JP7065581B2 - Method for producing fatty acids - Google Patents
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Description
本発明は、原料脂肪酸類を自然分別して、飽和脂肪酸又は不飽和脂肪酸を製造する方法に関する。 The present invention relates to a method for producing saturated fatty acids or unsaturated fatty acids by naturally separating raw material fatty acids.
脂肪酸類は、食品の中間原料やその他各種の工業製品の添加剤、中間原料として広く利用されている。かかる脂肪酸類は、一般に、菜種油、大豆油等の植物油や牛脂等の動物油を加水分解することにより製造される。
ところが、油脂を加水分解して得られる脂肪酸類は、そのままの脂肪酸組成では産業上の素原料として必ずしも好適なものではない。すなわち、利用の目的によって、不飽和脂肪酸と飽和脂肪酸に分別する必要がある。
Fatty acids are widely used as intermediate raw materials for foods, additives for various other industrial products, and intermediate raw materials. Such fatty acids are generally produced by hydrolyzing vegetable oils such as rapeseed oil and soybean oil and animal oils such as beef tallow.
However, the fatty acids obtained by hydrolyzing fats and oils are not always suitable as industrial raw materials with the fatty acid composition as it is. That is, it is necessary to separate unsaturated fatty acids and saturated fatty acids according to the purpose of use.
脂肪酸類の分別には、圧搾法、溶剤分別法、自然分別法（ドライ分別法）、湿潤剤分別法が知られている。なかでも、ポリグリセリン脂肪酸エステルを用いる自然分別法（例えば、特許文献１、２）は、分離効率や安全性、経済性の観点から好ましい方法である。 For the separation of fatty acids, a pressing method, a solvent separation method, a natural separation method (dry separation method), and a wetting agent separation method are known. Among them, the natural fractionation method using polyglycerin fatty acid ester (for example, Patent Documents 1 and 2) is a preferable method from the viewpoint of separation efficiency, safety and economy.
商業レベルで自然分別を行う場合、分別槽が巨大化するため迅速な冷却のために原料脂肪酸類を強撹拌することが必要となるが、撹拌条件が厳しくなると結晶の成長が妨げられて濾過性が低下し易いという問題がある。これに対して、前記特許文献１では、グリセリン重合度が高いポリグリセリン脂肪酸エステルを用いることで濾過性を向上させているものの、本発明者によれば、効率化の観点から、さらに強撹拌しながら分別を行うと濾過速度が大きく低下してしまうことが判明した。
従って、本発明の課題は、原料脂肪酸類を自然分別するにあたり、強撹拌条件下においても濾過性を向上させて、所望の脂肪酸類を効率良く製造する方法を提供することにある。
When natural sorting is performed at the commercial level, it is necessary to strongly stir the raw material fatty acids for rapid cooling because the sorting tank becomes huge, but if the stirring conditions become strict, crystal growth is hindered and filterability There is a problem that it is easy to decrease. On the other hand, in Patent Document 1, the filterability is improved by using a polyglycerin fatty acid ester having a high degree of glycerin polymerization, but according to the present inventor, the mixture is further stirred strongly from the viewpoint of efficiency. However, it was found that the filtration rate was greatly reduced when the separation was performed.
Therefore, an object of the present invention is to provide a method for efficiently producing desired fatty acids by improving the filterability even under strong stirring conditions when naturally separating the raw material fatty acids.
本発明者は、分別対象である原料脂肪酸類とポリグリセリン脂肪酸エステルの脂肪酸組成に着目して鋭意研究した結果、両者の特定の脂肪酸比率が特定の関係にある場合に、強撹拌条件下においても高い濾過速度を維持できることを見出した。 As a result of diligent research focusing on the fatty acid composition of the raw material fatty acids to be separated and the polyglycerin fatty acid ester, the present inventor has made a specific relationship between the two, even under strong stirring conditions. We have found that high filtration rates can be maintained.
