JP6450218B2 - Method for producing transesterified oil - Google Patents

Description

  The present invention relates to a method for producing a transesterified oil.

  The process of chemical transesterification of fats and oils using a catalyst proceeds in the order of “heating of fats and oils → vacuum dehydration → injecting catalyst”. When the catalyst is charged, the alkaline substance, which is a catalyst, reacts with fats and oils, whereby a chemical transesterification reaction proceeds and a by-product soap (alkali metal salt of fatty acid) is generated. And when chemical transesterification reaction is complete | finished, the amount of soap about 50000 ppm is contained in fats and oils.

  Until now, in order to remove the soap, the oil and fat after the chemical transesterification reaction has been subjected to a process of “water washing → stationary → water phase and emulsified phase removal”. A part of the fat and oil is lost together with the layer, and the yield of the product is lowered, and when water is added again after removing the water layer and the emulsified layer in order to remove more soap, emulsification is performed between the water layer and the oil layer. Once emulsification occurs, there is a problem that the fat loss becomes enormous (Patent Document 1). On the other hand, if the amount of water used in washing is reduced, soap cannot be removed sufficiently, the amount of adsorbent used in the adsorption treatment such as white clay treatment increases, and the unfavorable flavor peculiar to the adsorbent is transferred to the fat and oil, resulting in a fat and oil flavor. There is a problem that the adsorbent separation efficiency by filtration after the adsorption treatment is deteriorated and the yield of fats and oils is deteriorated.

JP-A-51-61510

  An object of the present invention is to provide a transesterified oil before it is subjected to a deodorizing treatment by removing soap contained in the fat and oil after the transesterification at low cost, efficiently and with a good yield.

  As a result of intensive research to solve the above-mentioned problems, the present inventors have conducted a transesterification reaction of animal and vegetable oils and fats with an alkaline substance, and then added neutral water to the oils and fats like showering. Since the total surface area of the neutral water is large, the total contact area with the soap also increases proportionally, and since the water droplets have an appropriate droplet diameter, the water droplets settle in the oil and fat while holding the soap. As a result, most of the liquid mixture was divided into an oil layer and an aqueous layer, and an emulsified layer was hardly formed, so it was found that soap could be removed without lowering the yield of fats and oils as before, and the present invention was completed. It came to do.

That is, the first of the present invention is a first step in which animal and vegetable fats and oils are subjected to a transesterification reaction using an alkaline substance,
By adding 10 to 200 parts by weight of neutral water droplets to 100 parts by weight of the animal and vegetable oils and fats obtained after the transesterification reaction, the water droplets are precipitated in the oils and fats. A second step of obtaining a liquid comprising an aqueous layer and a first oil layer;
The present invention relates to a method for producing a transesterified oil for use in deodorizing treatment, comprising a third step of removing a first aqueous layer from the liquid obtained in the second step to obtain a transesterified oil having a residual soap content of 350 to 1200 ppm. .

  Preferably, the adsorbent that is subjected to decolorization before deodorization and is used during decolorization is white clay.

  According to the present invention, it is possible to provide a transesterified oil before being subjected to a deodorizing treatment by removing soap contained in the oil and fat after the transesterification at low cost, efficiently and with a good yield.

  Hereinafter, the present invention will be described in more detail. The method for producing the transesterified oil of the present invention is as follows. First, animal and vegetable fats and oils are transesterified using an alkaline substance as a catalyst, and then the fats and fats are brought into contact with a specific amount of neutral water by a specific method, so that water droplets adsorbing soap on the interface are precipitated in the fats and oils. Thus, the content of soap in the oil or fat is set to a specific amount or less.

<First step: transesterification>
In the transesterification reaction, animal and vegetable fats and oils are transesterified using an alkaline substance as a catalyst. Specifically, for example, the usual method can be followed in the order of “heating of fat / oil → dehydration → injecting catalyst”, but is not limited thereto. When the catalyst is charged in this reaction step, the alkaline substance as a catalyst reacts with animal and vegetable oils and fats, whereby a chemical transesterification reaction proceeds and a by-product soap is generated. Here, soap is a fatty acid alkali metal salt obtained by reacting triglyceride, diglyceride, or monoglyceride-derived fatty acid and an alkaline substance contained in animal or vegetable oils and fats subjected to transesterification.

