JP2003171355A - Method for producing aminocarboxylic acid amide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for producing an aminocarboxylic acid amide in high selectivity and high economical efficiency. <P>SOLUTION: This method for producing the aminocarboxylic acid amide represented by formula (III) comprises reacting a primary amine represented by the formula R<SP>1</SP>-NH<SB>2</SB>(I) with an aminocarboxylic acid represented by formula (II) to carry out amidation [in these formulas, R<SP>1</SP>is an 8-40C alkyl group, a group, represented by the formula R<SP>5</SP>O-(AO)<SB>n</SB>-C<SB>m</SB>H<SB>2m</SB>(R<SP>5</SP>is an 8-40C alkyl group, or the like; A is a 2-3C alkylene group; (n) is 0-30; (m) is an integer of 2-3), or the like; R<SP>2</SP>is a 1-5C alkylene group; R<SP>3</SP>is H, a 1-24C alkyl group, or the like; R<SP>4</SP>is H, a 1-5C alkyl group, or the like; (p) is an integer of 1-3; (q) and (r) are each an integer of 0-2 and (p+q+r) is 3]. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention shows excellent softness to fibers, imparts excellent softness and smoothness to hair, and further exhibits biodegradability, fish toxicity, algae toxicity and the like. The present invention relates to a highly selective method for producing an aminocarboxylic acid amide useful as a surfactant having good environmental safety or an intermediate thereof.

[0002]

PRIOR ART AND PROBLEM TO BE SOLVED BY THE INVENTION As an example of synthesizing an aminocarboxylic acid amide, there is disclosed in JP-A-55-14.
3944 and WO98 / 03472 describe a method of reacting an aminocarboxylic acid ester with an amine, a method of reacting an amine with a halocarboxylic acid amide, and the like. However, the method using an aminocarboxylic acid ester or a halocarboxylic acid amide has a problem that a large amount of reaction solvent is required when synthesizing these raw materials and the aminocarboxylic acid amide, and the selectivity of the reaction is low. Was difficult to manufacture.

The object of the present invention is to show excellent flexibility to fibers, to impart excellent flexibility and smoothness to hair, and further to be environmentally safe such as biodegradability, fish toxicity and algae toxicity. It is an object of the present invention to provide a highly economical production method of a surfactant having good properties or an aminocarboxylic acid amide useful as an intermediate thereof, with high selectivity and high yield without complicated purification operation.

[0004]

The present invention provides a compound represented by the general formula (I) R ¹ —NH ₂ (I) [wherein R ¹ is a linear or branched alkyl or alkenyl group having 8 to 40 carbon atoms]. Or the formula R ⁵ O- (AO) _n
—C _m H _2m — (R ⁵ is a linear or branched alkyl or alkenyl group having 8 to 40 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, n is an average value of 0 to 30, m is 2-3
And n of A may be the same or different). ] A primary amine (hereinafter referred to as primary amine (I)) represented by the general formula (II)

[0005]

[Chemical 3]

[In the formula, R ² is a linear or branched alkylene group having 1 to 5 carbon atoms, R ³ is a hydrogen atom, and 1 to 1 carbon atoms.
24 linear or branched alkyl group, alkenyl group or hydroxyalkyl group, or aryl group or arylalkyl group having 6 to 28 carbon atoms, R ⁴ is a hydrogen atom, linear or branched chain having 1 to 5 carbon atoms Alkyl group, alkenyl group or hydroxyalkyl group, or 6 to 2 carbon atoms
8 represents an aryl group or an arylalkyl group, and R ³ and R ⁴ may be alone or combined to form a ring. p is 1
Is an integer from 0 to 3, q and r are integers from 0 to 2, and p + q + r is 3. Note that p R ¹ , R ² , q R ³ , and r R ⁴
May be the same or different. ] Amidation is carried out by reacting an aminocarboxylic acid (hereinafter referred to as aminocarboxylic acid (II)) represented by the following general formula (III)

[0007]

[Chemical 4]

