JPH0475592A - Fats and oils having emulsifying characteristic and production thereof - Google Patents

Fats and oils having emulsifying characteristic and production thereof

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Publication number
JPH0475592A
JPH0475592A JP2188214A JP18821490A JPH0475592A JP H0475592 A JPH0475592 A JP H0475592A JP 2188214 A JP2188214 A JP 2188214A JP 18821490 A JP18821490 A JP 18821490A JP H0475592 A JPH0475592 A JP H0475592A
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Japan
Prior art keywords
oil
oils
fats
reaction
oleic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP2188214A
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Japanese (ja)
Other versions
JP2844869B2 (en
Inventor
Yasunobu Hasegawa
泰伸 長谷川
Takako Nakajima
中島 多佳子
Hisao Miyagawa
宮川 久雄
Chihiro Katou
加藤 千潯
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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  • Edible Oils And Fats (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

PURPOSE:To enable production of edible fats and oils having excellent emulsifying characteristics without adding an emulsifying agent thereto by carrying out hydrolytic reaction and ester interchange reaction of specific edible vegetable fats and oils using a 1,3-regiospecific lipase. CONSTITUTION:A 1,3-regiospecific lipase, derived from the genus Rhizopus, etc., and used for reaction, together with an enzyme activator such as lecithin, is dissolved in water and immobilized on a carrier such as Celite(R) or an ion exchange resin to prepare an immobilized enzyme agent, which is then filled in a column. Mixed fats and oils (substrate) of edible liquid fats and oils such as olive oil, having the moisture content therein regulated within the range of 100 to 800ppm, preferably 200 to 400ppm and containing >=40% oleic acid at the 2-position of triglyceride and palm oil under the same conditions as described above are continuously passed through the column to carry out hydrolytic reaction and ester interchange reaction. Thereby, since the resultant fats and oils are excellent in emulsifying characteristics and temperature shock resistance without requiring tempering, margarines, etc., can efficiently be produced.

Description

【発明の詳細な説明】 [産業上の利用分野] 本発明はすぐれた乳化特性を持つ食用油脂を、乳化剤を
添加することなく製造する方法に関するものである。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing edible fats and oils having excellent emulsifying properties without adding an emulsifier.

[従来の技術および問題点〕 従来、乳化特性を持つ食用油脂の製造法としては、レシ
チンや各種脂肪酸グリセリンエステル、シュガーエステ
ルなど、食品添加物として認可されている乳化剤を添加
する方法が知られている。
[Prior art and problems] Conventionally, methods for producing edible oils and fats with emulsifying properties include adding emulsifiers approved as food additives, such as lecithin, various fatty acid glycerin esters, and sugar esters. There is.

特にマーガリン等の水との乳化状態の油脂製品を製造す
るためには、乳化剤を添加することが必要不可欠であっ
た。しかし今日では消費者の意識として一般的に天然志
向や自然志向が強まり、乳化剤等の添加物の添加されて
いない商品を要求するする意向が非常に高まってきてい
る。
In particular, in order to produce oil and fat products in an emulsified state with water, such as margarine, it is essential to add an emulsifier. However, today, consumers are generally becoming more natural-oriented and natural-oriented, and their intention to request products that do not contain additives such as emulsifiers has increased significantly.

また、マーガリン等の製造時に急冷固化する段階で、こ
の温度ショックにより、乳化剤の選択を誤ると乳化が破
壊される場合もある。
Moreover, if the emulsifier is selected incorrectly, the emulsification may be destroyed due to this temperature shock during the rapid cooling and solidification stage during the production of margarine and the like.

[発明が解決しようとする課題] 本発明は乳化剤を添加することなく、すぐれた乳化特性
を持つ食用油脂を製造するためになされたものである。
[Problems to be Solved by the Invention] The present invention was made in order to produce edible fats and oils having excellent emulsifying properties without adding an emulsifier.

[課題を解決するための手段] 本発明はすぐれた乳化特性を持つ食用油脂を、乳化剤を
添加することなく製造する方法に関するものである。
[Means for Solving the Problems] The present invention relates to a method for producing edible fats and oils having excellent emulsifying properties without adding an emulsifier.

