JPH0428252B2 - - Google Patents
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- JPH0428252B2 JPH0428252B2 JP3500884A JP3500884A JPH0428252B2 JP H0428252 B2 JPH0428252 B2 JP H0428252B2 JP 3500884 A JP3500884 A JP 3500884A JP 3500884 A JP3500884 A JP 3500884A JP H0428252 B2 JPH0428252 B2 JP H0428252B2
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- tertiary amine
- amine
- chain alkyl
- benzyl
- branched
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Description
本発明は脂肪族第３級アミンとハロゲン化ベン
ジルとを反応させて、直鎖アルキル第４級アンモ
ニウム塩と分岐鎖アルキル第４級アンモニウム塩
との混合溶液を製造する方法に関するものであ
る。
脂肪族第４級ベンジルアンモニウム塩、特に脂
肪族第４級ベンジルアンモニウムクロライドは殺
菌・消毒剤として有用である。しかしながら、こ
のような用途に使用される第４級アンモニウム塩
は未反応アミンの含有量の少ないことが必要であ
る。未反応アミンの残存量を少なくするには、通
常アミンに対し過剰のハロゲン化ベンジルを用い
ることによつて可能であるが、上記用途に用いら
れる第４級アンモニウム塩は未反応塩化ベンジル
の含有量の少ないことも必要で、アミンに対し過
剰のハロゲン化ベンジルを用いた場合、反応終了
後、未反応ハロゲン化ベンジルを分離し精製する
必要がある。
しかしながら、反応終了後に未反応ハロゲン化
ベンジルを蒸留で除こうとすると、ハロゲン化ベ
ンジル類は沸点が高いので（塩化ベンジルは179
℃、臭化ベンジルは198℃）反応溶媒として用い
たエタノール、イソプロパノールが先に留去し、
粘稠な液状となり蒸留が困難になる。溶媒とし
て、沸点が高いエチレングリコール（沸点197
℃）、プロピレングリコール（沸点188℃）等の２
価アルコールを用いると、未反応ハロゲン化ベン
ジルの除去蒸留の際に目的生成物の第４級アンモ
ニウム塩が高温で長時間加熱されることにより分
解するという別の問題を生ずる。従つて未反応ア
ミンと未反応ハロゲン化ベンジル両方の残存量を
少なくするにはアミンとハロゲン化ベンジルの量
論量を正確に反応させる必要がある。
前記用途に用いられるアミンは油脂類を出発原
料として得られる直鎖アミンを主成分とする所謂
天然アミンと、オキソ法で合成される高級アルコ
ールをアルキルクロリドに転換した後、これを低
級ジアルキルアミンでアミノ化する方法または特
開昭58−105945号明細書に開示されているよう
に、長鎖オレフインの低級ジアルキルアミンとを
水素、一酸化炭素混合ガスの存在下に反応させる
方法によつて得られる合成アミンとに大別でき
る。合成アミンは一般に分岐鎖アルキル第３級ア
ミンを20〜60重量％含む分岐鎖・直鎖混合アルキ
ル第３級アミンである。
反応生成物中の未反応アミンと未反応ハロゲン
化ベンジル両方の残存量を少なくするために、直
鎖アミンとハロゲン化ベンジンを量論量で反応さ
せた場合には短時間に反応が進むが、分岐鎖・直
鎖混合アルキル第３級アミンを同様に反応させる
と分岐鎖アルキル第３級アミンの反応速度が直鎖
アルキル第３級アミンに比して著しく遅く、直鎖
アルキル第３級アミンの反応率が100％に達して
も、分岐鎖アルキル第３級アミンの未反応分が多
い。この反応率を高めるためにはハロゲン化ベン
ジルの過剰量の使用が必要で、その結果ハロゲン
化ベンジル残存量の低減が困難である。
本発明はこのような混合アミンのハロゲン化ベ
ンジルによる４級化を、比較的短時間に完結し、
かつ、未反応アミンと未反応ハロゲン化ベンジル
残存量を少なくすることを可能とするもので、脂
肪族第３級アミンとハロゲン化ベンジルとを反応
させて、直鎖アルキル第４級アンモニウム塩と分
岐鎖アルキル第４級アンモニウム塩との混合溶液
を製造する方法において、まず分岐鎖アルキル第
３級アミンを主成分とする第３級アミンを過剰量
のハロゲン化ベンジルと反応させた後、実質的に
分岐鎖アルキル基を含まない直鎖アルキル第３級
アミンを加えてハロゲン化ベンジルとを反応させ
ることを特徴とする混合第４級アンモニウム塩の
製造方法である。
本発明で原料として用いられる長鎖アルキル第
３級アミンのうち直鎖アルキルアミンは一般式
（但し、R1およびR2はそれぞれ独立にメチル基
