JP4336919B2 - Process for producing fatty acid monoalkanolamide - Google Patents
Process for producing fatty acid monoalkanolamide Download PDFInfo
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- JP4336919B2 JP4336919B2 JP23023299A JP23023299A JP4336919B2 JP 4336919 B2 JP4336919 B2 JP 4336919B2 JP 23023299 A JP23023299 A JP 23023299A JP 23023299 A JP23023299 A JP 23023299A JP 4336919 B2 JP4336919 B2 JP 4336919B2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/00—Technologies relating to chemical industry
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Description
【０００１】
【発明の属する技術分野】
本発明は、未反応原料およびエステルアミドの含量が充分に低く、且つ色相が良く、しかも臭いの少ない脂肪酸モノアルカノールアミドを経済的に製造する方法に関するものである。
【０００２】
【従来の技術】
脂肪酸モノアルカノールアミドは、優れた起泡安定性、増粘作用を有するため、洗浄剤の補助剤、添加剤として広く用いられている。
【０００３】
従来、脂肪酸モノアルカノールアミドは、脂肪酸メチルエステルとモノアルカノールアミンをアルカリ触媒の存在下で反応させる方法で製造されている。その際に、未反応のエステルやエステルアミド等の副生物の生成を抑えるために、通常は脂肪酸メチルエステル１．０モルに対して、モノアルカノールアミンを１．０１〜１．２０モルと過剰に使用し、またアルカリ触媒を多目に用いて反応する方法が一般的に行われている。
【０００４】
しかし、モノアルカノールアミンを過剰に、アルカリ触媒を多目に用いる方法では、製品中にモノアルカノールアミンおよびアルカリ触媒が残存することになり、純度、色相、臭い等が悪くなり、またアルカリ価が高くなる等の欠点があった。
【０００５】
これらの欠点を改良する目的で、（１）反応終了後加熱しながら高真空下で過剰のモノアルカノールアミンを除去する方法、（２）反応終了後アルカリ触媒と過剰のモノアルカノールアミンを酸性物質で中和する方法等のいくつかの処理方法が行われていた。
【０００６】
【発明が解決しようとする課題】
しかしながら、製品の純度向上を目的に、加熱しながら高真空下で過剰のモノアルカノールアミンを除去する（１）の方法では、アルカリ触媒によって転移反応が起きて、エステルアミドが副生する問題があった。
【０００７】
また、アルカリ触媒と過剰のモノアルカノールアミンを硫酸，塩酸，リン酸，クエン酸，乳酸またはラウリン酸等の酸性物質で中和する（２）の方法では、それらの中和塩が残存するため高純度な製品が得られず、また中和を行ったものは、生成する塩の影響により、色相が悪化するという問題があった。
【０００８】
さらに、脂肪酸メチルエステルに対するモノアルカノールアミンの過剰量とアルカリ触媒の使用量を減らす方法も考えられるが、この方法は反応が完結しにくいため未反応の脂肪酸エステルによる臭いや、エステルアミド等が副生して純度が悪くなるなどの問題があった。
【０００９】
本発明が解決しようとする課題は、従来の脂肪酸モノアルカノールアミドの製法上の問題点を改良し、未反応原料およびエステルアミドが充分低く、且つ色相が良く、臭いの少ない経済的な脂肪酸モノアルカノールアミドの製造方法を提供することである。
【００１０】
【課題を解決するための手段】
上記課題を解決するために、本発明者等は鋭意検討した結果、脂肪酸メチルエステルに対し、モノアルカノールアミンをアルカリ触媒の存在下で反応させ脂肪酸モノアルカノールアミドを合成する方法において、縮合反応終了後水を加えて加熱した後、減圧下で水を除去することにより、未反応原料およびエステルアミドが充分低く、且つ色相が良く、臭いの少ない脂肪酸モノアルカノールアミドを製造できることを見出し、本発明を完成させるに至った。
【００１１】
すなわち、本発明は一般式（１）
【００１２】
【化３】
（式中のＲは、ヒドロキシ基で置換されていてもよい炭素数５〜２１の直鎖もしくは分岐鎖のアルキル基またはアルケニル基を表す）
で示される脂肪酸メチルエステルに対し、一般式（２）
【００１４】
【化４】
（式中Ｘは、ＨまたはＣＨ3を表す）
で示されるモノアルカノールアミンをアルカリ触媒の存在下で縮合反応させ脂肪酸モノアルカノールアミドを合成する方法において、縮合反応終了後水を加えて加熱した後、減圧下で水を除去することを特徴とする脂肪酸モノアルカノールアミドの製造方法に関するものである。
【００１６】
【発明の実施の形態】
以下、本発明の脂肪酸モノアルカノールアミドの製造方法について詳細に説明する。
【００１７】
