JPWO2013062114A1 - Cooking oil - Google Patents

Abstract

Palm oil and fat is the main raw material, the SU2 / UUU weight ratio is 1.9 or less, the SSS content is 2% by weight or less, and 10-30% by weight of glyceride bonded with palmitic acid at the 2-position is contained in the whole liquid oil. By using liquid oil derived from palm oil, it is the same as when using expensive high-oleic sunflower oil or high-oleic rapeseed oil. In addition, since no crystals are generated during storage, a cooking oil that is easy to use can be obtained at a low cost. In addition, cooking oil having good absorbability can be obtained. [Selection figure] None

Description

  The present invention relates to a cooking oil used for frying and the like.

  Oxidation stability and thermal stability are listed as characteristics required for frying fats and oils, but in recent years, frying fats and oils that have a good flavor and are not odorous, making use of the flavors of the ingredients of fried foods, are desired. .

  Conventionally, as cooking oil used for frying, various liquid oils such as soybean oil, rapeseed oil, palm olein, high oleic sunflower oil, high oleic rapeseed oil have been used. However, soybean oil and rapeseed oil are easy to use because they are highly liquid and do not generate crystals, but when used as frying oil, they have low oxidative stability, fats and oils deteriorate, and the flavor deteriorates, so it can withstand long-term use. I can't. When palm olein is used for frying fats and oils, it has high oxidation stability and is less likely to deteriorate in flavor and can withstand long-term use, but crystals are generated at low temperatures and are difficult to use. When high oleic sunflower oil or high oleic rapeseed oil is used, the liquidity and oxidation stability are good, but there is a problem that the price is high.

  As oils for frying using cheap palm oil as raw material, oils that are liquid at 0 ° C such as soybean oil, rapeseed oil, high oleic rapeseed oil, corn oil, safflower oil, sunflower oil, cottonseed oil, linseed oil, etc. 10 ~ 90% by mass, 9.9-89.9% by mass of the oil obtained by subjecting palm oil and fat and liquid oil at 0 ° C. to transesterification, and further subjecting the obtained transesterified oil to dry fractionation And 0.1 to 5% by mass of fat and oil consisting of rapeseed extremely hardened oil having a saturated fatty acid content of 22 carbon atoms (behenic acid content) of 20 to 60% by mass in all constituent fatty acids, and having fluidity at 25 ° C. An oil composition for frying has been proposed (Patent Document 1). However, this oil composition for frying also produces crystals at low temperatures and is difficult to use, like palm olein.

  As described above, until now, when palm oils and fats were used as raw materials and used as frying oils, they could withstand long-term use, did not generate crystals at low temperatures, and were not easy to use.

  In addition, triglyceride having palmitic acid bonded to β-position (2nd position) is known to exhibit much higher absorbability than triglyceride having palmitic acid bonded to α-position (1,3rd position) (patent) Reference 2). However, the solid fat and the liquid oil that are filtered when producing liquid oil using palm oil as a raw material are mostly palmitic acid as a constituent fatty acid, but most of them are bonded to positions 1 and 3, It does not show high absorbency.

JP 2005-160453 A Japanese Patent Laid-Open No. 6-70786

  In view of the problems in the cooking oils and fats such as the conventional frying fats and oils as described above, the present invention is resistant to bad taste when fried and can withstand long-term use, and crystals are not generated at low temperatures. An object is to provide cooking oil that is easy to use at low cost.

  As a result of intensive studies to solve the above problems, the inventors of the present invention have palm oils and fats as a main raw material, the SU2 / UUU weight ratio is 1.9 or less, and the SSS content is 2% by weight or less. By using a palm oil-derived liquid oil containing 10-30% by weight of glyceride to which palmitic acid is bound in the whole liquid oil, from expensive palm oil, expensive high oleic sunflower oil and high oleic rapeseed oil were used. Degradation of oil and fat during frying is suppressed, the flavor is hardly deteriorated, it can be used for a long time, and crystals are not generated during low-temperature storage, so that cooking oil that is easy to use can be obtained. As a result, the present invention has been completed.

  That is, in the present invention, glyceride containing palm oil and fat as a main raw material, having a SU2 / UUU weight ratio of 1.9 or less and an SSS content of 2% by weight or less and having palmitic acid bonded in the second position is 10 to 30 in the whole liquid oil. The present invention relates to a cooking oil containing 40% to 100% by weight of a palm oil-derived liquid oil containing 40% by weight of the whole cooking oil. A preferred embodiment relates to the cooking oil as described above, wherein the cloud point of the palm oil-derived liquid oil is 0 to -12 ° C. Moreover, a preferable embodiment is related with the said cooking oil whose said CDM value of the said palm oil origin liquid oil is 5 hours or more.

