JPH10330338A - Production of n-alkylamidoalkanol - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful as a raw material for perfumeries, etc., and reduced in an unreacted amine and other volatile impurities by blowing steam or an inactive gas in an N-alkylamidoalkanol during or after an amidation reaction. SOLUTION: This method for producing (C) an N-alkylamidoalkanol of formula IV comprises reacting (A) an amine of formula I (R<1> is a 6-22C linear chain or branched alkyl, an alkenyl, etc.; R<2> is H, a 1-22C liner chain or branched alkyl, an alkenyl, etc.), with (B) a lactone of formula II (R<3> is a 1-5C linear chain or branched alkylene) or an ω-hydroxycarboxylic acid of formula III (R<4> is H, a 1-4C linear chain or branched alkyl) or its ester. Therein, stem or an inactive gas is blown in the reaction solution during or after the amidation reaction. The component A and B are preferably reacted with each other in a component A/component B molar ratio of 0.8-1.2 at a reaction temperate of 50-200 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an N-alkylamide alkanol and a sulfate or a salt thereof, and more particularly, to a method for removing a volatile odorant efficiently and a N-alkylamide alkanol sulfate. The present invention relates to a method for producing an N-alkylamide alkanol which has a good odor and no problem in safety even when the alkanol is used.

[0002]

2. Description of the Related Art As a cleaning agent for hair, body, tableware and the like, N-surfactant which is excellent in foaming property and highly safe.
Alkyl amide alkanol sulfates have been reported (JP-A-7-267917). This surfactant is obtained by further neutralizing an N-alkylamide alkanol sulfate obtained by sulfating an N-alkylamide alkanol with a sulfating agent. However, the N-alkylamide alkanol sulfate obtained in this manner has an odor component and is unsuitable for a cosmetic raw material as it is. As this odor component, unreacted amines and volatile impurities derived from raw materials are considered, and it is necessary to efficiently remove these odor components.

[0003] As a method of purifying an anionic surfactant,
Example in which air, an inert gas or water vapor is blown simultaneously when drying a water slurry of an anionic surfactant in a thin film evaporator, thereby simultaneously reducing drying and unreacted volatile components. (JP-A-5-331496). However, if an attempt is made to perform a distillation operation while blowing air, an inert gas, or steam into an aqueous solution of a surfactant having a high foaming property such as an N-alkylamide alkanol sulfate salt, violence is caused by the high foaming property. Bubbling occurs, making it difficult to continue the distillation operation. In order to suppress such intense foaming and complete the concentration, it is necessary to reluctantly add silicone or the like.
-The original foaming property of the alkylamide alkanol sulfate is impaired, which is not desirable in terms of performance, and may require post-treatment or the like.

[0004]

As a method for purifying N-alkylamide alkanols, crystallization using a solvent or the like can be considered, but it is not suitable for use in industrial applications requiring a large amount of supply. . Therefore, the object of the present invention can be carried out without the above-mentioned inconvenience and by a simple operation. Even when the N-alkylamide alkanol sulfate salt is used, the odor is good and it can be used as a cosmetic raw material. An object of the present invention is to provide a production method capable of obtaining an N-alkylamide alkanol and a sulfate or a salt thereof, which can be produced and have no problem in safety.

[0005]

Under these circumstances, the present inventors have conducted intensive studies and as a result, have found that when producing N-alkylalkanols, N-alkylamides are produced during or after the amidation reaction. By blowing steam or an inert gas into the alkanol or its alkylene oxide adduct, an odor component derived from the raw material,
That is, it has been found that unreacted amines and other volatile impurities can be reduced, and even when the obtained N-alkylamide alkanol is converted to a sulfate, a product having a good odor can be obtained. It was completed.

That is, the present invention provides the following general formula (I)

[0007]

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[0008] [In the formula, R ¹ represents a linear or branched alkyl group, alkenyl group, hydroxyalkyl group or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group, having 6 to 22 carbon atoms, R ² Represents a hydrogen atom or a linear or branched alkyl group, alkenyl group, hydroxyalkyl group having 1 to 22 carbon atoms, or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group. And an amine represented by the general formula (II)

[0009]

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[Wherein, R ³ represents a linear or branched alkylene group having 1 to 5 carbon atoms. A lactone represented by
Or the general formula (III)

[0011]

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[0012] [wherein, R ³ is as defined above, R ⁴
Represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. With an ω-hydroxycarboxylic acid or an ester thereof represented by the general formula (IV)

