JPH08253446A - Process for producing light-colored amino group-containing fatty acid derivative, and process for producing amide amino acid or betaine - Google Patents

Abstract

(57) [Summary] [Object] To provide a sufficiently lightened amino group-containing fatty acid derivative having a good hue and a method for producing an amide amino acid or betaine. [Structure] A fatty acid or its ester is reacted with a polyamine to produce an amino group-containing fatty acid derivative, and further, if necessary, when it is reacted with a monohaloalkylcarboxylic acid or its salt to produce an amide amino acid or betaine,
The reaction is carried out in the presence of an inorganic reducing agent selected from a specific borohydride or hydride and a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal or a hydroxide of the metal.

Description

Detailed Description of the Invention

[0001]

The present invention relates to an imidazoline compound,
A method for producing an amino group-containing fatty acid derivative such as amidoamine,
It also relates to a method for producing an amide amino acid or betaine using this amino group-containing fatty acid derivative. More specifically, a fatty acid or an ester thereof is reacted with a polyamine to produce an amino group-containing fatty acid derivative, and if necessary, the amino group-containing fatty acid derivative is reacted with a monohaloalkylcarboxylic acid or a salt thereof to give an amide amino acid or betaine. In the production, a specific inorganic reducing agent is reacted with a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal or a hydroxide of the metal to give an amino acid having a good hue. The present invention relates to a method for producing a group-containing fatty acid derivative, an amide amino acid or betaine.

[0002]

BACKGROUND OF THE INVENTION Amino group-containing fatty acid derivatives, for example, compounds having an imidazoline ring structure and substituted at the 1-position with an alkylol group (hereinafter referred to as imidazoline compound) are imidazoline-type surfactants. It is known as a useful intermediate of an agent (also called an amide amino acid type surfactant), and amidoamine is known as a useful intermediate of a betaine type surfactant. In fact, some of the commercially available shampoos use these surfactants. Particularly in recent years, surfactants used for cleaning agents and the like are biodegradable, in addition to the surfactant ability.
There is a demand for products having excellent properties such as safety and low irritation to the skin. As surfactants satisfying these requirements, there are imidazoline type surfactants and betaine type surfactants.

[0003] Imidazoline type surfactants and betaine type surfactants have excellent foaming power and detergency as well as extremely low irritation to eyes and skin, and in recent years, they have been used as a main ingredient of hypoallergenic shampoos. Usage is increasing.
As described above, amino group-containing fatty acid derivatives such as imidazoline compounds and amidoamine are not only useful as intermediates for various imidazoline-type surfactants and betaine-type surfactants, but also themselves are often used as surfactants. There is.

Hue is one of the qualities required for such imidazoline compounds, amino group-containing fatty acid derivatives such as amidoamine, imidazoline type surfactants and betaine type surfactants. Amino group-containing fatty acid derivatives such as imidazoline compounds and amidoamine can be produced by dehydration condensation of fatty acid or its ester and polyamine. Generally, this condensation reaction proceeds by reacting a higher fatty acid or its ester with a polyamine at a reaction temperature of 80 to 200 ° C. under normal pressure or reduced pressure. In such a reaction, a slight amount of impurities generally present in the raw material is converted into a coloring substance thermally or in the presence of a small amount of air to cause remarkable coloring, which greatly affects the color tone of the product or the color tone of the final product. affect.

[0005] As a manufacturing patent relating to the light-colored amino group-containing fatty acid derivative, there is, for example, US Pat. No. 3,468,904, in which sodium borohydride (N
Although the use of borohydrides of alkali metals such as aBH ₄ ) is disclosed, the lightening is still insufficient and its improvement is desired. This is because, in such a reaction method, it is extremely difficult to completely shut off air into the reaction system, that is, to maintain perfect airtightness through the reaction. It is even more difficult in reactions on an industrial scale,
No fully lightened product is obtained.

