JPH11315054A - Production of aluminum compound salt - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing an aluminum compound salt by reacting a dialkylaminophenylphenylenediamine with an acid or its salt, capable of producing the aluminum compound salt not containing iron metal by using a ferric complex. SOLUTION: This method for producing an aluminum compound salt of formula II (A is an anion residue such as the anion residue of sodium perchlorate, etc.), [for example, N,N,N',N'-tetrakis-(p-dibutylaminophenyl)-p- phenylenediamine aluminum perchlorate] comprises reacting an N,N,N',N'- tetrakis-(p-dibutylaminophenyl)phenylenediamine of formula I (R is H or a lower alkyl) with an acid or its salt in the presence of a ferric complex (for example, 1,3-propylenediaminetetraacetic acid ferric complex, ethylenediaminetetraacetic acid ferric complex, diethylenetriaminepentaacetic acid ferric complex, ethylenediaminedisuccinic acid ferric complex or 1,2-propylenediaminetetraacetic acid ferric complex).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for converting a compound containing a nitrogen atom to aminium to produce a salt thereof. The present invention relates to a method for producing an aminium salt, characterized in that when an inorganic acid residue salt of aminium, which is a product, is produced, the reaction is allowed to proceed using an iron complex salt.

[0002]

BACKGROUND OF THE INVENTION N, N, N ', N'-tetrakis- (p-dibutylaminophenyl) -p-phenylenediamine aminium perchlorate, one of the compounds produced in the present invention, has a wavelength in the infrared region. Has been widely known as a compound capable of strongly absorbing, but in recent years, it has been widely used as an auxiliary in the production of recording media, Can be broadly divided into a method by electrical oxidation and a method by chemical oxidation.
As disclosed in Japanese Patent Application Laid-Open No. 61-246391, a so-called electrolysis field device is required. On the other hand, a chemical method is to use a silver salt of various acids to form an acid residue salt of an aminium compound ( JP-B-43-25335) and a method using a ferric salt (Japanese Patent Laid-Open No. 3111447).

[0003] However, in the chemical method here, since a trace amount of the metal of the salt used in the reaction product is unavoidable, a salt of an aminium compound with high purity is required. Orientedly, the use of those made by these methods requires repeated purifications to remove trace amounts of contaminating metals. Japanese Patent Application Laid-Open No. 5-98243 has a detailed description of the inclusion of a trace amount of iron.

[0004]

SUMMARY OF THE INVENTION The present invention relates to a compound of the formula (1)

Wherein R is H or a lower alkyl group, an aminium compound salt of the formula (2)

Wherein R represents H or a lower alkyl group, and A represents an anion residue of an inorganic acid salt.

[0005]

Means for Solving the Problems The present inventor has repeated trial and error, and when producing a compound of the formula (2) from a compound of the formula (1) by a chemical method, the salt used in the reaction is used in the reaction. Although it was found that the solubility in the organic solvent used was a trace amount in the reaction product, it was found to be a cause of metal contamination, and the problem was solved by using a compound that was insoluble in the organic solvent used in the reaction. The present invention has been completed. That is, the present invention makes it possible to produce a compound of the formula (2) in which a reaction product does not contain iron metal by using a ferric complex salt as an iron compound capable of producing aminium.

Here, a ferric complex salt as an iron compound which can be used, that is, iron complex salts containing ferric ions include iron 1,3-propylenediaminetetraacetate complex, iron complex ethylenediaminetetraacetate, Examples include an iron complex of diethylenetriaminepentaacetic acid, an iron complex of ethylenediaminedisuccinate, and an iron complex of 1,2-propylenediaminetetraacetic acid. These complexes are not usually hindered even when used as they are, but are usually used as salts of alkaline compounds such as sodium, potassium, ammonium and amine. It seems that dissolving these ferric complexes in the necessary amount of water to dissolve them and subjecting them to the reaction would advantageously implement the present invention.

[0007] R in the compound represented by the formula (1) includes a hydrogen atom and a lower alkyl group such as methyl, ethyl, propyl, butyl and pentyl. Compounds represented by the formula (1) having these groups as R include lower alcohol solvents such as methanol, ethanol and propanol, ester organic solvents such as ethyl acetate, methyl acetate and butyl acetate, heptane and octane. , Petroleum solvents such as nonane, dimethylformamide,
A solvent such as dimethylacetamide, acetonitrile, acetone, methyl ethyl ketone, tetrahydrofuran, methyl cellosolve, ethyl cellosolve, or the like is used alone or as a mixture, dissolved in the solvent, and subjected to a reaction.

