JPH11322720A - Production of quaternary cyclic amidine organic acid salt - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for efficiently providing the subject organic acid salt free from a corrosive ion such as a heavy metal ion or a halogen ion by reacting a specific amide compound with an organic acid. SOLUTION: (A) An amide compound of di-substituted diamine of formula I (R1 is hydroxyl group, nitro, cyano or the like; R2 and R3 are each hydroxyl group, nitro or H; Q1 is a 1-5C hydrocarbon or hydroxyl group) is reacted with (B) an organic acid to provide the objective organic acid of formula II, e.g. 1,3-diethyl-2methyl-imidazolinium phthalate. Furthermore, the component B is selected from a group comprising carboxylic acid, mono or di- alkylphosphoric acid ester and reaction of the component A with the component B is preferably carried out at a molar ratio of 0.8-3 and e.g. N-methyl-N(N'- methylaminoethyl)formamide is preferably used as the component A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for producing a cyclic amidine organic acid salt having almost no corrosive ions such as heavy metal ions, alkali metal ions and halogen ions.

[0002]

2. Description of the Related Art As a method for synthesizing an organic acid salt of a quaternary cyclic amidine, a secondary and tertiary cyclic amidine are converted into an alkyl halide,
After quaternization with dialkyl sulfate or the like, a method of anion exchange with an organic acid salt of an alkali metal or an alkaline earth metal, or a method of quaternization with a carbonic acid diester to form a carbonate and anion exchange with an organic acid (JP-A-8-67672) )It has been known. However, it is extremely difficult to completely remove a halide or a sulfate of an alkali metal or an alkaline earth metal by a method of quaternization with an alkyl halide and anion exchange. In addition, it is difficult to industrially apply the method using diester carbonate other than dimethyl carbonate due to its reactivity.

[0003]

SUMMARY OF THE INVENTION The present invention provides a new quaternary cyclic amidine organic acid salt which is more efficient than conventional production methods and has almost no corrosive ions such as heavy metal ions and halogen ions. It seeks to provide technology.

That is, the present invention relates to a method for producing a quaternary cyclic amidine organic acid, which comprises a compound represented by the following general formula (1):
A method for producing a quaternary cyclic amidine organic acid salt represented by the following general formula (2), comprising reacting an amide compound (a) of a substituted diamine with an organic acid (b).

[0005]

Embedded image

[0006]

Embedded image

[In the formula, R1 represents a hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom which may have a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group. R2 and R3 each may have a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group;
Represents a hydrocarbon group having 1 to 20 carbon atoms. Q1 has 1 to 1 carbon atoms
5 alkylene having 2 to 10 carbon atoms which may be substituted with a hydrocarbon group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group;
Represents an arylene or alkenylene group. R1, R
A part or all of 2, R3 and Q1 may combine with each other to form a ring. ]

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Specific examples of the amide compound (a) of a disubstituted diamine serving as a raw material of the present invention include the following. (1) those in which R1 is a hydrogen atom (formamide) such as N-methyl-N- (N′-methylaminoethyl) formamide, N-ethyl-N- (N′-methylaminoethyl) formamide; Hydrocarbon group having 1 carbon atom (acetamide)
A hydrocarbon group having 1 carbon atom of R2 and having no substituent N-methyl-N- (N'-methylaminoethyl) acetamide, N-methyl-N- (N'- Methyl-2-aminopropyl) acetamide, N-methyl-N- (N'-methyl-3-aminopropyl) acetamide, N-methyl-N- (N'-methyl-2-aminophenyl) acetamide, N-methyl -N- (N'-acetylethylaminoethyl) acetamide, N-methyl-N- (2-hydroxy-3-methylaminopropyl) acetamide, N-
Methyl-N- (N'-formylethylaminoethyl) acetamide; a hydrocarbon group having 2 carbon atoms of R2 and having no substituent N-ethyl-N- (N'-methylaminoethyl) acetamide, N -Ethyl-N- (N'-ethylaminoethyl) acetamide, N-ethyl-N- (N'-methyl-
2-aminopropyl) acetamide, N-ethyl-N-
(N'-methyl-3-aminopropenyl) acetamide, N-ethyl-N- (N'-methyl-3-aminobutyl) acetamide, etc .; R2 is a hydrocarbon group having 3 to 20 carbon atoms and having a substituent. Not used N-propyl-N- (N'-methylaminoethyl) acetamide, N-phenyl-N- (N'-ethylaminoethylacetamide, N-benzyl-N- (N'-methylaminoethyl) acetamide, N -Butyl- (N'-methylaminopropenyl) acetamide and the like; a hydrocarbon group in which R2 has a substituent N-cyanomethyl-N- (N'-ethylaminoethyl)
Acetamide, N-hydroxyethyl-N- (N′-methylaminoethyl) acetamide, N- (N′-methylaminoethyl) acetamide-N-substituted-ethylene oxide 3 mol adduct and the like;

