JPH0471120B2 - - Google Patents

Description

[Detailed description of the invention]

TECHNICAL FIELD The present invention relates to a plastic fat and oil, a method for producing the same, and a coating material containing the same. Edible fats and oils are used for various purposes by taking advantage of their physical properties. One example is coating oils and spray oils for confectionery, in which case the oils not only improve the flavor of foods but also function as a protective film. The physical properties of oils and fats used for this purpose include the ability to form a physically and chemically strong film, low permeability to water vapor, and good texture. Generally, hard butters such as cocoa butter are often used for coatings for confectionery. However, although hard butter has a satisfactory texture, its coating has poor plasticity and is brittle, making it insufficient for some purposes. It is desirable that the coating oil has a small catalytic range like hard butter, and also has plasticity and extensibility. Acetin fat, which is mainly composed of glycerol diacetomonostearate, is well known as a fat that satisfies these physical properties. However, as its name suggests, this oil and fat has acetic acid groups, so when it is hydrolyzed, it can generate the pungent odor of acetic acid. Furthermore, the manufacturing process is complicated, as excessive acetic acid is required, and when acetic anhydride is used as a raw material, a large amount of acetic acid is produced as a by-product. The present inventors have conducted extensive research in order to produce a plastic fat with physical properties similar to acetin fat without such drawbacks by combining only long-chain fatty acids, and as a result, we have now found that the total number of carbon atoms in the constituent fatty acids is 58 or more. The present invention was completed based on the discovery that a specific disaturated-unsaturated triglyceride satisfies this condition. In other words, the present invention provides a method in which the total number of carbon atoms of the constituent fatty acids is 58 or more, and each constituent fatty acid has a carbon number of 22 or more.
The present invention provides a plastic oil and fat mainly composed of the above saturated fatty acids, saturated fatty acids having 18 or more carbon atoms, and triglycerides that are unsaturated fatty acids having 16 to 22 carbon atoms, a method for producing the plastic oil, and a coating material containing the plastic oil. It is something. Distearyl monoolein (S ₂ O) is well known as a typical disaturated-unsaturated triglyceride, but this glyceride can be used regardless of the bonding position of the unsaturated acid, α or β. Even the mixture is a brittle solid at room temperature (20°C).
Furthermore, since the polymorphism detected by X-rays takes the β-form, a so-called fat plume may be produced depending on the solidification conditions. However, the appearance of the solidified oil and fat according to the present invention is translucent (paraffin-like) and extensible, regardless of whether it is rapidly cooled or slowly cooled. Further, X-ray diffraction shows that it is in the β'-form and its plasticity is stably maintained over a long period of time when stored at room temperature. The fatty acid constituting the plastic fat of the present invention has a carbon number of
Saturated fatty acids of 22 or more (especially behenic acid), carbon number 18
The above saturated fatty acids (preferably stearic acid, arachidic acid, behenic acid), and unsaturated fatty acids having 16 to 22 carbon atoms (preferably unsaturated fatty acids having 18 carbon atoms such as oleic acid, linoleic acid, and linolenic acid) . Typical triglycerides that are the main component of the plastic fats and oils of the present invention are dibehenyl monolinoleate or monooleate, but one of the saturated acids may be substituted with stearic acid or arachidic acid,
