1-piperidino-3-(4-pertenece)isopropyl ester of n - methylcarbamates acid as a biocidal additive for lubricating oils

 

(57) Abstract:

The use of the invention as biocidal additives for lubricating oils. The inventive product 1-piperidino-3-(4-pertenece)isopropyl ester of N-methylcarbamates acid f-ly BF C16H23FN2O3so pl. 170°C, yield 80%. Reagent 1: 1-piperidino-3-(4-pertenece)propanol-2. Reagent 2: methyl isocyanate. Reaction conditions: - CCl4in the presence of triethylamine at 30 - 35°C for 7 h 1 table.

The invention relates to new chemical compound, specifically to 1-piperidino-3-(4-pertenece)-isopropyl ether, N-methylcarbamyl acid of the formula I

which can find use as a biocidal additive for lubricating oils.

At the present time, it is important to study the scientific, technical, economic and environmental problems of the biological damage of materials and development of measures of struggle against them. Particularly relevant combat biodamage lubricating oils. So the microorganisms getting into the oil and directly consuming hydrocarbon components of the oil or acting on them by the products of their metabolism, causing oils irreversible changes and reduce their perfo is In oils precipitation is formed and resinous substances, that can lead to the deterioration of the mode of engine operation (1).

To prevent microbiological destruction oils in their composition is administered special antimicrobial additive is a biocide. As antimicrobial additives for lubricating oils of the proposed 8-oksihinolina and its derivatives, naphthenate metals, compounds containing arsenic, tin, mercury, boron compounds, etc. (2-4). However, most of them have several disadvantages that make it difficult to use in practice, significant toxicity to humans, narrow antimicrobial spectrum of action and adaptation of microorganisms. Therefore, the synthesis and study as biocidal additives to lubricating oils, new classes of organic compounds is of great interest.

The aim of the invention is the expansion of the range of substances exhibiting antimicrobial activity in lubricating oils, and the effectiveness of their actions.

This goal is achieved by the fact that as antimicrobial additives for lubricating oils offers a 1-piperidino-3-(p-pertenece)-isopropyl ester N-methylcarbamyl acid, which is synthesized by the interaction of 1-piperidino-3-(p-pertenece)-propanol-2 metalizing ether p-terfenol (5) with piperidine according to the method, described in (6).

Synthesis of 1-piperidino-3-(p-pertenece)-isopropyl ester was carried out as follows.

P R I m m e R. To a mixture of 25.4 g (0.1 mole) 1-piperidino-3-(p-pertenece)-propane - La-2, 60 ml of dry carbon tetrachloride and 0.5 g of triethylamine (catalyst) with stirring, added dropwise to 8 g (1,4 mol) of methyl isocyanate and stirred for 7 h at 30-35aboutC. Upon completion of the reaction the reaction mass is distilled off, the excess methyl isocyanate, triethylamine, carbon tetrachloride and the final product was recrystallized from isooctane.

Received 24 g (yield 80%) of the product so pl. 170aboutC.

Found, %: C 61,93; H 7,10; N 9,15.

C16H23FN2O3.

Calculated, %: C 61,93; H 7,41; N 9,03.

Building 1-piperidino-3-(p-pertenece)-isopropyl ether methylcarbamyl acid has been proved by IR and PMR spectroscopy.

In the infrared spectrum has absorption bands-NHC(O)-groups with a frequency of 1270 cm-1and ester group-C(O)-O - in the field 1225 cm-1. The absorption band 1715 cm-1characterizes the relationship of C=O in esters, and the absorption bands with frequencies 1205 and 1030 cm-1belong to the C-O and C-O-N-Bond NH p the second ring.

In the PMR spectrum includes signals of protons disubstituted benzene ring in the area 8726 M. D. proton of NH group manifests a complex signal in the area 5,35-5,80 m D. Quadropole with chemical shift 4,94 M. D. refers to the resonance of the proton group SN.

1-Piperidino-3-(p-pertenece)-ISO-propyl ether, N-methylcarbamyl acid was tested as antimicrobial additives to oil M-11. The tests were carried out according to GOST 9.05.75 and GOST 9.08.77 method of zonal diffusion using the following microorganisms:

Bacteria: Pseudomonas aeruginosa Mycobacterium lacticolum.

Fungi: Aspergillus niger, Chatomium globosum, Cladosporium resinae, Penicillum chrysogenum, Trichoderma viride and yeast-like microorganisms.

For growing bacterial cultures was used mastopathy agar (MPA), and for fungi and yeast - wort-agar (C/a).

The investigated compound and reference pentachlorophenolate sodium were added to the oil M-11 in weight percent units. Oil M-11 is a blend of distillate and residual (not less than 30%) oils phenol purification from sulfur crudes.

For the tests in Petri dishes poured nutrient medium in the amount of 20-25 ml and gave it to harden. Seeding of microorganisms was carried out on the surface of the pit is ubinas 4-5 mm, which added 0.5 to 0.8 ml oil M-11 with the specified connection. Then the Petri dishes were placed in a thermostat and kept for 2 days when using bacteria and 3-4 days for fungi at a certain humidity and temperature 302aboutC.

Similar tests were carried out with reference connection - pentachlorophenolate sodium.

The effectiveness of antimicrobial action 1-piperidino-3-(p-pertenece)-isopropyl ester N-methylcarbamyl acid was determined by the value of the diameter of zone of inhibition of growth of microorganisms.

The results are given in the table.

From the table it is seen that the proposed compound effectively inhibits the growth of microorganisms, affecting oil M-11. The necessary concentration of this compound is less than when using pentahlorfenolyata sodium. So, pentachlorophenol sodium at a concentration of 0.25% does not inhibit the growth of both bacterial and fungal microflora. Our connection not only at a concentration of 0.25%, but when 0,12% effectively inhibits the growth of microorganisms, affecting oil M-11. It should also be noted that the test compound does not adversely affect the physico-chemical properties of mA is raminosoa acid is recommended as a biocidal additive for lubricating oils.

1-Piperidino-3-(4-pertenece)isopropyl ester of N-methylcarbamates acid formula

< / BR>
as biocidal additives for lubricating oils.

 

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20 cl, 237 ex, 2 tbl

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21 cl, 6 tbl, 2 dwg, 4 ex

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12 cl, 2 ex, 1 tbl

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EFFECT: obtaining a lubricant composition for simultaneous run-in and preservation of internal combustion engines.

3 tbl

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