JP5161465B2 - Method for producing highly liquid palm oil and highly liquid palm oil - Google Patents
Method for producing highly liquid palm oil and highly liquid palm oil Download PDFInfo
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- 150000004671 saturated fatty acids Chemical class 0.000 claims description 9
- 108090001060 Lipase Proteins 0.000 claims description 6
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- 235000019421 lipase Nutrition 0.000 claims description 6
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 6
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- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
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Description
本発明は、酵素的エステル交換および分別を繰り返すことによりパーム系油脂から高液状性油を得る、高液状性パーム油の製造方法および高液状性パーム油に関する。 The present invention relates to a method for producing a highly liquid palm oil and a highly liquid palm oil, in which a highly liquid oil is obtained from palm-based fats and oils by repeating enzymatic transesterification and fractionation.
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 for obtaining highly liquid oil from palm-based fats and oils, 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の高液状性パーム油を得ている。得られた高液状性パーム油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 oil having an iodine value of 70. The obtained highly liquid palm oil alone clears the salad oil cooling test, but the yield is low and the production time is also long.
非特許文献３には、化学的エステル交換と分別とを行うことが記載されている。パーム油をアルカリ触媒を用いてエステル交換を行い、触媒除去後、分別にて高融点部を除去して液状部を得ている。ただし、この方法も触媒除去が煩雑で収率が悪いうえ、液状性も十分ではない。
上述の通り、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, 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油を得る方法がある（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を得ることは依然として困難であった。 In order to solve the above problems, there is a method of obtaining high-liquid palm oil by enzymatic transesterification of palm 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 other highly liquid oils is used as a raw material, and a high-liquid oil is obtained in a high yield using palm-based fats alone. Was still difficult.
本発明は上記事情に鑑みてなされたものであり、簡便な操作により、収率よく、液状性の高められたパーム油を製造する方法および高液状性パーム油を提供するものである。 The present invention has been made in view of the above circumstances, and provides a method for producing palm oil with improved liquidity and high liquid palm oil by a simple operation with high yield.
本発明によれば、（Ａ）パーム系油脂を、ランダムエステル交換能を有する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において得られたエステル交換油脂を分別して、ＳＳＳ（Ｓは飽和脂肪酸、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）を除去する工程と、
を含むパーム油の製造方法において、前記工程（Ａ）および（Ｂ）からなる一連の工程を２回以上繰り返す、高液状性パーム油の製造方法が提供される。
According to the present invention, (A) a step of transesterifying palm oil fat using a lipase having random transesterification ability ;
(B) The step of separating the transesterified oil and fat obtained in the step of transesterification to remove SSS (S means saturated fatty acid, SSS means triglyceride composed of three saturated fatty acids);
In the manufacturing method of the palm oil containing A, the manufacturing method of the highly liquid palm oil which repeats the series of processes which consist of the said process (A) and (B) twice or more is provided.
本発明の製造方法は、パーム系油脂の液状性を高めるために、リパーゼを用いたエステル交換を行った後、分別で高融点トリグリセリドを除去するという一連のサイクルを繰り返すことを特徴とする。パーム系油脂の酵素的エステル交換を行うことにより、油脂中の飽和脂肪酸を高融点のトリ飽和脂肪酸グリセリドとし、その後分別にてこれを除去する。この一連の工程を２回以上繰り返すことによって、油脂中の飽和脂肪酸を著しく減じることができ、液状性が向上される。
また、本発明ではリパーゼを用いた酵素的エステル交換を行うため、化学的エステル交換を用いる場合と比較して、水洗などの触媒除去工程が不要で操作が簡便であり、収率も良い。分別でも特に複雑な操作は必要とされず、要する時間も比較的短時間である。また、アルカリ触媒を用いないため、得られた液状油の風味が良好であり、色が濃くなることもない。
The production method of the present invention is characterized by repeating a series of cycles in which high-melting triglycerides are removed by fractionation after transesterification using lipase in order to enhance the liquidity of palm-based fats and oils. By performing the transesterification of palm oil and fat, the saturated fatty acid in the oil and fat is converted to a high-saturation tri-saturated fatty acid glyceride, which is then separated and removed. By repeating this series of steps twice or more, the saturated fatty acid in the oil and fat can be remarkably reduced, and the liquidity is improved.
Further, in the present invention, enzymatic transesterification using lipase is performed, so that a catalyst removal step such as water washing is unnecessary and the operation is simple and the yield is good as compared with the case of using chemical transesterification. Even the separation does not require a particularly complicated operation, and the time required is also relatively short. Moreover, since an alkali catalyst is not used, the flavor of the obtained liquid oil is favorable and a color does not become dark.
