JPH10168052A - Production of amine oxide - Google Patents
Production of amine oxideInfo
- Publication number
- JPH10168052A JPH10168052A JP32373496A JP32373496A JPH10168052A JP H10168052 A JPH10168052 A JP H10168052A JP 32373496 A JP32373496 A JP 32373496A JP 32373496 A JP32373496 A JP 32373496A JP H10168052 A JPH10168052 A JP H10168052A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- amine oxide
- acid
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は洗浄剤等の界面活性
剤として有用なアミンオキサイドの製造法に関し、詳し
くは保存時におけるアミンオキサイドの分解を抑制し、
匂いが良好な長期保存安定性の良いアミンオキサイドの
製造法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an amine oxide useful as a surfactant such as a detergent, and more particularly to a method for suppressing the decomposition of an amine oxide during storage.
The present invention relates to a method for producing an amine oxide having a good odor and a good long-term storage stability.
【0002】[0002]
【従来の技術及び発明が解決しようとする課題】アルキ
ルアミンオキサイドは、各種洗浄剤に補助活性剤として
使用されており、その応用範囲は、食器用洗浄剤、シャ
ンプー、衣料用洗浄剤等多岐にわたる。このアルキルア
ミンオキサイドは、アルキルサルフェート(AS)やア
ルキルエトキシサルフェート(ES)等のアニオン活性
剤、又はアルキルエトキシレートやアルキルグルコシド
(AG)等のノニオン活性剤に添加した場合に於いて、
優れた増泡効果や洗浄作用を示す。2. Description of the Related Art Alkylamine oxide is used as an auxiliary activator in various detergents, and its application range is wide-ranging, such as dishwashing detergents, shampoos and clothing detergents. . When this alkylamine oxide is added to an anionic activator such as alkyl sulfate (AS) or alkyl ethoxy sulfate (ES) or a nonionic activator such as alkyl ethoxylate or alkyl glucoside (AG),
Shows excellent foaming and cleaning effects.
【0003】この様なアミンオキサイドは、その30〜35
重量%水溶液の形態で保存されたり、あるいは凍結乾燥
して粉末状にした後、洗浄剤等の製品に添加して製品系
で保存されている。しかしながら、このような水溶液状
あるいは粉末状の保存時においてアミンオキサイドの分
解や転移反応が起こり、匂いの悪化原因となっていた。[0003] Such amine oxides are available in the range of 30 to 35
It is stored in the form of a weight% aqueous solution or freeze-dried into a powder form, added to a product such as a detergent, and stored in a product system. However, during storage in the form of an aqueous solution or a powder, the decomposition and transfer reaction of the amine oxide occur, causing the odor to deteriorate.
【0004】従って、本発明の課題は、アミンオキサイ
ドの保存時、あるいはアミンオキサイドを添加した製品
系での保存時に、アミンオキサイドの分解を抑制し、匂
いが良好な長期保存安定性の良いアミンオキサイドを製
造する方法を提供することにある。Accordingly, an object of the present invention is to provide an amine oxide which suppresses the decomposition of the amine oxide during storage of the amine oxide or during storage in a product system to which the amine oxide is added, and has a good odor and good long-term storage stability. It is to provide a method of manufacturing the.