また従来、オレイン酸モノグリセリドを乳化剤として用
いた場合、他の乳化剤、例えばステアリンモノグリセリ
ドなどを用いた場合よりも温度ショックに対する乳化の
耐性や高温に対する乳化の耐性が強いとされている。本
発明の製造方法で得られた油脂はオレイン酸モノグリセ
リドを多く含むため、温度ショック耐性にすぐれている
Furthermore, it has been conventionally believed that when oleic acid monoglyceride is used as an emulsifier, the emulsification resistance to temperature shock and high temperature is stronger than when other emulsifiers such as stearin monoglyceride are used. Since the fats and oils obtained by the production method of the present invention contain a large amount of oleic acid monoglyceride, they have excellent resistance to temperature shock.

さらに本発明により製造された食用油脂は、マーガリン
およびショートニング製造後にテンバリングの必要がな
い、すなわちテンパリング前後において、油脂の結晶型
や硬さに変化がなく、生産効率が極めて良くなる。
Furthermore, the edible fats and oils produced according to the present invention do not require tempering after producing margarine and shortening, that is, there is no change in the crystal type or hardness of the fats and oils before and after tempering, resulting in extremely high production efficiency.

上記課題を達成するために、トリグリセリドの2位置に
40%以上オレイン酸を含んでいる食用植物油脂の混合
物を、1,3−位置特異性リパーゼを用いる加水分解反
応およびエステル交換反応をすることによりすぐれた乳
化特性の油脂を得る方法である。すなわち、油脂中の水
分を1100ppから800ppmの範囲、好ましくは
200ppmから400ppmの範囲で1,3−位置特
異性リパーゼを用いて、選択的加水分解反応およびエス
テル交換反応を行なうことによって、優れた乳化特性を
有する油脂を得ることができる。
In order to achieve the above object, a mixture of edible vegetable oils containing 40% or more of oleic acid at the 2-position of triglyceride was subjected to a hydrolysis reaction and transesterification reaction using a 1,3-position-specific lipase. This is a method for obtaining fats and oils with excellent emulsifying properties. That is, excellent emulsification can be achieved by performing selective hydrolysis and transesterification using a 1,3-regiospecific lipase at a moisture content in fats and oils in the range of 1100 ppm to 800 ppm, preferably in the range of 200 ppm to 400 ppm. It is possible to obtain fats and oils with specific properties.

原料としては、オリーブ油、サフラワー油、ひまわり油
、なたね油、ごま油などトリグリセリドの2位置に40
%以上オレイン酸を含んでいる食用液体油脂のうちから
選ばれた少なくとも1種類と、トリグリセリドの2位置
に40%以上オレイン酸を含んでいるパーム油の混合油
脂を用いることができる。
Raw materials include olive oil, safflower oil, sunflower oil, rapeseed oil, sesame oil, etc.
A mixture of at least one kind selected from edible liquid fats and oils containing oleic acid at 40% or more and palm oil containing 40% or more oleic acid at the 2-position of the triglyceride can be used.

本発明で用いるリパーゼとして、リゾーブス属(Rhi
zopus)、アスペルギルス属(Aspergill
us)、ムコール属(Mucor)、フミコーラ属(H
umicola)、ペニシリウム属(Penicill
ium)由来のリパーゼなどを用いることができる。具
体的には、天野製薬(株)が販売している次のリパーゼ
を用いることができる。すなわち、Rh1zopus 
 de 1 eme r由来の「リパーゼDJ (商品
名、以下同じ)、Rh1zopus  javanic
uS由来の[リパーゼF−AP15] 、Rh1z。
As the lipase used in the present invention, Rhizobus sp.
zopus), Aspergillus spp.
us), Mucor, Humicola (H
umicola), Penicillium spp.
Lipase derived from M.ium) can be used. Specifically, the following lipase sold by Amano Pharmaceutical Co., Ltd. can be used. That is, Rh1zopus
"Lipase DJ (product name, same hereinafter) derived from de 1 emer, Rh1zopus javanic
[Lipase F-AP15] derived from uS, Rh1z.

pus  niger由来の「リパーゼAPJ、Muc
or  javanicus由来の「リパーゼM−AP
」、Humicola  lanuginosa由来の
「リパーゼCEJ 、Penicillium  ro
queforti由来のrリパーゼR−20jなどであ
る。
"Lipase APJ, Muc" derived from P. pus niger
"Lipase M-AP" derived from or javanicus
”, “Lipase CEJ from Humicola lanuginosa, Penicillium ro
queforti-derived r-lipase R-20j.

