JP2000212590A - Production of modified oil and fat and modified oil and fat - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing oils and fats having excellent processability by a transesterification and to obtain processed oils and fats such as margarine/shortening, etc., using the oils and fats and a processed product containing the modified oils and fats and/or the processed oils and fats in methods for modifying oils and fats. SOLUTION: This method comprises transesterifying an oil and fat mixture comprising 4-40% of lauric acid and 20-80% of >=16C saturated fatty acid so as to give 5-75% randomization ratio. The ratio of numerical value of the randomization to the transesterification ratio is 0.05-0.75. The transesterification is preferably carried out by an enzyme having low position selectivity.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for modifying fats and oils by transesterification, and relates to a method for producing modified fats and oils having good processing suitability, processed fats and oils such as margarine and shortening using the modified fats and oils, and The present invention relates to a processed product containing the modified fat or oil and / or the processed fat or oil.

[0002]

2. Description of the Related Art Margarine shortening (hereinafter referred to as M
/ S) may be prepared by mixing a hard fat and a liquid fat to maintain appropriate plasticity at the temperature used. As a raw material of hard fats and oils, hardened oils such as soybean oil, corn oil, rapeseed oil and the like, lard and palm-based fats and oils are often used,
For hardened vegetable oils, the change in the chain length of the constituent fatty acids is poor, and for lard and palm oil, there is the formation of coarse crystals due to the symmetric triglyceride,
In addition to roughening of the tissue, there is a disadvantage that the liquid oil cannot be retained in the structure formed by the hard oil and fat, and the liquid oil easily oozes due to a change in environment.

[0003] In order to overcome such drawbacks, as a method of producing fats and oils suitable for margarine shortening, for example, a method of randomly transesterifying a palm fat and a laurin fat with a chemical catalyst (Japanese Patent Publication No. 58-53894). Is disclosed. According to the disclosed method, the structure of a symmetric triglyceride of palm oil is eliminated by random transesterification with lauric fats and oils having different chain lengths, and a solidification rate suitable for M / S processing is obtained. The property of hardening is improved to some extent. However, conversely, an increase in trisaturated triglycerides is unavoidable, and there is a difficulty in melting in the mouth, and the effect of completely suppressing coarse crystals has not been obtained.

[0004] On the other hand, a method of reforming by transesterification using a lipase having a reaction selectivity for the 1,3-position of the glyceride skeleton of fats and oils (JP-A-61-950)
No. 98). According to this method, 3
Although the increase in saturated triglyceride can be suppressed, the structure of symmetrical triglyceride in palm oil is not effectively eliminated, and there is a risk that the quality will change over time, that is, the quality will deteriorate after storage for a certain period of time. And so on, a sufficient reforming effect cannot be obtained as a raw material fat.

[0005]

In view of such circumstances, the present invention adjusts the randomization rate in transesterification to eliminate the drawbacks of the conventional random transesterification and the esterification by lipase having 1,3-position specificity. Simultaneous resolution of the disadvantages of replacement, ie, improvement in processability of processed oils such as M / S by improving spreadability, creaming properties, and solidification speed, suppression of deterioration of tissue over time, processing of baked confectionery, etc. The purpose is to suppress migration of fats and oils in products.

[0006]

SUMMARY OF THE INVENTION According to the present invention, in transesterifying a fat or oil mixture containing lauric acid and a saturated fatty acid having 16 or more carbon atoms, the physical properties of the fat or oil are improved by adjusting the randomization rate. And completed the present invention. That is, the present invention relates to lauric acid of 4 to
A modified fat and oil production method comprising transesterifying a fat and oil mixture containing 40% and 20 to 80% of a saturated fatty acid having 16 or more carbon atoms so that the randomization ratio becomes 5 to 75%. The present invention relates to a high quality oil and fat, a processed oil and fat containing the modified oil and fat, and a processed product containing the modified oil and / or processed oil and fat. It is preferable that the ratio of the numerical values of the randomization rate and the transesterification rate is 0.05 to 0.75. Further, the randomization rate is preferably 10 to 70%, preferably the lauric acid content of the fat or oil mixture is 4 to 20%, preferably the content of the saturated fatty acid having 16 or more carbon atoms in the fat or oil mixture is 25 to 70%.
%, And preferably the transesterification is performed by an enzyme with low regioselectivity.

