JP2003183232A - Method for producing higher fatty acid alkanolamide - Google Patents
Method for producing higher fatty acid alkanolamideInfo
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- JP2003183232A JP2003183232A JP2001390832A JP2001390832A JP2003183232A JP 2003183232 A JP2003183232 A JP 2003183232A JP 2001390832 A JP2001390832 A JP 2001390832A JP 2001390832 A JP2001390832 A JP 2001390832A JP 2003183232 A JP2003183232 A JP 2003183232A
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- fatty acid
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、匂いを改善し、更
に速泡性も良好な高級脂肪酸アルカノールアミドの製造
法に関する。TECHNICAL FIELD The present invention relates to a process for producing a higher fatty acid alkanolamide having improved odor and good foaming property.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】高級脂
肪酸アルカノールアミドは、洗浄剤や香粧品の成分とし
て広く用いられている基剤である。こうした洗浄剤や香
粧品は人体に直接付着する機会が多いことから、配合成
分自体の匂いの善し悪しが製品価値を左右することも多
く、十分に匂いの良好な成分を配合することが不可欠で
ある。BACKGROUND OF THE INVENTION Higher fatty acid alkanolamides are bases widely used as ingredients for detergents and cosmetics. Since these detergents and cosmetics often come into direct contact with the human body, the odor of the ingredients themselves often affects the product value, and it is essential to incorporate ingredients with a sufficiently good odor. .
【０００３】アルカノールアミドは一般に、脂肪酸又は
脂肪酸エステルとアルカノールアミンを縮合することに
よって製造されている。この際、製品の匂いに影響を与
える因子として、微量に存在する未反応のアルカノール
アミンによるアミン臭が挙げられる。このアミン臭は反
応終了時に水蒸気蒸留等により、系内のアミン量を低減
することによって改善する技術が広く知られている。Alkanolamides are generally produced by condensing fatty acids or fatty acid esters with alkanolamines. At this time, as a factor that affects the odor of the product, there is an amine odor due to an unreacted alkanolamine present in a trace amount. A technique for improving this amine odor by reducing the amount of amine in the system by steam distillation at the end of the reaction is widely known.
【０００４】また一般に高級脂肪酸アルカノールアミド
を製造する際に、触媒としてナトリウムアルコラート等
の塩基性触媒を用いることが多い。この塩基性成分は水
蒸気蒸留による処理でも除去されず、製品中に残存する
ことにより経時保存による匂いの劣化を引き起こす原因
となる。In general, a basic catalyst such as sodium alcoholate is often used as a catalyst when producing higher fatty acid alkanolamides. This basic component is not removed even by the treatment by steam distillation, and remains in the product to cause deterioration of odor due to storage over time.
【０００５】本発明の課題は、上記のような欠点がな
く、匂いが改善され、更に速泡性に問題がない高級脂肪
酸アルカノールアミドの製造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 higher fatty acid alkanolamide which does not have the above-mentioned drawbacks, has an improved odor, and has no problem in the quick foaming property.
【０００６】[0006]
【課題を解決するための手段】本発明は、一般式（１）
Ｒ1−ＣＯＯＨ （１）
（式中、Ｒ1は炭素数５〜２１の直鎖もしくは分岐鎖の
アルキル基、アルケニル基又はヒドロキシアルキル基を
示す。）で表される脂肪酸、あるいはこの脂肪酸のエス
テルと、一般式（２）The present invention provides a compound represented by the general formula (1) R 1 —COOH (1) (wherein R 1 is a linear or branched alkyl group having 5 to 21 carbon atoms, an alkenyl group, or A hydroxyalkyl group), or an ester of this fatty acid, and a general formula (2)
【０００７】[0007]
【化３】 [Chemical 3]
【０００８】（式中、Ｒ2は水素原子、ヒドロキシエチ
ル基、又は炭素数１〜８の直鎖もしくは分岐鎖のアルキ
ル基を示す。Ｒ3は炭素数１〜６の直鎖もしくは分岐鎖
のアルキレン基を示す。）で表されるアルカノールアミ
ンとを反応させた後、減圧下で処理する、一般式（３）(In the formula, R 2 represents a hydrogen atom, a hydroxyethyl group, or a linear or branched alkyl group having 1 to 8 carbon atoms. R 3 represents a linear or branched chain having 1 to 6 carbon atoms. An alkylene group is shown), and then treated under reduced pressure, the general formula (3)
【０００９】[0009]
【化４】 [Chemical 4]
【００１０】（式中、Ｒ1，Ｒ2及びＲ3は上記と同じ意
味を示す。）で表される高級脂肪酸アルカノールアミド
の製造法である。A method for producing a higher fatty acid alkanolamide represented by the formula (wherein R 1 , R 2 and R 3 have the same meanings as described above).
