Process for removing metal from a metal-containing glyceride oil comprising a basic quaternary ammonium salt treatment

Patent metadata

Field	Value
Publication number	US-10150933-B2
Application number	US-201615576700-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 27, 2015
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The present invention relates to a process for removing metal from metal-containing glyceride oil comprising the steps of:
(i) contacting a glyceride oil, comprising chromium, manganese, iron, cobalt, nickel and/or copper in a total amount of from 10 mg/kg to 10,000 mg/kg, with a liquid comprising a basic quaternary ammonium salt to form a treated glyceride oil; wherein the basic quaternary ammonium salt comprises a basic anion selected from hydroxide, alkoxide, alkylcarbonate, hydrogen carbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate and lysinate; and (ii) separating the treated glyceride oil from a salt comprising the quaternary ammonium cation, providing a treated glyceride oil containing a reduced amount of metals.

First claim

The invention claimed is:

1. A process for removing metal from a metal-containing glyceride oil comprising the steps of:
(i) contacting a glyceride oil, comprising at least one metal from the group consisting of chromium, manganese, iron, cobalt, nickel and copper, with a liquid comprising a basic quaternary ammonium salt to form a treated glyceride oil; wherein said glyceride oil contains said metals in a total amount of from 10 mg/kg to 10,000 mg/kg, and wherein the basic quaternary ammonium salt comprises a basic anion selected from hydroxide, alkoxide, alkylcarbonate, hydrogen carbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate and lysinate; and a quaternary ammonium cation; and
(ii) separating the treated glyceride oil from a salt comprising the quaternary ammonium cation after contacting the glyceride oil with the quaternary ammonium salt, providing a treated glyceride oil containing a reduced amount of said metals compared to the glyceride oil contacted in step (i).

2. The process of claim 1 , comprising the additional step of:
(iii) subjecting the treated glyceride oil after the separation step to at least one further refining step.

3. The process of claim 2 , wherein the at least one further refining step comprises a deodorisation step.

4. The process of claim 3 , wherein the deodorisation step involves steam stripping conducted at a temperature of from 160° C. to 270° C.

5. The process of claim 3 , wherein the deodorisation step involves steam stripping conducted at a temperature of from 160° C. to 240° C.

6. The process of claim 2 , wherein the process further comprises at least one additional refining step of the glyceride oil conducted prior to the treatment with the basic quaternary ammonium salt in step (i), the at least one additional refining step being selected from bleaching and degumming.

7. The process of claim 2 , wherein the at least one further refining step (iii) comprises a deodorisation step and the process does not comprise a step of degumming or bleaching.

8. The process of claim 1 , wherein the total amount of said metals in the glyceride oil prior to contacting in step (i) is 50 mg/kg to 5,000 mg/kg.

9. The process of claim 1 , wherein the treated glyceride oil separated in step (ii) contains said metals in a total amount which is less than 50% of the total amount of said metals in the untreated glyceride oil contacted in step (i).

10. The process of claim 1 , wherein the treated glyceride oil separated in step (ii) contains said metals in a total amount which is less than 75% of the total amount of said metals in the untreated glyceride oil contacted in step (i).

11. The process of claim 1 , wherein the salt separated in step (ii) comprises an anion of a free fatty acid.

12. The process of claim 1 , wherein the contacting step is conducted at a temperature of less than 80° C.

13. The process of claim 1 , wherein the contacting step is conducted at a temperature of from 35 to 55° C.

14. The process of claim 1 , wherein the quaternary ammonium cation is selected from:
[N(R a )(R b )(R c )(R d )] + ,

wherein R a , R b , R c and R d are each independently selected from C 1 to C 8 alkyl, wherein one or more of R a , R b , R c or R d may optionally be substituted at carbon atoms that are not bonded to the nitrogen atom by one to three groups selected from: C 1 to C 4 alkoxy, C 2 to C 8 alkoxyalkoxy, C 3 to C 6 cycloalkyl, OH, SH, CO 2 R e , and OC(O)R e , where R e is C 1 to C 6 alkyl.

15. The process of claim 14 , wherein R a , R b , R c and R d are each independently selected from C 1 to C 4 alkyl, wherein at least one of R a , R b , R c or R d is substituted each by a single —OH group.

