WO2009098963A1 - 油脂の結晶化促進剤 - Google Patents
油脂の結晶化促進剤 Download PDFInfo
- Publication number
- WO2009098963A1 WO2009098963A1 PCT/JP2009/051202 JP2009051202W WO2009098963A1 WO 2009098963 A1 WO2009098963 A1 WO 2009098963A1 JP 2009051202 W JP2009051202 W JP 2009051202W WO 2009098963 A1 WO2009098963 A1 WO 2009098963A1
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- WIPO (PCT)
- Prior art keywords
- oil
- sorbitol
- fats
- crystallization
- fatty acid
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/013—Spread compositions
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Definitions
- the present invention relates to an oil and fat crystallization accelerator.
- oil and fat compositions such as margarine, shortening, chocolates and hard butter products used in confectionery and bread making have a large influence on the crystal behavior of the fats and oils used because the ratio of fats and oils in the composition is high. There were various problems.
- Patent Document 1 proposes an oil and fat crystal modifier containing diglyceride in order to prevent deterioration of physical properties due to the coarsening of fat and oil crystals.
- Patent Document 2 discloses a method for producing an oil and fat composition in which granular crystals having a diameter of 20 ⁇ m or more are not formed even under long-term storage, by rapid cooling with a refrigerant of ⁇ 20 ° C. or less, or unstable crystal particles of oil or fat.
- oils and fats that could not be fully crystallized in the manufacturing process crystallize during storage, or unstable crystals become stabilized crystals and become coarse, and there is no crystallization of fats and oils in the manufacturing process.
- the reason is considered to be sufficient.
- palm oil-based fats and oils are used as raw materials for plastic fats and oils such as margarine and shortening.
- palm oil has a slow crystallization speed, the problem of crystal coarsening during storage can be avoided.
- Patent Document 3 proposes a method for suppressing the formation of granular crystals of palm oil in which a sorbitan saturated fatty acid ester having an esterification rate of 20% or more and less than 50% is added.
- Patent Document 4 contains a saturated fatty acid-binding sorbitan fatty acid ester and a medium-chain fatty acid, and is a water-in-oil emulsified oil and fat composition that does not produce coarse crystals while highly containing palm oil.
- Patent Document 5 proposes a creaming property improver containing a saturated fatty acid-bonded sorbitan fatty acid ester as an active ingredient.
- the sheet-like plastic oil and fat composition used for folding into bread and confectionery dough has a sheet shape when the oil and fat crystallization is insufficient during the production process.
- the effect of accelerating crystallization of fats and oils during the manufacturing process is most required, such as the difficulty of molding the product into a solid, poor stiffness and spreadability of the product.
- transesterified oil and fat has increased.
- transesterified fats and oils that have a slower crystallization rate than hardened oil, especially random Plastic oil compositions such as margarine and shortening used are difficult to produce stably, and a solution has been demanded.
- the object of the present invention is crystallization that can promote crystallization of fats and oils in a short time during the production process of fats and oils compositions such as margarine, shortening, chocolates and hard butter products used in confectionery and bread making. It is an object to provide an accelerator.
- sorbitan fatty acid esters having an esterification rate of 28 to 60% and a sorbitol-type content of 20 to 40% are crystallization of fats and oils in a short time.
- the present inventors have found a phenomenon that exhibits a remarkable effect in promoting crystallization, and has completed the present invention.
- the first of the present invention is a fat crystallization accelerator containing a sorbitan fatty acid ester having an esterification rate of 28 to 60% and a sorbitol type content of 20 to 40%.
- the second is the oil crystallization accelerator according to the first aspect, wherein the content of palmitic acid and / or stearic acid is 90% by mass or more in 100% by mass of the constituent fatty acid of the sorbitan fatty acid ester.
- the third is an oil or fat composition containing the crystallization accelerator according to any one of the first to second.
- the oil-and-fat crystallization accelerator of the present invention can be used for confectionery, baking, margarine, shortening, chocolates, hard butter products, etc. It becomes possible to promote crystallization of fats and oils in a short time during the production process of the oil and fat composition.
