JP3227006B2 - Method for producing fatty acid ester - Google Patents
Method for producing fatty acid esterInfo
- Publication number
- JP3227006B2 JP3227006B2 JP04196893A JP4196893A JP3227006B2 JP 3227006 B2 JP3227006 B2 JP 3227006B2 JP 04196893 A JP04196893 A JP 04196893A JP 4196893 A JP4196893 A JP 4196893A JP 3227006 B2 JP3227006 B2 JP 3227006B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- glycerin
- acid ester
- reaction product
- transesterification reaction
- 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.)
- Expired - Fee Related
Links
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、脂肪酸エステルの製造
方法に関するものであり、更に詳しくは脂肪酸グリセリ
ドと低級アルコールとをアルカリ触媒存在下でエステル
交換させて得られる脂肪酸エステル中に含まれるグリセ
リン、遊離アルカリ、石鹸等の不純物の除去を効率的に
行う脂肪酸エステルの製造方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a fatty acid ester, and more particularly to glycerin contained in a fatty acid ester obtained by transesterifying a fatty acid glyceride and a lower alcohol in the presence of an alkali catalyst. The present invention relates to a method for producing a fatty acid ester which efficiently removes impurities such as free alkali and soap.
【０００２】[0002]
【従来の技術・発明が解決しようとする課題】脂肪酸グ
リセリドに低級アルコールをアルカリ触媒存在下でエス
テル交換反応させて得られる反応物中には脂肪酸エステ
ル中以外に、グリセリン、遊離アルカリ、石鹸等の不純
物が含まれており、高品質脂肪酸エステルの製造におい
ては、これら不純物を効率良く除去する方法が望まれて
いた。その一手法として、特開昭５６−６５０９７号公
報に記載された方法がある。 Besides the fatty acid ester in the reaction product obtained by transesterification of lower alcohols to fatty acid glycerides BACKGROUND OF-0005] in the presence of an alkali catalyst, glycerin, free alkali, soap etc. Impurities are contained, and in the production of high quality fatty acid esters, a method for efficiently removing these impurities has been desired. As one of the methods, there is a method described in JP-A-56-65097.
【０００３】この方法は脂肪酸エステルを製造する際に
副生する不純物を除去するために、エステル交換反応物
中に含まれる低級アルコール量に対し０．５〜１．５倍
重量の水を添加し、かきまぜその後静置分離を行い脂肪
酸エステル層と水性低級アルコール層とに分離させて高
品質の脂肪酸エステルを得ようとする方法である。しか
しながら、このように水を抽剤とする方法では脂肪酸エ
ステルを含有する反応物中のナトリウム及び水分濃度を
微量のレベルまで低減させることは不可能である。さら
に、不純物除去の工程から発生するグリセリン水溶液か
らのグリセリンの回収において、水分除去のための蒸発
設備が必要となり、かつ多量のエネルギーを要する等の
問題を有する。さらに、排水処理設備が必要であり、設
備が複雑となる。[0003] In this method, water is added in an amount of 0.5 to 1.5 times the weight of a lower alcohol contained in a transesterification reaction product in order to remove impurities produced as a by-product when producing a fatty acid ester. This is a method in which a high-quality fatty acid ester is obtained by separating the mixture into a fatty acid ester layer and an aqueous lower alcohol layer by stirring and then allowing the mixture to stand still. However, it is impossible to reduce the concentration of sodium and water in the reaction product containing the fatty acid ester to a very small level by the method using water as the extractant. Further, in the recovery of glycerin from the glycerin aqueous solution generated from the impurity removal step, there are problems that an evaporation facility for removing water is required and a large amount of energy is required. Further, wastewater treatment equipment is required, and the equipment becomes complicated.
