Process for removing chloropropanols and/or glycidol, or their fatty acid esters, from glyceride oil, and an improved glyceride oil refining process comprising the same

Patent metadata

Field	Value
Publication number	US-10316268-B2
Application number	US-201615576003-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 27, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

The present invention is directed to a basic ionic liquid treatment for removing chloropropanol and/or glycidol, or their fatty acid esters, from glyceride oil, as well as a process for refining glyceride oil which includes the basic ionic liquid treatment. The present invention also relates to uses of the basic ionic liquid and glyceride oil compositions obtained from the ionic liquid treatment.

First claim

The invention claimed is:

1. A process for removing chloropropanol and/or glycidol, or their fatty acid esters, from glyceride oil comprising the steps of:
(i) contacting glyceride oil comprising chloropropanol and/or glycidol, or their fatty acid esters, with a basic ionic liquid to form a treated glyceride oil, wherein the basic ionic liquid comprises a basic anion selected from hydroxide, alkoxide, alkylcarbonate, hydrogen carbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate, and lysinate; and an organic quaternary ammonium cation; and
(ii) separating the treated glyceride oil from an ionic compound comprising the organic quaternary ammonium cation after contacting the glyceride oil with the basic ionic liquid; wherein the treated glyceride oil has a reduced concentration of chloropropanol and/or glycidol, or their fatty acid esters, compared to the glyceride oil contacted in step (i).

2. A process according to claim 1 , wherein the process further comprises subjecting the glyceride oil to at least one refining step before and/or after contacting the glyceride oil with the basic ionic liquid.

3. A process according to claim 2 , wherein the at least one refining step is selected from: degumming, bleaching, winterization, depigmentation and deodorization.

4. A process according to claim 3 , wherein the at least one refining step comprises deodorization.

5. A process according to claim 4 , wherein the deodorisation includes steam stripping and is conducted at a temperature of from 160 to 270° C., or at a temperature of from 160° C. to 200° C., or at a temperature of from 170° C. to 190° C.

6. A process according to claim 1 , wherein the total concentration of monochloropropanol and fatty acid esters thereof, in the glyceride oil which is contacted with the basic ionic liquid is from 0.01 ppm to 30 ppm.

7. A process according to claim 1 , wherein the treated glyceride oil which is separated has a total concentration of monochloropropanol and fatty acid esters thereof which is at least 50 wt. %, or at least 75 wt. %, lower than that of the glyceride oil which is contacted with the basic ionic liquid; or wherein the treated glyceride oil which is separated has a total concentration of glycidyl fatty acid esters which is at least 50 wt. %, or at least 75 wt. %, lower than that of the glyceride oil contacted with the basic ionic liquid.

8. A process according to claim 1 , wherein the step of contacting the glyceride oil with the basic ionic liquid is conducted at a temperature of less than 80° C., or from 25 to 65° C., or from 35 to 55° C.

9. A process according to claim 1 , wherein the organic quaternary ammonium cation of the basic ionic liquid 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 a C 1 to C 8 , straight chain or branched alkyl group or a C 3 to C 6 cycloalkyl group; or any two of R a , R b , R c and R d combine to form an alkylene chain —(CH 2 ) q — wherein q is from 3 to 6; and wherein said alkyl or cycloalkyl groups may optionally be substituted 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 (C 1 to C 6 )alkyl and —OC(O)(C 1 to C 6 )alkyl, for example one to three —OH groups; or
wherein the organic quaternary ammonium cation of the basic ionic liquid 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 a C 1 to C 4 , straight chain or branched alkyl group, including C 1 , C 2 and C 4 alkyl, wherein at least one of R a , R b , R c or R d is substituted by a single —OH group.

10. A process according to claim 9 , wherein the organic quaternary ammonium cation of the basic ionic liquid is choline:

11. A process according to claim 1 , wherein the basic anion is selected from alkylcarbonate, hydrogen carbonate and carbonate.

12. A process according to claim 1 , wherein the basic anion is selected from hydroxide and alkoxide.

13. A process according to claim 1 , wherein the glyceride oil is contacted with a liquid comprising the basic ionic liquid and a solvent, wherein the concentration of basic ionic liquid in the liquid is 15 wt. % to 90 wt. %.

14. A process according to claim 13 , wherein the glyceride oil is contacted with a liquid comprising the basic ionic liquid and a solvent, wherein
i) the concentration of basic ionic liquid in the liquid is 50 wt. % to 90 wt. %, or from 75 wt. % to 85 wt, and the basic ionic liquid is as defined in claim 11 ; or
ii) the concentration of basic ionic liquid in the liquid is 15 wt. % to 60 wt. %, or from 40 wt. % to 50 wt, and the basic ionic liquid is as defined in claim 12 .

15. A process according to claim 11 , wherein the basic ionic liquid is choline bicarbonate and the glyceride oil which is contacted comprises FFA and the ionic compound separated from the glyceride oil is a choline-FFA salt, and wherein the process further comprises a step of regenerating the choline bicarbonate basic ionic liquid from the ionic compound which is a separated from the treated oil; said regeneration comprising the steps of:
(a) contacting the choline-FFA salt with carbonic acid; and
(b) obtaining choline bicarbonate from the reaction mixture.

16. A process according to claim 1 , 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 and sunflower oil, or mixtures thereof.

17. A composition comprising a glyceride oil and a basic ionic liquid;
wherein the basic ionic liquid comprises a basic anion selected from hydroxide, alkoxide, alkylcarbonate, hydrogen carbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate and lysinate; and a organic quaternary ammonium cation; and
wherein the glyceride oil of the composition has a total aldehyde and ketone content of less than 20 mg/kg; and/or wherein the p-anisidine value of the oil is less than 10.

18. A composition according to claim 17 , wherein the total concentration of monochloropropanol and fatty acid esters thereof in the glyceride oil is at least 0.01 ppm; and/or the total concentration of glycidyl fatty acid esters in the glyceride oil in the above aspects is at least 0.1 ppm.

19. A composition according to claim 18 , wherein the total concentration of monochloropropanol and fatty acid esters thereof, in the glyceride oil is from 0.01 ppm to 30 ppm, from 1 ppm to 25 ppm, or from 1.5 ppm to 20 ppm; and/or wherein the total concentration of glycidyl fatty acid esters in the glyceride oil is from 0.1 ppm to 30 ppm, from 1 ppm to 25 ppm, or from 1.5 ppm to 20 ppm.

20. A composition according to claim 17 , wherein the basic ionic liquid is choline bicarbonate or choline hydroxide.

Assignees

• Univ Belfast
• Evonik Degussa Gmbh

Inventors

• Goodrich Peter
• O'Hara Eoghain
• Atkins Martin
• Hamer Christopher K
• Witthaut Daniel
• Fedor Gabriela
• Boes Ulrich

Classifications

• C11B3/06 Primary

  with bases · CPC title

• A23D9/04

  Working-up · CPC title

• Y02E50/13

  Cross-Sectional Technologies · mapped topic

• C11B3/006

  by extraction · CPC title

• C11B3/02

  by chemical reaction {(C11B3/003 takes precedence)} · CPC title