JPH0451541B2 - - Google Patents
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- Publication number
- JPH0451541B2 JPH0451541B2 JP62042391A JP4239187A JPH0451541B2 JP H0451541 B2 JPH0451541 B2 JP H0451541B2 JP 62042391 A JP62042391 A JP 62042391A JP 4239187 A JP4239187 A JP 4239187A JP H0451541 B2 JPH0451541 B2 JP H0451541B2
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- Prior art keywords
- fatty acid
- extraction
- mixture
- extraction fluid
- pressure
- 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.)
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Description
産業上の利用分野
本発明は、例えば、サバ、イワシ等の魚油や月
見草などの植物に多く含まれているステアリン酸
エステル、オレイン酸エステル、リノール酸エス
テル、リノレン酸エステルなどの高級脂肪酸エス
テル類を、それらの混合物から、変性、変質を生
じることなしに、効率よく、選択的に分離する高
級脂肪酸エステル混合物の分離方法に関する。
従来の技術
従来より、脂肪酸エステルの一般的な分離、抽
出技術には、自然分別法、界面活性剤応用分別
法、分子蒸留法、溶剤分別法、フルフラール、プ
ロパンによる抽出法などがある。しかし、低融
点、高ヨウ素価油から、これらの方法により不飽
和脂肪酸エステルを、安定、迅速、安価で、かつ
十分に濃縮分離することは困難である。
すなわち、自然分別法は、コストがかからない
という利点はあるが結晶化に長時間を要し、不飽
和脂肪酸エステルの分離効率が良好でない。
分子蒸留法は、重合や異性化が生じやすく変性
しやすい上に、あらかじめ揮発しやすい物質をと
りさる脱ガス処理が必要で工程が煩雑になるのを
免れない。
溶剤分別法は、ある程度収率も高く、不飽和脂
肪酸エステルが得られるが、そのためにかなりの
低温を必要としコストが高くなり、溶剤除去も困
難である。
発明が解決しようとする課題
本発明は、このような従来の脂肪酸エステルの
分離技術のもつ欠点を克服し、高級脂肪酸エステ
ル混合物から、各脂肪酸エステルを、極めて温和
な条件下で、変質させることなく選択的に分離し
うる方法を提供することを目的としてなされたも
のである。
課題を解決するための手段
一般に、気体と固体あるいは液体を接触させた
場合、常圧、常温下において気相に移行する固体
あるいは液体の量は、極めてわずかである。しか
し、気体の種類を適当に選び、かつその気体が臨
界温度以上の温度及び臨界圧以上の圧力の状態に
あるときは、気相に移行する固体あるいは液体の
量は飛躍的に増大する。
また硝酸銀は、高級脂肪酸エステル類の不飽和
度が増大するにつれて、それらの間の親和力は増
大してくる。
本発明者らは、これらの事実に着目し、高級脂
肪酸エステルを、化学的に不活性であつて臨界温
度が０〜50℃の範囲にある抽出流体と、その臨界
温度以上の温度及び臨界圧以上の圧力で接触後カ
ラムに充填されている硝酸銀を担持した粉体内を
通過させることによつて、不飽和度の大きいもの
程カラム内に担持しうること及びこのカラムに、
酢酸エチルなどの低級脂肪酸エステルを含んだ前
記抽出流体を流すことによつて、高級脂肪酸エス
テルの不飽和度に応じてさらに抽出分離しうるこ
とを見出し、これらの知見に基いて本発明を完成
するに至つた。
すなわち、本発明は、２種以上の高級脂肪酸エ
ステルの混合物を、該エステルに対して化学的に
不活性であつて臨界温度が０〜50℃の範囲にある
抽出流体と、その臨界温度以上の温度及び臨界圧
以上の圧力の条件下で接触させ、該エステルを抽
出流体中へ移行させた上で、該抽出流体を硝酸銀
を担持した粉体を充填したカラム内を通過させて
混合物中の一部の高級脂肪酸エステルをカラム内
に吸着させたのち、これを、吸着されたエステル
混合物に化学的に不活性であつて臨界温度が０〜
50℃の範囲にある抽出流体に低級脂肪酸エステル
を１〜15重量％添加した溶液により臨界温度以上
の温度で臨界圧以上の圧力の条件下で溶離させる
ことを特徴とする高級脂肪酸エステル混合物の分
離方法を提供するものである。
本発明の分離方法が適用される高級脂肪酸エス
テルは炭素数12〜24の飽和又は不飽和脂肪酸のエ
ステルである。
本発明における抽出処理圧力は高いほど溶解度
が大きくなるが、選択性は減少するので、抽出流
体の臨界圧より10〜150Kg／cm2高い圧力範囲を用
いるのが望ましい。経済的には圧力は80〜220
Kg／cm2とするのが好ましい。
抽出温度は臨界温度以上でなければならない
が、臨界温度より１〜50℃高い温度範囲を用いる
のが抽出物の変質を防ぐ上から望ましい。
本発明に用いる抽出流体としては臨界温度が０
〜50℃の範囲にある物質、例えば二酸化炭素、エ
タン、エチレン等を主体とするものなどが用いら
れ、特に二酸化炭素が好ましい。この臨界温度が
高くなると抽出温度も上がるため不飽和エステル
の変質が起こりやすくなる。
本発明において硝酸銀カラムの抽出に用いる抽
出流体としては、上記抽出流体に低級脂肪酸エス
テルを１〜15重量％添加したものが用いられる。
この低級脂肪酸エステルは炭素数６以下の脂肪酸
と炭素数３以下のアルコールからなるエステルが
適しており、そのようなものとしては、例えば吉
草酸エチル、酪酸エチル、プロピオン酸エチル、
酢酸エチルなどが挙げられる。
この抽出流体は、低級脂肪酸エステルの種類及
び含量を調節することによつて高級脂肪酸エステ
ルに対する親和力を変化させることができる。
抽出流体の使用量は、抽出量、高級脂肪酸エス
テル混合物の組成と組成比によつて異なるが、通
常、１回の抽出操作当り原料脂肪酸エステル量の
100〜200倍である。
本発明においては、第一段の抽出操作前に、該
抽出に用いる抽出流体中へ低級脂肪酸エステルを
添加してもよい。
本発明に好適に用いられる充填カラムとして
は、例えば硝酸銀を65〜100メツシユのシリカゲ
ル又はアルミナ粉体に担持し、これをステンレス
製カラムに充填したものなどが挙げられる。
このようにして、本発明においては、第一に抽
出流体の高級脂肪酸エステルに対する抽出能力を
活用し、第二に硝酸銀カラムに対する各供給脂肪
酸エステルの不飽和度によつて異なる親和力の差
を活用し、第三に低級脂肪酸エステルの添加され
た抽出流体に対する各高級脂肪酸エステルの不飽
和度等によつて異なる親和力の差を活用して高級
脂肪酸エステル混合物から各エステルを分離する
ことができる。
この各高級脂肪酸エステルに対する抽出流体又
は硝酸銀カラムの親和力は、抽出流体の種類、抽
出温度、抽出圧力、抽出流体中の低級脂肪酸エス
テルの種類と濃度等によつても異なる。