【０００４】本発明の目的は、かかる課題を解決すべ
く、不純物残量の極めて少ない高品質な脂肪酸エステル
を得ることができ、またエネルギー的にも有利で設備も
コンパクトである脂肪酸エステルの製造方法を提供する
ことにある。An object of the present invention is to provide a method for producing a fatty acid ester which can obtain a high-quality fatty acid ester having an extremely small amount of impurities and which is advantageous in terms of energy and has a compact facility. Is to provide.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、上記課題
を解決するために、各種不純物とグリセリンの溶解度お
よび、グリセリンの解乳化作用について鋭意研究した結
果、本発明を完成するに至った。すなわち、本発明の要
旨は、脂肪酸グリセリドと低級アルコールとをアルカリ
触媒存在下でエステル交換反応させる脂肪酸エステルの
製造方法において、反応で得られた脂肪酸エステルを含
有する反応物に対してグリセリンを抽剤として用いて抽
出操作を行うことにより、該反応物中に存在する不純物
を除去することを特徴とする脂肪酸エステルの製造方法
に関する。Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have conducted intensive studies on the solubility of various impurities and glycerin and the demulsifying action of glycerin. As a result, the present invention has been completed. . That is, the gist of the present invention is to provide a method for producing a fatty acid ester in which a fatty acid glyceride and a lower alcohol are subjected to a transesterification reaction in the presence of an alkali catalyst, wherein glycerin is extracted from a reaction product containing the fatty acid ester obtained by the reaction. The present invention relates to a method for producing a fatty acid ester, characterized in that impurities present in the reaction product are removed by performing an extraction operation using the same.
【０００６】以下に、本発明について詳細に説明する。
本発明の製造方法では、まず脂肪酸グリセリドと低級ア
ルコールとをアルカリ触媒存在下でエステル交換反応を
行い、得られた反応液からグリセリン及び低級アルコー
ルを含むグリセリン・低級アルコール溶液を分離し、脂
肪酸エステルを含有する反応物を得る。即ち、本発明に
おいて脂肪酸エステルを含有する反応物とは、エステル
交換反応後にグリセリン・低級アルコール溶液を反応液
から分離除去したものをいう。Hereinafter, the present invention will be described in detail.
In the production method of the present invention, first, a fatty acid glyceride and a lower alcohol are subjected to a transesterification reaction in the presence of an alkali catalyst, a glycerin / lower alcohol solution containing glycerin and a lower alcohol is separated from the obtained reaction solution, and A reactant containing is obtained. That is, in the present invention, the reaction product containing a fatty acid ester refers to a product obtained by separating and removing a glycerin / lower alcohol solution from the reaction solution after the transesterification reaction.
【０００７】ここで用いられる脂肪酸グリセリドとして
は、炭素数８〜２４のアルキル基またはアルケニル基を
有する脂肪酸とグリセリンとのエステルであり、例えば
パーム核、パームステアリン、椰子油、オリーブ油、ヒ
マシ油、ゴマ油、綿実油、大豆油、落花生油、ナタネ油
などの植物油、または牛脂、豚脂、鯨油などの動物油ま
たはこれらの混合物由来のものが挙げられる。低級アル
コールとしては、炭素数１〜５の低級アルコール、例え
ばメタノール、エタノール、プロパノール、ブタノー
ル、ペンタノール等が挙げられる。アルカリ触媒として
は、水酸化ナトリウム、水酸化カリウム等が挙げられ
る。The fatty acid glyceride used herein is an ester of glycerin with a fatty acid having an alkyl or alkenyl group having 8 to 24 carbon atoms, such as palm kernel, palm stearin, coconut oil, olive oil, castor oil, and sesame oil. And vegetable oils such as cottonseed oil, soybean oil, peanut oil, and rapeseed oil; and animal oils such as tallow, lard, whale oil, and mixtures thereof. Examples of the lower alcohol include lower alcohols having 1 to 5 carbon atoms, such as methanol, ethanol, propanol, butanol, and pentanol. Examples of the alkali catalyst include sodium hydroxide and potassium hydroxide.
