JP3426785B2 - Method for producing quaternary ammonium salt - Google Patents
Method for producing quaternary ammonium saltInfo
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- JP3426785B2 JP3426785B2 JP11284595A JP11284595A JP3426785B2 JP 3426785 B2 JP3426785 B2 JP 3426785B2 JP 11284595 A JP11284595 A JP 11284595A JP 11284595 A JP11284595 A JP 11284595A JP 3426785 B2 JP3426785 B2 JP 3426785B2
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- general formula
- ammonium salt
- quaternary ammonium
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Description
【０００１】[0001]
【産業上の利用分野】本発明は第４級アンモニウム塩の
製造法に関する。さらに詳しく述べるなら、繊維に対し
て優れた柔軟性を付与し、毛髪に対しては優れた柔軟性
と平滑性を付与でき、さらに、生分解性が良好な第４級
アンモニウム塩の製造法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing a quaternary ammonium salt. More specifically, it relates to a method for producing a quaternary ammonium salt which can impart excellent flexibility to fibers and excellent flexibility and smoothness to hair, and further has good biodegradability. .
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
繊維や毛髪等の柔軟剤基剤として用いられている、下記
式（Ａ）2. Description of the Related Art Conventionally, the problems to be solved by the invention
The following formula (A) used as a softening agent base for fibers and hair
【０００３】[0003]
【化５】 [Chemical 5]
【０００４】（式中、 Ｒは短鎖アルキル基又はヒドロ
キシアルキル基、R'は長鎖アルキル基又はアルケニル
基、ｎは１〜６の整数を示す。）で表される化合物のよ
うなエステル基を持つ第４級アンモニウム塩を製造する
方法としては、対応する下記式(B)
X-(CH2)nCOOR' (B)
（式中、R'及びｎは前記と同じ意味を示し、X はハロゲ
ン原子を示す。）で表されるハロゲン化エステルと、下
記式(C)(In the formula, R is a short-chain alkyl group or hydroxyalkyl group, R'is a long-chain alkyl group or alkenyl group, and n is an integer of 1 to 6.) An ester group such as a compound As a method for producing a quaternary ammonium salt having the formula, the corresponding formula (B) X- (CH 2 ) n COOR '(B) (wherein R'and n have the same meanings as described above, X Represents a halogen atom) and a halogenated ester represented by the following formula (C)
【０００５】[0005]
【化６】 [Chemical 6]
【０００６】（式中、R は前記と同じ意味を示す。）で
表される第３級アミンとを、ハロゲン化エステル(B) と
第３級アミン(C) の合計量の３〜５重量倍の大量の溶媒
中、解放系で反応させる方法（参照；Antimicrob. Agen
ts Chemother. (1990), 34(10), 1949-54)、あるいは上
記式(B) で表されるハロゲン化エステルと、下記式
（Ｄ）The tertiary amine represented by the formula (wherein R has the same meaning as described above) is added to the halogenated ester (B) and the tertiary amine (C) in an amount of 3 to 5% by weight. A method of reacting in an open system in double the volume of solvent (see Antimicrob. Agen)
ts Chemother. (1990), 34 (10), 1949-54) or a halogenated ester represented by the above formula (B) and the following formula (D)
【０００７】[0007]
【化７】 [Chemical 7]
【０００８】（式中、Ｒ は前記と同じ意味を示す。）
で表される第２級アミンとを反応させて、下記式(E)(In the formula, R has the same meaning as described above.)
By reacting with a secondary amine represented by the following formula (E)
【０００９】[0009]
【化８】 [Chemical 8]
【００１０】で表されるエステルアミンを得、次に下記
式(F)
R−X (F)
（式中、R 及びX は前記と同じ意味を示す。）で表され
る４級化剤で４級化させる方法等が一般的であった。An ester amine represented by the following formula is obtained, and then a quaternizing agent represented by the following formula (F) R--X (F) (wherein R and X have the same meanings as described above). The method of quaternization was common.