本発明においては、分離すべき混合物中の高級
脂肪酸エステルの種類及び組成比に応じ、本発明
の方法の中で最も適した抽出条件を選択し、これ
らの抽出方法を２種以上組み合わせたり２回以上
繰り返したりして各高級脂肪酸エステルを分離す
ることができる。
例えばステアリン酸エステル、オレイン酸エス
テル、リノール酸エステル、リノレン酸エステル
などの高級脂肪酸エステル混合物を分離する場
合、まず、例えば二酸化炭素を抽出流体として、
その臨界温度以上の温度、臨界圧以上の圧力で混
合物と接触させ、高級脂肪酸エステルを抽出す
る。次いでこれを硝酸銀カラムに通過させると、
ステアリン酸エステルのみがカラムを通過し、他
のエステルはカラム中に捕らえられる。次に低級
脂肪酸エステルを含有する抽出流体をカラムに流
すと、各高級脂肪酸エステルに対する抽出流体の
溶解能及びカラムの吸着能の差に応じ順次各高級
脂肪酸エステルが抽出される。各抽出分につい
て、場合により条件を変えて、本発明の抽出操作
を繰り返すことにより純度を上げることができ
る。
発明の効果
本発明の方法によれば、従来の方法とは異な
り、ほぼ常温で、操作も簡単な上、低コストで高
級脂肪酸エステル混合物から高級脂肪酸エステル
類を選択的に抽出分離できる。
その際、高級脂肪酸エステル混合物の組成及び
組成比に応じて、抽出温度、抽出圧力、抽出流体
の使用量、抽出流体の種類、抽出流体に添加する
低級脂肪酸エステルの種類、含有量又は濃度等を
適宜選択して、分離すべき混合物に接触させるこ
とができ、これにより該混合物中の各高級脂肪酸
エステルを順次単独に分離することができるので
有利である。
実施例
次に実施例によつて本発明をさらに詳細に説明
する。脂肪酸エステル組成は、ガスクロマトグラ
フイーにより測定した。
実施例 １
ステアリン酸メチル、オレイン酸メチル、リノ
ール酸メチル、リノレン酸メチルの混合物7.98ｇ
（C18:0：C18:1：C18:2：C18:3＝28.95：
19.45：28.19：23.41）を抽出器に仕込み、恒温槽
の温度を38℃に保ち、二酸化炭素を91Kg／cm2で60
／ｈの速度で吹き込み接触させた。上記混合物
を溶解した上記流体は、硝酸銀を担持したシリカ
ゲル粉体を充填したカラム内に導かれた。カラム
温度は57℃とした。カラムを通過した流体は、フ
イルター、圧力調整弁を経て、常圧、38℃の分離
器に導かれ、上記混合物中からステアリン酸メチ
ルが分離された。この抽出物の抽出速度、脂肪酸
組成は、第１表、第２表にそれぞれ示すとおりで
ある。これより、上記脂肪酸メチル混合物から飽
和脂肪酸メチルのステアリン酸メチルが高選択的
に高収率で得られることが分る。
次いで、酢酸エチルを４重量％含有する二酸化
炭素を用い、91Kg／cm2で60／ｈの速度でカラム
内を通過させ、カラム内に保持されたステアリン
酸メチル、オレイン酸メチル、リノール酸メチ
ル、リノレン酸メチルの混合物と接触させた。流
体は、接触後、フイルター、圧力調整弁を経て、
常圧、40℃の分離器に導かれ、抽出物が得られ
た。この抽出物の抽出速度、脂肪酸組成は、第３
表に示すとおりである。これより、不飽和度３の
リノレン酸メチルが高選択的に得られることが分
る。
Industrial Application Fields The present invention utilizes higher fatty acid esters such as stearate, oleate, linoleate, and linolenic acid esters, which are abundantly contained in fish oils such as mackerel and sardines, and plants such as evening primrose. The present invention relates to a method for separating higher fatty acid ester mixtures efficiently and selectively from mixtures thereof without causing denaturation or alteration. Conventional techniques Conventionally, general separation and extraction techniques for fatty acid esters include natural fractionation, surfactant-applied fractionation, molecular distillation, solvent fractionation, and extraction using furfural and propane. However, it is difficult to stably, quickly, inexpensively, and sufficiently concentrate and separate unsaturated fatty acid esters from low melting point, high iodine value oils by these methods. That is, the natural fractionation method has the advantage of being low cost, but requires a long time for crystallization, and the separation efficiency of unsaturated fatty acid esters is not good. Molecular distillation methods tend to cause polymerization and isomerization, and are susceptible to denaturation, and require degassing treatment to remove easily volatile substances in advance, making the process complicated. Although the solvent fractionation method has a somewhat high yield and can obtain unsaturated fatty acid esters, it requires a considerably low temperature, resulting in high costs, and it is difficult to remove the solvent. Problems to be Solved by the Invention The present invention overcomes the drawbacks of conventional fatty acid ester separation techniques, and separates each fatty acid ester from a higher fatty acid ester mixture under extremely