JP5308309B2 - Method for producing highly liquid palm oil for cooking - Google Patents
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Images
Description
本発明は、高液状性パーム系油脂の製造方法に関する。 The present invention relates to a method for producing a highly liquid palm oil.
家庭用サラダ油としてはキャノーラなどの菜種油が主流である。しかしながら、昨今、ヨーロッパなどでのバイオディーゼルの急速な普及により、菜種油の価格が高騰し、サラダ油の製造コストが高くなっている。また、菜種油は今後供給面でも逼迫することが予測される。そこで、安価でしかも供給が安定なパーム系油脂を原料にサラダ油を製造することができれば極めて有意義である。 Rapeseed oil such as canola is the mainstream as household salad oil. However, recently, due to the rapid spread of biodiesel in Europe and the like, the price of rapeseed oil has soared and the production cost of salad oil has increased. In addition, rapeseed oil is expected to tighten in the future. Therefore, it is extremely meaningful if salad oil can be produced using palm oil and fat which is inexpensive and stable in supply.
パーム系油脂から高液状性油脂を得る方法としては、アルカリ触媒を用いる化学的エステル交換法がある。非特許文献１に開示のダイレクテッドエステル交換においては、パーム油をアルカリ触媒を用いて３０℃前後でエステル交換を行う。トリ飽和脂肪酸グリセリドを結晶化させ、反応系から除去しながら、反応を進行させることにより、高液状性油脂が得られることが記載されている。しかしながら、この方法では触媒除去が煩雑で収率が悪い。収率を向上させるためには溶剤分別が必要となり、作業がより煩雑となる。 As a method of obtaining highly liquid oil from palm oil, there is a chemical transesterification method using an alkali catalyst. In directed transesterification disclosed in Non-Patent Document 1, palm oil is transesterified at around 30 ° C. using an alkali catalyst. It is described that a highly liquid oil can be obtained by crystallizing trisaturated fatty acid glycerides and allowing the reaction to proceed while removing them from the reaction system. However, in this method, catalyst removal is complicated and the yield is poor. In order to improve the yield, solvent fractionation is required, and the work becomes more complicated.
非特許文献２には、多段ドライ分別法が開示されている。この方法では、パーム油からドライ分別を３回行い、ヨウ素価７０の高液状性パーム系油脂を得ている。得られた高液状性パーム系油脂は単独でサラダ油冷却試験をクリアするが、収率が低く、また製造時間も長い。 Non-Patent Document 2 discloses a multistage dry fractionation method. In this method, dry fractionation is performed three times from palm oil to obtain a highly liquid palm-based oil and fat having an iodine value of 70. The obtained highly liquid palm oil and fat alone clears the salad oil cooling test, but the yield is low and the production time is long.
以上のように、化学的エステル交換法では、触媒除去が煩雑で収率が悪い。収率を向上させるためには溶剤分別が必要となり、作業がより煩雑となる。また、アルカリ触媒を用いる影響で精製を行っても油の風味が悪く、色も濃くなる。また、多段分別法では、収率が低く、製造時間も長い。さらに、液状性も十分ではない。 As described above, in the chemical transesterification method, the catalyst removal is complicated and the yield is poor. In order to improve the yield, solvent fractionation is required, and the work becomes more complicated. Moreover, even if it refine | purifies by the influence which uses an alkali catalyst, the flavor of oil is bad and a color also becomes dark. In the multistage fractionation method, the yield is low and the production time is long. Furthermore, the liquidity is not sufficient.
上記課題を解決するために、パーム系油脂の酵素的エステル交換により高液状性パーム系油脂を得る方法がある（特許文献１および２）。しかしながら、従来の方法では依然として液状性が十分ではなく、特に高い液状性が要求されるサラダ油等への使用に適したものは得られていなかった。また、従来では、通常、パーム系油脂と液状性の高い他の油脂とを混合したものが原料として用いられており、パーム系油脂単独を原料として、高い収率で高液状性油脂を得ることは依然として困難であった。
そこで、酵素的エステル交換および分別を２回以上繰り返すことによりパーム系油脂から高液状性油脂を得る方法が提案されている（特許文献３）。
In order to solve the above-mentioned problems, there is a method for obtaining a highly liquid palm-based fat / oil by enzymatic transesterification of palm-based fat / oil (Patent Documents 1 and 2). However, the conventional method still does not have sufficient liquidity, and a product suitable for use in salad oil or the like that requires particularly high liquidity has not been obtained. In addition, conventionally, a mixture of palm-based fats and oils and other highly liquid fats is used as a raw material, and high-liquid fats and oils are obtained in a high yield from palm-based fats and oils alone. Was still difficult.
Then, the method of obtaining highly liquid fats and oils from palm-type fats and oils by repeating enzymatic transesterification and fractionation twice or more is proposed (patent document 3).
しかしながら、近年、油脂の色や、風味等の品質のさらなる向上が求められており、特許文献３に開示された方法では、このような要求に応えることが難しい。 However, in recent years, there has been a demand for further improvements in the quality of oils and fats, the quality of flavors, etc., and it is difficult for the method disclosed in Patent Document 3 to meet such requirements.
本発明によれば、（Ａ）ヨウ素価６３以上、８５以下のパーム系油脂を、リパーゼを用いてランダムエステル交換する工程と、（Ｂ）前記工程（Ａ）で得られた該エステル交換油脂から、分別により、ＳＳＳ（Ｓは飽和脂肪酸で、ＳＳＳは飽和脂肪酸３つで構成されるトリグリセリドを意味する）を除去し、高液状性パーム系油脂を得る工程とを含み、前記高液状性パーム系油脂において、ＰＯＰ／（ＰＯＰ+ＰＰＯ）比が０．６以下であり、Ｐ ２ Ｏ含量が１２質量％以下である加熱調理用の高液状性パーム系油脂の製造方法が提供される。
ＰＯＰは、１位および３位がパルミチン酸、２位がオレイン酸で構成されるトリグリセリドを示し、ＰＰＯは１および２位がパルミチン酸、３位がオレイン酸で構成されるトリグリセリド、と２および３位がパルミチン酸、１位がオレイン酸で構成されるトリグリセリドとを意味する。
Ｐ ２ Ｏはパルミチン酸２つとオレイン酸１つで構成されるトリグリセリドを意味する。
According to the present invention, (A) iodine value greater than 63, 85 following palm based fat, a step of randomly transesterified with lipase, (B) the interesterified fat obtained in the step (A) And by removing SSS (S is a saturated fatty acid, SSS means a triglyceride composed of three saturated fatty acids) by fractionation, and obtaining a highly liquid palm oil and fat, the highly liquid palm in the system oil, POP / (POP + PPO) ratio Ri der 0.6, the method of producing a high liquid resistance palm based fat for cooking P 2 O content is not more than 12 wt% is provided.
POP is a triglyceride composed of palmitic acid at positions 1 and 3 and oleic acid at position 2, PPO is a triglyceride composed of palmitic acid at positions 1 and 2 and oleic acid at positions 3 and 2 and 3 It means a triglyceride whose position is palmitic acid and whose position is composed of oleic acid.
P 2 O means a triglyceride composed of two palmitic acids and one oleic acid.
この発明によれば、品質が良好な高液状性パーム系油脂を得ることができる。 According to this invention, a high-liquid palm oil-based fat with good quality can be obtained.
また、本発明では、高液状性パーム系油脂の製造方法において、前記工程（Ａ）におけるエステル交換は複数回実施せず、前記工程（Ｂ）において、前記エステル交換油脂から、分別によりＳＳＳを除去する操作を１回以上実施することが好ましい。さらに、前記工程（Ａ）におけるエステル交換および前記工程（Ｂ）における分別除去操作（エステル交換油脂から分別により、ＳＳＳを除去する操作）をそれぞれ複数回実施しないことがより好ましい。
このように、エステル交換および分別除去操作を複数回繰り返さないことにより、より品質が良好な高液状性パーム系油脂を得ることができる。
さらに、エステル交換および分別除去操作をそれぞれ複数回繰り返さないことにより、作業性が改善されるとともに、高液状性パーム系油脂の収率も高めることができる。
Moreover, in this invention, in the manufacturing method of highly liquid palm-type fats and oils, transesterification in the said process (A) is not implemented in multiple times, and in the said process (B), SSS is removed from the said transesterified fats and oils by fractionation. It is preferable to perform the operation to perform once or more. Furthermore, it is more preferable that the transesterification in the step (A) and the separation / removal operation in the step (B) (operation for removing SSS by separation from the transesterified oil / fat) are not performed a plurality of times.
Thus, by not repeating the transesterification and separation and removal operations a plurality of times, it is possible to obtain high-liquid palm-based fats and oils with better quality.
Furthermore, by not repeating the transesterification and separation and removal operations a plurality of times, the workability is improved and the yield of the high-liquid palm-based oil and fat can be increased.