  The animal and vegetable oils and fats used for producing the transesterified oil of the present invention are not particularly limited, but examples of vegetable oils include safflower oil, soybean oil, rapeseed oil, palm oil, palm kernel oil, cottonseed oil, coconut oil, rice bran Oil, sesame oil, castor oil, linseed oil, olive oil, tung oil, coconut oil, peanut oil, kapok oil, cacao oil, wood wax, sunflower oil, corn oil, etc. Examples include pork fat, sheep fat, beef leg fat, and the like, and hydrogenated oils, transesterified oils, fractionated oils, and mixed oils thereof may also be used.

  In the transesterification reaction, when monoglyceride, diglyceride, or triglyceride in animal and vegetable fats and oils are reacted with an alkaline substance, moisture inhibits the transesterification reaction, so that the moisture content in animal and vegetable fats and oils is better. Therefore, before adding the catalyst, it is preferable to subject the animal and vegetable oils and fats to a dehydration step to reduce the water content in the animal and vegetable oils and fats to 0.1% by weight or less, more preferably 0.05% by weight. % Or less, more preferably 0.03% by weight or less, particularly preferably 0.01% by weight or less. Here, in order to dehydrate the animal and vegetable fats and oils, heating vacuum dehydration, nitrogen bubbling, or the like may be performed.

  When heating the animal and vegetable oils and fats before dehydrating the animal and vegetable oils and fats, the heating temperature is not particularly limited. For example, it may be heated to a temperature of about 60 to 110 ° C.

  As the alkaline substance used in the production of the transesterified oil of the present invention, any substance having transesterification ability may be used, and an alkali metal or a compound thereof can be exemplified. Specifically, potassium sodium Examples include alloys, sodium methylate, sodium ethylate, potassium methylate, sodium hydroxide, potassium hydroxide and the like. A potassium sodium alloy is preferable because of its high activity at low temperatures, and sodium methylate is preferable from the viewpoint of economy and ease of handling.

  The addition amount of the alkaline substance is preferably 0.05 to 0.5 parts by weight, more preferably 0.1 to 0.3 parts by weight with respect to 100 parts by weight of the animal and vegetable fats and oils. If the amount is less than 0.05 parts by weight, the transesterification rate of the animal or vegetable oil may be slow or the reaction may not proceed. On the other hand, if the amount is more than 0.5 parts by weight, the amount of soap produced by the reaction of monoglyceride, diglyceride, or triglyceride in the oil and fat with an alkaline substance increases, and the yield of the obtained transesterified oil decreases. It may not be preferable.

  The time and temperature in the reaction between the animal and plant oil and the alkaline substance are not particularly limited, and can follow a conventional method. For example, it is about 0.03 to 3 hours and about 50 to 120 ° C. Conditions for not mixing are good. For example, the reaction may be performed under vacuum, or the reaction may be performed in a state where the head space of the reaction vessel is filled with nitrogen.

<Second step: contact between oil and water after transesterification>
Droplet-like neutral water is added to the oil and fat after the transesterification reaction, and the water droplet is precipitated in the oil and fat. Thereby, the soap contained in fats and oils is moved to a water layer, and the amount of soap contained in fats and oils is reduced.

  Here, the neutral water includes water that is slightly alkaline and water that is slightly acidic but is not acidic enough to react with soap and change into fatty acid. Specifically, water having a pH in the range of 5 to 9 can be suitably used.

  To add the droplet-shaped neutral water to the fat or oil, the droplet-shaped neutral water is added to the fat or oil so that the total surface area of contact between the fat and neutral water after the transesterification reaction is large and emulsification hardly occurs. The method of adding to is preferable. If the total contact surface area is small, the cleaning efficiency may be poor. Moreover, when emulsification occurs, the yield of fats and oils may be reduced. The larger the water droplet size of neutral water, the more water droplets will settle according to the difference in specific gravity while holding the soap. Thereby, soap can be removed sufficiently and emulsification can be made difficult to occur.