また、本発明によれば、工程（Ａ）後に工程（Ｂ）を行う一連の操作を３回以上繰り返す、高液状性パーム油の製造方法が提供される。
さらに、本発明によれば、工程（Ｂ）において、分別をドライ分別により行う、高液状性パーム油の製造方法が提供される。
Moreover, according to this invention, the manufacturing method of highly liquid palm oil which repeats a series of operation which performs a process (B) after a process (A) 3 times or more is provided .
Et al is, according to the present invention, in the step (B), a fractionated by dry fractionation, the method of producing a high liquid resistance palm oil is provided.
さらに、本発明によれば、上記本発明における製造方法により得られる高液状性パーム油であって、
（ｉ）ＰＰＰ（Ｐはパルミチン酸、ＰＰＰはパルミチン酸３つで構成されるトリパルミチンを意味する）含量が０．２質量％以下、
（ｉｉ）Ｐ２Ｏ（Ｏはオレイン酸、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１６質量％以下、
（ｉｉｉ）ＰＯＰ／（ＰＯＰ＋ＰＰＯ）（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を意味し、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）比が０．３以上、０．６以下、
（ｉｖ）ヨウ素価が７０以上、
である高液状性パーム油が提供される。
Furthermore, according to the present invention, high-liquid palm oil obtained by the production method of the present invention ,
(I) PPP (P means palmitic acid, PPP means tripalmitin composed of three palmitic acids) content is 0.2 mass% or less,
(Ii) P 2 O (O means oleic acid, P 2 O means triglyceride composed of two palmitic acids and one oleic acid) content of 16% by mass or less,
(Iii) POP / (POP + PPO) (POP means triglyceride composed of 1 and 3 positions palmitic acid, 2 position oleic acid, PPO 1 and 2 position palmitic acid, 3 position composed of oleic acid The triglyceride and the triglyceride composed of palmitic acid at positions 2 and 3 and oleic acid at position 1)
(Iv) iodine value is 70 or more,
A highly liquid palm oil is provided.
さらに、本発明によれば、上記本発明における高液状性パーム油を単独でまたは他の液状油と混合して得られるサラダ油が提供される。
本発明では、サラダ油に高液状性パーム油を用いることによって、耐熱性が向上する。従って、通常の菜種油を主体としたサラダ油よりも長持ちし、廃油処理などを考慮すると環境面からも良い。
Furthermore, according to this invention, the salad oil obtained by mixing the high-liquid palm oil in the said this invention individually or with another liquid oil is provided.
In this invention, heat resistance improves by using highly liquid palm oil for salad oil. Therefore, it lasts longer than normal salad oil mainly composed of rapeseed oil, and from the viewpoint of environment, considering waste oil treatment and the like.
本発明によれば、簡便な方法を用いて、液状性が高く、また風味のよいサラダ油に適した高液状性パーム油を高い収率で得ることができる。さらに、高液状性パーム油を用いるので、通常の菜種油を主体としたサラダ油よりも長持ちし、廃油処理などを考慮すると環境に優しいサラダ油を提供することができる。 According to the present invention, a highly liquid palm oil suitable for salad oil having a high liquidity and a good flavor can be obtained in a high yield using a simple method. Furthermore, since high-liquid palm oil is used, it can last longer than normal rapeseed oil-based salad oil, and can provide environmentally friendly salad oil in consideration of waste oil treatment.
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.
本発明の製造方法の工程フローを図１に示す。本発明の方法は、パーム系油脂の液状性を高めるために、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することにより高融点トリグリセリドを除去するという一連のサイクルを２回以上繰り返すことを特徴とする。 A process flow of the manufacturing method of the present invention is shown in FIG. The method of the present invention comprises a series of cycles in which high melting point triglycerides are removed by separating the solid part and the liquid part after transesterification using lipase in order to enhance the liquid property of the palm-based fats and oils. Repeated twice or more.
図２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２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。さらに、この一連の工程を繰り返すことによって、より液状性を高めることができる。
FIG. 2 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. 2). 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. Furthermore, by repeating this series of steps, liquidity can be further enhanced.
本発明では、酵素的エステル交換を行うため、化学的エステル交換を用いるシステムよりも、高収率で風味の良い高液状性パーム油を得ることができる。また、酵素的エステル交換を用いる方法は触媒除去のための煩雑な作業を必要とせず、廃水量が低減され、環境面でも優れている。従って、操作も簡便なため、設備費およびユーティリティーコストも大幅に低減することができる。 In the present invention, since the enzymatic transesterification is performed, a highly liquid palm oil having a higher yield and a better flavor than a system using chemical transesterification can be obtained. In addition, the method using enzymatic transesterification does not require complicated work for removing the catalyst, reduces the amount of waste water, and is excellent in terms of environment. Therefore, since the operation is simple, the equipment cost and utility cost can be greatly reduced.
