JPH06234695A - Method for purifying fatty acid - Google Patents
Method for purifying fatty acidInfo
- Publication number
- JPH06234695A JPH06234695A JP2148493A JP2148493A JPH06234695A JP H06234695 A JPH06234695 A JP H06234695A JP 2148493 A JP2148493 A JP 2148493A JP 2148493 A JP2148493 A JP 2148493A JP H06234695 A JPH06234695 A JP H06234695A
- Authority
- JP
- Japan
- Prior art keywords
- pressure
- mixture
- acid
- stearic acid
- fatty acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、分子間化合物を形成す
る脂肪酸の混合物から、圧力晶析法を利用して特定の脂
肪酸を効率良く単離精製する方法に関するものである。
そしてこの方法は、たとえばステアリン酸とパルミチン
酸の混合物からステアリン酸を単離精製する方法あるい
はステアリン酸とマルガリン酸の混合物からステアリン
酸を単離精製する方法などとして有効に活用できるが、
本明細書では脂肪酸混合物からステアリン酸を単離精製
する場合を代表的に取り上げて説明する。TECHNICAL FIELD The present invention relates to a method for efficiently isolating and purifying a specific fatty acid from a mixture of fatty acids forming an intermolecular compound by utilizing a pressure crystallization method.
And this method can be effectively utilized, for example, as a method for isolating and purifying stearic acid from a mixture of stearic acid and palmitic acid or a method for isolating and purifying stearic acid from a mixture of stearic acid and margaric acid.
In the present specification, a case where stearic acid is isolated and purified from a fatty acid mixture will be representatively described.
【0002】[0002]
【従来の技術】ステアリン酸等の脂肪酸は、医薬、バイ
オケミカル、香料、化粧品等の分野における新たな用途
開発のため高純度化のニーズが最近急速に高まってい
る。ステアリン酸等の脂肪酸の精製法としては、温度に
よる溶解度の変化を利用した冷却晶析法、吸着法、クロ
マト法等が利用されている。このうち冷却晶析法は大量
処理が可能で精製コストが安いという利点を有している
反面、90%程以上の高純度物が得られ難く、純度の点
で需要者の要求を満たすことができない。一方、吸着法
やクロマト法は98〜99%以上といった高純度化が容
易に達成できる反面、処理能力の点で大量処理が困難で
あり、処理コストが非常に割高になる。この様なところ
から、純度、処理能力、コストのすべてにおいて要望に
かなう様な精製技術の開発が待たれている。2. Description of the Related Art Needs for high purification of fatty acids such as stearic acid have been rapidly increasing recently for the development of new applications in the fields of medicine, biochemicals, fragrances, cosmetics and the like. As a refining method of fatty acids such as stearic acid, a cooling crystallization method, an adsorption method, a chromatography method and the like, which utilize a change in solubility with temperature, are used. Among them, the cooling crystallization method has an advantage that a large amount of treatment is possible and the refining cost is low, but on the other hand, it is difficult to obtain a high-purity substance of about 90% or more, and it is possible to satisfy the demand of consumers in terms of purity. Can not. On the other hand, the adsorption method and the chromatographic method can easily achieve high purity of 98 to 99% or more, but on the other hand, in terms of processing capacity, large-scale processing is difficult and the processing cost becomes very expensive. From such a point, the development of refining technology that meets the requirements in terms of purity, processing capacity, and cost is awaited.
【0003】[0003]
【発明が解決しようとする課題】本発明は上記の様な事
情に着目してなされたものであって、その目的は、2種
以上の脂肪酸を含む脂肪酸混合物から、特定の脂肪酸を
高純度で効率良く単離精製することのできる技術を確立
しようとするものである。The present invention has been made in view of the above circumstances, and its object is to obtain a specific fatty acid with high purity from a fatty acid mixture containing two or more fatty acids. It is intended to establish a technique that enables efficient isolation and purification.
