2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine as an intermediate in the synthesis of surfactants

 

(57) Abstract:

The invention relates to organic chemistry, in particular to derivatives of 1,3,5-triazine and 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine structure

as an intermediate in the synthesis of cationic type surfactants.1 N. p. F.-ly, 1 table.

The invention relates to organic chemistry and chemistry of surface-active substances (surfactants), specifically to new substituted 1,3,5-triazine-2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) structure

as an intermediate in the synthesis of cationic type surfactant.

As you know, the chemistry of surfactants is booming. This is due not only to the level of sanitary-hygienic preparation of the population, but also the need to develop new, effective, non-toxic and do not cause allergic reactions of compounds capable of lowering the surface tension of liquids and having good detergency even in hard water. The last condition is the best answer cationic type surfactant, a range which, unfortunately, is very limited. Development of new cationic surfactants of the type of task is most important.

Its use as surface-active substances is unknown.

Known also Tetramethylammonium chloride (TMAH) structure

The specified connection get known quaternization reaction of dimethylaminoacetyl chloride stands for Hoffman and used as cationic surfactants (cationic surfactant) [see Surfactants and compositions. The Handbook. /Ed. by M. Y. Pletnev. - M.: OOO “firma Clavel”. 2002. - 768 C.]. TMAH used as surfactants and conditioning supplements in conditioners and balms (prototype).

The disadvantage of applying CMAH is relatively low ability to reduce the surface tension of aqueous solutions, as well as the high acidity of solutions.

Technical solution to the problem is to increase the ability to reduce the surface tension of water which is achieved by to increase surface activity and reduce the acidity of the solutions proposed to use the newly synthesized intermediate in the synthesis of surfactant - 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) structure

The novelty of the claimed proposal is seen that the proposed synthesis of a new compound HNAT, the use of which as an intermediate allows to synthesize a new cationic type surfactant (cationic surfactant), which reduces the surface tension and the acidity of aqueous solutions in comparison with known CMAH.

At the same time declared 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) get known method, the reaction of cyanuric chloride with p-toluensulfonate-methylamine (1:2 mole) in solution in acetone, in the presence of equimolar amount of sodium bicarbonate [see C. N. Zaplishny, I. A. Asaturyan, G. M. Poghosyan. Synthesis Djalilov esters of 2-piperidyl-4,6-diglycyl-s-triazine. - Arm.chem.J., 1976, T. 29, No. 12, S. 1065-1067].

Source cyanuric chloride immediately before use purify by crystallization from CCL4and the solvent is subjected to fractionation and dried by known methods using known cationic surfactant Tetramethylammonium (TMAH) - the prototype application.

Examples of specific performance of the alleged proposal (synthesis of intermediate HNAT and surfactants based on it) are presented below in examples 1-4.

Example 1. 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT). A mixture of 1.5 g (0.02 mol) aminouksusnoy acid, 3,47 g (0.02 mol) of nonanol-1 and 3.8 g (0.02 mol) of p-toluenesulfonic acid in 25 ml of benzene is boiled with a nozzle Dean-stark and reflux to the visual termination of water in the nozzle. The mixture is boiled for a further 3 h, distilled benzene to half volume, and the residue is distilled to dryness in a water jet vacuum on a water bath. Get 3.5 g (91%) p-toluensulfonate danilovogo ester of glycine (TSG) as a white, amorphous and highly hygroscopic substance with so pl. 25-27°C.

Found, %: C 58,11; N 8,58; N 3,52; C18H31NSO5. Calculated, %: C 57,88; N. Of 8.37; N 3,75.

X , cm-1: 3430-3300 ush.with. (-NH+3); 1720 cf. (C=0); 1630, 1595, 1500 cf. (C=C, C=N - t. and cyanurates cycle.); 1140, 1100, 1015 cf. (C-O-C).

DMR , M. D. (group): 7,55-the 7.65 (2H D., N.2+N6hair dryers) J=8,3; 6,83-7,01 (2N D., N.3+N6hair dryers) J=8,3; of 5.05 (3H, S., NH+3); 4,04-4,29 (N m, -(CH2)6-); 3,96-4,01 (2N so, och2); 3,88-to 3.92 (2H m, NH+3

To a solution of 0,86 g (0,0047 mol) of cyanuric chloride in 15 ml of acetone was added 3.5 g (0,0094 mol) obtained TSG and under stirring and the temperature of 5-7°C in small portions was added 1.56 g (0,0186 mol) of sodium bicarbonate. The reaction mixture was stirred for another 1 h at the same temperature, 2 hours at 20 and 12 h at 40°C. the Mixture is evaporated in a water jet vacuum to dryness, the residue is thoroughly washed with water and purified by crystallization from alcohol with activated carbon. After drying obtain 2.0 g (83%) of 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) as a white crystalline substance with so pl. 121-123°C.

Found, %: C 58,70; N 8,81; N 13,48. C25H44N5O4Cl. Calculated, %: 58,39; N To 8.62; N 13,62.

X , cm-1(group): 3230, 3070 cf. (N-H); 1735 S. (C=0); 1570, 1550 cf. (C=C, C=N - t. and cyanurates cycle.); 1120, 1065 cf. (C-O-C).

DMR , M. D. (group): 7,54-to 7.99 (2H, ush.S., NH); 3,99-4,00 (m, 4H, OCH2); 3,82-of 3.96 (m, 4H, NCH2); 1,55-of 1.64 (4H square, CH2CH3) J=6,0; 1,16-1,40 (24N m, CH2CH2CH2); or 0.83 to 0.92 ( 6N so, CH3) J=6,0.