すなわち、本発明は、原料脂肪酸類にポリグリセリン脂肪酸エステルを添加混合し、次いで周速１．０～３．０ｍ／ｓで撹拌しながら冷却して結晶を析出させた後、固液分離する工程を含む飽和脂肪酸又は不飽和脂肪酸の製造方法であって、
前記ポリグリセリン脂肪酸エステルの融点が２５～４０℃であり、かつ前記ポリグリセリン脂肪酸エステルを構成する脂肪酸における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｘと、前記原料脂肪酸類の脂肪酸組成における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｙとが下記式（１）の関係を満たす、製造方法を提供するものである。
０．８≦ｙ/ｘ≦１．７・・・・（１）
That is, the present invention is a step of adding and mixing polyglycerin fatty acid ester to raw material fatty acids, then cooling with stirring at a peripheral speed of 1.0 to 3.0 m / s to precipitate crystals, and then solid-liquid separation. A method for producing a saturated fatty acid or an unsaturated fatty acid containing
The melting point of the polyglycerin fatty acid ester is 25 to 40 ° C., and the content mass ratio x of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acids constituting the polyglycerin fatty acid ester, and the raw material fatty acids. The present invention provides a production method in which the content mass ratio y of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acid composition of the above satisfies the relationship of the following formula (1).
0.8 ≤ y / x ≤ 1.7 ... (1)
本発明によれば、強撹拌条件下においても濾過性に優れるため、原料脂肪酸類を効率良く自然分別でき、所望の脂肪酸類を効率良く得ることができる。 According to the present invention, since the filterability is excellent even under strong stirring conditions, the raw material fatty acids can be efficiently and naturally separated, and the desired fatty acids can be efficiently obtained.
本発明は、原料脂肪酸類にポリグリセリン脂肪酸エステルを添加混合し、次いで周速１．０～３．０ｍ／ｓで撹拌しながら冷却して結晶を析出させた後、固液分離する工程を含む飽和脂肪酸又は不飽和脂肪酸の製造方法であって、
前記ポリグリセリン脂肪酸エステルの融点が２５～４０℃であり、かつ前記ポリグリセリン脂肪酸エステルを構成する脂肪酸における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｘと、前記原料脂肪酸類の脂肪酸組成における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｙとが下記式（１）の関係を満たす、製造方法である。
０．８≦ｙ/ｘ≦１．７・・・・（１）
本明細書において、原料脂肪酸類とポリグリセリン脂肪酸エステルの脂肪酸組成は後述の〔分析方法〕（ｉ）に記載した方法に従って、また、ポリグリセリン脂肪酸エステルの融点は〔分析方法〕（ii）に記載した方法に従ってそれぞれ求めることができる。
The present invention includes a step of adding and mixing polyglycerin fatty acid ester to raw material fatty acids, then cooling with stirring at a peripheral speed of 1.0 to 3.0 m / s to precipitate crystals, and then solid-liquid separation. A method for producing saturated fatty acids or unsaturated fatty acids.
The melting point of the polyglycerin fatty acid ester is 25 to 40 ° C., and the content mass ratio x of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acids constituting the polyglycerin fatty acid ester, and the raw material fatty acids. This is a production method in which the content mass ratio y of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acid composition of the above satisfies the relationship of the following formula (1).
0.8 ≤ y / x ≤ 1.7 ... (1)
In the present specification, the fatty acid composition of the raw material fatty acid and the polyglycerin fatty acid ester is described in the method described in [Analytical Method] (i) described later, and the melting point of the polyglycerin fatty acid ester is described in [Analytical Method] (ii). Each can be obtained according to the method described above.
分別の対象となる原料脂肪酸類は、原料油脂を加水分解することにより製造される。加水分解の方法は、高温高圧分解法、酵素分解法のいずれでもよい。原料油脂は、大豆油、菜種油、シソ油、アマニ油、エゴマ油、チアシード油、サチャインチ油、藻油等の植物性油脂；魚油、ラード、牛脂、バター脂等の動物性油脂；あるいはそれらのエステル交換油、水素添加油又は分別油等の油脂類を挙げることができる。これらの油脂は、それぞれ単独で用いてもよく、２種以上混合して用いてもよい。 The raw material fatty acids to be sorted are produced by hydrolyzing the raw material fats and oils. The hydrolysis method may be either a high-temperature high-pressure decomposition method or an enzymatic decomposition method. Raw oils and fats are vegetable oils and fats such as soybean oil, rapeseed oil, perilla oil, flaxseed oil, egoma oil, chia seed oil, sachainchi oil and algae oil; animal oils and fats such as fish oil, lard, beef oil and butter oil; or their esters. Examples thereof include oils and fats such as replacement oil, hydrogenated oil, and fractionated oil. These fats and oils may be used alone or in combination of two or more.