[In the formula, R ¹ , R ² , R ³ , R ⁴ , p, q and r have the same meanings as described above. ] A method for producing an aminocarboxylic acid amide (hereinafter referred to as aminocarboxylic acid amide (III)) is provided.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the primary amine (I), R
¹ is a straight-chain or branched alkyl or alkenyl group of 10 to 28 carbon atoms, or the formula _{^{R 5 O- (AO) n -C}} m H
_{In the} group represented by 2m-, R ⁵ is preferably a linear or branched alkyl group or alkenyl group having 10 to 28 carbon atoms, and groups in which A, n and m have the same meanings as described above, and further 12 carbon atoms. 24 linear or branched alkyl or alkenyl group, or the formula _{^{R 5 O- (AO) n -C}} m H 2m - in a group represented by, R ⁵ is or a straight chain of 12-24 carbon atoms A branched chain alkyl group or alkenyl group, and groups in which A, n and m have the same meanings as described above are preferable, and particularly a carbon number of 12 to 24
Or a straight chain alkyl group of the formula R ⁵ O- (AO) _n -C _m H _2m
In the group represented by-, R ⁵ is preferably a linear alkyl group having 12 to 24 carbon atoms, and A, n and m have the same meanings as described above. Each of the above n is preferably 0 to 20 and more preferably 5 or less.

As the primary amine (I), dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine, docosylamine,
Alkyl or alkenylamines such as tetracosylamine, octadecenylamine, docosenylamine, etc., long-chain alcohols such as dodecanol, tetradecanol, hexadecanol, octadecanol, eicosanol, docosanol, tetracosanol and ethylene oxide thereof. Adducts and / or propylene oxide adducts obtained by cyanoethylation with acrylonitrile and then hydrogenated with a catalyst, or ethylene oxide adducts and / or propylene oxide adducts to the aforementioned long-chain alcohols N-alkyl polyoxyethylene amine, N-alkyl polyoxypropylene amine, etc. obtained by halogenating the terminal hydroxyl group of and then reacting with ammonia.

In the aminocarboxylic acid (II), R ² is preferably a linear or branched alkylene group having 1 to 3 carbon atoms, more preferably a linear alkylene group having 1 to 3 carbon atoms, and particularly preferably a methylene group. . R ³ has 1 to 22 carbon atoms
Is preferably a linear or branched alkyl group, alkenyl group or hydroxyalkyl group, or an aryl group or arylalkyl group having 6 to 28 carbon atoms, and having 1 to 3 carbon atoms.
Is more preferably a linear or branched alkyl group or hydroxyalkyl group, or an aryl group or arylalkyl group having 6 to 10 carbon atoms. R ⁴ is preferably a linear or branched alkyl group having 1 to 5 carbon atoms, an alkenyl group or a hydroxyalkyl group, or an aryl group or arylalkyl group having 6 to 28 carbon atoms, and a linear or branched alkyl group having 1 to 3 carbon atoms. A branched chain alkyl group or hydroxyalkyl group, a phenyl group or a benzyl group is more preferable. R ³
And when R ⁴ is bonded to form a ring, the total carbon number of R ³ and R ⁴ is preferably 4 to 28, more preferably 4 to 10,
A 5-membered ring or a 6-membered ring is particularly preferable. p is preferably an integer of 1 or 2. q and r are preferably 0 or 1, particularly the third
Primary amines are preferred.

As aminocarboxylic acid (II), N, N-
Dimethylglycine, 3- (dimethylamino) propionic acid, 4- (dimethylamino) butanoic acid, N, N-diethylglycine, 3- (diethylamino) propionic acid, 4
-(Diethylamino) butanoic acid, N- (2-hydroxyethyl) -N-methylglycine, 3- (N- (2-hydroxyethyl) -N-methylamino) propionic acid,
Examples thereof include N, N-bis (2-hydroxyethyl) glycine, methyliminodiacetic acid, ethyliminodiacetic acid, nitrilotriacetic acid, pyrrolidinylacetic acid, N-methyl-N-phenylaminoacetic acid and N-methyl-N-tolylaminoacetic acid.

The aminocarboxylic acid (II) may be produced by any method. For example, halocarboxylic acid and amine,
A method of reacting with a solvent such as water in the presence of a hydroxide of an alkali metal such as NaOH or KOH, if necessary, and specific aminocarboxylic acids include aldehyde compounds such as formalin and sodium cyanide and amines. The corresponding aminocarboxylic acid or an alkali metal salt thereof can be obtained by a Strecker reaction method using, a method of oxidizing amino alcohol using an oxidation catalyst and an oxidizing agent, and the like. Aminocarboxylic acid alkali metal salts include sulfuric acid, hydrochloric acid,
Neutralize with an acid such as phosphoric acid, distill off the solvent if necessary,
The aminocarboxylic acid is obtained by removing or reducing the precipitated inorganic salt and the like.