【０００８】エステル交換反応は、特に限定されること
なく、つぎのような通常用いられる条件で好適に行うこ
とができる。即ち、脂肪酸グリセリドに対して、低級ア
ルコール１．２〜５．０モル倍、アルカリ触媒０．１〜
１．０ｗｔ％を混合し、反応温度４０〜７０℃、反応時
間１０〜１２０分でエステル交換反応を行えばよい。[0008] The transesterification is not particularly limited and can be suitably carried out under the following commonly used conditions. That is, the lower alcohol is 1.2 to 5.0 mole times the fatty acid glyceride, and the alkali catalyst is 0.1 to
1.0 wt% is mixed, and the transesterification reaction may be performed at a reaction temperature of 40 to 70 ° C and a reaction time of 10 to 120 minutes.
【０００９】反応後に得られる反応物は、脂肪酸エステ
ル以外にグリセリン、低級アルコール等が含有されてお
り、前記のようにこの反応液より、グリセリン・低級ア
ルコール溶液を分離し、抽出の対象となる脂肪酸エステ
ルを含有する反応物（以下、「エステル交換反応物」と
略す場合がある）を得る。このとき、反応液からのグリ
セリン・低級アルコール溶液の分離方法は、特に限定さ
れないが、静置分離、遠心分離等により好適に行うこと
ができる。The reaction product obtained after the reaction contains glycerin, a lower alcohol and the like in addition to the fatty acid ester. As described above, a glycerin / lower alcohol solution is separated from the reaction solution to obtain a fatty acid to be extracted. A reactant containing an ester (hereinafter, sometimes abbreviated as “transesterification reactant”) is obtained. At this time, the method of separating the glycerin / lower alcohol solution from the reaction solution is not particularly limited, but can be suitably performed by standing separation, centrifugation, or the like.
【００１０】 本発明の製造方法は、このエステル交換
反応物に対してグリセリンを抽剤として抽出操作を行う
ことにより、該反応物中に存在する不純物を除去するこ
とを特徴とするものである。ここで、不純物とは、エス
テル交換反応物中に混在するグリセリン、石鹸、遊離ア
ルカリ等をいう。グリセリンを抽剤として用いるのは、
エステル交換反応物中の不純物である遊離アルカリ、石
鹸がグリセリンへの溶解度が高いため、抽剤として添加
されたグリセリンに効率良く溶解し、このグリセリン層
を分離することによりこれらの不純物を容易に除去でき
るからである。一方、エステル交換反応物中に存在する
不純物のうちグリセリンについては、該反応物中のグリ
セリン濃度が小さく、かつ石鹸が存在するために乳化作
用によりグリセリン液滴径が微小となり沈降速度が遅く
浮遊状態にある。そこで該反応物中に抽剤であるグリセ
リンを添加することにより、解乳化作用が起こりグリセ
リン液滴径が大きくなることにより、沈降速度が増加
し、効率的に除去が可能となる。[0010] The production method of the present invention is characterized in that impurities present in the transesterification reaction product are removed by performing an extraction operation using glycerin as an extractant. Here, the impurities refer to glycerin, soap, free alkali and the like mixed in the transesterification reaction product. Glycerin is used as an extractant because
Since the free alkali and soap, which are impurities in the transesterification reaction product, have high solubility in glycerin, they are efficiently dissolved in glycerin added as an extractant, and these impurities are easily removed by separating this glycerin layer. Because you can. On the other hand, among the impurities present in the transesterification reaction product, glycerin has a low glycerin concentration in the reaction product and a small glycerin droplet diameter due to emulsification due to the presence of soap, resulting in a low sedimentation speed and a floating state. It is in. Therefore, by adding glycerin as an extractant to the reaction product , a demulsifying effect is caused and the droplet diameter of glycerin is increased, so that the sedimentation velocity is increased and efficient removal is possible.
【００１１】抽剤としてのグリセリンの使用量は、上記
のグリセリン・低級アルコール溶液を反応液から分離除
去して得られるエステル交換反応物１重量部に対して、
通常０．０２〜２重量部、好ましくは０．０２〜１．５
重量部である。グリセリンの使用量が０．０２重量部未
満では、脂肪酸エステルとグリセリンとの解乳化作用が
起こらず、またグリセリンに遊離アルカリ、石鹸が抽出
されず、これらの成分の除去効率が悪くなる。一方、グ
リセリンの使用量が２重量部を超えても、除去効率上そ
れに見合う効果がなく経済的ではない。The amount of glycerin used as an extractant is based on 1 part by weight of a transesterification reaction product obtained by separating and removing the glycerin / lower alcohol solution from the reaction solution.