本発明で原料として使用されるパーム系油脂の語は、精製および未精製のパーム油、および一回以上の分別によって得られたパームオレインを含む。原料として、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。しかしながら、本発明では、他の液状性の高い油脂を混合しなくても、パーム系油脂原料から高液状性のパーム油を得ることができる。従って、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。 The term palm oil and fat used as a raw material in the present invention includes refined and unrefined palm oil and palm olein obtained by one or more fractionations. As a raw material, it may be used alone or mixed with other fats and oils. However, in the present invention, high-liquid palm oil can be obtained from the palm-based oil / fat raw material without mixing other high-liquid oil / fat. Therefore, when palm fats and oils occupy most of the raw material, for example, when palm 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.
酵素的エステル交換に使用するリパーゼとしては、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。 The lipase used for the 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.
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.
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。 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.
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。分別は複数回行うため、１回目およびそれ以降の分別と、最後の分別とにおいてそれぞれ条件を変えてもよい。好ましくは、最後の分別以外は、ＰＰＰなどのトリ飽和脂肪酸グリセリド（ＳＳＳ）のみを除去するような条件で行う。この段階では必ずしもＳＳＳを完全に除去する必要はなく、２〜３質量％程度残存しても良い。むしろ、最後の分別以外は分別時間、収率を考慮した場合、ＳＳＳが２〜３質量％程度残存するような条件で行った方が良い。このような分別条件としては、例えば、分別温度を２５〜３５℃程度で、３０分〜２時間程度行うのが良い。 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. Since the separation is performed a plurality of times, the conditions may be changed in the first and subsequent separations and the last separation. Preferably, except for the last fractionation, it is carried out under conditions that remove only tri-saturated fatty acid glycerides (SSS) such as PPP. At this stage, it is not always necessary to completely remove SSS, and about 2 to 3% by mass may remain. Rather, when considering the fractionation time and the yield other than the last fractionation, it is better to carry out under conditions such that about 2 to 3% by mass of SSS remains. As such a separation condition, for example, the separation temperature is preferably about 25 to 35 ° C. and about 30 minutes to 2 hours.
一方、最後の分別では、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時間程度行うのが良い。 On the other hand, in the last fractionation, it is preferable to remove SSS almost completely and to remove P 2 O, which is a medium melting point, to some extent in order to improve liquidity. As such a separation condition, for example, the final temperature of the separation is preferably about 0 to 10 ° C. and about 30 minutes to 3 hours.
最終液状部（油脂組成物）はＰＰＰが０．２質量％以下、Ｐ２Ｏが１６質量％以下であると、菜種油と５０％配合でサラダ油規格の冷却試験をクリアする。さらに、ＰＰＰが０．０５質量％未満、Ｐ２Ｏを１２質量％以下であると単独でサラダ油規格の冷却試験をクリアする。
最後の分別以外はＳＳＳが少し残存する程度の厳しくない条件で分別を行った場合、高収率を維持しつつ工程の煩雑化を回避することができる。
When the final liquid part (oil composition) has a PPP of 0.2% by mass or less and a P 2 O content of 16% by mass or less, the rapeseed oil and 50% blending clear the cooling test of the salad oil standard. Furthermore, PPP is less than 0.05 wt%, to clear the cooling test salad oil standards alone when the P 2 O is 12 wt% or less.
Except for the last fractionation, when the separation is performed under conditions that are not so severe that a little SSS remains, complication of the process can be avoided while maintaining a high yield.
酵素的エステル交換−分別の一連の操作は２回以上繰り返し、好ましくは３回以上繰り返す。このような方法により、高配合でサラダ油を調製できる高液状性パーム油が得られる。酵素的エステル交換−分別の一連の操作を１回行う場合でも上記に該当する油脂組成物を得ることは可能であるが、１回のみの操作では高収率でＰＰＰの少ないパーム系油脂を得ることは困難である。すなわち、上記一連の操作１回のみでＰＰＰを完全に除去しようとすると分別条件が厳しくなり、収率が悪くなる。一方、収率を良くしようとすると、得られた油脂組成物が上記の好ましいＰＰＰおよびＰ２Ｏ範囲を逸脱し、充分な液状性が得られなくなる可能性がある。 The series of operations of enzymatic transesterification-fractionation is repeated twice or more, preferably three or more times. By such a method, highly liquid palm oil which can prepare salad oil by high mixing | blending is obtained. Even when a series of operations of enzymatic transesterification-fractionation is performed once, it is possible to obtain the oil composition corresponding to the above, but a palm-based oil with a high yield and a small amount of PPP can be obtained by a single operation. It is difficult. That is, if the PPP is completely removed by only one series of operations described above, the separation conditions become strict and the yield deteriorates. On the other hand, if the yield is to be improved, the obtained oil / fat composition may depart from the preferred PPP and P 2 O ranges described above, and sufficient liquidity may not be obtained.