原料脂肪酸類は、脂肪酸の他、油脂を含んでいてもよい。当該油脂（油）を構成する物質にはトリグリセリド（ＴＡＧ）、モノグリセリド（ＭＡＧ）、ジグリセリド（ＤＡＧ）が含まれる。
原料脂肪酸類中の遊離脂肪酸濃度は、本発明の効果を有効に発揮する点から、５０質量％以上であることが好ましく、更に８５質量％以上、更に９３質量％であるのがより好ましい。遊離脂肪酸濃度は、後述の〔分析方法〕（iii）及び（iv）に記載した方法に従って求めた値をいう。
The raw material fatty acids may contain fats and oils in addition to fatty acids. The substances constituting the fat (oil) include triglyceride (TAG), monoglyceride (MAG), and diglyceride (DAG).
The concentration of free fatty acids in the raw material fatty acids is preferably 50% by mass or more, more preferably 85% by mass or more, and further preferably 93% by mass, from the viewpoint of effectively exerting the effect of the present invention. The free fatty acid concentration refers to a value obtained according to the methods described in [Analytical Method] (iii) and (iv) described later.
原料脂肪酸類の脂肪酸組成中の飽和脂肪酸の含有量は、濾過性及び濾過効率の点から、５～６０質量％、更に８～５０質量％であることが好ましい。飽和脂肪酸は、炭素数１２～２４、更に炭素数１４～２２の飽和脂肪酸が好ましい。
また、原料脂肪酸類の脂肪酸組成中の炭素数１６の飽和脂肪酸及び炭素数１８の飽和脂肪酸の含有量の和は、ポリグリセリン脂肪酸エステルとの相互作用の点から、５～６０質量％、更に８～５０質量％であることが好ましい。
The content of saturated fatty acids in the fatty acid composition of the raw material fatty acids is preferably 5 to 60% by mass, more preferably 8 to 50% by mass, from the viewpoint of filterability and filtration efficiency. The saturated fatty acid is preferably a saturated fatty acid having 12 to 24 carbon atoms and further preferably 14 to 22 carbon atoms.
Further, the sum of the contents of the saturated fatty acid having 16 carbon atoms and the saturated fatty acid having 18 carbon atoms in the fatty acid composition of the raw material fatty acids is 5 to 60% by mass, further 8 from the viewpoint of interaction with the polyglycerin fatty acid ester. It is preferably ~ 50% by mass.
本発明で用いるポリグリセリン脂肪酸エステルとは、ポリグリセリンと脂肪酸とをエステル化させて得られるものである。
ポリグリセリンとエステル化させる脂肪酸は、炭素数１０～２２、更に炭素数１２～１８の飽和又は不飽和の脂肪酸から構成されることが好ましい。当該脂肪酸は、単一脂肪酸のみで構成されてもよいが、混合脂肪酸で構成されていることが、結晶が大きく成長して、濾過性が向上する点から好ましい。
The polyglycerin fatty acid ester used in the present invention is obtained by esterifying polyglycerin and a fatty acid.
The fatty acid esterified with polyglycerin is preferably composed of saturated or unsaturated fatty acids having 10 to 22 carbon atoms and 12 to 18 carbon atoms. The fatty acid may be composed of only a single fatty acid, but it is preferable that the fatty acid is composed of a mixed fatty acid from the viewpoint of large growth of crystals and improvement of filterability.
ポリグリセリン脂肪酸エステルの融点は、２５～４０℃であるが、原料脂肪酸類の結晶化及び成長を促進する観点から、２７～３８℃であることが好ましい。 The melting point of the polyglycerin fatty acid ester is 25 to 40 ° C., but it is preferably 27 to 38 ° C. from the viewpoint of promoting the crystallization and growth of the raw material fatty acids.
ポリグリセリン脂肪酸エステルのグリセリンの平均重合度は、特に限定されないが、濾過容易な結晶を得る点から、１５～５０であることが好ましく、更に２０～４５、更に２５～４０であることがより好ましい。「グリセリンの平均重合度」とは、ポリグリセリン脂肪酸エステルのポリグリセリン部分の重合度をＧＰＣにより測定した値をいう。 The average degree of polymerization of glycerin in the polyglycerin fatty acid ester is not particularly limited, but is preferably 15 to 50, more preferably 20 to 45, and further preferably 25 to 40 from the viewpoint of obtaining crystals that can be easily filtered. .. The "average degree of polymerization of glycerin" means a value obtained by measuring the degree of polymerization of the polyglycerin portion of the polyglycerin fatty acid ester by GPC.