(3) R1 is a hydrocarbon group having 1 carbon atom (acetamido) having a substituent: N-methyl-N- (N′-methylaminoethyl) -2-
Hydroxyethylacetamide, N-ethyl-N- (2
-Methylaminopropyl) ethoxyacetamide and the like; (4) R1 having 2 to 20 carbon atoms and having no substituent N-isopropyl-N- (N'-ethylaminoethyl)
Propionamide, N-butyl-N- (N'-ethylaminoethyl) butylamide, N-ethyl-N- (N'-
Butylaminoethyl) isobutylamide, N-methyl-
N- (N'-methylaminoethyl) capronamide, N
-Methyl-N- (N'-methylaminoethyl) benzamide and the like; (5) R1 having 2 to 20 carbon atoms and having a substituent N-methyl-N- (3-aminopropyl) pyrrolidone;
N-ethyl-N-aminoethylpyrrolidone, N-methyl-N- (3-aminopropyl) caprolactone, N-phenyl-N- (3-aminopropyl) pyrrolidone, N-
Benzyl-N-aminoethylpyrrolidone, N-ethyl-
N- (3-aminopropyl) caprolactam, N-ethyl-N- (3-aminopropyl) acrylamide, N-
Methylaminoethyl-p-nitrobenzamide and the like;

Of these, preferred are N-methyl-N- (N′-methylaminoethyl) acetamide, N-ethyl-N- (N′-methylaminoethyl) acetamide, and N-ethyl-N- (N ′). -Ethylaminoethyl) acetamide, N-methyl-N- (N'-
Methyl-2-aminopropyl) acetamide, N-ethyl-N- (N'-methyl-2-aminopropyl) acetamide, N-methyl-N- (N'-methyl-3-aminopropyl) acetamide, N-methyl -N- (3-aminopropyl) pyrrolidone, N-ethyl-N-aminoethylpyrrolidone, N-methyl-N- (3-aminopropyl) caprolactone. Particularly preferred are N-methyl-N- (N'-methylaminoethyl) acetamide, N-ethyl-N- (N'-methylaminoethyl) acetamide, N-ethyl-N- (N'-ethylaminoethyl) Acetamide, N-methyl-N- (N'-
Methyl-2-aminopropyl) acetamide, N-ethyl-N- (N'-methyl-2-aminopropyl) acetamide, N-methyl-N- (N'-methyl-3-aminopropyl) acetamide.

An example of the production method (a) will be described. For example, in the case of N-ethyl-N- (N′-ethylaminoethyl) acetamide, 2-methylimidazoline is heated at 100 ° C.
To give N (N-aminoethyl) acetamide. This is treated with diethyl sulfate (ethylating agent) for 50 minutes.
Ethylated at １００100 ° C. to give N-ethyl-N- (N ′
-Ethylaminoethyl) acetamide sulfate is treated with an alkali at room temperature and purified by distillation under reduced pressure at a temperature of 140 ° C. or more and 5 mmHg or less. Similarly, N-methyl-N
-(N'-methyl-2-aminopropyl) acetamide is N-hydrolyzed 2,4-dimethylimidazoline.
(2-Aminopropyl) acetamide is methylated using dimethyl sulfate (methylating agent), and the obtained sulfate of N-methyl-N- (N′-methyl-2-aminopropyl) acetamide is treated with an alkali. And purified by distillation. N-ethyl-N- (N′-methylaminoethyl) acetamide is obtained by reacting diethyl carbonate with 2-methylimidazoline and selectively ethylating 1-ethyl-2-ethyl-2-ethylimidazoline.
Methyl imidazoline was synthesized, and N-ethyl- (N-aminoethyl) acetamide obtained by hydrolyzing 1-ethyl-2-methylimidazoline was methylated with a methylating agent such as dimethyl sulfate to obtain N-ethyl-N -Sulfate of (N'-methylaminoethyl) acetamide is treated with alkali and purified by distillation.