mild conditions without deterioration. This was done with the aim of providing a method that allows selective separation. Means for Solving the Problems Generally, when a gas and a solid or liquid are brought into contact, the amount of the solid or liquid that changes to the gas phase at normal pressure and room temperature is extremely small. However, when the type of gas is appropriately selected and the gas is at a temperature higher than the critical temperature and a pressure higher than the critical pressure, the amount of solid or liquid transferred to the gas phase increases dramatically. Furthermore, as the degree of unsaturation of higher fatty acid esters increases, the affinity between silver nitrate and higher fatty acid esters increases. The present inventors focused on these facts, and extracted higher fatty acid esters by using an extraction fluid that is chemically inert and has a critical temperature in the range of 0 to 50°C, and a temperature above the critical temperature and a critical pressure. By passing through the powder carrying silver nitrate packed in the column after contacting with the above pressure, it is possible to carry silver nitrate in the column with a higher degree of unsaturation, and in this column,
We have discovered that by flowing the extraction fluid containing lower fatty acid esters such as ethyl acetate, it is possible to further extract and separate higher fatty acid esters depending on the degree of unsaturation, and based on these findings, we have completed the present invention. It came to this. That is, the present invention extracts a mixture of two or more higher fatty acid esters with an extraction fluid that is chemically inert to the esters and has a critical temperature in the range of 0 to 50°C, and The ester is brought into contact with the mixture under conditions of temperature and pressure higher than the critical pressure to transfer the ester into the extraction fluid, and the extraction fluid is passed through a column filled with powder supporting silver nitrate to remove the ester in the mixture. After adsorbing 10% of higher fatty acid esters in the column, this is added to the adsorbed ester mixture in a column that is chemically inert and has a critical temperature of 0 to 0.
Separation of a higher fatty acid ester mixture characterized by elution under conditions of a temperature higher than the critical temperature and a pressure higher than the critical pressure using a solution containing 1 to 15% by weight of lower fatty acid ester added to an extraction fluid in the range of 50°C. The present invention provides a method. Higher fatty acid esters to which the separation method of the present invention is applied are esters of saturated or unsaturated fatty acids having 12 to 24 carbon atoms. The higher the extraction pressure in the present invention, the higher the solubility, but the lower the selectivity, so it is desirable to use a pressure range that is 10 to 150 Kg/cm 2 higher than the critical pressure of the extraction fluid. Economically the pressure is 80-220