Therefore, an object of the present invention is to react a fatty acid or its ester with a polyamine to produce an amino group-containing fatty acid derivative which is sufficiently light-colored and has a good hue, and the amino group-containing fatty acid derivative. Another object of the present invention is to provide a method for producing an amide amino acid or betaine having a good hue by using.

[0007]

Means for Solving the Problems The present inventors have improved the above problems and efficiently produced a high-quality amino group-containing fatty acid derivative having a good hue, amide amino acid and betaine by a simple operation. As a result of diligent examination of the method, when reacting a fatty acid or its ester with a polyamine, a specific inorganic reducing agent and a metal of Group VIII of the periodic table, an oxide of the metal,
By carrying out the reaction in the presence of a salt of the metal or a hydroxide of the metal, an amino group-containing fatty acid derivative having an extremely good hue can be produced, and the amino group-containing fatty acid derivative is further converted into a monohaloalkylcarboxylic acid or a salt thereof. It was found that an amide amino acid or betaine having an extremely good hue can be produced by reacting with. Without any literature suggesting such a fact, the present inventors, upon reaching this fact, can efficiently produce a high-quality amino group-containing fatty acid derivative, amide amino acid and betaine by a simple operation. It became possible to complete the present invention.

That is, according to the present invention, when a fatty acid or its ester is reacted with a polyamine to produce an amino group-containing fatty acid derivative, a compound represented by the general formula (1) M ¹ (BH ₄ ) _m (1) (wherein M ¹ represents an alkali metal, an alkaline earth metal, aluminum, a quaternary ammonium or an amine, and m is a number of 1 to 4 which represents the valence of M ^1. ) or a borohydride represented by the general formula ( 2) M ² H _n (2) (in the formula, M ² represents an alkali metal, an alkaline earth metal, titanium or zirconium, and n is a number of 1 to 4 representing the valence of M ² ). An inorganic reducing agent selected from hydrides, a metal of Group VIII of the periodic table, an oxide of the metal,
The present invention provides a method for producing a light-colored amino group-containing fatty acid derivative, which comprises reacting in the presence of a salt of the metal or a hydroxide of the metal. In addition, the present invention provides the amino group-containing fatty acid derivative obtained by the above-mentioned method with the general formula
(8) YR ⁵ COOZ (8) (in the formula, Y represents a halogen atom, R ⁵ represents a linear or branched alkylene group having 1 to 4 carbon atoms, and Z represents H 2 or an alkali metal). The present invention provides a method for producing an amide amino acid or betaine, which comprises reacting with the represented monohaloalkylcarboxylic acid or a salt thereof.

The present invention will be described in detail below. The fatty acid or its ester used in the present invention has a general formula
(3) R ¹ COOR ² (3) (In the formula, R ¹ represents a linear or branched alkyl group having 7 to 23 carbon atoms, an alkenyl group or a hydroxyalkyl group, and R ²
Represents a residue obtained by removing one acyloxy group from H 2 or an alkyl group having 1 to 3 carbon atoms or glyceride. ) And higher fatty acids or esters thereof. Specifically, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, behenic acid, erucic acid, 12-hydroxystearic acid, coconut oil fatty acid, cottonseed oil fatty acid, corn oil fatty acid, Vegetable oil or animal oil fatty acid such as beef tallow fatty acid, babassu oil fatty acid, palm kernel oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, castor oil fatty acid, olive oil fatty acid, whale oil fatty acid or their methyl ester, ethyl ester, glyceride, or a mixture thereof. Is exemplified. Among these, R ²
Is preferably a higher fatty acid or a lower alkyl ester thereof, which is H or an alkyl group having 1 to 3 carbon atoms, and particularly preferable one is R ¹ is a linear alkyl group having 9 to 17 carbon atoms, R ²
Is H or CH ₃ .