本発明では、ポリグリセリン脂肪酸エステルを構成する脂肪酸における炭素数１８の飽和脂肪酸（Ｓ）に対する炭素数１６の飽和脂肪酸（Ｐ）の含有質量比［（Ｐ）／（Ｓ）］、すなわちｘと、原料脂肪酸類の脂肪酸組成における炭素数１８の飽和脂肪酸（Ｓ）に対する炭素数１６の飽和脂肪酸（Ｐ）の含有質量比［（Ｐ）／（Ｓ）］、すなわちｙとが下記式（１）の関係を満たす。
０．８≦ｙ/ｘ≦１．７・・・・（１）
上記ｘに対するｙの値［ｙ／ｘ］が、斯かる範囲内であると、前記特許文献１に比べてさらに強撹拌しながら分別を行っても高い濾過速度を維持できる。
上記ｘに対するｙの値［ｙ／ｘ］は、原料脂肪酸類とポリグリセリン脂肪酸エステルの相互作用の点から、０．９以上１．７以下、更に０．９以上１．６以下であることが好ましい。
In the present invention, the content mass ratio of the saturated fatty acid (P) having 16 carbon atoms to the saturated fatty acid (S) having 18 carbon atoms in the fatty acids constituting the polyglycerin fatty acid ester [(P) / (S)], that is, x and The content mass ratio [(P) / (S)] of the saturated fatty acid (P) having 16 carbon atoms to the saturated fatty acid (S) having 18 carbon atoms in the fatty acid composition of the raw material fatty acids, that is, y is the following formula (1). Meet the relationship.
0.8 ≤ y / x ≤ 1.7 ... (1)
When the value [y / x] of y with respect to x is within such a range, a high filtration rate can be maintained even if fractionation is performed with stronger stirring as compared with Patent Document 1.
The value [y / x] of y with respect to x is 0.9 or more and 1.7 or less, and further 0.9 or more and 1.6 or less, from the viewpoint of the interaction between the raw material fatty acid and the polyglycerin fatty acid ester. preferable.
ポリグリセリン脂肪酸エステルを構成する脂肪酸中の飽和脂肪酸の含有量は、原料脂肪酸類との相互作用及び融点の点から、２０質量％以上であることが好ましく、更に３０～１００質量％、更に４０～９５質量％、更に５０～９０質量％であることがより好ましい。飽和脂肪酸は、炭素数１２～２２、更に炭素数１２～１８の飽和脂肪酸が好ましい。
また、ポリグリセリン脂肪酸エステルを構成する脂肪酸中の炭素数１６の飽和脂肪酸及び炭素数１８の飽和脂肪酸の含有量の和は、同様の点から、２０質量％以上であることが好ましく、更に２０～８０質量％、更には３０～６０質量％であることが好ましい。
The content of saturated fatty acids in the fatty acids constituting the polyglycerin fatty acid ester is preferably 20% by mass or more, more preferably 30 to 100% by mass, and further 40 to 40% in terms of interaction with raw material fatty acids and melting point. It is more preferably 95% by mass, more preferably 50 to 90% by mass. The saturated fatty acid is preferably a saturated fatty acid having 12 to 22 carbon atoms and further preferably 12 to 18 carbon atoms.
Further, the sum of the contents of the saturated fatty acid having 16 carbon atoms and the saturated fatty acid having 18 carbon atoms in the fatty acids constituting the polyglycerin fatty acid ester is preferably 20% by mass or more, more preferably 20 to 20% by mass, from the same point of view. It is preferably 80% by mass, more preferably 30 to 60% by mass.
ポリグリセリン脂肪酸エステルを構成する脂肪酸中の不飽和脂肪酸の含有量は、原料脂肪酸類との相互作用及び、融点の点から、８０質量％以下であることが好ましく、更に０～７０質量％、更に５～６０質量％、更に１０～５０質量％であることがより好ましい。 The content of unsaturated fatty acids in the fatty acids constituting the polyglycerin fatty acid ester is preferably 80% by mass or less, more preferably 0 to 70% by mass, and further, from the viewpoint of interaction with raw material fatty acids and the melting point. It is more preferably 5 to 60% by mass, more preferably 10 to 50% by mass.