  According to the present invention, deterioration of fats and oils at the time of frying is suppressed, the flavor is hardly deteriorated, and it can be used for a long time, and since no crystal is generated at low temperature storage, a cooking oil that is easy to use can be obtained. . In addition, according to the present invention, cooked cooking oil with good absorbability can also be obtained.

  The cooking oil according to the present invention uses glyceride in which the palm oil is the main raw material, the SU2 / UUU weight ratio is 1.9 or less, the SSS content is 2% by weight or less, and palmitic acid is bonded to the 2-position in the whole liquid oil. It is preferable to contain 10 to 30% by weight of the palm oil-derived liquid oil contained in the whole cooking oil by heating in an amount of 40 to 100% by weight.

  Hereinafter, the palm oil origin liquid oil used for the cooking oil of this invention is demonstrated.

The fatty acid composition of triglyceride in the present invention is abbreviated as follows.
S: saturated fatty acid, U: unsaturated fatty acid SSS: trisaturated fatty acid glyceride SU2: monosaturated fatty acid diunsaturated fatty acid glyceride S2U: disaturated fatty acid monounsaturated fatty acid glyceride UUU: triunsaturated fatty acid glyceride

In the present invention, the method for measuring each triglyceride content is as follows.
<Measurement of each triglyceride content in fats and oils>
Each triglyceride content in fats and oils is determined using AOCS Official using HPLC.
It measured based on Method Ce 5c-93, and it calculated from the retention time and area ratio of each peak. The analysis conditions are described below.
Eluent: Acetonitrile: Acetone (70:30, volume ratio)
Flow rate: 0.9 ml / min Column: ODS
Column temperature: 36 ° C
Detector: Differential refractometer

Furthermore, in the present invention, the method for measuring the fatty acid composition in the fat is as follows.
<Measurement of fatty acid composition in fats and oils>
The fatty acid composition in the oil and fat can be measured by the FID constant temperature gas chromatograph method. The FID constant temperature gas chromatograph method is a method described in “2.4.2.1 Fatty acid composition” of “Standard oil analysis test method” (issue year: 1996) edited by Japan Oil Chemistry Association.

  The palm oil-derived liquid oil used in the present invention is made of palm oil and fat, preferably palm oil and fat having an iodine value of 55 or more as a main raw material, has a specific fatty acid composition, and has low liquidity and high oxidation stability. Liquid oil. The palm oil and fat is not particularly limited as long as it is derived from palm oil, and examples thereof include palm refined oil, unrefined crude oil, and fractionated oil and fat such as palm olein obtained by one or more fractionations. .

  The palm oil origin liquid oil used by this invention can be manufactured by the direct transesterification reaction of palm oil fat.

  The saturated fatty acid content in the total constituent fatty acids of the palm oil used as a raw material is preferably 70% by weight or less, more preferably 3 to 70% by weight, still more preferably 3 to 52% by weight, particularly preferably 30 to 30%. 52% by weight. If the saturated fatty acid content is more than 70% by weight, there will be too many hard parts during direct transesterification, and it will be difficult to obtain crystals with good separability. It may be difficult to obtain. However, if the saturated fatty acid content is less than 3% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much. A preferred embodiment of palm oil is palm olein. The said palm olein in this invention refers to the thing obtained by isolate | separating the fats and oils extract | collected from the pulp of palm, and an iodine number is 55 or more.

  When manufacturing the palm oil origin liquid oil used by this invention, in addition to palm type fats and oils, you may further use fats and oils other than palm type fats and oils as raw material fats and oils. However, in order to further enjoy the effects of the present invention, the content of fats and oils other than palm-based fats and oils is preferably as small as possible, preferably 50% by weight or less, more preferably 30% by weight or less, and still more preferably 10%. % By weight or less, most preferably 0% by weight. If the content of fats and oils other than palm-based fats and oils is more than 50% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much.

  As fats and oils other than palm-based fats and oils used for the production of palm oil-derived liquid oil, the SU2 / UUU weight ratio in the finally obtained liquid oil is 1.9 or less, more preferably 1.1 or less, and the SSS content is There is no particular limitation as long as it is an edible oil and fat of 2% by weight or less. Examples of such fats are soybean oil, rapeseed oil, sunflower oil, olive oil, sesame oil, canola oil, cottonseed oil, rice bran oil, safflower oil, palm oil, palm kernel oil, shea fat, monkey fat, lippe Fats, cacao butter, beef fat, pork fat, milk fat, fractionated fats and oils of these fats, hardened fats and oils, transesterified fats and the like, and the like. Among these, soybean oil and rapeseed oil having a saturated fatty acid content of less than 20% by weight in the total constituent fatty acids are preferable because the effects of the present invention are easily exhibited.