The organic acid (b) includes (1) a carboxylic acid such as a monocarboxylic acid {C1
30 aliphatic monocarboxylic acids [saturated monocarboxylic acids (formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, belargonic acid, lauric acid, myristic acid, stearic acid, behen) Acid) and unsaturated monocarboxylic acids (acrylic acid, methacrylic acid, oleic acid, etc.)] and aromatic monocarboxylic acids [benzoic acid, cinnamic acid, naphthoic acid, etc.]} and polycarboxylic acids (2- to 4-valent polycarboxylic acids). Carboxylic acid) ｛aliphatic polycarboxylic acid [saturated polycarboxylic acid (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid,
Suberic acid, azelaic acid, sebacic acid, etc.); unsaturated polycarboxylic acids (maleic acid, fumaric acid, itaconic acid, etc.)]; aromatic polycarboxylic acids [phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid) Acids, etc.]; aliphatic oxycarboxylic acids [glycolic acid, lactic acid, tartaric acid, etc.]; aromatic oxycarboxylic acids [salicylic acid, mandelic acid, etc.] and S-containing polycarboxylic acids [thiodipropionic acid], etc.

(2) phenols,
For example, monohydric phenol (including phenol and naphthol) [phenol; alkylphenols (cresol, xylenol, ethylphenol, n and isopropylphenol, n and isoamylphenol,
Methoxyphenols (eugenol, guaiacol, etc.); naphthol and cyclohexylphenol, etc.) and polyhydric phenols [catechol, resorcin, pyrogallol, phloroglysin, etc.], (3)
Mono and dialkyl phosphates [mono and dimethyl phosphate, mono and diisopropyl phosphate, mono and dibutyl phosphate, mono and di-
2-ethylhexyl) phosphates, mono- and diisodecyl phosphates, etc.] (4) Sulfonic acid [p-toluenesulfonic acid, dodecylbenzenesulfonic acid, sulfosalicylic acid, etc.]. Of these, preferred are formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, 2-ethylhexanoic acid, enanthic acid, caprylic acid, velargonic acid, lauric acid, benzoic acid, cinnamic acid, naphthoic acid. Acid, oxalic acid, malonic acid,
Succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, glycolic acid, Lactic acid, tartaric acid, salicylic acid, phenol, cresol, mono- and dimethyl phosphates, p-toluenesulfonic acid. Particularly preferred are phthalic acid, maleic acid, benzoic acid and 2-ethylhexanoic acid.

The amounts of (a) and (b) used are usually 0.8 to 3 in molar ratio. Preferably it is 1.0-3. When the molar ratio is less than 0.8, the conversion of the amide compound of the disubstituted diamine to the quaternary amidine cyclic compound is low, and the yield of the quaternary amidine cyclic compound is undesirably reduced.
When the number exceeds 3, the step (b) is wasted and a step of removing it if necessary becomes necessary.

In this reaction, (a) and (b) are directly mixed and heated to raise the temperature, or (a) is first placed in a reaction vessel,
After the temperature is raised, (b) may be dropped and reacted, or (b) may be put in a reaction vessel first, and after the temperature is raised, (a) may be dropped and reacted. However, in the latter method, the organic acid in the reaction system is 2
It is preferable because the amount of the amide compound of the substituted diamine is excessive. In any method, the reaction is carried out with stirring.