【００１１】[0011]
【発明の実施の形態】本発明に用いられる一般式（１）
で表される脂肪酸としては、直鎖又は分岐鎖をもつ炭素
数６〜２２の高級脂肪酸から選ばれる１種以上が挙げら
れる。具体的にはカプロン酸、カプリル酸、カプリン
酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステア
リン酸、イソステアリン酸、オレイン酸、ノナデカン
酸、ベヘニン酸、エルカ酸、１２−ヒドロキシステアリ
ン酸や、ヤシ油脂肪酸、綿実油脂肪酸、トウモロコシ油
脂肪酸、牛脂脂肪酸、ババス脂肪酸、パーム核油脂肪
酸、大豆油脂肪酸、あまに油脂肪酸、ひまし油脂肪酸、
オリーブ油脂肪酸、鯨油脂肪酸等の植物油又は動物油脂
肪酸が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION General formula (1) used in the present invention
Examples of the fatty acid represented by are one or more kinds selected from higher fatty acids having a linear or branched chain and having 6 to 22 carbon atoms. Specifically, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, nonadecanoic acid, behenic acid, erucic acid, 12-hydroxystearic acid and coconut oil fatty acid. , Cottonseed oil fatty acid, corn oil fatty acid, beef tallow fatty acid, babassu fatty acid, palm kernel oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, castor oil fatty acid,
Vegetable oils such as olive oil fatty acids and whale oil fatty acids, or animal oil fatty acids may be mentioned.
【００１２】また脂肪酸エステルとしては、上記高級脂
肪酸のメチルエステル、エチルエステル、プロピルエス
テル等の炭素数１〜６のアルキルエステル、あるいは上
記高級脂肪酸のモノ、ジ又はトリグリセライドやこれら
の混合物が挙げられる。Examples of the fatty acid ester include alkyl esters having 1 to 6 carbon atoms such as methyl ester, ethyl ester and propyl ester of the above-mentioned higher fatty acids, mono-, di- or triglycerides of the above-mentioned higher fatty acids, and mixtures thereof.
【００１３】好ましくはカプリル酸、カプリン酸、ラウ
リン酸、ミリスチン酸、パルミチン酸、ステアリン酸、
イソステアリン酸、オレイン酸、ヤシ油脂肪酸、パーム
核油脂肪酸、あるいはそれらのメチルエステル、エチル
エステル、プロピルエステル、トリグリセライド（油
脂）であり、特に好ましくはメチルエステルあるいは油
脂である。Preferably, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid,
Isostearic acid, oleic acid, coconut oil fatty acid, palm kernel oil fatty acid, or their methyl esters, ethyl esters, propyl esters, triglycerides (fats and oils), and particularly preferred are methyl esters and fats and oils.
【００１４】本発明に用いられる一般式（２）で表され
るアルカノールアミンにおいて、Ｒ 2としては水素原
子、ヒドロキシエチル基、メチル基、エチル基、プロピ
ル基、イソプロピル基、ブチル基、イソブチル基、tert
−ブチル基、ヘキシル基、２−エチルヘキシル基等が挙
げられ、炭素数１〜８、特に炭素数１〜３の直鎖もしく
は分岐鎖のアルキル基が好ましい。Ｒ3としてはメチレ
ン基、エチレン基、プロピレン基、イソプロピレン基、
ブチレン基、イソブチレン基、へキシレン基等が挙げら
れ、炭素数１〜３の直鎖もしくは分岐鎖のアルキレン基
が好ましい。It is represented by the general formula (2) used in the present invention.
Alkanolamine 2As a hydrogen source
Child, hydroxyethyl group, methyl group, ethyl group, propyl group
Group, isopropyl group, butyl group, isobutyl group, tert
-Butyl group, hexyl group, 2-ethylhexyl group, etc.
C1-8, especially C1-C3 straight chain
Is preferably a branched chain alkyl group. R3As a wallet
Group, ethylene group, propylene group, isopropylene group,
Butylene group, isobutylene group, hexylene group, etc.
A linear or branched alkylene group having 1 to 3 carbon atoms
Is preferred.
【００１５】一般式（２）で表されるアルカノールアミ
ンの具体例として、モノエタノールアミン、ジエタノー
ルアミン、イソプロパノールアミン、Ｎ−メチルエタノ
ールアミン、Ｎ−メチルイソプロパノールアミン、Ｎ−
エチルエタノールアミン、Ｎ−エチルブタノールアミン
等があり、好ましくはモノエタノールアミン、ジエタノ
ールアミン、イソプロパノールアミン、Ｎ−メチルエタ
ノールアミン、Ｎ−メチルイソプロパノールアミンであ
り、特に好ましくはＮ−メチルエタノールアミン、Ｎ−
メチルイソプロパノールアミンである。Specific examples of the alkanolamine represented by the general formula (2) include monoethanolamine, diethanolamine, isopropanolamine, N-methylethanolamine, N-methylisopropanolamine and N-.