Mol. ion (mass by a spectroscope) 514.

Example 2. 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT). Under conditions analogous to example 1, from the same quantities cyanuramide obtain 2.1 g (87%) of 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) as a white crystalline substance with so pl. 121-123°C.

Found, %: C 58,70; N 8,81; N 13,48. C25H44N5O4Cl. Calculated, %: 58,39; N To 8.62; N 13,62.

X , cm-1(group): 3230, 3070 cf. (N-H); 1735 S. (C=0); 1570, 1550 cf. (C=C, C=N - t. and cyanurates cycle.); 1120, 1065 cf. (C-O-C).

DMR , M. D. (group): 7,54-to 7.99 (2H, ush.S., NH); 3,99-4,00 (m, 4H, och2); 3,82-of 3.96 (m, 4H, NCH2); 1,55-of 1.64 (4H square, CH2CH3) J=6,0; 1,16-1,40 (24N m, CH2CH2CH2); or 0.83 to 0.92 (6N so, CH3) J=6,0.

Mol. ion (mass by a spectroscope) 514.

Thus obtained HNAT then used for obtaining surfactants in examples 3 and 4.

Example 3. 2-Trimethylammoniumchloride-4,6-bis(nonlexical-ylmethylamino)-1,3,5-triazine (TCT). Through a solution of 2.0 g (to 0.0039 mol) HAT in 20 ml of a mixture of absolute benzene and ether (1:1 by volume), with stirring and at a temperature of 20°C, in a weak stream of nitrogen bubbled dry trimethylamine within 4 h Formed abundant precipitate is filtered off, washed with dry benzene (210 ml) and dried. Obtain 1.8 g (89,6%) target TNCT in the form of a white crystalline powder with so pl. 133-145°N

Found, %: C 58,49; N 9,11; N 14,78. C28H53N6O4Cl. Calculated, %: C 58,66; N 9,31; N 14,66.

X , cm-1(group): 3090, 3060 cf. (N-H); 1739 S. (=O5-8,99 (2H, ush.S., NH); 4,00-4,10 (m, 4H, och2); 3,85-of 3.97 (m, 4H, NCH2); 3,25 (N S., NMe3); 1,57-of 1.65 (4H square, CH2CH3) J=6,0; 1,20-1,40 (24N m, CH2CH2CH2); 0,85-0,93 (6N so, CH3) J=6,0.

Mol. ion (mass by a spectroscope) 573.

Example 4. 2-Trimethylammoniumchloride-4,6-bis(nonyloxy-carbonylmethyl)-1,3,5-triazine (TCT). Under conditions analogous to example 3, 2.0 g (to 0.0039 mol) HNAT and dry trimethylamine with the only difference that the bubbling continued for 3.5 h at 15°C, gain of 1.87 g (93%) TNCT in the form of a white crystalline powder with so pl. 133-145°N

Found, %: C 58,49; N 9,11; N 14,78. WITH28H53N6O4CL. Calculated, %: C 58,66; N 9,31; N 14,66.

X , cm-1(group): 3090, 3060 cf. (N-H); 1739 C. (C=O); 1595, 1530 cf. (C=C, C=N - t. and cyanurates cycle.); 1220 cf. (NMe3); 1065, 1030 cf. (C-O-C).

DMR , M. D. (group): 7,55-8,99 (2H, ush.S., NH); 4,00-4,10 (m, 4H, och2); 3,85-of 3.97 (m, 4H, NCH2); 3,25 (N S., NMe3); 1,57-of 1.65 (4H square, CH2CH3) J=6,0; 1,20-1,40 (24N m, CH2CH2CH2); 0,85-0,93 (6N so, CH3) J=6,0.

Mol. ion (mass by a spectroscope) 573.

Synthesized TNTC used as cationic type surfactants.

While preparing their water naibolshee pressure of the bubbles on the device Rehbinder [see A. Schwartz and J. Perry. Surfactants. - M.: Publishing House. IL, 1953, S. 263]. For comparison, using an aqueous solution of Tetramethylammonium chloride (TMAH) the appropriate concentration. As a control, use the variant with the water that does not contain any additives. Received data (the results of three measurements) were averaged, and the average values were used for further calculations. Surface activity in % of control was determined by the formula

=a-bi/ini·100%,

where a and bi- the value of the control sample and experimental, respectively. The results are summarized in table.

As can be seen from this table that the application of the proposed TND as a cationic surfactant leads to the following results.

If TNTC use it as a cationic type surfactant at a concentration of 0.01 to 10.0 wt.% reduces the value in comparison with control by 40.7-261,5% (19,6-50,5 instead 71,0 n/m), while the use of known Tetramethylammonium chloride reduced this indicator in comparison with control only 28.1-213% (22,6-55,4 instead 71,0 n/m).

In addition, it was found that the acid properties of the proposed SAS compared to the known decreased by 1 is so the application stated TNTC as cationic type surfactants significantly reduce the magnitude of the surface tension of their aqueous solutions, and also to reduce the acidity of the solutions, which is very important from the point of view of subsequent practical application, since the solutions have a high surface activity even at high (1·10-1wt.%) the dilutions and low acidity, which reduces consumption by DV and improves the environment.

2-Chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine structure

as an intermediate in the synthesis of cationic type surfactants.

 

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