ポリグリセリン脂肪酸エステルは２種以上を併用してもよい。
ポリグリセリン脂肪酸エステルの添加量は、濾過性の点から、原料脂肪酸類に対して０．００１～５質量％、更に０．０５～１質量％であることが好ましい。
ポリグリセリン脂肪酸エステルの添加混合の時期は、結晶析出開始前、すなわち冷却開始前である。ポリグリセリン脂肪酸エステルは、原料脂肪酸類に完全に溶解できるように、ポリグリセリン脂肪酸エステルの融点より高い温度で混合溶解することが好ましい。
Two or more kinds of polyglycerin fatty acid esters may be used in combination.
The amount of the polyglycerin fatty acid ester added is preferably 0.001 to 5% by mass, more preferably 0.05 to 1% by mass, based on the raw material fatty acids, from the viewpoint of filterability.
The timing of addition and mixing of the polyglycerin fatty acid ester is before the start of crystal precipitation, that is, before the start of cooling. The polyglycerin fatty acid ester is preferably mixed and dissolved at a temperature higher than the melting point of the polyglycerin fatty acid ester so that it can be completely dissolved in the raw material fatty acids.
次いで、周速１．０～３．０ｍ／ｓで撹拌しながら冷却する。
撹拌の周速は１．０～３．０ｍ／ｓであるが、商業での巨大な設備での混合性の点から、更に１．０５ｍ／ｓ以上が好ましく、また、結晶の破砕抑制及び、濾過性の点から、更に２．８ｍ／ｓ以下が好ましい。
撹拌翼は、いずれの形状でもかまわないが、特に結晶の混合を良好にするため、パドル翼、タービン翼、プロペラ翼、アンカー翼、大翼径パドル翼、マックスブレンド翼であることが好ましい。
Then, the mixture is cooled with stirring at a peripheral speed of 1.0 to 3.0 m / s.
The peripheral speed of stirring is 1.0 to 3.0 m / s, but it is more preferably 1.05 m / s or more from the viewpoint of mixing in a huge commercial facility, and further, suppression of crystal crushing and suppression of crystal crushing and From the viewpoint of filterability, it is more preferably 2.8 m / s or less.
The stirring blade may have any shape, but is preferably a paddle blade, a turbine blade, a propeller blade, an anchor blade, a large blade diameter paddle blade, or a max blend blade in order to improve crystal mixing.
原料脂肪酸類の冷却温度は、飽和脂肪酸が結晶化して析出する温度であればよいが、分離効率の点から、－１０～１０℃の範囲内、更に－８～８℃であることが好ましい。 The cooling temperature of the raw material fatty acids may be any temperature as long as the saturated fatty acids crystallize and precipitate, but from the viewpoint of separation efficiency, it is preferably in the range of −10 to 10 ° C., and more preferably −8 to 8 ° C.
ポリグリセリン脂肪酸エステルの添加混合時の温度から冷却温度に至るまでに要した時間から算出される平均冷却速度は、結晶成長及び効率の点から、１～１０℃／ｍｉｎ、更に２～９℃であることが好ましい。冷却速度は、冷却操作中に変化させてもよい。冷却速度の変化は１回～４回が好ましい。また、その変化のさせ方は、効率及び結晶が大きく成長して、濾過性が向上する点から、結晶が析出しない温度までは冷却速度を大きくし、結晶が析出する温度付近で、冷却速度を低下させるのが好ましい。 The average cooling rate calculated from the time required from the temperature at the time of adding and mixing the polyglycerin fatty acid ester to the cooling temperature is 1 to 10 ° C./min, and further 2 to 9 ° C. from the viewpoint of crystal growth and efficiency. It is preferable to have. The cooling rate may be varied during the cooling operation. The change in the cooling rate is preferably 1 to 4 times. In addition, the method of changing the change is to increase the cooling rate until the temperature at which the crystals do not precipitate, and to increase the cooling rate near the temperature at which the crystals precipitate, from the point that the efficiency and the crystal grow greatly and the filterability is improved. It is preferable to reduce it.
冷却時間は、原料脂肪酸類の量、冷却能力等によって異なり、適宜調整すればよい。一般的には、冷却時間は１～３０時間である。 The cooling time varies depending on the amount of raw material fatty acids, cooling capacity, etc., and may be appropriately adjusted. Generally, the cooling time is 1 to 30 hours.
冷却後、析出した結晶と液体部とを分離する。
固液分離の方法は、特に限定されず、例えば、濾過、遠心分離、沈降分離等が挙げられる。当該分離により、固体部（結晶部）として飽和脂肪酸が、液体部として不飽和脂肪酸がそれぞれ得られる。
After cooling, the precipitated crystals and the liquid part are separated.