Next, A, which is a salt of an aminium compound in the formula (2), is an anionic residue of the salt of the acid used in the reaction. Potassium acid, sodium hexafluorophosphate, ammonium hexafluorophosphate, ammonium tetrafluoroborate, sodium tetrafluoroborate, potassium tetrafluoroborate,
Anionic residues such as sodium p-toluenesulfonate, potassium benzenesulfonate, sodium methanesulfonate, potassium ethanesulfonate, sodium trifluoroacetate and sodium benzoate.

Thus, when the compound represented by the formula (1), an acid or a salt thereof, and a ferric complex salt are appropriately reacted in a solvent, a salt of an aminium compound represented by the formula (2) is obtained. . Hereinafter, examples will be described in order to specifically explain the present invention.

【Example】

Example 1 Synthesis of N, N, N ', N'-tetrakis (p-dibutylphenyl) -p-phenylenediamine aminium monoperchlorate: N, N, N', N'-tetrakis (p-
Dibutylphenyl) -p-phenylenediamine 1.38
g of ethyl acetate, 6 ml of acetonitrile, 0.22 g of sodium perchlorate and 1.13 g of an ammonium salt of a ferric complex of 1,3-diaminopropanetetraacetic acid in 6 ml of water were added. Stirred at 30 ° C. for 6 hours. The reaction mixture was washed with water, concentrated under reduced pressure, n-heptane was added, and the precipitated crystals were collected by filtration and dried to give the title compound as a green powder. Obtained amount 1.19 g Yield 77.8% mp 162 ° C Maximum absorption wavelength 950 nm Molar extinction coefficient 2.1 × 10 ⁴

Example 2 Synthesis of N, N, N ', N'-tetrakis (p-dibutylphenyl) -p-phenylenediamine aminium monoperchlorate: In Example 1, conversion of 1,3-diaminopropanetetraacetic acid 1.13 g of ammonium salt of ferric complex
The title compound was obtained in the same manner as in Example 1, except that 2.78 g of an ammonium salt of a ferric complex of diethylenetriaminepentaacetic acid was used in place of the above. Yield: 1.24 g Yield: 81% Melting point and other characteristic values were the same as those of the compound obtained in Example 1.

Example 3 Synthesis of N, N, N ', N'-tetrakis (p-dibutylphenyl) -p-phenylenediamineaminium monotetrafluoroborate: N, N, N', N'-tetrakis (p -Dibutylphenyl) -p-phenylenediamine 4.15 g dissolved in ethyl acetate 45 ml, acetonitrile 18 ml, sodium fluoroborate 0.59 g
Was added, and 3.39 g of an ammonium salt of a ferric complex salt of 1,3-diaminopropanetetraacetic acid was dissolved in 18 ml of water and added. Stirred at 30 ° C. for 6 hours. Wash the reaction mixture with water,
After concentration under reduced pressure, n-heptane was added, and the precipitated crystals were collected by filtration and dried to obtain the title compound as a green powder. 2.74 g yield 60.4% mp 156 ° C. maximum absorption wavelength 950 nm molar extinction coefficient 2.4 × 10 ⁴

Example 4 Synthesis of N, N, N ', N'-tetrakis (p-dibutylphenyl) -p-phenylenediamine aminium monohexafluorophosphate: In Example 3, instead of 0.59 g of sodium fluoroborate The title compound was obtained by treating in the same manner as in Example 3 except that 0.88 g of ammonium hexafluorophosphate was used. Obtained amount 4.12 g Yield 85.8% mp 140-150 ° C. Maximum absorption wavelength 950 nm Molar extinction coefficient 2.5 × 10 ⁴

Reference Example 1 1.38 g of N, N, N ', N'-tetrakis (p-dibutylphenyl) -p-phenylenediamine was dissolved in ethyl acetate, 6 ml of acetonitrile, 0.22 g of sodium perchlorate and 1, 1.13 g of the ammonium salt of the ferric complex of 3-diaminopropanetetraacetic acid were added. Stirred at 30 ° C. for 6 hours. The reaction mixture was washed with water and concentrated under reduced pressure.
-Heptane was added, and the precipitated crystals were collected by filtration and dried to obtain a small amount of a compound as a green powder, but unreacted raw materials were recovered.

Claims (4)

[Claims] (1) Formula (1) (Wherein R is a compound represented by H or a lower alkyl group) is reacted with an acid or a salt thereof to produce an aminium compound salt, wherein a ferric complex salt is used. 2] Wherein R represents H or a lower alkyl group, and A represents an anionic residue. 2. The method according to claim 1, wherein R is n-
The method according to claim 1, wherein a salt of an aminium compound is produced using a compound that is a butyl group. 3. The method according to claim 1, wherein the ferric complex is iron ammonium 1,3-propylenediaminetetraacetate. 4. The method according to claim 1, wherein the ferric complex salt is used in the form of an aqueous solution.