Preferably it is Kg/cm 2 . Although the extraction temperature must be higher than the critical temperature, it is desirable to use a temperature range of 1 to 50°C higher than the critical temperature in order to prevent deterioration of the extract. The extraction fluid used in the present invention has a critical temperature of 0.
Substances in the range of ~50°C, such as those mainly composed of carbon dioxide, ethane, ethylene, etc., are used, and carbon dioxide is particularly preferred. As this critical temperature increases, the extraction temperature also increases, making it easier for unsaturated esters to undergo deterioration. In the present invention, the extraction fluid used in the silver nitrate column extraction is the above extraction fluid to which 1 to 15% by weight of lower fatty acid ester is added.
Suitable lower fatty acid esters are esters consisting of fatty acids with 6 or less carbon atoms and alcohols with 3 or less carbon atoms, such as ethyl valerate, ethyl butyrate, ethyl propionate,
Examples include ethyl acetate. The affinity of this extraction fluid for higher fatty acid esters can be changed by adjusting the type and content of lower fatty acid esters. The amount of extraction fluid used varies depending on the amount of extraction and the composition and composition ratio of the higher fatty acid ester mixture, but usually the amount of raw fatty acid ester per extraction operation is
It is 100 to 200 times. In the present invention, a lower fatty acid ester may be added to the extraction fluid used for the extraction before the first stage extraction operation. Examples of packed columns suitable for use in the present invention include those in which silver nitrate is supported on 65 to 100 meshes of silica gel or alumina powder, and this is packed in a stainless steel column. In this way, the present invention firstly utilizes the extraction ability of the extraction fluid for higher fatty acid esters, and secondly exploits the difference in affinity of each supplied fatty acid ester for the silver nitrate column depending on the degree of unsaturation. Thirdly, each ester can be separated from a higher fatty acid ester mixture by utilizing the difference in affinity of each higher fatty acid ester, which varies depending on the degree of unsaturation, etc., with respect to the extraction fluid to which the lower fatty acid ester is added. The affinity of the extraction fluid or silver nitrate column for each higher fatty acid ester differs depending on the type of extraction fluid, extraction temperature, extraction pressure, type and concentration of lower fatty acid ester in the extraction fluid, etc. In the present invention, the most suitable extraction conditions among the methods of the present invention are selected depending on the type and composition ratio of the higher fatty acid ester in the mixture to be separated, and two or more of these extraction methods are combined or extracted twice. By repeating the above steps, each higher fatty acid ester can be separated. For example, when separating a mixture of higher fatty acid esters such as stearate ester, oleate ester, linoleate ester, linolenic acid ester, etc., first, for example, carbon dioxide is used as an extraction fluid.