さらに、本発明では、前記パーム系油脂として、パーム油を１回以上分別して得られたヨウ素価６３以上のパームオレインを使用することが好ましい。
このようにすることで、品質が良好な高液状性パーム系油脂を確実に得ることができる。
また、本発明では、工程（Ａ）のエステル交換において、ランダムエステル交換能を有するリパーゼを用いることが好ましく、さらには、工程（Ｂ）において、分別をドライ分別にて行うことが好ましい。
Furthermore, in this invention, it is preferable to use the palm olein of the iodine number 63 or more obtained by fractionating palm oil 1 time or more as said palm oil fat.
By doing in this way, the high-liquid palm-type oil and fat with favorable quality can be obtained reliably.
Moreover, in this invention, it is preferable to use the lipase which has random transesterification ability in transesterification of a process (A) , and also in a process (B), it is preferable to perform a fractionation by dry fractionation.
本発明によれば、品質が良好な高液状性パーム系油脂を得ることができる高液状性パーム系油脂の製造方法が提供される。 ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of the highly liquefied palm oil fat which can obtain the highly liquefied palm oil fat with favorable quality is provided.
以下、本発明の実施の形態について説明する。
本発明の説明において、Ｓは飽和脂肪酸、Ｐはパルミチン酸、Ｏはオレイン酸、およびＬはリノール酸を意味する。また、ＳＳＳは飽和脂肪酸３つで構成されるトリグリセリド、ＰＰＰはパルミチン酸３つで構成されるトリパルミチン、ＯＯＯはオレイン酸３つで構成されるトリオレインを意味する。さらに、ＰＯＰは１および３位がパルミチン酸、２位がオレイン酸で構成されるトリグリセリドであり、ＰＰＯは１および２位がパルミチン酸、３位がオレイン酸で構成されるトリグリセリド、と２および３位がパルミチン酸、１位がオレイン酸で構成されるトリグリセリドとの両方を包含する。ＰＬＰは１および３位がパルミチン酸、２位がリノール酸で構成されるトリグリセリドであり、ＰＬＯは１位がパルミチン酸、２位がリノール酸、３位がオレイン酸で構成されるトリグリセリド、と３位がパルミチン酸、２位がリノール酸、１位がオレイン酸で構成されるトリグリセリドとの両方を包含する。
Embodiments of the present invention will be described below.
In the description of the present invention, S means saturated fatty acid, P means palmitic acid, O means oleic acid, and L means linoleic acid. SSS means triglyceride composed of three saturated fatty acids, PPP means tripalmitin composed of three palmitic acids, and OOO means triolein composed of three oleic acids. Further, POP is a triglyceride composed of palmitic acid at positions 1 and 3 and oleic acid at position 2, PPO is a triglyceride composed of palmitic acid at positions 1 and 2, and 3 and 3 with oleic acid. It includes both palmitic acid at the position and triglyceride composed of oleic acid at the position 1. PLP is a triglyceride composed of palmitic acid at positions 1 and 3 and linoleic acid at position 2, PLO is a triglyceride composed of palmitic acid at position 1, linoleic acid at position 2, oleic acid at position 3, and 3 It includes both triglycerides composed of palmitic acid at position 2, linoleic acid at position 2, and oleic acid at position 1.
本発明の高液状性パーム系油脂の製造方法は、（Ａ）ヨウ素価６３以上、８５以下のパーム系油脂を、リパーゼを用いてエステル交換する工程と、（Ｂ）エステル交換する前記工程（Ａ）で得られた該エステル交換油脂を分別して、ＳＳＳを除去し、高液状性パーム系油脂を得る工程と、を含む。
このような製造方法では、リパーゼを用いたエステル交換を行った後、固形部と、液状部とを分別し、高融点トリグリセリドを除去する。このような製造方法では、工程（Ｂ）を実施した後、工程（Ａ）を再度実施するようなことがなく、品質、特に色、風味が良好な高液状性パーム系油脂を得ることができる。
具体的には、本発明の製造方法によれば、
（ｉ）ＰＰＰ含量が０．２質量％以下、
（ｉｉ）Ｐ２Ｏ（Ｐ２Ｏはパルミチン酸２つとオレイン酸１つで構成されるトリグリセリドを意味する）含量が１２質量％以下、
（ｉｉｉ）ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比が０．３以上、０．６以下、
（ｉｖ）ヨウ素価が７０以上、
であり、かつ、品質、特に色、風味が良好な高液状性パーム系油脂を得ることができる。
The method for producing a highly liquid palm oil / fat of the present invention comprises (A) a step of transesterifying a palm oil / oil having an iodine value of 63 or more and 85 or less using lipase, and (B) the step of transesterification (A And the step of separating the transesterified oil and fat obtained in step 1) to remove SSS to obtain a highly liquid palm-based oil and fat.
In such a manufacturing method, after performing transesterification using lipase, a solid part and a liquid part are fractionated and a high melting point triglyceride is removed. In such a production method, after the step (B) is performed, the step (A) is not performed again, and a highly liquid palm-based oil and fat having good quality, particularly color and flavor can be obtained. .
Specifically, according to the production method of the present invention,
(I) PPP content is 0.2 mass% or less,
(Ii) P 2 O (P 2 O means triglyceride composed of two palmitic acids and one oleic acid) content of 12 % by mass or less,
(Iii) POP / (POP + PPO) ratio is 0.3 or more and 0.6 or less,
(Iv) iodine value is 70 or more,
In addition, it is possible to obtain a highly liquid palm-based oil and fat having good quality, particularly color and flavor.
次に各工程について詳細に説明する。 Next, each step will be described in detail.
（工程（Ａ））
工程（Ａ）では、ヨウ素価６３以上のパーム系油脂を、リパーゼを用いて酵素的エステル交換する。
原料であるヨウ素価６３以上のパーム系油脂は、一回以上の分別によって得られたパームオレインであることが好ましい。
さらに、原料のパーム系油脂は、ヨウ素価６５以上のパームオレインであることが好ましく、より好ましくは、ヨウ素価６７以上のパームオレインである。このように、ヨウ素価６３以上のパーム系油脂を使用することで、揚げ物の脂っぽさを低減させて軽い感じに仕上がるという効果を得ることができる。
なお、原料のパーム系油脂のヨウ素価の上限値は、製造効率の観点から、８５以下、特には７０以下であることが好ましい。
ヨウ素価８５を超えるパーム系油脂を用いて本発明の製造方法により、液状性をさらに高めることは可能であるが、本発明の製造方法に用いるヨウ素価８５を超えるパーム系油脂を分別で得ようとすると、原料であるパーム油からの収率がかなり低くなり、全工程の製造効率が非常に悪くなる。
原料として、ヨウ素価６３以上のパーム系油脂単独で用いても、他の油脂と混合して用いてもよい。特に、原料中にパーム系油脂が大部分を占める場合、例えば、パーム系油脂を単独または実質的に単独で用いた場合や他の油脂の混合率が１０質量％以下のような場合に、特に本発明の効果が顕著となる。
酵素的エステル交換に使用するリパーゼは、特に限定されない。しかし、１，３位特異性を有するものでは十分な効果を発揮できない可能性があるため、ランダムエステル交換能を有するものが好ましい。
(Process (A))
In the step (A), palm-based fats and oils having an iodine value of 63 or more are enzymatically transesterified using lipase.
The palm oil and fat having an iodine value of 63 or more, which is a raw material, is preferably palm olein obtained by one or more fractionations.
Furthermore, it is preferable that the raw material palm-based fat is palm olein having an iodine value of 65 or more, and more preferably palm olein having an iodine value of 67 or more. In this way, by using palm-based fats and oils having an iodine value of 63 or more, it is possible to obtain the effect of reducing the fatiness of the deep-fried food and finishing it lightly.
In addition, it is preferable that the upper limit of the iodine value of the raw material palm oil fat is 85 or less, particularly 70 or less, from the viewpoint of production efficiency.
Although it is possible to further improve liquidity by the production method of the present invention using palm-based fats and oils having an iodine value of more than 85, palm oils and fats having an iodine value of more than 85 used in the production method of the present invention will be obtained by fractionation. Then, the yield from the palm oil which is a raw material will become quite low, and the manufacturing efficiency of all the processes will become very bad.
As a raw material, you may use perm | palm-type fats and oils with an iodine value of 63 or more, or may mix and use with other fats and oils. In particular, when palm-based fats and oils occupy most of the raw material, for example, when palm-based fats and oils are used alone or substantially alone, or when the mixing ratio of other fats and oils is 10% by mass or less, The effect of the present invention becomes remarkable.
The lipase used for enzymatic transesterification is not particularly limited. However, since those having 1,3-position specificity may not exhibit sufficient effects, those having random transesterification ability are preferred.