【0005】[0005]
【課題を解決するための手段】本発明者らは上記課題を
解決すべく鋭意研究の結果、3級アミンを過酸化水素に
より酸化した後、特定のpH範囲に調整することにより
長期保存安定性の良好なアミンオキサイドが得られるこ
とを見出し本発明を完成するに到った。即ち、本発明
は、一般式(I)Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems. As a result, the tertiary amine is oxidized with hydrogen peroxide and then adjusted to a specific pH range to thereby provide a long-term storage stability. The present inventors have found that an amine oxide having a good quality can be obtained, and have completed the present invention. That is, the present invention provides a compound represented by the general formula (I):
【0006】[0006]
【化3】 Embedded image
【0007】(式中、R1は炭素数8〜26の直鎖又は分岐
鎖のアルキル基又はアルケニル基を示し、R2は炭素数1
〜26の直鎖又は分岐鎖のアルキル基又アルケニル基、或
いは炭素数1〜3のヒドロキシアルキル基を示し、R3は
炭素数1〜3のアルキル基又はヒドロキシアルキル基を
示す。)で表されるアミンオキサイドを製造するに際
し、一般式(II)Wherein R 1 represents a linear or branched alkyl or alkenyl group having 8 to 26 carbon atoms, and R 2 represents
Represents a straight-chain or branched-chain alkyl group or alkenyl group having up to 26 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and R 3 represents an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms. In producing the amine oxide represented by the general formula (II)
【0008】[0008]
【化4】 Embedded image
【0009】(式中、R1, R2及びR3は前記の意味を示
す。)で表される3級アミンと過酸化水素とを反応させ
た後、アルカリを添加してpHを9〜13に調整すること
を特徴とするアミンオキサイドの製造法を提供するもの
である。(Wherein R 1 , R 2 and R 3 have the same meanings as described above) and hydrogen peroxide, and then alkali is added to adjust the pH to 9 to 9. The present invention provides a method for producing an amine oxide, which is adjusted to 13.
【0010】[0010]
【発明の実施の形態】以下、本発明の実施の形態を詳細
に説明する。Embodiments of the present invention will be described below in detail.
【0011】本発明の原料として用いられる前記一般式
(II)で表される3級アミンとしては、ジメチルオクチ
ルアミン、ジメチル(2−エチルヘキシル)アミン、ジ
メチルデシルアミン、ジメチルドデシルアミン、ジメチ
ルトリデシルアミン、ジメチルテトラデシルアミン、ジ
メチルヘキサデシルアミン、ジメチルオクタデシルアミ
ン、ジメチル(2−オクチルドデシル)アミン、ジメチ
ルベヘニルアミン、ジヒドロキシエチルオクチルアミ
ン、ジヒドロキシエチルデシルアミン、ジヒドロキシエ
チルドデシルアミン、ジヒドロキシエチルテトラデシル
アミン、ジヒドロキシエチルオクタデシルアミン、ジヒ
ドロキシエチルベヘニルアミン、メチルジオクチルアミ
ン、メチルジ(2−エチルヘキシル)アミン、メチルオ
クチルデシルアミン、メチルジデシルアミン、メチルジ
ドデシルアミン、メチルジヘキサデシルアミン、メチル
ヘキサデシルオクタデシルアミン、メチルジオクタデシ
ルアミン、メチルジベヘニルアミン等が挙げられる。The tertiary amine represented by the general formula (II) used as a raw material of the present invention includes dimethyloctylamine, dimethyl (2-ethylhexyl) amine, dimethyldecylamine, dimethyldodecylamine, dimethyltridecylamine , Dimethyltetradecylamine, dimethylhexadecylamine, dimethyloctadecylamine, dimethyl (2-octyldodecyl) amine, dimethylbehenylamine, dihydroxyethyloctylamine, dihydroxyethyldecylamine, dihydroxyethyldodecylamine, dihydroxyethyltetradecylamine, dihydroxy Ethyl octadecylamine, dihydroxyethyl behenylamine, methyldioctylamine, methyldi (2-ethylhexyl) amine, methyloctyldecylamine Methyl didecyl amine, methyl didodecylamine, methyl dihexadecylamine, methyl hexadecyl octadecyl amine, methyl dioctadecyl amine, methyl-di-behenyl amine and the like.
【0012】これらの中では、R1が炭素数8〜18の直鎖
又は分岐鎖のアルキル基又はアルケニル基、R2が炭素数
1〜3のアルキル基又はヒドロキシアルキル基、R3が炭
素数1〜3のアルキル基又はヒドロキシアルキル基であ
るものが好ましい。Among them, R 1 is a linear or branched alkyl or alkenyl group having 8 to 18 carbon atoms, R 2 is an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms, and R 3 is a carbon or alkyl group. Those having 1 to 3 alkyl groups or hydroxyalkyl groups are preferred.