Examples of the polyamine used in the present invention include alkylene polyamine, hydroxyalkyl polyamine, N-hydroxy lower alkyl alkanol amine and the like. As the alkylene polyamine, ethylenediamine, diethylenetriamine, triethylenetetramine, dimethylaminopropylamine, dimethylaminoethylamine, diethylaminopropylamine,
Diethylaminoethylamine and the like, and examples of the hydroxyalkyl polyamine include aminoethylethanolamine, aminoethylpropanolamine, aminoethylbutanolamine, N-β-hydroxypropylpropylenediamine, hydroxyethyldiethylenetriamine, hydroxyethyltriethylenetetramine and the like. Examples of the N-hydroxy lower alkyl alkanolamine include N-β-hydroxyethylethanolamine and the like.

Of these, diamines represented by the general formula (4) or (5) are preferable. _{H 2 NC 2 H 4 NHX (} 4) ( wherein, X represents an alkylol group having 2 to 4 carbon atoms.)

[0012]

[Chemical 6]

(In the formula, R ³ and R ⁴ are the same or different and each represents an alkyl group having 1 to 3 carbon atoms, and a represents a number of 2 to ^3. ) A diamine represented by the general formula (4) Particularly preferred is aminoethylethanolamine (H ₂ NC ₂ H ₄ NHC ₂ H ₄ OH), and dimethylaminopropylamine is particularly preferred as the diamine represented by the general formula (5).

In the present invention, as the amino group-containing fatty acid derivative, an imidazoline compound obtained by reacting a fatty acid or its ester with a hydroxyalkylpolyamine or a hydroxyalkylalkylenepolyamine,
Examples thereof include an oxazoline compound obtained by reacting a fatty acid or its ester with an N-β-hydroxy lower alkylalkanolamine, and an amidoamine obtained by reacting a fatty acid or its ester with a dialkylaminoalkyleneamine. Preferred is the general formula (6)

[0015]

[Chemical 7]

(In the formula, R ¹ and X have the above-mentioned meanings.)
An imidazoline compound represented by or a general formula (7)

[0017]

Embedded image

(In the formula, R ¹ , R ³ , R ⁴ and a have the above-mentioned meanings) and are amidoamines.

Among the inorganic reducing agents used in the present invention, the borohydride represented by the general formula (1) is NaB
_{H 4, LiBH 4, KBH 4} , Ca (BH 4) 2, Ba (BH 4) 2, Mg (BH 4) 2, Sr
(BH ₄ ) ₂ , LiAl (BH ₄ ) ₄ , tetramethylammonium borohydride, tetraethylammonium borohydride, tetrapropylammonium borohydride,
Tetraisopropylammonium borohydride, triethylamine borohydride, triisopropylamine borohydride, tributylamine borohydride, triisobutylamine borohydride and the like, and also, as the hydride represented by the general formula (2), NaH, KH, Examples thereof include LiH, CaH ₂ , TiH ₄ , ZrH ₄ . As these inorganic reducing agents, borohydride represented by the general formula (1) is preferable, and particularly in the general formula (1)
M ¹ is an alkali metal or alkaline earth metal and m is 1
Alternatively, borohydride of 2 is preferable, NaBH ₄ and LiBH ₄ are more preferable, and NaBH ₄ is particularly preferable.

Further, the periodic table No. VIII used in the present invention
Examples of the metal of the group, the oxide of the metal, the salt of the metal or the hydroxide of the metal include metals such as Fe, Co and Ni, oxides of the metal and salts of the metal, and specifically, Is a metal such as Fe, Co, Ni, a metal oxide such as FeO, CoO, NiO, Fe ₂ O ₃ , Fe, C
o, NH metals such as Ni _{4, Cl, Br, SO 4} , PO 4, CO 3, NO 3
Examples thereof include salts and hydroxides of metals such as Fe, Co and Ni. Preferred are Fe, FeO 2, CoO 2, NiO 2, FeCl _{3 and the} like. In the present invention, it is particularly preferable to react with NaBH ₄ or LiBH _{4 in} the presence of iron, iron oxide, iron salt or iron hydroxide.