There are ethylethanolamine, N-ethylbutanolamine and the like, preferably monoethanolamine, diethanolamine, isopropanolamine, N-methylethanolamine and N-methylisopropanolamine, particularly preferably N-methylethanolamine and N-
It is methylisopropanolamine.
【００１６】一般式（１）で表される脂肪酸又はそのエ
ステルと一般式（２）で表されるアルカノールアミンと
の反応は、特に限定されるものではないが、広く知られ
ている方法で反応を行って良い。例えば、脂肪酸とアル
カノールアミンとの反応では、双方を同時に仕込み高温
下で脱水縮合を行う方法や、高温下において脂肪酸中に
アルカノールアミンを滴下して反応させる方法等があ
る。また、脂肪酸エステルを用いた反応においては、ア
ルカリ触媒存在下、８０〜１２０℃でアルカノールアミ
ンと反応させることにより、容易に目的とするアルカノ
ールアミドが得られる。ここで用いられるアルカリ触媒
としては、ナトリウムメチラート等のナトリウムアルコ
ラートが挙げられる。脂肪酸又はそのエステルとアルカ
ノールアミンとは、脂肪酸又はそのエステルに対し、ア
ルカノールアミン０．７〜３当量倍、特に０．９５〜
１．３当量倍で反応させることが好ましい。The reaction between the fatty acid represented by the general formula (1) or its ester and the alkanolamine represented by the general formula (2) is not particularly limited, but the reaction is carried out by a widely known method. Good to go. For example, in the reaction of a fatty acid and an alkanolamine, there are a method of charging both of them at the same time to carry out dehydration condensation at a high temperature, a method of dropping an alkanolamine into a fatty acid at a high temperature and causing a reaction. In the reaction using a fatty acid ester, the desired alkanolamide can be easily obtained by reacting with an alkanolamine in the presence of an alkali catalyst at 80 to 120 ° C. Examples of the alkali catalyst used here include sodium alcoholates such as sodium methylate. The fatty acid or its ester and the alkanolamine are alkanolamine 0.7 to 3 equivalent times, especially 0.95 to the fatty acid or its ester.
It is preferable to react with 1.3 equivalent times.
【００１７】本発明においては、一般式（１）で表され
る脂肪酸、あるいはこの脂肪酸のエステルと、一般式
（２）で表されるアルカノールアミンとを反応させた後
に、減圧下で処理する。減圧処理時の圧力は、０．６〜
２６．６kPaが好ましく、０．６〜１３．３kPaが更に好
ましく、１．３３〜６．６kPaが特に好ましい。また、
減圧処理中は温度を制御して行うことも有効である。好
ましい温度は、反応効率と劣化の問題回避の観点から、
４０〜２００℃、更に６０〜１５０℃、特に８０〜１２
０℃である。減圧処理条件の組合せの一例としては、圧
力０．６〜２６．６kPa、温度４０〜２００℃の条件が
好ましく、圧力０．６〜１３．３kPa、温度６０〜１５
０℃の条件が更に好ましく、圧力１．３３〜６．６kP
a、温度８０〜１２０℃の条件が特に好ましい。In the present invention, the fatty acid represented by the general formula (1) or the ester of this fatty acid is reacted with the alkanolamine represented by the general formula (2) and then treated under reduced pressure. The pressure during depressurization is 0.6-
26.6 kPa is preferable, 0.6 to 13.3 kPa is more preferable, and 1.33 to 6.6 kPa is particularly preferable. Also,
It is also effective to control the temperature during the depressurization process. The preferred temperature is from the viewpoint of reaction efficiency and avoidance of deterioration problems.
40 to 200 ° C., further 60 to 150 ° C., especially 80 to 12
It is 0 ° C. As an example of a combination of depressurization treatment conditions, a pressure of 0.6 to 26.6 kPa and a temperature of 40 to 200 ° C. are preferable, and a pressure of 0.6 to 13.3 kPa and a temperature of 60 to 15
The condition of 0 ° C is more preferable, and the pressure is 1.33 to 6.6 kP.
The conditions of a and the temperature of 80 to 120 ° C. are particularly preferable.
【００１８】また、減圧処理時に、水蒸気、及び／又は
窒素、ヘリウム、アルゴン等の不活性ガスを接触させる
ことが好ましく、更に水蒸気又は窒素、特に水蒸気を接
触させることが好ましい。不活性ガス及び／又は水蒸気
を吹き込む量は特に限定されるものではなく、要求され
る品質に応じて任意に選択できる。Further, it is preferable to contact steam and / or an inert gas such as nitrogen, helium, or argon during the pressure reduction treatment, and further preferably contact steam or nitrogen, particularly steam. The amount of the inert gas and / or steam blown in is not particularly limited, and can be arbitrarily selected according to the required quality.
