JP2003160795A - Method for producing phytosterol/fatty acid ester- containing oil-and-fat composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for producing an oil-and-fat composition having a high content of phytosterols effective against absorption of cholesterols, resists to crystallization of the phytosterols and has a good taste. <P>SOLUTION: The method for producing a phytosterol/fatty acid ester- containing oil-and-fat composition comprises esterifying a mixture of phytosterols with oil-and-fat by using an alkali catalyst or a lipase powder catalyst in the presence of an adsorbent. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a plant sterol fatty acid ester-containing oil or fat composition having a cholesterol absorption inhibitory effect.

[0002]

2. Description of the Related Art Plant sterols have long been known to have an action of suppressing absorption of cholesterol from the small intestine, and have been used as plasma cholesterol level lowering agents. Cholesterol absorption requires that cholesterol be dissolved in bile acid micelles. However, the amount of cholesterol dissolved in bile acids is low, and most of them are in an emulsion state.

On the other hand, in the case of plant sterols, almost the same amount as cholesterol is dissolved in bile acid micelles. Therefore, when cholesterol and phytosterol coexist, the amount of cholesterol dissolved in bile acid micelles decreases. Further, the absorption rate of plant sterols from the small intestine is low and remains in the lumen of the small intestine, so the amount of cholesterol dissolved in the bile acid micelles remains limited, and the absorption of cholesterol is suppressed. Therefore, plant sterols have been clinically utilized as effective plasma cholesterol level lowering agents in humans who are susceptible to cholesterol ingested from the diet.

This plant sterol contains vegetable oils and fats, soybeans,
It is contained in wheat, etc., and is consumed in daily meals.
Its quantity is negligible. In order to suppress the absorption of cholesterol, about 1 to 2 g of plant sterol is required per day, and it is difficult to take such a large amount of plant sterol in a normal human diet.

Recently, in order to utilize plant sterols in fats and oils products, many methods for improving solubility in fats and oils have been proposed. JP-B-57-26732 proposes a method of increasing the solubility of plant sterols in fats and oils by increasing the content of free fatty acids in the fats and oils. According to this method, the solubility of plant sterols in oils and fats is improved, but the free fatty acid content in the oils and fats is high, and it is difficult to commercialize it as it is.

JP-A-59-147099 discloses a method of adding deodorizing scum to edible oil and fat and refining it to increase the phytosterol content in the oil and fat.
In Japanese Patent No. 736, the oil and fat compositions obtained by extracting plant sterols from an edible oil and fat with an organic solvent and adding the sterols are proposed, but the phytosterols in the oil and fat compositions prepared by these methods have been proposed. The content is very low and not satisfactory.

JP-A-57-206336 proposes an edible oil / fat containing 0.5 to 30% by weight of plant sterol. Since the solubility of plant sterols in fats and oils is low, merely mixing plant sterols in fats and oils does not improve the solubility in fats and oils. As described above, a method for producing an oil / fat composition having a high content without crystallization of plant sterol at room temperature has not been found at present.

On the other hand, there is also a method in which a plant sterol is converted to a plant sterol fatty acid ester to enhance the solubility in oil and fat. Since plant sterol fatty acid ester is hydrolyzed into free plant sterol and fatty acid in the small intestine, it has a cholesterol absorption inhibitory action like plant sterol.

Japanese Unexamined Patent Publication (Kokai) No. 62-166895 discloses an esterification reaction of a fatty acid or a fatty acid ester with a plant sterol using a lipase as a catalyst in an aqueous medium system and / or an aqueous organic solvent system. Since the reaction uses a solvent, a desolvation step is required, and since the reaction is carried out in a water-containing solvent system, the resulting oil and fat composition has a high acid value. In JP-A-2000-72793, stanol / sterol and fatty acid are directly esterified in the presence of a color deactivator, but the purpose of using the color deactivator in this method is to improve the color tone. is there.

Further, plant sterols are generally produced from the deodorizing scum of fats and oils, and their flavor cannot be said to be good. For this reason, if a large amount of plant sterol is added, the flavor will naturally deteriorate. In the prior art, although there have been many proposals for increasing the content of plant sterols in fats and oils, none of them describes the flavor of refined oils.

Therefore, an object of the present invention is to provide a method for producing an oil / fat composition having a high content of plant sterols having a cholesterol absorption inhibitory effect, preventing the plant sterols from precipitating as crystals and having a good flavor. To do.