Usually 0.02 to 2 parts by weight, preferably 0.02 to 1.5
Parts by weight. When the use amount of glycerin is less than 0.02 parts by weight, the demulsifying action of the fatty acid ester and glycerin does not occur, and free alkali and soap are not extracted from glycerin, so that the efficiency of removing these components deteriorates. On the other hand, if the amount of glycerin used exceeds 2 parts by weight, there is no effect corresponding to the removal efficiency and it is not economical.
【００１２】抽出操作は、特に限定されることなく、バ
ッチ式および連続式の何れにても行うことができ、例え
ばミキサーセトラー、向流多段連続抽出塔、向流多段遠
心抽出機等のいずれの抽出装置でも実施することができ
る。本発明における抽出温度は、４０〜６０℃が望まし
く、更に好ましくは４０〜５０℃である。抽出温度が６
０℃を上回ると、遊離アルカリ、石鹸の脂肪酸エステル
への溶解度が増加し除去効率が悪くなる。一方、４０℃
を下回る場合には脂肪酸エステル層とグリセリン層との
液の分離速度が遅くなり、好ましくない。The extraction operation is not particularly limited and can be carried out in any of a batch system and a continuous system. For example, any of a mixer settler, a countercurrent multistage continuous extraction column, a countercurrent multistage centrifugal extractor and the like can be used. It can also be performed with an extraction device. The extraction temperature in the present invention is preferably from 40 to 60 ° C, more preferably from 40 to 50 ° C. Extraction temperature is 6
If the temperature exceeds 0 ° C., the solubility of free alkalis and soaps in fatty acid esters increases, and the removal efficiency deteriorates. Meanwhile, 40 ° C
If the ratio is lower than the above range, the separation speed of the liquid between the fatty acid ester layer and the glycerin layer becomes low, which is not preferable.
【００１３】本発明では、抽剤として添加・混合したグ
リセリンの分離を抽出操作後に行うことにより、最終製
品である脂肪酸エステルが得られるが、グリセリンの分
離方法は、特に限定されず、静置分離、遠心分離等によ
り、好適に行うことができる。なお、本発明において
は、グリセリンによる抽出操作だけでは分離しにくい低
級アルコール等を除去するため、抽出操作前あるいは抽
出操作後に低級アルコールの減圧・留去等を行うのが好
ましい。In the present invention, a fatty acid ester as a final product can be obtained by separating glycerin added and mixed as an extractant after the extraction operation. However, the method for separating glycerin is not particularly limited, and the glycerin is separated by stationary separation. , Centrifugation or the like. In the present invention, in order to remove a lower alcohol or the like which is difficult to separate only by an extraction operation using glycerin, it is preferable to perform a reduced pressure / distillation or the like of the lower alcohol before or after the extraction operation.
【００１４】 本発明では、添加する抽剤としてグリセ
リンを用いているが、脂肪酸エステルに不溶の比重１以
上の多価アルコールも用いることができる。しかしなが
らその場合、溶剤の種類が増え抽剤の回収が必要となり
操作が複雑になる等の問題が生じる。従って、これらを
考慮するとエステル交換反応の副生物であるグリセリン
が最も経済的に用いられる。[0014] In the present invention uses glycerol as an extractant to be added, Ru can be used polyhydric alcohols gravity of one or more of the insoluble fatty acid esters. But
In that case, the type of solvent increases and it becomes necessary to collect the extractant.
Problems such as complicated operations occur. Therefore, in consideration of these, glycerin which is a by-product of the transesterification reaction is most economically used.