【００１９】更に本発明においては、減圧下での処理前
に水の添加処理を行うことが好ましい。水の添加量は、
総仕込量に対し、０．１〜２０重量％が好ましく、０．
３〜１０重量％が更に好ましい。水の添加処理は、温度
６０〜１２０℃で、撹拌及び／又は還流処理を行うこと
が好ましく、撹拌と還流の両方を行うのが更に好まし
い。Further, in the present invention, it is preferable to add water before the treatment under reduced pressure. The amount of water added is
0.1 to 20% by weight is preferable with respect to the total amount charged, and 0.
3 to 10% by weight is more preferable. The water addition treatment is preferably carried out by stirring and / or refluxing at a temperature of 60 to 120 ° C., and more preferably both stirring and refluxing are carried out.
【００２０】尚、上記のような処理を行った後、必要と
すれば、さらに通常の精製工程、例えば蒸留、抽出、晶
析、クロマト処理工程等により精製を行ってよいことは
いうまでもない。Needless to say, after the above-mentioned treatment, if necessary, further purification may be carried out by usual purification steps such as distillation, extraction, crystallization, and chromatographic treatment steps. .
【００２１】[0021]
【実施例】例中の％は、特記しない限り重量％である。EXAMPLES In the examples,% is weight% unless otherwise specified.
【００２２】実施例１
１リットルの反応容器にパーム核油500.0g（0.72モ
ル）、Ｎ−メチルエタノールアミン168.8g（2.25モル）
及び28％ナトリウムメチラート8.39g（純分として0.044
モル）を仕込み、90℃で３時間反応させた。その後150
℃に昇温し30分間で圧力を1.3kPaまで減圧にし、この状
態で２時間保ち、過剰のＮ−メチルエタノールアミンを
除去し、パーム核油脂肪酸Ｎ−メチルエタノールアミド
を得た。Example 1 Palm kernel oil 500.0 g (0.72 mol) and N-methylethanolamine 168.8 g (2.25 mol) in a 1 liter reaction vessel.
And 28% sodium methylate 8.39 g (0.044% pure)
(Mol) and charged at 90 ° C. for 3 hours. Then 150
The temperature was raised to 0 ° C. and the pressure was reduced to 1.3 kPa in 30 minutes, and this state was maintained for 2 hours to remove excess N-methylethanolamine to obtain palm kernel oil fatty acid N-methylethanolamide.
【００２３】実施例２
実施例１と同様にパーム核油とＮ−メチルエタノールア
ミンを90℃で３時間反応させた後、100℃に昇温し、30
分間で圧力を1.3kPaまで減圧にし、この状態で水蒸気を
７ｇ／Hrの割合で２時間吹き込み、過剰のＮ−メチルエ
タノールアミンを除去し、パーム核油脂肪酸Ｎ−メチル
エタノールアミドを得た。Example 2 Palm kernel oil and N-methylethanolamine were reacted at 90 ° C. for 3 hours in the same manner as in Example 1 and then heated to 100 ° C.
The pressure was reduced to 1.3 kPa per minute, and in this state, steam was blown at a rate of 7 g / hr for 2 hours to remove excess N-methylethanolamine to obtain palm kernel oil fatty acid N-methylethanolamide.
【００２４】実施例３
水蒸気の代わりに、窒素を０．７Ｌ／Hr（常圧換算）の
割合で２時間吹き込む以外は実施例２と同様にして、パ
ーム核油脂肪酸Ｎ−メチルエタノールアミドを得た。Example 3 Palm kernel oil fatty acid N-methylethanolamide was obtained in the same manner as in Example 2 except that nitrogen was blown in at a rate of 0.7 L / Hr (normal pressure conversion) for 2 hours instead of steam. It was
【００２５】実施例４
実施例１と同様にパーム核油とＮ−メチルエタノールア
ミンを90℃で３時間反応させた後、反応生成物に水を4.
7g加え95℃で30分間撹拌処理を行った。その後、100℃
に昇温し、30分間で圧力を1.3kPaまで減圧にし、この状
態で水蒸気を７ｇ／Hrの割合で２時間吹き込み、過剰の
Ｎ−メチルエタノールアミンと余分な水を除去し、パー
ム核油脂肪酸Ｎ−メチルエタノールアミドを得た。Example 4 Palm kernel oil and N-methylethanolamine were reacted at 90 ° C. for 3 hours in the same manner as in Example 1, and water was added to the reaction product as 4.
7 g was added and the mixture was stirred at 95 ° C for 30 minutes. After that, 100 ℃
Then, the pressure is reduced to 1.3 kPa in 30 minutes, and steam is blown in this state at a rate of 7 g / Hr for 2 hours to remove excess N-methylethanolamine and excess water. N-methyl ethanolamide was obtained.