  The saturated fatty acid content in the total constituent fatty acids of the fats and oils other than the palm-based fats and oils is preferably 70% by weight or less, more preferably 3 to 70% by weight, for the same reason as described for the palm-based fats and oils. More preferably, it is 3 to 52% by weight.

  The triglyceride composition of the palm oil-derived liquid oil used in the present invention preferably has a SU2 / UUU weight ratio of 1.9 or less, more preferably less than 1.3, and even more preferably 1.1 or less. The SU2 / UUU weight ratio is preferably 1.0 or less, more preferably 0.95 or less, 0.9 or less, 0.8 or less, 0.7 or less, Hereinafter, the smaller the value, 0.5 or less, the more preferable. On the other hand, in view of ease of production and oxidation stability, the lower limit of the SU2 / UUU weight ratio is preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.65 or more, and 7 or more is particularly preferable. In consideration of the balance between liquidity and ease of production, the SU2 / UUU weight ratio is preferably in the range of 1.1 to 0.5, more preferably 1.0 to 0.6, and 0.95 to 0. .65 is more preferable, and 0.9 to 0.7 is most preferable.

  The SSS content in the palm oil-derived liquid oil used in the present invention is preferably as small as possible, and the SSS content of the liquid oil is preferably 2% by weight or less, and 0.5% by weight or less. Is more preferably 0.3% by weight or less, particularly preferably 0.1% by weight or less, extremely preferably 0.05% by weight or less, and 0.03% by weight or less. Most preferred. When the SSS content of the liquid oil exceeds 2% by weight, the liquid oil may not be used as a substitute for a commonly used liquid oil.

  Furthermore, in order to maintain the liquid property of the palm oil origin liquid oil used by this invention, it is preferable that S2U content is 0.5 to 10 weight% in the whole liquid oil. The S2U content is more preferably 1.0 to 10.0% by weight, still more preferably 2.0 to 9.5% by weight, particularly preferably 3.0 to 9.0% by weight, and 4.0 to 8.%. 5% by weight is most preferred. For the same reason as above, the UUU content is preferably 12% by weight or more, more preferably 25% by weight or more, further preferably 35% by weight or more, and 40% by weight or more. Is most preferred.

  The palm oil-derived liquid oil used in the present invention has a high content of glyceride bound to palmitic acid at the 2-position, which is generally said to be highly absorbent, considering the absorbability of the oil impregnated in the food during frying. However, considering the liquidity, it is preferably 10 to 30% by weight, more preferably 13 to 30% by weight, further preferably 16 to 30% by weight, particularly preferably 16 to 25% by weight, and 16 to 20% by weight. Most preferred.

  The content of polyunsaturated fatty acids in the palm oil-derived liquid oil used in the present invention is preferably as low as possible from the viewpoint of oxidation stability, preferably 22% by weight or less, more preferably 21% by weight or less, and 20% by weight or less. More preferred is 19% by weight or less, particularly preferred is 18% by weight or less, and most preferred is 17% by weight or less. In order to reduce the amount of polyunsaturated fatty acids, the timing for stopping the direct transesterification described later may be advanced or the fractionation temperature may be increased.

  Further, the cloud point of the palm oil-derived liquid oil used in the present invention is not particularly problematic as long as the liquid oil composition is satisfied, but from the viewpoint of liquidity, 0 ° C to -12 ° C is preferable, and -2 ° C to −12 ° C. is more preferable, −2.5 ° C. to −12 ° C. is more preferable, and 0 ° C. to −10 ° C. is preferable and 0 ° C. to −9 ° C. is more preferable from the viewpoint of ease of production and oxidation stability. .

  Further, the palm oil-derived liquid oil used in the present invention preferably has a CDM value of 5 hours or more, more preferably 6 hours or more, and even more preferably 7 hours or more (CDM: Conductometric Determination Method, “Standard Oil Analysis Test Method”. 2.5.1.2-1996 CDM test "). The palm oil-derived liquid oil used in the present invention has a high CDM value and excellent oxidation stability as described above.

  There are two methods for producing the palm oil-derived liquid oil used in the present invention. The first production method is characterized in that the direct transesterification reaction is stopped in order to obtain a composition in which crystals with high separability are likely to be generated during crystallization. In addition, the second production method is characterized in that crystals having good separability are produced during the direct transesterification reaction, and thereafter fractionation is performed without dissolving all the crystals.