またはエチル基であり、R3は炭素数が８〜25の
直鎖アルキル基である。）で示される脂肪族第３
級アミンであり、また分岐鎖アルキルアミンは一
般式
（但し、R1およびR2はそれぞれ独立にメチル基
またはエチル基であり、R4およびR5はそれぞれ
直鎖アルキル基であり、R4とR5の炭素数の合計
が６〜23である。）で示される脂肪族第３級アミ
ンである。
本発明の方法においては、まず分岐鎖アルキル
第３級アミンを主成分とする第３級アミンを過剰
量のハロゲン化ベンジルにより４級化し、次いで
反応性の高い直鎖アルキル第３級アミンをハロゲ
ン化ベンジルの残存量に見合つた量だえ加える
か、または加えるべき直鎖アルキル第３級アミン
量よりもハロゲン化ベンジルの残存量が少ない場
合には更に必要量のハロゲン化ベンジルを加え
て、直鎖アルキル第３級アミンとハロゲン化ベン
ジルを量論量で反応させることにより、短い時間
で未反応アミンと未反応ハロゲン化ベンジルの残
存量の少ない混合アルキル第４級アンモニウム塩
を得ることができる。
本発明の方法における第３級アミンとハロゲン
化ベンジルとの反応は公知の如くエタノール、イ
ソプロパノール、エチレングリコール、プロピレ
ングリコール等の１価または２価の低級アルコー
ル溶媒中で行なうことにより、反応液の粘度上昇
による反応速度の低下を防ぐことができる。更に
反応速度を速くするためにアルカリ剤または水を
加えることができる。アルカリ剤は水酸化ナトリ
ウム、水酸化カリ、炭酸ナトリウム、重炭酸ナト
リウムなどが用いられる。
反応温度は40〜120℃の範囲内で選択すること
ができ、反応圧力は大気圧下でもよいが、反応溶
媒の種類と反応温度によつては加圧状態に保つて
もよい。
本発明における原料の第３級アミンとしては、
例えばオキソ法により合成された分岐鎖、直鎖混
合アルキル第３級アミンを用いることができる。
この場合には、分岐鎖アルキル第３級アミンと直
鎖アルキル第３級アミンとは沸点が異なるので、
蒸留により両者を分別する。この分別蒸留におい
ては、分岐鎖アルキル第３級アミン留分中には直
鎖アルキル第３級アミンは15〜30重量％、場合に
よつてはそれ以上の混入が許されるが、直鎖アル
キル第３級アミン留分中の分岐鎖アルキル第３級
アミンの混入量は１重量％以下であることが好ま
しい。
ハロゲン化ベンジルとしては塩化ベンジル、臭
化ベンジルが用いられる。
以下、実施例および比較例により本発明を具体
的に説明するが、本発明はこれらの実施例により
限定されるものではない。
参考例
（直鎖アルキル第３級アミンの４級化反応）
試薬Ｎ，Ｎ−ジメチルドデシルアミンを蒸留し
不純物を除いたもの213.4ｇ（1.0モル）とイソプ
ロパノール213.4ｇ、水5.5ｇをガラス製反応槽に
仕込み、撹拌しながら加熱し60℃に保ち、塩化ベ
ンジル126.6ｇ（1.0モル）を１時間で滴下した。
滴下終了後60℃で４時間反応を続行した。
反応液の一部を採取し、ｎ−ヘキサン／メタノ
ール／水混合液を加えることにより、未反応アミ
ンと未反応塩化ベンジルをｎ−ヘキサン相に抽出
し、ｎ−ヘキサン相をガスクロ分析する方法によ
り未反応アミンと未反応塩化ベンジル濃度を測定
した。
未反応アミン濃度は0.22重量％（アミン反応率
99.4モル％）、未反応塩化ベンジル濃度は0.1重量
％であつた。
比較例
（分岐鎖と直鎖アルキル混合第３級アミンの４
級化反応）
１−ドデセンとジメチルアミンおよび水素・一
酸化炭素混合ガスより合成したＮ，Ｎ−ジメチル
−トリデシルアミン227.4ｇ（1.0モル）直鎖率
61.4重量％）とイソプロパノール227.4ｇ、水６
ｇをガラス製反応槽に仕込み、撹拌しながら加熱
し60℃に保ち、塩化ベンジル139.3ｇ（1.1モル）
を１時間で滴下した。滴下終了後60℃で８時間反
応を続行した。未反応アミン濃度（直鎖アミン＋
分岐鎖アミン）は0.5重量％（アミン反応率98.7
モル％）、未反応塩化ベンジル濃度は2.4重量％で
あつた。
この間の直鎖アルキル第３級アミンと分岐鎖ア
ルキル第３級アミンの反応率の変化を第１表に示
す。直鎖アルキル第３級アミンに比し、分岐鎖ア
ルキル第３級アミンの反応速度が極めて遅いこと
がわかる。
実施例
（分岐鎖アルキル第３級アミンと直鎖アルキル
第３級アミンの分別４級化反応）
１−ドデセンとジメチルアミンおよび水素・一
酸化炭素混合ガスより合成したＮ，Ｎ−ジメチル
−トリデシルアミン227.4ｇ（1.0モル）直鎖率
61.4重量％）とイソプロパノール227.4ｇ、水６
ｇをガラス製反応槽に仕込み、撹拌しながら加熱
し60℃に保ち、塩化ベンジル139.3ｇ（1.1モル）
を１時間で滴下した。滴下終了後60℃で８時間反
応を続行した。未反応アミン濃度（直鎖アミン＋
分岐鎖アミン）は0.5重量％（アミン反応率98.7
モル％）、未反応塩化ベンジル濃度は2.4重量％で