本発明の選択的加水分解およびエステル交換反応は次の
方法にて行なう。
The selective hydrolysis and transesterification reactions of the present invention are carried out in the following manner.

反応に使用するリパーゼをレシチンなどの酵素活性化剤
と共に水にとかしてセライトやイオン交換樹脂などの担
体に固定化し、固定化酵素を調製する。この固定化酵素
剤をカラムに充填し、油脂中の水分を1100ppから
800ppmの範囲、好ましくは200ppmから40
0ppmの範囲に調製し、混合油脂(基質)を30〜6
0″Cで連続的にカラムに流して、反応を行なう。
An immobilized enzyme is prepared by dissolving the lipase used in the reaction in water together with an enzyme activator such as lecithin and immobilizing it on a carrier such as Celite or ion exchange resin. This immobilized enzyme agent is packed in a column, and the water content in the oil and fat is in the range of 1100 ppm to 800 ppm, preferably 200 ppm to 40 ppm.
Adjust the mixed fat (substrate) to 30 to 6 ppm.
The reaction is carried out by continuously flowing through the column at 0''C.

実施例l Rh1zopus  delemer由来のリパーゼ(
天野製薬(株) 商品名「リパーゼDJ)265gと精
製粉末大豆レシチン80gを水6゜Omlに溶かし、9
Kgの陽イオン交換樹脂「WK−13,(三菱化成(株
)製)に加え、約30分間よく撹拌し、樹脂の表面にリ
パーゼを均一にコーティングし乾燥することなく用いた
。反応基質として、なたね油(2位置のオレイン酸比率
が59.2%の物)25%、パーム油(2位置のオレイ
ン酸比率が63.5%の物)75%の比率で混合したも
のを減圧乾燥し、水分を300ppmに調整した。固定
化リパーゼ3Kgをカラムに充填して、カラム全体を6
0°Cに保った。上記の混合原料油脂を60°Cに加温
し、ポンプで毎分60m1を定量的にカラムに流し、6
0°Cで連続的に酵素反応を行なった。カラム出口での
油脂の持つ水分量が350 ppmに達してからサンプ
リングを開始し、反応油40Kgを得た。この時点で反
応油には分解生成物として脂肪酸が6%程度含まれてい
たが、以下の精製行程により除去することができた。す
なわち、反応生成物に2%の活性白土を加えて80℃、
30分間、20mmHgの減圧下に撹拌し、脱色を行な
った。50°C保温下に自然濾過を行ない、脱色前を得
た。得られた脱色前を250°C150分間、2mmH
g、吹き込み水蒸気量2.5%で真空水蒸気蒸留(脱臭
)を行なって37Kgの精製油を得た。この精製油には
約0.4%のモノグリセリドと約12.5%のジグリセ
リドが含まれていた。
Example l Lipase from Rh1zopus delemer (
Dissolve 265 g of Amano Pharmaceutical Co., Ltd. (trade name: Lipase DJ) and 80 g of purified powdered soybean lecithin in 6° Oml of water.
Kg of cation exchange resin WK-13 (manufactured by Mitsubishi Kasei Corporation) was added to the resin, stirred well for about 30 minutes, and the surface of the resin was uniformly coated with lipase, which was used without drying.As a reaction substrate, A mixture of 25% rapeseed oil (with a 2-position oleic acid ratio of 59.2%) and 75% palm oil (a 2-position oleic acid ratio of 63.5%) was dried under reduced pressure to remove moisture. was adjusted to 300 ppm.The column was filled with 3 kg of immobilized lipase, and the entire column was
It was kept at 0°C. The above mixed raw material fat and oil was heated to 60°C and quantitatively poured into the column at 60 ml per minute using a pump.
Enzyme reactions were performed continuously at 0°C. Sampling was started after the water content of the oil at the column outlet reached 350 ppm, and 40 kg of reaction oil was obtained. At this point, the reaction oil contained about 6% fatty acid as a decomposition product, which could be removed by the following purification process. That is, 2% activated clay was added to the reaction product and heated at 80°C.
The mixture was stirred for 30 minutes under a reduced pressure of 20 mmHg to decolorize it. Gravity filtration was performed while maintaining the temperature at 50°C to obtain the product before decolorization. The obtained before decolorization was heated at 250°C for 150 minutes at 2mmH.
Vacuum steam distillation (deodorization) was performed at a blown steam amount of 2.5% to obtain 37 kg of refined oil. This refined oil contained about 0.4% monoglycerides and about 12.5% diglycerides.