【００１１】しかしこれらの方法では、前者は大量の溶
媒を使用し、かつ解放系での反応であるため、工業的生
産において効率が悪かったり、設備的負荷が大きいとい
う欠点があり、後者はアミノ化剤として低級アミンの水
溶液を用いるため、エステルの加水分解等の副反応によ
る純分低下の問題や、工程が長いため設備、コスト的に
不利という問題があった。従って、本発明の目的は、エ
ステル基を持つ第４級アンモニウム塩の安価で工業的に
有利な製造法を提供することにある。However, these methods have the drawbacks that the former uses a large amount of solvent and is a reaction in an open system, so that the efficiency is poor in industrial production and the facility load is large, and the latter is amino. Since an aqueous solution of a lower amine is used as the agent, there is a problem that the net content is lowered due to a side reaction such as hydrolysis of an ester, and that the process is long, which is disadvantageous in equipment and cost. Therefore, an object of the present invention is to provide an inexpensive and industrially advantageous production method of a quaternary ammonium salt having an ester group.
【００１２】[0012]
【課題を解決するための手段】本発明者らは、上記課題
を解決すべく鋭意検討した結果、ハロゲン化エステルと
第３級アミンとを密閉系で反応させることによって、上
記目的を達成できることを見出し、本発明を完成した。
すなわち、本発明は、一般式(1)Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that the above objects can be achieved by reacting a halogenated ester with a tertiary amine in a closed system. Heading, completed the present invention.
That is, the present invention, the general formula (1)
【００１３】[0013]
【化９】 [Chemical 9]
【００１４】（式中、R1, R2及びR3は同一又は異なっ
て、炭素数１〜４のアルキル基又はヒドロキシアルキル
基、R4及びR5は同一又は異なって、水酸基で置換されて
いてもよい炭素数８〜22のアルキル基又はアルケニル
基、 Aは炭素数２〜３のアルキレン基、 Xはハロゲン原
子、ｎは１〜６の整数、ｍはアルキレンオキサイドの平
均付加モル数を示す０〜20の数である。）で表される第
４級アンモニウム塩を製造するに当たり、一般式(2)(Wherein R 1 , R 2 and R 3 are the same or different, an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, and R 4 and R 5 are the same or different and are substituted with a hydroxyl group. Optionally an alkyl or alkenyl group having 8 to 22 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, X is a halogen atom, n is an integer of 1 to 6, and m is the average number of moles of alkylene oxide added. In producing the quaternary ammonium salt represented by the general formula (2)
【００１５】[0015]
【化１０】 [Chemical 10]
【００１６】（式中、R4, R5, A, X, ｎ及びｍは前記と
同じ意味を示す。）で表されるハロゲン化エステルと、
一般式（３）(Wherein R 4 , R 5 , A, X, n and m have the same meanings as described above), and
General formula (3)
【００１７】[0017]
【化１１】 [Chemical 11]
【００１８】（式中、Ｒ１， Ｒ２及びR3は前記と同じ
意味を示す。）で表される第３級アミンとを密閉系で反
応させることを特徴とする、第４級アンモニウム塩の製
造法を提供するものである。A quaternary ammonium salt characterized by reacting with a tertiary amine represented by the formula (wherein R 1 , R 2 and R 3 have the same meanings as described above) in a closed system. The present invention provides a manufacturing method of.
