Tetra-(5-acetylamino-7-hydroxy)-anthraquinonoporphyrazines of copper and cobalt

FIELD: chemistry.

SUBSTANCE: invention relates to tetra-(5-acetylamino-7-hydroxy)anthraquinonoporphyrazines of copper and cobalt of formula

.

EFFECT: compounds can be used as dyes and catalysts.

4 ex, 6 dwg

 

Introduction

The invention relates to the chemical industry, namely, to obtain new derivatives metalloporphyrin - Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt as starting compounds for the synthesis of metal complexes of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric that can be used as dyes, catalysts, and other fields of science and technology.

The level of technology

The richest possibility of chemical modification of the compounds porphyrinogen series allows you to use them for different purpose, such as lightfastness of dyes and pigments [B. I. Stepanov introduction to the chemistry and technology of organic dyes. Educational. for universities. 3rd ed. Rev. and ext. M.: Chemistry, 1984. 592 S.], as catalysts for various processes [M. R. Tarasevich, Radyushkin K.A. Catalysis and electrocatalysis by metalloporphyrins. - M.: Nauka, 1982. 168 C., Stuzhinskaya TL Catalysts for the oxidation of sulfur compounds based on derivatives of phthalocyanine cobalt: Diss.... Kida. chem. Sciences. Novosibirsk. INSTITUTE OF CATALYSIS SB RAS. 1999. 131 S.].

The closest structural analogues of copper and cobalt complexes of the claimed compounds are Tetra-(5,8-dihydroxy)intrahemispheric cobalt and copper [Borisov A.V., Maizlish V.E., Shaposhnikov G.P. Way to obtain Metallica the complex of Tetra-(5,8-dihydroxy)intrahemispheric. Pat. RF 2277098 BI # 15 on 27.05.06] formula

However, these compounds do not possess solubility in organic media, therefore cannot be used as dyes and exhibit low catalytic activity.

The invention

Inventive task was to search for new derivatives metallocarboxypeptidase that when using them as initial products would give an opportunity to synthesize substituted tetranitroaniline having the properties of dyes and catalysts.

The problem is solved copper or cobalt complexes of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric formula

The structure of these compounds proved by data of elemental analysis, IR and electronic spectroscopy.

Thus, in the IR spectrum of the copper complex (figure 1) it is possible to allocate a number of common absorption bands with the unsubstituted analogue [K.Sakamoto, E.Ohno Synthesis of Cobalt Phthalocyanine Derivatives and their Cyclic Voltammograms // Dyes and Pigments. 1997. Vol.35. N4. P.375-386].

In the electronic absorption spectra of the Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt intensive absorption at 744-746 nm in concentrated sulfuric acid (2, 3), at 704 nm in dimethylformamide, at 694 nm in a 1%solution of hydroxide on the model.

The invention provides the following advantages: the use of Tetra-(5-acetylamino-7-hydroxy)antrahinonove-pyrazine copper and cobalt gives you the ability to synthesize metal complexes of Tetra-(5-acetylamino-7-heptyloxy)antrahinonove-Razin, having the properties of dyes and catalysts.

Information regarding the playback of the invention.

To implement the method using the following ingredients:

- Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt

- sodium hydroxide - GOST 2263-79.

The claimed compounds derived from Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt by hydrolysis them in 1%sodium hydroxide solution.

Because Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt are new compounds and are not produced by the industry, they were obtained in the following way: first, carry out the acylation with acetic anhydride m-anisidine, then the 1-acetylamino-3-methoxybenzoyl subjected to interaction with the dianhydride pyromellitic acid in the presence of anhydrous aluminum chloride, followed by intramolecular cyclization by treatment received in the second stage 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid concentrated sulfuric acid (MES is a hydrate). In the intramolecular cyclization receive 2,3-dicarboxy-5-acetylamino-7-methoxyacridine, from which then the method of the paid synthesis get Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt. Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt produced by hydrolysis of the latter in 1%sodium hydroxide solution.

Stage 1. Synthesis of 1-acetylamino-3-methoxybenzene.

In a flask equipped with a stirrer, thermometer and reflux condenser, dissolve 6.1 g (0.05 mol) of m-anisidine in 10 ml of toluene. Then placed in the flask and the solution gently for 15 minutes, poured 5.1 ml (0.5 mol) of acetic anhydride with heating of the reaction mass. After adding the total amount of acetic anhydride mixture is allowed to cool. The precipitated crystals acicular forms is filtered on a Buechner funnel. Washed with toluene in small portions until no odor of acetic acid, washed with water until neutral environment and dried at a temperature of 75-80°C.