本発明において使用される前記一般式（１）の脂肪酸メチルエステルにおいて、式中のＲは、ヒドロキシ基で置換されていてもよい炭素数５〜２１の直鎖もしくは分岐鎖のアルキル基またはアルケニル基であれば特に限定されず、単一組成のものでも、２種類以上の混合物でも構わない。一般式（１）で表される脂肪酸メチルエステルとしては、例えば、ラウリン酸、ミリスチン酸、ステアリン酸、１２−ヒドロキシステアリン酸、オレイン酸、ヤシ脂肪酸、パーム脂肪酸、牛脂脂肪酸などのメチルエステルを挙げることができる。
【００１８】
また、一般式（２）で表されるモノアルカノールアミンとしては、モノエタノールアミン、イソプロパノールアミンのいずれかを選ぶことができる。
【００１９】
本発明の脂肪酸アルカノールアミドの製造において用いられるアルカリ触媒としては、例えば、水酸化ナトリウム、水酸化カリウム等の水酸化物、ナトリウムメチレート、ナトリウムエチラート、カリウムエチラート等のアルコラート系塩基性触媒を挙げることができる。
【００２０】
従来の方法によって製造された脂肪酸モノアルカノールアミドには、目的物の他にアルカリ触媒および過剰のモノアルカノールアミンが含まれる。従来の技術では、硫酸，塩酸，リン酸，クエン酸，乳酸またはラウリン酸等の酸性物質を用いて中和するため、製品中にはアルカリおよびモノアルカノールアミンの塩が残存することになり、この塩が着色の主な原因であった。
【００２１】
本発明では、酸性物質を用いずに、水を添加し、未反応の脂肪酸メチルエステルおよび目的物の脂肪酸アルカノールアミドとアルカリ触媒とを鹸化反応させて脂肪酸石鹸に転化すると共に、反応に使用されなかった余分な水を減圧下で留出することにより系内に残存する過剰のモノアルカノールアミンを飛沫同伴作用によって同時に留出させるため、着色の原因となる塩の混入がなく、色相が良好で、エステル臭，アミン臭等がない臭いの良い製品を得ることが可能である。
【００２２】
一般式（１）の脂肪酸メチルエステルと一般式（２）のモノアルカノールアミンとの反応は、従来から知られている方法、すなわち脂肪酸メチルエステルとモノアルカノールアミンとを水酸化ナトリウムやナトリウムメチレート等のアルカリ触媒の存在下、８０〜１８０℃で反応すれば良く、その後、目的物の理論収量に対して水を０．２〜３０．０重量％加え、反応温度８０〜１８０℃で、５〜６０分間攪拌した後、減圧下で余分な水を留出させれば良い。この際、より好ましくは、水の添加量が１．０〜１０．０重量％、反応温度８０〜１２０℃、反応時間１０〜３０分間である。水添加量が、０．２重量％未満の場合は、鹸化反応の十分な効果が得られず、３０．０重量％を超えると余分な水を留出させるのに長時間を要するため好ましくない。反応温度が８０℃未満では鹸化反応の進行が遅くなり、１８０℃を超えると過熱により着色する場合があり好ましくない。また、減圧下で水を留出させる工程は、特に高真空を必要とはせず、脂肪酸メチルエステルとモノアルカノールアミンとの反応時に副生するメタノールを減圧下で除く条件と同程度でよく、例えば水流アスピレーターを用いればよい。
【００２３】
以上述べたように本発明の製造方法により得られた脂肪酸モノアルカノールアミドは、酸性の中和剤を使用しないため、高純度且つ色相がよく、さらに鹸化分解工程および水の留去工程により、未反応の脂肪酸メチルエステルを鹸化分解し、過剰のモノアルカノールアミンも除去できるので、エステル臭およびアミン臭も少ないものである。また、本発明の製造方法は、特殊な装置や高真空を必要としないため、経済的にも優れたものである。
【００２４】
【実施例】
以下実施例により、本発明を詳細に説明する。
【００２５】
実施例１
５００ｍｌのガラス製反応容器に、ラウリン酸メチル２１４．３ｇ（１．０モル）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ラウリン酸モノエタノールアミドを得た。このときの遊離アミン価は９．７、ｐＨは１０．５であった（遊離アミン価，ｐＨはいずれも化粧品原料基準に準じて測定した値）。
【００２６】
反応系を常圧に戻した後、ラウリン酸モノエタノールアミドの理論収量に対して４．０重量％の水９．８ｇを加えて、１００℃で３０分攪拌した。その後、メタノールの除去と同様に水流アスピレーターを使用して、徐々に減圧しながら余分な水を留出させた。このようにして得られたラウリン酸モノエタノールアミドは、遊離アミン価５．５、ｐＨ９．８、酸価０であった。また、生成物の残存水分量は、カールフィッシャー法で、０．１重量％であった。
【００２７】
実施例２
５００ｍｌのガラス製反応容器に、ステアリン酸メチル２９８．５ｇ（１．０モル）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ステアリン酸モノエタノールアミドを得た。このときの遊離アミン価は７．２、ｐＨは１０．４であった。
【００２８】
反応系を常圧に戻した後、ステアリン酸モノエタノールアミドの理論収量に対して１０．０重量％の水３２．９ｇを加えて、１００℃で３０分攪拌した。その後、メタノールの除去と同様に水流アスピレーターを使用して、徐々に減圧しながら余分な水を留出させた。このようにして得られたステアリン酸モノエタノールアミドは、遊離アミン価４．９、ｐＨ９．７、酸価０であった。また、生成物の残存水分量は、カールフィッシャー法で、０．１重量％であった。