【００１９】一般式(1) で表されるアンモニウム塩にお
いて、R1, R2及びR3は炭素数１〜４のアルキル基又はヒ
ドロキシアルキル基を示すが、具体的にはメチル、エチ
ル、プロピル、ブチル、ヒドロキシエチル基等が挙げら
れ、好ましくはメチル基である。R4及びR5は水酸基で置
換されていてもよい炭素数８〜22のアルキル基又はアル
ケニル基を示すが、具体的にはデシル、ドデシル、テト
ラデシル、ヘキサデシル、オクタデシル、エイコシル、
ドコシル等の基が挙げられ、好ましくはテトラデシル、
ヘキサデシル、オクタデシル基及びこれらの混合物であ
る。特にR4がオクタデシル基又はヘキサデシル基で、R5
がヘキサデシル基又はテトラデシル基の組み合わせ、更
にはR4がオクタデシル基で、R5がヘキサデシル基の組み
合わせが好ましい。Aは炭素数２〜３のアルキレン基を
示すが、好ましくはIn the ammonium salt represented by the general formula (1), R 1 , R 2 and R 3 represent an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, and specifically, methyl, ethyl and propyl. , A butyl group, a hydroxyethyl group and the like, and a methyl group is preferable. R 4 and R 5 represent an alkyl group or an alkenyl group having 8 to 22 carbon atoms which may be substituted with a hydroxyl group, and specifically, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl,
Examples thereof include groups such as docosyl, preferably tetradecyl,
Hexadecyl, octadecyl groups and mixtures thereof. Particularly, R 4 is an octadecyl group or a hexadecyl group, and R 5
Is a combination of a hexadecyl group or a tetradecyl group, and further, a combination of R 4 is an octadecyl group and R 5 is a hexadecyl group. A represents an alkylene group having 2 to 3 carbon atoms, preferably
【００２０】[0020]
【化１２】 [Chemical 12]
【００２１】ｎは１〜６の整数を示すが、好ましくは１
〜５、更に好ましくは１である。ｍはアルキレンオキサ
イドの平均付加モル数を示す０〜20の数であるが、好ま
しくは０〜５、更に好ましくは０である。X はCl, Br,
I 等のハロゲン原子を示すが、好ましくはClである。N represents an integer of 1 to 6, preferably 1
-5, and more preferably 1. m is a number of 0 to 20, which represents the average number of moles of alkylene oxide added, and is preferably 0 to 5, and more preferably 0. X is Cl, Br,
A halogen atom such as I is shown, but Cl is preferable.
【００２２】本発明の方法により製造される一般式(1)
で表されるアンモニウム塩としては、例えば次のような
ものが挙げられる。The general formula (1) produced by the method of the present invention
Examples of the ammonium salt represented by are as follows.
【００２３】[0023]
【化１３】 [Chemical 13]
【００２４】本発明の製造方法においては、前記一般式
(2) で表されるハロゲン化エステルと、一般式(3) で表
される第３級アミンとを密閉系で反応させて、一般式
(1) で表される第４級アンモニウム塩を製造するが、こ
の反応に用いられる密閉系の反応装置としては、オート
クレーブ等の耐熱耐圧装置であれば良く、内部に攪拌装
置を有しているものが好ましい。本発明においては、密
閉系で反応を行うことにより、低沸点の第３級アミンが
系外に排出することなく、高圧下で反応液とよく混合す
るために、効率よく反応を進行させることができる。ま
た、本発明の反応は、無溶媒系、もしくは一般式(2) で
表されるハロゲン化エステルと一般式(3) で表される第
３級アミンの合計量に対し100 重量％以下、好ましくは
５〜50重量％の溶媒中で反応を行うのが望ましい。溶媒
量が一般式(2) で表されるハロゲン化エステルと一般式
(3) で表される第３級アミンの合計量に対し 100重量％
を超えたとしても収率等の大幅な向上がなく、設備的負
荷が増すだけで、効率的ではない。ここで用いられる溶
媒としては、メタノール、エタノール、イソプロピルア
ルコール、アセトン等の極性有機溶媒が挙げられる。ま
た、本発明の反応においては、油脂とグリセリンとアル
キレンオキサイドとを、好ましくは１：(0.1〜５）：
（２〜100)のモル比で反応させて得られる反応物や、ア
ルカノールアミド等のノニオン性活性剤及びこれらの混
合物を添加して反応を行っても良い。In the production method of the present invention, the general formula
By reacting the halogenated ester represented by (2) with the tertiary amine represented by the general formula (3) in a closed system, the general formula