- the oil and fat crystallization accelerator of the present invention has an esterification rate of 28 to 60%, preferably 28 to 50%, more preferably 30 to 45%, and a sorbitol type content of 20 to 40%, preferably 30. It contains sorbitan fatty acid ester which is ⁇ 40%.
- the form of sorbitol used as a raw material for the sorbitan fatty acid ester is, for example, white powder or granular D-sorbitol or D-sorbitol liquid containing about 50.0 to 70.0% by mass of D-sorbitol. Can be mentioned.
- the constituent fatty acid of the sorbitan fatty acid ester is more preferably palmitic acid and / or stearic acid, and the content of palmitic acid and / or stearic acid is 90% by mass or more in 100% by mass of the constituent fatty acid. More preferably it is.
- the production method of the sorbitan fatty acid ester used in the present invention is not particularly limited.
- the esterification reaction between sorbitol and the fatty acid may be performed without a catalyst, or may be performed using an acid catalyst or an alkali catalyst. It is preferably carried out in the presence of a catalyst.
- the acid catalyst include concentrated sulfuric acid and p-toluenesulfonic acid.
- the alkali catalyst include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and the like.
- the amount of the alkali catalyst used is about 0.01 to 1.0% by mass, preferably about 0.05 to 0.5% by mass, based on the total charged amount (in terms of dry matter).
- the said esterification reaction is, for example, a stirrer, a heating jacket, a baffle plate, an inert gas blowing tube, a thermometer and a water separator with a cooler Sorbitol, fatty acid, and catalyst are supplied to a normal reaction vessel equipped with a vessel and mixed with stirring, and the water produced by the esterification reaction in an inert gas atmosphere such as nitrogen or carbon dioxide is removed from the system. While being removed, heating is performed at a predetermined temperature for a predetermined time.
- the reaction temperature is usually in the range of about 180 to 260 ° C, preferably in the range of about 200 to 250 ° C.
- the reaction pressure is under reduced pressure or normal pressure, and the reaction time is about 0.5 to 15 hours, preferably about 1 to 3 hours.
- the end point of the reaction is usually determined by measuring the acid value of the reaction mixture and about 10 or less.
- the catalyst remaining in the reaction mixture may be neutralized.
- the temperature of the esterification reaction is 200 ° C. or higher, it is preferable to carry out the neutralization after cooling the liquid temperature to about 180 to 200 ° C.
- reaction temperature is 200 degrees C or less, you may neutralize at the same temperature. After neutralization, it is allowed to stand at that temperature for about 0.5 hour or more, more preferably for about 1 to 10 hours.
- unreacted sorbitol or sorbitol intramolecular condensate is separated into the lower layer, it is preferably removed.
- the sorbitan saturated fatty acid ester used in the present invention preferably has an esterification rate in the range of 28 to 60%.
- the esterification rate (%) is calculated by the following formula.
- the ester value and the hydroxyl value are determined in accordance with [ 2.3.3-1996 Ester Value] and [ 2.3.6-1996 Hydroxyl] of “Standard Oil and Fat Analysis Test Method (I)” (edited by the Japan Oil Chemists' Society). Value].
- the esterification rate of the sorbitan fatty acid ester is less than 28%, the melting point of the obtained sorbitan fatty acid ester is high, and the amount of hydrophilic ester produced increases, so that it is difficult to dissolve in fats and oils, and is not suitable for use. It is not preferable. Moreover, when the esterification rate of sorbitan fatty acid ester exceeds 60%, since the crystallization promotion effect of fats and oils reduces, it is not preferable.
- the sorbitan saturated fatty acid ester used in the present invention preferably has a sorbitol type content in the range of 20 to 40%.
- the sorbitol-type content means the content (%) of sorbitol in 100% of alcohol (for example, sorbitol, sorbitan, sorbide, etc.) constituting sorbitan fatty acid ester.
