedstock with methyl groups from the alkylation reagent, wherein the hydrolyzing and methylating occur contemporaneously;

separating a lower phase from an upper phase of a resulting condensate, the lower phase comprised of biodiesel;

acidifying the upper phase;

separating the acidified upper phase into biodiesel dissolved in methanol and methoxylated glycerols dissolved in methanol;

removing the methanol from both the biodiesel and the methoxylated glycerols; and

separating the biodiesel from the methoxylated glycerols.

2. The process of claim 1 , wherein the alkylation reagent is tetramethylammonium hydroxide.

3. The process of claim 2 , wherein the methlylated glycerol-related products are one or more of 1,2,3-trimethoxy-propane (TMP), 1,3-dimethoxy-2-propanol (DMP), 1,2-dimethoxy-3-propanol (2DMP) and 3-methoxy-1,2-dihydroxypropane (MDP).

4. The process of claim 1 , wherein the temperature is between about 250° C. and about 500° C. and the pressure is atmospheric.

5. The process of claim 1 , wherein the feedstock is an algal biomass.

6. The process of claim 1 , wherein the feedstock is one or more of glyceride based oils from plants, glyceride based oils from animal fat and used cooking oil.

7. The process of claim 1 , wherein at least one by-product of the processed alkylation reagent is converted and recycled as the alkylation reagent.

8. The process of claim 2 , wherein a trimethylamine by-product of the processed tetramethylammonium hydroxide is converted and recycled as the alkylation reagent.

9. The process of claim 1 , wherein the alkylation reagent is selected from one or more of tetramethylammonium hydroxide, tetrabutylammonium hydroxide, trimethylphenylammonium hydroxide, tetraethyammonium hydroxide, and (m-trifluoro-methylphenyl)trimethylammonium hydroxide.

10. The process of claim 1 , wherein the substantially oxygen free environment comprises less than or equal to one percent oxygen.

11. The process of claim 1 , wherein the methanol is removed with distillation.

12. A process for producing glycerol-related products comprising:

hydrolyzing and methylating glycerol with an alkylation reagent in a substantially oxygen free environment without a catalyst, wherein the glycerol is methoxylated glycerols produced from one or more of an algal biomass and glyceride based oils.

13. The process of claim 12 , wherein the glyceride based oils are glyceride based oils from plants, glyceride based oils from animal fat and used cooking oil.

14. The process of claim 12 , wherein the alkylation reagent is tetramethylammonium hydroxide.

15. The process of claim 14 , wherein the glycerol-related products are one or more of 1,2,3-trimethoxy-propane (TMP), 1,3-dimethoxy-2-propanol (DMP), and 1,2-dihydroxy-3-methoxy propane (MDP).

16. The process of claim 14 , wherein a trimethylamine by-product of the processed tetramethylammonium hydroxide is converted and recycled as the alkylation reagent.

17. The process of claim 12 , wherein the temperature is between about 250° C. and about 500° C. and the pressure is atmospheric.

18. The process of claim 12 , wherein at least one by-product of the processed alkylation reagent is converted and recycled as the alkylation reagent.

19. The process of claim 12 , wherein the alkylation reagent is selected from one or more of tetramethylammonium hydroxide, tetrabutylammonium hydroxide, trimethylphenylammonium hydroxide, tetraethyammonium hydroxide, and (m-trifluoro-methylphenyl)trimethylammonium hydroxide.

20. Glycerol-related products produced from the process of claim 12 .

21. A process for producing glycerol-related products comprising:

hydrolyzing and methylating glycerol with an alkylation reagent in a substantially oxygen free environment without a catalyst, wherein the glycerol is crude glycerin produced from a biodiesel production facility.

Assignments (3)
CONFIRMATORY LICENSE Recorded Sep 18, 2023
From: OLD DOMINION UNIVERSITY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 064931/0193 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 31, 2012
From: OLD DOMINION UNIVERSITY
To: OLD DOMINION UNIVERSITY RESEARCH FOUNDATION
Reel/Frame 028880/0128 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2012
From: HATCHER, PATRICK G.; LIU, ZHANFEI; SALMON, ELODIE
To: OLD DOMINION UNIVERSITY
Reel/Frame 028877/0613 →
Continuity (6)
Continuation In Part 13204884 · Aug 8, 2011
Continuation In Part 12336707 · Dec 17, 2008
Provisional Application 61015926 · Dec 21, 2007
Provisional Application 61535525 · Sep 16, 2011
Provisional Application 61558044 · Nov 10, 2011
Related Publication 20120323044A1 · Dec 20, 2012