あつた。
この間の直鎖アルキル第３級アミンと分岐鎖ア
ルキル第３級アミンの反応率の変化を第１表に示
す。直鎖アルキル第３級アミンに比し、分岐鎖ア
ルキル第３級アミンの反応速度が極めて遅いこと
がわかる。
実施例
（分岐鎖アルキル第３級アミンと直鎖アルキル
第３級アミンの分別４級化反応）
１−ドデセンとジメチルアミンおよび水素・一
酸化炭素混合ガスより合成したＮ，Ｎ−ジメチル
−トリデシルアミンを、内径４cm、理論段数20段
の蒸留塔を210mmHgの圧力で蒸留し、沸点137.5
〜146.5℃の分岐鎖アミンを主成分とする留分１
と、沸点146.5℃の実質的に直鎖アミンからなる
留分２に分けた。留分１は直鎖アミン25重量％と
分岐鎖アミン75重量％からなり、留分２は直鎖ア
ミンが99.5重量％で分岐鎖アミンは0.5重量％で
あつた。
留分１を153ｇ（0.67モル）とイソプロパノー
ル153ｇおよび水3.4ｇをガラス製反応槽に仕込
み、撹拌しながら加熱し60℃に保ち、塩化ベンジ
ル189.9ｇ（1.5モル）を15分間で滴下した。滴下
終了後60℃で４時間反応を続行した。直鎖アミン
の反応率は100モル％で、分岐鎖アミンの反応率
は99.7モル％であつた。未反応塩化ベンジル残存
濃度は21.0重量％であつた。
次いで前記留分２の直鎖アミン188ｇ（0.83モ
ル）とイソプロパノール188ｇおよび水3.8ｇを加
え60℃で第２段目の反応を４時間行なつた。第１
段と第２段の反応で加えた全アミンの未反応残存
濃度は0.13重量％（アミン反応率99.5モル％）で
未反応塩化ベンジル残存濃度は0.1重量％以下で
あつた。
The present invention relates to a method for producing a mixed solution of a linear alkyl quaternary ammonium salt and a branched alkyl quaternary ammonium salt by reacting an aliphatic tertiary amine with a benzyl halide. Aliphatic quaternary benzyl ammonium salts, particularly aliphatic quaternary benzyl ammonium chloride, are useful as disinfectants. However, the quaternary ammonium salt used for such applications needs to have a low content of unreacted amine. The residual amount of unreacted amine can be reduced by using an excess of benzyl halide relative to the amine, but the quaternary ammonium salt used for the above purpose has a lower content of unreacted benzyl chloride. It is also necessary that the amount of halogenated benzyl is small, and if an excess of halogenated benzyl is used with respect to the amine, it is necessary to separate and purify the unreacted halogenated benzyl after the reaction is completed. However, if you try to remove unreacted benzyl halide by distillation after the reaction is completed, benzyl chloride has a high boiling point (benzyl chloride is 179
℃, 198℃ for benzyl bromide) Ethanol and isopropanol used as reaction solvents are distilled off first,
It becomes a viscous liquid and is difficult to distill. As a solvent, use ethylene glycol with a high boiling point (boiling point 197
℃), propylene glycol (boiling point 188℃), etc.