The higher fatty acid ester is extracted by contacting the mixture at a temperature higher than the critical temperature and a pressure higher than the critical pressure. This is then passed through a silver nitrate column,
Only stearate esters pass through the column, other esters are trapped in the column. Next, when an extraction fluid containing lower fatty acid esters is passed through the column, each higher fatty acid ester is sequentially extracted according to the difference in the solubility of the extraction fluid and the adsorption ability of the column for each higher fatty acid ester. The purity of each extract can be increased by repeating the extraction operation of the present invention, changing the conditions as the case requires. Effects of the Invention According to the method of the present invention, unlike conventional methods, higher fatty acid esters can be selectively extracted and separated from a higher fatty acid ester mixture at approximately room temperature, easy to operate, and at low cost. At that time, depending on the composition and composition ratio of the higher fatty acid ester mixture, the extraction temperature, extraction pressure, amount of extraction fluid used, type of extraction fluid, type, content or concentration of lower fatty acid ester added to the extraction fluid, etc. This is advantageous because it can be selected as appropriate and brought into contact with the mixture to be separated, thereby allowing each higher fatty acid ester in the mixture to be separated individually in sequence. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples. Fatty acid ester composition was measured by gas chromatography. Example 1 7.98g mixture of methyl stearate, methyl oleate, methyl linoleate, and methyl linolenate
( C18 : 0 : C18 : 1 : C18 : 2 : C18 : 3 =28.95:
19.45:28.19:23.41) into the extractor, keep the temperature of the constant temperature bath at 38℃, and add carbon dioxide at 91Kg/ cm2 to 60℃.
The contact was made by blowing at a speed of /h. The fluid containing the mixture was introduced into a column filled with silica gel powder carrying silver nitrate. Column temperature was 57°C. The fluid that passed through the column was led to a separator at normal pressure and 38° C. through a filter and a pressure regulating valve, and methyl stearate was separated from the above mixture. The extraction rate and fatty acid composition of this extract are shown in Tables 1 and 2, respectively. This shows that methyl stearate, which is a saturated fatty acid methyl, can be obtained with high selectivity and high yield from the above fatty acid methyl mixture. Next, using carbon dioxide containing 4% by weight of ethyl acetate, it was passed through the column at a rate of 60/h at 91 kg/cm 2 to remove the methyl stearate, methyl oleate, methyl linoleate, and Contacted with a mixture of methyl linolenate. After contact, the fluid passes through a filter and pressure regulating valve,
The mixture was introduced into a separator at normal pressure and 40°C to obtain an extract. The extraction rate and fatty acid composition of this extract are
As shown in the table. This shows that methyl linolenate with an unsaturation degree of 3 can be obtained with high selectivity.