【0013】本発明において、上記一般式(II)で表さ
れる3級アミンと反応させる過酸化水素は、20〜90重量
%の水溶液が工業的に入手可能であり、このいずれの濃
度のものも本発明で使用できるが、一般には35重量%の
ものが好ましい。過酸化水素水溶液の使用量は、一般式
(II)で表される3級アミン1モルに対して、 1.0〜1.
05モル倍用いるのが好ましい。In the present invention, as the hydrogen peroxide to be reacted with the tertiary amine represented by the above general formula (II), an aqueous solution of 20 to 90% by weight is industrially available. Can also be used in the present invention, but generally 35% by weight is preferred. The amount of the aqueous hydrogen peroxide used is 1.0 to 1.1 mol per mol of the tertiary amine represented by the general formula (II).
It is preferable to use 05 mole times.
【0014】本反応の溶媒としては、一般に水が使用さ
れるが、アミンオキサイド水溶液の粘度を調節するため
に、メタノール、エタノール、イソプロパノール等の水
溶性溶媒を併用することもできる。反応温度は50〜80℃
が適当であるが、反応を促進させるためにこれより高い
温度で実施することもできる。Water is generally used as the solvent for this reaction, but a water-soluble solvent such as methanol, ethanol, or isopropanol may be used in combination to adjust the viscosity of the amine oxide aqueous solution. Reaction temperature is 50 ~ 80 ℃
Is suitable, but may be carried out at a higher temperature to accelerate the reaction.
【0015】本発明においては、上記のように一般式
(II)で表される3級アミンと過酸化水素とを反応させ
た後、アルカリを添加してpHを9〜13、好ましくは10
〜12に調整する。用いられるアルカリとしては、アルカ
リ金属の水酸化物、アルカリ金属の炭酸塩等が挙げら
れ、アルカリ金属水酸化物、特に水酸化ナトリウムが好
ましい。pHが9〜13の範囲外であるとアミンオキサイ
ドの分解を抑制することができず、長期保存時に匂い等
が悪化して好ましくない。In the present invention, after the tertiary amine represented by the general formula (II) is reacted with hydrogen peroxide as described above, the pH is adjusted to 9 to 13, preferably 10 to 13, by adding an alkali.
Adjust to ~ 12. Examples of the alkali used include an alkali metal hydroxide and an alkali metal carbonate, and an alkali metal hydroxide, particularly sodium hydroxide, is preferred. If the pH is out of the range of 9 to 13, the decomposition of the amine oxide cannot be suppressed, and the odor and the like deteriorate during long-term storage, which is not preferable.
【0016】また、本発明においては、前記一般式(I
I)で表される3級アミンと過酸化水素との反応生成物
に、1個以上の水酸基を有する炭素数4〜10の多塩基酸
又はその塩、あるいは窒素原子に結合する -CH2COOM 基
(M は水素原子、アルカリ金属、アルカリ土類金属、ア
ンモニウム又は塩基性アミノ酸基を示す)を少なくとも
2個有するアミノポリカルボン酸又はその塩から選ばれ
る1種又は2種以上の金属封鎖剤を添加すると、アミン
オキサイドの分解を更に抑制することができ好ましい。In the present invention, the compound represented by the general formula (I
The reaction products of tertiary amine with hydrogen peroxide represented by I), -CH 2 binds to a polybasic acid or a salt or nitrogen atom, 4 to 10 carbon atoms having one or more hydroxyl groups COOM One or more sequestering agents selected from aminopolycarboxylic acids having at least two groups (M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid group) or salts thereof; The addition is preferable because the decomposition of the amine oxide can be further suppressed.