The use of alcohols poses another problem in that the target product, the quaternary ammonium salt, is decomposed by heating at high temperatures for long periods of time during distillation to remove unreacted benzyl halide. Therefore, in order to reduce the remaining amount of both the unreacted amine and the unreacted benzyl halide, it is necessary to react the amine and the benzyl halide in accurate stoichiometric amounts. The amines used for the above purpose are so-called natural amines mainly composed of linear amines obtained from oils and fats, and higher alcohols synthesized by the oxo method, which are converted into alkyl chlorides, which are then converted into lower dialkyl amines. It can be obtained by an amination method or a method of reacting a long chain olefin with a lower dialkylamine in the presence of a mixed gas of hydrogen and carbon monoxide as disclosed in JP-A-58-105945. It can be broadly classified into synthetic amines. Synthetic amines are generally mixed branched and linear alkyl tertiary amines containing 20 to 60% by weight of branched alkyl tertiary amines. In order to reduce the residual amount of both unreacted amine and unreacted benzyl halide in the reaction product, when linear amine and benzyl halide are reacted in stoichiometric amounts, the reaction proceeds in a short time. When branched and straight chain mixed alkyl tertiary amines are reacted in the same way, the reaction rate of the branched chain alkyl tertiary amine is significantly slower than that of the straight chain alkyl tertiary amine. Even if the reaction rate reaches 100%, there is still a large amount of unreacted branched alkyl tertiary amine. In order to increase this reaction rate, it is necessary to use an excessive amount of halogenated benzyl, and as a result, it is difficult to reduce the residual amount of halogenated benzyl. The present invention completes the quaternization of such a mixed amine with a benzyl halide in a relatively short time,
In addition, it is possible to reduce the amount of unreacted amine and unreacted benzyl halide remaining, and by reacting the aliphatic tertiary amine with the benzyl halide, it is possible to form a branched alkyl quaternary ammonium salt with a linear alkyl quaternary ammonium salt. In the method for producing a mixed solution with a chain alkyl quaternary ammonium salt, first, a tertiary amine containing a branched chain alkyl tertiary amine as a main component is reacted with an excess amount of benzyl halide, and then substantially This is a method for producing a mixed quaternary ammonium salt, which is characterized by adding a linear alkyl tertiary amine containing no branched alkyl group and reacting it with a benzyl halide. Among the long-chain alkyl tertiary amines used as raw materials in the present invention, straight-chain alkyl amines have the general formula (However, R 1 and R 2 are each independently a methyl group or an ethyl group, and R 3 is a straight-chain alkyl group having 8 to 25 carbon atoms.)
branched alkyl amines, and branched chain alkyl amines have the general formula (However, R 1 and R 2 are each independently a methyl group or an ethyl group, R 4 and R 5 are each a straight-chain alkyl group, and the total number of carbon atoms in R 4 and R 5 is 6 to 23. ) is an aliphatic tertiary amine represented by In the method of the present invention, a tertiary amine whose main component is a branched alkyl tertiary amine is first quaternized with an excess amount of benzyl halide, and then a highly reactive straight chain alkyl tertiary amine is converted into a halogenated tertiary amine. Add an amount commensurate with the remaining amount of benzyl halide, or if the remaining amount of benzyl halide is less than the amount of straight-chain alkyl tertiary amine to be added, add the required amount of benzyl halide directly. By reacting a chain alkyl tertiary amine and a halogenated benzyl in stoichiometric amounts, a mixed alkyl quaternary ammonium salt with a small residual amount of unreacted amine and unreacted benzyl halide can be obtained in a short time. In the method of the present invention, the reaction between the tertiary amine and the benzyl halide is carried out in a monohydric or dihydric lower alcohol solvent such as ethanol, isopropanol, ethylene glycol, propylene glycol, etc. as is known in the art. It is possible to prevent a decrease in the reaction rate due to the increase. Furthermore, an alkaline agent or water can be added to speed up the reaction rate. As the alkaline agent, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, etc. are used. The reaction temperature can be selected within the range of 40 to 120°C, and the reaction pressure may be atmospheric pressure, but may be maintained under pressure depending on the type of reaction solvent and reaction temperature. The tertiary amine as a raw material in the present invention includes:
For example, a branched and linear mixed alkyl tertiary amine synthesized by the oxo method can be used.
