Tetra[4,5]([6,7]1-acetyl-2h-naphtho[2,3-d][1,2,3]triazole-5,8-dione)phthalocyanines of copper and cobalt

FIELD: chemistry.

SUBSTANCE: invention relates to tetra[4,5]([6,7]1-acetyl-2H-naphtho[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanines of copper and cobalt of formula , where M denotes Cu and Co.

EFFECT: invention enables to obtain novel derivatives of phthalocyanines which can be used as dyes, as well as catalysts for various processes.

2 ex, 6 dwg

 

Introduction

The invention relates to the chemical industry, namely, to obtain new derivatives of metallophthalocyanine - Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine and cobalt, which can be used as dyes for polymer materials, and catalysts for various processes.

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 analogue of the claimed compounds is a cobalt complex of Tetra-5,6-(1,2,3-benzotriazole)porphyrazine formula [A.E. Balakirev, Maizlish V.E., Shaposhnikov G.P. Porphyrazines cobalt with heterocyclic substituents // Journal of General chemistry. 2002, t, 337]:

However, this is Obedinenie cannot be used as a colorant for polymers and catalyst, because they are poorly soluble in organic media.

The invention

Inventive task was to search for new derivatives of phthalocyanines, which have the properties of the dye and, in addition, could be used as catalysts for various processes.

The problem is solved copper and cobalt complexes of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine of the formula

where M is Cu, Co.

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

Thus, the IR spectrum of the copper complex (figure 1) it is possible to allocate a number of common absorption bands with the unsubstituted analogue [.Sakamoto, E.Ohno Synthesis of Cobalt Phthalocyanine Derivatives and their Cyclic Voltammograms // Dyes and Pigments. 1997. Vol.35. # 4. P.375-386].

In the electronic absorption spectra of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine intensive absorption at 746 nm in concentrated sulfuric acid (2) at 689 and 644 nm in dimethyl sulfoxide (figure 3).

Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine and cobalt are substances of blue-green color. These compounds are soluble in concentrated sulfuric acid, dimethyl sulfoxide, dimethylformamide. Copper complex of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)FTL is tsianina has properties of dye to polymer materials, and cobalt exhibits catalytic properties.

Information regarding the playback of the invention.

To implement the invention using the following ingredients:

- 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid

- urea - GOST 2081-92

- copper acetate - GOST 5852-70

- cobalt acetate - GOST 5861-79

- ammonium molybdate - GOST 2677-78

The claimed compounds produced by interaction of 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid with urea, ammonium chloride, ammonium molybdate and copper acetate or cobalt in the reaction conditions templates tetramerization.

Since 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid is a new connection and not produced by the industry it was obtained in the following 3-stage method: first, carry out the acylation of benzotriazole acetic anhydride, and then the obtained product is subjected to acylation interaction with dianhydride pyromellitic acid in the presence of anhydrous aluminum chloride, followed by intramolecular cyclization by treatment received at the first stage, 5-[(1-acetyl-2H-1,2,3-benzotriazol-5-yl)carbonyl]benzene-1,2,4-tricarboxylic acid, concentrated sulfuric acid (monohydrate). As a result, nutrim the molecular cyclization get 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid.

Stage 1. Synthesis of 1-acetylbenzoate. In a round-bottom three-neck flask with a capacity of 100 ml dissolve 11.9 g (0.1 mol) of benzotriazole in 20 ml of toluene. The flask connected with a reflux condenser and placed in the flask and the solution gently for 15 minutes, poured to 11.3 ml (0.12 mol) of acetic anhydride. When this reaction mixture is heated to boiling. 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 and air-dried between sheets of filter paper

Output 1-acetylbenzoate 11,

Stage 2. Synthesis of 5-[(1-acetyl-2H-1,2,3-benzotriazol-5-yl)carbonyl]benzene-1,2,4-tricarboxylic acid. In a three-neck 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, 8.21 g (0.051 mol) of 1-acetylbenzoate 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. To the cooled mass consistently add 50 ml of water and 10 ml of concentrated hydrochloric acid and stirred for 12 hours. Sediment AHP crystal growth is litrovuyu, washed with hot water and boil for 30÷40 minutes in a 10%solution of soda. The hot solution is filtered, the precipitate is treated in this way 3-4 times. The filtrate is acidified with hydrochloric acid to pH 4 and cooled to 10÷15°C. the precipitation is filtered off, washed with water until neutral. Dried at 80°C.