In the production method of the present invention, aminocarboxylic acid (I
There is almost no effect on the reactivity and selectivity in amidation of I) containing no inorganic salt and those containing inorganic salt. That is, both can be used, but expensive equipment and complicated operations are required to obtain those containing no inorganic salt in the aminocarboxylic acid (II), and amino containing an inorganic salt from the viewpoint of economic efficiency. Carboxylic acid (II) can be used as a raw material and can be removed simultaneously with the unreacted raw material after amidation. It is also possible to neutralize the alkali metal salt of aminocarboxylic acid (II) with the above acid, perform an amidation reaction as it is, and remove the inorganic salt after completion of the reaction.

In the amidation of the present invention, aminocarboxylic acid (II) is preferably added in an amount of 0.5 to 3 equivalents, more preferably 0.9 to 1.5, relative to 1 equivalent of primary amine (I).
React in equivalent amounts.

The reaction temperature for amidation is 120 to 250 ° C.
Are preferable, and 140-230 degreeC is more preferable. The reaction time is preferably 1 to 30 hours, more preferably 3 to 20 hours.

In order to suppress the deterioration of hue during amidation, aminocarboxylic acid (II) or primary amine (I) may be reduced with sodium borohydride or the like, if necessary.
During the amidation, substitution or introduction of an inert gas such as nitrogen or vapor can be performed.

Further, unreacted aminocarboxylic acid (II),
For the purpose of removing impurities such as inorganic salts, it is preferable to carry out washing with water or solid-liquid separation after amidation. In the case of washing with water, the amount of water is preferably 5 to 300% by weight, more preferably 10 to 150% by weight, based on the amidation product. The washing temperature is not lower than the melting point of the amidation product, preferably 50 to 95 ° C., and the washing frequency is preferably 1 to 3 times. Residual water can be removed by dehydration after separation and separation. For solid-liquid separation, filter press filter or Nutsche filter,
It can be performed by a known method such as a centrifuge.

Further, the resulting aminocarboxylic acid amide (I
In order to reduce the odor of II), deodorizing operations such as steaming can be performed.

[0020]

EXAMPLES In the examples,% is weight% unless otherwise specified.

Example 1 In a four-necked flask equipped with a stirrer, a thermometer, a dehydration tube, and a nitrogen introduction tube, 134.1 g of N, N-dimethylglycine and Nissanamine VBS (Alkyl 1 manufactured by NOF Corporation)
325.6 g of primary amine) was added, and water of reaction was distilled off while introducing nitrogen at a temperature of 200 ° C., and the reaction was carried out for 6 hours. Then, after cooling to 80 ° C., 102.7 g of water was added,
The mixture was stirred at 0 ° C. for 30 minutes, the layers were separated, and the aqueous layer was discarded. This water washing operation was performed twice to remove unreacted N, N-dimethylglycine and the like. After that, the temperature is 80 ° C and the degree of vacuum is 3.9 kP.
a, it was dehydrated in 1 hour. Next, 180 ° C, vacuum degree 1.3
Introduces 8.2 g of steam at kPa for 2 hours for deodorization,
Aminocarboxylic acid amide 40 which is a target light yellow solid
2.5 g was obtained. ^The following structure and composition were confirmed from ¹ H-NMR spectrum, IR spectrum, gas chromatography, atomic absorption analysis and the like.

[0022]

[Chemical 5]