In this case, since the branched chain alkyl tertiary amine and the straight chain alkyl tertiary amine have different boiling points,
The two are separated by distillation. In this fractional distillation, linear alkyl tertiary amines are allowed to be mixed in the branched alkyl tertiary amine fraction in an amount of 15 to 30% by weight, or even more in some cases. The amount of branched alkyl tertiary amine mixed in the tertiary amine fraction is preferably 1% by weight or less. As the benzyl halide, benzyl chloride and benzyl bromide are used. EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. Reference example (Quaternization reaction of linear alkyl tertiary amine) Reaction of 213.4 g (1.0 mol) of reagent N,N-dimethyldodecylamine distilled to remove impurities, 213.4 g of isopropanol, and 5.5 g of water in a glass container. The mixture was placed in a tank, heated while stirring and maintained at 60°C, and 126.6 g (1.0 mol) of benzyl chloride was added dropwise over 1 hour.
After the dropwise addition was completed, the reaction was continued at 60°C for 4 hours. By collecting a portion of the reaction solution and adding a mixture of n-hexane/methanol/water, unreacted amine and unreacted benzyl chloride are extracted into the n-hexane phase, and the n-hexane phase is analyzed by gas chromatography. The unreacted amine and unreacted benzyl chloride concentrations were measured. The unreacted amine concentration is 0.22% by weight (amine reaction rate
99.4 mol%), and the concentration of unreacted benzyl chloride was 0.1% by weight. Comparative example (branched and linear alkyl mixed tertiary amine 4)
227.4 g (1.0 mol) of N,N-dimethyl-tridecylamine synthesized from 1-dodecene, dimethylamine, and a mixed gas of hydrogen and carbon monoxide.
61.4% by weight), isopropanol 227.4g, water 6
g into a glass reaction tank, heated while stirring and kept at 60℃, and produced 139.3 g (1.1 mol) of benzyl chloride.
was added dropwise over 1 hour. After the dropwise addition was completed, the reaction was continued at 60°C for 8 hours. Unreacted amine concentration (linear amine +
branched chain amine) is 0.5% by weight (amine reaction rate 98.7
(mol%), and the unreacted benzyl chloride concentration was 2.4% by weight. Table 1 shows the change in the reaction rate between the linear alkyl tertiary amine and the branched alkyl tertiary amine during this period. It can be seen that the reaction rate of branched chain alkyl tertiary amines is extremely slow compared to that of straight chain alkyl tertiary amines. Example (Fractional quaternization reaction of branched-chain alkyl tertiary amine and straight-chain alkyl tertiary amine) N,N-dimethyl-tridecyl synthesized from 1-dodecene, dimethylamine, and hydrogen/carbon monoxide mixed gas Amine 227.4g (1.0mol) Linear chain rate
61.4% by weight), isopropanol 227.4g, water 6
g into a glass reaction tank, heated while stirring and kept at 60℃, and produced 139.3 g (1.1 mol) of benzyl chloride.
was added dropwise over 1 hour. After the dropwise addition was completed, the reaction was continued at 60°C for 8 hours. Unreacted amine concentration (linear amine +
branched chain amine) is 0.5% by weight (amine reaction rate 98.7
(mol%), and the unreacted benzyl chloride concentration was 2.4% by weight. Table 1 shows the change in the reaction rate between the linear alkyl tertiary amine and the branched alkyl tertiary amine during this period. It can be seen that the reaction rate of branched chain alkyl tertiary amines is extremely slow compared to that of straight chain alkyl tertiary amines. Example (Fractional quaternization reaction of branched-chain alkyl tertiary amine and straight-chain alkyl tertiary amine) N,N-dimethyl-tridecyl synthesized from 1-dodecene, dimethylamine, and hydrogen/carbon monoxide mixed gas The amine was distilled at a pressure of 210 mmHg using a distillation column with an inner diameter of 4 cm and 20 theoretical plates, and the boiling point was 137.5.