図１は、パーム系油脂のランダムエステル交換を概念的に示した図である。パーム系油脂のランダムエステル交換を行うことにより、油脂中にＰＰＰなどの高融点のトリ飽和脂肪酸グリセリド（ＳＳＳ）が増加する。パーム系油脂には、ＰＯＰが多く含まれており、その他の成分として、ＰＰＯ、ＯＯＰ、ＰＬＰ、ＰＯＬ、ＯＯＯ等が混在している。
パーム系油脂における、ＰＯＰおよびＰＰＯの合計を基準としたＰＯＰ比は通常、約０．９〜約０．８である。ランダムエステル交換を行うことにより、ＰＰＰ、ＰＰＯ、およびＯＯＯなどが形成され、ＰＯＰの比率は減少する（図１を参照）。その後、分別にてＰＰＰなどのトリ飽和脂肪酸グリセリド（ＳＳＳ）を除去し、油脂中の飽和脂肪酸を減じることによって液状性を向上させることができる。
FIG. 1 is a diagram conceptually showing random transesterification of palm-based fats and oils. By carrying out random transesterification of palm oil and fat, high melting point trisaturated fatty acid glycerides (SSS) such as PPP increase in the oil and fat. Palm oils and fats contain a large amount of POP, and PPO, OOP, PLP, POL, OOO, etc. are mixed as other components.
The POP ratio based on the sum of POP and PPO in palm-based fats and oils is usually about 0.9 to about 0.8. By performing random transesterification, PPP, PPO, OOO, and the like are formed, and the ratio of POP decreases (see FIG. 1). Thereafter, trisaturated fatty acid glycerides (SSS) such as PPP are removed by separation, and the liquidity can be improved by reducing the saturated fatty acids in the fats and oils.
酵素的エステル交換反応条件は、平衡（特にランダム化）に達する条件であれば、特に限定されない。また、反応形態はカラム充填式、バッチ式、またはその他の形態を用いてもよい。 The enzymatic transesterification reaction conditions are not particularly limited as long as the conditions reach equilibrium (particularly randomization). The reaction form may be a column packing type, a batch type, or other forms.
（工程（Ｂ））
工程（Ｂ）では、工程（Ａ）で得られた該エステル交換油脂を分別して、ＳＳＳを除去する。
分別は、ドライ分別または溶剤分別を用いることができる。しかしながら、溶剤分別は設備投資が高額であり、しかも操作が煩雑であるため、ドライ分別を用いることが好ましい。本発明ではドライ分別を用いても、高い品質を有する液状部を収率良く得ることができる。
溶剤分別とは、エステル交換油脂を溶剤に溶解して、分別する方法であり、ドライ分別とは、溶剤を使用せずに、エステル交換油脂の晶析を行い分別する方法である。
(Process (B))
In step (B), the transesterified oil / fat obtained in step (A) is fractionated to remove SSS.
For the fractionation, dry fractionation or solvent fractionation can be used. However, it is preferable to use dry fractionation because solvent fractionation is expensive and the operation is complicated. In the present invention, even when dry fractionation is used, a liquid part having high quality can be obtained with high yield.
Solvent fractionation is a method in which transesterified fats and oils are dissolved in a solvent and fractionated, and dry fractionation is a method of fractionating by crystallization of transesterified fats and oils without using a solvent.
分別の条件は特に限定されないが、エステル交換油脂を分別して、ＳＳＳを除去する条件で行う。この工程（Ｂ）では、液状性を高めるためにＳＳＳをほぼ完全に除去し、中融点部であるＰ２Ｏ等もある程度除去することが好ましい。このような分別条件としては、例えば、分別の最終温度を０〜１０℃程度で、３０分〜３時間程度行うのが好ましい。 Although the conditions for fractionation are not particularly limited, the separation is performed under conditions for separating the transesterified oil and fat and removing SSS. In this step (B), it is preferable to remove SSS almost completely and to remove P 2 O, which is an intermediate melting point, to some extent in order to improve liquidity. As such a separation condition, for example, it is preferable to carry out the final temperature of the separation at about 0 to 10 ° C. for about 30 minutes to 3 hours.
本発明では、工程（Ａ）におけるエステル交換は複数回実施せず、工程（Ｂ）において、前記エステル交換油脂から分別により、ＳＳＳを除去する操作（分別除去操作）を１回以上実施することが好ましい。
このようにすることで、より品質、特に味、風味が良好な高液状性パーム系油脂を得ることができる。
ただし、作業性や、高液状性パーム系油脂の収率等の観点から、工程（Ｂ）における分別除去操作は、２回以下であることが好ましい。工程（Ｂ）における分別除去操作を２回とした場合には、高液状性パーム系油脂の収率を低下させずに、ヨウ素価の高い高液状性パーム系油脂を得ることができる。
さらに、工程（Ａ）におけるエステル交換および工程（Ｂ）における分別除去操作をそれぞれ複数回実施しないことがより好ましい。
このようにすることで、さらに品質、特に味、風味が良好な高液状性パーム系油脂を得ることができる。また、工程（Ａ）におけるエステル交換および工程（Ｂ）における分別除去操作をそれぞれ２回以上実施しないことで、作業性が改善され、さらに、ヨウ素価が比較的高い高液状性パーム系油脂を得ることができるとともに、高液状性パーム系油脂の収率もさらに高めることができる。
すなわち、高い収率、良好な作業性、比較的高いヨウ素価の３点を両立させるという観点からは、工程（Ａ）におけるエステル交換および工程（Ｂ）における分別除去操作をそれぞれ２回以上実施しないことが好ましい。
In the present invention, the transesterification in the step (A) is not performed a plurality of times, and in the step (B), the operation of removing SSS by separation from the transesterified fat (separation removal operation) may be performed one or more times. preferable.
By doing in this way, the highly liquid palm-type oil-fat whose quality, especially taste and flavor are favorable can be obtained.
However, from the viewpoints of workability and the yield of highly liquid palm-based fats and oils, it is preferable that the separation and removal operation in the step (B) is performed twice or less. When the separation and removal operation in the step (B) is performed twice, a high liquid palm-based fat and oil having a high iodine value can be obtained without reducing the yield of the high-liquid palm-based fat and oil.
Furthermore, it is more preferable that the transesterification in the step (A) and the separation / removal operation in the step (B) are not performed a plurality of times.
By doing in this way, the high-liquid-palm-type fats and oils with further favorable quality, especially a taste and flavor can be obtained. Moreover, workability | operativity is improved by not performing transesterification in a process (A) and the fraction removal operation in a process (B) twice or more, respectively, Furthermore, the high liquid palm oil fat which has a comparatively high iodine number is obtained. In addition, the yield of highly liquid palm-based fats and oils can be further increased.
That is, from the viewpoint of achieving both high yield, good workability, and relatively high iodine value, transesterification in the step (A) and fractional removal operation in the step (B) are not performed twice or more. It is preferable.
なお、特許文献３においては、酵素的エステル交換、分別の一連の工程を２回以上繰り返さないと、高い収率で高液状性パーム系油脂を得ることは難しいとされている。これに対し、本発明では、ヨウ素価６３以上のパーム系油脂を使用することで、酵素的エステル交換、分別の工程を実施したのち再度酵素的エステル交換、分別の工程を実施しなくても、高い収率で高液状性パーム系油脂を得ることができる。さらに、本発明者は、味、風味が良好な高液状性パーム系油脂を得られ、なおかつ、得られた高液状性パーム系油脂を揚げ物に使用した場合、揚げ物の油っぽさが低減されて軽い感じに仕上がるという効果があることを見出した。 In Patent Document 3, it is considered difficult to obtain a highly liquid palm-based oil and fat with a high yield unless the series of steps of enzymatic transesterification and fractionation is repeated twice or more. On the other hand, in the present invention, by using palm-based fats and oils having an iodine value of 63 or more, the enzymatic transesterification, after performing the separation step, the enzymatic transesterification, without performing the separation step, A highly liquid palm-based oil and fat can be obtained with a high yield. Furthermore, the present inventor can obtain a high liquid palm oil and fat with good taste and flavor, and when the obtained high liquid palm oil and fat is used for fried food, the oiliness of the fried food is reduced. I found out that it has the effect of being light and light.
ここで、酵素的ランダムエステル交換を行うことにより、ＰＯＰ／ＰＰＯ比が変化する。パーム系油脂におけるＰＯＰの比率は、ＰＯＰおよびＰＰＯの合計を基準とした場合約０．９〜約０．８である。一方、ランダムエステル交換すると、ＰＯＰおよびＰＰＯの合計を基準としたＰＯＰ比は約０．３３となる。最終的に得られる高液状性パーム系油脂における、ＰＯＰおよびＰＰＯの合計を基準としたＰＯＰ比は、好ましくは０．３以上、０．６以下であり、より好ましくは０．４以上、０．５５以下である。 Here, the POP / PPO ratio is changed by enzymatic random transesterification. The ratio of POP in palm-based fats and oils is about 0.9 to about 0.8 when the total of POP and PPO is used as a reference. On the other hand, when random transesterification is performed, the POP ratio based on the sum of POP and PPO is about 0.33. The POP ratio based on the sum of POP and PPO in the high-liquid palm-based fat finally obtained is preferably 0.3 or more and 0.6 or less, more preferably 0.4 or more and 0.00. 55 or less.