【００２９】
実施例３
５００ｍｌのガラス製反応容器に、ヤシ脂肪酸メチルエステル２２６．５ｇ（１．０モル，ＳＶ＝２４７．７より算出）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ヤシ脂肪酸モノエタノールアミドを得た。このときの遊離アミン価は９．０、ｐＨは１０．６であった。
【００３０】
反応系を常圧に戻した後、ヤシ脂肪酸モノエタノールアミドの理論収量に対して２．０重量％の水５．１ｇを加えて、１００℃で３０分攪拌した。その後、メタノールの除去と同様に水流アスピレーターを使用して、徐々に減圧しながら余分な水を留出させた。このようにして得られたヤシ脂肪酸モノエタノールアミドは、遊離アミン価５．２、ｐＨ９．８、酸価０であった。また、生成物の残存水分量は、カールフィッシャー法で、０．１重量％であった。
【００３１】
比較例１
実施例１と同様に、５００ｍｌのガラス製反応容器に、ラウリン酸メチル２１４．３ｇ（１．０モル）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ラウリン酸モノエタノールアミドを得た。このときの遊離アミン価は９．７、ｐＨは１０．５であった。
【００３２】
その後、真空ポンプを使用して、１５０℃，５ｍｍＨｇ以下の条件で３時間減圧して、過剰のモノエタノールアミンを留出させた。その結果、このものは遊離アミン価５．１、ｐＨ１０．２、酸価０であった。
【００３３】
比較例２
実施例１と同様に、５００ｍｌのガラス製反応容器に、ラウリン酸メチル２１４．３ｇ（１．０モル）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ラウリン酸モノエタノールアミドを得た。このときの遊離アミン価は９．７、ｐＨは１０．５であった。
【００３４】
その後、６０％硫酸２．１２ｇ（純分として０．０１３ｍｏｌ）を加え、９０℃で３０分攪拌し、中和した。その結果、このものは遊離アミン価５．２、ｐＨ９．３、酸価０．９であった。
【００３５】
比較例３
実施例１と同様に、５００ｍｌのガラス製反応容器に、ラウリン酸メチル２１４．３ｇ（１．０モル）、モノエタノールアミン６２．９１ｇ（１．０３モル）およびナトリウムメチレート０．７０ｇ（０．０１３モル）を仕込み、１００℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ラウリン酸モノエタノールアミドを得た。このときの遊離アミン価は９．７、ｐＨは１０．５であった。
【００３６】
その後、ラウリン酸２．６０ｇ（純分として０．０１３ｍｏｌ）を加え、９０℃で３０分攪拌し、中和した。その結果、このものの遊離アミン価７．５、ｐＨ９．７、酸価１．３であった。
【００３７】
比較例４
５００ｍｌのガラス製反応容器に、ラウリン酸メチル２１４ｇ（１．０モル）、モノエタノールアミン６１．０８ｇ（１．０モル）およびナトリウムメチレート０．３２ｇ（０．００６モル）を仕込み、１２０℃で３０分攪拌した後、水流アスピレーターを使用して、徐々に減圧しながら副生するメタノールを留出させ、ラウリン酸モノエタノールアミドを得た。このときの遊離アミン価は４．８、ｐＨは１０．３であった。
【００３８】
実施例１〜３と比較例１〜４で得られた脂肪酸モノエタノールアミドの不純物、色相、臭いを比較した結果を表１に示す。
【００３９】
不純物の分析は、ＦＴ−ＩＲチャート上のエステル吸収（１７３０ｃｍ-1付近）の有無を確認した。
【００４０】
色相は、基準油脂試験法のＡＰＨＡ法に準じて測定した。
【００４１】
臭いについては、試料５．０ｇを２００ｍｌ共栓付三角フラスコに入れ、８０℃の温水９５ｇを加え、数分間振とうした後、栓を外してエステル臭，アミン臭の有無を確認した。なお、臭いの試験は、試験者を５人選定し、その結果をまとめたものである。
【００４２】
【表１】
表１に示した結果から明らかなように、本発明方法の実施例１，２，３の場合、不純物のない、色相および臭いの良好な脂肪酸モノアルカノールアミドが得られた。一方、高真空下に過剰のモノエタノールアミンを除去する比較例１の方法では、エステル臭があり、色相も悪いものであった。縮合反応終了後、酸性物質を添加して中和するする比較例２，３の方法では、エステル臭はないものの、アミン臭があり、色相も悪いものであった。また、モノエタノールアミンとアルカリ触媒の量を減らした比較例４の方法では、色相はよいものの、エステル臭が認められた。
【００４４】
【本発明の効果】
本発明の製法を用いた場合、従来の製法の問題点を改良し、エステルアミドを含有せず、且つ色相が良く、臭いの少ない脂肪酸モノアルカノールアミドを経済的に得ることが可能である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for economically producing a fatty acid monoalkanolamide having a sufficiently low content of unreacted raw material and ester amide, good hue and low odor.
[0002]
[Prior art]