【0017】1個以上の水酸基を有する炭素数4〜10の
多塩基酸又はその塩としては、クエン酸、リンゴ酸、酒
石酸及びこれらのナトリウム塩、カリウム塩等のアルカ
リ金属塩等が挙げられ、窒素原子に結合する -CH2COOM
基を少なくとも2個有するアミノポリカルボン酸又はそ
の塩としては、エチレンジアミンテトラ酢酸、ニトリロ
トリ酢酸、ジエチレントリアミンペンタアセテート及び
これらのナトリウム塩、カリウム塩等のアルカリ金属塩
等が挙げられる。これらの金属封鎖剤の中ではクエン
酸、リンゴ酸、酒石酸、エチレンジアミンテトラ酢酸又
はこれらの塩が特に好ましい。Examples of the polybasic acid having at least one hydroxyl group and having 4 to 10 carbon atoms or a salt thereof include citric acid, malic acid, tartaric acid, and alkali metal salts such as sodium salt and potassium salt thereof. -CH 2 COOM which binds to a nitrogen atom
Examples of the aminopolycarboxylic acid having at least two groups or a salt thereof include ethylenediaminetetraacetic acid, nitrilotriacetic acid, diethylenetriaminepentaacetate, and alkali metal salts such as sodium salt and potassium salt thereof. Among these sequestering agents, citric acid, malic acid, tartaric acid, ethylenediaminetetraacetic acid or salts thereof are particularly preferred.
【0018】これらの金属封鎖剤の添加量は、アミンオ
キサイドに対して0.005 〜3重量%が好ましく、0.01〜
0.5 重量%が更に好ましい。The amount of the sequestering agent added is preferably 0.005 to 3% by weight based on the amine oxide, and is preferably 0.01 to 3% by weight.
0.5% by weight is more preferred.
【0019】本発明においては、3級アミンと過酸化水
素を反応させた後、上記のような処理を行うことにより
アミンオキサイドの分解や転移反応を抑制することがで
きる。本発明によると、アミンオキサイドを水溶液の形
態で保存する時はもちろん、アミンオキサイド水溶液を
凍結乾燥等により乾燥して粉末状とした後、洗浄剤等の
製品に添加して製品系で保存する場合にもアミンオキサ
イドの分解や転移反応を抑制することができる。特に、
アミンオキサイドを水分含量12重量%以下、好ましくは
8重量%以下に乾燥し粉末状とした場合にはアミンオキ
サイドの分解が非常に大きくなるが、本発明の処理を行
うことによりこの分解を抑制することができ、非常に好
ましい。In the present invention, the decomposition and transfer reaction of the amine oxide can be suppressed by performing the above-mentioned treatment after reacting the tertiary amine with hydrogen peroxide. According to the present invention, not only when the amine oxide is stored in the form of an aqueous solution, but also when the amine oxide aqueous solution is dried into a powder form by freeze-drying or the like, and then added to a product such as a detergent and stored in a product system. In addition, the decomposition and transfer reaction of the amine oxide can be suppressed. Especially,
When the amine oxide is dried to a water content of 12% by weight or less, preferably 8% by weight or less to form a powder, the decomposition of the amine oxide becomes extremely large, but the decomposition of the amine oxide is suppressed by the treatment of the present invention. Can be very favorable.
【0020】[0020]
【実施例】以下、本発明を実施例により更に詳細に説明
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。尚、例中の%は特記しない限り重量基準である。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. The percentages in the examples are on a weight basis unless otherwise specified.
【0021】実施例1〜2及び比較例1〜2 ラウリルジメチルアミン(Mw246)2460gとイオン交換水
4060gを温度計、攪拌器、冷却管、滴下ロートを備えた
20リットル容5ツ口フラスコに仕込み80℃まで昇温し
た。その後、35%過酸化水素水溶液 971gを3時間かけ
て滴下した後に、5時間熟成を行い反応を終了した。生
成物は35%のラウリルジメチルアミンオキサイドを含む
水溶液(pH7)であり、この水溶液中のラウリルジメ
チルアミン含量は200 ppm であった。Examples 1 and 2 and Comparative Examples 1 and 2 2460 g of lauryl dimethylamine (Mw246) and deionized water
4060 g was equipped with a thermometer, stirrer, cooling tube and dropping funnel
The mixture was charged into a 20-liter 5-neck flask and heated to 80 ° C. Thereafter, 971 g of a 35% aqueous hydrogen peroxide solution was added dropwise over 3 hours, followed by aging for 5 hours to terminate the reaction. The product was an aqueous solution (pH 7) containing 35% lauryl dimethylamine oxide, and the aqueous solution had a lauryl dimethylamine content of 200 ppm.