  In order to make the balance between the sum of the contact surface area and the water droplet diameter within an appropriate range, specifically, a neutral water droplet is added to the oil so that the water droplet diameter in the oil layer is about 1 to 5 mm. Further, it is more preferable that the neutral water is added so as not to be too strong. If the water droplet diameter is smaller than 1 mm, the water droplets may continue to float in the fat and oil, making it difficult to settle. In addition, in order to contact the entire fat and oil in the oil layer, the momentum of adding neutral water becomes strong, so emulsification May be more likely to occur. When it is larger than 5 mm, the total contact surface area becomes small, and the removal of soap may be insufficient.

  When neutral water is added, if the neutral water is brought into contact with the oil and fat while stirring, a large amount of emulsified layer is generated between the water layer and the oil layer as described in JP-A-51-61510. And reduce the yield of fats and oils. Therefore, in order to suppress generation | occurrence | production of an emulsion layer as much as possible, it is preferable that the contact with fats and oils and neutral water is gentle. Regardless of the size of the water droplets described above, if the momentum when adding neutral water is too strong, emulsification may occur easily. If the momentum is too weak, it takes time to add neutral water, and production efficiency is increased. May decrease. Moreover, when adding neutral water to fats and oils, the one where the fluidity | liquidity of fats and oils is low is preferable, and it is still more preferable not to let fats and oils flow. The fluidity of the oil and fat may be adjusted by changing the stirring speed, for example.

  When adding neutral water from the upper part of fats and oils, the method of adding neutral water in droplet form by showering etc. can be illustrated, for example. The shower ring is easy to control the water droplet diameter by changing the nozzle diameter or adjusting the water pressure, and is suitable for increasing the total surface area of contact between the oil and fat after the transesterification reaction and neutral water. It is also easy to add neutral water uniformly over a wide range with respect to the surface of the oil layer. Furthermore, even if the water droplets to be added have a small particle size, the water droplets are likely to coalesce on the surface of the oil layer, so that they have an appropriate particle size and are likely to settle.

  The amount of neutral water to be brought into contact with the oil and fat after the transesterification reaction is preferably 10 to 200 parts by weight, more preferably 30 to 170 parts by weight, and more preferably 50 to 150 parts by weight with respect to 100 parts by weight of the raw animal and vegetable oils and fats. Part is more preferable, and 50 to 120 parts by weight is particularly preferable. If the amount is less than 10 parts by weight, the total surface area where neutral water and soap are in contact with each other is small, so that soap may not be sufficiently removed from the fat after the transesterification reaction. If the amount is more than 200 parts by weight, the amount of waste water that must be treated increases, which may be economically undesirable.

  By this step, a liquid containing the first aqueous layer and the first oil layer is obtained. Moreover, according to this process, compared with the conventional water washing process, generation | occurrence | production of an emulsion layer can be suppressed much. However, a slightly emulsified layer may be generated, and in this case, a liquid composed of the first aqueous layer, the emulsified layer and the first oil layer is obtained by this step. The emulsified layer is formed between the first aqueous layer and the first oil layer.

<Third step: removal of the first aqueous layer>
In this step, the first aqueous layer is removed from the liquid obtained in the second step. Moreover, as above-mentioned, when the emulsion layer has generate | occur | produced in the liquid obtained at the 2nd process, a 1st water layer and an emulsion layer are removed from the liquid obtained at the 2nd process. In this case, the emulsified layer may be removed together with the first aqueous layer.

  In the container such as a tank, the liquid obtained in the second step is separated into the first aqueous layer, the emulsified layer, and the first oil layer, if any, from below according to the difference in specific gravity. Therefore, the first aqueous layer and the emulsified layer can be removed from the liquid obtained in the second step by discharging the first aqueous layer and, if any, the emulsified layer from the lower part of the container. .

  The first aqueous layer, the emulsified layer, and the first oil layer are preferably sufficiently separated in advance before the removal of the first aqueous layer and the emulsified layer. If the separation of each layer is not sufficient, the removal efficiency of soap and emulsion may be reduced, or the yield of fats and oils may be reduced. In order to sufficiently separate the layers, for example, after settling of the added neutral water, the layers may be left in a container for a certain period of time or centrifuged.