【表】【table】
【表】【table】
【表】
参考例 １
ステアリン酸メチル、オレイン酸メチル、リノ
ール酸メチル、リノレン酸メチルの混合物7.90ｇ
（C18:0：C18:1：C18:2：C18:3＝27.95：
20.45：26.09：25.51）を抽出器に仕込み、抽出圧
力を111Kg／cm2としたこと以外は実施例と同様に
して抽出物を得た。この抽出物の脂肪酸組成、抽
出速度は、第４表に示すとおりである。これよ
り、実施例と比較して、抽出速度は圧力によつて
増加し、またやはりC18:0の分離効率が高いこと
が分る。
参考例 ２
ステアリン酸メチル、オレイン酸メチル、リノ
ール酸メチル、リノレン酸メチルの混合物8.10ｇ
（C18:0：C18:1：C18:2：C18:3＝27.55：
20.85：27.00：26.60）を抽出器に仕込み、抽出圧
力を111Kg／cm2、カラム温度80℃としたこと以外
は実施例と同様にして抽出物を得た。この抽出物
の脂肪酸組成、抽出速度は、第５表に示すとおり
である。[Table] Reference example 1 7.90g mixture of methyl stearate, methyl oleate, methyl linoleate, and methyl linolenate
( C18 : 0 : C18 : 1 : C18 : 2 : C18 : 3 =27.95:
20.45:26.09:25.51) was charged into the extractor, and an extract was obtained in the same manner as in Example except that the extraction pressure was 111 Kg/cm 2 . The fatty acid composition and extraction rate of this extract are as shown in Table 4. From this, it can be seen that the extraction rate increases with pressure, and the separation efficiency of C 18 : 0 is also high, as compared to the examples. Reference example 2 8.10g mixture of methyl stearate, methyl oleate, methyl linoleate, and methyl linolenate
( C18 : 0 : C18 : 1 : C18 : 2 : C18 : 3 =27.55:
20.85:27.00:26.60) was charged into the extractor, and an extract was obtained in the same manner as in Example except that the extraction pressure was 111 Kg/cm 2 and the column temperature was 80°C. The fatty acid composition and extraction rate of this extract are as shown in Table 5.
【表】【table】
【表】
次に、抽出流体として、二酸化炭素単独と、そ
れに酢酸エチルを含有させたもの（参考例３〜５
は酢酸エチル含有率４重量％、参考例６は酢酸エ
チル含有率10重量％）を用いた各場合について、
不飽和高級脂肪酸エステルの抽出速度あるいは抽
出効率を比較した例を、以下の参考例３〜６に示
した。
参考例 ３
トリオレイン10.31ｇを抽出器に仕込み、40℃に
保つたものを２個用意し、それぞれに各抽出流体
を200Kg／cm2、60／ｈの速度で吹き込み接触さ
せた。トリオレインを溶解した上記流体は、フイ
ルター、圧力調整弁を経て、常圧、０℃の分離器
に導かれ、トリオレインは分離された。分離後、
減圧下で酢酸エチルを除去し、トリオレインを得
た。このトリオレイン抽出速度は第６表に示すと
おりである。これより、低級脂肪酸エステルを含
有する抽出流体の方が不飽和成分の収量の増加が
著しいことが分る。
参考例 ４
トリオレイン9.71ｇ、トリステアリン9.73ｇを
抽出器に仕込んだ以外は参考例３と同様にして各
抽出物を得た。この各抽出物の脂肪酸組成を第７
表に示す。これより、低級脂肪酸エステルを含有
する抽出流体の方が不飽和成分の抽出効率に優れ
ることが分る。
参考例 ５
ステアリン酸メチル9.60ｇとリノール酸メチル
9.71ｇを抽出器に仕込んだ以外は参考例３と同様
にして各抽出物を得た。この各抽出物の脂肪酸組
成を第７表に示す。これより、低級脂肪酸エステ
ルを含有する抽出流体の方が不飽和成分の抽出効
率に優れることが分る。
参考例 ６
ステアリン酸メチル9.82ｇとオレイン酸メチル
9.99ｇを抽出器に仕込み、40℃に保ち、抽出流体
量を280Kg／cm2としたこと以外は参考例３と同様
にして各抽出物を得た。この各抽出物の脂肪酸組
成を第７表に示す。これより、低級脂肪酸エステ
ルを含有する抽出流体の方が不飽和成分の抽出効
率に優れることが分る。[Table] Next, carbon dioxide alone and ethyl acetate were added as extraction fluids (Reference Examples 3 to 5).