The method of solid-liquid separation is not particularly limited, and examples thereof include filtration, centrifugation, and sedimentation separation. By the separation, a saturated fatty acid is obtained as a solid part (crystal part), and an unsaturated fatty acid is obtained as a liquid part.
〔分析方法〕
（ｉ）脂肪酸組成の測定
日本油化学会編「基準油脂分析試験法２００３年版」中の「メチルエステル化法（三フッ化ホウ素メタノール法）（２．４．１．２－１９９６）」に従って脂肪酸メチルエステルを調製し、得られたサンプルを、ガスクロマトグラフィーに供して、構成脂肪酸の分析を行った。
[Analysis method]
(I) Measurement of fatty acid composition Fatty acids according to "Methyl esterification method (boron trifluoride methanol method) (2.4.1.2-1996)" in "Standard Fatty Acid Analysis Test Method 2003" edited by Japan Oil Chemists' Society. Methyl esters were prepared and the obtained samples were subjected to gas chromatography for analysis of constituent fatty acids.
（ii）融点の測定
基準油脂分析試験法（２．２．４．１－１９９６）により測定した。
(Ii) Measurement of melting point Measurement was performed by the standard oil and fat analysis test method (2.2.4.1-1996).
（iii）酸価の測定
日本油化学会編「基準油脂分析試験法２００３年版」中の「酸価（２．３．１－１９９６）」に従って測定した。
(Iii) Measurement of acid value The acid value was measured according to "Acid value (23.1-1996)" in "Standard Oil and Fat Analysis Test Method 2003" edited by Japan Oil Chemists' Society.
（iv）遊離脂肪酸濃度の測定
遊離脂肪酸濃度は、原料脂肪酸類の酸価及び脂肪酸組成を測定し、次式（２）で求めた。アマニ油の脂肪酸平均分子量は２８０とした。
脂肪酸濃度（質量％）＝ａ×ｂ／５６．１１／１０ （２）
（ａ＝酸価［ｍｇＫＯＨ／ｇ］、ｂ＝脂肪酸組成から求めた平均分子量）
(Iv) Measurement of free fatty acid concentration The free fatty acid concentration was determined by the following formula (2) by measuring the acid value and fatty acid composition of the raw material fatty acids. The average fatty acid molecular weight of flaxseed oil was 280.
Fatty acid concentration (mass%) = a × b / 56.11 / 10 (2)
(A = acid value [mgKOH / g], b = average molecular weight obtained from fatty acid composition)
〔原料脂肪酸類の調製〕
アマニ油を加水分解酵素（リパーゼ）により加水分解し、表１に示す原料脂肪酸類をそれぞれ調製した。各原料脂肪酸類の脂肪酸組成、飽和脂肪酸比率、［（Ｐ）／（Ｓ）］比率、及び遊離脂肪酸濃度を表１に示す。
[Preparation of raw material fatty acids]
Linseed oil was hydrolyzed with a hydrolase (lipase) to prepare the raw material fatty acids shown in Table 1. Table 1 shows the fatty acid composition, saturated fatty acid ratio, [(P) / (S)] ratio, and free fatty acid concentration of each raw material fatty acid.
〔ポリグリセリン脂肪酸エステル〕
以下の例に使用したポリグリセリン脂肪酸エステルの分析値を表２に示す。ＰＧＥ１～３のグリセリンの平均重合度は３８であった。
[Polyglycerin fatty acid ester]
Table 2 shows the analytical values of the polyglycerin fatty acid ester used in the following examples. The average degree of polymerization of glycerin of PGE1 to 3 was 38.