【0004】[0004]
【課題を解決するための手段】上記課題を解決すること
のできた本発明に係る脂肪酸の精製法とは、分子間化合
物を形成する脂肪酸の混合物から特定の脂肪酸を単離精
製する方法であって、該脂肪酸混合物を分子間化合物が
生成する圧力未満の圧力領域まで加圧して特定脂肪酸の
結晶を生成せしめ、次いで降圧することにより該結晶の
一部を種結晶として残して残部を溶融させた後、該種結
晶を加圧下に成長させてから母液と分離するところに要
旨を有するものであり、この方法はたとえばステアリン
酸とパルミチン酸の混合物からステアリン酸および/ま
たはパルミチン酸を単離精製するあるいは、同様にステ
アリン酸とマルガリン酸の混合物からステアリン酸およ
び/またはパルミチン酸を単離精製する方法として有効
に活用できる。The method for purifying a fatty acid according to the present invention, which has been able to solve the above-mentioned problems, is a method for isolating and purifying a specific fatty acid from a mixture of fatty acids forming an intermolecular compound. After the fatty acid mixture is pressurized to a pressure region below the pressure at which the intermolecular compound is generated to form crystals of the specific fatty acid, and then the pressure is reduced to leave a part of the crystals as seed crystals and melt the rest. The method is characterized in that the seed crystal is grown under pressure and then separated from the mother liquor, and this method comprises, for example, isolating and purifying stearic acid and / or palmitic acid from a mixture of stearic acid and palmitic acid. Similarly, it can be effectively utilized as a method for isolating and purifying stearic acid and / or palmitic acid from a mixture of stearic acid and margaric acid.
【0005】[0005]
【作用】本発明者らは、かねてより圧力晶析法を利用し
た分離精製法について研究を進めており、その一環とし
て、該圧力晶析法を利用した特定脂肪酸の単離精製の可
能性について追求してきた。The present inventors have been conducting research on a separation and purification method utilizing the pressure crystallization method for some time, and as a part thereof, the possibility of isolating and purifying a specific fatty acid using the pressure crystallization method. I have been pursuing.
【0006】ところが脂肪酸類を晶析法により精製しよ
うとした場合、脂肪酸類は晶出する結晶が非常に微細で
あって母液との完全分離がむずかしく、更には晶析条件
下で分子間化合物や固溶体を生成したり結晶多形が出現
するといった傾向があり、これらが高純度精製を達成す
るための大きな障害になっていることが明らかになっ
た。However, when the fatty acids are to be purified by a crystallization method, the fatty acids have extremely fine crystals that are difficult to completely separate from the mother liquor. It was found that there was a tendency to form a solid solution and appearance of crystalline polymorphs, which became a major obstacle to achieving high-purity purification.
【0007】上記傾向の中でも、晶析工程で2種の脂肪
酸が分子間化合物となって晶出すると、特定脂肪酸とし
ての単離精製は不可能になる。たとえば図1は、ステア
リン酸とパルミチン酸の混合物を345K(72℃)で
加圧した場合の圧力をパラメータとする融解曲線を示し
たものであり、曲線の下方側は液相、上方側は固相を表
わしている。この図からも明らかである様に曲線A,
B,Cで示される融解曲線にはステアリン酸/パルミチ
ン酸含有比率が30/70と50/50の2点にピーク
(共晶点)が現われ、同含有比率が30/70〜50/
50の領域で分子間化合物が生成することを確認でき
る。こうした傾向は、図2に示す常圧下のステアリン酸
/パルミチン酸混合物の融解曲線の傾向とも合致してい
る。[0007] Among the above tendencies, if two kinds of fatty acids are crystallized as intermolecular compounds in the crystallization step, isolation and purification as specific fatty acids becomes impossible. For example, FIG. 1 shows a melting curve having a pressure when a mixture of stearic acid and palmitic acid is pressurized at 345 K (72 ° C.) as a parameter, and the lower side of the curve is the liquid phase and the upper side is the solid phase. Represents a phase. As is clear from this figure, curve A,
In the melting curves shown by B and C, peaks (eutectic points) appear at two points of the stearic acid / palmitic acid content ratios of 30/70 and 50/50, and the same content ratio is 30/70 to 50 /.