For each case using ethyl acetate content of 4% by weight and Reference Example 6 using ethyl acetate content of 10% by weight),
Examples comparing the extraction speed or extraction efficiency of unsaturated higher fatty acid esters are shown in Reference Examples 3 to 6 below. Reference Example 3 10.31 g of triolein was charged into an extractor and kept at 40°C. Two extractors were prepared, and each extraction fluid was blown into each extractor at a rate of 200 kg/cm 2 and 60/h to bring them into contact. The above fluid in which triolein was dissolved passed through a filter and a pressure regulating valve, and was led to a separator at normal pressure and 0° C., where triolein was separated. After separation,
Ethyl acetate was removed under reduced pressure to obtain triolein. The triolein extraction rate is shown in Table 6. This shows that the extraction fluid containing the lower fatty acid ester has a more remarkable increase in the yield of unsaturated components. Reference Example 4 Each extract was obtained in the same manner as Reference Example 3 except that 9.71 g of triolein and 9.73 g of tristearin were charged into the extractor. The fatty acid composition of each extract was
Shown in the table. This shows that the extraction fluid containing the lower fatty acid ester has better extraction efficiency for unsaturated components. Reference example 5 9.60g of methyl stearate and methyl linoleate
Each extract was obtained in the same manner as in Reference Example 3 except that 9.71 g was charged into the extractor. The fatty acid composition of each extract is shown in Table 7. This shows that the extraction fluid containing the lower fatty acid ester has better extraction efficiency for unsaturated components. Reference example 6 9.82g of methyl stearate and methyl oleate
Each extract was obtained in the same manner as in Reference Example 3, except that 9.99 g was charged into an extractor, kept at 40° C., and the amount of extraction fluid was 280 Kg/cm 2 . The fatty acid composition of each extract is shown in Table 7. This shows that the extraction fluid containing the lower fatty acid ester has better extraction efficiency for unsaturated components.
【表】【table】
Claims (1)
該エステルに対して化学的に不活性であつて臨界
温度が０〜50℃の範囲にある抽出流体と、その臨
界温度以上の温度及び臨界圧以上の圧力の条件下
で接触させ、該エステルを抽出流体中へ移行させ
た上で、該抽出流体を硝酸銀を担持した粉体を充
填したカラム内を通過させて混合物中の一部の高
級脂肪酸エステルをカラム内に吸着させたのち、
これを、吸着されたエステル混合物に化学的に不
活性であつて臨界温度が０〜50℃の範囲にある抽
出流体に低級脂肪酸エステルを１〜15重量％添加
した溶液により臨界温度以上の温度で臨界圧以上
の圧力の条件下で溶離させることを特徴とする高
級脂肪酸エステル混合物の分離方法。1 A mixture of two or more higher fatty acid esters,
The ester is brought into contact with an extraction fluid that is chemically inert to the ester and has a critical temperature in the range of 0 to 50°C under conditions of a temperature above the critical temperature and a pressure above the critical pressure. After transferring into the extraction fluid, the extraction fluid is passed through a column filled with powder supporting silver nitrate to adsorb some higher fatty acid esters in the mixture into the column.
This is carried out at a temperature above the critical temperature using a solution in which 1 to 15% by weight of a lower fatty acid ester is added to an extraction fluid that is chemically inert to the adsorbed ester mixture and whose critical temperature is in the range of 0 to 50°C. A method for separating higher fatty acid ester mixtures, characterized by elution under pressure conditions higher than critical pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4239187A JPS63208549A (en) | 1987-02-25 | 1987-02-25 | Separation of higher fatty acid ester mixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4239187A JPS63208549A (en) | 1987-02-25 | 1987-02-25 | Separation of higher fatty acid ester mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63208549A JPS63208549A (en) | 1988-08-30 |
| JPH0451541B2 true JPH0451541B2 (en) | 1992-08-19 |
Family
ID=12634767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4239187A Granted JPS63208549A (en) | 1987-02-25 | 1987-02-25 | Separation of higher fatty acid ester mixture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63208549A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU632847B2 (en) * | 1989-09-08 | 1993-01-14 | Siegfried Peter | Process for preparing pure monoglycerides, pure diglycerides and/or pure triglycerides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3405151A (en) * | 1966-07-01 | 1968-10-08 | Upjohn Co | Chromatographic separation of gamma-linolenic acid esters |
| JPS5484519A (en) * | 1977-12-16 | 1979-07-05 | Kagakuhin Kensa Kiyoukai | Method of purifying longgchained and highly unsaturated fatty acids |
-
1987
- 1987-02-25 JP JP4239187A patent/JPS63208549A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63208549A (en) | 1988-08-30 |
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