Emulsifiers

Abstract

A non-hydrogenated, non-palm emulsifier composition comprises: at least 20% by weight monoglycerides; less than 60% by weight of diglycerides; and from 0-80% by weight triglycerides, wherein the weight % is with respect to the total of monoglycerides, diglycerides and triglycerides, and wherein the fatty acid residues bound to the monoglycerides, diglycerides and triglycerides in the emulsifier composition comprise: from 20% to 75% by weight stearic acid (C18:0); from 15% to 60% by weight oleic acid (C18:1); and from 1% to 10% by weight palmitic acid (C16:0), based on the total weight of C8 to C24 fatty acids. The composition is obtainable by a method comprising the reaction of a fat with glycerol in the presence of an enzymatic catalyst

Claims

1. A non-hydrogenated, non-palm emulsifier composition comprising: at least 20% by weight monoglycerides; less than 60% by weight of diglycerides; and and from 0-80% by weight triglycerides, wherein the weight % is with respect to the total of the monoglycerides, diglycerides and triglycerides, and wherein fatty acid residues bound to the monoglycerides, diglycerides and triglycerides in the emulsifier composition comprise: from 20% to 75% by weight stearic acid (C18:0); from 15% to 60% by weight oleic acid (C18:1); and from 1% to 10% by weight palmitic acid (C16:0), based on the total weight of C8 to C24 fatty acids, and wherein the composition is obtained by a method comprising the reaction of a fat with glycerol in the presence of an enzymatic catalyst.

2. The composition according to claim 1, wherein the weight ratio of stearic acid to oleic acid is from 4:1 to 1:4.

3. The composition according to claim 1, wherein the fat is from at least one non-palm source selected from shea and sal, or combinations thereof.

4. The composition according to claim 3, wherein the non-palm source comprises a butter or a fraction thereof.

5. The composition according to claim 1, wherein the enzymatic catalyst is a lipase.

6. The composition according to claim 1, comprising from 20% to 95% by weight monoglycerides.

7. The composition according to claim 1, comprising from 1% to 50% by weight diglycerides.

8. The composition according to claim 1, wherein the weight ratio of monoglycerides to diglycerides is higher than 1:10.

9. The composition according to claim 1, comprising from 1% to 12% by weight linoleic acid (C18:2).

10. The composition according to claim 1, comprising from 25% to 70% by weight stearic acid.

11. The composition according to claim 1, comprising from 20% to 55% by weight oleic acid.

12. The composition according to claim 1, comprising from 1% to 8% by weight palmitic acid.

13. A food product comprising the composition according to claim 1.

14. A method for preparing the emulsifier composition according to claim 1, comprising: providing a fat comprising triglycerides, and reacting the fat with glycerol in a glycerolysis reaction in the presence of an enzymatic catalyst.

15. The method according to claim 14, wherein the fat is selected from shea butter, shea olein, shea stearin, sal butter, sal stearin, sal olein, and mixtures thereof.

16. The composition according to claim 1, wherein the weight ratio of stearic acid to oleic acid is from 2:1 to 1:2.

17. The composition according to claim 1, wherein the weight ratio of monoglycerides to diglycerides is higher than 1:4.

18. The composition according to claim 9, comprising from 1% to 10% by weight linoleic acid (C18:2).

19. The food product according to claim 13, wherein the food product is selected from the group consisting of puff pastry, cake, Danish rolls and water-based fillings.

Description

EXAMPLES

Example 1

[0078] Crude shea olein is obtained after solvent fractionation of crude shea butter. The fatty acid composition of the products in w/w is given in the following Table 1.

TABLE-US-00001 C8:0 0 C10:0 0 C12:0 0 C15:0 0 C14:0 0.1 C16:0 5.1 C16:1C 0.1 C16:1T 0 C17:0 0.1 C18:0 31.9 C18:1 52.3 C18:1T 0 C18:1C 52.2 C18:2 8 C18:2T 0 C18:2C 8 C18:3 0.3 C18:3T 0.1 C18:3C 0.2 Total Trans 0.1 C20:0 1.2 C20:1C 0.4 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0

[0079] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4).

[0080] 400 g of the crude shea olein was esterified with 102.4 g glycerol in the presence of immobilized lipase originating from Candida antarctica B (Novozym® 435). When the reaction was completed, after approximatively 24 hours, the product was filtered. Then this product was bleached and deodorised at low temperature (mild refining) to obtain the emulsifier composition, which has the following composition, w/w (Table 2):

TABLE-US-00002 C8:0 0 C10:0 0 C12:0 0 C15:0 0 C14:0 0.1 C16:0 4.9 C16:1C 0.1 C16:1T 0 C17:0 0.1 C18:0 32.5 C18:1 52.2 C18:1T 0 C18:1C 52.2 C18:2 7.9 C18:2T 0 C18:2C 7.9 C18:3 0.3 C18:3T 0.1 C18:3C 0.2 Total Trans 0.2 C20:0 1.3 C20:1C 0.4 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0 Triglyceride 21.9 Diglyceride 43.4 Monoglyceride 23.8

[0081] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E)).