【0022】得られたラウリルジメチルアミンオキサイ
ドの水溶液 600gを200ml ビーカー4個にそれぞれ約 1
50gずつ入れ、10%水酸化ナトリウム又は10%塩酸水溶
液を用いてpHを4,7,10,12に調整した。その後、
各pHに調整したアミンオサキイド水溶液を、pH調整
液に対して3分割し、 100mlの蓋付きガラスビンに入
れ、それぞれ30℃, 40℃及び50℃の恒温槽にて1カ月保
存した。保存後のアミンオキサイド水溶液について、 1
H−NMRにより酸素の脱離により生成したラウリルジ
メチルアミン含量を測定した。結果を表1に示す。About 600 g of the obtained aqueous solution of lauryl dimethylamine oxide was added to four 200 ml beakers each for about 1 part.
50 g each was added, and the pH was adjusted to 4, 7, 10, 12 using 10% sodium hydroxide or 10% aqueous hydrochloric acid. afterwards,
The amine osakiide aqueous solution adjusted to each pH was divided into three parts with respect to the pH-adjusted solution, placed in a 100 ml glass bottle with a lid, and stored for one month in a thermostat at 30 ° C, 40 ° C and 50 ° C, respectively. About the amine oxide aqueous solution after storage, 1
The content of lauryl dimethylamine formed by elimination of oxygen was measured by H-NMR. Table 1 shows the results.
【0023】[0023]
【表1】 [Table 1]
【0024】実施例3〜8及び比較例3〜8 実施例1と同様の方法により35%のラウリルジメチルア
ミンオキサイドを含むpH7の水溶液を得た。この水溶
液を以下に示すように調整して下記サンプル1〜12を得
た後、24時間凍結乾燥を行い、表2に示す水分含量のサ
ンプルを得た。凍結乾燥後のサンプルを50ml蓋付きビン
に25g添加して密閉し、80℃で24時間保存して熱安定性
試験を行った。凍結乾燥直後及び24時間保存後、酸素の
脱離により生成したラウリルジメチルアミンの含量を実
施例1と同様に測定した。結果を表2に示す。Examples 3 to 8 and Comparative Examples 3 to 8 An aqueous solution of pH 7 containing 35% lauryl dimethylamine oxide was obtained in the same manner as in Example 1. This aqueous solution was adjusted as shown below to obtain the following samples 1 to 12, and then lyophilized for 24 hours to obtain samples having the water contents shown in Table 2. 25 g of the lyophilized sample was added to a 50 ml bottle with a lid, sealed, stored at 80 ° C. for 24 hours, and subjected to a thermal stability test. Immediately after lyophilization and after storage for 24 hours, the content of lauryl dimethylamine produced by elimination of oxygen was measured in the same manner as in Example 1. Table 2 shows the results.
【0025】サンプル1:未調整品、pH7.0 (比較例
3) サンプル2:ラウリルジメチルアミンオキサイド水溶液
100gにクエン酸を 0.1g添加し溶解した。pHは6.6
であった(比較例4)。 サンプル3:ラウリルジメチルアミンオキサイド水溶液
100gにクエン酸を0.1g添加した後、10%水酸化ナト
リウム水溶液でpHを12に調整した(実施例3)。 サンプル4:ラウリルジメチルアミンオキサイド水溶液
100gを10%水酸化ナトリウム水溶液でpH12に調整し
た(実施例4)。 サンプル5:ラウリルジメチルアミンオキサイド水溶液
100gにクエン酸を0.1g添加した後、10%水酸化ナト
リウム水溶液でpHを9に調整した(実施例5)。Sample 1: Unadjusted product, pH 7.0 (Comparative Example 3) Sample 2: Lauryl dimethylamine oxide aqueous solution
0.1 g of citric acid was added to and dissolved in 100 g. pH 6.6
(Comparative Example 4). Sample 3: Lauryl dimethylamine oxide aqueous solution
After adding 0.1 g of citric acid to 100 g, the pH was adjusted to 12 with a 10% aqueous sodium hydroxide solution (Example 3). Sample 4: Lauryl dimethylamine oxide aqueous solution
100 g was adjusted to pH 12 with a 10% aqueous sodium hydroxide solution (Example 4). Sample 5: Lauryl dimethylamine oxide aqueous solution
After 0.1 g of citric acid was added to 100 g, the pH was adjusted to 9 with a 10% aqueous sodium hydroxide solution (Example 5).