[0013]

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Wherein R ¹ , R ² and R ³ have the same meaning as described above. Or an alkylene oxide added to the N-alkylamide alkanol represented by the general formula (V):

[0015]

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[Wherein, R ¹ , R ² and R ³ have the same meanings as described above, R ⁵ represents a linear or branched alkylene group having 2 to 3 carbon atoms, and n R ^5s are the same. But they may be different. n is an arbitrary number in the range of 0 <n ≦ 50 indicating the average number of moles of alkylene oxide added. In obtaining an alkylene oxide adduct of an N-alkylamide alkanol represented by the following formula, during or after the amidation reaction:
Another object of the present invention is to provide a production method characterized by blowing steam or an inert gas into an alkylene oxide adduct of N-alkylamide alkanol.

[0017]

According to the present invention, an amine represented by the above general formula (I) and a lactone represented by the general formula (II) or ω-hydroxyl represented by the general formula (III) are used. By reacting with a carboxylic acid or its ester,
An N-alkylamide alkanol represented by the general formula (IV) is obtained. When reacting the amine of general formula (I) with the lactone of general formula (II), the reaction ratio (molar ratio of general formula (I) / general formula (II)) is preferably 0.8 to 1.2, and the reaction temperature is
The temperature is preferably from 50 to 200 ° C, and the reaction time is preferably from 1 to 15 hours. On the other hand, the amine of the general formula (I) and the amine of the general formula (III)
When the ω-hydroxycarboxylic acid or ester thereof is reacted, the reaction ratio (general formula (I) / general formula (III))
Is preferably 0.8 to 1.2, and the reaction temperature is 50 to 200.
C. is preferable, and the reaction time is preferably 1 to 15 hours.

R ¹ in the above formula represents a linear or branched alkyl group, alkenyl group, hydroxyalkyl group having 6 to 22 carbon atoms, or an alkylphenyl group having 8 to 12 carbon atoms in the alkyl group. . Specifically, hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, isostearyl group, eicosyl group, docosyl group, oleyl group, 2-ethylhexyl group, 12-hydroxydodecyl group, And a nonylphenyl group. Among these, a linear or branched alkyl group having 6 to 22 carbon atoms is preferable in terms of foaming property,
In particular, a straight-chain alkyl group having 8 to 18 carbon atoms, and furthermore, having 10 to
Fourteen straight chain alkyl groups are preferred.

R ² in the above general formula is a hydrogen atom, a linear or branched alkyl group having 1 to 22 carbon atoms, an alkenyl group, a hydroxyalkyl group, or an alkyl group having 8 to 12 carbon atoms. Shows an alkylphenyl group. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a hydroxyethyl group, and the functional groups exemplified above for R ¹ . Among these, a hydrogen atom is particularly preferable from the viewpoints of foaming properties, safety and chemical stability.

More specifically, the amine of the general formula (I) includes octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, methyloctylamine, decylmethylamine, dodecylmethylamine, Methyltetradecylamine, hexadecylmethylamine, methyloctadecylamine and the like can be mentioned.

R ³ in the above formula represents a linear or branched alkylene group having 1 to 5 carbon atoms. In particular,
Methylene group, ethylene group, propylene group, butylene group,
Examples include a pentylene group and a branched 2-methylbutylene group represented by —CH ₂ CH (CH ₃ ) CH ₂ CH ₂ —, and particularly, a methylene group or a branched chain in view of foamability and chemical stability. A 2-methylbutylene group is preferred. Most preferred is a methylene group. Specific examples of the lactone of the general formula (II) having such a functional group include β-propiolactone, γ-butyrolactone, δ-valerolactone,
Methyl-δ-valerolactone, ε-caprolactone, 2
-Methyl-γ-butyrolactone.

R ⁴ in the general formula (III) represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, and an isobutyl group. Specific examples of the ω-hydroxycarboxylic acid of general formula (III) and esters thereof include lactic acid, glycolic acid, 2-hydroxypropionic acid, 3-hydroxybutyric acid, 4-hydroxypentanoic acid and 4-hydroxy-3-methylpentane acid,
5-Hydroxyhexanoic acid, and methyl ester, ethyl ester, propyl ester, butyl ester thereof and the like can be mentioned.

