4-(2-hydroxyethyloxy)-4'-cyanoazoxybenzene having liquid crystal stationary phase properties for gas chromatography

FIELD: chemistry.

SUBSTANCE: invention relates to a novel chemical compound - 4-(2-hydroxyethyloxy)-4'-cyanoazoxybenzene which can be used as a liquid crystal stationary phase for gas chromatography.

EFFECT: given compound has higher structural selectivity than structural isomers of lutidine.

1 ex, 1 tbl

 

Introduction

The invention relates to the chemical industry, namely to receive liquid crystals, in particular 4-(2-hydroxyethoxy)-4'-cyanoazobenzene, which can be used as a liquid crystal stationary phase for gas chromatography.

The level of technology

It is known that thermotropic liquid crystals can be used as stationary phase in gas chromatography. They show considerable selectivity in analytical separation of various substances, higher compared to conventional stationary phases in the separation bizcochada structural isomers [Vigdergauz, MS, Vigalok W., Dmitrieva, GV Chromatography in the system of gas - liquid crystal // USP, 1981, t, s-972].

Known liquid crystal stationary phase 4-methoxy-4'-etxezarreta [Egorova C.V., Belyaev, NV, Vigdergauz MSn,n'Methoxyethoxyethoxy as the preferred liquid-crystalline stationary phase chromatographic fragment of a universal system of chemical analysis, Izv. Higher education institutions. Chemistry and chem. technology., 1985, V.28, No. 6, p.3]. This liquid crystal stationary phase exhibits a sufficient selectivity relative to the low-boiling chemicals, in particular to p - and m-xylenes (selectivity factor α for xylenes 1,13), but may not be COI is used to separate chemical substances with higher boiling points, in particular 3,4 - and 3,5-lutidine.

Known liquid crystal stationary phase 4 Butylochka-4'-formulationsa [XVI international conference on chemical thermodynamics in Russia; X international conference on the problems of solvation and kompleksoobrazovanija in solutions. Suzdal, July 1-6, 2007, vol II, 4S-500. Kuvshinova S.A., Burmistrov V.A., Blokhin SV, Sharapova A.V., Fokin, D.S., I. Koifman Influence the associative status of the polar mesogens on their mesomorphism and structural selectivity].

However, this liquid crystal stationary phase shows low structural selectivity towards high-boiling isomers, in particular 3,4 - and 3,5-lutidine (α=1,27).

Known liquid crystal stationary phase bis(4-decyloxybenzoate)salicylal-N-dodecylamino]atomed [Crosses A.G., Blokhin SV, Galyametdinov YG, 'khovich M.V., Lobanov CENTURIES Sorbent based on mesomorphic complex of copper in the gas chromatography of organic compounds // J. physical Chemistry, 1993, CH, No. 1, s-154]. However, this liquid crystal stationary phase shows low structural selectivity towards high-boiling isomers, in particular 3,4 - and 3,5-lutidine (α=1,30).

The closest structural analogue of the claimed compounds is 4-cyanophenyl ether 4[4'-(2-hydroxyethyloxy)phenylazo]cinnamic acid [Burmester is in VA Kuvshinova S.A., I. Koifman, Blokhin SV, 'khovich M.V., Sharapova AV 4-cyanophenyl ether 4[4'-(2-hydroxyethyloxy)phenylazo]cinnamic acid, exhibiting the properties of liquid crystalline stationary phase for gas chromatography. RF patent №2323208 published 27.04.2008, bull. No. 12] following formula:

This compound exhibits liquid crystalline properties, contains a terminal substituents of the cyano-CN and 2-hydroxyethylacrylate BUT(CH2)2Oh, has some ability to separation of high-boiling positional isomers, in particular 3,4 - and 3,5-lutidine and can be used as liquid-crystalline phases in gas chromatography for the analysis of mixtures of organic compounds.

The main disadvantage of the 4-cyanovinylene ether 4[4'-(2-hydroxyethyloxy)phenylazo]cinnamic acid is not sufficiently high structural selectivity towards high-boiling isomers, in particular 3,4 - and 3,5-lutidine (α=1,30).

The invention

Inventive task is the search for new chemical compounds exhibiting liquid crystalline properties, which would have a higher structural selectivity for positional isomers lutidine.

The problem is solved by the compound 4-(2-hydroxyethoxy)-4'-cyanoazobenzene form the s:

The structure of the claimed compounds proven methods of elemental analysis, IR spectroscopy and NMR1N.

In the IR spectrum of 4-(2-hydroxyethoxy)-4'-cyanoazobenzene in tablets with KBr observed absorption band (the frequency in cm-1): ceanography - 2223, hydroxyl group - 3431, ties C-H aliphatic chain - 2853; 2923, ties C-H aromatic rings 1127-1734, ethoxypropan - 1265.

The NMR spectrum1H 4-(2-hydroxyethoxy)-4'-cyanoazobenzene in chloroform - D observed resonance signals of aromatic protons (chemical shifts in ppm relative to HMDS: 6,94 d (2N) and 6,92 d (2H); 7.87 in d (2N) and 7,84 d (2H); 7,78 d (2N) and 7.75 d (2H); 6.73 x d (2N) and 6,70 d (2N); the signals of the other groups 3,84 t (2H, O-CH2-), 5,1 (1H, H-O-).

The claimed compound has a high structural selectivity with respect to the structural isomers lutidine.