In the production method of the present invention, in order to obtain a high-quality amino group-containing fatty acid derivative, the addition timing of the inorganic reducing agent is such that the inorganic reducing agent is easily decomposed under acidic conditions. It is preferable to add a polyamine, a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal, or a hydroxide of the metal to a reaction vessel, and then add an inorganic reducing agent. When the inorganic reducing agent is dissolved in the polyamine in advance, the order of charging does not matter.

In the present invention, the temperature, time and the like for treating with the inorganic reducing agent, the metal of Group VIII of the periodic table, the oxide of the metal, the salt of the metal or the hydroxide of the metal are not particularly limited. For example, when the imidazoline compound or the oxazoline compound as described above is produced, the reaction temperature is 0 to
The temperature is 120 ° C., preferably 30 to 110 ° C., the treatment time is 1 minute to 5 hours, preferably 10 to 60 minutes, and the pressure during the treatment is preferably atmospheric pressure. After treatment with an inorganic reducing agent and a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal or a hydroxide of the metal, the reaction temperature is 180 to 220 ° C, and the reaction pressure is 760 ~ 1 mmH
It is desirable to perform amidation, imidazolinization, etc. in the range of g, preferably in the range of 400 to 5 mmHg. When producing amidoamine as described above, the reaction temperature for amidation is 80 to 220 ° C, preferably 90 to 200 ° C.
The reaction time is 1 to 10 hours, preferably 2 to 6 hours. Further, when a fatty acid ester is used, it is preferable to react it in the presence of a catalyst such as sodium methylate, if necessary.

In the method of the present invention, the molar ratio of fatty acid or its ester to polyamine is usually fatty acid or its ester: polyamine = 1: 1 to 1: 2, preferably 1: 1 to 1: 1.5. Further, the addition amount of the inorganic reducing agent used in the present invention is based on the fatty acid or its ester.
It is preferably 0.001 to 5% by weight, more preferably 0.01 to 0.3% by weight. Further, the addition amount of a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal or a hydroxide of the metal is preferably 0.0001 to 0.01% by weight with respect to the fatty acid or ester thereof, and 0.0005 to More preferably 0.005% by weight.

Further, in the present invention, the amino group-containing fatty acid derivative obtained as described above is prepared by the above general formula (8)
The amide amino acid or betaine having a remarkably good hue can be obtained by reacting with a monohaloalkylcarboxylic acid represented by or a salt thereof. For example, by reacting an imidazoline compound represented by the general formula (6) with a monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof, the general formula (9)

[0025]

[Chemical 9]

An amide amino acid represented by the formula (wherein R ¹ , R ⁵ , X and Z have the above-mentioned meanings) can be obtained, and the amidoamine represented by the general formula (7) can be represented by the general formula
(8) represented by the general formula (10) by reacting with a monohaloalkylcarboxylic acid or salt thereof

[0027]

[Chemical 10]

A betaine represented by the formula (wherein R ¹ , R ³ , R ⁴ , R ⁵ and a have the above-mentioned meanings) can be obtained.
In the present invention, the reaction between the amino group-containing fatty acid derivative and the monohaloalkylcarboxylic acid or a salt thereof can be carried out by a conventionally known method. For example, when the amino group-containing fatty acid derivative is an imidazoline compound, the imidazoline is subjected to ring opening with an alkaline aqueous solution, and then a monohaloalkylcarboxylic acid or a salt thereof is reacted. The reaction is preferably maintained in the pH range of 8 to 11, and the reaction temperature is preferably in the range of 50 to 90 ° C. The reaction may be carried out at normal pressure or under pressure. Further, when the amino group-containing fatty acid derivative is the above-mentioned amidoamine, the pH of the amidoamine and the monohaloalkylcarboxylic acid or salt thereof is kept at 8 to 10 until the betaine formation is completed, and then the remaining monohaloalkylcarboxylic acid salt. In order to promote the hydrolysis of the above, it is preferable to carry out the reaction while maintaining the pH in the range of 11.5 to 13, and the reaction temperature is preferably in the range of 50 to 100 ° C. The reaction may be carried out at normal pressure or under pressure.