It can be confirmed that an intermolecular compound is generated in the region of 50. This tendency is in agreement with the tendency of the melting curve of the stearic acid / palmitic acid mixture under normal pressure shown in FIG.
【0008】従って、たとえばこの分子間化合物を生成
する含有比率(たとえば図1のX点)の脂肪酸混合物
(液状物)を昇圧していくと、圧力が曲線Bに達した時
点で結晶が析出しはじめるが、曲線Bは分子間化合物生
成領域であるため晶出物はすべてが分子間化合物とな
り、特定脂肪酸(たとえばステアリン酸)を単離するこ
とはできない。Therefore, for example, when the pressure of the fatty acid mixture (liquid substance) having the content ratio (for example, point X in FIG. 1) for forming the intermolecular compound is increased, crystals are precipitated when the pressure reaches the curve B. First, since the curve B is the intermolecular compound generation region, all the crystallized substances are intermolecular compounds, and the specific fatty acid (for example, stearic acid) cannot be isolated.
【0009】一方、分子間化合物生成領域を外れる混合
比率(たとえば図1のY点)の脂肪酸混合物(液状物)
を昇圧していくと、圧力が曲線Cに達した時点で析出し
はじめる。このときに生成する結晶はステアリン酸のみ
であるが、更に昇圧していくと、ステアリン酸が晶出し
た分だけ母液中のステアリン酸濃度は曲線Cに沿って低
減していき、晶析圧力がE1 点に達した時点で分子間化
合物が晶出しはじめる。従って晶出物は分子間化合物の
混在したものとなり、ステアリン酸の純度を十分に高め
ることができない。On the other hand, a fatty acid mixture (liquid substance) having a mixing ratio (for example, point Y in FIG. 1) outside the intermolecular compound formation region.
As the pressure is increased, when the pressure reaches the curve C, precipitation starts to occur. The crystals produced at this time were only stearic acid, but when the pressure was further increased, the stearic acid concentration in the mother liquor decreased along the curve C as much as stearic acid crystallized, and the crystallization pressure was increased. When the E 1 point is reached, intermolecular compounds start to crystallize. Therefore, the crystallized substance is a mixture of intermolecular compounds, and the purity of stearic acid cannot be sufficiently increased.
【0010】ところが、本発明者らが操作温度を種々変
えて圧力晶析実験を進めるうち次の様な事実が確認され
た。即ち、ステアリン酸/パルミチン酸混合物の圧力融
解曲線における分子間化合物生成領域は、操作温度によ
って変動する傾向が見られ、たとえば図3に示す如く3
45(72℃)では、図1にも示した様にステアリン酸
/パルミチン酸比が30/70〜50/50の間で分子
間化合物生成領域となるが、操作温度を高めるにつれて
該生成領域は徐々に狭くなり、操作温度が85℃以上に
なると分子間化合物生成領域(曲線B)が殆ど消失し、
ステアリン酸/パルミチン酸比が約40/60のところ
で唯1点の共晶点(圧力:約1500kgf/cm2 )を示す
様になることが確認された。However, the present inventors confirmed the following facts while advancing the pressure crystallization experiment by changing the operating temperature variously. That is, the intermolecular compound formation region in the pressure melting curve of the stearic acid / palmitic acid mixture tends to vary depending on the operating temperature. For example, as shown in FIG.