This reaction can be carried out in the presence of a solvent. As the solvent, water or a common organic solvent can be used. Water and an organic solvent and two or more organic solvents can be used in combination. Examples of usable organic solvents include alcohols, monohydric alcohols (eg, methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, diacetone alcohol, benzyl alcohol, amino alcohol, and furfuryl alcohol), and dihydric alcohols (ethylene glycol, propylene). Glycols, diethylene glycol, hexylene glycol, etc.), trihydric alcohols (eg, glycerin), tetrahydric or higher alcohols (eg, hexitol), etc .; ethers monoethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol) Monoethyl ether, ethylene glycol monophenyl ether, tetrahydrofuran, 3-methyl Amides formamides (N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N-ethylformamide, etc.), diethers (ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, etc.) and the like; , N
-Diethylformamide, etc.), acetamides (N-
Methylacetamide, N, N-dimethylacetamide,
N-ethylacetamide, N, N-diethylacetamide, etc.), propionamides (N, N-dimethylpropionamide, etc.), pyrrolidones (N-methylpyrrolidone, N-ethylpyrrolidone, etc.), hexamethylphosphorylamide, etc .;

Oxazolidinones N-methyl-2-oxazolidinone, 3,5-dimethyl-2-oxazolidinone, etc .; lactones γ-butyrolactone, α-acetyl-γ-butyrolactone, β-butyrolactone, γ-valerolactone, δ-valero Lactones and the like; nitriles acetonitrile, propionitrile, butyronitrile,
Acrylonitrile, methacrylonitrile, benzonitrile, and the like; other organic solvents such as dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, N-methylpyrrolidone, and aromatic solvents (toluene, xylene, and the like). Preferred are methyl alcohol, ethyl alcohol, propyl alcohol, benzyl alcohol, ethylene glycol, N, N-dimethylformamide, N-methylformamide, N-methylpyrrolidone, γ-butyrolactone, acetonitrile and benzonitrile. The amount of the solvent to be used is generally not more than 90% by mass, and preferably 80 to 5% by mass, based on the amide compound of the disubstituted diamine as the raw material and the organic acid.

The reaction temperature of this reaction is usually 50 to 200 ° C.
Preferably it is 80-200 degreeC. When the temperature is lower than 50 ° C., the reaction rate of the amide compound of the disubstituted diamine to the quaternary amidine cyclic compound is low. When the temperature exceeds 200 ° C., the quaternary amidine cyclic compound is decomposed. The reaction time is generally 6 to 24 hours, preferably 6 to 12 hours.

In the method of the present invention, the reaction can be carried out while removing by-product water out of the system. By removing the by-produced water, the reaction rate in the initial stage of the reaction can be increased, the entire reaction can be performed in a short time, and the reaction yield can be increased. As a method for removing by-produced water, a method of distilling out by distillation and a method of absorbing it into a dehydrating agent such as molecular sieves can be used, but a method by distillation is preferred from the viewpoint of yield and economy.
When water and a solvent by-produced after the reaction are used, the solid or viscous liquid obtained after removing the solvent is the desired quaternary cyclic amidine organic acid salt. If necessary, a high-purity product can be obtained by recrystallization or the like using an appropriate solvent.

The production method of the present invention can produce a quaternary cyclic amidine organic acid salt with high purity, which is efficient and has almost no corrosive ions such as heavy metal ions and halogen ions. The content of these ions is usually less than 3 ppm, preferably less than 1 ppm.

The quaternary cyclic amidine organic acid salt obtained by the method of the present invention can be used for various catalysts such as a surfactant, a phase transfer catalyst, a curing catalyst for urethane or epoxy resin, an electrolytic solution for electrolytic capacitors and electrochromic display devices. Is a useful organic compound that is used in a wide range of fields as an electrolyte, various additives, and chemicals.

[0022]

Hereinafter, embodiments of the present invention will be described.
The present invention is not limited to this. In the following, "parts" indicates parts by weight.