  In the first production method, the raw oil and fat is used, and as the SSS / S2U in the fat and oil increases, crystals with high separability are more likely to be generated and the separation efficiency increases, so that the SSS / S2U becomes 0.5 or more. The direct transesterification reaction is performed until the reaction is stopped, and then the hard part is separated and removed. SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction. In a preferred embodiment, the direct transesterification reaction using palm-based fats and oils having a saturated fatty acid content of 70% by weight or less in the whole constituent fatty acids as a main raw material, and at least 31% by weight of the SSS content in the oil / fat composition during the reaction. It is preferable to carry out until the S2U content is 14% by weight or less and the reaction is stopped without exceeding. If the above is satisfied, any number of direct transesterification reactions may be performed. However, considering the cost, it is preferable to stop the transesterification immediately if the above is satisfied.

  In the second production method, the above-described raw material fats and oils are used, a direct transesterification reaction is performed while flowing the fats and oils by applying force from the outside, and then the solid fat content is separated without making it 1% or less. . In a preferred embodiment, the direct transesterification reaction is performed until the SSS / S2U in the fat becomes 0.5 or more. SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction. Moreover, it is more preferable that the SSS content in the oil and fat composition during the direct transesterification reaction does not exceed 31% by weight, and it is even more preferable that the S2U content be 14% by weight or less.

  In order to apply the force from the outside to flow the oil and fat, various methods such as stirring, passing the oil and fat through a reaction tube or the like with an external pressure such as a pump, or dropping naturally from a high place can be adopted. Specifically, in order to stir, the oils and fats to be reacted are fluidized by using an apparatus such as a tank or a pin machine having a stirring blade. In order to pass fats and oils through a reaction tube or the like with an external pressure such as a pump, the fats and oils to be reacted can be flowed by means such as a static mixer. If direct transesterification is performed without applying external force such as stirring at the start of the reaction or in the middle of the reaction without causing the oil or oil to flow, crystals with poor separability will be produced, and the oil or fat during the reaction will be solid. And separation may be difficult.

  In the second production method in which a direct transesterification reaction is performed by applying a force from the outside to cause the oil to flow, in order to further improve the liquidity, crystallization is performed after the direct transesterification reaction and before the fractionation treatment. In order to increase the yield, it is preferable to raise the temperature. However, when only raising the temperature without crystallization, the liquidity may be lowered. The condition for raising the temperature is to prevent the solid fat content from becoming 1% by weight or less. If the temperature is raised until the solid fat content is 1% by weight or less, the heating cost increases, and the effect as a seed crystal may be lost when crystallization is performed. The crystallization rate is preferably 0.01 ° C / min to 5 ° C / min, more preferably 0.1 ° C / min to 2 ° C / min. If the crystallization rate is out of the above range, the separation of the generated crystals may be poor.

  The direct transesterification reaction in the present invention is a reaction in which transesterification is carried out while generating fat crystals under a catalyst having transesterification ability. The direct transesterification method in the present invention may be either a batch type or a continuous type. Furthermore, the direct transesterification reaction may be cyclic. As the cyclic direct transesterification reaction, for example, SSS and SS (diglyceride composed of two saturated fatty acids) precipitated in the palm oil and fat deposited in the raw material oil tank A adjusted to a specific temperature are precipitated, and the supernatant liquid is obtained. Is continuously transferred to the transesterification apparatus B (1), and in the transesterification apparatus B, the transferred supernatant is transesterified at the optimum temperature of the lipase and then transferred again to the feed oil tank A. By repeating the step (2), the direct transesterification reaction is performed until the SSS / S2U in the fats and oils in the raw material oil tank A becomes 0.5 or more. More preferably, the SSS / S2U in the fat is 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, most preferably, the SSS / S2U in the fat is 2 Direct transesterification reaction is carried out until it becomes 0 or more. More preferably, the direct transesterification reaction is carried out until the S2U content is 14% by weight or less without the SSS content in the oil or fat exceeding 31% by weight. Thereafter, the reaction fats and oils in the raw material oil tank A are separated into liquid oil (soft part) and solid fat (hard part).

  The catalyst used for the direct transesterification reaction is not particularly limited, and any catalyst such as a chemical catalyst or an enzyme catalyst may be used as long as it has transesterification ability. Among the chemical catalysts, potassium sodium alloy is preferable because of its high activity at low temperatures, and sodium methylate is more preferable because of economy and ease of handling. The amount of the chemical catalyst used is not particularly limited, and may be an amount used in ordinary transesterification, but is preferably 0.01 to 1 part by weight with respect to 100 parts by weight of the raw material fat and oil from the viewpoint of reaction efficiency and economy . Sodium methylate is preferably 0.05 to 0.5 parts by weight, preferably 0.1 to 0.3 parts by weight with respect to 100 parts by weight of the raw oil and fat, from the viewpoint of reaction efficiency and fractionation efficiency, and yield of liquid oil. Part by weight is more preferred.