- alcohol for example, sorbitol, sorbitan, sorbide, etc.
- the fat and oil crystallization accelerator of the present invention is a fat and oil such as margarine, shortening, or chocolates and hard butter products that require an effect of promoting crystallization in a short time during the production process.
- the effects of the present invention can be exhibited.
- the sheet-like plastic fat composition even when a large amount of palm oil or transesterified fat with a low crystallization rate is used, the production process Since crystallization is promoted, a sheet-like plastic composition having good physical properties from the product outlet can be obtained.
- the solidification rate during the cooling process can be increased, and the cooling process can be shortened.
- the method for using the crystallization accelerator for fats and oils of the present invention is effective in promoting crystallization by melting in fats and oils and the crystallization accelerator from a state where the fats and crystallization accelerators are completely melted.
- the crystallization accelerator of the present invention is added in an amount of 0.05 to 1.0% by weight, more preferably 0.1 to 0.6% by weight, based on fats and oils. I can do it.
- SFC Solid Fat Content
- solid fat content indicates the content (%) of solid fat present in the fat under a certain temperature. Therefore, the larger the SFC value of the fat after a certain time from the start of the cooling step (crystallization step), the faster the fat crystallization and the higher the crystallization promoting effect.
- the evaluation test of the crystallization promoting effect can be performed as follows. First, a sample obtained by completely dissolving the crystallization accelerator in fats and oils at 80 ° C. is uniformly placed in a dedicated test tube and held in a constant temperature bath at 60 ° C. for 30 minutes. Subsequently, the SFC of the sample is measured in the nuclear magnetic resonance (NMR) apparatus after a predetermined time after the test tube containing the sample is transferred to a thermostat at 0 ° C.
- NMR nuclear magnetic resonance
- the evaluation test of the crystallization promotion effect can also be carried out by the following method. First, a sample obtained by completely dissolving the crystallization accelerator in fats and oils at 80 ° C. is uniformly put in a dedicated test tube. And hold in a constant temperature bath at 60 ° C. for 60 minutes. Subsequently, the SFC of the sample is measured in a nuclear magnetic resonance (NMR) apparatus after a predetermined time after the test tube containing the sample is transferred to a constant temperature bath at 15 ° C. or 20 ° C.
- NMR nuclear magnetic resonance
- oils and oils contained in the food containing the fats and oils include vegetable oils such as palm oil, cacao butter, coconut oil, and palm kernel oil, and animal fats such as milk fat, beef fat, lard, fish oil, whale oil, etc.
- Oils and fats include vegetable oils such as palm oil, cacao butter, coconut oil, and palm kernel oil, and animal fats such as milk fat, beef fat, lard, fish oil, whale oil, etc.
- Oils and fats rapeseed oil, soybean oil, sunflower seed oil, cottonseed oil, peanut oil, rice bran oil, corn oil, safflower oil, olive oil, kapok oil, sesame oil, evening primrose oil, palm oil, shea fat, monkey fat, cocoa butter, palm
- vegetable oils such as oil, palm kernel oil, and animal oils such as milk fat, beef tallow, lard, fish oil, whale oil, etc., alone or mixed oils, or processed oils subjected to curing, fractionation, transesterification, etc.
- the crystallization accelerator according to the present invention can be preferably applied to palm-based fats and oils, cacao butter, transesterified oils and the like that have a particularly low crystallization speed among these fats and oils, and is obtained by refining natural palm oil. Palm olein or palm stearin obtained by fractionating purified palm oil or natural palm oil can be mentioned, and transesterified oils and fats are particularly preferably applicable to random transesterified fats and oils.
- the esterification reaction was performed at 235 ° C. for about 1.5 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 520 g of sorbitan stearate ester (prototype 2; esterification rate: 32%, sorbitol-type content: 35%).
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 662 g of sorbitan stearate ester (Prototype 4; esterification rate 42%, sorbitol-type content 34%).
- palmitic acid (trade name: “palmitic acid 98”: palmitic acid content 98 mass%; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, and 13 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst.