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油における、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 finally obtained highly liquid palm oil is preferably 0.3 or more and 0.6 or less, more preferably 0.4 or more and 0.55. It is as follows.
図３に、ＰＯＰ／ＰＰＯ比と融点との関係を示す。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. 3 shows the relationship between the POP / PPO ratio and the melting point. 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.
一連の操作の繰り返し回数は、製造コスト等を考慮して、２〜４回程度が好ましい。 The number of repetitions of the series of operations is preferably about 2 to 4 times in consideration of manufacturing costs and the like.
本発明の方法により製造されるパーム油は、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油は、ＰＰＰ含量が０．２質量％以下、Ｐ２Ｏ含量が１６質量％以下である。該範囲内で、高液状性パーム油は菜種油の配合が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。
Palm oil produced by the method of the present invention has high liquidity. Specifically, the highly liquid palm oil of the present invention has a PPP content of 0.2% by mass or less and a P 2 O content of 16% by mass or less. Within this range, the high-liquid palm oil can clear 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、本発明の高液状性パーム油は、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油は、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, in the highly liquid palm oil of the present invention, the POP ratio is 0.3 or more and 0.6 or less based on the total of POP and PPO, and POP relative to PPO compared to normal palm oil and fat. The ratio 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 oil of the present invention has higher liquidity than a composition having the same P 2 O content not transesterified.
本発明の高液状性パーム油は、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 oil of 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、本発明の高液状性パーム油は、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 oil of this invention is manufactured without using an alkali catalyst in the transesterification, it has a good flavor and low chromaticity. Moreover, compared with transesterification oil using rapeseed oil or an alkali catalyst, it is excellent in heat resistance and has a low coloring increase rate.
従って、本発明の高液状性パーム油は液状性が高く、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、本発明の高液状性パーム油を高配合で調製したサラダ油は、耐熱性に優れており、フライ油に使用した場合にも長持ちする。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。 Therefore, the highly liquid palm oil of the present invention has high liquidity and is suitable for use in salad oil. Moreover, compared with the conventional rapeseed oil-based salad oil, the salad oil prepared by blending the high-liquid palm oil of the present invention with a high blending is excellent in heat resistance and also lasts long when used as a frying oil. In addition, rapeseed oil is expected to increase in price due to the spread of biodiesel in the future, and the supply side will be tight, but in the present invention, by using palm oil, salad oil that is relatively stable in price and supply side can be obtained. 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.
（実施例１）
ヨウ素価５７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。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０．３であり、ほぼランダム化されていた。このエステル交換油脂１０ｋｇをＤｅ Ｓｍｅｔ社のＬａｂ Ｐｉｌｏｔ Ｆｒａｃｔｉｏｎａｔｉｏｎ Ｕｎｉｔ（１０ｋｇ、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、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、同条件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、再度同条件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９０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１４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)。パームオレインからの収率は４５％であった。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（例えば、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（例えば、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。
Example 1
Nitrogen bubbling of palm olein with an iodine value of 57 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. The solution was transesterified. The obtained transesterified oil and fat had a PPP content of 11% by mass, a P 2 O content of 28% by mass, and a POP / (POP + PPO) ratio of 0.3, which was almost randomized. 10 kg of this transesterified oil / fat was completely dissolved at 70 ° C. using Lab Pilot Fraction Unit (10 kg, the following fractionation was also performed using the same equipment) manufactured by De Smet, and then rapidly cooled to 28 ° C. and then 90 ° C. at 32 ° C. Perform crystallization, filter with a filter press (pressurize up to 12 bar), and remove the liquid part with an iodine value of 62, a PPP content of 3% by mass, a P 2 O content of 30% by mass, and a POP / (POP + PPO) ratio of 0.33. Yield was 80% (first cycle). This liquid part was subjected to nitrogen bubbling under reduced pressure at 60 ° C. to reduce the residual moisture to 50 ppm or less, and transesterification was performed under the same conditions 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 subjected to nitrogen bubbling under reduced pressure at 60 ° C. to reduce the residual moisture to 50 ppm or less, and transesterification was performed again under the same conditions. The PPP content was 6% by mass, the P 2 O content was 22% by mass, and POP / ( A transesterified oil with a POP + PPO ratio of 0.26 was obtained. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C., 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 90 minutes, and 5 ° C. for 120 minutes. The liquid part having an iodine value of 75, a PPP content of 0.1% by mass, a P 2 O content of 14% by mass, and a POP / (POP + PPO) ratio of 0.47 is separated by a filter press (pressurized up to 12 bar). The yield was 66% (third cycle). The yield from palm olein was 45%. The POP / (POP + PPO) ratio was determined by liquid chromatography. First, an ODS column (for example, LiChrosorb RP-18 5 μm / GL-Pack, manufactured by GL Sciences) was used to fractionate triglyceride species to obtain P 2 O. After fractionation, the P 2 O fraction was fractionated from POP and PPO using a silver ion column (for example, ChromSpher 5 Lipids, manufactured by Varian), and the ratio was measured.