[0012]

Means for Solving the Problems The present invention comprises a plant sterol fatty acid ester-containing fat or oil characterized by subjecting a mixture of plant sterol and fat or oil to an esterification reaction using an alkali catalyst or a lipase powder catalyst in the presence of an adsorbent. The above object is achieved by a method for producing a composition.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The method for producing the plant sterol fatty acid ester-containing oil / fat composition of the present invention will be described in detail below. The plant sterol used in the present invention is contained in the unsaponifiable matter of seed oil such as soybean, rapeseed and cottonseed, and is obtained by being separated from the deodorizing scum mainly produced in the deodorizing step of vegetable oil. is there.

The plant sterols are generally β-sitosterol, stigmasterol, campesterol,
Brush casterol and the like are known. The plant sterol used in the present invention does not need to be an isolated product thereof, but a mixture of the above sterols is sufficient. Also,
The plant sterol used in the present invention may contain stanol obtained by hydrogenating the above sterol.

The oil and fat used in the present invention is an oil and fat having a fatty acid composition of a saturated fatty acid or an unsaturated fatty acid having 4 to 24 carbon atoms, specifically palm oil, palm olein,
Liquid oils such as super olein, palm stearin, palm oils and fats such as palm mid-melting point, soybean oil, rapeseed oil, high oleic rapeseed oil, cottonseed oil, safflower oil, olive oil, sunflower oil, high oleic sunflower oil, rice bran oil, etc., Laurin oils and fats such as palm kernel oil and coconut oil, animal fats and oils such as beef tallow, lard, fish oil and milk fat, hardened oils of these fats and oils,
Fractionated oil or transesterified oil can be used alone or in combination. However, from the viewpoint of health, it is preferable to use vegetable oils and fats.

In the present invention, the mixing ratio of plant sterols and oils and fats is preferably such that the number of moles of plant sterols is less than or equal to the number of moles of fatty acid residues of oils and fats. When using a fat and oil having a group, preferably 99 to 45% by weight of the fat and oil and 1 to 55% by weight of the plant sterol, and more preferably 95 to 5% of the fat and oil.
0% by weight and 5 to 50% by weight of plant sterols, most preferably 90 to 50% by weight of oil and fat and 10% of plant sterols.
A mixture of up to 50% by weight is used. In the above case, when the blending amount of the plant sterol is more than 55% by weight, unreacted plant sterol is liable to remain and melting in the mouth is likely to be worse. Further, in the above case, if the compounding amount of the plant sterol is less than 1% by weight, the cholesterol absorption suppressing effect is difficult to be exhibited.

Examples of the adsorbent used in the present invention include activated clay, silica, activated carbon, cellulose, starch, celite or ion exchange resin, and one or more selected from these are used. it can. In the present invention, it is preferable to use activated clay.

The amount of the adsorbent to be added varies depending on the amount of the oil or fat used in the present invention, but is preferably 0.01 to 20% by weight, more preferably 100% by weight, based on the mixture of the plant sterol and the oil or fat. Is 0.1 to 10% by weight, most preferably 0.1 to 1% by weight. If the amount of the adsorbent added is less than 0.01% by weight, the effect of promoting the esterification reaction is small, and a large amount of free plant sterol having a high melting point tends to remain. If the amount of adsorbent added exceeds 20% by weight, the reaction oil obtained by the esterification reaction of plant sterols and fats and oils tends to soak into the adsorbent, and the adsorbent tends to be absorbed after the esterification reaction. Since it is filtered off, the loss of reaction oil tends to increase.

The catalyst used in the esterification reaction according to the present invention is an alkali catalyst or a lipase powder catalyst. Specific examples of the alkali catalyst include sodium methoxide and caustic soda.

The above-mentioned alkali catalyst is added in an amount of 0.01 to 5% by weight with respect to the mixture of plant sterol and oil and fat.
It is preferably 0.1 to 1% by weight, and most preferably 0.2 to 0.5% by weight. When the amount of the alkali catalyst added is less than 0.01% by weight, the esterification reaction is unlikely to proceed. When the amount of the alkali catalyst added exceeds 5% by weight, as a by-product,
Since soap, fatty acid methyl ester, etc. are produced, the loss of reaction oil is likely to increase.