- the esterification reaction was carried out under normal pressure at 235 ° C. in a nitrogen gas stream for about 2 hours until the acid value reached 10 or less.
- the obtained reaction product was cooled to obtain about 624 g of sorbitan palmitate (prototype 5; esterification rate 42%, sorbitol-type content 38%).
- stearic acid (trade name: “Stearic acid 65”; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, and 14 mL of a 10 w / v% sodium hydroxide aqueous solution was added as a catalyst.
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 685 g of sorbitan stearate ester (prototype 6; esterification rate: 45%, sorbitol-type content: 34%).
- palmitic acid (trade name: “palmitic acid 98”; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, and 14 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst, and a nitrogen gas stream under normal pressure
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 650 g of sorbitan palmitic acid ester (prototype 7; esterification rate 45%, sorbitol-type content 37%).
- stearic acid (trade name: “Stearic acid 65”; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, 15 mL of a 10 w / v% sodium hydroxide aqueous solution was added as a catalyst, and a nitrogen gas stream under normal pressure
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 710 g of sorbitan stearate ester (Prototype 8; esterification rate 47%, sorbitol-type content 34%).
- palmitic acid (trade name: “palmitic acid 98”; manufactured by Miyoshi Oil & Fats Co., Ltd.) is added, and 14 mL of a 10 w / v% aqueous solution of sodium hydroxide is added as a catalyst.
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 675 g of sorbitan palmitate ester (prototype 9; esterification rate 48%, sorbitol-type content 37%).
- stearic acid (trade name: “Stearic acid 65”; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, and 15 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst.
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 738 g of sorbitan stearate ester (prototype 10; esterification rate 49%, sorbitol type content 32%).
- the esterification reaction was carried out at about 235 ° C. for about 2 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 696 g of sorbitan palmitate (prototype 11; esterification rate 51%, sorbitol-type content 34%).
- the esterification reaction was performed at 235 ° C. for about 1.5 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 370 g of sorbitan palmitate (prototype 12; esterification rate: 26%, sorbitol-type content: 44%).
- stearic acid (trade name: “Stearic acid 65”; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, 11 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst, and a nitrogen gas stream under normal pressure
- the esterification reaction was performed at 235 ° C. for about 1.5 hours until the acid value became 10 or less.
- the obtained reaction product was cooled to obtain about 415 g of sorbitan stearate ester (prototype 13; esterification rate 27%, sorbitol-type content 39%).
- sorbitan fatty acid ester was saponified and decomposed into fatty acid and polyol. Specifically, 2.0 g of a test sample is weighed into a saponification flask, added with 30 mL of 0.5 mol / L potassium hydroxide-ethanol standard solution, attached to the flask with a condenser, and occasionally shaken. The temperature was adjusted within a range of about 70 to 80 ° C. so that the refluxing ethanol did not reach the top of the condenser, and the mixture was gently heated for about 1 hour, and then 50 mL of water was added.
- the obtained contents were transferred to a separatory funnel, 100 mL of hexane and about 5 mL of 35% hydrochloric acid were added, the separatory funnel was shaken, and then allowed to stand. Subsequently, the separated lower layer was transferred to another separatory funnel, and 50 mL of hexane was added for the same treatment.
- the separated lower layer was taken in a beaker, neutralized by adjusting the pH with a 0.5 mol / L potassium hydroxide solution, and dehydrated by allowing the beaker to stand in a ventilation dryer at 60 ° C. After complete dehydration, add about 10 mL of methanol and a small amount of mirabilite, stir, and naturally filter the contents. The obtained filtrate was transferred to a flask, and methanol was removed with an evaporator.
- the obtained concentrate was converted to TMS by a conventional method, and then a polyol composition analysis was performed using GC (gas chromatography). GC was performed under the following GC analysis conditions. After the analysis, the peak area corresponding to each component of the test sample recorded on the chromatogram by the data processor is measured using an integrator, and alcohol is used as the area percentage based on the measured peak area. The sorbitol type content in the composition was determined.