（実施例２）
実施例１の３サイクル目の分別前のエステル交換油脂（ＰＰＰ含量６質量％、Ｐ２Ｏ含量２２質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．２６）を７０℃で完全溶解後２０００ｍｌビーカーに１２００ｇ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７６、ＰＰＰ含量０質量％、Ｐ２Ｏ含量１６質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４８の液状部を収率６４％で得た。パームオレインからの収率は４４％であった。
(Example 2)
The transesterified oil (PPP content 6% by mass, P 2 O content 22% by mass, POP / (POP + PPO) ratio 0.26) before fractionation in the third cycle of Example 1 was completely dissolved at 70 ° C. and then 1200 g in a 2000 ml beaker. The sample was sampled and rapidly cooled to 12 ° C. while stirring with a stirrer (20 rpm), followed by crystallization at 25 ° C. for 60 minutes, 20 ° C. for 30 minutes, 15 ° C. for 30 minutes, and 10 ° C. for 30 minutes. The pressure was reduced to 12 bar, and a liquid part having an iodine value of 76, a PPP content of 0% by mass, a P 2 O content of 16% by mass, and a POP / (POP + PPO) ratio of 0.48 was obtained in a yield of 64%. The yield from palm olein was 44%.
（実施例３）
実施例１の３サイクル目の分別前のエステル交換油脂（ＰＰＰ含量６質量％、Ｐ２Ｏ含量２２質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．２６）を７０℃で完全溶解後２０００ｍｌビーカーに１２００ｇ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(１２ｂａｒまで加圧)にてろ別し、ヨウ素価７８、ＰＰＰ含量０質量％、Ｐ２Ｏ含量１２質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率６１％で得た。パームオレインからの収率は４１％であった。
(Example 3)
The transesterified oil (PPP content 6% by mass, P 2 O content 22% by mass, POP / (POP + PPO) ratio 0.26) before fractionation in the third cycle of Example 1 was completely dissolved at 70 ° C. and then 1200 g in a 2000 ml beaker. The sample was sampled and rapidly cooled to 12 ° C. while stirring with a stirrer (20 rpm), and then crystallized at 25 ° C. for 60 minutes, 20 ° C. for 30 minutes, 15 ° C. for 30 minutes, 10 ° C. for 30 minutes, and 5 ° C. for 30 minutes. And filtered with a filter press (pressurized to 12 bar) to obtain a liquid part having an iodine value of 78, a PPP content of 0% by mass, a P 2 O content of 12% by mass, and a POP / (POP + PPO) ratio of 0.49. %. The yield from palm olein was 41%.
（比較例１）
実施例１の１サイクル目の分別前のエステル交換油脂（ＰＰＰ含量１１質量％、Ｐ２Ｏ含量２８質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．３０）１０ｋｇをＤｅ Ｓｍｅｔ社のＬａｂ Ｐｉｌｏｔ Ｆｒａｃｔｉｏｎａｔｉｏｎ Ｕｎｉｔ（１０ｋｇ）を用いて、７０℃で完全溶解後、２８℃まで急冷し、その後３２℃で９０分、２５℃で４５分、２０℃で３０分、１５℃で９０分、１０℃で９０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７２、ＰＰＰ含量０．５質量％、Ｐ２Ｏ含量１８質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４５の液状部をパームオレインからの収率１８％で得た。ろ過性は非常に悪かった。
(Comparative Example 1)
10 kg of transesterified oil and fat (PPP content 11% by mass, P 2 O content 28% by mass, POP / (POP + PPO) ratio 0.30) before fractionation in the first cycle of Example 1 was supplied by De Smet Lab Pilot Fractionation Unit ( 10 kg), after complete dissolution at 70 ° C., rapidly cool to 28 ° C., then, 32 ° C. for 90 minutes, 25 ° C. for 45 minutes, 20 ° C. for 30 minutes, 15 ° C. for 90 minutes, 10 ° C. for 90 minutes, Crystallization is carried out at 5 ° C. for 120 minutes, and filtered with a filter press (pressurized up to 12 bar). The iodine value is 72, the PPP content is 0.5 mass%, the P 2 O content is 18 mass%, and the POP / (POP + PPO) ratio is 0. .45 liquid part was obtained in 18% yield from palm olein. 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５７のパームオレイン１ｋｇ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、２０℃まで冷却して窒素気流下で触媒であるナトリウムメトキシド３ｇを添加した。窒素気流下、２０℃で４８時間撹拌後、フィルタープレス(１２ｂａｒまで加圧)にて析出した結晶をろ別した（ろ過性は非常に悪い）。得られた液状の反応生成物から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、パームオレインからの収率２０％で油脂組成物を得た。得られた油脂組成物のヨウ素価は６９、ＰＰＰ含量は１．５質量％、Ｐ２Ｏ含量は２０質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）の比は０．４３であった。
(Comparative Example 2)