この反応油30Kgを60℃に加温して完全に融解し油
相(80%)とした。次にあらかじめ水6.38Kg 
(17%)、食塩0.38Kg (1゜5%)、粉乳0
.38Kg (1,5%)を配合した合計20%の水相
を添加し、通常用いられる予備乳化機、マーガリン製造
機にて乳化、急冷、固化、練圧を行ない、乳化剤を添加
することなく30Kgの良好な性状のマーガリンを製造
した。
30 kg of this reaction oil was heated to 60° C. and completely melted to form an oil phase (80%). Next, 6.38 kg of water is added in advance.
(17%), salt 0.38Kg (1°5%), milk powder 0
.. A total of 20% water phase containing 38Kg (1.5%) was added, and emulsification, quenching, solidification, and kneading were performed using a commonly used pre-emulsifier and margarine manufacturing machine to produce 30Kg without adding an emulsifier. A margarine with good properties was produced.

比較例1 実施例1の原料油脂と同じ組成の油脂を用い、乳化剤を
用いることなくマーガリンを製造した。
Comparative Example 1 Margarine was produced using an oil having the same composition as the raw material oil of Example 1 without using an emulsifier.

すなわち、なたね油(2位置のオレイン酸比率が59.
2%の物)25%、パーム油(2位置のオレイン酸比率
が63.5%の!l@)75%の比率で混合した油脂3
0Kgを60°Cに加温して完全に融解し油相(80%
)とした。次にあらかじめ水6.38Kg (17%)
、食塩0.38Kg (1゜5%)、粉乳0.38Kg
 (1,5%)を配合した合計20%の水相を添加し、
通常用いられる予備乳化機、マーガリン製造機にて乳化
、急冷、固化、練圧を行ない、乳化剤を添加することな
く30Kgのマーガリンを製造した。しかし、乳化剤を
加えていないため、通常の方法では予備乳化の段階での
乳化が充分性なわれず油脂と水分が分離し、性状の良い
マーガリンを得ることはできなかった。
That is, rapeseed oil (the oleic acid ratio at the 2-position is 59.
Oil and fat 3 mixed at a ratio of 25% (2%) and 75% palm oil (with a 2-position oleic acid ratio of 63.5%!)
0Kg is heated to 60°C to completely melt it and form an oil phase (80%
). Next, 6.38Kg (17%) of water in advance
, salt 0.38Kg (1°5%), milk powder 0.38Kg
Add a total of 20% aqueous phase containing (1,5%),
Emulsification, quenching, solidification, and kneading were performed using a commonly used pre-emulsifier and margarine manufacturing machine to produce 30 kg of margarine without adding an emulsifier. However, since no emulsifier is added, conventional methods do not emulsify sufficiently during the pre-emulsification stage, resulting in separation of oil and water, making it impossible to obtain margarine with good properties.

実施例2 Rhizopus  delemer由来のリパーゼ(
大野製薬(株)商品名「リパーゼD」)263gと精製
粉末大豆レシチン78.8gを水3500mlに溶かし
、4.91Kgのセライトに加え、約30分間よく撹拌
し、セライトの表面にリパーゼを均一にコーティングし
た・リパーゼが均一にコーティングされたセライトを4
0°C115mmHgで3時間乾燥処理し、固定化リパ
ーゼを調製した。この酵素剤は水分含量が1%であった
。反応基質として、サフラワー油(2位置のすレイン酸
比率が84.0%の物)30%、パーム油(2位置のオ
レイン酸比率が63.5%)70%の比率で混合したも
のを減圧乾燥し、水分を3ooppmに調整した。この
混合原料油脂を、実施例1と同様に酵素反応、精製を行
ない40Kgの反応精製油を得た。この精製油には約0
.4%のモノグリセリドと約12.3%のジグリセリド
が含まれていた。
Example 2 Lipase derived from Rhizopus delemer (
Dissolve 263 g of Ohno Pharmaceutical Co., Ltd. (trade name "Lipase D") and 78.8 g of purified powdered soybean lecithin in 3500 ml of water, add to 4.91 kg of Celite, and stir well for about 30 minutes to uniformly coat the lipase on the surface of the Celite. Coated/Celite uniformly coated with lipase 4
The immobilized lipase was prepared by drying at 0°C and 115mmHg for 3 hours. This enzyme preparation had a water content of 1%. As a reaction substrate, a mixture of 30% safflower oil (with a 2-position oleic acid ratio of 84.0%) and 70% palm oil (with a 2-position oleic acid ratio of 63.5%) was used. It was dried under reduced pressure and the moisture content was adjusted to 3ooppm. This mixed raw material oil and fat was subjected to enzymatic reaction and purification in the same manner as in Example 1 to obtain 40 kg of reacted and purified oil. This refined oil has approximately 0
.. It contained 4% monoglycerides and about 12.3% diglycerides.