[0007]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
The present invention relates to a method for producing an oil or fat whose physical properties have been modified by adjusting a randomization rate, for transesterifying an oil or fat mixture containing lauric acid and a saturated fatty acid having 16 or more carbon atoms, The present invention relates to a processed fat or oil containing the modified fat or oil and a processed product containing the modified fat or oil and / or the processed fat or oil.

[0008] Lauric acid is a saturated fatty acid having 12 carbon atoms and is also called dodecaic acid. The C16 or higher saturated fatty acids include, for example, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, melisic acid and the like.

The fat or oil mixture comprises one or more kinds of fats and oils, and contains the above-mentioned lauric acid and a saturated fatty acid having 16 or more carbon atoms, and has a lauric acid content of 4 to 4.
40%, preferably 4-20%, more preferably 4-9
%, And the content of saturated fatty acids having 16 or more carbon atoms is 20 to
80%, preferably 25-70%, more preferably 30%
〜60%.

[0010] The fats and oils of the lauric acid source include lauric fats, such as palm kernel oil, coconut oil, babassu oil, and tsumum oil.
In addition, fats and oils obtained by separating, hardening and the like can be used.
As fats and oils of a saturated fatty acid source having 16 or more carbon atoms, palm oil, peanut oil, cottonseed oil, rice bran oil, chicken oil, lard, milk fat, beef tallow, and the like, or fats and oils obtained by fractionation and hardening thereof can be used.

In addition, soybean oil, rapeseed oil, rapeseed oil with high oleic acid, corn oil, safflower oil, safflower oil with high oleic acid, sunflower oil, high olein as long as the content of the lauric acid and the saturated fatty acid having 16 or more carbon atoms is satisfied. Acid sunflower oil,
Olive oil, perilla oil, perilla oil, linseed oil, linseed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, camellia oil, teaseed oil, borage oil, wheat germ oil, algae oil, fish oil, egg oil, etc. Liquid oils and their hardened oils can be used. From a nutritional point of view, the hardened oil is preferably low in trans acid.

[0012] Transesterification refers to an exchange reaction of a fatty acid substrate carried out between two or more kinds of fats and oils. Catalysts for this reaction include chemical catalysts such as alkali metals and their hydroxides and alcoholates, and microbial enzyme lipases that are enzyme catalysts. The transesterification includes random transesterification for randomizing the fatty acid sequence, direct transesterification having directivity, and selective transesterification having regioselectivity of triglycerides.

In the case of transesterification using a chemical catalyst, random transesterification is performed, and the fatty acid sequence is randomized. When this reaction is partially crystallized at a low temperature to precipitate a saturated fatty acid triglyceride and directs the reaction to two components with an unsaturated triglyceride that does not crystallize, direct transesterification occurs. Also in this case, the fatty acid sequence is random. When using a chemical catalyst, the randomization rate cannot be adjusted. This is so-called complete random transesterification. Chemical catalysts include alkali metals, their hydroxides, and alcoholates. In Japan, only sodium hydroxide and sodium methylate are permitted to be used.

Transesterification using an enzyme catalyst includes random transesterification and selective transesterification. For selective transesterification, the position of the triglyceride (1,3
Position), fatty acid type,
There is a reaction to select a partial glyceride (mono, diglyceride). Although an enzyme having low regioselectivity is used in the present invention, an enzyme having low regioselectivity includes an enzyme having no regioselectivity, an enzyme having relatively low regioselectivity, an enzyme having no regioselectivity and regioselectivity. , Or a mixture of enzymes having a low regioselectivity and enzymes having regioselectivity. Specifically, the 1,3 selectivity coefficient is 0.1
An enzyme, preferably a 1,3 selection coefficient of 0.2 to
It is preferable to use an enzyme having a 1,3 selection coefficient of 0.3 to 1, more preferably 1. The 1,3 selection coefficient is defined as the case where the transesterification of the 1,3-position specific fatty acid into the 2-position is performed when the transesterification of the 1,3-position fatty acid reaches 100%. Is expressed as 1. These can be used in a state of low molecular weight to high molecular weight, which are acidic, neutral or alkaline, and can be used in the form of powder or immobilized by a known method.