At 45 (72 ° C.), as shown in FIG. 1, the stearic acid / palmitic acid ratio is in the intermolecular compound formation region between 30/70 and 50/50, but as the operating temperature is increased, the formation region becomes When the operating temperature becomes 85 ° C or higher, the intermolecular compound formation region (curve B) almost disappears,
It was confirmed that when the stearic acid / palmitic acid ratio was about 40/60, only one eutectic point (pressure: about 1500 kgf / cm 2 ) was exhibited.
【0011】従ってこうした現象を活用し、分子間化合
物を生成しない温度条件を採用し、共晶点を外れる圧力
で昇圧を行なえば、ステアリン酸および/またはパルミ
チン酸をうまく単離精製し得るものと考えられる。事
実、ステアリン酸/パルミチン酸よりなる脂肪酸混合物
を85℃以上の温度条件下で圧力晶析すると、分子間化
合物の生成が見られなくなり、従って共晶を外れる原料
組成および圧力条件を採用することによってステアリン
酸(もしくはパルミチン酸)を高純度に単離精製するこ
とが可能となる。Therefore, if such a phenomenon is utilized, temperature conditions that do not form an intermolecular compound are adopted, and pressure is raised at a pressure outside the eutectic point, stearic acid and / or palmitic acid can be isolated and purified successfully. Conceivable. In fact, when a fatty acid mixture consisting of stearic acid / palmitic acid is pressure-crystallized under a temperature condition of 85 ° C. or higher, the formation of intermolecular compound is not observed, and therefore, by adopting a raw material composition and a pressure condition that deviate from the eutectic crystal, It becomes possible to isolate and purify stearic acid (or palmitic acid) with high purity.
【0012】但し、分子間化合物生成領域を完全に消失
させるには操作温度を85℃以上に高める必要があり、
それに伴って晶析圧力も1500kgf/cm2 程度以上にま
で高めなければならないので、高度の耐圧設備が必要と
なる。しかも常圧から加圧してその圧力が共晶圧以上に
なったときにパルミチン酸(またはステアリン酸)との
共晶として晶析してくるため、ステアリン酸(またはパ
ルミチン酸)の純度は期待したほどには上がらない。こ
の場合、圧搾の最終工程で減圧・発汗処理を行なえば、
ステアリン酸の純度はかなり高められるが、発汗工程で
相当量のステアリン酸(またはパルミチン酸)が溶出す
るため回収率が著しく低下する。However, it is necessary to raise the operating temperature to 85 ° C. or higher in order to completely eliminate the intermolecular compound forming region.
Along with this, the crystallization pressure must be increased to about 1500 kgf / cm 2 or more, so a high pressure equipment is required. Moreover, the purity of stearic acid (or palmitic acid) was expected because it will crystallize as a eutectic with palmitic acid (or stearic acid) when the pressure exceeds normal pressure and exceeds the eutectic pressure. It does not rise as much. In this case, if you perform decompression / perspiration treatment in the final step of squeezing,
The purity of stearic acid is considerably increased, but a considerable amount of stearic acid (or palmitic acid) is eluted during the perspiration process, and the recovery rate is significantly reduced.
【0013】そこで、比較的低い操作圧力であっても分
子間化合物を生成させることなく、且つ晶出したステア
リン酸(またはパルミチン酸)を高純度品として収率良
く回収することはできないかと考え更に研究を進めた。
その結果、採用する圧力晶析温度条件の下で分子間化合
物生成領域を外れる原料組成の脂肪酸混合物を使用し、
これを分子間化合物が生成する圧力未満の圧力領域まで
加圧してステアリン酸(またはパルミチン酸)の結晶を
生成せしめ、次いで降圧することにより該結晶の一部を
種結晶として残して残りの結晶を溶融させた後、該種結
晶を加圧下に成長させてから母液と分離する方法を採用
すれば、ステアリン酸(またはパルミチン酸)を高純度
で効率よく回収し得ることが確認された。Therefore, it is considered that the crystallized stearic acid (or palmitic acid) can be recovered in high yield as a high-purity product without producing an intermolecular compound even at a relatively low operating pressure. I proceeded with my research.