A mixture of these may also be used. The bonding position of the unsaturated fatty acid may be either α or β, but a mixture thereof is preferred. Dibehenylmonostearin and other triglycerides with long-chain saturated fatty acids such as behenic acid have already been found in the literature, but the physical properties of this oil and fat are similar to ordinary solid fats with a high melting point, and the plastic oil and fat of the present invention is completely different. Generally, in order to impart plasticity to a fat or oil, a suitable solid fat is mixed and melted in a liquid oil, and then the mixture is rapidly cooled and kneaded. Shortening is a typical example. However, in this case, its physical properties vary greatly depending on the conditions of quenching and kneading, and it does not have the extensibility of acetin fat or the plastic fat of the present invention. The plastic fats and oils having the specific constituent fatty acids of the present invention are suitable for coating fats and oils or coating fat compositions to be coated on the surface of foods, either as they are or mixed with other known ingredients. As the coating oil/fat component, the plastic oil/fat having the specific constituent fatty acids of the present invention may be melted and used as it is, but it may also be mixed with other fats/oils as long as the physical properties are not impaired. There are no particular restrictions on the oils and fats that can be used in combination, as long as they are edible, and include vegetable oils such as soybean oil, rapeseed oil, palm oil, corn oil, cottonseed oil, coconut oil, palm kernel oil, lard, fish oil, whale oil,
Any animal fats and oils such as milk fat can be used, and those obtained by hydrogenation or transesterification can also be used. The plastic oil and fat of the present invention can be used as a food coating agent not only for coating cakes as mentioned in the examples, but also as a spray oil for dry fruits such as raisins, nuts, etc., and for moisture-proofing and drying. Foods that need to be avoided (e.g. jelly)
It can be used as an edible coating oil. In addition, as a coating agent, in addition to cases where only fats and oils are used as in spray oil, it is also used in confectionery by mixing with sugar, powdered milk, cocoa, tyokolate liquor, peanut butter, powdered almonds, powdered cheese, etc. as in thiokolate coating. It can be used as a coating. For example, in a thiokolate coating, 25 to 50% of the oil according to the present invention (or a mixture of other oils and fats within a range that does not impair the characteristics of the oil and fat according to the present invention) and 10 to 10% cocoa powder.
15%, 0 to 15% milk powder, 0 to 15% milk powder
It is best to use a range of 15% sugar and 35-55% sugar. In this case, by substituting some or all of the cocoa powder and cocoa powder with peanut butter or powdered almonds, a product that takes advantage of the flavor characteristics of each can be obtained. Although the method for producing the plastic fat of the present invention is not particularly limited, the following production method is suitable. Fatty acid diglycerides with 18 or more carbon atoms, such as glycerol dibehene and glycerol stearyl behen, which always have a fatty acid residue with 22 or more carbon atoms (particularly behenic acid residue), and 16-22 carbon atoms, such as oleic anhydride, isopropenyl oleate, etc. There is a method of carrying out an esterification reaction with a derivative of an unsaturated fatty acid. In addition, 30-60% by weight of fatty acid triglycerides with 18 or more carbon atoms containing fatty acid residues with 22 or more carbon atoms (especially behenic acid) such as tribehene or extremely hardened high-quality rapeseed oil, and saturated fatty acid content of 20% by weight. % or less of unsaturated fatty acids (e.g., soybean oil, rapeseed oil, safflower oil) with 40 to 70% by weight, and the transesterified oil is fractionated with a solvent to obtain the desired fat or oil. There are ways to get it. In this case, transesterification involves randomly arranging fatty acids, and the catalyst used is commonly used sodium methylate, caustic soda, etc. at 0.1 to 0.3% by weight based on the fat and oil, and the reaction temperature was 70 to 70%.