The term "enzyme catalyst" refers to an enzyme lipase derived from a microorganism. Among these, microorganisms which produce the enzyme used in the present invention as an enzyme having no or relatively low regioselectivity include: Aandida SP. , Chromo
bacteriumu SP., HumicoraSP., Penicillium SP., Cadid
a SP., Chromobacterium SP., Corynebactterium SP., Ge
otrichum SP., pseudomnas SP., Ryzopus SP., Penicil
liu SP., Staphylococcus SP., Alcaligenes SP. Regarding the transesterification reaction, the use of a microorganism-derived enzyme lipase is preferable to the use of a chemical catalyst from the viewpoint of safety for living organisms and the like.

In the present invention, the randomization ratio is defined as the difference between the specific fatty acid content at two positions in the fat / oil mixture before transesterification and the specific fatty acid content in the total fatty acid composition as 100, and the two positions of the fat / oil after transesterification are defined as 100%. The percentage of the specific fatty acid content of No. 2 changed in comparison with the specific fatty acid content of the two positions before transesterification, expressed as a percentage. The measurement of the fatty acid composition at the two positions is described in Oil Chemistry, 29, 58
7, (1980). The randomization rate in the present invention is 5 to 75%, preferably 10 to 70%, more preferably 15 to 65%. 5% randomization rate
Smaller or greater than 75% is not preferred because it has the disadvantages of 1,3-selective transesterification or complete random transesterification.

The transesterification rate is defined as the difference between the specific triglyceride component of the fat and oil before the start of the reaction and the specific triglyceride component after the transesterification is completely taken as 100. The degree of change compared to before the start is expressed as a percentage, which is described in detail in Japanese Patent Application Laid-Open No. 10-508497. Specifically, it is calculated by the following equation. Ester exchange rate (%) = (Xt-XO) / (Xeq-XO)
× 100 X: a measurable property that depends on the molecular composition of the triglyceride mixture and is a composition before the start of transesterification,
Properties of the composition after complete transesterification have the extreme values thereof. XO: Value of X before transesterification Xeq: Value of X after complete transesterification Xt: Transesterification is measured X value of the composition to be obtained In order to obtain the effect of the modification according to the invention, the transesterification rate is at least 20%, preferably at least 40%, more preferably at least 60%.

The ratio between the randomization ratio and the transesterification ratio is 0.05 to 0.75, preferably 0.10 to 0.7.
0, more preferably 0.15 to 0.65. When the ratio of the randomization rate to the transesterification rate is within the above range, a stable reforming effect can be obtained, which is preferable. The randomization rate and transesterification rate can be adjusted by the transesterification time and other conditions, such as temperature, moisture, PH, stirring conditions, and the catalyst used. In particular,
It is preferable to adjust according to the transesterification time and the type and amount of the catalyst to be used because of excellent operability and the like.

The modified fat or oil of the present invention is a fat or oil mixture containing lauric acid and a saturated fatty acid having 16 or more carbon atoms, and has a lauric acid content of 4 to 40% by weight, preferably 4 to 40% by weight.
The content of the saturated fatty acid having 16 or more carbon atoms is 20 to 80% by weight, preferably 25 to 70% by weight, more preferably 30 to 60% by weight.
The fat / oil mixture which is a weight% is mixed with a randomization rate of 5-75.
%, Preferably 10 to 70%, more preferably 15 to 70%.
It is manufactured by performing transesterification to 65%. In order to reliably achieve the function of the transesterified fat or oil in the present invention, the ratio between the randomization rate and the numerical value of the transesterification rate is 0.05 to 0.75, preferably 0.10 to 0.75.
It is 0.70, more preferably 0.15 to 0.65.
In order to carry out the transesterification reaction in the present invention, it is preferable to use a catalyst, preferably an enzyme catalyst, and more preferably to use an enzyme having low regioselectivity.
The present invention can be achieved by complete or partial transesterification.
0% or more, preferably 40% or more, more preferably 6% or more.
0% or more. The ratio of the numerical value to the randomization ratio is preferably in the above range. Here, attention must be paid to the use, since the position selectivity may change as the activity decreases. Further, the resulting modified fats and oils preferably contain a small amount of trans acid, and specifically have a trans acid content of 10% by weight or less, preferably 5% by weight or less, more preferably 1% by weight or less.

The fat or oil modified according to the present invention has a crystal of β
Since the type transition becomes difficult and the state of β 'is maintained, coarse crystals which cause roughness are hardly generated, and the physical properties of creaming and spreadability are improved. In addition, the conventional disadvantage that the liquid oil cannot be retained in the structure formed by the hard fat or oil and the liquid oil easily oozes due to a change in the temperature of the environment is solved. In addition, the fats and oils modified by the present invention have an increased solidification rate,
For example, effects such as improvement in processing suitability of processed fats and oils can be obtained.