この反応油を実施例1と同様にしてマーガリンを製造し
た。つまり、反応油30Kgを60°Cに加温して完全
に融解し油相(80%)とした。次にあらかじめ水6.
38Kg(17%)、食塩0゜38Kg(1,5%)、
粉乳0.38Kg (1゜5%)を配合した合計20%
の水相を添加し、通常用いられる予備乳化機、マーガリ
ン製造機にて乳化、急冷、同化、練圧を行ない、乳化剤
を添加することな(30Kgのマーガリンを製造した。
Margarine was produced using this reaction oil in the same manner as in Example 1. That is, 30 kg of reaction oil was heated to 60° C. and completely melted to form an oil phase (80%). Next, water 6.
38Kg (17%), salt 0°38Kg (1.5%),
Total 20% including milk powder 0.38Kg (1°5%)
The aqueous phase was added, and emulsification, quenching, assimilation, and kneading were performed using a commonly used pre-emulsifier and margarine manufacturing machine, without adding an emulsifier (30 kg of margarine was manufactured).

比較例2 実施例2の原料油脂と同じ組成の油脂を用い、乳化剤を
用いることなくマーガリンを製造した。
Comparative Example 2 Margarine was produced using an oil having the same composition as the raw material oil of Example 2 without using an emulsifier.

すなわち、サフラワー油(2位置のオレイン酸比率が8
4,0%の物)30%、パーム油(2位置のオレイン酸
比率が63.5%)70%の比率で混合した油脂30K
gを60°Cに加温して完全に融解し油相(80%)と
した。次にあらかじめ水6.38Kg (17%)、食
塩0.38Kg (1゜5%)、粉乳0.38Kg (
1,5%)を配合し7%合計20%の水相を添加し、通
常用いられる予備乳化機、マーガリン製造機にて乳化、
急冷、固化、練圧を行ない、乳化剤を添加することなく
30Kgのマーガリンを製造した。しかし、この場合も
比較例1と同じく、乳化剤を加えていないため、通常の
方法では予備乳化の段階での乳化が充分行なわれず油脂
と水分が分離し、性状の良いマーガリンを得ることはで
きなかった。これらの結果を表1にまとめた。マーガリ
ンの高温耐制は、25°Cに一定時間曝すことにより、
マーガリン表面に分離して現れる油分を観察したもので
ある。
That is, safflower oil (the oleic acid ratio at the 2-position is 8)
Oil and fat 30K mixed at a ratio of 30% (4.0%) and 70% palm oil (2-position oleic acid ratio is 63.5%)
g was heated to 60°C to completely melt and form an oil phase (80%). Next, in advance, 6.38Kg (17%) of water, 0.38Kg (1°5%) of salt, 0.38Kg of milk powder (
1.5%), add 7% and a total of 20% aqueous phase, and emulsify using a commonly used pre-emulsifier or margarine manufacturing machine.
By performing rapid cooling, solidification, and kneading, 30 kg of margarine was produced without adding an emulsifier. However, in this case as well, as in Comparative Example 1, no emulsifier was added, so in the usual method emulsification was not performed sufficiently at the pre-emulsification stage and oil and fat separated from water, making it impossible to obtain margarine with good properties. Ta. These results are summarized in Table 1. The high temperature resistance of margarine is achieved by exposing it to 25°C for a certain period of time.
This is an observation of oil that separates and appears on the surface of margarine.