- ⁇ GC analysis conditions Apparatus Gas chromatogram (Model: GC-17A; manufactured by Shimadzu Corporation) Data processing device (model: C-R7A plus; manufactured by Shimadzu Corporation) Column (Model: DB-5HT; manufactured by Agilent Technologies) Column oven conditions Initial temperature 120 ° C (1 minute) Temperature rising rate 8 ° C / min Final temperature 340 ° C (25 minutes) Detector temperature 330 ° C Inlet temperature 330 ° C Sample injection volume 3 ⁇ L Detector FID (hydrogen flame ionization detector) Carrier gas Helium 75kPa Split ratio 1:80
- Examples 34 and 35 to which the prototype 6 was added had accelerated crystallization, and as a result, the state at the outlet had a firm and good physical property with sufficient hardness.
- Comparative Examples 22 to 24 since the crystallization was insufficient, the state at the outlet was soft, and it was difficult to obtain a product in a sheet shape.
- the result of the crystallization rate comparison test 1 is shown in a graph.
- the result of the crystallization speed comparison test 2 is shown in a graph.
- the result of the crystallization speed comparison test 3 is shown in a graph.
- the result of the crystallization speed comparison test 4 is shown in a graph.
- the result of the crystallization rate comparison test 5 is shown in a graph.
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Abstract
Description
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」:ステアリン酸含量65質量%、パルミチン酸含量35質量%;ミヨシ油脂社製)356g(約1.3モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液11mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約1.5時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品1;エステル化率29%、ソルビトール型含量36%)約470gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)411g(約1.5モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液11mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約1.5時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品2;エステル化率32%、ソルビトール型含量35%)約520gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)493g(約1.8モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液13mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品3;エステル化率39%、ソルビトール型含量35%)約607gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)548g(約2.0モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液14mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品4;エステル化率42%、ソルビトール型含量34%)約662gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にパルミチン酸(商品名:「パルミチン酸98」:パルミチン酸含量98質量%;ミヨシ油脂社製)512g(約2.0モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液13mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンパルミチン酸エステル(試作品5;エステル化率42%、ソルビトール型含量38%)約624gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)575g(約2.1モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液14mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品6;エステル化率45%、ソルビトール型含量34%)約685gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にパルミチン酸(商品名:「パルミチン酸98」;ミヨシ油脂社製)538g(約2.1モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液14mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンパルミチン酸エステル(試作品7;エステル化率45%、ソルビトール型含量37%)約650gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)603g(約2.2モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液15mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品8;エステル化率47%、ソルビトール型含量34%)約710gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にパルミチン酸(商品名:「パルミチン酸98」;ミヨシ油脂社製)563g(約2.2モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液14mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンパルミチン酸エステル(試作品9;エステル化率48%、ソルビトール型含量37%)約675gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)630g(約2.3モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液15mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品10;エステル化率49%、ソルビトール型含量32%)約738gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にパルミチン酸(商品名:「パルミチン酸98」;ミヨシ油脂社製)589g(約2.3モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液14mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2時間エステル化反応を行なった。得られた反応物を冷却してソルビタンパルミチン酸エステル(試作品11;エステル化率51%、ソルビトール型含量34%)約696gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にパルミチン酸(商品名:「パルミチン酸98」;ミヨシ油脂社製)256g(約1.0モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液11mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約1.5時間エステル化反応を行なった。得られた反応物を冷却してソルビタンパルミチン酸エステル(試作品12;エステル化率26%、ソルビトール型含量44%)約370gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた1Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)301g(約1.1モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液11mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約1.5時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品13;エステル化率27%、ソルビトール型含量39%)約415gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた2Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)767g(約2.8モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液5mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約2.5時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品14;エステル化率66%、ソルビトール型含量24%)約865gを得た。
撹拌機、温度計、ガス吹込管および水分離器を取り付けた2Lの四つ口フラスコに、ソルビトール(商品名:「ソルビトールS」;日研化成社製)260g(約1.0モル)を仕込み、約400Paの減圧下、75℃で約10分間脱水した。次にステアリン酸(商品名:「ステアリン酸65」;ミヨシ油脂社製)822g(約3.0モル)を仕込み、触媒として水酸化ナトリウム10w/v%水溶液5mLを加え、常圧下、窒素ガス気流中235℃で、酸価10以下となるまで約3時間エステル化反応を行なった。得られた反応物を冷却してソルビタンステアリン酸エステル(試作品15;エステル化率71%、ソルビトール型含量18%)約920gを得た。
製造例1~15で得たソルビタン脂肪酸エステル(試作品1~15)並びに後述の市販品AおよびBのソルビトール型含量は、下記する方法により測定した。
装置
ガスクロマトグラム(型式:GC-17A;島津製作所社製)
データ処理装置(型式:C-R7A plus;島津製作所社製)
カラム(型式:DB-5HT;Agilent Technologies社製)
カラムオーブン条件
初期温度 120℃(1分間)
昇温速度 8℃/分
最終温度 340℃(25分間)
検出器温度 330℃
注入口温度 330℃
試料注入量 3μL
検出機 FID(水素炎イオン化検出器)
キャリアガス ヘリウム75kPa
スプリット比 1:80
精製パーム油に、製造例1~15で作製したソルビタン脂肪酸エステル(試作品1~15)、および市販のソルビタン脂肪酸エステル(市販品AおよびB)を各々0.5質量%添加し、品温80℃にて、完全に溶解後、各サンプルを60℃の恒温槽で30分間保持した。その後、各サンプルを0℃の恒温槽に移し、20分後に各サンプルのSFCを測定した。
市販品A:ソルビタンステアリン酸エステル(商品名:ポエムS-300V;エステル化率31%、ソルビトール型含量57%;理研ビタミン社製)