As a result, a fatty acid mixture having a raw material composition that is out of the intermolecular compound formation region is used under the pressure crystallization temperature conditions adopted,
This is pressurized to a pressure region lower than the pressure generated by the intermolecular compound to generate crystals of stearic acid (or palmitic acid), and then the pressure is reduced to leave a part of the crystals as seed crystals and leave the remaining crystals. It was confirmed that stearic acid (or palmitic acid) can be efficiently recovered with high purity by adopting a method in which after melting, the seed crystal is grown under pressure and then separated from the mother liquor.
【0014】こうした分離精製法を再び図3に従って説
明すると次の通りである。前述の如く圧力晶析を72℃
で行なう場合、ステアリン酸/パルミチン酸の混合組成
が30/70〜50/50の範囲からなる分子間化合物
生成領域の混合物(たとえば図3のW点)を使用したの
では、圧力晶析工程で最初に生成する結晶自体が分子間
化合物として晶出するため、ステアリン酸(またはパル
ミチン酸)を単離することはできない。従って本発明を
実施するに当たっては、採用する操作温度に応じてまず
原料としてステアリン酸/パルミチン酸の混合組成が上
記分子間化合物生成領域を外れる混合組成の脂肪酸混合
物を用いることが必須となる。The separation and purification method will be described below with reference to FIG. Pressure crystallization at 72 ° C as described above
In the case of using a mixture of stearic acid / palmitic acid in the intermolecular compound formation region (for example, point W in FIG. 3) having a mixed composition of stearic acid / palmitic acid in the range of 30/70 to 50/50, the pressure crystallization step is performed. The stearic acid (or palmitic acid) cannot be isolated because the crystals that initially form themselves crystallize out as intermolecular compounds. Therefore, in carrying out the present invention, it is essential to use a fatty acid mixture having a mixed composition of stearic acid / palmitic acid that falls outside the above-mentioned intermolecular compound formation region as a raw material, depending on the operating temperature to be adopted.
【0015】但しこの分子間化合物生成領域は前述の如
く操作温度を高めるにつれて徐々に狭まり、操作圧力を
85℃以上に高めると完全に消失するので、脂肪酸混合
物の原料組成によっては、当該組成が分子間化合物生成
領域を外れる様に操作温度を選定すれば良い。However, this intermolecular compound formation region gradually narrows as the operating temperature is raised as described above, and completely disappears when the operating pressure is raised to 85 ° C. or higher. It suffices to select the operating temperature so as to be out of the inter-compound formation region.
【0016】今、操作圧力を72℃に設定し、ステアリ
ン酸/パルミチン酸=80/20の混合物を圧力晶析す
る場合について説明すると、原料組成Zの脂肪酸混合物
(液状物)を加圧して当該圧力が曲線Cに達すると、ス
テアリン酸の結晶が生成しはじめ、更に昇圧を続けると
該結晶が徐々に増加すると共に、母液中のステアリン酸
濃度は曲線Cに沿って減少してくる。昇圧を更に続ける
と、ステアリン酸の析出量が増大すると共に母液中のス
テアリン酸濃度は更に低下し、次第に分子間化合物生成
領域に近づいてくる。そして操作圧力が曲線Bとの交点
E1 (約600kgf/cm2)にまで高まると、その時点で分
子間化合物が晶出してくるので、本発明では該圧力に達
するまでの圧力(たとえばP点)で昇圧を止める。Now, the case where the operating pressure is set to 72 ° C. and the mixture of stearic acid / palmitic acid = 80/20 is pressure-crystallized will be described. When the fatty acid mixture (liquid material) of the raw material composition Z is pressurized, When the pressure reaches the curve C, crystals of stearic acid start to be generated, and when the pressure is further increased, the crystals gradually increase and the concentration of stearic acid in the mother liquor decreases along the curve C. If the pressurization is further continued, the amount of stearic acid deposited will increase and the concentration of stearic acid in the mother liquor will further decrease, gradually approaching the intermolecular compound formation region. When the operating pressure rises to the intersection E 1 with the curve B (about 600 kgf / cm 2 ), the intermolecular compound crystallizes at that point, so in the present invention, the pressure required to reach this pressure (eg P point). ) To stop boosting.
