Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid

• US 10,544,381 B2
• Filed: 02/07/2019
• Issued: 01/28/2020
• Est. Priority Date: 02/07/2018
• Status: Active Grant

• Current Assignee: Sartec
• Original Assignee: Sartec
• Inventors: McNeff, Charles Vincent, McNeff, Clayton V., McNeff, Larry C., Yan, Bingwen
• Primary Examiner(s): Carr, Deborah D
• Application Number:
  US16/270,205
• Publication Number:
  US 20190241836A1
• Time in Patent Office: 355 Days
• Field of Search: 554170
• CPC Class Codes: B01J 21/04 Alumina
• CPC Class Codes: B01J 21/063 Titanium; Oxides or hydroxides thereof
• CPC Class Codes: B01J 21/066 Zirconium or hafnium; Oxides or hydroxides thereof
• CPC Class Codes: C11B 13/02 from soap stock
• CPC Class Codes: C11C 1/002 Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02W 30/74 Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Abstract

Embodiments herein relate to the production of alkyl esters from acidified soap stock. In an embodiment, a process for producing alkyl esters is provided. The process can include mixing acidified soap stock with an alcohol, water, carbon dioxide, and/or carbon monoxide, to form a reaction mixture, and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst including a metal oxide. Other embodiments are also included herein.

Claims

1. A process for producing alkyl esters comprising:

mixing an acidified soap stock with an alcohol, water, carbon dioxide and/or one or more acids to form a reaction mixture; and

contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst comprising a metal oxide.

2. The process of claim 1, the metal oxide selected from the group consisting of alumina, titania, zirconia, and hafnia.

3. The process of claim 1, the soap stock comprising a byproduct derived from tall oil, rapeseed oil, soybean oil, canola oil, cottonseed oil, grape seed oil, mustard seed oil, corn oil, linseed oil, sunflower oil, poppy-seed oil, walnut oil, peanut oil, rice bran oil, camellia oil, castor oil, and olive oil, palm kernel oil, coconut oil, rice oil, algae oil, seaweed oil, or Chinese Tallow tree oil.

4. The process of claim 1, the soap stock having an acid number of greater than or equal to 3 mg KOH/g oil.

5. The process of claim 4, wherein the step of contacting the reaction mixture with a catalyst comprises conversion of the soap stock from an acid number of equal to 3 mg KOH/g oil to an acid number of less than or equal to 0.5 mg KOH/g oil.

6. The process of claim 1, the acid comprising an organic acid.

7. The process of claim 1, the acid comprising a Bronsted acid.

8. The process of claim 1, the acid comprising an inorganic acid.

9. The process of claim 1, further including mixing an inorganic base or an organic base into the reaction mixture.

10. The process of claim 1, wherein the step of contacting the reaction mixture with a catalyst is performed at a temperature of between 200 and 400 degrees Celsius.

11. The process of claim 1, wherein the step of contacting the reaction mixture with a catalyst is performed at a pressure of between 1000 and 5000 psi.

12. The process of claim 1, the alcohol comprising a C1-C6 alcohol.

13. The process of claim 1, the alcohol comprising an alcohol selected from the group consisting of methanol and ethanol.

14. The process of claim 1, wherein carbon dioxide is present in an amount equal to at least 0.1 wt. percent of the mass of the alcohol added.

15. The process of claim 1, wherein carbon dioxide is present in an amount equal to at least 0.5 wt. percent of the mass of the alcohol added.

16. The process of claim 1, the reaction mixture comprising carbonic acid.

17. The process of claim 1, the reaction mixture comprising carbonic acid at concentration of at least 0.05 M.

18. The process of claim 1, the reaction mixture comprising carbonic acid at concentration of at least 1 M.

19. The process of claim 1, wherein the pH of the reaction mixture is less than 7.

20. The process of claim 1, wherein the pH of the reaction mixture is less than 3.