The N-alkylamide alkanol represented by the general formula (IV) can have an alkylene oxide added as required. This is accomplished by reacting an N-alkylamide alkanol with an alkylene oxide in the presence of a known alkali or acid catalyst to obtain a compound represented by the general formula (V):
Which is an alkylene oxide adduct of an N-alkylamide alkanol represented by the formula: R ⁵ in the general formula (V) represents a linear or branched alkylene group having 2 to 3 carbon atoms, which is specifically an ethylene group or a linear or branched propylene group.
n represents the average number of moles of alkylene oxide added, 0 <
Although it is an arbitrary number of n ≦ 50, an arbitrary number of 0 <n ≦ 10 is particularly preferable in terms of foaming property, safety and chemical stability.
The n number of R ⁵ may be the same or different. However, the above-mentioned general formula (I) containing no oxyalkylene group
N-alkylamidoalkanols represented by V) are more preferred.

Specific examples of the N-alkylamide alkanol represented by the general formula (IV) or the alkylene oxide adduct of the N-alkylamide alkanol represented by the general formula (V) include the following compounds.

[0025]

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[0026]

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[0027]

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The crude reaction solution of N-alkylamide alkanol or the alkylene oxide adduct of N-alkylamide alkanol thus obtained contains unreacted amine and volatile impurities derived from the raw materials. In the present invention, the unreacted amine and volatile impurities contained in the raw material are efficiently removed by blowing steam or an inert gas during the amidation reaction or before entering the sulfation step after the reaction. Things.

In the present invention, the injection of steam or an inert gas may be performed during the amidation reaction, but this operation is preferably performed after the reaction rate reaches 60% or more. More preferably, it is after 80% or more. This is because if steam or an inert gas is blown in at a very low reaction rate, the amount of unreacted amine to be removed is large and the yield is low. In addition, when the alkylene oxide is added to the N-alkylamide alkanol, steam or an inert gas may be blown before or after the addition reaction. The blowing is preferably performed using an evaporator, and such an evaporator may be a batch type or an apparatus for forming a thin film. In the case of an apparatus for forming a thin film, a natural thin film forming apparatus such as a falling film type or an apparatus for forcibly forming a thin film can be used.

In the present invention, the operating pressure at the time of blowing is preferably under vacuum, more preferably 200 mmHg or less.
The operating temperature is preferably from 100 to 200C, more preferably from 130 to 150C. This is because the higher the operating temperature, the higher the vapor pressure can be, but if it is too high, there is a risk of coloring. Further, when the temperature is low, the melting point of the N-alkylamide alkanol is relatively high, so that the crude reaction solution may be solidified. The substance to be blown may be water vapor or an inert gas such as nitrogen, argon, helium, or carbon dioxide gas.However, in order to maintain fluidity when the evaporated unreacted amine and impurities are condensed in the condenser, water vapor is preferable. .

In the present invention, when steam is blown, the amount of steam blown is preferably 0.01 or more and 10 or less, more preferably 0.1 or more and 10 or less in terms of the weight ratio of steam to the amidated crude reaction solution. When the weight ratio is less than 0.01, the reduction in the partial pressure of the volatile substance is small, and the removal efficiency is low. On the other hand, even if the weight ratio between the steam and the amidation reaction liquid is 10 or more, the removal efficiency does not change, which is economically disadvantageous. When an inert gas is used, the blowing amount of the inert gas is preferably 0.01 or more and 10 or less in terms of the weight ratio of the inert gas and the crude amidation reaction solution. The blowing speed of the steam or the inert gas is not particularly limited.

The N-alkylamide alkanol or the alkylene oxide adduct of N-alkylamide alkanol thus obtained is sulfated with a sulfating agent or neutralized with a basic substance after sulfation. And the following general formula (VI)

[0033]

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[Wherein, R ¹ , R ² , R ³ and R ⁵ have the same meaning as described above, and n R ^5s may be the same or different. n is an arbitrary number from 0 to 50 indicating the average number of moles of alkylene oxide added, and M represents a hydrogen atom or a cation. ] Or a salt thereof. Here, as the cation, alkali metal, alkaline earth metal, ammonium, alkanol ammonium having 2 to 9 carbon atoms, alkyl ammonium or alkenyl ammonium having 1 to 22 carbon atoms, alkyl or alkenyl substitution having 1 to 18 carbon atoms Pyridinium, basic amino acids and the like.