【００２６】実施例５
実施例１と同様にパーム核油とＮ−メチルエタノールア
ミンを90℃で３時間反応させた後、反応生成物に水を4.
7g加え95℃で30分間撹拌処理を行った。その後、150℃
に昇温し、30分間で圧力を6.6kPaまで減圧にし、この状
態で水蒸気を７ｇ／Hrの割合で２時間吹き込み、過剰の
Ｎ−メチルエタノールアミンと余分な水を除去し、パー
ム核油脂肪酸Ｎ−メチルエタノールアミドを得た。Example 5 Palm kernel oil and N-methylethanolamine were reacted at 90 ° C. for 3 hours in the same manner as in Example 1, and water was added to the reaction product as 4.
7 g was added and the mixture was stirred at 95 ° C for 30 minutes. After that, 150 ℃
Then, the pressure was reduced to 6.6 kPa in 30 minutes, and in this state, steam was blown at a rate of 7 g / Hr for 2 hours to remove excess N-methylethanolamine and excess water. N-methyl ethanolamide was obtained.
【００２７】実施例６
実施例１と同様にパーム核油とＮ−メチルエタノールア
ミンを90℃で３時間反応させた後、反応生成物に水を4.
7g加え95℃で30分間撹拌処理を行った。その後、80℃に
温度を下げた後、30分間で圧力を1.3kPaまで減圧にし、
この状態で水蒸気を７ｇ／Hrの割合で３時間吹き込み、
過剰のＮ−メチルエタノールアミンと余分な水を除去
し、パーム核油脂肪酸Ｎ−メチルエタノールアミドを得
た。Example 6 Palm kernel oil and N-methylethanolamine were reacted at 90 ° C. for 3 hours in the same manner as in Example 1, and water was added to the reaction product as 4.
7 g was added and the mixture was stirred at 95 ° C for 30 minutes. Then, after lowering the temperature to 80 ° C, the pressure was reduced to 1.3 kPa in 30 minutes,
In this state, steam is blown at a rate of 7 g / Hr for 3 hours,
Excess N-methylethanolamine and excess water were removed to obtain palm kernel oil fatty acid N-methylethanolamide.
【００２８】実施例７
１リットルの反応容器にパーム核油脂肪酸メチルエステ
ル500.0g（2.157モル）、Ｎ−メチルエタノールアミン1
70.9g（2.275モル）及び28％ナトリウムメチラート5.35
g（純分として0.027モル）を仕込み、90℃で３時間反応
反応させた後、反応生成物に水を3.0g加え95℃で30分間
撹拌処理を行った。その後、実施例４と同様に減圧下で
の水蒸気の吹き込み及びその後の除去を行い、パーム核
油脂肪酸Ｎ−メチルエタノールアミドを得た。Example 7 500.0 g (2.157 mol) of palm kernel oil fatty acid methyl ester and 1 N-methylethanolamine in a 1 liter reaction vessel.
70.9 g (2.275 mol) and 28% sodium methylate 5.35
After charging g (0.027 mol as a pure content) and reacting at 90 ° C. for 3 hours, 3.0 g of water was added to the reaction product and stirred at 95 ° C. for 30 minutes. Then, in the same manner as in Example 4, the steam was blown under reduced pressure and then removed to obtain palm kernel oil fatty acid N-methylethanolamide.
【００２９】実施例８
１リットルの反応容器にヤシ油451.3g（0.605モル）、
Ｎ−メチルエタノールアミン158.8g（1.874モル）及び2
8％ナトリウムメチラート7.89g（純分として0.036モ
ル）を仕込み、90℃で３時間反応させた後、反応生成物
に水を4.4g加え95℃で30分間処理を行った。その後、実
施例４と同様に減圧下での水蒸気の吹き込み及びその後
の除去を行い、ヤシ油脂肪酸Ｎ−メチルエタノールアミ
ドを得た。Example 8 451.3 g (0.605 mol) of coconut oil in a 1-liter reaction vessel,
N-methylethanolamine 158.8 g (1.874 mol) and 2
After adding 7.89 g of 8% sodium methylate (0.036 mol as pure content) and reacting at 90 ° C. for 3 hours, 4.4 g of water was added to the reaction product and treated at 95 ° C. for 30 minutes. Then, in the same manner as in Example 4, the steam was blown under reduced pressure and then removed to obtain coconut oil fatty acid N-methylethanolamide.