【0017】この時点で晶出している結晶はステアリン
酸のみからなるものであるが、その結晶は非常に微細で
あり、圧搾等による完全な固液分離がむずかしい。そこ
で本発明では、P点の圧力から一旦降圧(たとえばQ
点)し、生成したステアリン酸結晶の一部を種結晶とし
て残して残部を溶融させた後、当該圧力もしくは上記分
子間化合物晶出圧力未満の任意の圧力に保持する。そう
すると、微結晶が新たにに生成することなく、ステアリ
ン酸は昇圧した時点で残った少量の種結晶のまわりに徐
々に生成して成長し、ステアリン酸の粗大な結晶が得ら
れる。従ってこれを加圧力を保持しつつ固液分離する
と、圧搾と発汗により粗大結晶の表面の極く一部を溶融
させるだけで母液付着量を殆ど皆無にすることができ、
高純度のステアリン酸を高収率で取得することができ
る。The crystals that have crystallized at this point consist of stearic acid only, but the crystals are extremely fine, and complete solid-liquid separation by pressing or the like is difficult. Therefore, in the present invention, the pressure at point P is temporarily reduced (for example, Q
Then, a part of the produced stearic acid crystal is left as a seed crystal to melt the rest, and then the pressure is maintained or an arbitrary pressure lower than the intermolecular compound crystallization pressure. Then, without newly forming fine crystals, stearic acid gradually forms and grows around the small amount of seed crystals remaining at the time of pressurization, and coarse crystals of stearic acid are obtained. Therefore, if this is subjected to solid-liquid separation while maintaining the applied pressure, the amount of mother liquor adhered can be almost eliminated only by melting a very small part of the surface of the coarse crystal by pressing and sweating.
High-purity stearic acid can be obtained in high yield.
【0018】尚上記では、72℃で圧力晶析を行なう場
合について説明したが、温度によって分子間化合物生成
領域が変わってくること、また85℃の温度では共晶が
生成するだけで分子間化合物の生成が見られなくなるこ
とは先に述べた通りであるので、原料組成に応じて処理
温度や圧力条件を適宜選定することによって、同様に高
純度のステアリン酸を高収率で得ることが可能となる。In the above description, the case of performing pressure crystallization at 72 ° C. has been explained. However, the intermolecular compound formation region changes depending on the temperature, and at the temperature of 85 ° C. only the eutectic crystal is formed and the intermolecular compound is formed. As described above, it is possible to obtain high-purity stearic acid in a high yield by appropriately selecting the processing temperature and pressure conditions according to the raw material composition. Becomes
【0019】また上記では、ステアリン酸/パルミチン
酸混合物から高純度のステアリン酸を分離精製する場合
について説明したが、同様にしてパルミチン酸の分離精
製を行なうこともできる。更に本発明は、分子間化合物
を生成し得る脂肪酸混合物から分子間化合物結晶が生成
しない様な温度および圧力条件で圧力晶析を行ない、且
つ粗大結晶を生成させることによって高純度物を取得す
るところに特徴を有するものであるから、例示した様な
ステアリン酸/パルミチン酸混合物からのステアリン酸
またはパルミチン酸の単離精製に限らず、ステアリン酸
/マルガリン酸混合物等の様に圧力晶析条件下で分子間
化合物を生成する可能性のある脂肪酸の混合物であれ
ば、あらゆる脂肪酸混合物からの特定脂肪酸の単離精製
に活用することができる。In the above description, the case of separating and purifying high-purity stearic acid from the stearic acid / palmitic acid mixture has been described, but the separation and purification of palmitic acid can be carried out in the same manner. Further, the present invention is to obtain a high-purity product by performing pressure crystallization under conditions of temperature and pressure such that intermolecular compound crystals are not produced from a fatty acid mixture capable of producing intermolecular compounds, and by producing coarse crystals. Therefore, the present invention is not limited to the isolation and purification of stearic acid or palmitic acid from a stearic acid / palmitic acid mixture as exemplified above, but is also possible under pressure crystallization conditions such as a stearic acid / margaric acid mixture. A mixture of fatty acids that may form an intermolecular compound can be utilized for isolation and purification of a specific fatty acid from any fatty acid mixture.