The quaternary ammonium salt represented by (1) is produced. The closed reactor used for this reaction may be a heat-resistant pressure-resistant device such as an autoclave and has a stirrer inside. Those are preferable. In the present invention, the reaction is carried out in a closed system, so that the low boiling point tertiary amine is well mixed with the reaction solution under high pressure without being discharged to the outside of the system, so that the reaction can proceed efficiently. it can. The reaction of the present invention is a solvent-free system or 100% by weight or less, preferably 100% by weight or less, based on the total amount of the halogenated ester represented by the general formula (2) and the tertiary amine represented by the general formula (3). Is preferably carried out in a solvent of 5 to 50% by weight. Halogenated ester represented by the general formula (2) and the general formula
100% by weight based on the total amount of the tertiary amine represented by (3)
Even if it exceeds, there is no significant improvement in yield and the like, and the facility load is increased, which is not efficient. Examples of the solvent used here include polar organic solvents such as methanol, ethanol, isopropyl alcohol, and acetone. In addition, in the reaction of the present invention, fat and oil, glycerin and alkylene oxide, preferably 1: (0.1 to 5):
The reaction may be carried out by adding a reaction product obtained by reacting at a molar ratio of (2 to 100), a nonionic activator such as alkanolamide, and a mixture thereof.
【００２５】本発明の方法において、一般式(2) で表さ
れるハロゲン化エステルと、一般式(3) で表される第３
級アミンの仕込み割合は、一般式(2) で表されるハロゲ
ン化エステルに対し、一般式(3) で表される第３級アミ
ン 0.9〜 5.0倍モルが好ましく、0.95〜 2.0倍モルが更
に好ましい。また反応温度は30〜 120℃が好ましく、40
〜70℃が更に好ましい。反応時間は 0.1〜10時間が好ま
しい。本発明で用いられる一般式(2) で表されるハロゲ
ン化エステルは、下記反応式に示すように、一般式(4)
で表されるハロカルボン酸と一般式(5) で表される高級
アルコール又はそのアルキレンオキサイド付加物とを反
応させることにより容易に得ることができる。In the method of the present invention, the halogenated ester represented by the general formula (2) and the third halogenated ester represented by the general formula (3) are used.
The proportion of the tertiary amine charged is preferably 0.9 to 5.0 times by mole, and more preferably 0.95 to 2.0 times by mole, with respect to the halogenated ester represented by the general formula (2). preferable. The reaction temperature is preferably 30 to 120 ° C., 40
-70 ° C is more preferable. The reaction time is preferably 0.1 to 10 hours. The halogenated ester represented by the general formula (2) used in the present invention is represented by the general formula (4) as shown in the following reaction formula.
It can be easily obtained by reacting the halocarboxylic acid represented by: with the higher alcohol represented by the general formula (5) or an alkylene oxide adduct thereof.
【００２６】[0026]
【化１４】 [Chemical 14]
【００２７】（式中、R4, R5, A, X, ｎ及びｍは前記と
同じ意味を示す。）
一般式(4) で表されるハロカルボン酸としては、モノク
ロロ酢酸、モノクロロプロピオン酸、モノクロロ酪酸、
モノクロロヘキサン酸等が挙げられる。また一般式(5)
で表される高級アルコール又はそのアルキレンオキサイ
ド付加物としては、下記式で表される高級アルコールあ
るいはこれらのエチレンオキサイド付加物、プロピレン
オキシド付加物等が挙げられる。(In the formula, R 4 , R 5 , A, X, n and m have the same meanings as described above.) Examples of the halocarboxylic acid represented by the general formula (4) include monochloroacetic acid, monochloropropionic acid, Monochlorobutyric acid,
Examples thereof include monochlorohexanoic acid. Also, the general formula (5)
Examples of higher alcohols represented by or alkylene oxide adducts thereof include higher alcohols represented by the following formulas or ethylene oxide adducts or propylene oxide adducts thereof.