  The enzyme catalyst is not particularly limited as long as it is a lipase having transesterification ability, and may be a random transesterase having no positional specificity or a transesterase having 1,3-position specificity. However, depending on the desired amount of palmitic acid at the 2-position, it is preferable to use a random transesterification reaction or a regiospecific transesterification reaction. The amount of the enzyme catalyst used is not particularly limited as long as the transesterification reaction proceeds, but is preferably 0.5 to 20 parts by weight with respect to 100 parts by weight of the raw oil and fat in view of reaction efficiency and economy.

  In the present invention, the direct transesterification reaction temperature is not particularly limited as long as it is a temperature at which the high melting point glyceride is crystallized, but the temperature at which the catalytic activity is highest is preferable in order to carry out the reaction efficiently at the start of the reaction. Specifically, when sodium methylate is used, it is preferably 50 ° C to 120 ° C, and when potassium sodium alloy is used, it is preferably 25 ° C to 270 ° C. Moreover, when using an enzyme catalyst, 50 to 70 degreeC is preferable. Moreover, when using a chemical catalyst, it is preferable to make direct transesterification temperature into 0 to 40 degreeC after 5 to 20 minutes from the start of reaction, and it is more preferable to make it into 10 to 40 degreeC. When using an enzyme catalyst, the direct transesterification reaction temperature is preferably 0 ° C. to 40 ° C., more preferably 10 ° C. to 40 ° C. 1 to 18 hours after the start of the reaction. In the present invention, the final reaction temperature is the direct transesterification reaction temperature.

  In the direct transesterification reaction, in the case of stirring, it is preferable to perform stirring at a speed of 1000 rpm or less, more preferably 600 rpm or less, more preferably from the viewpoint of imparting fluidity to fats and oils and producing excellent separable crystals. Preferably, it is 300 rpm to 1 rpm.

  From the viewpoint of fractionation efficiency, the final amount of crystals after the direct transesterification is preferably 3% to 60% by weight, more preferably 5% to 40% by weight, based on the total reaction fat. The amount of crystals may be controlled by the reaction time, and the direct transesterification reaction at 0 ° C. to 40 ° C., preferably 10 ° C. to 40 ° C. is performed for 1 to 48 hours when a chemical catalyst is used. In such a case, it is preferably performed for 3 to 120 hours.

  The method for stopping the direct transesterification reaction is not particularly limited as long as the reaction is stopped, but if it is a chemical catalyst, water or citric acid can be added, and it is acidic from the viewpoint of preventing deterioration of the equipment during fractionation. It is preferable to stop neutralization with the substance. The addition amount of the terminator is preferably 0.1 part by weight to 5 parts by weight and more preferably 0.2 part by weight to 1 part by weight with respect to 100 parts by weight of the reaction fat and oil from the viewpoint of fractionation efficiency. When the amount is more than 5 parts by weight, the filtration efficiency at the time of fractionation may deteriorate, and the yield of palm oil-derived liquid oil may decrease. On the other hand, when the addition amount of the terminator is less than 0.1 parts by weight, the color tone may deteriorate or the reaction may not stop.

  The direct transesterification reaction was stopped from the viewpoint of the yield of palm oil-derived liquid oil until the SSS content in the fat composition during the reaction was 31 wt% or less and the S2U content was 14 wt% or less. The latter is preferred. More preferably, from the viewpoint of the liquid property of the palm oil-derived liquid oil, it is preferable that the reaction is carried out until the SU2 / UUU (weight ratio) is 1.9 or less, further 1.1 or less.

  On the other hand, as the direct transesterification reaction is continued, the SSS content in the oil and fat during the reaction increases, so that the solid fat increases in the reaction system and it becomes difficult to separate. Therefore, from the viewpoint of fractionation efficiency, it is preferable to stop the reaction without the SSS content in the oil and fat being reacted exceeding 50% by weight, and it is more preferable to stop the reaction without the SSS content exceeding 31% by weight. Preferably, the reaction is more preferably stopped when the SSS content is between 1% by weight and 31% by weight, particularly preferably between 1% by weight and 25% by weight, very particularly preferably between 1% by weight and 15% by weight. % Is most preferred.