図２に、ＰＯＰ／ＰＰＯ比と融点との関係を示す。図２の縦軸が融点を示し、横軸がＰＯＰ／ＰＰＯ比を示す。ＰＯＰ／ＰＰＯの相図によると、ＰＯＰ／ＰＰＯが５０／５０で分子化合物を形成し、Ｐ２Ｏとしては融点が最も低くなる。よって、最終的に得られた油脂組成物のＰＯＰの比がＰＯＰおよびＰＰＯの合計を基準として、約０．５である場合に、Ｐ２Ｏ含量が同じ組成物であれば、最も液状性が高いものが得られる。相図からＰ２Ｏとして析出してくる温度は、ランダムエステル交換した方が低くなることがわかる。従って、ランダムエステル交換を行った方がＰＰＰとＰ２Ｏの融点の差が広がるため、分別時の温度を高くすることができ、ＰＰＰを除去しやすくなり、収率が向上する。 FIG. 2 shows the relationship between the POP / PPO ratio and the melting point. The vertical axis in FIG. 2 indicates the melting point, and the horizontal axis indicates the POP / PPO ratio. According to the phase diagram of POP / PPO, a molecular compound is formed when POP / PPO is 50/50, and P 2 O has the lowest melting point. Therefore, when the ratio of POP of the finally obtained oil and fat composition is about 0.5 on the basis of the sum of POP and PPO, the composition having the same P 2 O content is most liquid. A high one is obtained. It can be seen from the phase diagram that the temperature of precipitation as P 2 O is lower when random transesterification is performed. Therefore, since the difference between the melting points of PPP and P 2 O increases when random transesterification is performed, the temperature at the time of fractionation can be increased, PPP can be easily removed, and the yield is improved.
本発明の方法により製造されるパーム系油脂は、高い液状性を有する。具体的には、本発明の高液状性パーム系油脂は、ＰＰＰ含量が０．２質量％以下、Ｐ２Ｏ含量が１２質量％以下である。該範囲内で、高液状性パーム系油脂は菜種油の配合が５０質量％以下でサラダ油規格の冷却試験をクリアすることが可能である。
また、さらに好ましくは、ＰＰＰ含量が０．０５質量％未満、Ｐ２Ｏ含量が１２質量％以下であり、このような範囲内であると単独でサラダ油規格の冷却試験をクリアする。
The palm oil / fat produced by the method of the present invention has high liquidity. Specifically, the highly liquid palm-based fat / oil of the present invention has a PPP content of 0.2% by mass or less and a P 2 O content of 12 % by mass or less. Within this range, the liquefied rapeseed oil can satisfy the cooling test of the salad oil standard when the rapeseed oil content is 50% by mass or less.
More preferably, the PPP content is less than 0.05% by mass, and the P 2 O content is 12% by mass or less.
さらに、本発明により製造される高液状性パーム系油脂は、ＰＯＰの比が、ＰＯＰおよびＰＰＯの合計を基準として、０．３以上、０．６以下であり、通常のパーム系油脂と比較してＰＰＯに対するＰＯＰ比が小さいことを特徴とする。さらに好ましくは、ＰＯＰの比がＰＯＰおよびＰＰＯの合計を基準として、０．４以上、０．５５以下である。これに対し、エステル交換を行っていないパーム系油脂原料のＰＯＰの比は、ＰＯＰおよびＰＰＯの合計を基準として、通常、約０．９〜約０．８である。上述の通り、Ｐ２Ｏ含量が同じ組成物なら、ＰＯＰ／ＰＰＯの比が約５０／５０である場合、すなわちＰＯＰの比が、ＰＯＰおよびＰＰＯの合計を基準として、約０．５である場合に、最も液状性が高い。本発明の高液状性パーム系油脂は、ＰＰＯに対するＰＯＰ比が減少されているため、エステル交換されていないＰ２Ｏ含量が同じ組成物と比較して液状性が高くなっている。 Furthermore, the high-liquid palm-based fats and oils produced according to the present invention have a POP ratio of 0.3 or more and 0.6 or less, based on the total of POP and PPO, compared with ordinary palm-based fats and oils. The POP ratio with respect to PPO is small. More preferably, the ratio of POP is 0.4 or more and 0.55 or less on the basis of the sum of POP and PPO. On the other hand, the ratio of POP of the palm-based fat raw material that has not been transesterified is usually about 0.9 to about 0.8 on the basis of the total of POP and PPO. As described above, if the composition has the same P 2 O content, the POP / PPO ratio is about 50/50, that is, the POP ratio is about 0.5 based on the sum of POP and PPO. In addition, it has the highest liquidity. Since the POP ratio with respect to PPO is reduced, the highly liquid palm-based fats and oils of the present invention have higher liquidity than a composition having the same P 2 O content that has not been transesterified.
本発明により製造される高液状性パーム系油脂は、ヨウ素価が７０以上であり液状性が高い。ヨウ素価は不飽和結合の量を示す指標である。ヨウ素価が高いほど不飽和脂肪酸の量が多いため、液状性が高くなり、好ましい。 The highly liquid palm-based oil and fat produced according to the present invention has an iodine value of 70 or more and high liquidity. The iodine value is an index indicating the amount of unsaturated bonds. The higher the iodine value, the higher the amount of unsaturated fatty acid, and the higher the liquidity, which is preferable.
さらに、高液状性パーム系油脂は、エステル交換の際にアルカリ触媒を用いずに製造されているため、風味がよく、色度も低い。また、菜種油やアルカリ触媒を用いたエステル交換油脂と比較して、耐熱性に優れ、着色上昇率も低い。 Furthermore, since the highly liquid palm-based fats and oils are produced without using an alkali catalyst during the transesterification, they have a good flavor and low chromaticity. Moreover, compared with transesterified oils and fats using rapeseed oil or an alkali catalyst, it is excellent in heat resistance and has a low coloring increase rate.
従って、本発明により製造される高液状性パーム系油脂は液状性が高く、サラダ油への使用にも適したものである。また、従来の菜種油主体のサラダ油と比較して、この高液状性パーム系油脂を高配合で調製したサラダ油は、耐熱性に優れており、フライ油、天ぷら油に使用した場合において風味、色等がよい。また、菜種油は今後、バイオディーゼルの普及により、価格が高騰して供給面でも逼迫すると予測されるが、本発明ではパーム油を利用することにより、価格および供給面においても比較的安定したサラダ油を供給することが可能となる。 Accordingly, the highly liquid palm-based fats and oils produced according to the present invention have high liquidity and are suitable for use in salad oil. In addition, compared to conventional rapeseed oil-based salad oil, salad oil prepared with a high blend of this highly liquid palm oil and fat has excellent heat resistance, and when used in frying oil and tempura oil, flavor, color, etc. Is good. In addition, rapeseed oil is expected to increase in price due to the spread of biodiesel in the future, and it will be tight on the supply side. It becomes possible to supply.
以上、本発明の実施形態について述べたが、これらは本発明の例示であり、上記以外の様々な構成を採用することもできる。 As mentioned above, although embodiment of this invention was described, these are illustrations of this invention and various structures other than the above are also employable.
次に、本発明の実施例について説明する。
（実施例１）
ヨウ素価６７のパームオレインを６０℃、減圧下で窒素バブリングを行い、残存水分を５０ｐｐｍ以下にし、Ｌｉｐｏｚｙｍｅ ＴＬ ＩＭ（ノボザイムズ社）を約４ｋｇ充填した直径１０ｃｍのカラムに流速１．３ｋｇ／ｈで通液してエステル交換を行った（工程（Ａ））。得られたエステル交換油脂のＰＰＰ含量は５質量％、Ｐ２Ｏ含量は１９質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３８であった。このエステル交換油脂１０ｋｇをＤｅ Ｓｍｅｔ社のＬａｂ Ｐｉｌｏｔ Ｆｒａｃｔｉｏｎａｔｉｏｎ Ｕｎｉｔ（以降の分別も同設備を用いて行った）を用いて７０℃で完全溶解後、１８℃まで急冷し、１８℃で６０分、その後１４℃で９０分、１１℃で９０分、８℃で１２０分、５℃で１５０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にて、ろ別し、ヨウ素価７９、ＰＰＰ含量０質量％、Ｐ２Ｏ含量９質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４８の液状部を収率６４％で得た（工程（Ｂ））。
なお、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は液体クロマトグラフィーにて、先ずはＯＤＳカラム（ＬｉＣｈｒｏｓｏｒｂ ＲＰ-１８ ５μｍ/ＧＬ−Ｐａｃｋ、ジーエルサイエンス社製）を用いてトリグリセリド種を分画してＰ２Ｏ画分を分取後、Ｐ２Ｏ画分を銀イオンカラム（ＣｈｒｏｍＳｐｈｅｒ ５ Ｌｉｐｉｄｓ、ＶＡＲＩＡＮ社製）を用いてＰＯＰとＰＰＯを分画し、その比を測定した。ヨウ素価は社団法人日本油化学会制定の基準油脂分析試験法２．３．４．１−１９９６に準じて測定した。後述する実施例、比較例においても、同様である。
また、工程（Ａ）におけるエステル交換、工程（Ｂ）における分別除去操作はそれぞれ１回のみ実施された。
Next, examples of the present invention will be described.