【００２８】[0028]
【化１５】 [Chemical 15]
【００２９】また、本発明で用いられる一般式(3) で表
される第３級アミンとしては、トリメチルアミン、トリ
エチルアミン、トリプロピルアミン、Ｎ−メチルジエタ
ノールアミン、Ｎ，Ｎ−ジメチルエタノールアミン、ト
リエタノールアミン、Ｎ，Ｎ−ジメチル−２−ヒドロキ
シプロピルアミン、Ｎ，Ｎ−ジメチルブチルアミン、
Ｎ，Ｎ−ジエチルメチルアミン、Ｎ，Ｎ−ジメチルイソ
プロピルアミン、Ｎ−メチルジブチルアミン等が挙げら
れる。The tertiary amine represented by the general formula (3) used in the present invention includes trimethylamine, triethylamine, tripropylamine, N-methyldiethanolamine, N, N-dimethylethanolamine and triethanolamine. , N, N-dimethyl-2-hydroxypropylamine, N, N-dimethylbutylamine,
Examples include N, N-diethylmethylamine, N, N-dimethylisopropylamine, N-methyldibutylamine and the like.
【００３０】本発明の方法で得られた一般式(1) で表さ
れる第４級アンモニウム塩は、さらに晶析や溶媒抽出等
により精製してよいことは勿論であるが、精製すること
なく反応混合物のままで柔軟剤基剤として用いても、柔
軟性及び匂いともに優れており、繊維や毛髪等の柔軟剤
基剤として非常に有用である。また、更に柔軟性能、保
存安定性を向上させるための高級アルコール、高級脂肪
酸、その他粘度調整剤、保存安定剤として低級アルコー
ル、さらには公知のカチオン性活性剤、ノニオン性活性
剤、無機塩、ｐＨ調整剤、ハイドロトロープ剤、香料、
消泡剤、顔料等を必要に応じて添加し、エマルジョン化
すれば、柔軟剤組成物を調製することができる。The quaternary ammonium salt represented by the general formula (1) obtained by the method of the present invention may of course be further purified by crystallization, solvent extraction or the like, but without purification. Even when used as a softening agent base as it is as a reaction mixture, it is excellent in both flexibility and odor, and is very useful as a softening agent base for fibers, hair and the like. Further, higher alcohols, higher fatty acids, other viscosity modifiers for improving softness and storage stability, lower alcohols as storage stabilizers, and further known cationic activators, nonionic activators, inorganic salts, pH Conditioner, hydrotrope, fragrance,
A softening agent composition can be prepared by adding an antifoaming agent, a pigment and the like as necessary and emulsifying them.
【００３１】[0031]
【実施例】以下に実施例により本発明を更に詳細に説明
するが、本発明はこれらの実施例に限定されるものでは
ない。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００３２】実施例１
攪拌機、温度計、圧力計の付いた 0.5リットルオートク
レーブにモノクロロ酢酸 ２−ヘキサデシルエイコシル
100ｇ、トリメチルアミン15ｇ、イソプロピルアルコー
ル28ｇを入れ、50℃まで昇温した。そのままの温度で３
時間攪拌し、反応を終結させた。反応後、過剰のトリメ
チルアミンを留去し、下記式(6) で表される化合物を含
む反応混合液を 138ｇ得た。クロロイオン％ 4.28(理論
値4.31)、反応率99.3％であった。Example 1 Monochloroacetic acid 2-hexadecyl eicosyl was added to a 0.5 liter autoclave equipped with a stirrer, thermometer and pressure gauge.