Examples of the processed fats and oils comprising the modified fats and oils of the present invention include margarine, prepared margarine, fat spread, shortening, powdered fat, chocolate, cream, and the like, and those similar to these, such as those called margarine type. Including. The term "margarine type" refers to any product which is deviated from the product standard, but has the same quality or the same purpose of use, etc. .

As an example of the above processed fats and oils, margarine is a plasticized or fluid fluid which is prepared by adding water or the like to edible fats and oils, emulsifying and then quenching or quenching. The oil and fat content refers to those having a fat content of 80% by weight or more, and the adjusted margarine refers to the oil and fat content of 75% by weight or more and less than 80% by weight. The modified fat or oil of the present invention contains 30% by weight or more, preferably 50% or more, of the fat and oil contained in margarine or prepared margarine.
% Or more, more preferably 75% or more. Also,
What is usually added to margarine, such as vitamins,
Sodium chloride, sugar, edible proteins, emulsifiers, preservatives, antioxidants, flavors, coloring agents, fermented milk, other food additives, and the like can be added. Fad spread is a plastic thing made without quenching kneading or quenching kneading after adding water etc. to edible oil and fat, or emulsifying by adding water etc. to edible oil and fat, Or plastic products made by adding flavor ingredients such as processed fruit products, chocolates, and pastes of nuts and quenching and kneading them, in which the proportion of the weight of the flavor ingredients in the product is less than the oil content. And having a fat content of 35% by weight or more and less than 75%. The modified fats and oils of the present invention are at least 30% by weight, preferably at least 50% by weight of the fats and oils contained in the fat spread,
More preferably, the content is 70% by weight or more. What can be usually added to the fat spread can be added. Shortening refers to solids produced by quenching and kneading refined animal fats, vegetable fats, edible processed fats or oils, or mixtures thereof, and fluid or semi-solids produced by adding an emulsifier, etc. Which are provided with processability such as plasticity and emulsification. The modified fats and oils of the present invention comprise 35% by weight or more, preferably 50% by weight or more, more preferably 75% by weight or more of the fats and oils contained in the shortening.
In addition, those which can be usually added to shortening, for example, an antioxidant, an emulsifier, an antifoaming agent, and other additives can be added. In addition, the required amount of the modified fat or oil of the present invention can be added to powdered fat or oil, chocolate, cream or the like according to the required quality.

Here, one of the usage forms which fully brings out the function of the modified fat of the present invention is to use only the modified fat of the present invention as a raw material of a processed fat or oil.

For example, baked confectioneries, cakes, breads and the like can be mentioned as processed products produced by using these modified fats and / or processed fats and oils and using the margarine shortening of the present invention as a raw material. These are the migrants of oils and fats during storage (migr
, movement, and transition) are enhanced.

[0025]

The present invention is described below by way of examples, which are illustrative only, and do not limit the present invention. Unless otherwise specified, all parts and percentages in the examples are on a weight basis.

The methods for measuring the randomization rate, the transesterification rate, the crystal evaluation method, the solidification rate evaluation method, the spread evaluation method, the cream evaluation method, and the baked confectionery evaluation method are described below. [Randomization rate measurement method] 2 of fat mixture before transesterification
Assuming that the difference between the palmitic acid content at the position and the palmitic acid content in the total fatty acid composition was 100, how much the palmitic acid content at the two positions of the fat after transesterification changed compared to the palmitic acid content at the two positions before the transesterification [Measurement method of transesterification rate] expressed as a percentage of 100. The transesterification rate was measured by the method described in paragraph [0017], where X was the amount of triglyceride having 44 carbon atoms + the amount of triglyceride having 46 carbon atoms. [Crystal evaluation method]
S, Vol. 66, no. 5 (May 1989). In the evaluation, β '= β: β' and β are present to the same extent β '> β: β' is present more than β β '>> β: β' is almost used [Evaluation method of solidification rate] The change with time of SFC when the oil and fat completely melted at 70 ° C. was quenched to 5 ° C. was expressed as a solidification rate (%), where the value after 24 hours was 100. [Evaluation method of spread] The change in hardness due to storage and the fineness and uniformity of "grain" of the spread structure after storage were evaluated. The hardness of the spread, when the product temperature is 10 ° C,
Conical needle penetrometer specified by JIS K2220 (NIHON
The penetration was measured using a KAIHEIKI company (cone needle weight 22.5 g). The fineness and uniformity of the “grain” of the spread structure were observed and evaluated. [Evaluation method of cream] The mouthfeel and the tongue of the cream after storage were evaluated organoleptically. [Evaluation method of baked confectionery] Mouth melting and texture after storage were evaluated by sensory evaluation, and the state of the surface of the baked confectionery after storage was observed and evaluated.