As the monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof used herein, monochloroacetic acid, monobromoacetic acid, monochloropropionic acid,
Examples thereof include monobromopropionic acid or a sodium salt or potassium salt thereof, and monochloroacetic acid or a salt thereof is particularly preferable. The amount of the monohaloalkylcarboxylic acid or its salt with respect to the amino group-containing fatty acid derivative is preferably 1 to 3 times by mole, and more preferably 1 to 1.15 times by mole.

In the present invention, when the amino group-containing fatty acid derivative is reacted with the monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof, the above general formula (1)
It is preferable to allow the presence of an inorganic reducing agent selected from borohydride represented by or hydride represented by the general formula (2). Thus, the presence of the inorganic reducing agent makes it possible to obtain an amide amino acid or betaine having a better hue.

By the method of the present invention as described above, an amino group-containing fatty acid derivative, an amide amino acid and betaine having a remarkably good hue can be obtained. Although there are many unclear parts about the details of this reason, in particular, a trace amount of a coloring component contained in a fatty acid or its ester, for example, a coloring precursor derived from tocopherols is converted into a non-coloring substance by the above-mentioned specific inorganic reducing agent. The presence of a trace amount of a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal, or a hydroxide of the metal is associated with an oxidation reaction that occurs when oxygen is present in the reaction system, that is, coloration. Therefore, it is presumed that it has an antioxidant effect and prevents conversion into a coloring substance. Thus, the present invention is useful as a method for producing an amino group-containing fatty acid derivative having a good hue, and an amide amino acid or betaine.

[0032]

EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited thereto.

Example 1 200 g of lauric acid (molecular weight) was placed in a 1-liter 5-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a pressure gauge.
(200, 1 mol) was charged, and nitrogen gas was blown at 100 cc / hr from the capillary tube. Then, 109.2 g of aminoethylethanolamine (molecular weight 104, 1.05 mol, hereinafter AE
(Abbreviated as EA) and 0.0015 g of iron oxide (FeO) were added. Heating temperature is cooled after increased to 100 ° C. by, 60 ° C. when it becomes Zodiac um borohydride (NaBH ₄₎ was added 0.18 g (molecular weight 38), was held for 30 minutes, the reaction pressure 400m
The temperature was set to mHg, and the temperature was raised to 200 ° C over 1 hour. When the reaction temperature reaches 200 ° C, the pressure is reduced to 200 mmHg, the pressure is maintained for 2 hours, the pressure is further reached to 5 mmHg in 3 hours to complete the reaction, and the reaction is cooled to 50 ° C. The mixture was discharged. The imidazoline ring content of this reaction mixture was 94% from the measured amine value.
Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 2 Total amount of the reaction mixture obtained in Example 1, 54 ion-exchanged water
g and 1.2 g of sodium hydroxide were placed in a 2-liter 4-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, heated to 80 ° C with stirring, and stirred at that temperature for about 2 hours. Subsequently, the imidazoline ring was opened.
Next, separately prepared sodium monochloroacetate (MW116.
5) A solution of 128.2 g and 787 g of water was charged into this container.
Next, 110 g of 40% sodium hydroxide aqueous solution was added dropwise over 4 hours while maintaining the temperature of the solution at 70 to 80 ° C. After the dropping, further aging at a temperature of 75 ~ 80 ℃, then cooled,
1220 g of an aqueous solution containing 30% of {N-lauroyl-N '-(2-hydroxyethyl) -N'-sodium carboxymethyl} ethylenediamine was obtained. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA60.