¹ H-NMR spectrum (CDCl ₃ , internal standard TMS) a 3.27 ppm (q, 2H) b 7.13 ppm (1H) c 2.93 ppm (s, 2H) d 2.26 ppm (s, 6H ) ・ IR spectrum (KBr tablets) 1648 cm ^-1 , 1525 cm ^-1・ Purity 98.6% (others; primary amine 0.1%, dimethylglycine 0.1%) ・ R ⁵ CH _2- the composition _{C 18 H 37 / C 20 H} 41 / C 22 H 45 / C 24 H 49 = 4% / 12% / 82% / 2% example 2 similar four-necked flask as in example 1 alkyl group, 163.1 g of a 50% aqueous solution of N, N-dimethylglycine potassium salt was added and neutralized with 28.9 g of 98% sulfuric acid. The pH of this product was 6.1. Next, after concentrating to 70% while blowing nitrogen at 120 to 130 ° C., 147.0 g of Pharmin 80 (an alkyl primary amine manufactured by Kao Co., Ltd.) was added and reaction water was introduced at a temperature of 180 ° C. while introducing nitrogen. Distilled off, 8
Reacted for hours. Then, after cooling to 80 ° C., unreacted N, N-dimethylglycine, potassium sulfate, and the like were removed with a Nutsche type filter to obtain 173.8 g of a desired light yellow solid, an aminocarboxylic acid amide. ^The following structure and composition were confirmed from ¹ H-NMR spectrum, IR spectrum, gas chromatography, atomic absorption analysis and the like.

[0024]

[Chemical 6]

¹ H-NMR spectrum (CDCl ₃ , internal standard TMS) a 3.26 ppm (q, 2H) b 7.15 ppm (1H) c 2.93 ppm (s, 2H) d 2.27 ppm (s, 6H ) ・ IR spectrum (KBr tablet) 1649 cm ^-1 , 1525 cm ^-1・ Purity 97.2% (others; primary amine 1.1%, dimethylglycine 0.2%, potassium sulfate 0.1% or less) ・ R ⁶ Composition of alkyl group represented by CH ₂ − C ₁₆ H ₃₃ / C ₁₇ H ₃₅ / C ₁₈ H ₃₇ / C ₁₉ H ₃₉ / C ₂₀ H ₄₁ = 4% / 1% / 93.5% /
0.5% / 1% Example 3 In a four-necked flask equipped with a stirrer, a thermometer, and a cooling tube,
50% aqueous solution of N, N-dimethylglycine potassium salt 2
After adding 82.4 g and adding 98% sulfuric acid until the pH became 5.7, the mixture was cooled to 25 ° C. to remove precipitated potassium sulfate, and 41.1% N, N containing 2.7% potassium sulfate.
188.3 g of aqueous dimethylglycine solution were obtained.

Next, a 41.1% N, N-dimethylglycine aqueous solution 1 containing 2.7% of potassium sulfate obtained above was obtained.
51.8 g and Pharmin 80 (an alkyl primary amine manufactured by Kao Co., Ltd.) 147.0 g were added, and the reaction water was distilled off while introducing nitrogen at a temperature of 180 ° C., and the reaction was carried out for 8 hours. Then, after cooling to 70 ° C., 97.0 g of water was added,
By stirring for 30 minutes at 0 ° C., washing the separated layers with water to remove unreacted N, N-dimethylglycine and potassium sulfate, and further dehydrating at 80 ° C. and a vacuum degree of 3.9 kPa for 1 hour, 191.1 g of the desired pale yellow solid aminocarboxylic acid amide was obtained. ^The following structure and composition were confirmed from ¹ H-NMR spectrum, IR spectrum, gas chromatography, atomic absorption analysis and the like.

[0027]

[Chemical 7]

¹ H-NMR spectrum (CDCl ₃ , internal standard TMS) a 3.27 ppm (q, 2H) b 7.23 ppm (1H) c 2.94 ppm (s, 2H) d 2.27 ppm (s, 6H ) ・ IR spectrum (KBr tablet) 1649 cm ^-1 , 1526 cm ^-1・ Purity 97.8% (others; primary amine 0.4%, dimethylglycine 0.1%, potassium sulfate 0.1% or less) ・ R Composition of alkyl group represented by ⁷ CH ₂ − C ₁₆ H ₃₃ / C ₁₇ H ₃₅ / C ₁₈ H ₃₇ / C ₁₉ H ₃₉ / C ₂₀ H ₄₁ = 4.5% / 2.1% / 92.0
% / 0.5% / 0.9% Example 4 168.5 g of N, N-diethylglycine sodium salt and 800.0 g of water were placed in the same four-necked flask as in Example 1, and 36% aqueous hydrochloric acid solution (111.4 g) was added. I made it The pH of this product was 6.5. Next, after concentrating to 70% while blowing nitrogen at 110 ° C, Pharmin 80
267.6 g of (alkyl primary amine manufactured by Kao Co., Ltd.) was added, the reaction water was distilled off while introducing nitrogen at a temperature of 170 ° C., and the reaction was carried out for 12 hours. Then, after cooling to 80 ° C., 380 g of water was added, the mixture was stirred at 80 ° C. for 30 minutes, and the separation layer was washed twice with water to remove unreacted N, N-diethylglycine, sodium chloride and the like. Dehydration at ℃, vacuum degree of 3.9 kPa for 1 hour gives 369.3 g of aminocarboxylic acid amide which is a target light yellow solid.
Got ^The following structure and composition were confirmed from ¹ H-NMR spectrum, IR spectrum, gas chromatography, atomic absorption analysis and the like.