Output: 1-acetylamino-3-methoxybenzoyl-6.5,

Stage 2. Synthesis of 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid.

In triggerlevel flask with a capacity of 100 ml equipped with a stirrer, reflux condenser and thermometer, is placed 10.0 g (0.046 mole) of the dianhydride pyromellitic acid, 8.42 g (0.051 mol) of 1-acetylamino the-3-methoxybenzene and 20 ml of heptane. The mass is heated to 50°C and with stirring add 16.12 g (0.119 mol) of anhydrous aluminum chloride. Stand 3 hours at boiling of the reaction mass (≈100°C), and after removal of the heptane another 6 hours at 120÷130°C. After cooling, to the reaction mass is added 50 ml of water and after soaking for 30 minutes, add hot soda solution and separating the precipitated precipitate aluminum hydroxide. To the aqueous layer of the filtrate add hydrochloric acid to pH 3-4. Precipitation 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid. It is filtered off, washed with water until neutral environment and dried at a temperature 75-8°C.

Output: 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid - 7.8,

Stage 3. Synthesis of 2,3-dicarboxy-5-acetylamino-7-methoxyacridine.

In a flask with a volume of 200 ml equipped with a stirrer and thermometer, was placed 10 ml monohydrate and heated to 130°C. and Then for 15 minutes with vigorous stirring, add 5 g of the obtained 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid, the temperature was raised to 150°C and incubated for 5 hours. The mass after cooling with stirring, poured into 200 ml of water, filtered, washed with a large amount of ice-cold water, dissolve in soda solution and acidified with hydrochloric acid. The precipitate is filtered off and washed with water until the disappearance of the chloride ions. Such processing surface is oraut twice. Dried at 100°C.

Output: 2,3-dicarboxy-5-acetylamino-7-methoxyacridine - 4.1, MP=360°C.

Stage 4. Synthesis of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt.

In a quartz ampoule put the pounded mixture of 0.23 g (0.60 mmol) of 2,3-dicarboxy-5-acetylamino-7-methoxyacridine 0.24 g (4.00 mmol) of urea, 0.036 g (0.18 mmol) of copper acetate or 0.037 g (0.18 mmol) of cobalt acetate, 0.02 g (0.40 mmol) of ammonium chloride and 0.002 g (0.01 mmol) of ammonium molybdate. The mass is slowly heated to 180°C for one hour and incubated for 3 hours. The resulting suspension is filtered, periostat of sulfuric acid and washed to conventional Soxhlet extractions with acetone for 10 hours. Dried at 100°C.

The output of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper - 0.13,

The output of Tetra-(5-acetylamino-7-methoxy)intrahemispheric cobalt - 0.12,

Synthesis of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt.

In a flask with a capacity of 25 ml with 10 ml of 1%sodium hydroxide solution introduce 0.1 g of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper or cobalt and heated in a water bath at 80°C for 40-50 minutes. The resulting suspension is filtered, periostat of sulfuric acid and washed to conventional Soxhlet extractions with acetone for 10 hours. Dried at 100°C.

Dark green substance solubility in DMF, 1%Rast is the PR of sodium hydroxide, concentrated sulphuric acid.

The output of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper - 0.09,

The output of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric cobalt - 0.08,

ESP copper complex in concentrated sulfuric acid, λmaxnm: 358, 641, 683 (figure 2).

ESP cobalt complex in concentrated sulfuric acid, λmaxnm: 358, 641, 684 (Fig 3).

Found, %: C, 62.22; H, 2.13; N, 12.20. C72N12H36O16Cu.

With 62.36; N, 2.55; N, 12.10. C72N12H36O16Co.

Calculated, %: C at 62.27; H, 2.61; N, 12.10. C72N12O16Cu.

C, 62.26; H, 2.62; N, 12.15. C72N12H36O16Co.

Example 1. Using as starting compounds, metal complexes of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric for the synthesis of copper and cobalt complexes of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric.

In odnogolosy flask of 50 ml equipped with a reflux condenser, a load 15 ml of DMF, 0.12 g of potash (K2CO3), 0.05 g of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper or cobalt, 4 ml of methyl heptyl (C7H15VG). The reaction mass is boiled for 24 hours, then poured into cold water, filtered and washed with hexane until no odor of methyl heptane, then with water, with acetone and subjected to sediment column, HRO is ecografia, sorbent - alumina II degree of activity, eluent - chloroform.