1 kg of palm olein having an iodine value of 57 is charged into a reactor equipped with a stirrer, and nitrogen bubbling is performed at 60 ° C. under reduced pressure to reduce the residual moisture to 50 ppm or less, and then the catalyst is cooled to 20 ° C. under a nitrogen stream. 3 g of sodium methoxide was added. After stirring at 20 ° C. for 48 hours under a nitrogen stream, the precipitated crystals were filtered off with a filter press (pressurized to 12 bar) (filterability was very poor). In order to remove the catalyst from the obtained liquid reaction product, it was washed with water until neutral, and then water was removed under reduced pressure to obtain an oil and fat composition with a yield of 20% from palm olein. The obtained oil and fat composition had an iodine value of 69, a PPP content of 1.5% by mass, a P 2 O content of 20% by mass, and a POP / (POP + PPO) ratio of 0.43.
（比較例３）
撹拌機のついた反応装置にヨウ素価５７のパームオレイン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９３％で得た。得られたエステル交換油脂のＰＰＰ含量は１０質量％、Ｐ２Ｏ含量は２７質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）の比は０．３６であり、ほぼランダム化されていた。このエステル交換油脂１０ｋｇをＤｅ Ｓｍｅｔ社のＬａｂ Ｐｉｌｏｔ Ｆｒａｃｔｉｏｎａｔｉｏｎ Ｕｎｉｔ（１０ｋｇ）を用いて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３１質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．３３の液状部を収率７７％で得た(１サイクル目)。この液状部を上記記載と同様な方法でエステル交換を行い、ＰＰＰ含量８質量％、Ｐ２Ｏ含量２４質量％のエステル交換油脂を収率９４％で得た。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２４質量％の液状部を収率８１％で得た(２サイクル目)。この液状部を再度上記記載と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０．３２のエステル交換油脂を収率９４％で得た。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９０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１４質量％、ＰＯＰ／（ＰＯＰ＋ＰＰＯ）比０．４９の液状部を収率６０％で得た(３サイクル目)。パームオレインからの収率は３１％であった。実施例１に比べて収率がかなり劣った。
(Comparative Example 3)
A reactor equipped with a stirrer was charged with 10 kg of palm olein having an iodine value of 57, subjected to nitrogen bubbling at 60 ° C. under reduced pressure to reduce the residual moisture to 50 ppm or less, and then 30 g of sodium methoxide as a catalyst under a nitrogen stream. Was added. The mixture was stirred at 60 ° C. for 2 hours under a nitrogen stream to perform transesterification. After washing with water until the catalyst became neutral in order to remove the catalyst, water was removed under reduced pressure to obtain a transesterified oil and fat with a yield of 93%. The obtained transesterified oil had a PPP content of 10% by mass, a P 2 O content of 27% by mass, and a POP / (POP + PPO) ratio of 0.36, which was almost randomized. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C. using Lab Pilot Fraction Unit (10 kg) of De Smet, and then rapidly cooled to 28 ° C., followed by crystallization at 32 ° C. for 90 minutes, followed by filter press (up to 12 bar) Pressure), a liquid part having an iodine value of 62, a PPP content of 3% by mass, a P 2 O content of 31% by mass and a POP / (POP + PPO) ratio of 0.33 was obtained in a yield of 77% (first cycle). . This liquid part was transesterified in the same manner as described above to obtain a transesterified oil and fat having a PPP content of 8% by mass and a P 2 O content of 24% by mass in a yield of 94%. 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 24% by mass was obtained in a yield of 81% (second cycle). This liquid part was transesterified again in the same manner as described above, and 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 0.32 was obtained at a yield of 94%. Obtained. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C., 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 90 minutes, and 5 ° C. for 120 minutes. The liquid part having an iodine value of 75, a PPP content of 0.1% by mass, a P 2 O content of 14% by mass, and a POP / (POP + PPO) ratio of 0.49 is filtered. The yield was 60% (third cycle). The yield from palm olein was 31%. Compared with Example 1, the yield was considerably inferior.
