JPS6020389B2 - Separation method of tocopherols - Google Patents

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 crab extracts or deodorized crab extracts of vegetable oils have conventionally been used as raw materials for producing natural tocopherols.

In the process of separating tocopherols from these raw materials,
There are operations such as distillation and organic solvent treatment, 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 deodorized crab product of soybean oil, deodorized rice bran oil distillate, palm oil distillate fatty acids, 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 methylesterified, a food-grade antioxidant is added and the methylesterification is carried out 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 80% or more of the tocopherols in the raw material are contained in the concentrate as crab matter. The food-grade antioxidants used in the present invention include food-grade natural antioxidants such as ascorbic acid, lecithin, caffeic acid, ferulic acid ester, etc., and food-grade synthetic antioxidants such as butylhydroxyanisole, nordihydroguaia Examples include ticic acid. The amount of these antioxidants to be used has an appropriate amount depending on each type, but it is 2% or less, preferably 0.2% or less based on the weight of the bulk. When adding the food antioxidant of the present invention, the deterioration of tocopherols can be further prevented by using citric acid or phosphoric acid as a compensating agent.

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

Example 1 L-ascorbic acid 0.4 to palm oil distilled fatty acid lk9
In the evening, add 1.2 methanol containing 15 vol% of hydrochloric acid, stir at 500 to 6000 for 2 hours under a nitrogen stream,
The reaction product was washed with water, dehydrated, and filtered to obtain the methyl ester compound 1.
I got 1k9.

Then, this methylesterified product was distilled under reduced pressure (1.Mo
m) was carried out, and the methyl ester distilled out by 18 mm was removed by distillation.

Distillate 89.2%, residue 10.8%. 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, when the same treatment was performed without adding L-ascorbic acid, the concentration was only about 40%. Example 2 Rice bran oil deodorized crab extract (tocopherol concentration 1.
86%), 0.1% ascorbic acid was added, a 5.5% methanol solution of sodium hydroxide was added, and the mixture was heated for 15 minutes at room temperature 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 1.96%. This one again has 0.
Add 1% ascorbic acid, add a methanol solution of hydrochloric acid, and leave for 1 hour at 40°C under nitrogen flow. After adding ether and washing with water, the tocopherol concentration in the fatty acid methyl ester mixture obtained was 1.90%, and the recovery rate was 93.
It was 5%. Next, this product was distilled under reduced pressure below I Torr, yielding 56% of the residue.

The tocopherol concentration was 3.40%, and the recovery rate was 93.4% compared to the raw material rice bran oil deodorized crab extract. Example
3 Cannibal fatty acid lk obtained from palm oil deoxidation and deodorization process
After adding 0.1 g of ascorbic acid, 0.1 g of butylhydroxyanisole and 0.29 g of citric acid, methanol lk9 containing 2% concentrated sulfuric acid was added, and
I stirred the time.

Next, after washing with water and dehydration, Iton and crab matter of 180 qo or less were removed to obtain a residue of 55 qo. To this residue, add 0.3 parts of ascorbic acid and 50 parts of methanol, and add 60 parts of ascorbic acid.
qo, I stirred it for 10 minutes.

It was left at room temperature and the methanol fraction was separated. The same methanol treatment was repeated three times, and the methanol fraction was collected. For the methanol fraction, methanol was removed using a rotary evaporator to obtain a residue of 7.5 mm. The content of tocopherols in this residue was 3.4%, which corresponds to 85% of the tocopherol content in the raw fatty acid.

When no antioxidant was added in the above-mentioned tocopherol separation process, the tocopherol content in the residue was 40% of the tocopherol content in the raw fatty acid obtained after 2.4 days.

Example 1 Distillate 2k9 obtained in the deodorizing process of rice bran oil was mixed with 500' and 0.1 methanol containing 1% sodium hydroxide.
In the evening, the butylhydroxyanisole was heated at 60° C. for 1 hour, and unreacted methanol was distilled off.

The residue was washed with warm water. Next, 500 g of 2% sulfuric acid-methanol and 0.1 g of butylated hydroxyanisole were added to the residue and heated under reflux for 1 hour. After heating, excess methanol was removed using a rotary evaporator. After the residue was washed with water and dehydrated, crab fractions of 18 and 0 Torr were removed to obtain a residue of 1,050 Torr. Two volumes of methanol and 0.05 volumes of butylhydroxyanisole were added to this residue, and the mixture was stirred at 60 degrees for 1 minute.

Claims (1)

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