Example 1 SUS equipped with a thermometer, a device capable of dehydration under reduced pressure, and a stirrer
79 g of N-ethyl-N- (N′-ethylaminoethyl) acetamide and 83 g of phthalic acid (molar ratio of N-ethyl-N- (N′-ethylaminoethyl) acetamide: phthalic acid = 1: 1) 1) and the reaction temperature 1
The reaction was performed at 00 ° C. for 6 hours. Thereafter, unreacted substances and by-produced water were distilled off under reduced pressure of 120 ° C./5 mmHg, and 142 g of 1,3-diethyl-2-methyl-imidazolinium phthalate (yield; 98% of theoretical value) was obtained. Obtained. The purity was 99%. The purity of the obtained quaternary cyclic amidine organic acid salt was determined by using the peak area value of a chromatogram obtained by HPLC analysis, (peak area value of organic acid + peak area value of quaternary cyclic amidine) ア ミ (total peak area value). ) × 100
Was calculated by HPLC analysis conditions were mobile phase: 10
mM phosphoric acid / 100 mM sodium perchlorate aqueous solution, column: ODS column, detector: UV210 nm (light source:
Hg). As a result of ion analysis of organic acids, chlorine ion, sulfate ion, iron ion, copper ion, lead ion, sodium ion, and potassium ion were all less than 1 ppm.

Example 2 SUS equipped with a thermometer, a device capable of dehydration under reduced pressure, and a stirrer
79 g of N-ethyl-N- (N′-ethylaminoethyl) acetamide and 83 g of phthalic acid (molar ratio of N-ethyl-N- (N′-ethylaminoethyl) acetamide: phthalic acid = 1: 1) 1) and γ- as a solvent
357 g of butyrolactone was charged and reacted at a reaction temperature of 100 ° C. for 6 hours. Phthalic acid-1,3-diethyl-2-
149 g (yield; 99% of theory) of methyl-imidazolinium were obtained. Purity was 99%. The analysis method was the same as in Example 1. As a result of ion analysis of this organic acid, chlorine ion, sulfate ion, iron ion, copper ion, lead ion, sodium ion and potassium ion were all less than 1 ppm.

Example 3 In Example 1, N-methyl-N was replaced with 79 g of N-ethyl-N- (N′-ethylaminoethyl) acetamide.
-1,2,3,4-tetramethyl-imidazolinium phthalate 1 in the same manner as in Example 1 except that 72 g of-(N'-methyl-2-aminopropyl) acetamide was used.
41 g were obtained. (Yield; 98% of theory) The purity was 98%. The analysis method was the same as in Example 1. As a result of ion analysis of this organic acid, chlorine ion, sulfate ion, iron ion, copper ion, lead ion, sodium ion and potassium ion were all less than 1 ppm.

Example 4 SUS equipped with a thermometer, a device capable of dehydration under reduced pressure, and a stirrer
N-methyl-N- (N′-methyl-2-)
Aminopropyl) acetamide 72 g, benzoic acid 61 g
(Molar ratio of (N-methyl-N- (N'-methyl-2-aminopropyl) acetamide: benzoic acid = 1: 1)) and 289 g of γ-butyrolactone as a solvent were charged and reacted at a reaction temperature of 120 ° C. for 12 hours. . Benzoic acid ・ 1,
2,3,4-tetramethyl-imidazolinium is 122
g was obtained. (Yield; 99% of theory) Purity was 98%. The analysis method was the same as in Example 1. As a result of ion analysis of this organic acid, chlorine ion, sulfate ion, iron ion, copper ion, lead ion, sodium ion and potassium ion were all less than 1 ppm.

Example 5 SUS equipped with a thermometer, a device capable of dehydration under reduced pressure, and a stirrer
85 g of N-ethyl-N- (3-aminopropyl) pyrrolidone and 72 g of 2-ethylhexanoic acid
(Molar ratio of N-ethyl-N- (3-aminopropyl) pyrrolidone: 2-ethylhexanoic acid = 1: 1) was charged and reacted at a reaction temperature of 120 ° C. for 12 hours. afterwards,
Unreacted materials and by-produced water were distilled off at 120 ° C./5 mmHg under reduced pressure to give 2-ethylhexanoic acid / 1-ethyl-1,5-ethylhexanoate.
94 g (yield; 80% of theory) of diazabicyclo [4,3,0] nonene-5 were obtained. Purity was 95%. The analysis method was the same as in Example 1. As a result of ion analysis of this organic acid, chlorine ion, sulfate ion, iron ion, copper ion, lead ion, sodium ion and potassium ion were all less than 1 ppm.