Example 1
Nitrogen bubbling of palm olein having an iodine value of 67 at 60 ° C. under reduced pressure was performed at a flow rate of 1.3 kg / h through a 10 cm diameter column packed with about 4 kg of Lipozyme TL IM (Novozymes) with a residual water content of 50 ppm or less. Liquid transesterification was carried out (step (A)). The obtained transesterified oil had a PPP content of 5% by mass, a P 2 O content of 19% by mass, and a POP / (POP + PPO) ratio of 0.38. 10 kg of this transesterified fat / oil was completely dissolved at 70 ° C. using Lab Pilot Fraction Unit of De Smet (the same fractionation was performed using the same equipment), then rapidly cooled to 18 ° C., 60 minutes at 18 ° C., and then Crystallization was carried out at 14 ° C. for 90 minutes, 11 ° C. for 90 minutes, 8 ° C. for 120 minutes, 5 ° C. for 150 minutes, filtered with a filter press (pressurized to 12 bar), iodine value 79, PPP content 0 A liquid part having a mass%, a P 2 O content of 9 mass%, and a POP / (POP + PPO) ratio of 0.48 was obtained in a yield of 64% (step (B)).
The POP / (POP + PPO) ratio was determined by liquid chromatography. First, an ODS column (LiChrosorb RP-18 5 μm / GL-Pack, manufactured by GL Sciences) was used to fractionate triglyceride species to obtain a P 2 O fraction. After fractionation, the P 2 O fraction was fractionated from POP and PPO using a silver ion column (ChromSphere 5 Lipids, manufactured by Varian), and the ratio was measured. The iodine value was measured according to the standard oil analysis test method 2.3.4.1-1996 established by the Japan Oil Chemists' Society. The same applies to Examples and Comparative Examples described later.
Moreover, transesterification in the step (A) and fractionation removal operation in the step (B) were each performed only once.
（比較例５）
ヨウ素価６３のパームオレインを実施例１と同様な方法でエステル交換を行った。得られたエステル交換油脂のＰＰＰ含量は７質量％、Ｐ２Ｏ含量は２１質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３８であった。このエステル交換油脂１０ｋｇを実施例１と同様な方法で晶析、ろ別を行って、ヨウ素価７６、ＰＰＰ含量０質量％、Ｐ２Ｏ含量１３質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率５８％で得た。
工程（Ａ）におけるエステル交換、工程（Ｂ）における分別除去操作はそれぞれ１回のみ実施された。
( Comparative Example 5 )
Transesterification of palm olein having an iodine value of 63 was performed in the same manner as in Example 1. The obtained transesterified oil and fat had a PPP content of 7% by mass, a P 2 O content of 21% by mass, and a POP / (POP + PPO) ratio of 0.38. 10 kg of this transesterified oil and fat was crystallized and filtered by the same method as in Example 1 to obtain an iodine value of 76, a PPP content of 0% by mass, a P 2 O content of 13% by mass, and a POP / (POP + PPO) ratio of 0.49. The liquid part was obtained with a yield of 58%.
The transesterification in the step (A) and the separation and removal operation in the step (B) were each performed only once.
（実施例３）
ヨウ素価６３のパームオレインを実施例１と同様な方法でエステル交換を行った（工程（Ａ））。得られたエステル交換油脂のＰＰＰ含量は７質量％、Ｐ２Ｏ含量は２１質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３８であった。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、１８℃まで急冷し、１８℃で６０分、その後１４℃で９０分、１１℃で９０分、８℃で１２０分、５℃で１２０分、４℃で６０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価７８、ＰＰＰ含量０質量％、Ｐ２Ｏ含量１０質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率５３％で得た（工程（Ｂ））。
また、工程（Ａ）におけるエステル交換、工程（Ｂ）における分別除去操作はそれぞれ１回のみ実施された。
(Example 3)
The transesterification of palm olein having an iodine value of 63 was performed in the same manner as in Example 1 (step (A)). The obtained transesterified oil and fat had a PPP content of 7% by mass, a P 2 O content of 21% by mass, and a POP / (POP + PPO) ratio of 0.38. 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C., then rapidly cooled to 18 ° C., 60 minutes at 18 ° C., 90 minutes at 14 ° C., 90 minutes at 11 ° C., 120 minutes at 8 ° C., 120 minutes at 5 ° C., Crystallization was carried out at 4 ° C. for 60 minutes, and filtered with a filter press (pressurized to 12 bar). The iodine value was 78, the PPP content was 0% by mass, the P 2 O content was 10% by mass, and the POP / (POP + PPO) ratio was 0.49. Was obtained with a yield of 53% (step (B)).
Moreover, transesterification in the step (A) and fractionation removal operation in the step (B) were each performed only once.
（実施例４）
ヨウ素価６３のパームオレインを実施例１と同様な方法でエステル交換を行った（工程（Ａ））。得られたエステル交換油脂のＰＰＰ含量は７質量％、Ｐ２Ｏ含量は２１質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３８であった。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、２４℃まで急冷し、その後３０℃で５０分、２６℃で５０分、２２℃で７０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価７１、ＰＰＰ含量１質量％、Ｐ２Ｏ含量１９質量％の液状部を収率８７％で得た。得られた液状部を７０℃で完全溶解後、１４℃まで急冷し、その後１４℃で６０分、１１℃で９０分、８℃で１２０分、６℃で１２０分、４℃で１２０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価８０、ＰＰＰ含量０質量％、Ｐ２Ｏ含量８質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率６０％で得た。ヨウ素価６３のパームオレインからの収率は５２％であった（工程（Ｂ））。
本実施例では、工程（Ａ）におけるエステル交換は１回のみ実施され、工程（Ｂ）における分別除去操作は２回実施された。
Example 4
The transesterification of palm olein having an iodine value of 63 was performed in the same manner as in Example 1 (step (A)). The obtained transesterified oil and fat had a PPP content of 7% by mass, a P 2 O content of 21% by mass, and a POP / (POP + PPO) ratio of 0.38. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C., then rapidly cooled to 24 ° C., and then subjected to crystallization for 50 minutes at 30 ° C., 50 minutes at 26 ° C., and 70 minutes at 22 ° C., and filter press (pressurized to 12 bar) And a liquid part having an iodine value of 71, a PPP content of 1% by mass and a P2O content of 19% by mass was obtained in a yield of 87%. The obtained liquid part is completely dissolved at 70 ° C. and then rapidly cooled to 14 ° C., and then crystallized at 14 ° C. for 60 minutes, 11 ° C. for 90 minutes, 8 ° C. for 120 minutes, 6 ° C. for 120 minutes, and 4 ° C. for 120 minutes. And filtered with a filter press (pressurized up to 12 bar) to obtain a liquid part having an iodine value of 80, a PPP content of 0% by mass, a P 2 O content of 8% by mass, and a POP / (POP + PPO) ratio of 0.49. Obtained at 60%. The yield of iodine value 63 from palm olein was 52% (step (B)).
In this example, the transesterification in the step (A) was performed only once, and the separation and removal operation in the step (B) was performed twice.
（実施例５）
ヨウ素価６８のパームオレインを実施例１と同様な方法でエステル交換を行った（工程（Ａ））。得られたエステル交換油脂のＰＰＰ含量は５質量％、Ｐ２Ｏ含量は１９質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３８であった。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、１８℃まで急冷し、１８℃で６０分、その後１４℃で９０分、１１℃で９０分、８℃で１２０分、５℃で１２０分、４℃で６０分、３℃で６０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価８３、ＰＰＰ含量０質量％、Ｐ２Ｏ含量４質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率５１％で得た（工程（Ｂ））。また、工程（Ａ）におけるエステル交換、工程（Ｂ）における分別除去操作はそれぞれ１回のみ実施された。
(Example 5)
The transesterification of palm olein having an iodine value of 68 was performed in the same manner as in Example 1 (step (A)). The obtained transesterified oil had a PPP content of 5% by mass, a P 2 O content of 19% by mass, and a POP / (POP + PPO) ratio of 0.38. 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C., then rapidly cooled to 18 ° C., 60 minutes at 18 ° C., 90 minutes at 14 ° C., 90 minutes at 11 ° C., 120 minutes at 8 ° C., 120 minutes at 5 ° C., Crystallization was carried out at 4 ° C. for 60 minutes and at 3 ° C. for 60 minutes, and filtered with a filter press (pressurized up to 12 bar), iodine value 83,
（比較例１）
ヨウ素価６０のパームオレインを実施例１と同様な方法でエステル交換を行った。得られたエステル交換油脂のＰＰＰ含量は１０質量％、Ｐ２Ｏ含量は２６質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３７であった。このエステル交換油脂１０ｋｇを実施例１と同様な方法で晶析、ろ別を行って、ヨウ素価７２、ＰＰＰ含量０．３質量％、Ｐ２Ｏ含量１８質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４４の液状部を収率２６％で得た。ろ過性は非常に悪かった。
(Comparative Example 1)
Transesterification of palm olein having an iodine value of 60 was performed in the same manner as in Example 1. The obtained transesterified oil had a PPP content of 10% by mass, a P 2 O content of 26% by mass, and a POP / (POP + PPO) ratio of 0.37. 10 kg of this transesterified oil and fat was crystallized and filtered in the same manner as in Example 1 to obtain an iodine value of 72, a PPP content of 0.3% by mass, a P 2 O content of 18% by mass, and a POP / (POP + PPO) ratio of 0. .44 liquid part was obtained with a yield of 26%. The filterability was very poor.