（試験例１：油脂組成物の冷却試験）
実施例１〜３および比較例１〜３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、サラダ油規格の冷却試験（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 to 3 and Comparative Examples 1 to 3 were subjected to normal purification (deoxidation / decolorization / deodorization). About the thing which mix | blended 50 mass% of the obtained oil-fat composition and rapeseed oil, respectively, and the obtained oil-fat composition alone, the cooling test (0 degreeC, 5.5 h) of the salad oil specification was done. The results are shown in Table 1.
上記結果より、実施例１〜３および比較例３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。しかも、実施例３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および２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および２で得られた油脂組成物の液状性は充分満足できるものではなかった。 From the above results, the oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 cleared the salad oil standard cooling test (0 ° C., 5.5 h) when blended with rapeseed oil at 50 mass%. Moreover, the oil and fat composition obtained in Example 3 cleared the cooling test alone (100%). However, when the oil and fat compositions obtained in Comparative Examples 1 and 2 were mixed with rapeseed oil in an amount of 50% by mass, the cooling test could not be cleared, and the liquid properties of the oil and fat compositions obtained in Comparative Examples 1 and 2 were sufficient. It was not satisfactory.
（試験例２：油脂組成物の色度）
実施例１〜３および比較例３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。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)
The oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to normal purification (deacidification / decolorization / deodorization), and the chromaticity was measured using a Robibond colorimeter (manufactured by The Tintometer). . 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で得られた油脂組成物に比べて、比較例３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。 From the above results, the oil and fat composition obtained in Comparative Example 3 has a very high chromaticity as compared with the oil and fat compositions obtained in Examples 1 to 3, and other liquid oils based on the entire mixed oil. Even when 50% by mass was blended, it was unbearable to make a product as a salad oil.
（試験例３：油脂組成物の風味試験）
実施例１〜３および比較例３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、風味を専門のパネラー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、とした。結果を表３に示す。なお、表３中の点数は１０名の点数の平均点である。
(Test Example 3: Flavor test of oil and fat composition)
The oil / fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to ordinary purification (deoxidation / decolorization / deodorization), and the taste was evaluated by 10 professional panelists. 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. The results are shown in Table 3. In addition, the score in Table 3 is an average score of the score of 10 people.
上記結果より、実施例１〜３で得られた油脂組成物は風味が良好であり、サラダ油として充分使用できるものであった。しかし、比較例３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, the oil and fat compositions obtained in Examples 1 to 3 had good flavor and could be used satisfactorily as salad oil. However, the oil and fat composition obtained in Comparative Example 3 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１〜３および比較例３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、シリコーン２ｐｐｍを添加した。実施例１〜２および比較例３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、実施例３はそのままの油脂組成物を、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。比較対象として菜種油（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（空加熱前との比較）を比較した。結果を表４に示す。
(Test Example 4: Empty heating test of oil and fat composition)
The oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to normal purification (deoxidation / decolorization / deodorization), and then 2 ppm of silicone was added. Example 1 and 2 and Comparative Example 3 were mixed with 50% by mass of the oil / fat composition and rapeseed oil (containing 2 ppm of silicone), Example 3 was the same oil / fat composition, and a round bottom magnet having a diameter of 18 cm. 300 g was collected on a plate and heated by air at 180 ° C. for 5 hours. As a comparison object, an air heating test of rapeseed oil (containing 2 ppm of silicone) was also conducted. After returning to room temperature, the anisidine value, viscosity increase rate (comparison with before air heating) and coloring increase rate (comparison with before air heating) were compared. The results are shown in Table 4.
上記結果より、実施例１〜２および比較例３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および実施例３で得られた油脂組成物（単独）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。中でもサラダ油の冷却試験もクリアした実施例３で得られた油脂組成物（単独）は、サラダ油として優れた耐熱性を有することがわかった。比較例３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１〜２で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合したものよりも、着色上昇率がかなり劣っていた。 From the above results, the oil and fat composition obtained in Examples 1 and 2 and Comparative Example 3 and the oil and fat composition obtained in Example 3 and the oil and fat composition (single) containing 50% by mass of rapeseed oil were salad oil. The heat resistance was better than the rapeseed oil, which is the main component of Especially, it turned out that the oil-fat composition (single) obtained in Example 3 which also cleared the cooling test of salad oil has the heat resistance excellent as salad oil. What mix | blended 50 mass% of the oil-fat composition and rapeseed oil each obtained by the comparative example 3 is coloring rather than what mix | blended 50 mass% of the oil-fat composition and rapeseed oil each obtained in Examples 1-2. The rate of increase was quite inferior.