Example 1 A mixture of 70 parts of palm oil and 30 parts of palm oil fractionated olein (lauric acid 12%, saturated fatty acid having 16 or more carbon atoms, 36%) was mixed with lipase powder derived from the genus Alcaligenes [Meito Sangyo Co., Ltd.] 1% by weight based on the mixed oil and fat, and transesterification was carried out at 60 ° C. with sufficient stirring. One hour later, the lipase was removed by filtration, and purification was performed according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystals were evaluated. Table 1 shows the results.

Comparative Example 1 The same mixed oil and fat as in Example 1 was added to Alcaligene.
immobilized lipase derived from the genus s [Lipa manufactured by Meito Sangyo Co., Ltd.]
[se QLC] was added at 2% by weight, and transesterification was carried out at 60 ° C. with sufficient stirring. Four hours later,
The lipase was removed by filtration, and a purification treatment was performed according to a conventional method to obtain a transesterified oil. Then, the transesterification rate of the obtained transesterified oil, measurement of the randomization rate, and
The crystals were evaluated. Table 1 shows the results.

Comparative Example 2 The same mixed oil and fat as in Example 1 was subjected to random transesterification using sodium methoxide as a catalyst according to a conventional method. After transesterification, purification treatment was performed according to a conventional method to obtain a transesterified oil. . Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystals were evaluated. Table 1 shows the results.

[0030]

[Table 1]

From Table 1, as a result of the evaluation of the crystallinity by controlling the temperature,
In Example 1, the crystal form stayed at β ′, and the crystal transition to β form, which easily generates a coarse crystal, which leads to deterioration of the quality of margarine shortening, was suppressed. Comparative Example 1 using the immobilized lipase was substantially the same as the transesterification of the chemical catalyst of Example 2 and the crystal transition to β-form proceeded.

Example 2 A mixture of 50 parts of palm stearin and 50 parts of extremely hardened palm kernel oil (24% lauric acid, 47% saturated fatty acid having 16 or more carbon atoms) was mixed with lipase powder derived from the genus Alcaligenes [Meito Sangyo Co., Ltd.] 1% by weight based on the mixed oil and fat, and transesterification was carried out at 60 ° C. with sufficient stirring. One hour later, the lipase was removed by filtration, and purification was performed according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the solidification rate was evaluated. Table 2 shows the results.

Comparative Example 3 Immobilized lipase derived from Mucor Miehei [No.
LIPOZYME manufactured by vo Co., Ltd.] into a column, and the same mixed oil and fat as in Example 2 was added at 60 ° C. and SV (space velocity) 0.4.
The solution was passed under the conditions of (liter / little column), and a transesterification reaction was performed. The transesterification reaction solution was purified according to a conventional method to obtain a transesterified oil. afterwards,
The transesterification rate and the randomization rate of the obtained transesterified oil were measured, and the solidification rate was evaluated. Table 2 shows the results.

[0034]

[Table 2]

Example 2 had the advantage that the solidification rate was rapidly increased (solidification rate) with time, was quickly solidified in the cooling step at the time of adjusting the margarine shortening, and the physical properties after the adjustment were small.

Example 3 A mixture of 70 parts of palm oil and 30 parts of palm kernel oil (14% lauric acid, 36% saturated fatty acid having 16 or more carbon atoms)
Lipase powder derived from the genus Alcaligenes [Lipase PL manufactured by Meito Sangyo Co., Ltd.] was added in an amount of 0.1% by weight to the mixed oil and fat, and the mixture was stirred at 60 ° C. while sufficiently stirring.
Was used to carry out a transesterification reaction. After 16 hours, the lipase was removed by filtration, and purification was carried out according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the solidification rate was evaluated. Table 3 shows the results.