【0020】また原料となる脂肪酸混合物の混合組成が
分子間化合物生成領域もしくは共晶組成に近接している
場合は、本発明に係る圧力晶析法で収率を高めることが
できない場合もあるが、この様な場合は、冷却晶析、抽
出、分別蒸留等他の手段によって特定脂肪酸濃度を高め
てから本発明の精製法に適用すればよい。When the mixed composition of the fatty acid mixture as a raw material is close to the intermolecular compound formation region or the eutectic composition, the pressure crystallization method of the present invention may not be able to increase the yield. In such a case, the concentration of the specific fatty acid may be increased by other means such as cooling crystallization, extraction, and fractional distillation, and then applied to the purification method of the present invention.
【0021】[0021]
【実施例】次に本発明の実施例を示すが、本発明はもと
より下記実施例によって制限を受けるものではなく、前
・後記の趣旨に適合し得る範囲で変更して実施すること
も可能であり、それらはいずれも本発明の技術的範囲に
含まれる。EXAMPLES Examples of the present invention will be shown below. However, the present invention is not limited by the following examples, and may be modified within a range that is compatible with the gist of the above and the following. Yes, all of them are included in the technical scope of the present invention.
【0022】実施例1 ステアリン酸/パルミチン酸=88/12(モル%)の
脂肪酸混合物20gを原料とし、操作温度を72℃に設
定してこの混合物を600kgf/cm2 に昇圧した後、30
0kgf/cm2 に降圧した。これにより昇圧時に生成した微
細な結晶は大部分が再溶解し、少量の結晶が残った。次
いで同温度で500kgf/cm2 に昇圧した後10分間保持
して結晶を成長させ、500kgf/cm2 から200kgf/cm
2 まで減圧しながら母液を圧搾除去すると、純度98%
のステアリン酸が収率20%で得られた。Example 1 Starting from 20 g of a fatty acid mixture of stearic acid / palmitic acid = 88/12 (mol%), the operating temperature was set to 72 ° C., and the mixture was pressurized to 600 kgf / cm 2 and then 30
The pressure was reduced to 0 kgf / cm 2 . As a result, most of the fine crystals generated during pressurization were redissolved and a small amount of crystals remained. Next, pressurize to 500 kgf / cm 2 at the same temperature and hold for 10 minutes to grow crystals, and 500 kgf / cm 2 to 200 kgf / cm 2
98% purity when the mother liquor is squeezed off while depressurizing to 2
Stearic acid was obtained with a yield of 20%.
【0023】実施例2 ステアリン酸/パルミチン酸=93/17(モル%)の
脂肪酸混合物20gを原料とし、操作温度80℃に設定
してこの混合物を1000kgf/cm2 に昇圧した後、65
0kgf/cm2 に降圧した。次いで同温度、同圧力10分間
保持した後、母液を圧搾除去すると、純度98%のステ
アリン酸が収率22%で得られた。Example 2 Starting from 20 g of a fatty acid mixture of stearic acid / palmitic acid = 93/17 (mol%), the operating temperature was set to 80 ° C. and the pressure of this mixture was raised to 1000 kgf / cm 2 , and then 65
The pressure was reduced to 0 kgf / cm 2 . Next, after holding the same temperature and the same pressure for 10 minutes, the mother liquor was removed by squeezing to obtain stearic acid having a purity of 98% with a yield of 22%.