Example 3 Using the same reactor as in Example 1, 220.5 g of coconut oil fatty acid methyl ester (molecular weight 220.
The reaction was carried out under the same reaction conditions as in Example 1 except that 1 mol) was used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 4 The reaction mixture obtained in Example 3 was reacted with sodium monochloroacetate as in Example 2 to give 30% of {N-cocoyl-N '-(2-hydroxyethyl) -N'. An aqueous solution containing sodium carboxymethyl} ethylenediamine was obtained. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA50.

Example 5 The same reaction conditions as in Example 1 were carried out except that the same flow rate of air was blown in place of the nitrogen gas of Example 1. The imidazoline ring content of the reaction mixture was determined to be 94 from the amine value measurements.
%Met. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 6 The reaction was carried out under the same conditions as in Example 1 except that metal powder iron (Fe) was used instead of iron oxide (FeO). The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 7 The reaction was carried out under the same conditions as in Example 1 except that nickel oxide (NiO) was used instead of iron oxide (FeO). The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 8 The reaction was carried out under the same conditions as in Example 1 except that cobalt oxide (CoO) was used instead of iron oxide (FeO). The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1.

Example 9 Ferric chloride (FeCl ₃ .6H ₂ O) was used instead of iron oxide (FeO).
The reaction conditions were the same as in Example 1 except that 0.005 g was used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 1-2.

Comparative Example 1 The same reaction conditions as in Example 1 were used except that iron oxide (FeO) was not used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 3.

Comparative Example 2 The reaction mixture obtained in Comparative Example 1 was reacted with sodium monochloroacetate as in Example 2 to give 30% of {N-lauroyl-N '-(2-hydroxyethyl) -N'. An aqueous solution containing sodium carboxymethyl} ethylenediamine was obtained. As a result of measuring the hue of this product with a colorimetric tube,
The hue was APHA200.

Comparative Example 3 The reaction conditions were the same as in Example 1 except that NaBH ₄ and iron oxide (FeO) were not used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 5.

Comparative Example 4 The reaction conditions were the same as in Example 1 except that NaBH ₄ was not used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 3.

Comparative Example 5 The same reaction conditions as in Example 5 were used except that NaBH ₄ and iron oxide (FeO) were not used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 7.

Comparative Example 6 The same reaction conditions as in Example 5 were used except that NaBH ₄ was not used. The imidazoline ring content of the reaction mixture was 94% from the measured amine value. Further, as a result of measuring the hue with a colorimetric tube, the hue was Gardner 7.

Example 10 200 g of lauric acid (molecular weight 2 was added to a 1-liter 5-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a pressure gauge.
(1 mole) and 0.0015 g of iron oxide (FeO) were charged, and nitrogen gas was blown through the capillary tube at 100 cc / Hr. 1
The temperature was raised to 80 ° C. Then, 0.18 g (molecular weight 38) of sodium borohydride (NaBH ₄ ) was previously added to 102 g (molecular weight 102, 1 mol) of dimethylaminopropylamine and dissolved therein, followed by dropwise addition over 3 hours. Then, hold under this condition for 2 hours, measure the acid value (AV) and confirm that it is 10 or less, then stop blowing nitrogen gas and set the system pressure to 50 To by a vacuum pump connected in advance.
After decreasing to rr and removing the residual dimethylaminopropylamine, the mixture was cooled to 50 ° C. As a result of measuring the hue of this reaction mixture with a colorimetric tube, the hue was Gardner 1.

Example 11 Total amount of the reaction mixture obtained in Example 10 and ion-exchanged water 7
98g 2 equipped with stirrer, thermometer, dropping funnel, cooling tube
After charging in a 4-liter 4-necked flask, the reaction temperature was adjusted.
The temperature was raised to 80 ° C. When the temperature reached, 116.5 g of a powdery product of sodium monochloroacetate (MW116.5) was charged, and after aging for 1 hour, 40% NaOH was added dropwise to adjust the system pH to 12. Then, the mixture was aged for 8 hours and then cooled. The product was 1140 g of an aqueous solution containing 30% lauroylaminopropyldimethylglycine betaine. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA50.