100 g, 15 g of trimethylamine and 28 g of isopropyl alcohol were added and the temperature was raised to 50 ° C. 3 at the same temperature
The reaction was terminated by stirring for a time. After the reaction, excess trimethylamine was distilled off to obtain 138 g of a reaction mixture containing a compound represented by the following formula (6). The chloroion% 4.28 (theoretical value 4.31) and the reaction rate were 99.3%.
【００３３】[0033]
【化１６】 [Chemical 16]
【００３４】比較例１
攪拌機、温度計、冷却管の付いた 0.5リットル４つ口フ
ラスコを用いて、実施例１と同様の原料を用い、実施例
１と同様の操作を行った。得られた混合物のクロロイオ
ン％ 1.34 、反応率31.1％であった。Comparative Example 1 Using a 0.5 liter four-necked flask equipped with a stirrer, a thermometer and a cooling tube, the same raw materials as in Example 1 were used and the same operation as in Example 1 was performed. The chloroion% 1.34 and the reaction rate 31.1% of the obtained mixture were obtained.
【００３５】実施例２
攪拌機、温度計、圧力計の付いた 0.5リットルオートク
レーブにモノクロロ酢酸 ２−ヘキサデシルエイコシル
100ｇ、トリメチルアミン12ｇ、硬化牛脂／グリセリン
／エチレンオキサイド＝２／１／12（モル比）反応物28
ｇ、イソプロピルアルコール15ｇを入れ、50℃まで昇温
した。そのままの温度で３時間攪拌し、反応を終結させ
た。反応後、過剰のトリメチルアミンを留去し、上記式
(6) で表される化合物を含む反応混合液を154ｇ得た。
クロロイオン％ 3.76(理論値3.87)、反応率97.2％であ
った。Example 2 Monochloroacetic acid 2-hexadecyl eicosyl was added to a 0.5 liter autoclave equipped with a stirrer, thermometer and pressure gauge.
100 g, trimethylamine 12 g, hardened beef tallow / glycerin / ethylene oxide = 2/1/12 (molar ratio) Reactant 28
and 15 g of isopropyl alcohol were added, and the temperature was raised to 50 ° C. The reaction was terminated by stirring at the same temperature for 3 hours. After the reaction, excess trimethylamine was distilled off,
154 g of a reaction mixture containing the compound represented by (6) was obtained.
The chloroion% was 3.76 (theoretical value: 3.87), and the reaction rate was 97.2%.
【００３６】比較例２
攪拌機、温度計、冷却管の付いた 0.5リットル４つ口フ
ラスコを用いて、実施例２と同様の原料を用い、実施例
２と同様の操作を行った。得られた混合物のクロロイオ
ン％ 0.79 、反応率20.4％であった。Comparative Example 2 Using a 0.5 liter four-necked flask equipped with a stirrer, a thermometer and a condenser, the same raw materials as in Example 2 were used and the same operation as in Example 2 was performed. The obtained mixture had a chloroion% of 0.79 and a reaction rate of 20.4%.
【００３７】実施例３
攪拌機、温度計、圧力計の付いた 0.5リットルオートク
レーブにモノクロロ酢酸 ２−テトラデシルオクタデシ
ル 100ｇ、トリメチルアミン13ｇ、イソプロピルアルコ
ール28ｇを入れ、50℃まで昇温した。そのままの温度で
３時間攪拌し、反応を終結させた。反応後、過剰のトリ
メチルアミンを留去し、下記式(7) で表される化合物を
含む反応混合液を139ｇ得た。クロロイオン％ 4.65(理
論値4.71)、反応率98.7％であった。Example 3 100 g of 2-tetradecyl octadecyl monochloroacetate, 13 g of trimethylamine and 28 g of isopropyl alcohol were placed in a 0.5 liter autoclave equipped with a stirrer, a thermometer and a pressure gauge, and the temperature was raised to 50 ° C. The reaction was terminated by stirring at the same temperature for 3 hours. After the reaction, excess trimethylamine was distilled off to obtain 139 g of a reaction mixture containing a compound represented by the following formula (7). Chloroion% 4.65 (theoretical value 4.71), the reaction rate was 98.7%.