（試験例５：油脂組成物の天ぷら風味試験）
実施例１〜２および比較例３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１〜２および比較例３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、天ぷらの風味を専門のパネラー１０名が評価した。なお、比較対象として菜種油の風味試験も行った。結果を表５に示す。
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)
The oil and fat compositions obtained in Examples 1 and 2 and Comparative Example 3 were subjected to normal purification (deoxidation / decolorization / deodorization). 300 g of an oil / fat composition in which 50% by mass of rapeseed oil was blended with the oil / fat compositions of Examples 1 and 2 and Comparative Example 3 on the basis of the whole mixed oil was collected in a round bottom porcelain dish having a diameter of 18 cm. Tempura was made using the following materials at 170 ° C., and 10 professional panelists evaluated the flavor of tempura. In addition, the flavor test of rapeseed oil was also performed as a comparison object. The results are shown in Table 5.
Materials used: 2 shrimp, 2 slices of sea bream Batter composition: 50g egg, 150g water, 100g flour
上記結果より、実施例１〜２で得られた油脂組成物と菜種油とをそれぞれ５０質量％配合した油脂組成物は、風味が良く、さらに風味の維持も菜種油よりも優れていた。しかし、比較例３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、風味がかなり劣っていた。 From the above results, the oil / fat composition containing 50% by mass of the oil / fat composition obtained in Examples 1 and 2 and rapeseed oil each had good flavor, and the maintenance of the flavor was also superior to the rapeseed oil. However, the oil and fat composition containing 50% by mass of the oil and fat composition and rapeseed oil obtained in Comparative Example 3 had a considerably poor flavor.
Claims (5)
（Ｂ）エステル交換する前記工程において得られたエステル交換油脂を分別して、ＳＳＳ（Ｓは飽和脂肪酸、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）を除去する工程と、
を含むパーム油の製造方法において、前記工程（Ａ）および（Ｂ）からなる一連の工程を２回以上繰り返す、高液状性パーム油の製造方法。 (A) A step of transesterifying the palm-based fats and oils using a lipase having random transesterification ability ;
(B) The step of separating the transesterified oil and fat obtained in the step of transesterification to remove SSS (S means saturated fatty acid, SSS means triglyceride composed of three saturated fatty acids);
The manufacturing method of the high-liquid palm oil which repeats the series of processes consisting of the said process (A) and (B) twice or more in the manufacturing method of the palm oil containing this.
（ｉ）ＰＰＰ（Ｐはパルミチン酸、ＰＰＰはパルミチン酸３つで構成されるトリパルミチンを意味する）含量が０．２質量％以下、
（ｉｉ）Ｐ２Ｏ（Ｏはオレイン酸、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１６質量％以下、
（ｉｉｉ）ＰＯＰ／（ＰＯＰ＋ＰＰＯ）（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を意味し、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）比が０．３以上、０．６以下、
（ｉｖ）ヨウ素価が７０以上、
である高液状性パーム油。 A highly liquid palm oil obtained by the production method according to any one of claims 1 to 3 ,
(I) PPP (P means palmitic acid, PPP means tripalmitin composed of three palmitic acids) content is 0.2 mass% or less,
(Ii) P 2 O (O means oleic acid, P 2 O means triglyceride composed of two palmitic acids and one oleic acid) content of 16% by mass or less,
(Iii) POP / (POP + PPO) (POP means triglyceride composed of 1 and 3 positions palmitic acid, 2 position oleic acid, PPO 1 and 2 position palmitic acid, 3 position composed of oleic acid The triglyceride and the triglyceride composed of palmitic acid at positions 2 and 3 and oleic acid at position 1)
(Iv) iodine value is 70 or more,
High liquid palm oil.
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| KR101080077B1 (en) | 2009-02-26 | 2011-11-07 | 주식회사농심 | Preparation method of palm oil reduced saturated fat acid |
| JP5308309B2 (en) * | 2009-10-28 | 2013-10-09 | 株式会社Ｊ−オイルミルズ | Method for producing highly liquid palm oil for cooking |
| JP5720113B2 (en) * | 2010-04-22 | 2015-05-20 | 株式会社カネカ | Production method of solid fat |
| EP2562239A4 (en) * | 2010-04-22 | 2014-02-26 | Kaneka Corp | Liquid oil and fat, and production method therefor |
| WO2012105073A1 (en) * | 2011-01-31 | 2012-08-09 | 日清オイリオグループ株式会社 | Palm fraction soft oil and processed emulsified food product using the same |
| JP5907806B2 (en) * | 2011-05-27 | 2016-04-26 | 日清オイリオグループ株式会社 | Oil and fat for liquid cream and liquid cream using the same |
| CN111684065A (en) | 2018-02-09 | 2020-09-18 | 天野酶制品株式会社 | Random interesterified lipase |
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| JPH0466052A (en) * | 1990-07-06 | 1992-03-02 | Ajinomoto Co Inc | Salad oil |
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