Comparative Example 4 Immobilized lipase derived from Mucor Miehei [No.
LIPOZYME manufactured by vo Corporation was packed in a column, and the same mixed oil and fat as in Example 3 was passed under the conditions of 60 ° C. and SV 1.0 to perform a transesterification reaction. The transesterification reaction solution was purified according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the solidification rate was evaluated. Table 3 shows the results.

[0038]

[Table 3]

The advantage of Example 4 was that the solidification rate increased rapidly (solidification rate) with time, and was quickly solidified in the cooling step during the adjustment of margarine and shortening.

Example 4 65 parts of palm oil, 20 parts of palm stearin and 15 parts of coconut oil
Lipase powder derived from the genus Alcaligenes [Lipase QL, manufactured by Meito Sangyo Co., Ltd.] in a mixed oil and fat (7% lauric acid, 42% saturated fatty acid having 16 or more carbon atoms).
Was added to the mixed oil and fat, and transesterification was carried out at 60 ° C. while sufficiently stirring. One hour later, lipase was removed by filtration, and purification was carried out according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystallinity was evaluated. Table 4 shows the results.

Comparative Example 5 Immobilized lipase derived from Mucor Miehei [No.
LIPOZYME manufactured by vo Corporation was packed in a column, and the same mixed oil and fat as in Example 4 was passed at 60 ° C. under the condition of SV 1.3 to perform a transesterification reaction. The reaction solution was purified according to a conventional method to obtain a transesterified oil. afterwards,
The transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystallinity was evaluated. Table 4 shows the results.

[0042]

[Table 4]

As a result of the evaluation of the crystallinity by controlling the temperature, in Example 4, the crystal form remained at β ′, and the crystal transition to β form, which is likely to generate a coarse crystal leading to the deterioration of the quality of margarine shortening, was suppressed.

Example 5 A mixed oil of 70 parts of a medium melting point of palm and 30 parts of hardened coconut oil (15% lauric acid, saturated fatty acid 41 having 16 or more carbon atoms)
%), Lipase powder derived from the genus Alcaligenes [Lipase QL manufactured by Meito Sangyo Co., Ltd.] was added in an amount of 0.3% by weight based on the mixed oil and fat, and the mixture was added with sufficient stirring.
A transesterification reaction was performed at 0 ° C. One hour later, lipase was removed by filtration, and purification was carried out according to a conventional method to obtain a transesterified oil. Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystals were evaluated. Table 5 shows the results.

Comparative Example 6 Immobilized lipase derived from Mucor Miehei [No.
LIPOZYME manufactured by vo Corporation was packed in a column, and the same mixed oil and fat as in Example 4 was passed under the conditions of 60 ° C. and SV 2.0 to perform a transesterification reaction. The reaction solution was purified according to a conventional method to obtain a transesterified oil. afterwards,
The transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystals were evaluated. Table 5 shows the results.

[0046]

[Table 5]

From Table 5, as a result of the evaluation of the crystallinity by controlling the temperature,
In Example 5, the crystal form stayed at β ′, and the crystal transition to β form, which is likely to generate a coarse crystal, which leads to deterioration in quality of margarine shortening, was suppressed.

Comparative Example 7 The same mixed oil and fat as in Example 4 was subjected to random transesterification using sodium methoxide as a catalyst according to a conventional method. After transesterification, purification treatment was performed according to a conventional method to obtain a transesterified oil. . Thereafter, the transesterification rate and randomization rate of the obtained transesterified oil were measured, and the crystals were evaluated. Table 6 shows the results.

[0049]

[Table 6]

Comparative Example 8 A mixture of 65 parts of palm stearin and 35 parts of coconut oil (17% lauric acid, 32% saturated fatty acid having 16 or more carbon atoms)
Then, a lipase powder derived from the genus Alcaligenes [Lipase QL, manufactured by Meito Sangyo Co., Ltd.] was added to the mixed oil and fat at 1% by weight, and transesterification was carried out at 60 ° C. with sufficient stirring. One hour later, the lipase was removed by filtration, and purification was performed according to a conventional method to obtain a transesterified oil. 90 parts of the transesterified oil was mixed with 10 parts of soybean oil.

Comparative Example 9 55 parts of hardened soybean oil (melting point: 40 ° C.), 30 parts of palm oil and 15 parts of soybean oil were mixed.