The output of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric copper: 0.04 g (85%).

The output of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric cobalt: 0.04 g (84%).

Dark green substance solubility in DMF, chloroform, o-xylene, concentrated sulfuric acid.

ESP copper complex in chloroform, λmaxnm: 358, 641, 683 (figure 4).

ESP cobalt complex in chloroform, λmaxnm: 358, 641, 684 (figure 5).

Found, %: C, 67.52; H, 5.13; N, 9.30. C100N12H92O16Cu.

C, 67.56; H, 5.15; N, 9.50. C100N12H92O16Co.

Calculated, %: C, 67.42; H, 5.21; N, 9.44. C100N12H92O16Cu.

C, 67.43; H, 5.21; N, 9.44. C100N12H92O16Co.

Example 2. The use of Tetra-(5-acetylamino-7-heptyloxy)-intrahemispheric copper as a dye for dyeing polyethylene and polystyrene.

The dyeing of polyethylene. 2 g of polyethylene is placed in a porcelain Cup and heated to melt, then pour in a solution of 5 ml of chloroform, which is dissolved 0.003 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper. Stand when heated to a complete removal of chloroform and the resulting mass is poured into the form.

The sample is attached. (see Fig.7.)

Dyeing polystyrene. 0.1 g of polystyrene are dissolved while heating the AI in 1 ml of benzene and add 1 ml of benzene, which is dissolved 0.002 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper. The solution is boiled for 3 minutes and the resulting mass is poured into the form.

The sample is attached. (see Fig.7.)

Example 3. The use of Tetra-(5-acetylamino-7-heptyloxy)-intrahemispheric cobalt as a dye for dyeing polyethylene and polystyrene.

The dyeing of polyethylene. 2 g of polyethylene is placed in a porcelain Cup and heated to melt, then pour in a solution of 5 ml of chloroform, which is dissolved 0.003 g of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric cobalt. Stand when heated to a complete removal of chloroform and the resulting mass is poured into the form.

The sample is attached. (see Fig.7.)

Dyeing polystyrene. 0.1 g of polystyrene are dissolved by heating in 1 ml of benzene and add 1 ml of benzene, which is dissolved 0.002 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric cobalt. The solution is boiled for 3 minutes and the resulting mass is poured into the form.

The sample is attached. (see Fig.7.)

Example 4. The use of Tetra-(5-acetylamino-7-heptyloxy)-intrahemispheric cobalt as catalyst for the oxidation of mercaptans.

Study of catalytic activity of the cobalt complex of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric spent 002 M solution diethyldithiocarbamate sodium (DDTC) at the facility, depicted in Fig.6.

For the preparation of heterogeneous catalyst solution of the cobalt complex of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric in DMF to a concentration of 0.01 mol/l in 50 ml immersed and fully impregnate the sample of non-woven polypropylene weight 2, Then the polypropylene remove and immerse in water to remove the organic solvent. When this happens fast crystallization and precipitation of the cobalt complex on the surface of the polypropylene fibers. The concentration of the complex on the surface of non-woven material such treatment is 1.5·10-5mol per 1 g of polypropylene. Thus obtained heterogeneous catalyst is placed in a glass DADD equipped with a CIRCULATOR pump 650 capacity 600 l/h to supply air required for oxidation at a constant speed of 2 l/min After the reaction mixture in the glass will be set at a constant temperature, select a sample of 2 ml to determine the initial concentration DADD and breathable. The time of air supply is taken for the start of the reaction. During the reaction after a certain period of time take samples of 2 ml for spectrometric determination of current concentration DADD.

The effective rate constant for the oxidation DADD is 2.6±0.4 sec-1.

Figure 1 - IR spectrum of the Tetra-(5-azeti the amino-7-hydroxy)-

intrahemispheric copper.

Figure 2 - Electronic absorption spectrum of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper in concentrated sulphuric acid.

Figure 3 - Electronic absorption spectrum of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric cobalt in concentrated sulphuric acid.

Figure 4 - the Electronic absorption spectrum of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper in chloroform.

Figure 5 - the Electronic absorption spectrum of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric cobalt in chloroform.

6 is a diagram of the setup for determining the activity of a heterogeneous catalyst: 1 thermometer, 2 - bubbler, 3 - glass, 4 - samples of a heterogeneous catalyst, 5 - pump, 6 - sampler 7 - reverse refrigerator.

Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt formulas



 

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