Way to obtain the disodium salt of n,n-bis-(4-amino-2 - sulfophenyl)piperazine

 

(57) Abstract:

The invention relates to a method of production of new chemical compounds, diamine consisting of aromatic and cycloaliphatic fragments, specifically disodium salt of N,N-bis-(4-amino-2-sulfophenyl)piperazine, which can be used as a monomer in producing high-strength heat-resistant cation-exchange materials. The technical result is the synthesis of new monomers for polycondensation cation containing macromolecular chain fragments with two sulfo, which can significantly increase the ion-exchange process, without compromising the characteristics of the polymer (temperature resistant, chemical-resistant and others).

The invention relates to the field of organic chemistry, in particular the method for producing a diamine containing sulfopropyl and consisting of aromatic and cycloaliphatic fragments, specifically to the disodium salt of N,N-bis-(4-amino-2-sulfophenyl)piperazine of the formula:

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which can be used as a monomer to obtain a cation-exchange materials.

Currently, the industry produced a cation - aromatic chain polymers of various grades of Oia their receipt, based on the sulfonation chain polymers, leads to the degradation and oxidation of the macromolecular chain. It will not make it possible to obtain polymeric materials with reproducible characteristics.

Synthesis of high-molecular compounds based on the use of monomers containing sulfopropyl, eliminates these drawbacks.

The aim of the invention is a method of synthesis of a new compound is disodium salt of N,N-bis-(4-amino-2-sulfophenyl)piperazine according to the scheme:

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The method consists in the following. The first stage of this process is the nucleophilic substitution of the chlorine atom, activated in the ring nitro and sulfo on reactive piperazine (pKa = 9,82) [albert A. , Sargent E. ionization Constants of acids and bases M.: Chemistry, 1964, c.142]. The output at this stage is to 92.4%. The second stage is to restore the received dinitropropanol of Dolinina using carbonyl iron in the presence of hydrochloric acid. After treatment of the reaction solution in the excess of 20% solution of sodium hydroxide produce the disodium salt of N, N-bis-(4-amino-2-sulfophenyl)piperazine. The yield of the final product of 85.1%.full-time [C. A. Subbotin, S. C. GITIS, Aromatic diamines-monomers for polyamides, Moscow, Izd-vo'toole. state PED. University, 1988, S. 192] reactivity (pKa = 4,6) readily reacts poly - and copolycondensation with dichloromethane Tere - and isophthalic acids. When this is formed with sufficient molecular weight poly - and copolyamids. The good solubility of the monomer allows polyamidoamine mortar (amide solvents) and interfacial (tetrahydrofuran water-ways.

The essence of the invention is illustrated by the following examples.

Example 1. Obtaining N,N-bis-(4-nitro-2-sulfophenyl)piperazine.

To aqueous solution of 0.15 mole of piperazine and 0.03 mol of 4-nitrochlorobenzene-2-sulfonic acids were added 5 g of MgO and were heated to 95-98oC with constant stirring. After 12 h the mixture was filtered from the excess MgO, and the filtrate was further subjected to recover without additional purification.

The structure of dinitropropyl proven PMR spectra.

M. D. H3: 8.69 D. (2H. J2.6 Hz); H5: 8,05 D. D. (2H.J 8.7 and 2.6 Hz);

H6: 7,03 D. (2H.J8.7 Hz); CH2: 3,67 S. (8H)

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Example 2. Obtaining N,N-bis-(4-amino-2-sulfophenyl)piperazine.

To 25 ml of hydrochloric acid (1:1) and 10 g carb is the completeness of the recovery was implemented fault has flowed out.

The resulting product was filtered from unreacted iron, and the filtrate is brought to the slightly alkaline environment of 20% sodium hydroxide solution. The resulting iron hydroxide was filtered, and the solution was evaporated to dryness.

The reduction product was treated with ethyl alcohol, then the alcohol extract was subjected to evaporation. The selected product in the form of sodium salt was subjected to the purification of the acid-basic presidenial.

The structure of the synthesized monomer proved by data of elemental analysis and spectroscopic.

Calculated, %: C to 40.6; H 3,8; Na 9,7; 11,8 N; S 13,5; O 20,3

C16H18N9S2O6< / BR>
Found, %: C, 40,4; H 3,9; N 10,1; 11,6 N; S 13,3

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M. D. H3: 7.16 D. (2H. J 2.6 Hz); H5: 5.56mm D. D. (2H. J 8.7 Hz);

H6: 6,88 D. (2H. J 8.7 Hz); CH2: 2,85 S. (8H)

Example 3. Obtaining a polyamide-based disodium salt of N,N-bis-(4-amino-2-sulfophenyl)piperazine and dichlorohydrin isophthalic acid.

0.04 mol (18,88) disodium salt of N, N-bis-(4-amino-2-sulfophenyl)piperazine was dissolved in 100 ml of dimethylacetamide. The resulting solution was cooled to 8oC and with stirring was added 0.04 mole (8,18 g) dichlorohydrin isophthalic acid. The reaction mass you is the result received 23,36 g of the polymer powder, that is 97% of theoretical. The specific viscosity of 0.5% in dimethylacetamide is 0.82, static exchange capacity of the polymer of 6.4 mEq/g, the mass loss of the polymer in 360oC is 6%.

Way to obtain the disodium salt of N,N-bis-(4-amino-2-sulfophenyl)piperazine, namely, that 4-nitrochloro-benzene-2-acid is subjected to interaction with piperazine by nucleophilic substitution of the chlorine atom of the sulfonic acids and subsequent reduction of the resulting N,N-bis-(4-nitro-2-sulfophenyl)piperazine and translation of the resulting product in the disodium salt of the formula



 

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