A spread (oil content: 70%) containing 20 parts of Example 2 or Comparative Example 3, 20 parts of soybean hardened oil (melting point: 34 ° C.) and 60 parts of soybean oil as an oil phase was prepared according to a conventional method.
The storage at 20 ° C. for 12 hours for 12 hours was repeated for 8 weeks.
Changes in the hardness of the spread and the grain of the spread tissue after storage were evaluated. Table 7 shows the results.

[0053]

[Table 7]

While the spread used in Example 2 had no change in hardness during storage and had a constant quality, and the grain of the tissue was fine and uniform, the spread used in Comparative Example 3 had a large change in hardness and the grain of the tissue was large. Was rough and had an overall rough impression.

20 parts of Example 3 or Comparative Example 4, 20 parts of hardened soybean oil (melting point: 42 ° C.), and a spread (oil content: 70%) containing 60 parts of soybean oil as an oil phase were prepared according to a conventional method.
The storage at 20 ° C. for 12 hours for 12 hours was repeated for 8 weeks.
Changes in the hardness of the spread and the grain of the spread tissue after storage were evaluated. Table 8 shows the results.

[0056]

[Table 8]

The spread used in Example 3 had no change in hardness during storage and had a constant quality, and the grain of the tissue was fine and uniform. However, the spread used in Comparative Example 4 had a large change in hardness and the grain of the tissue was large. Was rough and had an overall rough impression.

42 parts of Example 5 or Comparative Example 6 or Comparative Example 7, 25 parts of whole milk powder, 15 parts of sugar, 0.4 part of lecithin
A fat cream consisting of a portion was prepared according to a conventional method, sealed in a bag sandwiched with biscuits, and stored at room temperature for 60 days. Thereafter, the cream was dissolved in the mouth and evaluated for texture. Table 9 shows the results.

[0059]

[Table 9]

In the sand cream of Example 5, the roughening of the texture due to the coarsening of the fat crystals was suppressed while maintaining the sharp melting point of the middle melting point of palm, which is the raw material fat for transesterification.

Using the processed fats and oils of Example 4 and Comparative Examples 5, 8, and 9, shortening containing 0.2% lecithin was prepared, and 100 parts of flour flour, 35 parts of shortening,
A biscuit was baked by a conventional method using a mixture of 40 parts of white sugar, 5 parts of whole egg, 0.5 part of salt and 18 parts of water. The biscuit was sealed in a bag and stored at room temperature for 60 days. Thereafter, dissolution in the mouth, evaluation of texture, and state of the surface after storage were observed and evaluated. Table 10 shows the results.

[0062]

[Table 10]

From the results shown in Table 10, it can be seen that the product of the present invention can effectively prevent the whitening phenomenon of the surface of baked confectionery caused by migration of fats and oils by using it for margarine shortening.

[0064]

According to the present invention, by adjusting the randomization rate in the transesterification reaction without blending special fats and oils, it is possible to improve the crystal coarsening and the leaching of liquid oil. Modified fats and oils,
The modified fats and oils can be suitably used as a raw material for margarine and shortening, and in addition, processed products using these as raw materials have improved migration and the like.

Claims (10)

[Claims] An oil or fat mixture containing 4 to 40% of lauric acid and 20 to 80% of a saturated fatty acid having 16 or more carbon atoms,
A method for producing a modified fat or oil, comprising subjecting a transesterification to a randomization rate of 5 to 75%. 2. The modified oil or fat according to claim 1, wherein the transesterification is carried out such that the ratio of the randomization rate to the transesterification value is in the range of 0.05 to 0.75. Law. 3. The method according to claim 1, wherein the randomization rate is 10 to 70%. 4. The process according to claim 1, wherein the lauric acid content is 4 to 20%. 5. The content of a saturated fatty acid having 16 or more carbon atoms is 2
The method for producing a modified fat or oil according to claim 1 or 2, which is 5 to 70%. 6. The method for producing a modified fat or oil according to claim 1, wherein the transesterification is carried out by an enzyme having low regioselectivity. 7. The method according to claim 6, wherein the enzyme having low regioselectivity is an enzyme having a 1,3 selectivity of 0.1 to 1. 8. A modified oil or fat obtained by the production method according to claim 1. 9. A processed fat or oil comprising the modified fat or oil of claim 8. 10. A processed product comprising the modified fat or oil of claim 8 and / or the processed fat or oil of claim 9.