（比較例２）
撹拌機のついた反応装置にヨウ素価６７のパームイオレイン１０ｋｇを投入し、６０℃、減圧下で窒素バブリングを行い、残存水分を５０ｐｐｍ以下にした後、窒素気流下で触媒であるナトリウムメトキシド３０ｇを添加した。窒素気流下、６０℃で２時間撹拌し、エステル交換を行った。触媒を除去するために中性になるまで水洗を行った後、減圧下で水分を除去し、エステル交換油脂を収率９２％で得た。得られたエステル交換油脂のＰＰＰ含量は５質量％、Ｐ２Ｏ含量は１９質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３７であった。このエステル交換油脂１０ｋｇを実施例１と同様な方法で晶析、ろ別を行って、ヨウ素価７８、ＰＰＰ含量０質量％、Ｐ２Ｏ含量１１質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４７の液状部を収率６０％で得た。全工程の収率は５６％であった。
(Comparative Example 2)
A reactor equipped with a stirrer was charged with 10 kg of palm iolein having an iodine value of 67, subjected to nitrogen bubbling at 60 ° C. under reduced pressure to reduce the residual moisture to 50 ppm or less, and then sodium methoxide as a catalyst under a nitrogen stream. 30 g was added. The mixture was stirred at 60 ° C. for 2 hours under a nitrogen stream to perform transesterification. After washing with water until neutrality to remove the catalyst, water was removed under reduced pressure to obtain a transesterified oil / fat in a yield of 92%. The obtained transesterified oil had a PPP content of 5% by mass, a P 2 O content of 19% by mass, and a POP / (POP + PPO) ratio of 0.37. 10 kg of this transesterified oil and fat was crystallized and filtered by the same method as in Example 1 to obtain an iodine value of 78, a PPP content of 0% by mass, a P 2 O content of 11% by mass, and a POP / (POP + PPO) ratio of 0.47. The liquid part was obtained with a yield of 60%. The yield for all steps was 56%.
（比較例３）
ヨウ素価５７のパームオレインを実施例１と同様な方法でエステル交換を行った。得られたエステル交換油脂のＰＰＰ含量は１１質量％、Ｐ２Ｏ含量は２８質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比は０．３０であった。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、２８℃まで急冷し、その後３２℃で９０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価６２、ＰＰＰ含量３質量％、Ｐ２Ｏ含量３０質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．３３の液状部を収率８０％で得た(１サイクル目)。この液状部を再度同様な方法でエステル交換を行い、ＰＰＰ含量９質量％、Ｐ２Ｏ含量２４質量％のエステル交換油脂を得た。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、２６℃まで急冷し、その後３２℃で４０分、３０℃で３０分、２８℃で４０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価６６、ＰＰＰ含量２質量％、Ｐ２Ｏ含量２５質量％の液状部を収率８５％で得た(２サイクル目)。得られた液状部を再度同様な方法でエステル交換を行い、ＰＰＰ含量６質量％、Ｐ２Ｏ含量２２質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．２６のエステル交換油脂を得た。このエステル交換油脂１０ｋｇを７０℃で完全溶解後、１９℃まで急冷し、その後２５℃で４５分、２０℃で３０分、１５℃で９０分、１０℃で１２０分、５℃で１２０分晶析を行い、フィルタープレス(１２ｂａｒまで加圧)にてろ別し、ヨウ素価７５、ＰＰＰ含量０．１質量％、Ｐ２Ｏ含量１６質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４７の液状部を収率６６％で得た(３サイクル目)。全工程の収率は４５％であった。
(Comparative Example 3)
Transesterification of palm olein having an iodine value of 57 was performed in the same manner as in Example 1. The obtained transesterified oil had a PPP content of 11% by mass, a P 2 O content of 28% by mass, and a POP / (POP + PPO) ratio of 0.30. 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C. and then rapidly cooled to 28 ° C., followed by crystallization at 32 ° C. for 90 minutes, followed by filtration with a filter press (pressurized to 12 bar), iodine value 62, PPP content 3 A liquid part having a mass%, a P 2 O content of 30 mass%, and a POP / (POP + PPO) ratio of 0.33 was obtained in a yield of 80% (first cycle). This liquid part was transesterified again in the same manner to obtain a transesterified oil and fat having a PPP content of 9% by mass and a P 2 O content of 24% by mass. 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C. and then rapidly cooled to 26 ° C., followed by crystallization at 32 ° C. for 40 minutes, 30 ° C. for 30 minutes, and 28 ° C. for 40 minutes, and filter press (pressurized to 12 bar) And a liquid part having an iodine value of 66, a PPP content of 2% by mass and a P 2 O content of 25% by mass was obtained in a yield of 85% (second cycle). The obtained liquid part was transesterified again in the same manner to obtain a transesterified oil and fat having a PPP content of 6% by mass, a P 2 O content of 22% by mass, and a POP / (POP + PPO) ratio of 0.26. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C. and then rapidly cooled to 19 ° C., and then crystallized at 25 ° C. for 45 minutes, 20 ° C. for 30 minutes, 15 ° C. for 90 minutes, 10 ° C. for 120 minutes, and 5 ° C. for 120 minutes. And a liquid part having an iodine value of 75, a PPP content of 0.1% by mass, a P 2 O content of 16% by mass, and a POP / (POP + PPO) ratio of 0.47 is filtered out using a filter press (pressurized to 12 bar). The yield was 66% (third cycle). The yield for all steps was 45%.
（比較例４）
比較例３の３サイクル目のエステル交換油脂（ＰＰＰ含量６％、Ｐ２Ｏ含量２２％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．２６）を７０℃で完全溶解後１００ｍｌビーカーに９０ｇ採取し、撹拌機で撹拌しながら(２０ｒｐｍ)１２℃まで急冷し、その後２５℃で６０分、２０℃で３０分、１５℃で３０分、１０℃で３０分、５℃で３０分晶析を行い、フィルタープレス(１２ｂｒまで加圧)にてろ別し、ヨウ素価７８、ＰＰＰ含量０％、Ｐ２Ｏ含量１２％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４８の液状部を収率６１％で得た。全工程の収率は４１％であった。
(Comparative Example 4)
90 g of a transesterified oil and fat in the third cycle of Comparative Example 3 (PPP content 6%, P 2 O content 22%, POP / (POP + PPO) ratio 0.26) was completely dissolved at 70 ° C. in a 100 ml beaker and stirred. While stirring at 20 rpm, quench rapidly to 12 ° C, then crystallize at 25 ° C for 60 minutes, 20 ° C for 30 minutes, 15 ° C for 30 minutes, 10 ° C for 30 minutes, 5 ° C for 30 minutes, filter press (Pressure up to 12 br), and a liquid part having an iodine value of 78, a PPP content of 0%, a P 2 O content of 12%, and a POP / (POP + PPO) ratio of 0.48 was obtained in a yield of 61%. The yield for all steps was 41%.
（試験例１：油脂組成物の冷却試験）
実施例１、３〜５および比較例１〜５で得られた油脂組成物を通常の精製（脱酸/脱色/脱臭）を行った。得られた油脂組成物と菜種油とをそれぞれ５０質量％配合したものおよび得られた油脂組成物単独について、ＪＡＳのサラダ油規格をクリアするかを確認するための冷却試験（０℃、５．５ｈ）を行った。結果を表１に示す。
(Test Example 1: Oil composition cooling test)
The oil and fat compositions obtained in Examples 1 and 3 to 5 and Comparative Examples 1 to 5 were subjected to normal purification (deoxidation / decolorization / deodorization). Cooling test (0 ° C., 5.5 h) for confirming whether the oil / fat composition obtained and 50% by mass of rapeseed oil were blended and the obtained oil / fat composition alone satisfied the JAS salad oil standard Went. The results are shown in Table 1.