【００３０】実施例９
１リットルの反応容器にヤシ油脂肪酸メチルエステル40
0g（1.823モル）、Ｎ−メチルエタノールアミン143.7g
（1.914モル）及び28％ナトリウムメチラート7.03g（純
分として0.036モル）を仕込み、90℃で３時間反応させ
た後、反応生成物に水を3.94g加え95℃で30分間処理を
行った。その後、実施例４と同様に減圧下での水蒸気の
吹き込み及びその後の除去を行い、ヤシ油脂肪酸Ｎ−メ
チルエタノールアミドを得た。Example 9 Palm oil fatty acid methyl ester 40 in a 1 liter reaction vessel
0g (1.823mol), N-methylethanolamine 143.7g
(1.914 mol) and 28% sodium methylate 7.03 g (0.036 mol as pure content) were charged and reacted at 90 ° C. for 3 hours, then 3.94 g of water was added to the reaction product and treated at 95 ° C. for 30 minutes. . Then, in the same manner as in Example 4, the steam was blown under reduced pressure and then removed to obtain coconut oil fatty acid N-methylethanolamide.
【００３１】実施例１０
２リットルの反応容器にラウリン酸メチル1200.0g（5.6
1モル）、Ｎ−メチルエタノールアミン442.0（5.89モ
ル）及び28％ナトリウムメチラート21.6g（純分として
0.112モル）を仕込み、90℃で３時間反応させた後、反
応生成物に水を12.0g加え95℃で30分間撹拌処理を行っ
た。その後、実施例４と同様に減圧下での水蒸気の吹き
込み及びその後の除去を行い、ラウリン酸Ｎ−メチルエ
タノールアミドを得た。Example 10 1200.0 g (5.6%) of methyl laurate was placed in a 2-liter reaction vessel.
1 mol), N-methylethanolamine 442.0 (5.89 mol) and 28% sodium methylate 21.6 g (as pure content)
0.112 mol) was charged and reacted at 90 ° C. for 3 hours, 12.0 g of water was added to the reaction product, and the mixture was stirred at 95 ° C. for 30 minutes. After that, steam was blown under reduced pressure and then removed in the same manner as in Example 4 to obtain lauric acid N-methylethanolamide.
【００３２】実施例１１
１リットルの反応容器にラウリン酸メチル400.0g（1.86
9モル）、Ｎ−メチルエタノールアミン147.4g（1.963モ
ル）及び28％ナトリウムメチラート7.21g（純分として
0.037モル）を仕込み、90℃で３時間反応させた後、100
℃に昇温し30分間で圧力を1.3kPaまで減圧にし、この状
態で水蒸気を５ｇ／Hrの割合で２時間吹き込み、過剰の
Ｎ−メチルエタノールアミンを除去し、ラウリン酸Ｎ−
メチルエタノールアミドを得た。Example 11 400.0 g (1.86) of methyl laurate was placed in a 1 liter reaction vessel.
9 mol), 147.4 g (1.963 mol) of N-methylethanolamine and 7.21 g of 28% sodium methylate (as pure content)
(0.037 mol), and react at 90 ° C for 3 hours, then add 100
The temperature was raised to ℃ and the pressure was reduced to 1.3 kPa in 30 minutes. In this state, steam was blown at a rate of 5 g / Hr for 2 hours to remove excess N-methylethanolamine and to remove lauric acid N-
Methyl ethanolamide was obtained.
【００３３】比較例１
１リットルの反応容器にパーム核油500.0g（0.72モ
ル）、Ｎ−メチルエタノールアミン168.8g（2.25モル）
及び28％ナトリウムメチラート8.39g（純分として0.044
モル）を仕込み、90℃で３時間反応させて、パーム核油
脂肪酸Ｎ−メチルエタノールアミドを得た。Comparative Example 1 Palm kernel oil 500.0 g (0.72 mol) and N-methylethanolamine 168.8 g (2.25 mol) in a 1 liter reaction vessel.
And 28% sodium methylate 8.39 g (0.044% pure)
Mol) and charged at 90 ° C. for 3 hours to obtain palm kernel oil fatty acid N-methylethanolamide.
【００３４】比較例２
１リットルの反応容器にパーム核油脂肪酸メチルエステ
ル500.0g（2.157モル）、Ｎ−メチルエタノールアミン1
70.9g（2.275モル）及び28％ナトリウムメチラート5.35
g（純分として0.027モル）を仕込み、90℃で３時間反応
させて、パーム核油脂肪酸Ｎ−メチルエタノールアミド
を得た。Comparative Example 2 500.0 g (2.157 mol) of palm kernel oil fatty acid methyl ester and 1 N-methylethanolamine in a 1 liter reaction vessel.
70.9 g (2.275 mol) and 28% sodium methylate 5.35
g (0.027 mol as pure content) was charged and reacted at 90 ° C. for 3 hours to obtain palm kernel oil fatty acid N-methylethanolamide.