【００１５】[0015]
【実施例】以下、実施例および比較例により本発明をさ
らに詳しく説明するが、本発明はこれらの実施例等によ
りなんら限定されるものではない。 エステル交換反応 パーム核油に対してメタノール２．０モル倍、ＮａＯＨ
を０．５２ｗｔ％混合し、反応温度５０℃、反応時間３
０分でエステル交換反応を行った。反応後、静置分離に
よりグリセリン・メタノール溶液を除去し、脂肪酸エス
テルを含有するエステル交換反応物を得た。このエステ
ル交換反応物の組成を表１に示す。なお組成は、脂肪酸
エステルは鹸化価の測定により、ＮａＯＨ及び石鹸は２
段滴定による酸価の測定により、グリセリンは過ヨウ素
酸法により、水分はカールフィッシャー法により、メタ
ノールは１００℃、１００Ｔｏｒｒでの留出量−水分の
測定により、それぞれ求めたものである。The present invention will be described in more detail with reference to the following Examples and Comparative Examples, but the present invention is not limited to these Examples and the like. Transesterification reaction 2.0 mol times methanol relative to palm kernel oil, NaOH
Was mixed at a reaction temperature of 50 ° C. for a reaction time of 3%.
A transesterification reaction was performed in 0 minutes. After the reaction, the glycerin / methanol solution was removed by static separation to obtain a transesterification reaction product containing a fatty acid ester. Table 1 shows the composition of the transesterification product. Incidentally composition, fatty acid esters by measuring the saponification value, NaOH and soaps 2
Glycerin was determined by the periodate method, water was determined by the Karl Fischer method, and methanol was determined by distillation at 100 ° C. and 100 Torr.
【００１６】[0016]
【表１】 [Table 1]
【００１７】実施例１ 上記のエステル交換反応物に対して１重量倍のグリセリ
ンを添加し、抽出温度５０℃で１０分間混合し不純物の
抽出を行った。その後静置分離を行い下層のグリセリン
層を抜き出し、上層の脂肪酸エステル溶液に対して、エ
バポレーターにて１００℃、１００Ｔｏｒｒの条件でメ
タノールの留去を行った。この様な方法で得られた脂肪
酸エステル中の残存グリセリンと水分量の測定は上述の
方法で行い、ナトリウムの測定は原子吸光法により行っ
た。その結果を表２に示す。The addition of the 1-fold by weight glycerin to Example 1 above transesterification reaction, the extraction temperature 50 ° C. and mixed for 10 minutes was extracted impurities. Thereafter, the mixture was allowed to stand and separated, and the lower glycerin layer was extracted, and methanol was distilled off from the upper fatty acid ester solution at 100 ° C. and 100 Torr using an evaporator. The residual glycerin and water content in the fatty acid ester obtained by such a method were measured by the above-mentioned method, and sodium was measured by the atomic absorption method. Table 2 shows the results.
【００１８】[0018]
【表２】 [Table 2]
【００１９】表２に示す様に、各成分の残存量は極めて
少なく、良好な品質の脂肪酸エステルが得られた。な
お、脂肪酸エステル中の遊離アルカリ及び石鹸の残存量
は、ナトリウム濃度で表示した。As shown in Table 2, the remaining amount of each component was extremely small, and a fatty acid ester of good quality was obtained. In addition, the remaining amount of the free alkali and the soap in the fatty acid ester was represented by the sodium concentration.
【００２０】実施例２ 実施例１において、添加するグリセリン量をエステル交
換反応物に対して０．１４重量倍に変える以外は、同様
な方法でメタノールの留去までの操作を行った。得られ
た脂肪酸エステル中の残存グリセリン、ナトリウム、水
分量を表２に示す。実施例１と同様に各成分の残存量は
極めて少なく良好な品質の脂肪酸エステルが得られた。Example 2 The procedure of Example 1 was repeated, except that the amount of glycerin added was changed to 0.14 times the weight of the transesterification reaction product, until the methanol was distilled off. Table 2 shows residual glycerin, sodium, and water content in the obtained fatty acid esters. As in Example 1, the remaining amount of each component was extremely small, and a good quality fatty acid ester was obtained.