Specific examples of the above-mentioned lipase powder catalyst include Alcaligenes, Chromobacterium and Pseudomonas.
Genus, lipases obtained from the genus Humicola are preferred, Alca
Most preferred are lipases from the genera Ligenes and Pseudomonas. When these enzymes are immobilized on a carrier such as diatomaceous earth, alumina, ion-exchange resin, activated carbon, or ceramic, the effect of promoting esterification is reduced, so that they are used as lipase powder as they are. Further, the immobilized lipase is not used in the present invention.

The above lipase powder catalyst is added in an amount of 0.01 to 10 relative to the mixture of plant sterol and fats and oils.
It is preferable to set it as a weight% and more preferably 0.05
.About.5% by weight, most preferably 0.1 to 1% by weight.

The esterification reaction according to the present invention is preferably carried out in the absence of solvent.

The reaction temperature of the esterification reaction according to the present invention is preferably 70 ° C. or higher when an alkali catalyst is used.
130 ° C., more preferably 80 ° C. to 120 ° C., most preferably 90 ° C. to 110 ° C. When the reaction temperature is lower than 70 ° C, the reaction is difficult to occur completely, and when higher than 130 ° C, the flavor of the plant sterol fatty acid ester-containing oil / fat composition is likely to be deteriorated.

When using a lipase powder catalyst, the reaction temperature is preferably 60 ° C to 90 ° C, more preferably 65 ° C to 85 ° C, most preferably 70 ° C to 80 ° C. When the reaction temperature is lower than 60 ° C, the plant sterol does not dissolve, so the reaction is slow, and when it is higher than 90 ° C, the lipase is easily deactivated.

The water content of the system in which an adsorbent is added to a mixture of plant sterols and oils and fats is preferably 100 ppm or less, more preferably 5 when an alkali catalyst is used.
It is preferably 0 ppm or less to prevent deactivation of the catalyst.

When the lipase powder catalyst is used, the water content is preferably 900 ppm or less, more preferably 500 ppm or less, because the hydrolysis of the reaction oil can be minimized and the loss in the deodorizing step can be reduced. desirable.

The esterification reaction can be carried out under normal pressure or reduced pressure.

The esterification reaction of the present invention can be carried out by a batch type batch reaction. In a batch-type batch reaction, it is preferable to mix plant sterols, fats and oils and an adsorbent, and perform dehydration under reduced pressure. The conditions for reducing the pressure at this time are preferably 500 to 2000 Pa,
More preferably, it is 500-1500 Pa.

Then, 30 minutes to 3 hours when an alkali catalyst is used, and 4 minutes when a lipase powder catalyst is used.
It is preferable to carry out the esterification reaction for 48 hours. At this time, the above esterification reaction is preferably carried out under reduced pressure. The conditions for reducing the pressure at this time are preferably 500 to 2000 Pa, more preferably 500 to 15 Pa.
It is 00 Pa.

Further, using a lipase powder catalyst, the reaction temperature was set to 90 ° C. or lower, and 30% by weight of plant sterol was used.
When compounded above, because the plant sterol does not dissolve,
The esterification reaction is carried out in two or three stages (for example, first, a part of the plant sterol is blended and the first stage reaction is carried out,
After the reaction of the first step is completed, the remaining plant sterols are added to carry out the reaction of the second step).

The reaction oil obtained by the esterification reaction of a mixture of plant sterols and oils and fats with an alkali catalyst or a lipase powder catalyst in the presence of an adsorbent is usually a medium oil when an alkali catalyst is used. When the lipase powder catalyst is used by filtering the adsorbent, washing with water, bleaching, and deodorizing, purification is performed by filtering, bleaching, and deodorizing the lipase powder and the adsorbent.

The above neutralization step is performed by adding an aqueous phosphoric acid solution or an aqueous citric acid solution. At this time, the alkali catalyst used in the esterification reaction is neutralized and decomposed.

The step of filtering the adsorbent is carried out by vacuum filtration or squeeze filtration using Celite as a filter aid.

The bleaching step is carried out by treating with an adsorbent such as activated clay, silica or activated carbon. Further, the bleaching step is preferably 70 to 90 ° C. and 500 to 150.
It is performed under a reduced pressure of 0 Pa for 15 to 30 minutes.

Although the usual deodorizing step is carried out at a high temperature such as 250 to 265 ° C., the above deodorizing step according to the present invention is
It is preferably 250 ° C or lower, particularly preferably 120 to 24
Perform at 0 ° C. When the deodorization temperature is higher than 250 ° C, the loss of the produced plant sterol fatty acid ester tends to increase. Moreover, the deodorizing step is preferably 100 to 400 Pa.
It is better to carry out under reduced pressure.