Example 12 Total amount of the reaction mixture obtained in Example 10 and ion-exchanged water 7
98g 2 equipped with stirrer, thermometer, dropping funnel, cooling tube
After charging in a 4-liter 4-necked flask, the reaction temperature was adjusted.
The temperature was raised to 80 ° C. When the temperature reached, 116.5 g of a powdery product of sodium monochloroacetate (MW116.5) was charged, and after aging for 1 hour, 40% NaOH was added dropwise to adjust the system pH to 12. Then, 0.68 g of NaBH ₄ was charged, the mixture was aged for 8 hours, and then cooled. The product was 1140 g of an aqueous solution containing 30% lauroylaminopropyldimethylglycine betaine. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA20.

Example 13 Using the same reactor as in Example 10, 220.5 g of coconut oil fatty acid methyl ester (molecular weight 220.
(5, 1 mol) was carried out under the same reaction conditions as in Example 10 except that it was used. As a result of measuring the hue of the reaction mixture with a colorimetric tube,
The hue was Gardner 1.

Example 14 The reaction mixture obtained in Example 13 was reacted with a powdered product of sodium monochloroacetate in the same manner as in Example 12 to obtain an aqueous solution containing 30% of cocoylaminopropyldimethylglycine betaine. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA20.

Example 15 The same reaction conditions as in Example 10 were carried out except that the same flow rate of air was blown in place of the nitrogen gas of Example 10. As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 1.

Example 16 A reaction was carried out under the same conditions as in Example 10 except that metal powder iron (Fe) was used instead of iron oxide (FeO). As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue is Gardner 1
Met.

Example 17 The reaction was carried out under the same conditions as in Example 10 except that nickel oxide (NiO) was used instead of iron oxide (FeO). As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 1.

Comparative Example 7 The reaction was carried out under the same conditions as in Example 10 except that NaBH ₄ and iron oxide (FeO) were not used. As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 4.

Comparative Example 8 The reaction mixture obtained in Comparative Example 7 was reacted with a powdered product of sodium monochloroacetate in the same manner as in Example 11 to obtain an aqueous solution containing 30% lauroylaminopropyldimethylglycine betaine. As a result of measuring the hue of this product with a colorimetric tube, the hue was APHA200.

Comparative Example 9 The reaction was carried out under the same conditions as in Example 10 except that iron oxide (FeO) was not used. As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 3.

Comparative Example 10 The reaction was carried out under the same conditions as in Example 15 except that NaBH ₄ and iron oxide (FeO) were not used. As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 7.

Comparative Example 11 The reaction was carried out under the same conditions as in Example 16 except that the metal powder iron (Fe) was not used. As a result of measuring the hue of the reaction mixture with a colorimetric tube, the hue was Gardner 3.

Claims (18)