  In addition, the S2U content in the fat during the reaction decreases as the direct transesterification reaction continues, and from the viewpoint of the liquidity of the palm oil-derived liquid oil obtained by fractionation after the reaction, the S2U content in the fat during the reaction. It is preferable to stop the reaction until it is 14% by weight or less, more preferably 10% by weight or less, further preferably 7% by weight or less, and most preferably 5% by weight or less. .

  The method for fractionating palm oil-derived liquid oil after the direct transesterification is not limited to solvent fractionation and dry fractionation. However, since solvent fractionation requires equipment costs and running costs due to the use of solvent, dry fractionation without using a solvent is preferred. . When using a solvent, hexane, acetone or the like can be used. The fractionation temperature in the dry fractionation is preferably 0 ° C. to 45 ° C., preferably 30 ° C. or less, more preferably 20 ° C. or less, still more preferably 10 ° C. or less in order to obtain higher liquidity, and also the viewpoint of yield. Including 0 to 10 ° C is most preferable.

  In addition to the above-mentioned palm oil-derived liquid oil, the cooking oil according to the present invention can be used, for example, rapeseed oil, soybean oil, palm olein, super palm olein, cottonseed oil, corn oil, safflower oil, rice, depending on various uses and materials. At least one liquid oil selected from oil, sunflower oil, high oleic sunflower oil, high oleic rapeseed oil, fractionated oils thereof, and transesterified oil is blended in an amount of 60% by weight or less in the whole cooking oil. Thus, it is possible to obtain a flavor according to the purpose and preference. When the amount of the liquid oil exceeds 60% by weight and the amount of the palm oil-derived liquid oil is less than 40% by weight, the flavor deteriorates when fried and cannot be used for a long time, or at low temperatures. Sometimes crystals are generated.

  Moreover, you may make the cooking oil of this invention contain an emulsifier, an antioxidant, silicone, etc. as needed.

  The cooked oil of the present invention can be used for various fried foods such as deep-fried, fried, tempura, fried food, and fried food, as in the case of ordinary frying oil. Moreover, this cooking oil can be used for both non-frozen foods and frozen foods.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.

<Measurement of fatty acid composition>
The fatty acid composition in fats and oils was measured by the method described above.

<Measurement of each triglyceride content in fats and oils>
Each triglyceride content in fats and oils was measured by the method described above.

<Measurement of glyceride content with palmitic acid at the 2-position>
A mixture of 7.5 g of fat and oil to be analyzed and 22.5 g of ethanol, 1.2 g of Novozyme 435 (manufactured by Novozymes Japan) was added and reacted at 30 ° C. for 4 hours. The reaction solution was concentrated and then subjected to silica gel column chromatography ( Model No .: Silica gel 60 (0.063-0.200 mm) for column chromatography, manufactured by Merck) is separated into each component of triglyceride, diglyceride, monoglyceride, and the triglyceride component and diglyceride component remaining slightly unreacted are removed. The monoglyceride component was recovered. 0.05 g of the monoglyceride is dissolved in 5 ml of isooctane, 1 ml of 0.2 mol / L sodium methylate / methanol solution is added and reacted at 70 ° C. for 15 minutes to make methyl ester, and after neutralizing the reaction solution with acetic acid, an appropriate amount The glyceride content having palmitic acid at the second position was determined based on the retention time and peak area area of the organic phase by gas chromatography (model number: 6890N, manufactured by Agilent).

<Cloud point>
It was carried out in accordance with the standard fat and oil analysis test method “2.2.7-1996 Cloud point”.

<CDM (Conductometric Determination Method) test (oxidation stability)>
The CDM value was measured according to the standard fat and oil analysis test method “2.5.1.2-1996 CDM test”.

<Iodine number>
The measurement was carried out according to the standard fat and oil analysis test method “3.3.3-1996 iodine value (Wiis-cyclohexane method)”.

(Production Example 1: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was performed at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 18% by weight and 13.5% by weight, respectively, the reaction was terminated. The reaction was stopped by adding 50 parts by weight of water as an agent. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for draining and separating. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, 2 parts by weight of white clay is added, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, decreased from 40 ° C to 0.2 ° C / min (set value), and when 10 ° C is reached, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, by filtration using a filter press (pressurized to 3 MPa), 3200 parts by weight (yield: 64%) of liquid oil having a SU2 / UUU (weight ratio) of 1.1 in the triglyceride composition is obtained. It was.