[0029]

[Chemical 8]

¹ H-NMR spectrum (CDCl ₃ , internal standard TMS) a 3.25 ppm (q, 2H) b 7.41 ppm (1H) c 3.01 ppm (s, 2H) d 2.54 ppm (q, 4H ) E 1.03 ppm (q, 6H) IR spectrum (KBr tablet) 1649 cm ^-1 , 1525 cm ^-1 Purity 97.9% (others; primary amine 0.6%, dimethylglycine 0.2%, chloride) Sodium 0.1%) ・ R ⁸ CH ₂ − Alkyl group composition C ₁₆ H ₃₃ / C ₁₇ H ₃₅ / C ₁₈ H ₃₇ / C ₁₉ H ₃₉ / C ₂₀ H ₄₁ = 5.2% / 2.3% /91.3
% / 0.3% / 0.9% Example 5 270.5 g of octadecanol and 0.1 g of potassium hydroxide were placed in an autoclave equipped with a stirrer and a thermometer, and dehydrated for 1 hour at a temperature of 120 ° C. and a vacuum degree of 2.6 kPa. After that, the mixture was cooled to a temperature of 60 ° C., 58.4 g of acrylonitrile was introduced over 1 hour, and the mixture was kept for 1 hour to complete the reaction. Next, 1.9 g of Raney nickel, 0.3 g of sodium hydroxide, and 16.1 g of ion-exchanged water were added, the hydrogenation reduction reaction was carried out at a temperature of 130 ° C. for 3 hours, and then the catalyst was removed by filtration. Further, it is purified by distillation to obtain the corresponding 3-octadecyloxypropylamine 294.
3 g was obtained.

Next, in a four-necked flask equipped with a stirrer, a thermometer, a dehydration tube, and a nitrogen introduction tube, 262.1 g of 3-octadecyloxypropylamine and 2.7 g of potassium sulfate obtained in the same manner as in Example 3. % Containing 41.1% N, N
-Prepare 220.8 g of dimethylglycine aqueous solution, and add 19
The temperature was raised to 0 ° C. After reacting for 7 hours at the same temperature while distilling off the produced water, the mixture was cooled to 80 ° C., and then unreacted N, N-dimethylglycine and potassium sulfate were removed by a Nutsche type filter to obtain the desired product. 316.9 g of aminocarboxylic acid amide which is a pale yellow solid was obtained. ¹ H-N
The following structure and composition were confirmed by MR spectrum, IR spectrum, gas chromatography, atomic absorption spectrometry and the like.

[0032]

[Chemical 9]

¹ H-NMR spectrum (CDCl ₃ , internal standard TMS) a 3.40 ppm (t, 2 H) b 3.48 ppm (t, 2 H) c 1.78 ppm (m, 2 H) d 3.38 ppm (m 2H) e 2.94 ppm (s, 2H) f 2.28 ppm (s, 6H) IR spectrum (KBr tablet) 1655 cm ^-1 , 1529 cm ^-1 , 1122 cm ^-1 Purity 95.3% (others; C ₁₈ H ₃₇ -OH 2.7%, C ₁₈ H ₃₇ -O-CH ₂ CH ₂ CH _2-
NH ₂ 0.8%, dimethylglycine 0.1%, potassium sulfate 0.1% or less) Comparative Example 1 A four-necked flask similar to that used in Example 1 was charged with Nissanamine V.
BS (Alkyl primary amine manufactured by NOF CORPORATION) 32
5.6 g, 1000 g of methanol as a solvent, and 9.6 g of a methanol solution of 28% sodium methylate as a catalyst.
Was added thereto, 113.9 g of methyl chloroacetic acid ester was added dropwise over 1 hour while maintaining the temperature at 30 to 40 ° C., and the mixture was reacted for 6 hours to obtain a 2-chloroacetamide reaction product. Next, 120.2 g of dimethylamine was introduced in 3 hours while maintaining the temperature at 50 to 60 ° C., and then reacted for 3 hours.
83.3 g of% sodium hydroxide was added. After that, the solvent methanol was distilled off at 80 ° C., and 443 g of water was added.
The mixture was stirred at 0 ° C. for 30 minutes, the layers were separated, and the aqueous layer was discarded. After performing the washing operation twice, the temperature is 80 ° C. and the degree of vacuum is 3.9 kP.
a, it was dehydrated in 1 hour. Next, 180 ° C, vacuum degree 1.3
Introduces 8.2 g of steam at kPa for 2 hours for deodorization,
390.3 g of aminocarboxylic acid amide which is a light brown solid
Got ^{From 1} H-NMR spectrum, IR spectrum, gas chromatography, atomic absorption analysis, etc., it has the same aminocarboxylic acid amide structure as in Example 1 and the same composition of the alkyl group represented by R ⁵ CH ₂ —. Was confirmed. The purity was 82%.