Perform at 150℃. After the reaction, the catalyst is removed by washing with water. In this case, the saturated fatty acid triglyceride having 18 or more carbon atoms may be a transesterification product of methyl or ethyl ester of a fatty acid having 18 or more carbon atoms and triacetin. For solvent fractionation, a solvent used for fractionating fats and oils, such as n-hexane and acetone, is used in an amount 2 to 5 times the amount of fats and oils. Dissolve the transesterified oil in this solvent, cool it to 15-25°C, and separate the precipitated trisaturated glyceride. Keep the liquid at -5~5℃
The desired product is obtained by collecting the precipitated disaturated-unsaturated glyceride upon cooling. Hereinafter, the present invention will be explained in further detail with reference to Examples. Example 1 Extremely hardened high quality rapeseed oil (fatty acid composition 2.9% palmitic acid, 40.7% stearic acid, 7.4% arachidic acid, 46.9% behenic acid, 2.0% others)
A mixed oil of 50wt% and safflower oil (6.5% palmitic acid, 2.5% stearic acid, 16.0% oleic acid, 74.1% linoleic acid, 0.9% linolenic acid) is catalyzed with 0.1% sodium methylate to fat. and treated at 80°C for 30 minutes to obtain transesterified oil. This transesterified oil was dissolved in 5 ml of acetone per 1 g at 60°C, then cooled to 25°C with stirring, and the precipitated high melting point fraction mainly composed of trisaturated triglycerides (yield: 15% based on the transesterified oil) ) to remove. This liquid was cooled to 3 to 5° C. with stirring, and the precipitated target section (medium melting point section) was collected. After removing the solvent, this section is deodorized by a conventional method to obtain the desired product. The high melting point fraction and low melting point fraction produced as by-products in this step can be mixed with the raw material before transesterification and reused. Example 2 Methyl behenate (stearic acid 14.2%, arachidic acid 11.4%, behenic acid 72.0%, other 2.3%) 500
g, rapeseed oil (3.6% palmitic acid, 1.7% stearic acid, 57.7% oleic acid, 22.2% linoleic acid,
Mix 500 g of linolenic acid (12.7%, erucic acid 2.3%) and 110 g of triacetin, and react with 0.15% oil-to-oil sodium methylate as a catalyst at 20 mmHg and 70°C while removing by-product methyl acetate.
A transesterified fat was obtained. 2.5ml of this transesterified fat per 1g of fat
- Dissolve in hexane, cool to 17-19°C and separate the precipitated high melting point part. This liquid was cooled to 0 to 2°C, and the precipitated target intermediate melting point fraction was collected and treated in the same manner as in Example 1 to obtain the target product. Example 3 Tribehene (stearic acid 10.9%, arachidic acid
8.5%, behenic acid 80.6%) 200g, soybean oil (palmitic acid 10.6%, stearic acid 41%, oleic acid
24.4%, linoleic acid 53.7%, linolenic acid 7.2%,)
In the same manner as in Example 1, 200 g of mixed oil was transesterified and then subjected to solvent fractionation to obtain the desired classification. Example 4 High boiling point classification of highly hydrogenated fish oil fatty acids (palmitic acid 1.3%, stearic acid 18.2%, arachidic acid
38.8%, behenic acid 37.2%, other 1.7%) and safflower oil.
A 50 wt % mixed oil was transesterified in the same manner as in Example 1, and the desired fractions were obtained by solvent fractionation. Comparative Example 1 For comparison, a mixed oil of 200 g of extremely hardened soybean oil (palmitic acid 10.5%, stearic acid 89.5%) containing no behenic acid or arachidic acid and 200 g of safflower oil was transesterified according to Example 1, and a solvent was used. Fractionation was performed to collect the intermediate melting point category. Table 1 shows the analytical values of the intermediate melting point category obtained in Examples 1 to 4 and Comparative Example 1, and Table 2 shows the triglyceride composition determined by gas chromatography and the appearance after storage at 20°C for one month. In addition, 20 of each intermediate melting point category
FIG. 1 shows an X-ray diffraction pattern measured after storage at ℃ for one month. In the figure, A shows the results of Examples 1 to 4, and B shows the results of Comparative Example 1.

