CS215910B1 - Method of making the tensids on the base of the monoamine type complexones with hydroxyalcyl group in the molecule - Google Patents

Description

Process for producing surfactants based on monoamine-type complexones with a hydroxyalkyl group in a molecule

The invention relates to, Fröbe based surfactants monoamine complexone type of hydroxyalkyl group per molecule of the formula R N-CH ₂ -C00X presenting new surfactants ch ₂ CH ₂ OH chelating effect.

Presently, 2-amino- (N-2-hydroxyethyl-N-carboxymethyl) fatty acids are known to be carbonaceous to C ^. These compounds were prepared by reacting amines with haloacids in an aqueous alkaline medium: Schwarzenbach, G., Anderegg, G., Schneider, W., Senn, H .: Helv. OHIM. acta 38, 1147 (1955), Jokl V, Majer J., Mazacova M .: Chem. rumors 18, 585 (1964), P. Vieles, M. Pascal, Sequin J .: Compt. rend. 238, 1819 (1954), Djatlova N. M. et al. OHIM. 10, 1131 (1965), Majer J., Riečanská E. Chem. rumors 22-15 (1968).

The preparation of surfactants from the group of 2-amino- (N-2-hydroxyethyl-N-carboxymethyl) fatty acids with a carbon chain longer than C 8 is not possible according to the above. Disadvantages of the prior art are avoided by the process according to the invention. The production method is simple, the product isolation is quick and simple. Reaction yields are 70-80% of theory. High purity substances are obtained. These substances are widely used in practice.

SUMMARY OF THE INVENTION The present invention provides a process for the preparation of surfactants based on monoamine-type complexones with a hydroxyalkyl group in a molecule of the general formula R-N-CHg-COXX

CH ₂ CH ₂ - OH

215 910

215 910 wherein R - _CH3 - / _CH2 / _N-CH-N C00x - 3-17

X - H, Na, K, NH ₄ ⁺ , CH ₃ , C ₉ H ₈ , O ₃ H ₂ O?

characterized in that aa a 10-20% solution of a halo fatty acid in alcohol is condensed at 50 to 75 ° C and 2-aminoethanol in a molar ratio of 1 to 2 to 3 and isolated by simple filtering of 2-amino- / N-2- of high purity hydroxyalkyl / fatty acid and this is condensed in a second step in a 2 to 20% conoentrole in the reaction mixture at 50-100 ° C with the corresponding mono-oleic acid salt in a molar ratio of 1 to 2 to 3 in a hydroalcoholic medium at constant pH 9 to 11 wherein the 2-amino / N-2-hydroxyethyl-N-carboxymethyl / fatty acid voltaate is isolated by acidification with dilute hydrochloric acid in a ratio of 1 to 1 to a pH of 1.5 to 1.6, from which isolation and preparation of the ammonium salt 'neutral! by ammonium hydroxide or ester heating with 15 to 40 times the appropriate anhydrous alcohol while introducing hydrogen chloride gas into the reaction mixture for 30 to 50 hours and isolating the ester by distillation.

EXAMPLE

11.2 g (0.04 mol) of 2-bromolauric acid ea are dissolved in 100 ml of 99.5% ethanol and 6.7 g (0.12 mol) of 2-aminoethanol in 20 ml of ethanol 99.5% are added » the mixture was heated in a water bath at 80 ° C for 4 hours. The 2-amino / N-2-hydroxyatyl / lauric acid obtained, 14 14 29 29 ° C, ^was filtered and washed with ethanol and water, yield 50% of theory.

2.6 g (0.01 mol) of 2-amino (N-2-hydroxyethyl) lauric acid (EtaLa) was neutralized with NaHCO 3 in 65 ml of 75% ethanol. At 80 ° C, 1.8 g (0.015 mol) of sodium monobloroethane in 37 ml of water and 10 ml of 6% NaOH solution are added to the sodium salt of EtaLa to make the reaction mixture pH 9-11. The reaction mixture was heated in a water bath at 80 ° C for 24 hours. After drying, the reaction product can be used directly as a raw material for detergent production. The free acid product is isolated by acidifying the reaction mixture with dilute hydrochloric acid (1: 1) to pH 1.5. After aspiration, the product is washed on the filter with distilled water until neutral and negative reaction for the presence of halogen. The isolated 2-amino / N-2-hydroxyethyl-N-carboxymethyl / lauric acid is purified by reprecipitation. Výtbžok:

79.5% of theory.

Analysis: 014 ^ 29 ^ 3

teoret.t · 64.86, «I - 11.23, S »- 5.40 nájdenéi % C - 64.84, - 11,41, 301 - 5.37 Melting point ° C (subl.) 16 ° ^H 31 ^NO 5 teoret.t % C. 60.54; . 9.84. Stt - 4.41 found % C. 60.75. - 9,96, 5 »- 4.51 Melting point < 86.5 - 87.0 ° C

The isolated 2-amino / N-2-hydroxyethyl-N-carboxymethyl / lauric acid is neutralized with ammonium hydroxide in a molar ratio of 1: 2 to prepare the 2-amino / N-2-hydroxyethyl-N-carboxymethyl / lauric acid.