＜実施例１＞
表３に示した晶析槽（Ｎｏ．１）を用いて、原料脂肪酸類（原料１）２ｋｇにＰＧＥ２を３ｇ加え、７０℃で均一に溶解した。次いで、撹拌翼周速１．０５ｍ/ｓ（撹拌速度２００ｒ／ｍｉｎ）で撹拌しつつ、１６℃まで６℃/ｈｒで、１６℃から６℃まで２．２５℃/ｈｒで冷却し、５時間撹拌を保持した。次いで、ナイロン製濾布（濾過面積３９ｃｍ2、ＮＹ１２６０ＮＬＫ、三菱化工機社製）を用い０．０３ＭＰａで加圧濾過して、濾液である液体部（不飽和脂肪酸）と固体部（飽和脂肪酸）に分別した。濾液量が４００ｍＬとなるのに必要な時間を測定し、濾過時間(分)とした。また、液体部中の炭素数１２～２２の飽和脂肪酸濃度を求めた。
<Example 1>
Using the crystallization tank (No. 1) shown in Table 3, 3 g of PGE2 was added to 2 kg of raw material fatty acids (raw material 1), and the mixture was uniformly dissolved at 70 ° C. Then, while stirring at a stirring blade peripheral speed of 1.05 m / s (stirring speed of 200 r / min), the mixture was cooled to 16 ° C. at 6 ° C./hr and from 16 ° C. to 6 ° C. at 2.25 ° C./hr for 5 hours. Stirring was maintained. Next, using a nylon filter cloth (filtration area 39 cm 2 , NY1260NLK, manufactured by Mitsubishi Kakoki Co., Ltd.), pressure filtration was performed at 0.03 MPa to form a liquid part (unsaturated fatty acid) and a solid part (saturated fatty acid) as a filtrate. Sorted. The time required for the amount of the filtrate to reach 400 mL was measured and used as the filtration time (minutes). In addition, the concentration of saturated fatty acids having 12 to 22 carbon atoms in the liquid part was determined.
＜比較例１＞
添加するポリグリセリン脂肪酸エステルをＰＧＥ１に変更した以外は、実施例１に記載した方法に準じ、液体部（不飽和脂肪酸）と固体部（飽和脂肪酸）に分別した。濾液量が４００ｍＬとなるのに必要な時間を測定し、また、液体部中の炭素数１２～２２の飽和脂肪酸濃度を求めた。
<Comparative Example 1>
The polyglycerin fatty acid ester to be added was separated into a liquid part (unsaturated fatty acid) and a solid part (saturated fatty acid) according to the method described in Example 1 except that the polyglycerin fatty acid ester was changed to PGE1. The time required for the amount of the filtrate to reach 400 mL was measured, and the concentration of saturated fatty acids having 12 to 22 carbon atoms in the liquid part was determined.
＜参考例１＞
添加するポリグリセリン脂肪酸エステルをＰＧＥ１に変更し、撹拌翼周速を０．７９ｍ/ｓ（撹拌速度１５０ｒ/ｍｉｎ）に変更した以外は、実施例１に記載した方法に準じ、液体部（不飽和脂肪酸）と固体部（飽和脂肪酸）に分別した。濾液量が４００ｍＬとなるのに必要な時間を測定し、また、液体部中の炭素数１２～２２の飽和脂肪酸濃度を求めた。
<Reference example 1>
The liquid part (unsaturated) was according to the method described in Example 1 except that the polyglycerin fatty acid ester to be added was changed to PGE1 and the peripheral speed of the stirring blade was changed to 0.79 m / s (stirring speed 150 r / min). It was separated into a fatty acid) and a solid part (saturated fatty acid). The time required for the amount of the filtrate to reach 400 mL was measured, and the concentration of saturated fatty acids having 12 to 22 carbon atoms in the liquid part was determined.
＜実施例２＞
表３に示した晶析槽（Ｎｏ．２）を用いて、原料脂肪酸類（原料２）２８００ｋｇにＰＧＥ２を４．２ｋｇ加え、７０℃で均一に溶解した。次いで、撹拌翼周速２．２５ｍ/ｓ（撹拌速度２５ｒ／ｍｉｎ）で撹拌しつつ、１６℃まで８℃/ｈｒで、１６℃から６℃まで３℃/ｈｒで冷却し、５時間撹拌を保持した。次いで、実施例１に記載した方法に準じて濾過操作を行い、液体部（不飽和脂肪酸）と固体部（飽和脂肪酸）に分別した。濾液量が４００ｍＬとなるのに必要な時間を測定し、また、液体部中の炭素数１２～２２の飽和脂肪酸濃度を求めた。
<Example 2>
Using the crystallization tank (No. 2) shown in Table 3, 4.2 kg of PGE2 was added to 2800 kg of raw material fatty acids (raw material 2), and the mixture was uniformly dissolved at 70 ° C. Next, while stirring at a stirring blade peripheral speed of 2.25 m / s (stirring speed 25 r / min), the mixture was cooled to 16 ° C. at 8 ° C./hr and from 16 ° C. to 6 ° C. at 3 ° C./hr, and stirred for 5 hours. Retained. Then, a filtration operation was carried out according to the method described in Example 1 to separate the liquid part (unsaturated fatty acid) and the solid part (saturated fatty acid). The time required for the amount of the filtrate to reach 400 mL was measured, and the concentration of saturated fatty acids having 12 to 22 carbon atoms in the liquid part was determined.