Example 2

[0082] 600 g refined shea stearin obtained from shea butter by solvent fractionation was esterified with 76.8 g glycerol in the presence of immobilized lipase originating from Candida antarctica B (Novozym® 435). When the reaction was completed, after approximatively 24 hours, the product was filtered. The product has the following composition, w/w (Table 3):

TABLE-US-00003 C8:0 0 C10:0 0 C12:0 0.1 C15:0 0 C14:0 0.1 C16:0 3.6 C16:1C 0 C16:1T 0 C17:0 0.1 C18:0 59.7 C18:1 31.5 C18:1T 0 C18:1C 31.4 C18:2 2.9 C18:2T 0.1 C18:2C 2.8 C18:3 0.1 C18:3T 0 C18:3C 0.1 Total Trans 0.1 C20:0 1.7 C20:1C 0 C20:2C 0 C22:0 0.2 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0 Triglyceride 26.3 Diglyceride 45.5 Monoglyceride 26.8

[0083] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E)).

[0084] The product containing monoglycerides was distilled in order to separate monoglycerides from triglycerides and diglycerides by means of short path distillation at a temperature of about 180° C. and a pressure of about 1×10.sup.−2 mbar. The concentrated monoglyceride product was collected as distillate. The concentrated monoglyceride emulsifier composition has the following composition, w/w (Table 4):

TABLE-US-00004 C8:0 0 C10:0 0 C12:0 0.2 C15:0 0 C14:0 0.1 C16:0 5.5 C16:1C 0 C16:1T 0 C17:0 0.1 C18:0 66.2 C18:1 24 C18:1T 0 C18:1C 23.9 C18:2 2.2 C18:2T 0 C18:2C 2.2 C18:3 0 C18:3T 0 C18:3C 0 Total Trans 0 C20:0 1.5 C20:1C 0 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0 C24:1C 0 Triglyceride 1.2 Diglyceride 5.7 Monoglyceride 91.3

[0085] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E))

Example 3

[0086] Sal olein is obtained after solvent fractionation of sal butter. The fatty acid composition of the product is given in the following Table 5.

TABLE-US-00005 C8:0 0 C10:0 0 C12:0 0 C15:0 0.1 C14:0 0.1 C16:0 7.5 C16:1C 0.1 C16:1T 0 C17:0 0.2 C18:0 28.2 C18:1 53.2 C18:1T 0.4 C18:1C 52.8 C18:2 3.4 C18:2T 0 C18:2C 3.4 C18:3 0.9 C18:3T 0.1 C18:3C 0.8 Total Trans 0.5 C20:0 4.7 C20:1C 0.6 C20:2C 0.1 C22:0 0.4 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.2 C24: 1C 0

[0087] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4).

[0088] 420 g sal olein was esterified with 105 g glycerol in the presence of immobilized lipase originating from Candida antarctica B (Novozym® 435). When the reaction was completed, after approximatively 24 hours, the product was filtered. Then this product was bleached and deodorised at low temperature (mild refining) to obtain the emulsifier composition, which has the following composition, w/w (Table 6):

TABLE-US-00006 C8:0 0 C10:0 0 C12:0 0 C15:0 0.1 C14:0 0.1 C16:0 7.4 C16:1C 0.1 C16:1T 0 C17:0 0.2 C18:0 28.3 C18:1 53.2 C18:1T 0.4 C18:1C 52.8 C18:2 3.4 C18:2T 0 C18:2C 3.4 C18:3 0.9 C18:3T 0.1 C18:3C 0.8 Total Trans 0.5 C20:0 4.8 C20:1C 0.6 C20:2C 0.1 C22:0 0.4 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.2 C24:1C 0 Triglyceride 24 Diglyceride 47.8 Monoglyceride 24.7

[0089] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E)).

Comparative Example

[0090] 271.7 g refined shea butter was reacted with 26.9 g glycerol in the presence of 1.5 g potassium hydroxide flakes at 200° C. and under vacuum lower than 100 mbar. When the reaction was completed, after approximatively 30 minutes, the product was bleached and deodorized in order to obtain a comparative example, which has the following composition (Table 7):

TABLE-US-00007 C8:0 0 C10:0 0 C12:0 0.4 C15:0 0 C14:0 0.2 C16:0 4 C16:1C 0.1 C16:1T 0 C17:0 0.1 C18:0 43.9 C18:1 43.3 C18:1T 0.1 C18:1C 43.2 C18:2 5.8 C18:2T 0.1 C18:2C 5.8 C18:3 0.2 C18:3T 0.1 C18:3C 0.1 Total Trans 0.2 C20:0 1.4 C20:1C 0.2 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0 Triglyceride 10.7 Diglyceride 48.3 Monoglyceride 40.2

[0091] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E))