【００３５】比較例３
１リットルの反応容器にヤシ油451.3g（0.605モル）、
Ｎ−メチルエタノールアミン158.8g（1.874モル）及び2
8％ナトリウムメチラート7.89g（純分として0.036モ
ル）を仕込み、90℃で３時間反応させて、ヤシ油脂肪酸
Ｎ−メチルエタノールアミドを得た。Comparative Example 3 451.3 g (0.605 mol) of coconut oil in a 1 liter reaction vessel,
N-methylethanolamine 158.8 g (1.874 mol) and 2
7.89 g (0.036 mol as a pure content) of 8% sodium methylate was charged and reacted at 90 ° C. for 3 hours to obtain a coconut oil fatty acid N-methylethanolamide.
【００３６】比較例４
１リットルの反応容器にヤシ油脂肪酸メチルエステル40
0.0g（1.823モル）、Ｎ−メチルエタノールアミン143.7
g（1.914モル）及び28％ナトリウムメチラート7.03g
（純分として0.036モル）を仕込み、90℃で３時間反応
させて、ヤシ油脂肪酸Ｎ−メチルエタノールアミドを得
た。Comparative Example 4 Coconut oil fatty acid methyl ester 40 was placed in a 1 liter reaction vessel.
0.0g (1.823mol), N-methylethanolamine 143.7
g (1.914 mol) and 28% sodium methylate 7.03 g
(0.036 mol as pure content) was charged and reacted at 90 ° C. for 3 hours to obtain coconut oil fatty acid N-methylethanolamide.
【００３７】比較例５
１リットルの反応容器にラウリン酸メチル400.0g（1.86
9モル）、Ｎ−メチルエタノールアミン147.4g（1.963モ
ル）及び28％ナトリウムメチラート7.21g（純分として
0.037モル）を仕込み、90℃で３時間反応させて、ラウ
リン酸Ｎ−メチルエタノールアミドを得た。Comparative Example 5 400.0 g (1.86) of methyl laurate was placed in a 1 liter reaction vessel.
9 mol), 147.4 g (1.963 mol) of N-methylethanolamine and 7.21 g of 28% sodium methylate (as pure content)
0.037 mol) was charged and reacted at 90 ° C for 3 hours to obtain lauric acid N-methylethanolamide.
【００３８】試験例
実施例１〜１１及び比較例１〜５で得られた脂肪酸アル
カノールアミドについて、下記方法で匂い及び速泡性を
評価した。結果を表１に示す。Test Example The fatty acid alkanolamides obtained in Examples 1 to 11 and Comparative Examples 1 to 5 were evaluated for odor and quick foaming property by the following methods. The results are shown in Table 1.
【００３９】＜匂い評価法＞試料20.0gを50ミリリット
ルの共栓付三角フラスコに入れ、数分間振とうした後、
栓を外して下記基準で匂いを評価した。
５：全く匂いがない
４：ほとんど匂いがない
３：弱い異臭がする
２：異臭がする
１：強い異臭がする。<Odor evaluation method> 20.0 g of the sample was put in a 50 ml Erlenmeyer flask with a ground stopper, and after shaking for several minutes,
The stopper was removed and the odor was evaluated according to the following criteria. 5: No odor 4: Almost no odor 3: Weak offensive 2: Offensive 1: Strong offensive odor.
【００４０】＜速泡性の評価法＞ポリオキシエチレン
（EO=２．０）ラウリルエーテル硫酸Naと試料を、重量
比17対３の割合に調製した組成物をイオン交換水で20倍
に希釈し水溶液30mLを調製した。この水溶液を内径３cm
の300mL活栓付メスシリンダーに入れ、25℃、10秒間、
振幅10cmで20回振とうした直後の泡量（mL）を測定し
た。<Evaluation method for quick foaming property> Polyoxyethylene (EO = 2.0) Na lauryl ether sulfate and a sample were prepared at a weight ratio of 17: 3, and the composition was diluted 20 times with ion-exchanged water. Then, 30 mL of an aqueous solution was prepared. This aqueous solution has an inner diameter of 3 cm
Put in a graduated cylinder with a 300 mL stopcock at 25 ° C for 10 seconds,
The amount of foam (mL) immediately after shaking 20 times with an amplitude of 10 cm was measured.
【００４１】[0041]
【表１】 [Table 1]
【００４２】[0042]
【発明の効果】本発明によれば、簡単な操作で、しかも
経済的に、匂いが改善され、更に速泡性に問題がない高
級脂肪酸アルカノールアミドを製造することができ、本
発明によって得られる高級脂肪酸アルカノールアミド
は、経時保存においても匂いの劣化がなく、後処理せず
に香粧品等の製品に応用できる。EFFECTS OF THE INVENTION According to the present invention, a higher fatty acid alkanolamide having an improved odor and having no problem in quick foaming can be produced by a simple operation, economically, and is obtained by the present invention. The higher fatty acid alkanolamide has no odor deterioration even after storage over time, and can be applied to products such as cosmetics without post-treatment.
