The method of producing phthalocyanine chloramine

 

(57) Abstract:

Describes a method of producing phthalocyanine chloramine, which can be used as a dye, a pigment, as an intermediate for obtaining dyes used in quantum electronics, as well as to obtain drugs "photosense" used for photodynamic therapy of malignant tumors. The method of producing phthalocyanine chloramine lies in the interaction of phthalonitrile and aluminium chloride, characterized in that the aluminium chloride are pre-treated with alcohol C1- C10and then heat the mixture with phthalonitrile at 160 - 210oC. the Technical result - the method eliminates the use of high-boiling organic solvents prevents the chlorination in the extension and provides phthalocyanine chloramine without admixture hydroxide with a sufficiently high yield.

The invention relates to the primary organic synthesis, in particular it concerns a method of producing phthalocyanine chloramine, which can be used as a dye, pigment; as an intermediate for obtaining dyes used in quantum e is AI malignant neoplasms [Lukyanets E. A. - Grew. Chem. J., T. 42, N 5, p. 9].

A known method of obtaining phthalocyanine chloramine from phthalonitrile and aluminum chloride by heating them at 250oC without solvent [F. H. Moser, Thomas A. L. - Phthalocyanine compounds. Reinhold Publ., 1963. P. 123], but in this case there is chlorination in the extension phthalocyanine with the formation of chlorthalidone chloramine. To prevent chlorination in the extension of the interaction of phthalonitrile and aluminum chloride can be mixed with sodium sulfate [e.g., British Patent 552,124 (1943)], but in this case it is necessary to heat the mixture at high temperature (250-270oC) and subsequent removal from the reaction mixture of significant quantities of salts.

Closest to the proposed technical solution is the method of receiving chlorthalidone aluminum, described in [Moser F. H., Thomas, A. L. - The phthalocyanines. CRS Press, 1983. V. 2. P. 4], where the receipt of aluminum phthalocyanine is carried out by the interaction of aluminum chloride and phthalonitrile in an organic solvent - trichlorobenzene. First, the described method is inconvenient due to the use of a high boiling point and is not miscible with water solvent, as a further purification is carried out by razborkami in aqueous acidic medium. Trubeckoy. Secondly, States that (and most significantly), apparently, the product is a mixture of two substances - phthalocyanine chloramine and phthalocyanine hydroxylamine.

The task of the invention was to develop such a method which would ensure obtaining phthalocyanine chloramine without impurities phthalocyanine aluminum hydroxide and chlorination products in the extension, while being quite effective and technologically.

The task was solved by pretreatment of aluminium chloride alcohols C1-C10followed by heating the resulting mixture at a temperature of 160-210oC, which resulted in the receipt of the product - phthalocyanine chloramine with high yield and purity. When carrying out the process at temperatures below 160oC the formation of the complex does not occur. Carrying out the process at temperatures above 210oC is not technological. Below is a reaction scheme:

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The following examples illustrate the invention.

Example 1. Getting phthalocyanine chloramine

Dissolve 13.3 g of aluminum chloride in 45 ml of ethanol, contribute with stirring 43 g phthalonitrile and continuing paramasivan>oC, stirred at this temperature with 250 ml of 10% hydrochloric acid for 30 min, the resulting suspension is filtered, the residue is again treated with hydrochloric acid, washed with water, then washed with hot acetone and dried. Obtain 32 g (68%) phthalocyanine chloramine with the content of the basic substance ~99%, according to the NMR spectrum-1N. Found, %: C1 5.93. WITH32H16AlClN8. Calculated, %: C1 6.17.Qmaxnmmol,l(MOLSS)) in H2SO4(conc.): 805 (234 000), in dimethyl sulfoxide: 676 (211 000).

Dissolve 1 g of the obtained phthalocyanine chloramine in 10 ml of concentrated sulfuric acid, stirred solution at room temperature for 2 h and poured onto 100 g of ice. The precipitate is filtered off, washed with water and razvarivat with 10% potassium hydroxide. After washing with water, washing with hot ethanol and drying receive phthalocyanine hydroxylamine, according to elemental analysis do not contain chlorine in the molecule.

Example 2

Phthalocyanine chloramine get analogously to example 1, using instead of ethanol butanol. The yield was 57%.

Example 3

Phthalocyanine chloramine get analogously to example 1, using instead of ethanol isamaru 1, instead of using ethanol methanol. The yield was 31%.

Example 5

Phthalocyanine chloramine get analogously to example 1, using instead of ethanol octanol. The yield was 49%.

Thus, the proposed method eliminates the use of high-boiling organic solvents prevents the chlorination in the extension, and provides phthalocyanine chloramine without admixture hydroxide with a sufficiently high yield. The developed method can be recommended for industrial development.

The method of producing phthalocyanine chloramine interaction phthalonitrile and aluminium chloride, characterized in that the aluminium chloride are pre-treated with alcohol C1- C10and then heat the mixture with phthalonitrile at 160 - 210C.

 

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