Process for purifying sucrose fatty acid esters

• US 5,011,922 A
• Filed: 06/23/1989
• Issued: 04/30/1991
• Est. Priority Date: 06/27/1988
• Status: Expired due to Term

• Current Assignee: Dai-Ichi Kogyo Seiyaku Company Limited (DKS Co., Ltd.)
• Original Assignee: Dai-Ichi Kogyo Seiyaku Company Limited (DKS Co., Ltd.)
• Inventors: Nakajima, Akihiko, Matsumoto, Shusaku, Hatakawa, Yoshio
• Primary Examiner(s): Griffin, Ronald W.
• Assistant Examiner(s): White, Everett
• Application Number:
  US07/371,892
• Time in Patent Office: 676 Days
• Field of Search: 536/127, 536/124, 536/119, 536/115, 536/120
• US Class Current: 536/119
• CPC Class Codes: C07H 13/06 Fatty acids

Abstract

A process for purifying sucrose fatty acid esters included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst, which comprises adjusting the reaction mixture from which a part of the organic solvent as reaction medium may be previously removed and to which water is added to form an aqueous solution, to a neutral pH region, adding a neutral salt and sucrose to the solution to precipitate the sucrose fatty acid ester, filtering off the precipitate, and washing the precipitate with an acidic water. The washed precipitate in the form of slurry is spray-dried to form a dry powder, and the filtrate is contacted with a reverse osmosis membrane to recover sucrose. According to the invention, purified sucrose fatty acid esters can be obtained from the reaction mixture without using an organic solvent as purification solvent, while sucrose can be recovered in high yield.

Claims

1. A process for removing a volatile material from a reaction mixture in synthesis of a sucrose fatty acid ester by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent, said reaction mixture containing sucrose fatty acid ester, unreacted sucrose, unreacted fatty acid alkyl ester, a catalyst, a soap, a fatty acid and the organic solvent as a volatile material, which comprises adjusting the reaction mixture to a neutral pH region, adding water, a neutral salt and sucrose to the reaction mixture to transfer the volatile material into the aqueous phase with precipitation of the sucrose fatty acid ester, unreacted fatty acid alkyl ester, soap and fatty acid, and separating the resulting precipitate.

2. The process of claim 1, wherein said neutral region is from pH 6.2 to pH 8.2.

3. The process of claim 1, wherein after the addition of water, neutral salt and sucrose, the reaction mixture is heated to a temperature of 50°

to 80°

C.

4. The process of claim 1, wherein said water is added to the reaction mixture in a water/reaction mixture ratio of 5:

1 to 40;

1 by weight.

5. The process of claim 1, wherein the step of adding water, said neutral salt and sucrose further comprises adding the water, neutral salt and sucrose to the reaction mixture in amounts satisfying the following equations:

##EQU5## wherein x is the sum of the neutral salt to be added and a salt formed by neutralization of catalyst used in the synthesis of sucrose fatty acid ester, y is the total amount of water, and z is the sum of sucrose to be added and the unreacted sucrose present from the beginning.

6. The process of claim 1, wherein the pH adjustment of the reaction mixture is made with an acid selected from the group consisting of lactic acid, acetic acid, hydrochloric acid and sulfuric acid.

7. The process of claim 1, wherein said reaction mixture to be treated consists essentially of 15.0 to 92.0% by weight of a sucrose fatty acid ester, 1.0 to 80.0% by weight of unreacted sucrose, 0.5 to 10.0% by weight of unreacted fatty acid methyl ester, 0.05 to 7.0% by weight of a catalyst, 1.0 to 10.0% by weight of a soap, 0.5 to 10.0% by weight of a fatty acid and 5.0 to 30.0% by weight of a remaining reaction solvent.

8. The process of claim 1, wherein the fatty acid radical included in each of the fatty acid alkyl ester, soap and fatty acid is a saturated fatty acid radical having 16 to 22 carbon atoms.

9. The process of claim 1, wherein said volatile material is dimethylsulfoxide or dimethylformamide.

10. The process of claim 1, wherein said neutral salt to be added to the reaction mixture is a salt selected from the group consisting of sodium chloride, Glauber'"'"'s salt, potassium lactate and potassium acetate.

11. The process of claim 1, wherein said sucrose fatty acid ester is composed of 10 to 75% by weight of the monoester and 90 to 25% by weight of the di- and higher esters.

12. A process for purifying a sucrose fatty acid ester included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent, which comprises adjusting the reaction mixture to a neutral pH region, adding water, a neutral salt and sucrose to the reaction mixture to precipitate the sucrose fatty acid ester, separating the resulting precipitate from the liquid phase, and washing the precipitate with an acidic water.

13. The process of claim 12, wherein said neutral pH region is from pH 6.2 to pH 8.2.

14. The process of claim 12, wherein after the addition of water, neutral salt and sucrose, the reaction mixture is heated to a temperature of 50°

to 80°

C.

15. The process of claim 12, wherein said water is added to the reaction mixture in a water/reaction mixture ratio of 5:

1 to 40;

1 by weight.

16. The process of claim 12, wherein the step of adding water, said neutral salt and sucrose further comprises adding the water, neutral salt and sucrose to the reaction mixture in amounts satisfying the following equations:

##EQU6## wherein x is the sum of the neutral salt to be added and a salt formed by neutralization of catalyst used in the synthesis of sucrose fatty acid ester, y is the total amount of water, and z is the sum of sucrose to be added and the unreacted sucrose present from the beginning.

17. The process of claim 12, wherein said acidic water has a pH of 3.0 to 5.5.

18. The process of claim 12, wherein said acidic water is maintained at a temperature of 10°

to 40°

C.

19. The process of claim 12, wherein said precipitate washed with the acidic water is neutralized and spray-dried in the form of an aqueous slurry.

20. The process of claim 19, wherein said slurry has a solid content of 4 to 40% by weight and a water content of 96 to 60% by weight.

21. The process of claim 19, wherein said spray-drying is conducted in an air stream having an absolute humidity of 0.008 to 0.05 kg water/kg dry air and a temperature of 10°

to 100°

C.

22. The process of claim 12, wherein said liquid phase is brought into contact with a reverse osmosis membrane to recover sucrose.

23. The process of claim 22, wherein said reverse osmosis membrane has a fractionation molecular weight of 150 to 200.

24. The process of claim 22, wherein said liquid to be contacted with the membrane is maintained at a temperature of 40°

to 60°

C.

25. The process of claim 22, wherein said liquid to be contacted with the membrane is maintained at a pH of 6.2 to 8.2.