The deodorizing time varies depending on the deodorizing temperature and the acid value of the reaction oil, but is usually 30 to 180 minutes.

The above washing step is preferably carried out by adding about 50% by weight or less of water to the obtained reaction oil.

As described above, an oil and fat composition having a high plant sterol fatty acid ester content can be obtained by subjecting a mixture of plant sterol and oil and fat to an esterification reaction using an alkali catalyst or a lipase powder catalyst in the presence of an adsorbent. it can. The mechanism of this reaction is as follows.

When a mixture of plant sterols and fats and oils is subjected to an esterification reaction using an alkali catalyst or a lipase powder catalyst without using an adsorbent, plant sterol fatty acid esters, plant sterols, triglycerides, diglycerides, monoglycerides, A reaction oil consisting of glycerin is obtained.

On the other hand, when a mixture of plant sterol and oil is subjected to an esterification reaction in the presence of an adsorbent using an alkali catalyst or a lipase powder catalyst, the reaction equilibrium is obtained by adsorbing monoglyceride and glycerin to the adsorbent. Shift, plant sterol fatty acid esters increase, plant sterols, triglycerides, diglycerides, monoglycerides decrease, and glycerin is newly produced. If the alkali catalyst or the lipase powder catalyst and the adsorbent are present in a sufficient amount, the above reaction is repeated, and the reaction shifts to a reaction in which a plant sterol fatty acid ester is produced, whereby a fat and oil composition having a high plant sterol fatty acid ester content can be obtained. You can do it.

The present invention is characterized in that the esterification rate is increased by adsorbing the monoglyceride and glycerin produced by the adsorbent in the esterification reaction of plant sterol with fats and oils. It is different from the esterification method. In addition, the production method of the present invention is advantageous in terms of cost, as compared to the method using a fatty acid or a fatty acid ester, inexpensive oils and fats are used as they are for reducing the supply of fatty acids.

The production rate of the plant sterol fatty acid ester by the esterification reaction according to the present invention is preferably 80 to
100%, more preferably 90 to 100%.
The production rate of the plant sterol fatty acid ester mentioned here is a value obtained by the following formula.

Production rate of plant sterol fatty acid ester (%) = (A / B) × 100 A: Plant sterol fatty acid ester in plant sterol fatty acid ester-containing oil / fat composition converted to plant sterol (% by weight) = plant sterol fatty acid Ester content x 41
4 / (414 + 282-18) B: Total plant sterol conversion amount (% by weight) in plant sterol fatty acid ester-containing oil / fat composition = A + plant sterol content

The constituent fatty acids of the plant sterol fatty acid ester contained in the plant sterol fatty acid ester-containing oil and fat composition obtained by the production method of the present invention differ depending on the fatty acid composition of the reacting oil and fat, but have 4 to 24 carbon atoms. Of saturated or unsaturated fatty acids.

The plant sterol fatty acid ester-containing oil / fat composition obtained by the production method of the present invention preferably contains the plant sterol fatty acid ester in an amount of 5% by weight or more, more preferably 10 to 95% by weight, and further preferably 20 to 95% by weight. %, Most preferably 30 to 90% by weight.

The plant sterol fatty acid ester-containing oil / fat composition obtained by the production method of the present invention preferably contains plant sterols in an amount of 5% by weight or less, more preferably 0.1% by weight or more and 4.5% by weight or less, and most preferably. Is 0.1% by weight
The above content is 4% by weight or less.

The plant sterol fatty acid ester-containing oil / fat composition obtained by the production method of the present invention preferably contains triglyceride in an amount of 0.1 to 95% by weight, more preferably 0.
5 to 70% by weight, most preferably 1 to 50% by weight, diglyceride is preferably 0.1 to 25% by weight, more preferably 0.5 to 20% by weight, most preferably 1
˜15% by weight.