[発明の効果] 本発明は、今まで乳化剤を添加しなければ製造すること
が極めて困難であったマーガリン等の原料油脂として、
乳化剤を添加しなくてもすぐれた乳化特性を持つ油脂の
製造を可能にしたものである。また本発明の方法により
得られた油脂は、マーガリン製造時の急冷固化の温度シ
ョックに対する耐性や高温に対する耐性にも優れており
、またテンバリングの必要もないかめ、極めて効率的に
マーガリン等を製造することができる。
[Effects of the Invention] The present invention provides raw material fats and oils for margarine and the like, which until now have been extremely difficult to produce without adding an emulsifier.
This makes it possible to produce fats and oils with excellent emulsifying properties without adding an emulsifier. In addition, the fats and oils obtained by the method of the present invention have excellent resistance to temperature shock during rapid solidification during margarine production and resistance to high temperatures, and can be used to produce margarine etc. extremely efficiently without the need for tempering. be able to.

Claims (4)

【特許請求の範囲】[Claims] (1)トリグリセリドの2−位置に40%以上オレイン
酸を含んでいる食用植物油脂の混合物を、トリグリセリ
ドの1,3−位置特異性を有するリパーゼを用いて反応
系の水分を100ppmから800ppmの範囲、好ま
しくは200ppmから400ppmの範囲に保った状
態で加水分解反応およびエステル交換反応を行なって得
られる乳化特性を有する油脂
(1) A mixture of edible vegetable oils containing 40% or more of oleic acid at the 2-position of triglycerides is mixed with a lipase having specificity for the 1,3-position of triglycerides, and the water content of the reaction system is reduced to a range of 100 ppm to 800 ppm. Fats and oils having emulsifying properties obtained by carrying out a hydrolysis reaction and a transesterification reaction while maintaining the concentration preferably in the range of 200 ppm to 400 ppm.
(2)オリーブ油、サフラワー油、ひまわり油、なたね
油、ごま油トリグリセリドを含む2−位置に40%以上
オレイン酸を含んでいる食用液体油脂のうちから選ばれ
た少なくとも1種類とトリグリセリドの2−位置に40
%以上オレイン酸を含んでいるパーム油との混合油脂か
ら得られる請求項1記載油脂
(2) At least one type of edible liquid fat and oil containing 40% or more of oleic acid at the 2-position, including olive oil, safflower oil, sunflower oil, rapeseed oil, and sesame oil triglyceride, and at least one type of edible liquid fat containing oleic acid at the 2-position of the triglyceride. 40
The fat or oil according to claim 1, which is obtained from a mixed fat or oil with palm oil containing oleic acid of % or more.
(3)請求項1記載の油脂のシヨートニング及び/また
はマーガリン、スプレッド類の原料油脂としての利用
(3) Use of the oil and fat according to claim 1 as a raw material for toning and/or margarine and spreads.
(4)請求項1記載の油脂の製造方法。(4) The method for producing fats and oils according to claim 1.
JP2188214A 1990-07-17 1990-07-17 Fats and oils with emulsifying properties and their production Expired - Lifetime JP2844869B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2188214A JP2844869B2 (en) 1990-07-17 1990-07-17 Fats and oils with emulsifying properties and their production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2188214A JP2844869B2 (en) 1990-07-17 1990-07-17 Fats and oils with emulsifying properties and their production

Publications (2)

Publication Number Publication Date
JPH0475592A true JPH0475592A (en) 1992-03-10
JP2844869B2 JP2844869B2 (en) 1999-01-13

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Country Status (1)

Country Link
JP (1) JP2844869B2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU752215B2 (en) * 1998-07-21 2002-09-12 Dupont Nutrition Biosciences Aps Foodstuff
JP2013215176A (en) * 2012-04-12 2013-10-24 Kao Corp Water-in-oil emulsified composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU752215B2 (en) * 1998-07-21 2002-09-12 Dupont Nutrition Biosciences Aps Foodstuff
JP2013215176A (en) * 2012-04-12 2013-10-24 Kao Corp Water-in-oil emulsified composition

Also Published As

Publication number Publication date
JP2844869B2 (en) 1999-01-13

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