＜実施例３＞
表３に示した晶析槽（Ｎｏ．３）を用いて、原料脂肪酸類（原料３）８９００ｋｇにＰＧＥ３を１３．３ｋｇ加え、７０℃で均一に溶解した。次いで、撹拌翼周速２．６４ｍ/ｓ（撹拌速度２８ｒ／ｍｉｎ）で撹拌しつつ、１１℃まで６℃/ｈｒで、１１℃から５℃まで２℃／ｈｒで、５℃から－３℃まで３℃／ｈｒで冷却し、４時間撹拌を保持した。次いで、実施例１に記載した方法に準じて濾過操作を行い、液体部（不飽和脂肪酸）と固体部（飽和脂肪酸）に分別した。濾液量が４００ｍＬとなるのに必要な時間を測定し、また、液体部中の炭素数１２～２２の飽和脂肪酸濃度を求めた。
結果を表４に示す。
<Example 3>
Using the crystallization tank (No. 3) shown in Table 3, 13.3 kg of PGE3 was added to 8900 kg of raw material fatty acids (raw material 3), and the mixture was uniformly dissolved at 70 ° C. Then, while stirring at a stirring blade peripheral speed of 2.64 m / s (stirring speed 28r / min), the temperature is 6 ° C / hr up to 11 ° C, 2 ° C / hr from 11 ° C to 5 ° C, and 5 ° C to -3 ° C. The mixture was cooled to 3 ° C./hr and kept stirring for 4 hours. Next, a filtration operation was performed according to the method described in Example 1, and the liquid portion (unsaturated fatty acid) and the solid portion (saturated fatty acid) were separated. The time required for the amount of the filtrate to reach 400 mL was measured, and the concentration of saturated fatty acids having 12 to 22 carbon atoms in the liquid part was determined.
The results are shown in Table 4.
表４の比較例１と参考例１の対比より明らかなように、撹拌条件が厳しくなると濾過性が低下するところ、実施例１～３のように［ｙ／ｘ］値が所定の範囲にあると強撹拌条件下でも濾過性に優れ、原料脂肪酸類を効率良く自然分別できることが確認された。 As is clear from the comparison between Comparative Example 1 and Reference Example 1 in Table 4, the filterability deteriorates when the stirring conditions become strict, but the [y / x] value is in a predetermined range as in Examples 1 to 3. It was confirmed that the raw material fatty acids can be efficiently and naturally separated with excellent filterability even under strong stirring conditions.
Claims (4)
前記ポリグリセリン脂肪酸エステルの融点が２５～４０℃であり、かつ前記ポリグリセリン脂肪酸エステルを構成する脂肪酸における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｘと、前記原料脂肪酸類の脂肪酸組成における炭素数１８の飽和脂肪酸に対する炭素数１６の飽和脂肪酸の含有質量比ｙとが下記式（１）の関係を満たす、製造方法。
０．８≦ｙ/ｘ≦１．７・・・・（１） Using a crystallization tank with an inner diameter of 0.13 m or more, polyglycerin fatty acid ester is added and mixed with the raw material fatty acids, and then cooled with an anchor blade at a peripheral speed of 1.0 to 3.0 m / s to cool the crystals. A method for producing a saturated fatty acid or an unsaturated fatty acid, which comprises a step of solid-liquid separation after precipitation.
The melting point of the polyglycerin fatty acid ester is 25 to 40 ° C., and the content mass ratio x of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acids constituting the polyglycerin fatty acid ester, and the raw material fatty acids. A production method, wherein the content mass ratio y of the saturated fatty acid having 16 carbon atoms to the saturated fatty acid having 18 carbon atoms in the fatty acid composition of the above satisfies the relationship of the following formula (1).
0.8 ≤ y / x ≤ 1.7 ... (1)
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| JP2004067998A (en) | 2002-06-14 | 2004-03-04 | Kao Corp | Method for producing fatty acid |
| JP2005146098A (en) | 2003-11-14 | 2005-06-09 | Kao Corp | Method for producing fatty acid |
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| JP2004043703A (en) | 2002-07-15 | 2004-02-12 | Kao Corp | Manufacturing method of fatty acid |
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