Since fatty acid monoalkanolamides have excellent foam stability and thickening action, they are widely used as detergent adjuvants and additives.
[0003]
Conventionally, fatty acid monoalkanolamides are produced by a method in which a fatty acid methyl ester and a monoalkanolamine are reacted in the presence of an alkali catalyst. At that time, in order to suppress the formation of by-products such as unreacted ester and ester amide, the monoalkanolamine is usually excessively added in an amount of 1.01-1.20 mol with respect to 1.0 mol of the fatty acid methyl ester. A method of using and reacting with an alkaline catalyst is generally used.
[0004]
However, in the method using an excess of monoalkanolamine and an alkali catalyst, monoalkanolamine and alkali catalyst remain in the product, resulting in poor purity, hue, odor, etc., and high alkali number. There were drawbacks such as.
[0005]
In order to improve these disadvantages, (1) a method of removing excess monoalkanolamine under high vacuum while heating after completion of the reaction, and (2) an alkali catalyst and excess monoalkanolamine with an acidic substance after completion of the reaction. Several treatment methods such as a neutralization method have been performed.
[0006]
[Problems to be solved by the invention]
However, in order to improve the purity of the product, the method of (1) in which excess monoalkanolamine is removed under high vacuum while heating has a problem that ester amide is formed as a by-product due to a transfer reaction caused by an alkali catalyst. It was.
[0007]
Further, in the method (2) in which the alkali catalyst and excess monoalkanolamine are neutralized with an acidic substance such as sulfuric acid, hydrochloric acid, phosphoric acid, citric acid, lactic acid or lauric acid, the neutralized salts thereof remain, so that the A product in which a pure product could not be obtained and neutralized had a problem that the hue deteriorated due to the effect of the salt produced.
[0008]
Furthermore, a method of reducing the excess of monoalkanolamine with respect to the fatty acid methyl ester and the amount of alkali catalyst used is also conceivable, but this method is difficult to complete, so the smell of unreacted fatty acid ester, ester amide and the like are by-produced. As a result, there were problems such as poor purity.