When the N-alkylamide alkanol is sulfated, the method is not particularly limited, but chlorosulfonic acid, liquid SO ₃ or SO ₃ gas, fuming sulfuric acid and concentrated sulfuric acid can be used as the sulfating agent. It is particularly preferable to use chlorosulfonic acid in consideration of reactivity, product hue, and the like. In the sulfation reaction, a solvent may or may not be used, but the use of a solvent improves the reactivity,
A high reaction rate is obtained, and solidification and thickening are suppressed,
Operation becomes easy. Preferred solvents are straight-chain, branched-chain or cyclic alkanes having 5 to 10 carbon atoms, and hexane, cyclohexane and the like are particularly preferable from the viewpoint of boiling point and industrial availability.

Examples of the basic substance used for neutralization include hydroxides of alkali metals or alkaline earth metals, carbonates or bicarbonates, ammonia, alkanolamines having 2 to 9 carbon atoms, and 1 to 22 carbon atoms. Alkylamines or alkenylamines, alkyl or alkenyl substituted pyridines having 1 to 18 carbon atoms in total, or basic amino acids.

[0037]

According to the present invention, unreacted amine and other volatile components as odor components can be efficiently removed from a crude reaction solution of N-alkylamide alkanol, and N-alkylamide having a good smell can be removed. Alkanol and N-alkylamide alkanol sulfate or a salt thereof can be produced. The N-alkylamide alkanol sulfate thus obtained can be suitably used as a raw material for cosmetics and the like.

[0038]

The present invention will be described below in more detail with reference to examples and comparative examples. However, these examples do not limit the present invention. In addition, the odor evaluation of the N-alkylamide alkanol or the N-alkylamide alkanol sulfate in Examples and Comparative Examples of the present invention was performed by a sensory evaluation by a panelist. Table 1 shows odor evaluation criteria for N-alkylamide alkanols, and Table 2 shows odor evaluation criteria for N-alkylamide alkanol sulfates.

[0039]

[Table 1]

[0040]

[Table 2]

Example 1 In a 2 liter four-necked flask equipped with a stirrer, a condenser, a thermometer and a dropping funnel, 439. 69.2% aqueous solution of glycolic acid was added.
60 g (4.0 mol) was charged, and water was distilled off under reduced pressure.
Thereto, 743 g (4.0 mol) of dodecylamine was added dropwise over 1 hour and 30 minutes. After that, stirring was continued while maintaining the inside of the system at 100 ° C., and the reaction and aging were performed for 5 hours.
Reached 94.8%. After raising the temperature of the crude reaction solution to 150 ° C., the pressure in the system was set to 50 mmHg, and the blowing amount was set to 100 g / hr, steam was blown until the total blowing amount became 0.5 in weight ratio with the crude reaction solution. And cooled. The N- thus obtained
The odor of dodecyl glycolamide was evaluated. Furthermore,
In a 2 liter four-necked flask equipped with a stirrer, a condenser, a thermometer and a dropping funnel, 100 g (0.41 mol) of this N-dodecyl glycolamide was dispersed in 1000 g of N-hexane. 47.88 g (0.41 mol) of acid
Was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred for 2 hours, and then the degree of sulfation was measured by high performance liquid chromatography. As a result, the rate of sulfation was 99.5%. After neutralizing the reaction mixture with an aqueous sodium hydroxide solution, water and ethanol were added thereto, and N 2 was separated using a separating funnel.
After separating from the hexane phase, a part of water and the solvent were distilled off under reduced pressure to obtain about 30% aqueous solution of sodium N-dodecyl-1-sulfoxyacetamide. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 2 A crude reaction solution of N-decylglycolic acid amide was obtained in the same manner as in Example 1 except that decylamine was used in place of dodecylamine. The conversion was 93.3%. As in Example 1, the crude reaction solution was heated to 150 ° C., the pressure in the system was set to 50 mmHg, and the injection amount was set to 100 g / hr, so that the total injection amount was 1.0 in terms of the weight ratio with the crude reaction product. Water vapor was blown to the extent necessary, followed by cooling. The N- thus obtained
The odor of decyl glycolamide was evaluated. Further, by operating in the same manner as in Example 1, an aqueous solution of about 30% sodium N-decyl-1-sulfoxyacetamide was obtained. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 3 The crude reaction solution of N-dodecylglycolic acid amide obtained in Example 1 was heated to a system temperature of 120 ° C. and a system pressure of 50 mmHg, and the total injection amount was 0.1% by weight with respect to the crude reaction product. And then cooled. Thereafter, the odor was evaluated. Further, the same operation as in Example 1 was performed to obtain an about 30% aqueous solution of sodium N-dodecyl-1-sulfoxyacetamide. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 4 An internal temperature of 150 ° C. and an internal pressure of 100 using a forced thin film forming apparatus.
The pressure was set to mmHg, and the N-dodecylglycolic acid amide crude reaction liquid obtained in Example 1 was continuously fed, and the ratio of the steam blowing rate to the feed rate of the crude reaction product was set to 8 in weight ratio. After blowing water vapor, it was cooled and the odor was evaluated. Further, the same operation as in Example 1 was performed to obtain an about 30% aqueous solution of sodium N-dodecyl-1-sulfoxyacetamide. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 5 Using β-propiolactone and methyloctylamine,
In other respects, the reaction and aging were carried out for 8 hours in the same manner as in Example 1. The conversion was 100%. This reaction is
The temperature was raised to 50 ° C., the pressure in the system was set to 100 mmHg, and the amount of blowing was set to 100 g / hr. Water vapor was blown until the total amount of blowing became 0.5 in terms of the weight ratio with the reactants, followed by cooling.
The thus obtained N-octyl-N-methyl-3-
The odor of hydroxypropylamide was evaluated. Furthermore,
In the same manner as in Example 1, an approximately 30% aqueous solution of sodium N-octyl-N-methyl-3-sulfoxypropylamide was obtained. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 6 The N-decylglycolic acid amide crude reaction solution obtained in Example 2 was subjected to a system temperature of 130 ° C. and a system pressure of 50 mmHg.
Water vapor was blown until the total blow-in amount became 1.0 in terms of the weight ratio with the crude reaction product, and then 3 mol of ethylene oxide was added on average, followed by cooling. The N- thus obtained
The odor of decyl-sulfoxypolyoxyethyleneacetamide was evaluated. Further, in the same manner as in Example 1, about 30
% Sodium N-decyl-sulfoxypolyoxyethyleneacetamide aqueous solution was obtained. Table 3 shows the treatment conditions and the evaluation results of the odor.

