JPS59227876A - Separation of tocopherols - Google Patents

Abstract

PURPOSE:In extracting or concentrating tocopherol or tocotrienol from a natural substance such as deacidified distillate of vegetable oil, etc., to prevent deterioration caused by oxidation and polymerization of the desired compound, by adding and antioxidant for foods to the treatment system. CONSTITUTION:For example, in extracting or separating tocopherol or tocotrienol from a natural substance (deacidified distillate or deodorized distillate of vegetable oil) containing tocopherols, such as deacidified distillate of soybean oil or rice bran oil, or fatty acid distilled from palm oil, etc. by treatment such as methyl esterification, distillation, etc., referably <=0.2wt.% natural or synthetic antioxidant for food such as ascorbic acid, butylhydroxyanisole, etc. is added to the treatment system so that oxidation and polymerization of the desired compound are prevented. In the operation, the use of citric acid or phosphoric acid as a synergistic agent can prevent further the deterioration of the desired compound.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating tocopherols from deoxidized and deodorized distillates of vegetable oils.

Deoxidized distillates or deodorized distillates of vegetable oils have conventionally been used as raw materials for producing natural tocopherols. In the process of separating tocopherols from these raw materials, operations such as distillation and treatment with organic solvents are performed, during which oxidation, polymerization, decomposition, etc. of tocopherols occur, resulting in a decrease in their content. Therefore, there is a need for the development of a method for preventing a decrease in tocopherol content during the separation and concentration process of tocopherols.

The present invention relates to a method for separating tocopherols from a deodorized distillate of soybean oil, a deodorized rice bran oil distillate, a palm oil distillate fatty acid, etc. containing tocopherols while preventing oxidation and polymerization of the tocopherols.

In the present invention, when a deoxidized distillate or a deodorized distillate of vegetable oil is subjected to methyl esterification treatment, a food grade antioxidant is added and methyl esterification is performed by a conventional method. Next, when removing methyl ester by distillation, distillation is performed after adding a food grade antioxidant. Furthermore, after adding a food-grade antioxidant to the distillation residue in which tocopherols are concentrated, molecular distillation is performed, and as a distillate, 80% or more of the tocopherols in the raw material are contained in the concentrate.

The food-grade antioxidants used in the present invention include natural food-grade antioxidants such as ascorbic acid, lecithin, caffeic acid, fer/7-acid esters, etc., and food-grade synthetic antioxidants such as butylhydroxyanisole, Examples include nordihydroguaiaretic acid. The amount of these antioxidants to be used is determined depending on the situation, but the weight ratio should be less than 2%.

Next, the present invention will be explained in more detail with reference to Examples.

Example 1 1 kg of palm oil distilled fatty acid was added with 0.0.0 kg of L-ascorbic acid.
4g of hydrochloric acid, 15% of hydrochloric acid, 27% was added, and stirred at 500 to 60°C for 2 hours under a nitrogen stream.
The reaction product was washed with water, dehydrated, and passed through the mouth to obtain the methyl ester compound 1.
1 kg was obtained.

Then, this methyl ester product was distilled under reduced pressure (tOTo
rr) to remove the methyl ester distilled out up to 180°C. Distillate: 89.2 cm, residue: 1
0.8%. Approximately 80% of the tocopherols and tocotrienols contained in the raw palm oil distilled fatty acid were concentrated in this residue.

On the other hand, if the same treatment was performed without adding L-ascorbic acid, the concentration would be only about 40% (751).

Example 2゜Rice bran oil deodorized distillate (tocopherol concentration 1.86%)
To this, IO, 1% ascorbic acid is added, and a 5.5% methanol solution of sodium hydroxide is added, followed by stirring at room temperature for 15 minutes under a nitrogen stream. Next, the mixture is made acidic with a methanol solution of hydrochloric acid, and ether is added, followed by washing with water. The tocopherol concentration in the resulting fatty acid mixture was 196%. Add 0.1 thiascorbic acid to this again,
Add a methanol solution of hydrochloric acid and stir at 40°C for 1 hour under a nitrogen stream. After adding ether and washing with water, the tocopherol concentration in the fatty acid methyl ester mixture obtained was 1.
The recovery rate was 90% and 93.5%.

Next, this product was distilled under reduced pressure below 1'I'orr to obtain 56 residues. Tocopherol concentration is 3.
The recovery rate is 40%, which is 9% compared to the raw material rice bran oil deodorized distillate.
It was 3.4 chi.

Example 3 Distillate fat e obtained in palm oil deacidification and deodorization process]
, after adding 0.1 g of ascorbic acid, 0.1 g of butylated hydroxyanisole and 0.21 g of citric acid to
2 kg of methanol containing concentrated sulfuric acid was added, and 60
Stir at ℃ for 3 hours. Next, after washing with water and dehydrating, 1'p
The fraction below 180°C was removed to obtain 55 g of residue.

This residue contains 0.3 μ of ascorbic acid and 5 μm of methanol.
Qml was added and stirred at 60°C for 10 minutes.

It was left at room temperature and the methanol fraction was separated. The same nomethanol treatment was repeated three times, and the methanol fraction was collected. For the methanol fraction, methanol was distilled off using a rotary evaporator to obtain a residue of 7.51.

The content of tocopherols in this residue is 3.4 g, which is 85% of the tocopherol content in the distilled fatty acid as the raw material.
corresponds to

When no antioxidant was added in the above tocopherol separation process, the tocopherols in the residue were 2.4 g, which was 40 times the tocopherol content in the distilled fatty acid as the raw material.

Example 4 2 kg of distillate obtained in the deodorizing process of rice bran oil was mixed with 500 ml of methanol containing 1.
After heating at 60° C. for 1 hour, unreacted methanol was distilled off. The residue was washed with warm water. Next, 500 ml of dithiosulfuric acid-methanol and 017i (D-butylhydroxyanisole) were added to the residue and heated under reflux for 1 hour. After heating, excess methanol was distilled off using a rotary evaporator. The residue was washed with water, After dehydration, the fraction below 180° C. was removed to obtain 1.050 g of residue.

To this residue was added methanol 21 and 0.05 g of butylated hydroxyalsol, and the mixture was heated at 60°C for 10 minutes at 50°C.
0 all were added and left in a refrigerator at -20°C.

A liquid portion 143I was obtained from the generated crystals.

The amount of tocopherol in this oral fluid portion was 61.6 g, which was 88% of the amount of tocopherol in the raw material distillate.

Claims (1)

[Claims] (1) A method of adding a food grade antioxidant when extracting or concentrating tocopherols and tocotrienols from natural products.