[0009]
The problem to be solved by the present invention is to improve the problems in the production process of conventional fatty acid monoalkanol amides, economical fatty acid monoalkanols with sufficiently low unreacted raw materials and ester amides, good hue and little odor It is to provide a method for producing an amide.
[0010]
[Means for Solving the Problems]
In order to solve the above-mentioned problems, the present inventors have intensively studied. As a result, in the method of synthesizing a fatty acid monoalkanolamide by reacting a fatty acid methyl ester with a monoalkanolamine in the presence of an alkali catalyst, after completion of the condensation reaction. After adding water and heating, the water was removed under reduced pressure, and it was found that unreacted raw materials and ester amides were sufficiently low in color, good in hue, and less odorous and fatty acid monoalkanol amides could be produced. I came to let you.
[0011]
That is, the present invention relates to the general formula (1)
[0012]
[Chemical 3]
(Wherein R represents a linear or branched alkyl group or alkenyl group having 5 to 21 carbon atoms which may be substituted with a hydroxy group)
For the fatty acid methyl ester represented by general formula (2)
[0014]
[Formula 4]
(Wherein X represents H or CH 3 )
In the method of synthesizing a fatty acid monoalkanolamide by subjecting a monoalkanolamine represented by the following reaction to condensation in the presence of an alkali catalyst, water is added and heated after completion of the condensation reaction, and then water is removed under reduced pressure. The present invention relates to a method for producing a fatty acid monoalkanolamide.
[0016]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the production method of the fatty acid monoalkanolamide of the present invention will be described in detail.
[0017]
In the fatty acid methyl ester of the general formula (1) used in the present invention, R in the formula is a linear or branched alkyl group or alkenyl group having 5 to 21 carbon atoms which may be substituted with a hydroxy group. If it is, it will not specifically limit, The thing of a single composition or a 2 or more types of mixture may be sufficient. Examples of the fatty acid methyl ester represented by the general formula (1) include methyl esters such as lauric acid, myristic acid, stearic acid, 12-hydroxystearic acid, oleic acid, coconut fatty acid, palm fatty acid, and beef tallow fatty acid. Can do.
[0018]
As the monoalkanolamine represented by the general formula (2), either monoethanolamine or isopropanolamine can be selected.
[0019]
Examples of the alkali catalyst used in the production of the fatty acid alkanolamide of the present invention include hydroxides such as sodium hydroxide and potassium hydroxide, alcoholate basic catalysts such as sodium methylate, sodium ethylate and potassium ethylate. Can be mentioned.
[0020]
Fatty acid monoalkanolamides produced by conventional methods include an alkali catalyst and an excess of monoalkanolamine in addition to the desired product. In the conventional technology, neutralization is performed using an acidic substance such as sulfuric acid, hydrochloric acid, phosphoric acid, citric acid, lactic acid, or lauric acid, so that alkali and monoalkanolamine salts remain in the product. Salt was the main cause of coloration.
[0021]
In the present invention, water is added without using an acidic substance, and an unreacted fatty acid methyl ester and the target fatty acid alkanolamide and an alkali catalyst are saponified to be converted into a fatty acid soap and not used in the reaction. In addition, by distilling excess water under reduced pressure, excess monoalkanolamine remaining in the system is distilled simultaneously by the entrainment action, so there is no contamination of salts that cause coloration, the hue is good, It is possible to obtain a product with good odor without ester odor, amine odor and the like.
[0022]
The reaction of the fatty acid methyl ester of the general formula (1) with the monoalkanolamine of the general formula (2) is a conventionally known method, that is, the fatty acid methyl ester and the monoalkanolamine are converted into sodium hydroxide, sodium methylate, etc. The reaction may be carried out at 80 to 180 ° C. in the presence of an alkali catalyst, and then 0.2 to 30.0% by weight of water is added to the theoretical yield of the target product, and the reaction temperature is 80 to 180 ° C. After stirring for 60 minutes, excess water may be distilled off under reduced pressure. In this case, more preferably, the amount of water added is 1.0 to 10.0% by weight, the reaction temperature is 80 to 120 ° C., and the reaction time is 10 to 30 minutes. If the amount of water added is less than 0.2% by weight, a sufficient effect of the saponification reaction cannot be obtained, and if it exceeds 30.0% by weight, it takes a long time to distill excess water, which is not preferable. . If the reaction temperature is less than 80 ° C, the saponification reaction proceeds slowly, and if it exceeds 180 ° C, it may be colored by overheating, which is not preferable. In addition, the process of distilling water under reduced pressure does not require a high vacuum, and may be the same as the conditions under which methanol produced as a by-product during the reaction between fatty acid methyl ester and monoalkanolamine is removed under reduced pressure. For example, a water aspirator may be used.