  The transesterified oil obtained by removing the aqueous layer in this way has a very low soap content of 350 to 1200 ppm (preferably 350 to 1000 ppm). However, in order to prevent the occurrence of stagnation during high temperature deodorization, the transesterified oil is then subjected to decolorization treatment and / or contact treatment with acidic substances before deodorization in order to further reduce soap content. The previous soap content is preferably 15 ppm or less, more preferably 10 ppm.

  What is necessary is just to perform the said decoloring process according to a conventional method.

  The contact treatment with the acidic substance is to mix and stir the acidic substance in the first oil layer after removing the first aqueous layer and the emulsified layer, if any, in the third step. Thereby, soap can be decomposed | disassembled by changing the soap remaining in the 1st oil layer into a fatty acid. Here, the agitation represents making the oil layer and the acidic substance into a turbulent state. In order to create a turbulent state, for example, a stirring blade may be rotated in a tank or a static mixer may be passed.

  The acidic substance is not particularly limited as long as it is an acidic substance that can take an alkali metal from soap and change it into a fatty acid when reacted with soap. For example, organic acids such as citric acid, malic acid and lactic acid, and inorganic acids such as hydrochloric acid and sulfuric acid can be exemplified, but considering that it is edible, organic acids are preferable.

  When adding the said acidic substance to a 1st oil layer, adding in the state of aqueous solution is preferable. The reason for this is that when an acidic substance is added in a solid state, the reaction with soap in the oil or fat does not proceed efficiently, and when an acidic substance is added in the form of a gas, the reaction quickly takes place out of the oil and fat. It is because it does not advance to.

  When the acidic substance is added in the form of an aqueous solution, after the mixing and stirring of the acidic substance aqueous solution and the first oil layer are completed, the oil layer and the aqueous layer are sufficiently separated, and then the aqueous layer is removed. Thereby, the fatty acid produced by the reaction between soap and acidic substance can be removed together with the aqueous layer. In this step, an emulsified layer may be slightly generated even in a very small amount. In this case, a liquid composed of an aqueous layer, an emulsified layer and an oil layer is obtained. Since the emulsified layer is formed between the aqueous layer and the oil layer, when the emulsified layer is generated, the emulsified layer may be removed together with the aqueous layer.

  In order to separate the oil layer and the water layer, for example, the oil layer and the aqueous layer may be allowed to stand for a certain period of time after completion of stirring or may be centrifuged. Other methods for removing moisture in the oil layer include vacuum and heat dehydration, but a large amount of heat is required to evaporate much of the moisture, and it takes a lot of time to remove, Since oxidation stability and flavor may be impaired, it is not preferable.

  Furthermore, the residual acidic substance in the oil layer may be removed after removing the aqueous layer. If the melting point of the added acidic substance is lower than the temperature of the oil or fat, removing the aqueous layer and then performing vacuum dehydration may cause the acidic substance to precipitate as crystals in the oil layer. For example, passing the oil layer through a filter, etc. It is possible to remove acidic substances by this method. Moreover, as a method for removing the acidic substance without precipitating, after removing the aqueous layer, further removing the acidic substance in a dissolved state in the aqueous layer by removing the aqueous layer obtained by centrifugation. Alternatively, a method of removing the acidic substance obtained in the lower layer of the oil and fat after centrifugation using the difference in specific gravity between the oil and fat and the acidic substance is also possible. In the case of this method, the water layer may be removed and then water may be added again before centrifugation. Further, when the added acidic substance is an acid having a low boiling point such as hydrochloric acid, the acidic substance is volatilized and can be removed when the oil layer is distilled.

<Fourth process: Deodorizing treatment>
In this step, the first oil layer is subjected to a deodorization step to obtain an edible fat that is a transesterified oil. The deodorization is performed by, for example, transferring the first oil layer to a steam distillation apparatus and heating the first oil layer under a reduced pressure of 400 Pa or less at a rate of 0.5 to 10 parts by weight / hr with respect to 100 parts by weight of the first oil layer. It can be done by blowing.

  Moreover, 180-260 degreeC is preferable, as for the deodorizing temperature by the said steam distillation, 190-250 degreeC is more preferable, 200-240 degreeC is still more preferable, 210-240 degreeC is especially preferable. If it is lower than 180 ° C., the free fatty acid contained in the transesterified oil cannot be removed, the acid value becomes high, and the resulting fats and oils may leave a bitter taste such as gummy. When it is higher than 260 ° C., there may be a case where a decrease in oxidation-stable substances in fats and oils and a good flavor component are removed. The acid value is preferably 0.1 or less, more preferably 0.07 or less, and still more preferably 0.05 or less. If the acid value is 0.07 or less, it can be said that the deodorization of the transesterified oil is sufficient. In actual production, the lower limit of the acid value is 0.02.