Example 7 The reaction and the aging were carried out for 5 hours by operating in the same manner as in Example 1 except that methyltetradecylamine was used instead of dodecylamine. The conversion was 95.1%. After adding an average of 2 moles of ethylene oxide to the reaction product, 15
The temperature was raised to 0 ° C, the internal pressure was set to 200 mmHg,
Water vapor was blown at a setting of 100 g / hr until the total blow-in amount became 1.0 in terms of the weight ratio with the crude reaction product, followed by cooling. The odor of the thus obtained N-tetradecyl-N-methyl-polyoxyethyleneacetamide was evaluated. Further, about 30% of N-tetradecyl-
An aqueous solution of sodium N-methyl-sulfoxypolyoxyethyleneacetamide was obtained. Table 3 shows the treatment conditions and the evaluation results of the odor.

[0048]

[Table 3]

Comparative Example 1 The crude reaction solution of N-dodecylglycolic acid amide obtained in Example 1 was further aged at normal pressure for 5 hours corresponding to the blowing time in Example 1, without blowing steam. The odor of the obtained N-dodecyl glycolamide was evaluated. Further, in the same manner as in Example 1, about 30
% N-dodecyl-1-sulfoxyacetamide sodium salt aqueous solution was obtained. Table 4 shows these treatment conditions and evaluation results of the odor.

Comparative Example 2 The crude reaction solution of N-dodecylglycolic acid amide obtained in Example 1 was further aged for 5 hours corresponding to the blowing time in Example 1, with the system pressure set at 50 mmHg without blowing steam. Then, the odor of the obtained N-dodecylglycolic acid amide was evaluated. Further, Example 1
A 30% aqueous solution of N-dodecyl-1-sulfoxyacetamide sodium salt was obtained in the same manner as described above. Table 4 shows these treatment conditions and evaluation results of the odor.

[0051]

[Table 4]

As is clear from the results in Tables 3 and 4, the N-alkylamide alkanol obtained by the production method of the present invention and the N-alkylamide alkanol sulfate salt derived therefrom (Examples) 1 to
7) has a much better smell and is superior to that obtained by the production method without the step of blowing steam (Comparative Examples 1 and 2).