【0026】サンプル6:ラウリルジメチルアミンオキ
サイド水溶液 100gにエチレンジアミンテトラ酢酸(ED
TA) を0.1 g添加した。pHは6.6 であった(比較例
5)。 サンプル7:ラウリルジメチルアミンオキサイド水溶液
100gにエチレンジアミンテトラ酢酸(EDTA) を0.1 g
添加した後、10%水酸化ナトリウム水溶液でpHを12に
調整した(実施例6)。Sample 6: 100 g of an aqueous solution of lauryl dimethylamine oxide was added to ethylenediaminetetraacetic acid (ED
TA) was added in an amount of 0.1 g. The pH was 6.6 (Comparative Example 5). Sample 7: aqueous solution of lauryl dimethylamine oxide
0.1 g of ethylenediaminetetraacetic acid (EDTA) to 100 g
After the addition, the pH was adjusted to 12 with a 10% aqueous sodium hydroxide solution (Example 6).
【0027】サンプル8:ラウリルジメチルアミンオキ
サイド水溶液 100gにリンゴ酸を0.1g添加した。pH
は6.7 であった(比較例6)。 サンプル9:ラウリルジメチルアミンオキサイド水溶液
100gにリンゴ酸を0.1g添加した後、10%水酸化ナト
リウム水溶液でpHを12に調整した(実施例7)。Sample 8: 0.1 g of malic acid was added to 100 g of an aqueous solution of lauryl dimethylamine oxide. pH
Was 6.7 (Comparative Example 6). Sample 9: aqueous solution of lauryl dimethylamine oxide
After adding 0.1 g of malic acid to 100 g, the pH was adjusted to 12 with a 10% aqueous sodium hydroxide solution (Example 7).
【0028】サンプル10:ラウリルジメチルアミンオキ
サイド水溶液 100gに酒石酸を0.1 g添加した。pHは
6.6 であった(比較例7)。 サンプル11:ラウリルジメチルアミンオキサイド水溶液
100gに酒石酸を0.1 g添加した後、10%水酸化ナトリ
ウム水溶液でpHを12に調整した(実施例8)。 サンプル12:ラウリルジメチルアミンオキサイド水溶液
100gに乳酸を0.1 g添加した。pHは6.6 であった
(比較例8)。Sample 10: 0.1 g of tartaric acid was added to 100 g of aqueous solution of lauryl dimethylamine oxide. pH is
6.6 (Comparative Example 7). Sample 11: Lauryl dimethylamine oxide aqueous solution
After 0.1 g of tartaric acid was added to 100 g, the pH was adjusted to 12 with a 10% aqueous sodium hydroxide solution (Example 8). Sample 12: Lauryl dimethylamine oxide aqueous solution
0.1 g of lactic acid was added to 100 g. The pH was 6.6 (Comparative Example 8).
【0029】[0029]
【表2】 [Table 2]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 藤生 明 和歌山県和歌山市湊1334 花王株式会社研 究所内 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Akira Fujio 1334 Minato, Wakayama City, Wakayama Pref.
Claims (5)
基又はアルケニル基を示し、R2は炭素数1〜26の直鎖又
は分岐鎖のアルキル基又アルケニル基、或いは炭素数1
〜3のヒドロキシアルキル基を示し、R3は炭素数1〜3
のアルキル基又はヒドロキシアルキル基を示す。)で表
されるアミンオキサイドを製造するに際し、一般式(I
I) 【化2】 (式中、R1, R2及びR3は前記の意味を示す。)で表され
る3級アミンと過酸化水素とを反応させた後、アルカリ
を添加してpHを9〜13に調整することを特徴とするア
ミンオキサイドの製造法。1. A compound of the general formula (I) (Wherein, R 1 represents a linear or branched alkyl or alkenyl group having 8 to 26 carbon atoms, and R 2 represents a linear or branched alkyl or alkenyl group having 1 to 26 carbon atoms, or Number 1
Represents 3 to 3 hydroxyalkyl groups, and R 3 has 1 to 3 carbon atoms.