This method requires a large amount of reaction solvent and is expensive to manufacture. Further, the selectivity of the reaction is low, and if a high-purity product is to be obtained, a purification operation such as crystallization using an organic solvent is required and the yield will be low.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Toru Kato             Kao Co., Ltd. 1334 Minato, Wakayama City, Wakayama Prefecture             Inside the laboratory F-term (reference) 4H006 AA02 AC53 AD17 BC10 BC19                       BC31 BD20 BU32 BV23

Claims (5)

[Claims] 1. A compound represented by the general formula (I) R ¹ —NH ₂ (I), wherein R ¹ is a linear or branched alkyl group or alkenyl group having 8 to 40 carbon atoms, or R ⁵ O— ( AO) _n
—C _m H _2m — (R ⁵ is a linear or branched alkyl or alkenyl group having 8 to 40 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, n is an average value of 0 to 30, m is 2-3
And n of A may be the same or different). ] With a primary amine represented by the general formula (I
I) [Chemical 1] [In the formula, R ² is a linear or branched alkylene group having 1 to 5 carbon atoms, R ³ is a hydrogen atom, a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 1 to 24 carbon atoms, Alternatively, an aryl group or an arylalkyl group having 6 to 28 carbon atoms, R ⁴ is a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, an alkenyl group or a hydroxyalkyl group, or an aryl group having 6 to 28 carbon atoms. Represents a group or an arylalkyl group, and R ³ and R ⁴ may be alone or combined to form a ring. p is an integer of 1 to 3, q
And r are integers of 0 to 2, and p + q + r is 3. still,
The p R ¹ , R ² , the q R ³ , and the r R ⁴ may be the same or different. ] Amidation is carried out by reacting an aminocarboxylic acid represented by the following general formula (III): [Wherein R ¹ , R ² , R ³ , R ⁴ , p, q and r have the same meanings as described above. ] The manufacturing method of the aminocarboxylic acid amide represented by these. 2. R¹Is a straight chain having 12 to 24 carbon atoms or
A branched chain alkyl or alkenyl group, or the formula R^FiveO
-(AO)_n-C_mH_2m-(R^FiveIs a straight chain having 12 to 24 carbon atoms
Alternatively, a branched alkyl group or alkenyl group, A, n
And m have the above-mentioned meanings), R²Is carbon
Number 1 to 3 linear alkylene group, R³And R ^FourHas 1 to 1 carbon atoms
3 linear or branched alkyl group or hydroxy group
Rukyl group, or aryl group or ari having 6 to 10 carbon atoms
Alkyl group (R³And R^FourAre single or combined to form a ring
, P is 1 or 2, and q and r are 0 or 1.
The manufacturing method according to claim 1. 3. A primary amine 1 represented by the general formula (I)
The method according to claim 1 or 2, wherein the amidation reaction is carried out at a temperature of 120 to 250 ° C using 0.5 to 3 equivalents of the aminocarboxylic acid represented by the general formula (II) with respect to the equivalents. 4. The aminocarboxylic acid represented by the general formula (II) is obtained by adding an acid to an alkali metal salt of the aminocarboxylic acid, and the aminocarboxylic acid according to claim 1. Manufacturing method. 5. Washing with water or solid-liquid separation after amidation,
The manufacturing method according to claim 1.