(Production Example 2: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 27% by weight and 11.6% by weight, respectively, the reaction was stopped. The reaction was stopped by adding 50 parts by weight of water as an agent. Thereafter, in the same manner as in Production Example 1, 2700 parts by weight (yield: 54%) of a liquid oil having an SU2 / UUU (weight ratio) of 1.1 in the triglyceride composition was obtained.

(Production Example 3; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, followed by further reaction at 25 ° C. for about 24 hours. After confirming that the amount became 5% by weight, the reaction was stopped by adding 50 parts by weight of water as a reaction terminator. Thereafter, in the same manner as in Production Example 1, 3100 parts by weight (yield: 62%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.

(Production Example 4: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, and further at 25 ° C. for about 24 hours. The SSS content and the S2U content were 30% by weight in the total fat and oil in the reaction, respectively After confirming that the amount became 4% by weight, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2640 parts (yield: 53%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.

(Production Example 5; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, at 27.5 ° C. for about 2 hours, at 25 ° C. for about 12 hours, and at 22.5 ° C. for about 24 hours. After confirming that it became 23% by weight and 10.6% by weight in the whole oil and fat, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 3000 parts by weight (yield: 60%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.7 in the triglyceride composition was obtained.

(Production Example 6; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, at 27.5 ° C. for about 2 hours, at 25 ° C. for about 12 hours, and at 22.5 ° C. for about 24 hours. After confirming that it became 30 wt% and 8.0 wt% respectively in the whole oil and fat, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2600 parts by weight (yield: 52%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.7 in the triglyceride composition was obtained.

(Production Example 7; Production of liquid oil)
After adding 5000 parts by weight of palm olein (iodine value 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 30 ° C. for about 8 hours, 27.5 ° C. for about 2 hours, 25 ° C. for about 2 hours, 22.5 ° C. for about 5 hours, and 18 ° C. for about 15 hours. After confirming that the content and S2U content were 29% by weight and 3.8% by weight, respectively, in the total fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2700 parts by weight (yield: 54%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.5 in the triglyceride composition was obtained.

(Production Example 8; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 36 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 13% by weight and 16.5% by weight, respectively, the reaction terminator The reaction was stopped by adding 50 parts by weight of water. Thereafter, in the same manner as in Production Example 1, 3200 parts by weight (yield: 64%) of a liquid oil having a SU2 / UUU (weight ratio) of 1.3 in the triglyceride composition was obtained.

(Production Example 9; Production of liquid oil)
After 5000 parts by weight of palm oil (iodine value 52) was put into a separable flask and stirred at 100 rpm, vacuum dehydration was performed at 90 ° C., 5 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, followed by further reaction at 25 ° C. for about 24 hours. After confirming that it became 6% by weight, the reaction was stopped by adding 50 parts by weight of water as a reaction terminator. Thereafter, in the same manner as in Production Example 1, 1800 parts by weight (yield: 36%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.

(Production Example 10; Production of liquid oil)
After 5,000 parts by weight of palm olein (iodine number 57) was put into a separable flask and stirred at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 30 ° C. for about 8 hours, 27.5 ° C. for about 2 hours, 25 ° C. for about 2 hours, 22.5 ° C. for about 5 hours, and 18 ° C. for about 15 hours. After confirming that the content and S2U content were 37% by weight and 3.7% by weight, respectively, in the total fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 850 parts by weight (yield: 17%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.5 in the triglyceride composition was obtained.

  The liquid oils obtained by the production methods of Production Examples 1 to 10 were analyzed for fatty acid composition, triglyceride composition, cloud point, iodine value, and CDM value, and the results are summarized in Table 1.

(Production Example 11; production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.

(Production Example 12; Production of liquid oil)
While adding 5000 parts by weight of palm olein (iodine value: 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and after reaching 30 ° C., 25 parts by weight of tripalmitin powder (manufactured by Nacalai Tesque) was added, and direct transesterification was performed for 4 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 20% by weight and 11.5% by weight, respectively, 30 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.

(Production Example 13; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 300 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.

(Production Example 14; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was placed in a separable flask and stirred at 600 rpm, followed by vacuum dehydration at 90 ° C. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized up to 3 MPa) to obtain 3150 parts by weight of liquid oil (yield: 63%). )Obtained.

(Production Example 15; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and a direct transesterification reaction was performed at 38 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 16% by weight and 13.0% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, 3850 parts by weight (yield: 77%) of liquid oil was obtained by filtering using a filter press (pressurized to 3 MPa).

(Production Example 16; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and the direct transesterification reaction was carried out at 32 ° C. for 16 hours, then the temperature was further lowered, and the direct transesterification reaction was carried out at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, 3100 weight part (yield: 62%) of liquid oil was obtained by filter-separating using a filter press (pressurization to 3 Mpa).