【００３８】[0038]
【化１７】 [Chemical 17]
【００３９】実施例４
攪拌機、温度計、圧力計の付いた 0.5リットルオートク
レーブにモノクロロ酪酸 ２−ヘキサデシルエイコシル
100ｇ、トリメチルアミン11ｇ、イソプロピルアルコー
ル27ｇを入れ、50℃まで昇温した。そのままの温度で５
時間攪拌し、反応を終結させた。反応後、過剰のトリメ
チルアミンを留去し、下記式(8) で表される化合物を含
む反応混合液を 136ｇ得た。クロロイオン％ 4.10(理論
値4.14)、反応率99.0％であった。Example 4 Monochlorobutyric acid 2-hexadecyl eicosyl was added to a 0.5 liter autoclave equipped with a stirrer, thermometer and pressure gauge.
100 g, 11 g of trimethylamine and 27 g of isopropyl alcohol were added and the temperature was raised to 50 ° C. 5 at the same temperature
The reaction was terminated by stirring for a time. After the reaction, excess trimethylamine was distilled off to obtain 136 g of a reaction mixture containing a compound represented by the following formula (8). The chloroion% 4.10 (theoretical value 4.14) and the reaction rate were 99.0%.
【００４０】[0040]
【化１８】 [Chemical 18]
【００４１】実施例５
攪拌機、温度計、圧力計の付いた 0.5リットルオートク
レーブにモノクロロヘキサン酸 ２−ヘキサデシルエイ
コシル 100ｇ、トリメチルアミン13ｇ、イソプロピルア
ルコール27ｇを入れ、50℃まで昇温した。そのままの温
度で５時間攪拌し、反応を終結させた。反応後、過剰の
トリメチルアミンを留去し、下記式(9)で表される化合
物を含む反応混合液を 136ｇ得た。クロロイオン％ 3.7
5(理論値3.82) 、反応率98.2％であった。Example 5 100 g of 2-hexadecyl eicosyl monochlorohexanoate, 13 g of trimethylamine and 27 g of isopropyl alcohol were placed in a 0.5 liter autoclave equipped with a stirrer, a thermometer and a pressure gauge, and the temperature was raised to 50 ° C. The reaction was terminated by stirring at the same temperature for 5 hours. After the reaction, excess trimethylamine was distilled off to obtain 136 g of a reaction mixture containing a compound represented by the following formula (9). Chlorion% 3.7
5 (theoretical value 3.82) and the reaction rate was 98.2%.
【００４２】[0042]
【化１９】 [Chemical 19]
【００４３】[0043]
【発明の効果】上記実施例及び比較例の結果からも明ら
かなように、本発明の方法によると、密閉系で反応を行
うことにより、反応率を著しく向上させることができ
る。As is clear from the results of the above Examples and Comparative Examples, according to the method of the present invention, the reaction rate can be remarkably improved by carrying out the reaction in a closed system.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平８−92875（ＪＰ，Ａ) 特開 平８−217732（ＪＰ，Ａ) 特開 昭54−130509（ＪＰ，Ａ) 特開 昭56−92253（ＪＰ，Ａ) 特開 平２−11545（ＪＰ，Ａ) 特開 平６−199748（ＪＰ，Ａ) 国際公開96／3370（ＷＯ，Ａ１) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 229/12 C07C 227/08 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── --- Continuation of the front page (56) References JP-A-8-92875 (JP, A) JP-A-8-217732 (JP, A) JP-A-54-130509 (JP, A) JP-A-56- 92253 (JP, A) JP 2-11545 (JP, A) JP 6-199748 (JP, A) International Publication 96/3370 (WO, A1) (58) Fields investigated (Int.Cl. 7) , DB name) C07C 229/12 C07C 227/08 CA (STN) REGISTRY (STN)
Claims (4)
４のアルキル基又はヒドロキシアルキル基、R4及びR5は
同一又は異なって、水酸基で置換されていてもよい炭素
数８〜22のアルキル基又はアルケニル基、 Aは炭素数２
〜３のアルキレン基、 Xはハロゲン原子、ｎは１〜６の
整数、ｍはアルキレンオキサイドの平均付加モル数を示
す０〜20の数である。）で表される第４級アンモニウム
塩を製造するに当たり、一般式(2) 【化２】 （式中、R4, R5, A, X, ｎ及びｍは前記と同じ意味を示
す。）で表されるハロゲン化エステルと、一般式(3) 【化３】 （式中、R1, R2及びR3は前記と同じ意味を示す。）で表
される第３級アミンとを密閉系で反応させることを特徴
とする、第４級アンモニウム塩の製造法。1. A general formula (1): (In the formula, R 1 , R 2 and R 3 are the same or different and have 1 to 1 carbon atoms.