フロントページの続き (72)発明者 坂井 隆也 和歌山県和歌山市湊1334 花王株式会社研 究所内 (72)発明者 飯高 一弘 和歌山県和歌山市湊1334 花王株式会社研 究所内 (72)発明者 金子 洋平 和歌山県和歌山市湊1334 花王株式会社研 究所内 Ｆターム(参考） 4H006 AA02 AC53 AD14 BA02 BA45 BA69 BB19 BC10 BC11 BC30 BC31 BE60 BN10 BV34 4H039 CA71 CD40 Continued front page (72) Inventor Takaya Sakai Kao Co., Ltd. 1334 Minato, Wakayama City, Wakayama Prefecture Inside the laboratory (72) Inventor Kazuhiro Iidaka Kao Co., Ltd. 1334 Minato, Wakayama City, Wakayama Prefecture Inside the laboratory (72) Inventor Yohei Kaneko Kao Co., Ltd. 1334 Minato, Wakayama City, Wakayama Prefecture Inside the laboratory F-term (reference) 4H006 AA02 AC53 AD14 BA02 BA45 BA69 BB19 BC10 BC11 BC30 BC31 BE60 BN10 BV34 4H039 CA71 CD40
Claims (6)
アルキル基、アルケニル基又はヒドロキシアルキル基を
示す。）で表される脂肪酸、あるいはこの脂肪酸のエス
テルと、一般式（２） 【化１】 （式中、Ｒ2は水素原子、ヒドロキシエチル基、又は炭
素数１〜８の直鎖もしくは分岐鎖のアルキル基を示す。
Ｒ3は炭素数１〜６の直鎖もしくは分岐鎖のアルキレン
基を示す。）で表されるアルカノールアミンとを反応さ
せた後、減圧下で処理する、一般式（３） 【化２】 （式中、Ｒ1，Ｒ2及びＲ3は上記と同じ意味を示す。）
で表される高級脂肪酸アルカノールアミドの製造法。1. A compound represented by the formula (1) R 1 —COOH (1) (wherein R 1 represents a linear or branched alkyl group having 5 to 21 carbon atoms, an alkenyl group or a hydroxyalkyl group). The fatty acid represented, or an ester of this fatty acid, and a compound represented by the general formula (2): (In the formula, R 2 represents a hydrogen atom, a hydroxyethyl group, or a linear or branched alkyl group having 1 to 8 carbon atoms.
R 3 represents a linear or branched alkylene group having 1 to 6 carbon atoms. ) Is reacted with an alkanolamine and then treated under reduced pressure, represented by the general formula (3): (In the formula, R 1 , R 2 and R 3 have the same meanings as described above.)
A method for producing a higher fatty acid alkanolamide represented by:
接触させる請求項１記載の製造法。2. The method according to claim 1, wherein steam and / or an inert gas are brought into contact with each other under reduced pressure.
エステルあるいは油脂と、一般式（２）において、Ｒ2
が炭素数１〜８の直鎖もしくは分岐鎖のアルキル基であ
るＮ−アルキルアルカノールアミンとをアルカリ触媒存
在下で反応させる請求項１又は２記載の製造法。3. A methyl ester of a fatty acid or a fat or oil represented by the general formula (1) and R 2 in the general formula (2).
The method according to claim 1 or 2, wherein is reacted with an N-alkylalkanolamine, which is a linear or branched alkyl group having 1 to 8 carbon atoms, in the presence of an alkali catalyst.
１〜３のいずれかに記載の製造法。4. The production method according to claim 1, wherein water is added before the treatment under reduced pressure.
aである請求項１〜４のいずれかに記載の製造法。5. The pressure during the depressurization treatment is 0.6 to 26.6 kP.
It is a, The manufacturing method in any one of Claims 1-4.
る請求項１〜５のいずれかに記載の製造法。6. The production method according to claim 1, wherein the temperature during the depressurization treatment is 40 to 200 ° C.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006188478A (en) * | 2005-01-07 | 2006-07-20 | Lion Akzo Kk | Method for producing carboxylic acid amide, and carboxylic acid amide derivative and method for producing the same |
| WO2017217445A1 (en) | 2016-06-16 | 2017-12-21 | 花王株式会社 | Rheology modifier |
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2001
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|---|---|---|---|---|
| JP2006188478A (en) * | 2005-01-07 | 2006-07-20 | Lion Akzo Kk | Method for producing carboxylic acid amide, and carboxylic acid amide derivative and method for producing the same |
| JP4686197B2 (en) * | 2005-01-07 | 2011-05-18 | ライオン・アクゾ株式会社 | Method for producing carboxylic acid amide, carboxylic acid amide derivative and method for producing the same |
| WO2017217445A1 (en) | 2016-06-16 | 2017-12-21 | 花王株式会社 | Rheology modifier |
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