Example 4

[0092] An emulsion stability test was performed in order to evaluate the functionality of emulsifiers. Besides the comparative example, a commercial emulsifier product Durem 35NG from IOI Loders Crokaan US was also included, which has the following composition (Table 8):

TABLE-US-00008 C8:0 0 C10:0 0 C12:0 0.3 C15:0 0.1 C14:0 1.1 C16:0 42.3 C16:1C 0.2 C16:1T 0 C17:0 0.1 C18:0 4.6 C18:1 41.1 C18:1T 0.1 C18:1C 41 C18:2 9.2 C18:2T 0.6 C18:2C 8.6 C18:3 0.2 C18:3T 0.1 C18:3C 0.1 Total Trans 0.8 C20:0 0.4 C20:1C 0.2 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0 Triglyceride 10.7 Diglyceride 48.3 Monoglyceride 40.2

[0093] In the above table:

Cx:y refers to a fatty acid having x carbon atoms and y double bonds;
C refers to cis fatty acids and T to trans fatty acids; levels determined by GC-FAME (ISO 12966-2 and ISO 12966-4);
Triglyceride/Diglyceride/Monoglyceride determined by HPLC (ISO 18395: 2005(E)).

[0094] 0.8 g emulsifier of Example 1, Example 3, Comparative example and Durem 35NG was totally dissolved in 80 g rapeseed oil respectively. Each mixture was put into a 120 ml glass bottle and mixed with a propeller with four symmetrical square blades of 0.8 cm each at a speed of 750 rpm. When the temperature of each mixture is at approximatively 30° C., 20 ml demineralized water was gently added into each mixture within 15 seconds. Each emulsion was further mixed at room temperature under the same mixing conditions for 1 minute. Then, each emulsion was poured into a 100 ml glass graduated cylinder at room temperature. After 30 min, the volume of water layer was read respectively in order to evaluate the emulsion stability. One control test was done without any emulsifier. The stability was calculated with the following formula:

[00001]$\mathrm{Emulsion}.Math..Math.\mathrm{stability}.Math..Math.\%=\frac{20-\mathrm{Volume}.Math..Math.\mathrm{of}.Math..Math.\mathrm{water}.Math..Math.\mathrm{layer}.Math..Math.\mathrm{after}.Math..Math.\mathrm{separation}}{20}.Math.\%$

[0095] The results are shown in the following table (Table 9):

TABLE-US-00009 Example Example Comparative Durem Control 1 3 example 35NG Volume of water 17 10 12 15 13 layer after separation (ml) Emulsion stability % 15% 50% 40% 25% 35%

[0096] Example 1 and Example 3 show better emulsion stability than the Comparative example and Durem 35NG.

Example 5

[0097] An emulsion stability test was performed in order to evaluate the functionality of the emulsifiers. A commercial emulsifier product Dimodan HP MB from Danisco, DuPont Group was included, which has the following composition (Table 10):

TABLE-US-00010 C8:0 0 C10:0 0 C12:0 0.3 C15:0 0.1 C14:0 1.2 C16:0 55.2 C16:1C 0 C16:1T 0 C17:0 0.1 C18:0 42.4 C18:1 0.1 C18:1T 0 C18:1C 0 C18:2 0 C18:2T 0 C18:2C 0 C18:3 0 C18:3T 0 C18:3C 0 Total Trans 0 C20:0 0.5 C20:1C 0 C20:2C 0 C22:0 0.1 C22:1 0 C22:1T 0 C22:1C 0 C24:0 0.1 C24:1C 0 Triglyceride 0.1 Diglyceride 2.5 Monoglyceride 97.1

[0098] 0.4 g emulsifier of either Example 2 or Dimodan HP MB were totally dissolved in 80 g rapeseed oil respectively. Each mixture was put into a 120 ml glass bottle and mixed with a propeller with four symmetrical square blades of 0.8 cm each at a speed of 750 rpm. When the temperature of each mixture is at approximatively 30° C., 20 ml demineralized water was gently added into each mixture within 15 seconds. Each emulsion was further mixed at room temperature under the same mixing conditions for 1 minute. Then, each emulsion was poured into a 100 ml glass graduated cylinder at room temperature. After 30 min, the volume of water layer was read respectively in order to evaluate the emulsion stability. One control test was done without any emulsifier. The stability was calculated with the following formula:

[00002]$\mathrm{Emulsion}.Math..Math.\mathrm{stability}.Math..Math.\%=\frac{20-\mathrm{Volume}.Math..Math.\mathrm{of}.Math..Math.\mathrm{water}.Math..Math.\mathrm{layer}.Math..Math.\mathrm{after}.Math..Math.\mathrm{separation}}{20}.Math.\%$

[0099] The results are shown in the following table (Table 11):

TABLE-US-00011 Control Example 2 Dimodan HP MB Volume of water layer 17 13 15 after separation (ml) Emulsion stability % 15% 35% 25%

[0100] Example 2 shows better emulsion stability than Dimodan HP MB.