市販品B:ソルビタンステアリン酸エステル(商品名:ポエムS-60V;エステル化率37%、ソルビトール型含量13%;理研ビタミン社製)
パーム油50部、パーム核油40部、パームステアリン10部を混合し、金属触媒(ナトリウムメトキシド)0.3部を加え、真空下80℃で1時間非選択的エステル交換反応を行った後、定法に従い精製したエステル交換油脂Aに、製造例1~15で作製したソルビタン脂肪酸エステル(試作品1~15)並びに市販品AおよびBを各々0.5質量%添加し、品温80℃にて、完全に溶解後、各サンプルを60℃の恒温槽で30分間保持した。その後、各サンプルを0℃の恒温槽に移し、3分後に各サンプルのSFCを測定した。
ヤシ油50部、パームステアリン40部、菜種極度硬化油10部を混合し、金属触媒(ナトリウムメトキシド)0.3部を加え、真空下80℃で1時間非選択的エステル交換反応を行った後、定法に従い精製したエステル交換油脂Bに、製造例1~15で作製したソルビタン脂肪酸エステル(試作品1~15)並びに市販品AおよびBを各々0.5質量%添加し、品温80℃にて、完全に溶解後、各サンプルを60℃の恒温槽で30分間保持した。その後、各サンプルを0℃の恒温槽に移し、3分後に各サンプルのSFCを測定した。
表4の配合にてシートマーガリンを試作し、試作直後のシートノズル出口での物性を評価した。
表4中のエステル交換油脂Cはパーム油30部、パームステアリン65部、菜種極度硬化油5部を混合し、金属触媒(ナトリウムメトキシド)0.3部を加え、真空下80℃で1時間非選択的エステル交換反応を行った後、定法に従い精製して得られた油脂を用いた。
なお、硬さの測定はレオメーターで行い、直径10mmのプランジャー、テーブルスピード5cm/分で測定した。
パーム中融点画分を融点36℃まで水素添加した硬化油(油脂D)に、製造例6で作製したソルビタン脂肪酸エステル(試作品6)並びに市販品B、C、D、EおよびFを各々0.5質量%添加し、品温85℃にて、完全に溶解後、軟化点(環玉法)測定用リング(内径15.9/19.8mm、高さ6.4mm)に1g流し込み、0℃恒温器内で2時間固化させた。
固化後、リングをろ紙(No.2、直径125mm)中央に置き、30℃恒温器内で24時間静置させた。
静置後、リング内の油脂から、ろ紙へ染み込んだ油脂の量を測定し、染み出し率を求めた。
市販品C:ソルビタンステアリン酸エステル(商品名:ポエムS-65V;エステル化率72%、ソルビトール型含量29%;理研ビタミン社製)
市販品D:ソルビタンベヘニン酸エステル(商品名:ポエムB-150;エステル化率67%、ソルビトール型含量24%;理研ビタミン社製)
市販品E:ポリグリセリン脂肪酸エステル(商品名:ポエムJ-46B;理研ビタミン社製)
市販品F:ショ糖脂肪酸エステル(商品名:シュガーエステルP-170;三菱化学フーズ社製)
油脂Dに、製造例6で作製したソルビタン脂肪酸エステル(試作品6)並びに市販品B、C、D、EおよびFを各々0.5質量%添加し、品温85℃にて、完全に溶解後、内径65mm、高さ40mmのプラスチック製カップに50g流し込み、0℃恒温器内で2時間固化させた。
固化後、カップ表面にろ紙(No.2、幅10mm、高さ200mm)を垂直に立て、30℃恒温器内で24時間静置させた。24時間静置後、カップの油脂から、ろ紙へ染み込んだ油脂の量(高さ)を測定した。
エステル交換油脂Bを90部とパームオレイン(ヨウ素価:67)を10部混合した油脂Eに、製造例6で作製したソルビタン脂肪酸エステル(試作品6)並びに市販品B、D、E、FおよびGを各々1.0質量%添加し、品温85℃にて、完全に溶解後、各サンプルを60℃の恒温槽で60分間保持した。その後、各サンプルを15℃又は20℃の恒温槽に移し、6分後に各サンプルのSFCを測定した。
市販品G:グリセリン脂肪酸エステル(商品名:ポエムB-100;理研ビタミン社製)
Claims (3)
- エステル化率が28~60%であり、かつソルビトール型含量が20~40%であるソルビタン脂肪酸エステルを含有する、油脂の結晶化促進剤。
- ソルビタン脂肪酸エステルの構成脂肪酸100質量%中パルミチン酸及び/又はステアリン酸の含量が90質量%以上である請求項1記載の油脂の結晶化促進剤。
- 請求項1~2いずれか記載の結晶化促進剤を含有する油脂組成物。
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- 2009-01-26 US US12/866,569 patent/US8440250B2/en active Active
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US8648065B2 (en) | 2002-10-02 | 2014-02-11 | Meiji Seika Pharma Co., Ltd. | Antibacterial medicinal composition of enhanced oral absorptivity |
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JP2016002069A (ja) * | 2014-06-19 | 2016-01-12 | ミヨシ油脂株式会社 | 離型油 |
JP2016144434A (ja) * | 2015-02-09 | 2016-08-12 | 理研ビタミン株式会社 | マイグレーション抑制剤 |
CN115053931A (zh) * | 2022-05-31 | 2022-09-16 | 江南大学 | 一种油脂结晶促进剂及其制备方法和应用 |
CN115053931B (zh) * | 2022-05-31 | 2023-08-25 | 江南大学 | 一种油脂结晶促进剂及其制备方法和应用 |
Also Published As
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CN101990571A (zh) | 2011-03-23 |
US8440250B2 (en) | 2013-05-14 |
TW200940703A (en) | 2009-10-01 |
US20110250343A1 (en) | 2011-10-13 |
JP5293221B2 (ja) | 2013-09-18 |
JP2009209350A (ja) | 2009-09-17 |
CN101990571B (zh) | 2013-07-24 |
TWI454569B (zh) | 2014-10-01 |
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