【００２１】実施例３ エステル交換反応物をエバポレーターにて１００℃、１
００Ｔｏｒｒの条件でメタノールを留去し、その後エス
テル交換反応物に対して０．１４重量倍のグリセリンを
添加し、抽出温度５０℃で１０分間混合し、不純物の抽
出を行った。その後静置分離を行い下層のグリセリン層
を抜き出して脂肪酸エステル溶液を得た。この脂肪酸エ
ステル溶液の各成分の残存量を表２に示す。表２が示す
ように、各成分の残存量が実施例１，２と同程度の良好
な品質の脂肪酸エステルが得られた。実施例１〜３の結
果から明らかなように、エステル交換反応物に対してグ
リセリンで不純物を抽出後、メタノールトッピングを行
う方法と、エステル交換反応物を先ずメタノールトッピ
ングを行い、その後グリセリン抽出を行う方法とでは脂
肪酸エステル中の不純物の残存量に差は見られなかっ
た。Example 3 The transesterified reaction product was heated at 100 ° C. for 1 hour using an evaporator.
Methanol was distilled off under the conditions of 00 Torr, and then glycerin was added in an amount of 0.14 times by weight based on the transesterification reaction mixture, and mixed at an extraction temperature of 50 ° C. for 10 minutes to extract impurities. Thereafter, the mixture was allowed to stand and separated, and the lower glycerin layer was extracted to obtain a fatty acid ester solution. Table 2 shows the remaining amount of each component of the fatty acid ester solution. As shown in Table 2, good quality fatty acid esters in which the remaining amounts of the respective components were comparable to those in Examples 1 and 2 were obtained. As is clear from the results of Examples 1 to 3, after extracting impurities with glycerin for the transesterification reaction product, a method of performing methanol topping and a method of first performing methanol topping on the transesterification reaction product and then performing glycerin extraction There was no difference in the residual amount of impurities in the fatty acid ester between the method and the method.
【００２２】実施例４ 実施例３において、添加するグリセリン量をエステル交
換反応物に対して０．０３重量倍に変える以外は、同様
な方法でグリセリン層の分離まで行った。得られた脂肪
酸エステル中の残存グリセリン、ナトリウム、水分量
は、表２に示す様に各成分の残存量は極めて少なく、良
好な品質の脂肪酸エステルが得られた。Example 4 The procedure of Example 3 was repeated, except that the amount of glycerin added was changed to 0.03 times by weight of the transesterification reaction product, until the glycerin layer was separated. As shown in Table 2, residual glycerin, sodium and water content in the obtained fatty acid ester were very small, and the fatty acid ester of good quality was obtained.
【００２３】比較例１ エステル交換反応物に対して、０．１４重量倍の水を添
加し、抽出温度５０℃で１０分間混合し、その後静置分
離を行い下層のグリセリン層を抜き出し、上層の脂肪酸
エステル溶液をエバポレーターにて１００℃、１００Ｔ
ｏｒｒの条件で水、メタノールを留去させた。この様な
方法で得られた脂肪酸エステル中の残存グリセリン、ナ
トリウム、水分量の測定を実施例１と同様の方法で行っ
た。表３に示す様に水、ナトリウムの残存量は、実施例
に比べて大きい値となり、ナトリウムの除去率は劣ると
いう結果が得られた。Comparative Example 1 To the transesterification reaction product, 0.14 weight times of water was added, and the mixture was mixed at an extraction temperature of 50 ° C. for 10 minutes. After that, the mixture was allowed to stand still to extract the lower glycerin layer, and to remove the upper glycerin layer. The fatty acid ester solution is heated at 100 ° C. and 100 T using an evaporator.
Water and methanol were distilled off under the conditions of orr. The residual glycerin, sodium and water content in the fatty acid ester obtained by such a method were measured in the same manner as in Example 1. As shown in Table 3, the residual amounts of water and sodium became larger values as compared with the examples, and the result that the removal rate of sodium was inferior was obtained.