[Claims] 1. When a fatty acid or its ester is reacted with a polyamine to produce an amino group-containing fatty acid derivative, the compound represented by the general formula (1) M ¹ (BH ₄ ) _m (1) (wherein M ¹ is an alkali A metal, an alkaline earth metal, aluminum, a quaternary ammonium or an amine, and m is a number of 1 to 4 showing a valence of M ^1. ), or a borohydride represented by the general formula (2) M ² From a hydride represented by H _n (2) (in the formula, M ² represents an alkali metal, an alkaline earth metal, titanium or zirconium, and n is a number of 1 to 4 representing the valence of M ² ). An inorganic reducing agent selected, a metal of Group VIII of the periodic table, an oxide of the metal,
A method for producing a light-colored amino group-containing fatty acid derivative, which comprises reacting in the presence of a salt of the metal or a hydroxide of the metal. 2. A fatty acid or ester thereof is represented by the general formula (3) R ¹ COOR ² (3) (wherein R ¹ is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 7 to 23 carbon atoms). Indicates R ²
Represents a residue obtained by removing one acyloxy group from H 2 or an alkyl group having 1 to 3 carbon atoms or glyceride. The method according to claim 1, which is a higher fatty acid or ester thereof represented by 3. The method according to claim ² , wherein R ² is H or an alkyl group having 1 to 3 carbon atoms. 4. The polyamine is an alkylene polyamine,
The method according to any one of claims 1 to 3, which is a hydroxyalkyl polyamine or an N-hydroxy lower alkyl alkanolamine. 5. The polyamine is a diamine represented by the general formula (4) H ₂ NC ₂ H ₄ NHX (4) (wherein, X represents an alkylol group having 2 to 4 carbon atoms). Item 4. The production method according to Item 4. 6. The polyamine has the general formula (5): (Wherein R ³ and R ⁴ are the same or different and each represents an alkyl group having 1 to 3 carbon atoms, and a represents a number of 2 to 3), which is a diamine. Law. 7. The amino group-containing fatty acid derivative is an imidazoline compound or an oxazoline compound.
The method according to any one of 1. 8. The amino group-containing fatty acid derivative has the general formula
(6) [Chemical 2] The process according to claim 7, which is an imidazoline compound represented by the formula (wherein R ¹ and X have the above meanings). 9. The amino group-containing fatty acid derivative has the general formula
(7) [Chemical 3] The production method according to claim 1, wherein the amidoamine is represented by the formula (wherein R ¹ , R ³ , R ⁴ and a have the above-mentioned meanings). 10. The method according to claim 1, wherein the inorganic reducing agent is a borohydride represented by the general formula (1). 11. The method according to claim 10, wherein M ¹ in the general formula (1) is an alkali metal or an alkaline earth metal, and m 1 is 1 or 2. 12. The inorganic reducing agent is NaBH ₄ or LiBH ₄ , and the metal of Group VIII of the periodic table, the oxide of the metal, the salt of the metal or the hydroxide of the metal is iron or iron oxide. , Iron salt or iron hydroxide, The manufacturing method as described in any one of Claims 1-11. 13. An inorganic reducing agent is added to a fatty acid or its ester in an amount of 0.001 to 5% by weight, and a metal of Group VIII of the periodic table, an oxide of the metal, a salt of the metal or a hydroxide of the metal is added. 0.0001-0.01 weight% is added with respect to a fatty acid or its ester, The manufacturing method as described in any one of Claims 1-12. 14. The amino group-containing fatty acid derivative obtained by the production method according to claim 1, which is represented by the general formula (8) YR ⁵ COOZ (8) (wherein Y is a halogen atom). R ⁵ represents a linear or branched alkylene group having 1 to 4 carbon atoms, Z represents H or an alkali metal), and a monohaloalkylcarboxylic acid or salt thereof represented by A method for producing an amide amino acid or betaine. 15. An amide amino acid represented by the general formula (9) is obtained by reacting the imidazoline compound represented by the general formula (6) with a monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof. The method according to claim 14, which is obtained. [Chemical 4] (In the formula, R ¹ , R ⁵ , X and Z have the above meanings.) 16. A betaine represented by the general formula (10) is obtained by reacting an amidoamine represented by the general formula (7) with a monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof. 15. The manufacturing method according to claim 14, wherein: Embedded image (In the formula, R ¹ , R ³ , R ⁴ , R ⁵ and a have the above meanings.) 17. Amino group-containing fatty acid derivative and general formula
The reaction with a monohaloalkylcarboxylic acid represented by (8) or a salt thereof, a borohydride represented by the general formula (1),
Alternatively, the production method according to any one of claims 14 to 16, which is carried out in the presence of an inorganic reducing agent selected from the hydride represented by the general formula (2). 18. The method according to claim 14, wherein the monohaloalkylcarboxylic acid represented by the general formula (8) or a salt thereof is monochloroacetic acid or a salt thereof.