16. The process of claim 14 , wherein the quaternary ammonium cation is choline: (CH 3 ) 3 N + CH 2 CH 2 OH.

17. The process of claim 1 , wherein the basic anion is selected from alkylcarbonate, hydrogen carbonate and carbonate.

18. The process of claim 17 , wherein the quaternary ammonium salt contacted in step (i) is choline bicarbonate: (CH 3 ) 3 N + CH 2 CH 2 OH HOCOO − .

19. The process of claim 1 , wherein the basic anion is selected from hydroxide and alkoxide.

20. The process of claim 19 , wherein the basic quaternary ammonium salt contacted in step (i) is choline hydroxide: (CH 3 ) 3 N + CH 2 CH 2 OH OH − .

21. The process of claim 1 , wherein the liquid comprising the basic quaternary ammonium salt comprises a solvent and the concentration of quaternary ammonium salt in the liquid is 15 wt. % to 90 wt. %.

22. The process of claim 21 , wherein the solvent is an aqueous solvent.

23. The process of claim 18 , wherein the liquid comprising the basic quaternary ammonium salt comprises an aqueous solvent and wherein the concentration of quaternary ammonium salt in the liquid is 50 wt. % to 90 wt. %.

24. The process of claim 20 , wherein the liquid comprising the basic quaternary ammonium salt comprises an aqueous solvent and wherein the concentration of quaternary ammonium salt in the liquid is 15 wt. % to 60 wt. %.

25. The process of claim 1 , wherein the glyceride oil is a vegetable oil.

26. The process of claim 25 , wherein the vegetable oil is selected from coconut oil, corn oil, cottonseed oil, groundnut oil, olive oil, palm oil, rapeseed oil, rice bran oil, safflower oil, soybean oil, sunflower oil, and mixtures thereof.

27. The process of claim 1 , wherein the glyceride oil is palm oil.

28. A method for reducing the metal content of a metal-containing glyceride oil, comprising contacting a glyceride oil with a basic quaternary ammonium salt, said basic quaternary ammonium salt comprising a basic anion selected from hydroxide, alkoxide, alkylcarbonate, hydrogen carbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate and lysinate; and a quaternary ammonium cation.

29. The method of claim 28 , wherein the glyceride oil is a vegetable oil selected from coconut oil, corn oil, cottonseed oil, groundnut oil, olive oil, palm oil, rapeseed oil, rice bran oil, safflower oil, soybean oil, sunflower oil, and mixtures thereof.

30. The method of claim 28 , wherein the glyceride oil is palm oil.

31. The method of claim 28 , wherein the quaternary ammonium cation is selected from:
[N(R a )(R b )(R c )(R d )] + ,

wherein R a , R b , R c and R d are each independently selected from C 1 to C 8 alkyl, wherein one or more of R a , R b , R c or R d may optionally be substituted at carbon atoms that are not bonded to the nitrogen atom by one to three groups selected from: C 1 to C 4 alkoxy, C 2 to C 8 alkoxyalkoxy, C 3 to C 6 cycloalkyl, OH, SH, CO 2 R e , and OC(O)R e , where R e is C 1 to C 6 alkyl.

32. The method of claim 31 , wherein R a , R b , R c and R d are each independently selected from C 1 to C 4 alkyl, wherein at least one of R a , R b , R c or R d is substituted each by a single —OH group.

33. The method of claim 31 , wherein the quaternary ammonium cation is choline: (CH 3 ) 3 N + CH 2 CH 2 OH.

34. The method of claim 28 , wherein the quaternary ammonium salt is choline bicarbonate: (CH 3 ) 3 N + CH 2 CH 2 OH HOCOO − .

35. The method of claim 28 , wherein

Assignees

• Evonik Degussa Gmbh

Inventors

• Fedor Gabriela
• Atkins Martin Philip
• Goodrich Peter
• Hamer Christopher Klatt
• Witthaut Daniel
• Boes Ulrich

Classifications

• C11B3/14

  with the use of indifferent gases or vapours, e.g. steam · CPC title

• C11B3/006

  by extraction · CPC title

• C11B3/04

  with acids · CPC title

• C11B3/001

  by a combination of two or more of the means hereafter · CPC title

• C11B3/06 Primary

  with bases · CPC title