【００２４】[0024]
【表３】 [Table 3]
【００２５】比較例２ 比較例１において、添加する水分量をエステル交換反応
物に対して０．０３重量倍に変える以外は、同様な方法
でメタノールの留去までの操作を行った。得られた脂肪
酸エステル中の残存グリセリン、ナトリウム、水分量は
表３に示す通りであり、脂肪酸エステル中の各残存量は
比較例１より劣る結果となった。Comparative Example 2 The same procedure as in Comparative Example 1 was repeated, except that the amount of water to be added was changed to 0.03 times by weight of the transesterification reaction product, until the methanol was distilled off. The residual glycerin, sodium, and water content in the obtained fatty acid ester are as shown in Table 3, and each residual amount in the fatty acid ester was inferior to Comparative Example 1.
【００２６】比較例３ エステル交換反応物をエバポレーターにて１００℃、１
００Ｔｏｒｒの条件でメタノールを留去させ、その後、
溶液温度５０℃で静置分離を行い、下層のグリセリン層
を抜き出して脂肪酸エステル溶液を得た。この脂肪酸エ
ステル溶液の各成分の残存量は、表３に示す様にナトリ
ウムの残存量の大きい結果となった。比較例３から分か
るように、メタノールを留去させるだけではグリセリン
を抽剤とした抽出操作を行った実施例と比較するとナト
リウムの残存量が多く、メタノールを除去する操作だけ
では除去効率は不十分であり、グリセリンを抽剤とした
抽出操作が必要であることがわかった。Comparative Example 3 The transesterified reaction product was heated at 100 ° C. for 1 hour using an evaporator.
Under the condition of 00 Torr, methanol was distilled off.
The solution was allowed to stand still at a solution temperature of 50 ° C., and the lower glycerin layer was extracted to obtain a fatty acid ester solution. As shown in Table 3, the remaining amount of each component of the fatty acid ester solution resulted in a large remaining amount of sodium. As can be seen from Comparative Example 3, the residual amount of sodium was larger than that of the example in which the extraction operation was performed using glycerin as the extractant only by distilling off the methanol, and the removal efficiency was insufficient only by the operation of removing the methanol. It was found that an extraction operation using glycerin as an extractant was necessary.
【００２７】以上の実施例、比較例から分かるように、
本発明では、エステル交換反応物中のグリセリン、水
分、ナトリウム、特にナトリウム濃度をごく微量まで低
減できる。一方、水による脂肪酸エステルの洗浄を行っ
た比較例１と２では、ナトリウム、水分共に実施例より
はるかに高濃度で残存しており、品質的に劣るものであ
る。また、比較例３では水分は低いものの、ナトリウム
濃度は実施例よりはるかに高く好ましくない。As can be seen from the above Examples and Comparative Examples,
In the present invention, glycerin, water, and sodium, particularly, the concentration of sodium in the transesterification reaction product can be reduced to a very small amount. On the other hand, in Comparative Examples 1 and 2 in which the fatty acid ester was washed with water, both sodium and water remained at a much higher concentration than in the examples, and the quality was inferior. Further, in Comparative Example 3, although the water content was low, the sodium concentration was much higher than in the Examples, which was not preferable.
【００２８】[0028]
【発明の効果】本発明の脂肪酸エステルの製造方法によ
れば、グリセリン、遊離アルカリ、石鹸、水分残量の極
めて少ない高品質な脂肪酸エステルを得ることができ
る。また、不純物除去の工程から発生するグリセリン溶
液からのグリセリンの回収においても蒸留塔の様な水分
を除去する設備も不要となり、エネルギー的にも有利で
あり設備もコンパクトになるので工業的に有利である。
さらに、非水系で天然油脂から脂肪酸エステルを製造す
ることが可能となり、排水処理設備が不必要となる。According to the method for producing a fatty acid ester of the present invention, it is possible to obtain a high-quality fatty acid ester having extremely low residual amounts of glycerin, free alkali, soap and water. Also, in the recovery of glycerin from the glycerin solution generated from the impurity removal step, equipment for removing water such as a distillation column is not required, which is advantageous in terms of energy and is also industrially advantageous because the equipment is compact. is there.