  The deodorization time by the steam distillation is preferably 20 to 60 minutes, more preferably 30 to 50 minutes, and further preferably 40 to 50 minutes. If it is shorter than 20 minutes, the free fatty acid contained in the transesterified oil cannot be removed, and the resulting oil or fat may have an acid value that is high, or may have a bitter taste. If it is longer than 60 minutes, there may be a decrease in oxidation-stable substances in the fats and oils and removal of good flavor components.

  As the deodorization, a thin-film distillation method can be used, and the deodorization temperature and deodorization time in that case may be appropriately performed in accordance with a conventional method.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the examples, “parts” and “%” are based on weight.

<Measurement method of soap amount in oil reservoir>
The amount of soap in the oil layer was measured according to the method described in 2.6.2-1996 soap of “Reference Oil Analysis Method” (issue year: 1996) edited by Japan Oil Chemical Association.

<Acid value>
The acid value was measured according to the standard oil analysis method “2.3.1-1996 acid value” of “Standard Oil Analysis Method” (issue year: 1996) edited by the Japan Oil Chemical Association.

(Example 1) Preparation of transesterified oil 1 to be subjected to deodorization treatment 100 parts by weight of palm fractionated oil (iodine number: 60, melting point: 17 ° C) was placed in a separable flask and stirred at a stirring speed of 150 rpm. Heat vacuum dehydration was performed under the condition of a vacuum degree of 400 Pa, and the water content in the oil was adjusted to 0.0085% by weight. Thereafter, 0.15 parts by weight of sodium methylate was added to 100 parts by weight of the oil and fat, and the mixture was stirred for 20 minutes while maintaining the vacuum state. After the stirring was stopped and the vacuum was released, 100 parts by weight of neutral water (pH 7.6 (hereinafter all the same pH)) was showered from the top of the oil layer with respect to 100 parts by weight of the palm fractionated oil. While pouring, the oil and water were brought into contact with each other, and water droplets were settled in the oil and fat. At this time, the oil layer is not stirred. Moreover, almost no emulsification occurred. The mixture was allowed to stand for 40 minutes to sufficiently separate the oil layer, the emulsified layer, and the aqueous layer, and then the aqueous layer and the emulsified layer were discharged from the bottom of the flask to obtain 98 parts by weight of transesterified oil 1 for deodorization treatment. The transesterified oil 1 contained 500 ppm of soap, and the yield of fats and oils was as good as 98.0% by weight.

(Example 2) Production of transesterified oil 2 to be subjected to deodorization treatment 100 parts by weight of palm fractionated oil (iodine value: 52, melting point 33 ° C) was put into a separable flask and stirred at a stirring speed of 150 rpm, 100 ° C, Dehydration was performed under the condition of a vacuum degree of 1000 Pa, and the water content in the fat was adjusted to 0.025% by weight. Thereafter, 0.25 parts by weight of sodium methylate was added to 100 parts by weight of the fat and oil, and the mixture was stirred for 30 minutes in a vacuum state. After the stirring was stopped and the vacuum was released, 140 parts by weight of neutral water was poured from above the oil layer while showering to bring the oil and water into contact with each other, thereby allowing water droplets to settle in the oil. At this time, the oil layer is not stirred. Moreover, almost no emulsification occurred.

  After leaving still for 40 minutes to sufficiently separate the oil layer, the emulsified layer, and the aqueous layer, the aqueous layer and the emulsified layer are discharged from the bottom of the flask, and 97.2 parts by weight of the transesterified oil 2 for deodorization treatment is obtained. Obtained. The transesterified oil 2 contained 450 ppm of soap, and the yield of fats and oils was as good as 97.2% by weight.