The plant sterol fatty acid ester-containing oil / fat composition obtained by the production method of the present invention may be used alone or in a mixture with other edible oil / fat, for shortening, margarine, and kneading for confectionery, baking, and pastry. Oils and fats for inclusion, oils and fats for roll-in, oils and fats for whipped cream, oils and fats for mayonnaise, oils and fats for chocolate, oils and fats for anhydrous cream, oils and fats for cooking, oils and fats for frying, oils and fats for spraying, and the like. When used by mixing with other edible oils and fats, the blending amount of the plant sterol fatty acid ester-containing oil and fat composition obtained by the production method of the present invention is preferably 1 to 99% by weight, more preferably 5 to 5% by weight in the mixed oils and fats. 90% by weight, most preferably 10 to 80% by weight. And using the fats and oils as described above, bread, sweet buns, pies, Danish, chows, donuts, cakes, crackers, cookies, biscuits, waffles, scones, snacks, whipped cream, milk substitute compositions, desserts, ice cream, Foods such as beverages, mayonnaise, dressings, chocolate, anhydrous cream, candies, gums, rice crackers, sand creams, filling creams, salads, retort foods, roux, fried foods, and frozen foods can be produced.

[0050]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. In the following examples, the number of moles of each component in the raw fat and oil was calculated using the following molecular weights. Further, rapeseed oil is an oil and fat mainly having a fatty acid residue having 16 to 18 carbon atoms.

[0051] Rapeseed oil triglyceride: MW884 Plant sterol: MW414 Rapeseed oil fatty acid residue (average): MW264

(Example 1) 350 g (0.85 mol) of plant sterol and 650 g of rapeseed oil were placed in a 2 liter flask.
(Mole number of rapeseed oil triglyceride: 0.74 mol, number of moles of rapeseed oil fatty acid residue: 2.21 mol), 1 g of activated clay was added, and the temperature was 105 ° C. and the pressure was reduced to 1,330 Pa or less under pressure of 30.
The mixture was stirred for a minute so that the water content was 50 ppm or less. Then, 2 g of sodium methoxide was added to this, and the temperature was 100 ° C.
The esterification reaction was performed for 30 minutes under a reduced pressure of 1,330 Pa or less. Neutralize reaction oil by conventional method, filter adsorbent, wash with water,
Bleaching (at a temperature of 85 ° C., 1% by weight of clay was added to the reaction product, and treated under reduced pressure of 1,330 Pa or less for 30 minutes),
Deodorization (steam distillation was performed under a reduced pressure of 200 ° C. and 399 Pa or less for 60 minutes) to obtain a reaction refined oil (plant sterol fatty acid ester-containing oil / fat composition). The reaction refined oil obtained was a liquid oil and had a good flavor. The composition of the obtained reaction refined oil is shown in Table 1.

Comparative Example 1 A reaction refined oil was obtained in the same manner as in Example 1 except that activated clay was not added during the esterification reaction. The obtained reaction refined oil had a large amount of free phytosterols having a high melting point and remained poorly melted in the mouth. Also,
The composition of the obtained reaction refined oil is shown in Table 1.

Example 2 500 g (1.21 mol) of plant sterols and 500 g of rapeseed oil in a 2 liter flask.
(Rapeseed oil triglyceride mol number: 0.57 mol, rapeseed oil fatty acid residue mol number: 1.71 mol) and 5 g of silica gel were put, and the temperature was 110 ° C., and the pressure was reduced to 1,330 Pa or less under pressure.
The mixture was stirred for 0 minutes to reduce the water content to 50 ppm or less. 5 g of sodium methoxide was added thereto, and the temperature was 105 ° C. and 1,33
The esterification reaction was performed for 30 minutes under reduced pressure of 0 Pa or less. The reaction oil is neutralized by a conventional method, the adsorbent is filtered off, washed with water, and bleached (at a temperature of 85 ° C., 1% by weight of clay is added to the reaction product and treated for 30 minutes under a reduced pressure of 1,330 Pa or less), Deodorization (steam distillation was performed under a reduced pressure of 200 ° C. and 399 Pa or less for 60 minutes) to obtain a reaction refined oil. The reaction refined oil obtained was a liquid oil and had a good flavor. Also,
The composition of the obtained reaction refined oil is shown in Table 1.

Comparative Example 2 A reaction refined oil was obtained in the same manner as in Example 2 except that silica gel was not added during the esterification reaction. The obtained reaction refined oil had a large amount of free phytosterols having a high melting point and remained poorly melted in the mouth. The composition of the obtained reaction refined oil is shown in Table 1.