【0024】[0024]
【発明の効果】本発明は以上の様に構成されており、分
子間化合物の生成により高純度に単離精製することが困
難であった脂肪酸混合物から、特定脂肪酸を高純度で効
率良く回収し得ることになった。EFFECTS OF THE INVENTION The present invention is constituted as described above, and a specific fatty acid can be efficiently recovered with high purity from a fatty acid mixture which has been difficult to isolate and purify with high purity due to the formation of intermolecular compounds. I got it.
【図1】ステアリン酸/パルミチン酸混合物における圧
力をパラメータとする融解曲線を示す図である。1 is a diagram showing a melting curve with a pressure as a parameter in a stearic acid / palmitic acid mixture.
【図2】ステアリン酸/パルミチン酸混合物の常圧下に
おける融解曲線を示す図である。FIG. 2 is a diagram showing a melting curve of a stearic acid / palmitic acid mixture under normal pressure.
【図3】本発明に係る精製法を、圧力晶析時の融解曲線
に沿って例示する説明図である。FIG. 3 is an explanatory diagram illustrating the purification method according to the present invention along a melting curve during pressure crystallization.
Claims (3)
から特定の脂肪酸を単離精製する方法であって、該脂肪
酸混合物を分子間化合物が生成する圧力未満の圧力領域
まで加圧して特定脂肪酸の結晶を生成せしめ、次いで降
圧することにより該結晶の一部を種結晶として残して残
部を溶融させた後、該種結晶を加圧下に成長させてから
母液と分離することを特徴とする脂肪酸の精製法。1. A method for isolating and purifying a specific fatty acid from a mixture of fatty acids forming an intermolecular compound, which comprises pressurizing the mixture of fatty acids to a pressure region lower than the pressure at which the intermolecular compound is produced, After forming a crystal, and then lowering the pressure to leave a part of the crystal as a seed crystal and melting the rest, the seed crystal is grown under pressure and then separated from the mother liquor. Purification method.
合物生成領域を外れる原料組成の脂肪酸混合物を使用す
る請求項1記載の精製法。2. The refining method according to claim 1, wherein a fatty acid mixture having a raw material composition that is out of the intermolecular compound formation region is used under the pressure crystallization operating temperature conditions.
たはパルミチン酸の混合物であり、該脂肪酸混合物から
ステアリン酸および/またはパルミチン酸を単離精製す
る請求項1または2記載の精製法。3. The purification method according to claim 1, wherein the fatty acid mixture is a mixture of stearic acid and / or palmitic acid, and stearic acid and / or palmitic acid is isolated and purified from the fatty acid mixture.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2148493A JPH06234695A (en) | 1993-02-09 | 1993-02-09 | Method for purifying fatty acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2148493A JPH06234695A (en) | 1993-02-09 | 1993-02-09 | Method for purifying fatty acid |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH06234695A true JPH06234695A (en) | 1994-08-23 |
Family
ID=12056256
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2148493A Pending JPH06234695A (en) | 1993-02-09 | 1993-02-09 | Method for purifying fatty acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH06234695A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004029185A1 (en) | 2002-09-30 | 2004-04-08 | Fuji Oil Company, Limited | Dry fractionation method for fat |
WO2005093025A1 (en) * | 2004-03-29 | 2005-10-06 | J-Oil Mills, Inc. | Method of separating fats, seeds for use therein, and separated fat |
-
1993
- 1993-02-09 JP JP2148493A patent/JPH06234695A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004029185A1 (en) | 2002-09-30 | 2004-04-08 | Fuji Oil Company, Limited | Dry fractionation method for fat |
WO2005093025A1 (en) * | 2004-03-29 | 2005-10-06 | J-Oil Mills, Inc. | Method of separating fats, seeds for use therein, and separated fat |
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