(Example 3) Production of transesterified oil 3 to be subjected to deodorization treatment 100 parts by weight of pork fat (melting point: 37 ° C) was put in a separable flask and stirred at a stirring speed of 150 rpm, under conditions of 100 ° C and a degree of vacuum of 670 Pa. The water content in the fat was adjusted to 0.015% by weight. Thereafter, 0.18 parts by weight of sodium methylate was added to 100 parts by weight of the oil and fat, and the mixture was stirred for 25 minutes in a vacuum state. After the stirring was stopped and the vacuum was released, 80 parts by weight of neutral water was poured from above the oil layer while showering to bring the oil and water into contact with each other, thereby allowing water droplets to settle in the oil. At this time, the oil layer is not stirred. Moreover, almost no emulsification occurred. After leaving still for 40 minutes to sufficiently separate the oil layer, the emulsified layer, and the aqueous layer, the aqueous layer and the emulsified layer are discharged from the bottom of the flask, and 97.8 parts by weight of the transesterified oil 3 for deodorization treatment is obtained. Obtained. The transesterified oil 3 contained 750 ppm of soap, and the yield of fats and oils was as good as 97.7% by weight.

(Comparative example 1) Preparation of transesterified oil 4 to be subjected to deodorization treatment 100 parts by weight of soybean oil was put into a separable flask, and dehydrated under conditions of 100 ° C and a vacuum of 1000 Pa while stirring at a stirring speed of 150 rpm. The water | moisture content in fats and oils was adjusted to 0.017 weight%. Thereafter, 0.20% by weight of sodium methylate was added, the mixture was stirred for 20 minutes in a vacuum state, the vacuum was released, and 99.8 parts by weight of transesterified oil 4 for deodorization treatment was obtained. The transesterified oil contained a large amount of soap at 48000 ppm, and the yield of fats and oils was 95.0% by weight.

(Comparative Example 2) Preparation of transesterified oil 5 to be subjected to deodorization treatment in accordance with the method described in JP-A-51-61510. 100 parts by weight of soybean oil was placed in a separable flask and stirred at a stirring speed of 150 rpm. Dehydration was performed under conditions of 100 ° C. and a vacuum degree of 400 Pa, and the water content in the fats and oils was adjusted to 0.0074% by weight. Thereafter, 0.15% by weight of sodium methylate was added and stirred for 20 minutes in a vacuum state. After releasing the vacuum, 100 parts by weight of water was poured from above the oil layer while being stirred while stirring the oil layer at a stirring speed of 150 rpm. At this time, emulsification occurred violently, and water droplets did not settle quickly in the oil. After leaving still for 90 minutes to separate the oil layer, the emulsified layer and the water layer as much as possible, the water layer and the emulsified layer are discharged from the bottom of the flask to obtain 88.7 parts by weight of the transesterified oil 5 to be subjected to deodorization treatment. It was. The transesterified oil contained 1600 ppm of soap and the soap could be removed to some extent, but the yield of fats and oils was as low as 88.6% by weight.

(Comparative Example 3) Production of transesterified oil 6 to be subjected to deodorization treatment 100 parts by weight of soybean oil was put into a separable flask and dehydrated at 100 ° C and a vacuum of 1000 Pa while stirring at a stirring speed of 150 rpm. Was adjusted to 0.018% by weight. Thereafter, 0.2% by weight of sodium methylate was added and stirred for 20 minutes in a vacuum state. After releasing the vacuum, 8 parts by weight of water was showered and poured from above the oil layer while stirring the oil layer at 20 rpm. At this time, almost no emulsification occurred. After leaving still for 40 minutes to sufficiently separate the oil layer, the emulsified layer and the aqueous layer, the aqueous layer and the emulsified layer are discharged from the bottom of the flask to obtain 98.9 parts by weight of the transesterified oil 6 for deodorization treatment. It was. The transesterified oil contained 21000 ppm of soap, the amount of soap remaining was large, and the yield of fats and oils was 96.8% by weight.