Information verifying the playback inventions

For the synthesis of 4-(2-hydroxyethoxy)-4'-cyanoazobenzene using the following ingredients:

1. 4-hydroxy-4'-cyanoazobenzene obtained by the method [Journal of organic chemistry, 1976, vol.12, issue 1, str-153].

2. Acetic acid GOST 19814-74.

3. Hydrogen peroxide (42%) GOST 177-88.

4. Ethylenchlorhydrine THE 6-01-05757587-58-94.

5. Potash GOST 4221-76.

6. Dimethylformamide TU 6-09-3720-79.

7. This is ol GOST 18300-87.

The claimed compound was obtained as follows.

Stage 1. of 2.23 g (0.01 mol) 4-hydroxy-4'-cyanoazobenzene dissolved in 50 ml of acetic acid and add 2,72 g (0.08 mol) of hydrogen peroxide in the form of a 42%aqueous solution. The mixture is heated with stirring on a water bath at 70°C for 1 h, cooled, the product is planted with water and filtered. Get a bright yellow crystals of 4-hydroxy-4'-cyanoazobenzene, TPL 128°C. the Yield 1.7 g (70%).

Stage 2. 2.4 g (0.01 mol) 4-hydroxy-4'-cyanoazobenzene, 0,81 g (0.01 mol) of ethylenchlorhydrine and 1.66 g (0.012 mol) of potash in 70 ml of dimethylformamide is boiled with vigorous stirring for 4 h Hot reaction mixture is poured into 250 ml of ice water, filtered and dried. The precipitate is recrystallized from ethanol.

Get the target product 4-(2-hydroxyethoxy)-4'-cyanoazobenzene. Yield 2.4 g (87%). TPL = 115°C, TP = 155°C.

Found (%): 64,02; N 4,91; N 13,89. Calculated (%): 64,65; N. Of 5.05; N 14,14.

Analysis of the obtained compound by means of polarizing microscopy (microscope Floors 211" thermostream) indicates the formation of a nematic phase in the temperature range 114,8-154,9°C.

Use of the claimed compounds as liquid crystal stationary phases in gas chromatography for the separation of positional isomers lutidine is illustrated by the following example.

A portion of the liquid crystal 4-(2-hydroxyethoxy)-4'-cyanoazobenzene in the amount of 0.6 g was dissolved in 30 ml of ethyl ether brand CHP. The resulting solution was added to 3.4 g of solid media brand Chromaton N-AW (0,40-0,63 Chemapol, Czech Republic) and heated on a water bath under stirring until complete evaporation of the solvent. To remove traces of ethyl ether are drying for 12 hours in vacuum at 100°C. and a residual pressure of 2 mm Hg Then the nozzle, which represents a solid support coated with a stationary phase, placed in a stainless steel column (1000×3 mm) and condition 6 hours in a stream of helium at 100°C. the Amount of stationary phase is 15% by weight of the nozzle. The constancy of the composition of the stationary liquid phase in the column is controlled by weighing the column before each series of experiments.

The retention times of the solutes was measured on a gas chromatograph Chrom-5 (Czech Republic) with a flame ionization detector with sensitivity, providing for the registration of the ionization current of 3.2·10-10A. the Measurements were carried out under isothermal conditions in the temperature range 100-200°C. the precise temperature control to 0.1°C. the Temperature of the evaporator and the detector set at 20°C above the temperature of the column. As the carrier gas used is helium with a basic substance content of 99.99%. The flow of helium is maintained within the range of 30-35 ml/min,measuring its foam flowmeter. The flow measurements performed at each temperature experience after determining the retention time of the sorbate. The outlet pressure equal to the atmospheric determine barometer BR-52 with a multiplier of 0.5 mm Hg To the conditions of the experiment corresponded to limiting dilution and concentration of the sorbate - linear isotherm plot of dissolution, in column injected small - not more than 0.1 μl - volume of the solutes. Use a syringe with a volume of 1 μl (Hamilton, Switzerland). "Dead" retention time is determined by the methane.

Selectivity factor for Herington determined by dividing the retention time of 3,5-lutidine at a retention time of 3,4-lutidine taking into account the "dead" retention time. Calculate an average selectivity factor of five measurements.

The test liquid stationary phase on the basis of the connection-prototype - 4-cyanovinylene ether 4[4'-(2-hydroxy-ethyloxy)phenylazo] cinnamic acid was similar to the testing of the claimed compounds.

The table shows the test results of liquid-crystalline stationary phases based on 4-(2-hydroxyethoxy)-4'-cyanoazobenzene and 4-cyanovinylene ether 4[4'-(2-hydroxyethyloxy)phenylazo]cinnamic acid.

Table data clearly confirm that the claimed compound has higher structural village of the activity in relation to positional isomers lutidine, what makes possible its use as a stationary phase for gas chromatography in the process of quantitative analysis of mixtures of organic compounds.

Table
The selectivity of stationary phases with respect to isomers lutidine.
N p/pStationary phaseThe column temperature, °CStructural selectivity, α
1.4-(2-hydroxyethoxy)-4'-cyanoazobenzeneof 101.51,75
110,31,69
123,11,66
131,71,61
2. the placeholder4-cyanophenyl ether 4[4'-(2-hydroxy-ethyloxy)phenylazo]cinnamic acid126,01,30

4-(2-hydroxyethoxy)-4'-cyanoazobenzene formula:
,
shows the properties of liquid-crystalline stationary F. the gases for gas chromatography.



 

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