Fraction 1 mainly composed of branched amines at ~146.5℃
and fraction 2 consisting essentially of linear amines with a boiling point of 146.5°C. Fraction 1 consisted of 25% by weight linear amine and 75% by weight branched amine, and fraction 2 contained 99.5% by weight linear amine and 0.5% by weight branched amine. 153 g (0.67 mol) of fraction 1, 153 g of isopropanol, and 3.4 g of water were placed in a glass reaction tank, heated while stirring and kept at 60°C, and 189.9 g (1.5 mol) of benzyl chloride was added dropwise over 15 minutes. After the dropwise addition was completed, the reaction was continued at 60°C for 4 hours. The reaction rate of the linear amine was 100 mol%, and the reaction rate of the branched amine was 99.7 mol%. The residual concentration of unreacted benzyl chloride was 21.0% by weight. Next, 188 g (0.83 mol) of the linear amine of fraction 2, 188 g of isopropanol, and 3.8 g of water were added, and a second stage reaction was carried out at 60° C. for 4 hours. 1st
The unreacted residual concentration of all the amines added in the stage and second stage reactions was 0.13% by weight (amine reaction rate 99.5 mol%), and the unreacted benzyl chloride residual concentration was 0.1% by weight or less.
【表】
＊ 塩化ベンジルは１時間で滴下
[Table] * Benzyl chloride is added dropwise in 1 hour.
Claims (1)
を反応させて、直鎖アルキル第４級アンモニウム
塩と分岐鎖アルキル第４級アンモニウム塩との混
合溶液を製造する方法において、まず分岐鎖アル
キル第３級アミンを主成分とする第３級アミンを
過剰量のハロゲン化ベンジルと反応させた後、実
質的に分岐鎖アルキル基を含まない直鎖アルキル
第３級アミンを加えてハロゲン化ベンジルと反応
させることを特徴とする混合第４級アンモニウム
塩の製造方法。 ２ 直鎖アルキル第３級アミンが一般式 （但し、R1およびR2はそれぞれ独立にメチル基
またはエチル基であり、R3は炭素数が８〜25の
直鎖アルキル基である。）で示される脂肪族第３
級アミンである、特許請求の範囲第１項に記載の
方法。 ３ 分岐鎖アルキル第３級アミンが一般式 （但し、R1およびR2はそれぞれ独立にメチル基
またはエチル基であり、R4およびR5はそれぞれ
直鎖アルキル基であり、R4とR5の炭素数の合計
が６〜23である。）で示される脂肪族第３級アミ
ンである、特許請求の範囲第１項または第２項に
記載の方法。 ４ ハロゲン化ベンジルが塩化ベンジルまたは臭
化ベンジルである、特許請求の範囲第１項から第
３項のいずれかに記載の方法。[Scope of Claims] 1. A method for producing a mixed solution of a linear alkyl quaternary ammonium salt and a branched alkyl quaternary ammonium salt by reacting an aliphatic tertiary amine and a benzyl halide, First, a tertiary amine containing a branched chain alkyl tertiary amine as a main component is reacted with an excess amount of benzyl halide, and then a straight chain alkyl tertiary amine containing substantially no branched chain alkyl group is added. A method for producing a mixed quaternary ammonium salt, which comprises reacting with a benzyl halide. 2 Straight chain alkyl tertiary amine has the general formula (However, R 1 and R 2 are each independently a methyl group or an ethyl group, and R 3 is a straight-chain alkyl group having 8 to 25 carbon atoms.)
The method according to claim 1, wherein the amine is a grade amine. 3 Branched alkyl tertiary amine has the general formula (However, R 1 and R 2 are each independently a methyl group or an ethyl group, R 4 and R 5 are each a straight-chain alkyl group, and the total number of carbon atoms in R 4 and R 5 is 6 to 23. .) The method according to claim 1 or 2, wherein the aliphatic tertiary amine is an aliphatic tertiary amine represented by: 4. The method according to any one of claims 1 to 3, wherein the benzyl halide is benzyl chloride or benzyl bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3500884A JPS60178846A (en) | 1984-02-25 | 1984-02-25 | Method for producing mixed quaternary ammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3500884A JPS60178846A (en) | 1984-02-25 | 1984-02-25 | Method for producing mixed quaternary ammonium salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60178846A JPS60178846A (en) | 1985-09-12 |
| JPH0428252B2 true JPH0428252B2 (en) | 1992-05-13 |
Family
ID=12430055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3500884A Granted JPS60178846A (en) | 1984-02-25 | 1984-02-25 | Method for producing mixed quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60178846A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4026184A1 (en) * | 1990-08-18 | 1992-02-20 | Henkel Kgaa | METHOD FOR REDUCING THE REMAINING FREE ALKYLATING AGENT IN AQUEOUS SOLUTIONS OF CATIONIC SURFACES |
-
1984
- 1984-02-25 JP JP3500884A patent/JPS60178846A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60178846A (en) | 1985-09-12 |
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