[0023]
As described above, since the fatty acid monoalkanolamide obtained by the production method of the present invention does not use an acidic neutralizer, it has high purity and good hue. Since the fatty acid methyl ester in the reaction can be saponified and decomposed to remove excess monoalkanolamine, the ester odor and amine odor are also low. Further, the production method of the present invention is economically excellent because it does not require a special apparatus or high vacuum.
[0024]
【Example】
Hereinafter, the present invention will be described in detail by way of examples.
[0025]
Example 1
A 500 ml glass reaction vessel was charged with 214.3 g (1.0 mol) of methyl laurate, 62.91 g (1.03 mol) of monoethanolamine and 0.70 g (0.013 mol) of sodium methylate. After stirring for 30 minutes at 0 ° C., by-product methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain lauric acid monoethanolamide. At this time, the free amine value was 9.7, and the pH was 10.5 (the free amine value and pH were values measured in accordance with cosmetic raw material standards).
[0026]
After returning the reaction system to normal pressure, 9.8 g of water of 4.0% by weight with respect to the theoretical yield of lauric acid monoethanolamide was added and stirred at 100 ° C. for 30 minutes. Thereafter, using a water aspirator in the same manner as the removal of methanol, excess water was distilled while gradually reducing the pressure. The lauric acid monoethanolamide thus obtained had a free amine value of 5.5, a pH of 9.8, and an acid value of 0. The residual water content of the product was 0.1% by weight according to the Karl Fischer method.
[0027]
Example 2
A 500 ml glass reaction vessel was charged with 298.5 g (1.0 mol) of methyl stearate, 62.91 g (1.03 mol) of monoethanolamine and 0.70 g (0.013 mol) of sodium methylate, After stirring for 30 minutes at 0 ° C., by-product methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain stearic acid monoethanolamide. At this time, the free amine value was 7.2, and the pH was 10.4.
[0028]
After returning the reaction system to normal pressure, 32.9 g of 10.0% by weight of water relative to the theoretical yield of stearic acid monoethanolamide was added and stirred at 100 ° C. for 30 minutes. Thereafter, using a water aspirator in the same manner as the removal of methanol, excess water was distilled while gradually reducing the pressure. The stearic acid monoethanolamide thus obtained had a free amine value of 4.9, a pH of 9.7, and an acid value of 0. The residual water content of the product was 0.1% by weight according to the Karl Fischer method.
[0029]
Example 3
In a 500 ml glass reaction vessel, coconut fatty acid methyl ester 226.5 g (1.0 mol, calculated from SV = 247.7), monoethanolamine 62.91 g (1.03 mol) and sodium methylate 0.70 g ( 0.013 mol) was added, and the mixture was stirred at 100 ° C. for 30 minutes, and then by-product methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain palm fatty acid monoethanolamide. At this time, the free amine value was 9.0, and the pH was 10.6.
[0030]
After returning the reaction system to normal pressure, 5.1 g of 2.0% by weight of water relative to the theoretical yield of coconut fatty acid monoethanolamide was added and stirred at 100 ° C. for 30 minutes. Thereafter, using a water aspirator in the same manner as the removal of methanol, excess water was distilled while gradually reducing the pressure. The coconut fatty acid monoethanolamide thus obtained had a free amine value of 5.2, a pH of 9.8, and an acid value of 0. The residual water content of the product was 0.1% by weight according to the Karl Fischer method.
[0031]
Comparative Example 1
In the same manner as in Example 1, in a 500 ml glass reaction vessel, 214.3 g (1.0 mol) of methyl laurate, 62.91 g (1.03 mol) of monoethanolamine and 0.70 g (0. 0 mol) of sodium methylate. 013 mol) was added, and the mixture was stirred at 100 ° C. for 30 minutes, and then by-produced methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain lauric acid monoethanolamide. At this time, the free amine value was 9.7 and the pH was 10.5.
[0032]
Thereafter, using a vacuum pump, the pressure was reduced under conditions of 150 ° C. and 5 mmHg or less for 3 hours to distill excess monoethanolamine. As a result, this product had a free amine value of 5.1, pH of 10.2, and an acid value of 0.