Furthermore, it becomes possible to produce fatty acid esters from natural fats and oils in a non-aqueous system, so that wastewater treatment equipment is not required.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ１１Ｂ 3/00 Ｃ１１Ｂ 3/00 Ｃ１１Ｃ 3/10 Ｃ１１Ｃ 3/10 (56)参考文献 特開 平２−34692（ＪＰ，Ａ) 特開 昭61−140544（ＪＰ，Ａ) 特開 昭60−35099（ＪＰ，Ａ) 特開 昭59−5142（ＪＰ，Ａ) 特開 昭56−120799（ＪＰ，Ａ) 特開 昭56−65097（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 69/24 C07C 67/03 C07C 67/58 C07C 69/533 C07C 69/587 C11B 3/00 C11C 3/10 ──────────────────────────────────────────────────続 き Continuation of the front page (51) Int.Cl. 7 Identification code FI C11B 3/00 C11B 3/00 C11C 3/10 C11C 3/10 (56) References JP-A-2-34692 (JP, A) JP-A-61-140544 (JP, A) JP-A-60-35099 (JP, A) JP-A-59-5142 (JP, A) JP-A-56-120799 (JP, A) JP-A-56-65097 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) C07C 69/24 C07C 67/03 C07C 67/58 C07C 69/533 C07C 69/587 C11B 3/00 C11C 3/10
Claims (2)
アルカリ触媒存在下でエステル交換反応させる脂肪酸エ
ステルの製造方法において、反応で得られた脂肪酸エス
テルを含有する反応物に対してグリセリンを抽剤として
用いて抽出操作を行うことにより、該反応物中に存在す
る不純物を除去することを特徴とする脂肪酸エステルの
製造方法。1. A method for producing a fatty acid ester in which a fatty acid glyceride and a lower alcohol are subjected to transesterification reaction in the presence of an alkali catalyst, wherein glycerin is used as an extractant for a reaction product containing the fatty acid ester obtained by the reaction. A method for producing a fatty acid ester, comprising removing impurities present in the reaction product by performing an extraction operation.
応物１重量部に対して０．０２〜２重量部とし、抽出温
度４０〜６０℃で抽出操作を行うことを特徴とする請求
項１記載の製造方法。2. An extraction operation at an extraction temperature of 40 to 60 ° C., wherein the amount of glycerin used as an extractant is 0.02 to 2 parts by weight based on 1 part by weight of the reactant. 2. The production method according to 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04196893A JP3227006B2 (en) | 1993-02-04 | 1993-02-04 | Method for producing fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04196893A JP3227006B2 (en) | 1993-02-04 | 1993-02-04 | Method for producing fatty acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08198810A JPH08198810A (en) | 1996-08-06 |
| JP3227006B2 true JP3227006B2 (en) | 2001-11-12 |
Family
ID=12622996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04196893A Expired - Fee Related JP3227006B2 (en) | 1993-02-04 | 1993-02-04 | Method for producing fatty acid ester |
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| Country | Link |
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| JP (1) | JP3227006B2 (en) |
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| JP5124764B2 (en) * | 2006-07-21 | 2013-01-23 | 国立大学法人 鹿児島大学 | Method for producing biodiesel fuel |
| JP5376110B2 (en) * | 2008-04-25 | 2013-12-25 | 聡 笹村 | High-purity carboxylic alcohol ester purification method and apparatus |
| CN103787884B (en) * | 2012-10-29 | 2015-10-21 | 中国石油化工股份有限公司 | A kind of application of triad extractant and extract the method for antioxidant 1010 from polyolefine material |
| CN104548653B (en) * | 2013-10-22 | 2017-06-30 | 中国石油化工股份有限公司 | A kind of quaternary extractant and its application and the method that antioxidant is extracted from polyolefin |
-
1993
- 1993-02-04 JP JP04196893A patent/JP3227006B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08198810A (en) | 1996-08-06 |
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