JP3976112B2 - Method for producing diglyceride-containing oil / fat composition and oil / fat composition using the same - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a diglyceride-containing fat and oil in a short time and simply by transesterifying the fat and monoglyceride, and also relates to the modification of palm oil using this production method.
[0002]
[Prior art]
The main component of natural fats and oils is triglyceride, but diglycerides, monoglycerides, complex lipids such as free fatty acids and phospholipids, etc. are included as other accessory components. Among them, diglyceride is industrially used as a base in the fields of cosmetics, pharmaceuticals and the like, and is also used as a physical property improving agent for fats and oils in the food field.
[0003]
These diglycerides can be obtained by separation from fats and oils, but can also be produced by using a chemical reaction using an alkali catalyst or a biochemical reaction using an enzyme such as lipase. In the production method using a chemical reaction, a method of reacting animal and vegetable oils or fats or a predetermined fatty acid and glycerin as raw materials at a high temperature of 200 ° C. or higher using a catalyst such as sodium hydroxide is common. On the other hand, in the production method utilizing biochemical reaction, a method of hydrolyzing fats and oils using lipase as a catalyst, or a method of ester synthesis of a predetermined fatty acid and glycerin (JP-A 64-71495, JP-A-4-330289) Etc. Furthermore, a method combining a chemical reaction and a biochemical reaction (Japanese Patent Laid-Open No. 10-234392) has also been proposed.
[0004]
On the other hand, the use of palm oil supplied at low cost is increasing, but it cannot be said that it is sufficiently effectively used due to the crystallinity problem specific to palm oil. Examples of means for modifying palm oil include methods such as fractionation, curing, and transesterification. Above all, by re-arranging symmetrical triglycerides deeply related to crystallinity by randomization using chemical transesterification, the crystallinity of palm oil can be improved. In addition, proposals have been made to impart useful functions as plastic fats and oils by a randomization reaction in a mixed system with other fats and oils (Japanese Patent Laid-Open Nos. 53-208, 57-74041, and 57-12950). .
[0005]
[Problems to be solved by the invention]
However, in the production method of diglyceride using the above chemical reaction, since glycerin is used as a raw material, it is a big problem that the mutual solubility between glycerin and fat or fatty acid is low. The reaction at a high temperature of 200 ° C. or higher is necessary. Therefore, there is a problem that the cost is high, which is not preferable from an economical point of view, and there is a risk of side reactions such as formation of a polymer by a high temperature reaction.
[0006]
In addition, although the reaction temperature is low in the production method by biochemical reaction, for example, in the method of hydrolyzing fats and oils, as the reaction proceeds, more monoglyceride is produced than diglyceride, and it is difficult to increase the yield of the desired diglyceride. At the same time, a considerable amount of fatty acid is generated. Further, when the ester synthesis reaction is used, there is a problem that the reaction time is long and the efficiency is low due to the heterogeneous reaction resulting from the low mutual solubility of glycerin and fatty acid as described above. Although it is possible to shorten the reaction time by increasing the amount of enzyme used, the enzyme is generally expensive and cannot be said to be a practical measure. Furthermore, in order to increase the yield, the process is complicated such as requiring dehydration during the reaction. In addition, although a proposal that combines the advantages of both has been made, the reality is that it has not yet reached a fundamental solution.
From such a current situation, a new method for producing an oil and fat composition having a high diglyceride content in a short time and simply has been desired.
[0007]
On the other hand, in the reforming method of palm oil, the above-described reforming method improves the function as a plastic fat, but deteriorates the solubility in the mouth due to the trisaturated triglyceride produced as a by-product in the randomization reaction and the coarseness of crystals. However, it is difficult to say that it is practically sufficient, and a palm oil reforming method that overcomes these drawbacks has been desired.
[0008]
[Means for Solving the Problems]
As a result of diligent research to solve the above-mentioned problems relating to the production of diglyceride, the present inventors conducted a transesterification reaction between fats and oils (triglyceride) and monoglyceride having excellent mutual solubility, so that diglyceride can be easily and extremely quickly. The present inventors have found that oils and fats can be obtained, and have found that a modified palm oil composition of excellent quality can be obtained by applying this method to the modification of palm oil, thereby completing the present invention.