[Table] (Note) *Yield based on transesterified fat

[Table] Example 5 72 g of glycerol dibehenate (73.1% glycerol dibehenate, 15.4% glycerol behenyl arachinate, 8.1% glycerol behenyl stearate, 3.4% others) and 32 g of unsaturated fatty acid isopropyl ester (fatty acid composition: Palmitic acid 1.5%, oleic acid 62.3%, linoleic acid 27.8%
%, linolenic acid (8.4%) was reacted with para-toluenesulfonic acid (0.5%) at 220℃ for 5 minutes to obtain an iodine value of 45.1, a melting point of 43.5℃, and a glyceride composition.
A disaturated-unsaturated triglyceride containing 72.1% _{of C62} , 15.5% of _C60 , 8.1% of _C58 , and 2.4% of others was obtained. The appearance of this oil and fat after storage at 20°C for one month was paraffin-like and extensible. Example 6 As an example showing one of the characteristics of the fats and oils according to the present invention, thiokolate for coating using the fats and oils of Examples 1 and 2 (fat 29%, thiokolate liquor)
12% cocoa butter, 5% cocoa butter, 54% powdered sugar) to coat the entire surface of a 2.2 g cube-cut sponge cake (containing 35.0% moisture), and place the cake and desiccator (silica gel) in a desiccator for 25 minutes. The cake was stored at ℃, and the weight loss due to water evaporation of the cake was measured. The fat and oil used for comparison in this case was commercially available trans-type hard butter (melting point 36.5°C, iodine value
69.1). The results are shown in Figure 2. In the figure, 1 is the result when the fat of Example 1 was used, 2 is the result when the fat of Example 2 was used, and 3 is the result when commercially available trans-type hard butter was used.
The data are expressed as the sum of the weight loss of three cakes. It can be seen that when coated with the oil and fat according to the present invention, water evaporates less. Example 7 Moisture absorption test of fried peanuts Peanuts were fried using the oil and fat of Example 3 and commercially available palm oil, and the peanuts were stored at 25°C with a humidity of 80% to determine the moisture absorption state of the peanuts (measured by loss on drying at 105°C). I looked into it. The results are shown in Figure 3. In addition, in the figure, 1 is when fried with commercially available palm oil, 2 is
These are the results when fried with the oil and fat of Example 3. It can be seen that the peanuts fried and covered with the oil according to the present invention have low hygroscopicity.

[Brief explanation of drawings]

Figure 1 shows the X-ray diffraction diagram of the intermediate melting point sections obtained in Examples 1 to 4 and Comparative Example 1 after storage at 20°C for one month, and Figure 2 shows the transparency obtained by coating the sponge cake in Example 5. Graph showing the results of the moisture test,
FIG. 3 is a graph showing the results of a moisture absorption test on fried peanuts conducted in Example 6.

Claims (1)

[Scope of Claims] 1. The total number of carbon atoms in the constituent fatty acids is 58 or more, and each constituent fatty acid is a saturated fatty acid with a carbon number of 22 or more, a saturated fatty acid with a carbon number of 18 or more, and a saturated fatty acid with a carbon number of 16 to 16.
A plastic fat and oil mainly composed of triglycerides, which are 22 unsaturated fatty acids. 2 Number of carbon atoms containing fatty acid residues having 22 or more carbon atoms
30-60% by weight of fatty acid triglycerides of 18 or more and 40-70% by weight of vegetable oil containing 20% by weight or less of saturated fatty acids are transesterified, followed by solvent fractionation, and the total number of carbon atoms in the constituent fatty acids is 58 or more, and each constituent fatty acid has a carbon number
A method for producing plastic fats and oils mainly composed of triglycerides, which are saturated fatty acids having 22 or more carbon atoms, saturated fatty acids having 18 or more carbon atoms, and unsaturated fatty acids having 16 to 22 carbon atoms. 3. The method for producing plastic fats and oils according to claim 2, wherein the fatty acid triglyceride having 18 or more carbon atoms is a transesterification product of a methyl or ethyl ester of a fatty acid having 18 or more carbon atoms and triacetin. 4 A method characterized by carrying out an esterification reaction between a fatty acid diglyceride having 18 or more carbon atoms, which always has a fatty acid residue having 22 or more carbon atoms, and a derivative of an unsaturated fatty acid having 16 to 22 carbon atoms, in which the total number of carbon atoms of the constituent fatty acids is 58 or more, and each constituent fatty acid has a carbon number
A method for producing plastic fats and oils mainly composed of triglycerides, which are saturated fatty acids having 22 or more carbon atoms, saturated fatty acids having 18 or more carbon atoms, and unsaturated fatty acids having 16 to 22 carbon atoms. 5 The total number of carbon atoms in the constituent fatty acids is 58 or more, and each constituent fatty acid is a saturated fatty acid with a carbon number of 22 or more, a saturated fatty acid with a carbon number of 18 or more, and a saturated fatty acid with a carbon number of 16 or more.
A coating agent characterized by containing a plastic oil mainly composed of triglyceride, which is a 22-unsaturated fatty acid.