Represents an alkyl group or a hydroxyalkyl group. In producing the amine oxide represented by the general formula (I)
I) (Wherein, R 1 , R 2 and R 3 have the same meanings as above), and after reacting the tertiary amine with hydrogen peroxide, the pH is adjusted to 9 to 13 by adding an alkali. A method for producing an amine oxide.
18の直鎖又は分岐鎖のアルキル基又はアルケニル基、R2
が炭素数1〜3のアルキル基又はヒドロキシアルキル
基、R3が炭素数1〜3のアルキル基又はヒドロキシアル
キル基である請求項1記載の製造法。2. In the general formula (I), R 1 has from 8 to 8 carbon atoms.
18 linear or branched alkyl or alkenyl groups, R 2
Is an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms, and R 3 is an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms.
と過酸化水素との反応生成物に、1個以上の水酸基を有
する炭素数4〜10の多塩基酸又はその塩、あるいは窒素
原子に結合する -CH2COOM 基(M は水素原子、アルカリ
金属、アルカリ土類金属、アンモニウム又は塩基性アミ
ノ酸基を示す)を少なくとも2個有するアミノポリカル
ボン酸又はその塩から選ばれる1種又は2種以上の金属
封鎖剤を添加する請求項1又は2記載の製造法。3. A polybasic acid having at least one hydroxyl group and having 4 to 10 carbon atoms or a salt thereof, or a reaction product of the tertiary amine represented by the general formula (II) and hydrogen peroxide, or One selected from aminopolycarboxylic acids or salts thereof having at least two -CH 2 COOM groups (M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid group) bonded to a nitrogen atom 3. The method according to claim 1, wherein two or more sequestering agents are added.
酸、エチレンジアミンテトラ酢酸又はこれらの塩である
請求項3記載の製造法。4. The method according to claim 3, wherein the sequestering agent is citric acid, malic acid, tartaric acid, ethylenediaminetetraacetic acid or a salt thereof.
に対して0.005 〜3重量%である請求項3又は4記載の
製造法。5. The process according to claim 3, wherein the amount of the sequestering agent is 0.005 to 3% by weight based on the amine oxide.
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003096048A (en) * | 2001-09-27 | 2003-04-03 | Nof Corp | Production method of amine oxide |
JP2007204400A (en) * | 2006-01-31 | 2007-08-16 | Lion Akzo Kk | Method for producing amine oxide |
WO2007102568A1 (en) * | 2006-03-08 | 2007-09-13 | Kao Corporation | Method for producing nitrogen-containing compound |
JP2010064964A (en) * | 2008-09-09 | 2010-03-25 | Kao Corp | Method of producing amine oxide |
JP2015528808A (en) * | 2012-07-24 | 2015-10-01 | ザ プロクター アンド ギャンブルカンパニー | Continuous process for producing amine oxides |
-
1996
- 1996-12-04 JP JP32373496A patent/JP3926414B2/en not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003096048A (en) * | 2001-09-27 | 2003-04-03 | Nof Corp | Production method of amine oxide |
JP2007204400A (en) * | 2006-01-31 | 2007-08-16 | Lion Akzo Kk | Method for producing amine oxide |
WO2007102568A1 (en) * | 2006-03-08 | 2007-09-13 | Kao Corporation | Method for producing nitrogen-containing compound |
US7754923B2 (en) | 2006-03-08 | 2010-07-13 | Kao Corporation | Method for producing nitrogen-containing compound |
JP2010064964A (en) * | 2008-09-09 | 2010-03-25 | Kao Corp | Method of producing amine oxide |
JP2015528808A (en) * | 2012-07-24 | 2015-10-01 | ザ プロクター アンド ギャンブルカンパニー | Continuous process for producing amine oxides |
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JP3926414B2 (en) | 2007-06-06 |
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