[0033]
Comparative Example 2
In the same manner as in Example 1, in a 500 ml glass reaction vessel, 214.3 g (1.0 mol) of methyl laurate, 62.91 g (1.03 mol) of monoethanolamine and 0.70 g (0. 0 mol) of sodium methylate. 013 mol) was added, and the mixture was stirred at 100 ° C. for 30 minutes, and then by-produced methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain lauric acid monoethanolamide. At this time, the free amine value was 9.7 and the pH was 10.5.
[0034]
Thereafter, 2.12 g of 60% sulfuric acid (0.013 mol as a pure component) was added, and the mixture was stirred at 90 ° C. for 30 minutes for neutralization. As a result, this product had a free amine value of 5.2, a pH of 9.3, and an acid value of 0.9.
[0035]
Comparative Example 3
In the same manner as in Example 1, in a 500 ml glass reaction vessel, 214.3 g (1.0 mol) of methyl laurate, 62.91 g (1.03 mol) of monoethanolamine and 0.70 g (0. 0 mol) of sodium methylate. 013 mol) was added, and the mixture was stirred at 100 ° C. for 30 minutes, and then by-produced methanol was distilled off while gradually reducing the pressure using a water aspirator to obtain lauric acid monoethanolamide. At this time, the free amine value was 9.7 and the pH was 10.5.
[0036]
Thereafter, 2.60 g of lauric acid (0.013 mol as a pure component) was added, and the mixture was stirred at 90 ° C. for 30 minutes for neutralization. As a result, this product had a free amine value of 7.5, a pH of 9.7, and an acid value of 1.3.
[0037]
Comparative Example 4
A 500 ml glass reaction vessel was charged with 214 g (1.0 mol) of methyl laurate, 61.08 g (1.0 mol) of monoethanolamine and 0.32 g (0.006 mol) of sodium methylate at 120 ° C. After stirring for 30 minutes, by-product methanol was distilled off using a water aspirator while gradually reducing the pressure to obtain lauric acid monoethanolamide. At this time, the free amine value was 4.8 and the pH was 10.3.
[0038]
Table 1 shows the results of comparing the impurities, hue, and odor of the fatty acid monoethanolamide obtained in Examples 1 to 3 and Comparative Examples 1 to 4.
[0039]
The analysis of impurities confirmed the presence or absence of ester absorption (around 1730 cm −1 ) on the FT-IR chart.
[0040]
The hue was measured according to the APHA method of the standard fat test method.
[0041]
For odor, 5.0 g of a sample was placed in a 200 ml conical flask with a stopper, and 95 g of warm water at 80 ° C. was added and shaken for several minutes. The stopper was removed and the presence of ester odor and amine odor was confirmed. In the odor test, five testers were selected and the results were summarized.
[0042]
[Table 1]
As is clear from the results shown in Table 1, in the case of Examples 1, 2, and 3 of the method of the present invention, fatty acid monoalkanolamides free from impurities and having good hue and odor were obtained. On the other hand, in the method of Comparative Example 1 in which excess monoethanolamine was removed under high vacuum, there was an ester odor and the hue was poor. In the methods of Comparative Examples 2 and 3, in which an acidic substance was added and neutralized after completion of the condensation reaction, although there was no ester odor, there was an amine odor and a poor hue. Further, in the method of Comparative Example 4 in which the amounts of monoethanolamine and alkali catalyst were reduced, although the hue was good, an ester odor was recognized.
[0044]
[Effect of the present invention]
When the production method of the present invention is used, it is possible to improve the problems of the conventional production method and economically obtain a fatty acid monoalkanolamide that does not contain ester amide, has a good hue, and has a low odor.
Claims (3)
で示される脂肪酸メチルエステルに対し、一般式（２）
で示されるモノアルカノールアミンをアルカリ触媒の存在下で縮合反応させ脂肪酸モノアルカノールアミドを製造する方法において、縮合反応終了後水を加えて加熱した後、減圧下で水を除去することを特徴とする脂肪酸モノアルカノールアミドの製造方法。General formula (1)
For the fatty acid methyl ester represented by general formula (2)
In the method for producing a fatty acid monoalkanol amide by subjecting the monoalkanolamine represented by the formula to a condensation reaction in the presence of an alkali catalyst, water is added after the condensation reaction is completed, and then water is removed under reduced pressure. Method for producing fatty acid monoalkanolamide.
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