(Example 3) 200 g (0.49 mol) of plant sterol and 600 g of rapeseed oil were placed in a 2 liter flask.
(Mole number of rapeseed oil triglyceride: 0.68 mol, mole number of rapeseed oil fatty acid residue: 2.04 mol) and 3 g of activated carbon were added, and the temperature was 100 ° C. and the pressure was reduced under a pressure of 1,330 Pa or less to 15
The mixture was stirred for a minute, and the water content was adjusted to 300 ppm. The temperature was lowered to 70 ° C, and a commercially available powdered lipase (trade name: Lipase QL (Al
caligenes genus), manufactured by Meito Sangyo Co., Ltd.) (3 g), and the esterification reaction was carried out for 24 hours under a nitrogen atmosphere. Further, 200 g (0.49 mol) of plant sterol was added thereto, and the esterification reaction was carried out for 24 hours under a reduced pressure of 1,330 Pa or less. The reaction oil is filtered, the lipase and the adsorbent are filtered off, and bleached (at a temperature of 85 ° C., 1% by weight of clay is added to the reaction product, and treated under reduced pressure of 1,330 Pa or less for 30 minutes), deodorization (temperature Steam distillation was carried out at 200 ° C. under reduced pressure of 399 Pa or less for 60 minutes) to obtain a reaction refined oil.
The reaction refined oil obtained was a liquid oil and had a good flavor. The composition of the obtained reaction refined oil is shown in Table 1.

Comparative Example 3 Immobilized lipase commercially available as lipase (trade name: Lipase QLC (Alcaligenes)
Genus), manufactured by Meito Sangyo Co., Ltd., except that Example 3 was used.
A reaction refined oil was obtained in the same manner as in. The obtained reaction refined oil had a large amount of free phytosterols having a high melting point and remained poorly melted in the mouth. The composition of the obtained reaction refined oil is shown in Table 1.

[0058]

[Table 1]

From Table 1, when an adsorbent is used in the esterification reaction of a mixture of plant sterols and oils and fats with an alkali catalyst or a lipase powder as a catalyst, the content of plant sterol fatty acid ester is high and the content of plant sterols is high. It is understood that it is possible to produce an oil and fat composition having a low

(Example 4) Preparation of margarine 20% by weight of hardened soybean oil (melting point: 45 ° C), 15% by weight of palm oil, 50% by weight of reaction refined oil of Example 1, 13.3% by weight of water, 1% by weight of salt %, Skim milk powder 0.5% by weight and flavor 0.2% by weight were emulsified and rapidly plasticized to prepare margarine. This margarine contained 36% by weight of plant sterol fatty acid ester and 0.6% by weight of free plant sterol. The obtained margarine did not contain an emulsifier, but did not separate water during both the rapid plasticization and the storage (4 months). In addition, the flavor was very good because no emulsifier was added. Also,
The obtained margarine was measured according to the standard oil and fat analysis method (Japan Oil Chemistry Association) 2.4.9.1-1996 (thin layer chromatograph-gas chromatograph method), and plant sterols (free form conversion) Of 22.6% by weight.

[0061]

Industrial Applicability The present invention provides a method for producing an oil and fat composition containing plant sterols and oils and fats as raw materials and containing a high concentration of a plant sterol fatty acid ester having a cholesterol absorption inhibitory effect.

[Procedure amendment]

[Submission date] November 28, 2001 (2001.11.
28)

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be amended] Claims

[Correction method] Change

[Correction content]

[Claims]

[Procedure Amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0017

[Correction method] Change

[Correction content]

The adsorbent used in the present invention includes activated clay, silica, activated carbon, cellulose, starch and celite.
And ion exchange resins and the like, and one or more selected from these can be used. In the present invention, it is preferable to use activated clay.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Maruzen Shoji             7-35 Higashiokyu, Arakawa-ku, Tokyo Asahiden             Chemical Industry Co., Ltd. F-term (reference) 4B026 DC05 DH01 DL05                 4H059 AA06 AA11 AA12 AA13 BA14                       BB57 BC48 CA21 CA32 CA35                       CA39 CA48 EA17

Claims (3)

[Claims] 1. A method for producing a plant sterol fatty acid ester-containing oil or fat composition, which comprises subjecting a mixture of plant sterol and oil or fat to an esterification reaction in the presence of an adsorbent using an alkali catalyst or a lipase powder catalyst. 2. The plant sterol fatty acid ester-containing product according to claim 1, wherein the adsorbent is one or more selected from activated clay, silica, activated carbon, cellulose, starch, celite or ion exchange resins. Method for producing oil and fat composition. 3. The plant sterol fatty acid ester-containing oil or fat composition comprises 5% by weight of plant sterol fatty acid ester.
The method for producing an oil and fat composition containing a plant sterol fatty acid ester according to claim 1 or 2, which comprises the above.