Example 6 The procedure of Example 5 was repeated, except that 83 g of phthalic acid was used instead of 72 g of 2-ethylhexanoic acid.
1-ethyl-1,5-diazabicyclo phthalate [4,
116 g of 3,0] nonene-5 (yield; 85 of theoretical value)
%)Obtained. Purity was 96%. The analysis method is Example 1.
The same was done. As a result of ion analysis of this organic acid, chlorine ion, sulfate ion, iron ion, copper ion, lead ion,
1 ppm for both sodium and potassium ions
Was less than.

Comparative Example 1 SUS equipped with a thermometer, a device capable of dehydration under reduced pressure, and a stirrer
42 g of 2-methylimidazoline and 42 g of toluene were charged to a reaction vessel made of
00g was gradually added dropwise and reacted at the same temperature for 24 hours.
Unreacted materials and toluene were distilled off under reduced pressure of 100 ° C./5 mmHg to obtain 49 g (yield; 55% of theoretical value) of 1,3-diethyl-2-methylimidazolinium hydrochloride. Next, 40 g (0.226 mol) of hydrochloric acid / 1,3-diethyl-2-methylimidazolinium was dissolved in 100 g of methanol, and 12.2 g of sodium methoxide (0.226 mol) was dissolved.
Mol), and the mixture was allowed to react at room temperature for 1 hour. After cooling to 0 ° C., sodium chloride produced as a by-product was removed by filtration, 37.5 g (0.226 mol) of phthalic acid was added, and methanol was distilled off. 61 g (yield; 89% of theory) of the acid / 1,3-diethyl-2-methylimidazolinium were obtained. As a result of ion analysis of the obtained 1,3-diethyl-2-methylimidazolinium phthalate, chlorine ion and sodium ion were found to be 50 to 100 ppm. The analysis method was the same as in Example 1.

Comparative Example 2 SUS equipped with a thermometer, a device capable of dehydrating under reduced pressure, and a stirrer
42 g of 2-methylimidazoline and 177 g of diethyl carbonate were charged into a reaction vessel made of, and reacted at a reaction temperature of 130 ° C. for 24 hours. The reaction mixture was cooled to room temperature, and the reaction solution was analyzed by HPLC.
The conversion to diethyl-2-methylimidazolinium is 0.
%Met.

From Examples 1 to 6 and Comparative Examples 1 and 2, the production method of the present invention has a short reaction time, a high yield, and a high purity quaternary amidine cyclic compound free of heavy metal ions and halogen ions. This indicates that an organic acid salt can be obtained.

[0032]

The method of the present invention has the following effects. (1) The quaternary cyclic amidine organic acid salt obtained by the production method of the present invention has almost no corrosive ions such as heavy metal ions, alkali metal ions and halogen ions. (2) The electrolyte containing a quaternary salt as a solute obtained by the production method of the present invention has high specific conductivity and excellent durability. When used for an electrolytic capacitor, a long-life, highly reliable chip-type electrolytic capacitor having good soldering heat resistance, low loss and stable electric characteristics even at high temperatures can be obtained. Further, when used for an electrochromic display element, each part of the electrochromic display element that comes into contact with the electrolytic solution does not corrode, has a high specific conductivity, and can prolong the life of the electrochromic display element.

Claims (3)

[Claims] 1. A method for producing an organic acid salt of a quaternary cyclic amidine, comprising reacting an amide compound (a) of a disubstituted diamine represented by the following general formula (1) with an organic acid (b). A method for producing a quaternary cyclic amidine organic acid salt represented by the following general formula (2). Embedded image Embedded image [In the formula, R1 represents a hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom, which may have a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group. R2 and R3 each may have a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group;
Represents a hydrocarbon group of 0. Q1 is an alkylene, arylene or alkenylene group having 2 to 10 carbon atoms which may be substituted with a hydrocarbon group having 1 to 5 carbon atoms, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an ester group, an ether group or an aldehyde group. Represents Some or all of R1, R2, R3 and Q1 may be mutually bonded to form a ring. ] 2. The process for producing an organic acid salt of a quaternary cyclic amidine according to claim 1, wherein the organic acid is selected from the group consisting of carboxylic acids and mono- or dialkyl phosphates. 3. The organic acid salt of a quaternary cyclic amidine according to claim 1, wherein the amide compound (a) of the disubstituted diamine and the organic acid (b) are reacted at a molar ratio of 0.8 to 3. Manufacturing method.