[0009]
That is, the first of the present invention relates to a method for producing diglyceride-containing fats and oils characterized by transesterifying monoglyceride and fats and oils.
[0011]
The third aspect of the present invention relates to the modification of palm oil characterized by transesterifying monoglyceride and palm oil.
[0013]
DETAILED DESCRIPTION OF THE INVENTION
The fats and oils used in the present invention are mainly composed of triglycerides, but of course may contain subcomponents such as monoglycerides and diglycerides. The type of fats and oils to be used is not particularly limited. Specifically, corn oil, rapeseed oil, soybean oil, olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil, palm oil, palm kernel oil and other vegetable oils, Hyelsin Cross oils such as rapeseed oil, natural fats and oils such as animal oil such as fish oil, beef tallow, pork fat, milk fat and egg yolk oil, as well as processed fats and oils such as transesterified oil, hardened oil and fractionated oil, etc. Can be used alone or in admixture of two or more. In this, when palm oil or its fractionated oil is used as a raw material, it can also aim at remarkably improving the crystallinity derived from palm oil.
[0014]
Moreover, the monoglyceride used for this invention may contain a triglyceride, a diglyceride, etc. as a subcomponent, and there is no restriction | limiting in particular also about the constituent fatty acid. As will be described later, it can be selected according to the physical properties of the obtained oil and fat composition, but inexpensive reaction monoglyceride, distilled monoglyceride and the like which are commercially available as edible emulsifiers may be used.
[0015]
The transesterification reaction of the present invention can be used in any of a chemical reaction using a normal alkali metal catalyst such as sodium methylate and a biological reaction using an enzyme such as lipase. In this case, since the mutual solubility of monoglyceride and triglyceride is high, the reaction can be completed in an extremely short time.
[0016]
Although the ratio of the fats and monoglycerides used as the raw material for the reaction in the present invention is not particularly limited, the diglyceride content after the reaction can be controlled by adjusting the ratio of the monoglyceride used. For example, when the monoglyceride content in the starting material is 5% by weight, the diglyceride content after the reaction is about 15% by weight. Generally, when the amount of monoglyceride used is increased, the yield of diglyceride after the reaction is increased. However, when the amount of monoglyceride is too large, the amount of monoglyceride remaining after the reaction is also increased. From these viewpoints, the amount of monoglyceride to be used is preferably 50% by weight or less, more preferably 5 to 40% by weight.
[0017]
After completion of the reaction, the remaining fatty acid and monoglyceride can be removed using a general method such as vacuum steaming, molecular distillation or chromatography, but the monoglyceride may remain contained depending on the application. The removed monoglyceride can be reused as a raw material.
[0018]
In the diglyceride-containing oil and fat composition obtained in the present invention, by adjusting the composition, it is possible to adjust individual physical properties required for the oil and fat processed food, such as consistency and melting point. For the adjustment of such a composition, selection of raw materials at the time of reaction is important, but furthermore, normal oil processing techniques such as hardening and fractionation after reaction can be combined.
[0019]
When performing the curing treatment, it may be non-selective hydrogenation or selective isomerization hydrogenation depending on the application. For example, in selective isomerization hydrogenation, a method using a nickel catalyst poisoned with sulfur. And sulfur-containing amino acids such as methionine, thiazole ring-containing compounds, sodium metabisulfite, and sulfur compounds such as potassium are exemplified, but the method is not limited thereto.
[0020]
When performing the fractionation treatment, any method of a solventless fractionation method, a method using an organic solvent such as n-hexane or acetone, or a method using an aqueous surfactant solution may be used, but the method is not limited thereto.
[0021]
The diglyceride-containing oil and fat composition of the present invention can be used alone, but can also be used by mixing with other oils and fats as necessary. Oils and fats used for mixing are not particularly limited, vegetable oils such as corn oil, rapeseed oil, soybean oil, olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil, palm oil, palm kernel oil, Hyelcin rapeseed oil, etc. Crude oil, fish oil, beef tallow, pork tallow, milk fat, animal oil such as egg yolk oil, etc., or processed oils and fats that have been separated, hydrogenated, transesterified etc. Can be used.
[0022]
The oil or fat composition or modified palm oil composition obtained in the present invention can be used in general for foods containing oil and fat, specifically, margarine, shortening, chocolates, frying oil, butter cream, etc. In addition, examples of the oil-in-water emulsion include whipped cream, ice cream, flower paste, mayonnaise and the like.