(Reference Example 1) Contact treatment and deodorization of transesterified oil 1 with an acidic substance 0.017 wt.% In 98 wt.% Water with respect to 98 wt.% Of transesterified oil 1 subjected to the deodorizing treatment obtained in Example 1 A citric acid aqueous solution in which a part of citric acid was dissolved was added, and the mixture was stirred for 60 minutes under conditions of 150 rpm, 80 ° C. and normal pressure, and then allowed to stand. After 35 minutes from the start of standing, 90% of the water had settled in the aqueous layer. At this time, emulsification did not occur. After 45 minutes from the start of standing, the water layer was discharged from the bottom of the flask, and while stirring at a stirring speed of 150 rpm, heat vacuum dehydration was performed under conditions of 100 ° C. and a vacuum of 400 Pa, and the moisture in the oil and fat was 0.01 weight. %, And passed through a filter paper (Advantec qualitative filter paper No. 1) to remove precipitated citric acid, thereby obtaining 97.5 parts by weight of a transesterified oil having a soap concentration of 0 ppm.

  A total of 97.5 parts by weight of the transesterified oil after treatment with citric acid was charged into a steam distillation apparatus, and deodorized under conditions of 210 ° C., vacuum degree of 270 Pa, steam blowing amount of 2 wt% / hr, 45 minutes, 96 Obtained 5 parts by weight of transesterified oil. The acid value of the obtained transesterified oil was 0.03, a favorable flavor was felt, there was no off-flavor and off-flavor, and it was preferable as the flavor of the transesterified oil. Moreover, since the adsorbent was not used, the value of adsorbent / transesterified oil (weight ratio,%) was 0. The evaluation results including them are summarized in Table 2.

(Reference Example 2) Contact treatment of transesterified oil 2 with acidic substance, clay treatment and deodorization For 97.2 parts by weight of transesterified oil 2 obtained in Example 2, 0.0085 in 200 parts by weight of water. An aqueous citric acid solution in which parts by weight of citric acid was dissolved was added, and the mixture was stirred for 60 minutes under conditions of 150 rpm, 80 ° C. and normal pressure, and then allowed to stand. After 40 minutes from the start of standing, 90% of the water was precipitated, and the precipitated water layer was removed 50 minutes after the start of standing. At this time, emulsification did not occur. Thereafter, the moisture in the oil and fat is adjusted to 0.01 wt% by heating under vacuum dehydration under conditions of 100 ° C and a vacuum degree of 400 Pa, passed through a filter paper (Advantec qualitative filter paper No1) to remove the precipitated citric acid, 96.2 parts by weight of an oil layer having a concentration of 35 ppm was obtained.

  96.2 parts by weight of the total oil layer after treatment with citric acid was put in a separable flask, 0.38 parts by weight of activated clay was added, and the mixture was stirred for 20 minutes at 90 ° C., 150 rpm, and a vacuum of 1330 Pa. After adjusting the water content of the entire mixture to 1 wt%, the white clay was separated to obtain 95.8 parts by weight of transesterified oil having a soap concentration of 0 ppm.

  After the white clay treatment, the entire amount of the transesterified oil after further separating the white clay was charged into a steam distillation apparatus, and the steam blowing amount was 2 parts by weight / hr for 45 minutes at 230 ° C., a vacuum of 270 Pa, and 100 parts by weight of the transesterified oil. The deodorization process was carried out under the above conditions to obtain 94.7 parts by weight of a transesterified oil and fat. The acid value of the obtained transesterified oil was 0.04, a favorable flavor was felt, there was no off-flavor and off-flavor, and the flavor of the transesterified oil was preferable. Moreover, 0.4 weight part of fats and oils adhered to the separated clay, and the value of waste adsorbent / transesterified oil (weight ratio,%) was 0.82. The evaluation results including them are summarized in Table 2.

(Reference Example 3) Contact treatment and deodorization of transesterified oil 3 with an acidic substance 0.05 parts by weight of 400 parts by weight of water with respect to 97.8 parts by weight of transesterified oil 3 obtained in Example 3 A malic acid aqueous solution in which malic acid was dissolved was added, and the mixture was stirred at 150 rpm, 90 ° C. and normal pressure for 40 minutes, and then allowed to stand. After 30 minutes from the start of standing, 90% of the water settled and the oil layer and water layer were sufficiently separated, so the water layer was removed as it was. At this time, emulsification did not occur. Then, the moisture in the fats and oils was adjusted to 0.01 wt% by heating and vacuum dehydration under the conditions of 100 ° C and a degree of vacuum of 400 Pa, passed through a filter paper (Advantec qualitative filter paper No1), the precipitated malic acid was removed, and the soap concentration 97.3 parts by weight of 0 ppm transesterified oil was obtained.