Output 5-[(1-acetyl-2H-1,2,3-benzotriazol-5-yl)carbonyl]benzene-1,2,4-tricarboxylic acid 7,

Stage 3. Synthesis of 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid. In a three-neck flask of 100 ml equipped with a stirrer, reflux condenser and thermometer, was placed 20 ml (0.18 mol) of monohydrate and heated to 130°C. and Then for 15 minutes with vigorous stirring, add 5 g (0.011 mol) of the obtained 5-[(1-acetyl-2H-1,2,3-benzotriazol-5-yl)carbonyl]benzene-1,2,4-tricarboxylic acid, the temperature was raised to 150°C and maintained for 5 hours. The mass after cooling with stirring, poured into 200 ml of water, filtered, the precipitate 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 is repeated twice. Dried at 100°C.

Output 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid, 4.1,

Synthesis of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole and 5-dione)phthalocyanine copper and cobalt. In a quartz ampoule put the pounded mixture of 0.23 g (0.60 mmol) of 1-acetyl-5,10-deoxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid, 0.24 g (4.00 mmol) of urea, 0.036 g (0.18 mmol) of copper acetate or 0.036 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. After cooling, the reaction mass is crushed, transferred to a filter Shota, washed with 5%hydrochloric acid and then with water until the wash liquid when applying the drops on a glass slide and evaporation remains solid residue. Dried at 100°C. Then periostat of concentrated sulfuric acid and washed to conventional Soxhlet extractions with acetone for 10 hours. Dried at 100°C.

The output of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine 0.13,

The output of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine cobalt 0.12,

The target products are a blue-green substance having a solubility in concentrated sulfuric acid, dimethyl sulfoxide, dimethylformamide.

ESP Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine in dimethyl sulfoxide. λmaxnm: 352, 644, 689 (figure 3).

ESP Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine cobalt in dimethyl sulfoxide. λax nm: 352, 646, 688 (figure 4).

Found, %: C 60.52; H, 1.98; N 19.62. C72H28N20O12Cu.

With 60.70; H 1.97; N 19.64; C72H28N20O12Co.

Calculated, %: C 60.53; H 1.98; N 19.61. C72H28N20O12Cu.

With 60.73; H 1.98; N 19.67; C72H28N20O12Co.

Example 1. The use of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine 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 5 ml Dima-tranfixed, which is dissolved 0.003 g of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D[1,2,3]triazole-5,8-dione)of copper phthalocyanine. Stand when heated to completely remove the dimethyl sulfoxide and the resulting mass is poured into the form.

The sample is attached (Fig.6 and 7).

Dyeing polystyrene. 2 g of the polystyrene is placed in a porcelain Cup and heated to melt, then pour in 5 ml of dimethyl sulfoxide, which is dissolved 0.003 g of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)of copper phthalocyanine. Stand when heated to completely remove the dimethyl sulfoxide and the resulting mass is poured into the form.

The sample is attached (Fig.7).

Example 2. The use of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine cobalt as catalyst oxide is placed mercaptans.

Study of catalytic activity of the cobalt complex of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine was carried out on 0.02 M solution diethyldithiocarbamate sodium (DETC) on the setup depicted in figure 5.

The installation contains: 1 thermometer, 2 - bubbler, 3 - glass, 4 - samples of a heterogeneous catalyst, 5 - pump, 6 - sampler 7 - reverse refrigerator.

For the preparation of heterogeneous catalyst in 50 ml of a solution of the cobalt complex of Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine in DMF to a concentration of 0.01 mol/l immersed and fully impregnate the sample of non-woven polypropylene weight 2, Then the sample is removed and immersed 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 the nonwoven material when such processing is 1.9·10-5mol 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 establishment in the reaction mixture in a glass of constant temperature selected a sample of 2 ml to define which of 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 3.2±0.3 sec-1.

Tetra[4,5]([6,7]1-acetyl-2H-oil[2,3-D][1,2,3]triazole-5,8-dione)copper phthalocyanine and cobalt formulas

where M is si, With.



 

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