Comparative Example 3 The crude reaction solution of N-dodecylglycolic acid amide obtained in Example 1 was sulfated with chlorosulfonic acid in the same manner as in Example 1 without blowing steam, and sodium hydroxide was added. It was separated from the N-hexane phase using an aqueous solution, water and ethanol. Then, while trying to distill a part of the water and the solvent under reduced pressure while blowing steam, the foaming was so severe that it was difficult to continue the operation. That is, when steam is blown in after the sulfation, bubbling is severe and operation becomes difficult, and the merit of the present invention cannot be obtained.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 305/10 C07C 305/10 // C11D 1/28 C11D 1/28

Claims (7)

[Claims] 1. A compound represented by the following general formula (I): [In the formula, R ¹ represents a straight-chain or branched-chain alkyl group, alkenyl group, hydroxyalkyl group having 6 to 22 carbon atoms, or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group, and R ² represents a hydrogen atom. Or a linear or branched alkyl group, alkenyl group, hydroxyalkyl group having 1 to 22 carbon atoms, or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group. And an amine represented by the general formula (II): [Wherein, R ³ represents a linear or branched alkylene group having 1 to 5 carbon atoms. Or a lactone represented by the general formula (III): [Wherein, R ³ has the same meaning as described above, and R ⁴ represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. With an ω-hydroxycarboxylic acid or an ester thereof represented by the general formula (IV): [Wherein, R ¹ , R ² and R ³ have the same meaning as described above. A method for producing an N-alkylamidoalkanol represented by the formula: wherein steam or an inert gas is blown during or after the amidation reaction. 2. The following general formula (I): [In the formula, R ¹ represents a straight-chain or branched-chain alkyl group, alkenyl group, hydroxyalkyl group having 6 to 22 carbon atoms, or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group, and R ² represents a hydrogen atom. Or a linear or branched alkyl group, alkenyl group, hydroxyalkyl group having 1 to 22 carbon atoms, or an alkylphenyl group having 8 to 22 carbon atoms in the alkyl group. And an amine represented by the general formula (II): [Wherein, R ³ represents a linear or branched alkylene group having 1 to 5 carbon atoms. Or a lactone represented by the general formula (III): [Wherein, R ³ has the same meaning as described above, and R ⁴ represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. With an amidation reaction to give a compound of the general formula (IV) [Wherein, R ¹ , R ² and R ³ have the same meaning as described above. An alkylene oxide is added to the N-alkylamide alkanol represented by the general formula (V): [Wherein, R ¹ , R ² , and R ³ have the same meanings as described above, R ⁵ represents a linear or branched alkylene group having 2 to 3 carbon atoms, and n R ⁵ are the same or different. You may. n represents the average number of moles of alkylene oxide added 0 <n ≦ 50
Is any number of. To obtain an alkylene oxide adduct of an N-alkylamide alkanol represented by the following formula: during or after the amidation reaction;
A method for producing an alkylene oxide adduct of N-alkylamide alkanol, which comprises blowing steam or an inert gas into the alkylene oxide adduct of alkylamide alkanol. 3. The sulfated N-alkylamide alkanol obtained in claim 1 or the alkylene oxide adduct of N-alkylamide alkanol obtained in claim 2 is sulfated with a sulfating agent, or after sulfation. Neutralization is performed using a basic substance, and the following general formula (VI) is used. [Wherein, R ¹ , R ² , R ³ and R ⁵ have the same meanings as described above;
n number of R ⁵ may be the same or different. n is an arbitrary number from 0 to 50 indicating the average number of moles of alkylene oxide added, and M represents a hydrogen atom or a cation. A method for producing an N-alkylamide alkanol sulfate or a salt thereof, characterized by obtaining an N-alkylamide alkanol sulfate or a salt thereof represented by the following formula: 4. The blowing is performed using steam, and the ratio of the amount of steam blown to the amidated compound is 0.01 to 10 by weight of steam / reactant.
The method according to claim 1. 5. The method according to claim 1, wherein the blowing is performed in a vacuum of 200 mmHg or less.
Manufacturing method. 6. R ¹ is a linear alkyl group having 8 to 18 carbon atoms,
6. The method according to claim 1, wherein R ² is a hydrogen atom, R ³ is a methylene group, and n is 0. 7. R ¹ is a linear alkyl group having 8 to 18 carbon atoms,
^{3. The} method according to claim ² , wherein R ² is a hydrogen atom and R ³ is a methylene group.