  A total of 97.3 parts by weight of the oil layer after the treatment with malic acid was charged into a steam distillation apparatus, treated under a deodorizing condition of 220 ° C., a vacuum degree of 270 Pa, a steam blowing amount of 3 parts by weight / hr for 40 minutes, and 96.5 weights. Part transesterified oil was obtained. The acid value of the obtained transesterified oil 3 was 0.03, a favorable flavor was felt, there was no off-flavor and off-flavor, and it was preferable as the flavor of the transesterified oil. Moreover, since the adsorbent was not used, the value of the waste adsorbent / transesterified oil (weight ratio,%) was 0. The evaluation results including them are summarized in Table 2.

(Reference Example 4) Contact treatment and deodorization of transesterified oil 4 with an acidic substance 92.2 parts by weight of transesterified oil used in the deodorization treatment obtained in Comparative Example 1 was 1.22 wt.% In 80 parts by weight of water. A malic acid aqueous solution in which a part of malic acid was dissolved was added, and the mixture was stirred for 40 minutes under conditions of 150 rpm, 90 ° C. and normal pressure, and then allowed to stand. After 40 minutes from the start of standing, 90% of the water settled down in the aqueous layer. After discharging the aqueous layer from the bottom of the flask as it was, stirring was performed at a stirring speed of 150 rpm, under conditions of 100 ° C. and a vacuum of 400 Pa. Heat dehydration was performed to adjust the water content in the oil to 0.01% by weight. Subsequently, the precipitated malic acid was removed by passing through a filter paper (Advantec qualitative filter paper No1) to obtain 96.8 parts by weight of transesterified oil having a soap concentration of 0 ppm.

  The whole amount of transesterified oil after malic acid treatment was charged into a steam distillation apparatus, deodorized under conditions of 250 ° C., vacuum degree of 270 Pa, steam blowing amount of 2 parts by weight / hr, 45 minutes, and 96.0 parts by weight of transesterified oil and fat. Got. The acid value of the obtained transesterified oil and fat was as high as 0.18, and the flavor was clearly felt with an off-flavored taste. Moreover, since the adsorbent was not used, the value of the waste adsorbent / transesterified oil (weight ratio,%) was 0. The evaluation results including them are summarized in Table 2.

(Reference Example 5) Decolorization and deodorization of transesterified oil 6 After the transesterified oil 6 to be subjected to the deodorizing treatment obtained in Comparative Example 3 was put into a 98.9 parts by weight separable flask, 15 parts by weight of activated clay was added. , 90 ° C, 150 rpm, vacuum degree of 1330 Pa, stirring for 40 minutes to make a vacuum state, adjust the water content of the whole mixture to 0.01 wt%, separate the white clay and ester with a soap concentration of 8 ppm 59.8 parts by weight of exchange oil was obtained.

  The total amount of the transesterified oil was charged into a steam distillation apparatus and subjected to deodorization treatment under the conditions of 250 ° C., vacuum degree of 270 Pa, steam blown amount of 2 parts by weight / hr, and 60 minutes to obtain 57.9 parts by weight of transesterified oil and fat. The acid value of the obtained transesterified oil / fat was 0.08, and the taste was clearly felt as having a different taste and smell. Moreover, the value of waste adsorbent / transesterified oil (weight ratio,%) was as high as 39.1, and many waste adsorbents to be treated were generated. The evaluation results including them are summarized in Table 2.

Claims (2)

The first step of subjecting animal and vegetable oils and fats to a transesterification reaction using an alkaline substance,
By adding 10 to 200 parts by weight of neutral water droplets to 100 parts by weight of the animal and vegetable oils and fats obtained after the transesterification reaction, the water droplets are precipitated in the oils and fats. A second step of obtaining a liquid comprising an aqueous layer and a first oil layer;
The manufacturing method of the transesterification oil for using for the deodorizing process including the 3rd process which removes a 1st aqueous layer from the liquid obtained at the 2nd process, and obtains residual transesterification oil 350-1200 ppm.   The method for producing transesterified oil according to claim 1, wherein the adsorbent used for the decolorization treatment is a white clay before the deodorization treatment.