[0023]
【Example】
EXAMPLES The present invention will be described in detail below with reference to examples, but these examples do not limit the present invention in any way. In the following description, “parts” and “%” all mean “parts by weight” and “% by weight”.
[0024]
Example 1
Using 60 parts of high oleic safflower and 40 parts of monoolein, the reaction was carried out at 80 ° C. for 30 minutes using sodium methylate as a catalyst according to a conventional method. The composition after the reaction was 1.2% free fatty acid, 23.0% monoglyceride, 52.1% diglyceride, and 23.6% triglyceride.
[0025]
Subsequently, steam distillation was performed to remove free fatty acids and monoglycerides. The composition of the obtained diglyceride-containing oil and fat composition was 0.2% monoglyceride, 68.6% diglyceride, and 31.2% triglyceride.
[0026]
(Comparative Example 1)
Although 80 parts of high oleic safflower and 20 parts of glycerin were used and reacted for 1 hour at 80 ° C. under reduced pressure using sodium hydroxide as a catalyst, the reaction hardly proceeded.
[0027]
(Example 2)
When reaction was performed at 40 ° C. in the presence of molecular sieves using 60 parts of high oleic safflower, 40 parts of monoolein and 10 parts of immobilized lipase (Lipozyme IM, manufactured by Novo Nordisk Co., Ltd.), the reaction took about 2 hours. The diglyceride content in the composition was 50%.
[0028]
(Comparative Example 2)
When 85 parts of oleic acid, 15 parts of glycerin, and 10 parts of immobilized lipase (Lipozyme IM, manufactured by Novo Nordisk Co., Ltd.) were reacted at 40 ° C. in the presence of molecular sieves, the diglyceride content in the reaction composition was It took about 5 hours to reach 50%.
[0029]
(Example 3)
45 parts of palm oil, 45 parts of palm soft oil (IV = 62), 10 parts of glycerin monofatty acid ester (trade name: Emergy MS, manufactured by Riken Vitamin Co., Ltd.), and at 80 ° C. using sodium methylate as a catalyst according to a conventional method Reacted for 30 minutes. Subsequently, steam distillation was performed to remove free fatty acids and monoglycerides. The diglyceride content in the obtained modified palm oil composition was 28.7%.
[0030]
(Comparative Example 2)
The same operation as described in Example 1 was performed except that 10 parts of extremely hardened rapeseed oil was used in place of the glycerin monofatty acid ester of Example 3. The diglyceride content in the obtained oil and fat composition was 4.2%.
[0031]
Example 4
<Oil phase adjustment>
70 parts of the modified palm oil composition obtained in Example 3, 30 parts of rapeseed oil, and 0.5 parts of lecithin were dissolved by heating at 60 ° C.
[0032]
<Making Margarine>
While stirring, 16.5% of water was added to 83.5% of the adjusted oil phase part, emulsified for 20 minutes, and then cooled and kneaded with a mini-combinator to prepare margarine. The margarine emulsified state and the textured state of texture, gloss, nobi and the like were very good.
[0033]
(Comparative Example 4)
<Oil phase adjustment>
70 parts of fats and oils obtained in Comparative Example 2, 30 parts of rapeseed oil and 0.5 parts of lecithin were dissolved by heating at 60 ° C.
[0034]
<Making Margarine>
While stirring, 16.5% of water was added to 83.5% of the adjusted oil phase part, emulsified for 20 minutes, and then cooled and kneaded with a mini-combinator to prepare margarine. The emulsified state of margarine was good, but the textured state of texture, luster, nobi and the like was greatly inferior to the margarine obtained in Example 4.
[0035]
【The invention's effect】
As described above, according to the method of the present invention, a highly pure diglyceride-containing oil and fat composition can be obtained in a short time and simply. Furthermore, the modified palm oil composition obtained by using palm oil as a raw material has remarkably improved crystallinity, and is extremely useful in the production of fats and oils products using these.

Claims (2)

  A process for producing a diglyceride-containing oil / fat composition comprising transesterifying monoglyceride and oil / fat.   A method for reforming palm oil, wherein the fat according to claim 1 is palm oil.