4 alkyl group or hydroxyalkyl group, R 4 and R 5 are the same or different, and are an alkyl group or alkenyl group having 8 to 22 carbon atoms which may be substituted with a hydroxyl group, and A is 2 carbon atoms.
To 3 are alkylene groups, X is a halogen atom, n is an integer from 1 to 6, and m is a number from 0 to 20 showing the average number of moles of alkylene oxide added. ) In producing a quaternary ammonium salt represented by the general formula (2): (Wherein R 4 , R 5 , A, X, n and m have the same meanings as described above), and a halogenated ester represented by the general formula (3) (Wherein R 1 , R 2 and R 3 have the same meanings as described above) and a tertiary amine is reacted in a closed system to produce a quaternary ammonium salt. .
チル基、R4がオクタデシル基又はヘキサデシル基、R5が
ヘキサデシル基又はテトラデシル基、A が 【化４】 ｎが１〜５、ｍが０〜５である請求項１記載の第４級ア
ンモニウム塩の製造法。2. In the general formula (1), R 1 , R 2 and R 3 are methyl groups, R 4 is an octadecyl group or a hexadecyl group, R 5 is a hexadecyl group or a tetradecyl group, and A 1 is The method for producing a quaternary ammonium salt according to claim 1, wherein n is 1 to 5 and m is 0 to 5.
チル基、R4がオクタデシル基、R5がヘキサデシル基、ｎ
が１、ｍが０、X がClである請求項１記載の第４級アン
モニウム塩の製造法。3. In the general formula (1), R 1 , R 2 and R 3 are methyl groups, R 4 is an octadecyl group, R 5 is a hexadecyl group, n
The method for producing a quaternary ammonium salt according to claim 1, wherein m is 1, m is 0, and X is Cl.
るハロゲン化エステルと一般式(3) で表される第３級ア
ミンの合計量に対し100 重量％以下の溶媒中で反応させ
ることを特徴とする、請求項１〜３のいずれか一項に記
載の第４級アンモニウム塩の製造法。4. A reaction in a solventless system or in a solvent of 100% by weight or less based on the total amount of the halogenated ester represented by the general formula (2) and the tertiary amine represented by the general formula (3). The method for producing a quaternary ammonium salt according to any one of claims 1 to 3, wherein
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11284595A JP3426785B2 (en) | 1995-05-11 | 1995-05-11 | Method for producing quaternary ammonium salt |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11284595A JP3426785B2 (en) | 1995-05-11 | 1995-05-11 | Method for producing quaternary ammonium salt |
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| Publication Number | Publication Date |
|---|---|
| JPH08301823A JPH08301823A (en) | 1996-11-19 |
| JP3426785B2 true JP3426785B2 (en) | 2003-07-14 |
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ID=14596977
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Also Published As
| Publication number | Publication date |
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