上記結果より、実施例1、３〜５および比較例２〜４、５で得られた油脂組成物は、菜種油と５０質量％配合した場合、サラダ油規格の冷却試験（０℃、５．５ｈ）をクリアした。実施例1、３〜５および比較例２、４で得られた油脂組成物は単独（１００％）でも冷却試験をクリアした。しかし、比較例１で得られた油脂組成物を菜種油とそれぞれ５０質量％配合した場合は、冷却試験をクリアできず、比較例１で得られた油脂組成物の液状性は十分満足できるものではなかった。
また、実施例1、３〜５、比較例５に比べ、比較例１、３、４では、高液状性パーム系油脂の収率が悪いことがわかった。
From the above results, Examples 1, 3 to 5 and Comparative Examples 2 to 4, fat and oil composition obtained in 5, when rapeseed oil and blended 50% by weight, cooling tests of salad oil standard (0 ° C., 5.5 h) Cleared. The oil and fat compositions obtained in Examples 1 and 3 to 5 and Comparative Examples 2 and 4 cleared the cooling test alone (100%). However, when the oil composition obtained in Comparative Example 1 is blended with 50% by mass of rapeseed oil, the cooling test cannot be cleared, and the liquid property of the oil composition obtained in Comparative Example 1 is not sufficiently satisfactory. There wasn't.
Moreover, compared with Example 1, 3-5, and the comparative example 5 , in the comparative examples 1, 3, and 4, it turned out that the yield of highly liquid palm oil fat is bad.
（試験例２：油脂組成物の色度）
実施例1、３〜５および比較例１〜５で得られた油脂組成物を通常の精製（脱酸/脱色/脱臭）を行って、ロビボンド比色計（Ｔｈｅ Ｔｉｎｔｏｍｅｔｅｒ社製）を用いて色度を測定した（社団法人日本油化学会制定の基準油脂分析試験法２．２．１．１−１９９６に準ずる）。結果を表２に示す。なお、用いたセルのサイズは１インチである。また、表２中のＲは赤色を、Ｙは黄色を示す。
(Test Example 2: Chromaticity of oil composition)
Examples 1, 3 to 5 and Comparative Example 1 to 5 resulting fat and oil composition by performing ordinary purification (deoxidation / bleaching / deodorization), using Lovibond colorimeter (manufactured by The Tintometer Ltd.) color The degree of oil was measured (according to the standard oil analysis method 2.2.1.1-1996 established by the Japan Oil Chemists' Society). The results are shown in Table 2. The cell size used is 1 inch. In Table 2, R represents red and Y represents yellow.
上記結果より、実施例1、３〜５および比較例１、３、４、５で得られた油脂組成物に比べて、比較例２で得られた油脂組成物は色度が非常に高く、他の液状油を、混合油全体を基準として５０質量％配合したとしても、サラダ油として商品にするには耐え難いものであった。また、実施例1、３〜５および比較例１、５で得られた油脂組成物は、比較例３、４で得られた油脂組成物よりもやや色度が低かった。 From the above results, Examples 1, 3 to 5 and Comparative Examples 1, 3 and 4, as compared to the fat composition obtained in 5, the fat or oil composition obtained in Comparative Example 2 is chromaticity is very high, Even if 50% by mass of other liquid oil was blended based on the total mixed oil, it was unbearable to make a product as a salad oil. In Examples 1, 3 to 5 and Comparative Example 1, the fat and oil composition obtained in 5 is slightly chromaticity is lower than the fat and oil composition obtained in Comparative Examples 3 and 4.
（試験例３：油脂組成物の風味試験）
実施例1、３〜５および比較例１〜４、５で得られた油脂組成物を通常の精製（脱酸/脱色/脱臭）を行い、精製直後と缶容器に移し密栓をして２５℃の恒温器に６ヵ月保存後の風味をパネラー１０名が評価した。評価は５点法にて行い、５点：新鮮で非常においしい、４点：非常においしい、３点：おいしい、２点：ややまずい、１点：まずい、とし、平均点を算出した。結果を表３に示す。表３中の評価は比較例３を基準にして、比較例３の評点＋０．３以上を「○」、比較例３の評点−０．３を超え、比較例３の評点＋０．３未満を「△」、比較例３の評点−０．３以下を「×」とした。
(Test Example 3: Flavor test of oil and fat composition)
Examples 1, 3 to 5 and Comparative Examples 1 to 4, for 5 obtained in fat composition of conventional purification (deoxidation / bleaching / deodorising), 25 ° C. and the sealed transferred immediately after the cans purified 10 panelists evaluated the flavor after storage for 6 months in a thermostat. The evaluation was performed by a 5-point method, and 5 points: fresh and very delicious, 4 points: very delicious, 3 points: delicious, 2 points: slightly bad, 1 point: bad, and an average score was calculated. The results are shown in Table 3. The evaluation in Table 3 is based on Comparative Example 3, with a score of Comparative Example 3 +0.3 or more being “◯”, a score of Comparative Example 3 exceeding −0.3, a score of Comparative Example 3 being less than +0.3 “△”, a score of Comparative Example 3 of −0.3 or less was defined as “x”.
上記結果より、実施例1、３〜５および比較例１、５で得られた油脂組成物は、比較例３、４よりも風味が良好であり、風味の点でサラダ油として十分使用できるものであった。また、比較例２で得られた油脂組成物は精製直後でも風味が悪く、サラダ油としての使用には適さないものであった。 From the above results, Examples 1, 3 to 5 and Comparative Example 1, the fat and oil composition obtained in 5 has good taste than the comparative examples 3 and 4, but sufficiently usable as salad oil in terms of flavor there were. In addition, the oil and fat composition obtained in Comparative Example 2 had a bad flavor even immediately after purification and was not suitable for use as a salad oil.
（試験例４：油脂組成物の空加熱試験）
実施例１、５および比較例１〜４、５で得られた油脂組成物を通常の精製（脱酸/脱色/脱臭）を行った後、それぞれにシリコーン２ｐｐｍを添加した。このようにしてシリコーンが添加された実施例１、５および比較例１〜４、５の油脂組成物と菜種油（シリコーン２ｐｐｍ含有）とをそれぞれ５０質量％配合した油脂組成物を、直径１８ｃｍの丸底磁製皿に３００ｇ採取し、１８０℃、５時間空加熱を行った。比較として菜種油（シリコーン２ｐｐｍ含有）の空加熱試験も行った。常温まで戻した後、アニシジン価、粘度上昇率（空加熱前との比較）および着色上昇率（空加熱前との色度比較）を比較した。結果を表４に示す。
アニシジン価、粘度、色度は、以下のように測定した。
アニシジン価は、社団法人日本油化学会制定の基準油脂分析試験法２．５．３−１９９６に準じて測定した。粘度は、社団法人日本油化学会制定の基準油脂分析試験法２．２．１０．１−１９９６に準じて測定した。色度は、試験例２と同様に社団法人日本油化学会制定の基準油脂分析試験法２．２．１．１−１９９６に準じて測定した。
また、粘度上昇率および着色上昇率は、以下の式から算出した。
粘度上昇率（％）＝（空加熱後の粘度／空加熱前の粘度）×１００−１００
着色上昇率（％）＝（空加熱後の色度／空加熱前の色度）×１００−１００
(Test Example 4: Empty heating test of oil and fat composition)
The oil and fat compositions obtained in Examples 1 and 5 and Comparative Examples 1 to 4 and 5 were subjected to normal purification (deoxidation / decolorization / deodorization), and then 2 ppm of silicone was added to each. Thus, the oil-and-fat composition which mix | blended 50 mass% of the oil-and-fat composition of Examples 1 and 5 and Comparative Examples 1-4 and 5 and the rapeseed oil (2 ppm of silicones) to which silicone was added in this way is a 18-cm diameter round oil composition. 300 g was collected on a bottom porcelain dish and heated at 180 ° C. for 5 hours. As a comparison, an air heating test of rapeseed oil (containing 2 ppm of silicone) was also conducted. After returning to normal temperature, the anisidine value, viscosity increase rate (comparison with before air heating), and color increase rate (color comparison with before air heating) were compared. The results are shown in Table 4.
The anisidine value, viscosity, and chromaticity were measured as follows.
The anisidine value was measured according to the standard oil analysis method 2.5.3-1996 established by the Japan Oil Chemists' Society. The viscosity was measured according to the standard oil analysis test method 2.2.10.1-1996 established by the Japan Oil Chemists' Society. The chromaticity was measured according to the standard oil analysis method 2.2.1.1-1996 established by the Japan Oil Chemists' Society as in Test Example 2.
The viscosity increase rate and the color increase rate were calculated from the following formulas.