(Production Example 17; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and the direct transesterification reaction was carried out at 32 ° C. for 16 hours, then the temperature was further lowered, and the direct transesterification reaction was carried out at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, it heated up to 30 degreeC and obtained 3350 weight part (yield: 67%) of liquid oils by filter-separating using a filter press (pressurization to 3 Mpa).

(Production Example 18; Production of liquid oil)
5000 parts by weight of palm olein (iodine number: 57) was placed in a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and a direct transesterification reaction was carried out at 32 ° C. for 12 hours, then the temperature was further lowered, and a direct transesterification reaction was carried out at 25 ° C. for 20 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 30% by weight and 8.0% by weight, respectively, 15 parts by weight of 25% aqueous citric acid was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.17 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 2700 parts by weight of liquid oil (yield: 54%). )Obtained.

(Production Example 19; Production of liquid oil)
While adding 5000 parts by weight of palm olein (iodine value: 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was carried out at 90 ° C., and then the temperature was lowered to 50 ° C. and lipase (“Lipozyme TL IM” manufactured by Novozymes) ) Was added and held at 50 ° C. for 4 hours, the temperature was lowered, direct transesterification was performed at 36 ° C. for 38 hours, the temperature was further lowered, and direct transesterification was performed at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the total fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, a filter press (pressurized up to 3 MPa) at 10 ° C. with the enzyme contained. ) To obtain 2850 parts by weight of liquid oil (yield: 57%).

(Production Example 20: Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, all the crystals were dissolved by heating, and after adding 70 ° C. warm water, the mixture was allowed to stand to separate the oil layer and the aqueous layer, and the hot water washing was performed to remove the water and separate it. The hot water washing is repeated until the pH of the separated aqueous layer becomes 8 or less, and then the oil and fat in the oil layer is heated to 90 ° C., vacuum dehydration is performed, 2 parts by weight of white clay is added, and the mixture is stirred for 20 minutes and then filtered. In this way, decolorization was performed except for the white clay. The oil and fat temperature after decolorization is 1 ° C / min (set value) until 40 ° C and from 40 ° C to 0.2 ° C / min (set value), and when it reaches 10 ° C, the temperature is maintained. Then, crystallization was performed until 24 hours in total from the start of temperature drop. After crystallization, 3200 parts by weight (yield: 64%) of liquid oil was obtained by filtering using a filter press (pressurized to 3 MPa).

  The analytical values of the liquid oils obtained in Production Examples 11 to 20 are summarized in Table 2.

(Examples 1 and 2, Comparative Examples 1 and 2)
<Fly test>
1000 g of each type of fats and oils shown in Table 3 was put into an electric fryer, and while maintaining the oil temperature at 180 ° C., 50 g of frozen potato was added once every hour and fried for 5 minutes to make fries. This was performed for 8 hours a day for 4 consecutive days, and the flavor of the fries fried on the 4th day was evaluated in comparison with the fries fried on the 1st day.
Evaluation was made by the following five-point method by eight panelists and rounded off to the second decimal place of the average score of the eight persons' evaluations to evaluate each oil and fat.
5 points: No deterioration odor similar to the flavor of French fries on the first day, and very good.
4 points: No deterioration odor, almost the same as the flavor of French fries on the first day, good.
3 points: Slightly deteriorated smell and slightly inferior to the flavor of French fries on the first day.
2 points: Deteriorated smell and inferior to the flavor of French fries on the first day.
1 point: Compared with the flavor of French fries on the first day, it has a considerably deteriorated odor and is extremely inferior.

<Refrigeration test>
100 g of each of the same fats and oils as described above was placed in a constant temperature bath at 4 ° C., and the state of the fats and oils after 1 week was observed.

  The results of the above fly test and refrigeration test are shown in Table 3.

  As shown in Table 3, the cooking oil according to the present invention using a palm oil-derived liquid oil can be used for a long period of time, with less deterioration of oil and fat during frying, less likely to deteriorate in flavor, and at low temperatures. Preservability was also good.

Claims (3)

  Palm oil containing palm oil and fat as a main raw material, and a glyceride having a SU2 / UUU weight ratio of 1.9 or less and an SSS content of 2% by weight or less and having palmitic acid bonded to the second position in the liquid oil. Cooking oil containing 40 to 100% by weight of the derived liquid oil in the whole cooking oil.   The cooking oil according to claim 1, wherein the cloud point of the palm oil-derived liquid oil is 0 to -12 ° C.   The cooking oil according to claim 1 or 2, wherein the palm oil-derived liquid oil has a CDM value of 5 hours or more.