215 910

Surface activity:

surface tension values y / / S / m. 10-? 7 disodium salt of 2-amino (N-2-hydroxyethyl-N-carboxymethyl) lauric acid as a function of temperature.

Conc.

g / 1 Deň: 22 ° C Deň: 32 ° C 60 ° C 80 ° C 0,006 46.65 52.60 64.31 59,13 10.0 53.92 51.55 48.86 44.90

Example 2

14.5 g (0.04 mol) of kyeella 2-bromostear are dissolved in 100 ml of 99.5% ethanol and 6.7 g (0.12 mol) of 2-aminoethanol in 30 ml of 99.5% ethanol are added. The reaction mixture was heated in a water bath at 80 ° C for 4 hours. The resulting 2-amino / N-2-hydroxyethyl / stearic acid θ204-4ΐ4θ3 ^is filtered off and washed with ethanol and water. 60% yield,

3.4 g (0.01 mol) of 2-amino- [N-2-hydroxyethyl] stearic acid (EtaS) are neutralized and NaHCO3 in 20.0 ml of 75% ethanol. At 80 ° C, 1.8 g (0.015 mol) of sodium monocloroethane in 9.0 ml of water and 5.2 ml of a 12% NaOH solution are added to the sodium salt of EtaS so that the pH of the reaction mixture is 9-. 11. Heat the reaction mixture in a water bath with stirring at 80 ° C for 24 hours. After drying, the reaction product can be used directly as a raw material for the production of detergents. The product in the acid form is isolated by acidifying the reaction mixture with dilute hydrochloric acid (1: 1) to pH 1.5. After suction, the product is washed on the filter with distilled water until the filtrate gives a neutral reaction and no longer responds positively to the presence? halogens. The isolated C22-443®5 2-amino / N-2-hydroxyethyl-N-carboxymethyl / stearic acid is purified by reprecipitation. Yield: 81.8% of theory.

Analysis: C CgoN NCN ^ teoret Theoretical:% C 69 69.92, - 12.03, - 4.07 Found:% C 70 70.62, - 12.31, - 4.00 • Melting point 207.5 - 209 ° C.

^C 22 ^H 43 ^NO 5 theory: $ SC «65.80, - 10.80, S® - 3.48 found: S & - 66.12,% H - 11.00, S® - 3.47

Mp 114-115 ° C.

6.0 g (0.015 mol) of isolated 2-amino / N-2-hydroxyethyl-N-carboxymethyl / stearic acid was heated to reflux with a halocarbon cap with 40-fold amount of anhydrous ethanol while continuously introducing hydrogen chloride gas into the reaction mixture for 50 minutes. hours. After completion of the reaction, will most of the material be distilled off? alcohol, the distillation residue is poured into a sufficient amount of aqueous water and neutralized with NagCO3. The resulting 2-amino (N-2-hydroxyethyl-N-carboxymethyl) stearyl diethyl ester is shaken into ether and isolated by distillation.

Surface activity:

surface tension values $ · 10 “^ 7 2-amino / N-2-hydroxyethyl-N215 disodium salt 910

-carboxymethyl / stearic acid depending on temperature.

A concentrate.

g / 25 ° C 40 ° C 60 ° C 80 ° C

0,006

2.0

52.45 62.26 64.55

43.88 41.65 43.93

60.19

36,08

Claims (1)

A process for the preparation of surfactants based on a monoamine-type complexone with a hydroxyalkyl group in a molecule of the general formula RN-CH-COOX, wherein R CH 2 - / CH ₂ / _n -CH-OOOX CH ₂ CH ₂ N -0H - 3-17 X 1 H, Na, K, NH ₄ ⁺ , CH ³ , CH 2, characterized in that a 10-20% solution of the halo fatty acid in alcohol is condensed at 50 to 75 ° C with 2-aminostanol in a 1 to 1 molar ratio 2-3 is isolated by simply filtering out high purity 2-amino / N-2-hydroxyalkyl / fatty acid and this is condensed in the second step at a concentration of 2 to 20% in the reaction mixture at 50 to 100 ° C b with the appropriate acid salt of mono-ethanol in a molar ratio of 1 to 2 to 3 in an aqueous-alcoholic medium at a constant pH of 9 to 11 wherein the free 2-amino / N-2-hydroxyethyl-N-carboxymethyl / fatty acid is isolated by acidifying with 1 to 1 acidified hydrochloric acid to pH 1.5 to 1.8, from which, after isolation, the ammonium salt is prepared by neutralization with ammonium hydroxide, or an ester with a 15 to 40 fold amount of the appropriate anhydrous alcohol while introducing hydrogen chloride gas into the reaction mixture for 30 to 5 times. 0 hours and isolating the ester by distillation.