Viscosity increase rate (%) = (viscosity after air heating / viscosity before air heating) × 100-100
Color increase rate (%) = (chromaticity after air heating / chromaticity before air heating) × 100-100
上記結果より、実施例１、５および比較例１〜４、５で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合した油脂組成物は、サラダ油の主体である菜種油よりも耐熱性が良かった。比較例２で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合したものは、実施例１、５および比較例３、４、５で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合したものよりも、着色上昇率がかなり劣っていた。また、実施例１、５および比較例１、５と比較例３、４で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合した油脂組成物を比較すると、比較例３、４で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合したものが、着色上昇率がやや劣った。 From the above results, the fat composition obtained by blending 50% by mass of the fat composition obtained in Examples 1 and 5 and Comparative Examples 1 to 4 and 5 and rapeseed oil has higher heat resistance than rapeseed oil, which is the main component of salad oil. Was good. What mixed 50 mass% of the oil-fat composition obtained in Comparative Example 2 and rapeseed oil, respectively, 50 masses of the oil-fat composition obtained in Examples 1 and 5 and Comparative Examples 3 , 4 and 5 and rapeseed oil. %, The increase in coloration was considerably inferior to that blended with%. Moreover, when the oil-fat composition which mix | blended 50 mass% of the oil-fat composition and rapeseed oil obtained in Example 1 , 5 and Comparative Example 1 , 5 and Comparative Example 3, 4, respectively was compared, it obtained in Comparative Example 3, 4. What mixed 50 mass% of the obtained oil-fat composition and rapeseed oil each had a slightly inferior coloring increase rate.
（試験例５：油脂組成物の天ぷら風味試験）
実施例１および比較例１〜４、５で得られた油脂組成物を通常の精製（脱酸/脱色/脱臭）を行った。実施例１および比較例１〜４、５の油脂組成物に、混合油全体を基準として菜種油を５０質量％配合した油脂組成物を、直径１８ｃｍの丸底磁製皿に３００ｇ採取した。１７０℃で下記の材料を用いて天ぷらを作り、天ぷらの風味をパネラー１０名が評価した。評価は試験例３と同様におこなった。なお、比較として菜種油の風味試験も行った。結果を表５に示す。また、天ぷらの油っぽさについてもパネラー１０名が評価した。評価は５点法にて行い、５点：油っぽくない、４点：若干油っぽい、３点：やや油っぽい、２点：油っぽい、１点：非常に油っぽい、とし、平均点を算出した。結果を表６に示す。表５、６中の評価は比較例３を基準にして、比較例３の評点＋０．３以上を「○」、比較例３の評点−０．３を超え、比較例３の評点＋０．３未満を「△」、比較例３の評点−０．３以下を「×」とした。
使用した材料： 海老 ２尾、南瓜 ２切れ
バッター組成： 卵 ５０ｇ、水 １５０ｇ、小麦粉 １００ｇ
(Test Example 5: Tempura flavor test of oil and fat composition)
Example 1 Contact and Comparative Examples 1-4, the oil or fat composition obtained in 5 was carried out the usual purification (deoxidation / bleaching / deodorization). Example 1 Contact and Comparative Examples 1-4, the oil composition 5, a fat composition containing 50 wt% rapeseed oil across mixed oil based, and 300g collected in a round bottom porcelain dish with a diameter of 18cm. Tempura was made at 170 ° C. using the following materials, and 10 panelists evaluated the flavor of tempura. Evaluation was performed in the same manner as in Test Example 3. For comparison, a rapeseed oil flavor test was also conducted. The results are shown in Table 5. Ten panelists also evaluated the oiliness of tempura. Evaluation is performed by a 5-point method, 5 points: not oily, 4 points: slightly oily, 3 points: slightly oily, 2 points: oily, 1 point: very oily The average score was calculated. The results are shown in Table 6. Evaluations in Tables 5 and 6 are based on Comparative Example 3, with a score of Comparative Example 3 +0.3 or more being “◯”, a score of Comparative Example 3 exceeding −0.3, and a score of Comparative Example 3 +0.3. Less than “△”, the score of Comparative Example 3 −0.3 or less was “x”.
Materials used: 2 shrimp, 2 slices of sea bream Batter composition: 50g egg, 150g water, 100g flour
上記結果より、菜種油を５０質量％配合した実施例１および比較例１、５で得られた油脂組成物で揚げた天ぷらは、菜種油を５０質量％配合した比較例３、４で得られた油脂組成物および菜種油で揚げた天ぷらよりも風味が良好であった。さらに、菜種油を５０質量％配合した実施例１、比較例５で得られた油脂組成物で揚げた天ぷらは、菜種油を５０質量％配合した比較例１、３、４で得られた油脂組成物や菜種油で揚げた天ぷらよりも油っぽくなく軽い感じで仕上がった。従って、本発明の製造方法で得られた油脂組成物は、揚げ物の油っぽさが低減されて軽い感じに仕上がるという効果を有する天ぷら油として使用できることがわかった。また、比較例２で得られた油脂組成物は風味が悪く、天ぷら油としての使用には適さないものであった。 From the above results, Comparative Example and Example 1 Contact blended with rapeseed oil 50 wt% 1, 5 tempura obtained fried in fat composition was obtained in Comparative Example 3 and 4 was blended rapeseed 50 wt% The flavor was better than the tempura fried with the oil composition and rapeseed oil. Furthermore, the tempura fried in the oil composition obtained in Example 1 and Comparative Example 5 containing 50% by mass of rapeseed oil was the oil composition obtained in Comparative Examples 1, 3, and 4 containing 50% by mass of rapeseed oil. Finished with a lighter and lighter feel than tempura fried with rapeseed oil. Therefore, it was found that the oil and fat composition obtained by the production method of the present invention can be used as a tempura oil having the effect of reducing the oiliness of the fried food and finishing it light. Moreover, the fat and oil composition obtained in Comparative Example 2 had a bad flavor and was not suitable for use as tempura oil.
Claims (4)
（Ｂ）前記工程（Ａ）で得られた該エステル交換油脂から、分別により、ＳＳＳ（Ｓは飽和脂肪酸で、ＳＳＳは飽和脂肪酸３つで構成されるトリグリセリドを意味する）を除去し、高液状性パーム系油脂を得る工程とを含み、
前記高液状性パーム系油脂において、ＰＯＰ／（ＰＯＰ+ＰＰＯ）比が０．６以下であり、Ｐ ２ Ｏ含量が１２質量％以下である加熱調理用の高液状性パーム系油脂の製造方法。
ＰＯＰは、１位および３位がパルミチン酸、２位がオレイン酸で構成されるトリグリセリドを示し、ＰＰＯは１および２位がパルミチン酸、３位がオレイン酸で構成されるトリグリセリド、と２および３位がパルミチン酸、１位がオレイン酸で構成されるトリグリセリドとを意味する。
Ｐ ２ Ｏはパルミチン酸２つとオレイン酸１つで構成されるトリグリセリドを意味する。 (A) iodine value greater than 63, 85 following palm based fat, a step of randomly transesterified with lipase,
(B) From the transesterified oil and fat obtained in the step (A), SSS (S is a saturated fatty acid, SSS means a triglyceride composed of three saturated fatty acids) is removed by fractionation, and is highly liquid. A step of obtaining a functional palm oil and fat,
In the high liquid resistance palm based fat, POP / (POP + PPO) ratio Ri der 0.6, a method of producing high liquid resistance palm based fat for cooking P 2 O content is not more than 12 wt% .
POP is a triglyceride composed of palmitic acid at positions 1 and 3 and oleic acid at position 2, PPO is a triglyceride composed of palmitic acid at positions 1 and 2 and oleic acid at positions 3 and 2 and 3 It means a triglyceride whose position is palmitic acid and whose position is composed of oleic acid.
P 2 O means a triglyceride composed of two palmitic acids and one oleic acid.
前記工程（Ａ）におけるエステル交換は複数回実施せず、
前記工程（Ｂ）において、前記エステル交換油脂から、分別によりＳＳＳ（Ｓは飽和脂肪酸で、ＳＳＳは飽和脂肪酸３つで構成されるトリグリセリドを意味する）を除去する操作を１回以上実施する加熱調理用の高液状性パーム油脂の製造方法。 In the manufacturing method of the highly liquid palm-type fats and oils for heat cooking of Claim 1,
The transesterification in the step (A) is not performed a plurality of times,
In the step (B), cooking is performed by performing at least one operation of removing SSS (S is a saturated fatty acid, SSS means a triglyceride composed of three saturated fatty acids) from the transesterified oil and fat by fractionation. For producing highly liquid palm oils and fats for use.
前記工程（Ａ）では、前記パーム系油脂として、パーム油を１回以上分別して得られたヨウ素価６３以上のパームオレインを使用する加熱調理用の高液状性パーム系油脂の製造方法。 In the manufacturing method of the highly liquid palm-type fats and oils for heat cooking of Claim 1 or 2,
In the said process (A), the manufacturing method of the highly liquid palm oil fat for heating cooking which uses the palm olein of the iodine number 63 or more obtained by fractionating palm oil once or more as said palm oil fat.
前記工程（Ｂ）において、分別をドライ分別にて行う加熱調理用の高液状性パーム系油脂の製造方法。 In the manufacturing method of the highly liquid palm-type fats and oils for heat cooking in any one of Claims 1 thru | or 3,
In the step (B), a method for producing a highly liquid palm-based oil / fat for cooking , wherein the fractionation is performed by dry fractionation.
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