DE1493662A1 - Process for the production of condensation products based on 2-oxyaethanesulfonic acid - Google Patents

Description

FARBWERKE HOECHSI AG. Gendorf, April 28, 1964

formerly Master Lucius & Brüning 'PA 1 I Gd 1350

H93662

Description ■ zur

Patent registration

" Process for the production of condensation products based on 2 ~ oxyethanesulfonic acid "

Additional registration to ....... (P 41 284 IVb / i2 q),

Subject of the main patent. ... ... (F 41 284 IVb / 12 q) is a Process for the preparation of condensation products based on 2-oxyethanesulphonic acid by condensing salts of 2-oxyethanesulphonic acid with carboxamides of the general formula

I. R.CO.NH

at temperatures of 160 to 250 °, preferably 190 to 220 ° C, in Presence of catalytically active amounts of a hydroxide or Alcoholates of an alkali or alkaline earth metal with removal of the water that forms from the reaction mixture.

In formula I, R denotes an aliphatic saturated or unsaturated _f, preferably straight-chain ©, but optionally also a branched group with 6 to 22 carbon atoms or a cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic radical; R ¹ denotes an alkyl, phenyl or group condensed from aromatic rings. Both R and R ^f can in turn be substituted by halogen atoms, hydroxyl, nitro or alkyl groups. For further details of the process, reference is made to the main patent.

The subject of the present invention is a further training of the procedure of the main patent a. It is characterized by that the carboxamides of formula I by carboxamides of below formula

II. R.CO.NH ₂

be replaced. In the carboxamides of the formula II, R has the same meaning as in the formula I, while in the place of the

BATH 9 0 980 9/057 6

Substituents R ^{1 has entered} the second hydrogen atom of the amide group.

The products of the new process are carboxylic acid taurides, e.g. fatty acid taurides, which up to now have only been carried out analogously to methyl taurides Condensation of fatty acid chlorides with ifa-2-aminoethane sulfonate were manufactured. Because the taurine required for this reaction by reacting Natrirai-2-oxyäthansulfonat with a large Surplus of ammonia "obtained at high temperatures and pressures must be, is the "previous manufacturing process of the · Carboxylic acid taurides are very expensive and, moreover, only deliver impure Reaction products.

The method of the invention "is based on the surprising finding that also the fatty acid amides that are not subscribed to nitrogen with sodium 2-oxyäthansulfonat in the presence of a alkaline catalyst in the temperature range from 160 to 250 ° C, preferably 190 to 220 ° 0, with elimination of water smoothly to fatty acid taurides let condense. This is surprising since the carboxamides are otherwise easy to hydrolyze excel, and one should have expected that they would take in the presence of alkali and water at the high reaction temperature Splitting off ammonia to the sodium salt of the carboxylic acid would be saponified, before the intended condensation with the Oxyäthensulfonat ends .. could run.

The amount of alkali required for the reaction in the form of hydroxides or alcoholates of alkali or alkaline earth metals is in the same size range as in the process of the main patent, namely between 0.1 and ⁵⁰ A, calculated on the weight of the acid amide. The amide contains something Free acid, the amount of alkali must be increased accordingly, because only free caustic alkali acts as a catalyst. Like that of the main patent, the reaction proceeds relatively quickly, in contrast to the condensation of alcohols with oxyethane sulfonates known from US Pat. No. 2,525,677. The reaction of the method of the invention is according to the equation

H
R. CO. NH + HO. CH ₂ CH ₂ . S0 ~ Me - R.C0.SH.CH ₂ CH ₂ , SO * Me + HgO whereby the water that is split off is separated from the reaction mixture.

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909809/0576

must be performed. It is advantageous to use one during the implementation To pass inert gas such as nitrogen or carbon dioxide onto or through the reaction mixture. By reducing the pressure during During the reaction or towards the end of the reaction, the removal of the volatile substances by distillation can be accelerated.

Simple operations are sufficient to carry out the method, since Normal pressure is carried out in a weakly alkaline melt in a stream of inert gas.

The carboxamides used as starting materials are prepared in a known manner by reacting ammonia with the carboxylic acids or their esters easily and cheaply produced. If appropriate, a technical carboxamide can also be used as the starting material serve, which a certain proportion of substituted on nitrogen Amides, for example Metfcylamid contains. Sodium 2-oxyethanesulfinate becomes simple and on a large scale generated by reacting ethylene oxide with sodium bisulfite.

For the purposes of the invention, the amides of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid, linolenic acid, ricinoleic acid, alkylbenzoic acids, alkylnaphthoic acids, monauric acids, and for example technical acidic acids are mentioned as carboxamides for the purposes of the invention are obtained, are also suitable technical acid amides which ay.e by reaction with ammonia to natural fats or oils | from the natural products tallow, castor oil, olive oil, peanut oil, coconut oil, soybean oil, cottonseed oil, linseed oil, tall oil, Fisehöl, naphthenic acids, Harzsäurej directly, that is, without isolation from the glyeerides. The thermally unstable, highly branched synthetic carboxylic acids are less suitable for the process of the invention.

An expedient embodiment of the method of the invention consists in that the sarboxylic acid oxide is heated in the molten state together unit the troekeaea Oxyäthansälss and the catalyst serving alkali compound in approximately ratio with stirring and introduction of an inert gas to a temperature iron 19X2 to 210 ° ϋ . At about 195 ° C., water of condensation is split off and the reaction takes place

U93662

relatively quickly, so that they are within 30 to 60 minutes has ended in the main. The reaction mixture becomes increasingly homogeneous and viscous and in balance see a bright viscous soap glue. The reaction is ended at 200 to 220 ° C. with continued stirring and, if appropriate, at reduced pressure until no more water passes over. Depending on the intensity of stirring, the viscosity of the melt and the one used Amount of catalyst, the reaction times range between about 1 and 4 hours.

Daa process delivers in good yield in terms of smell and color flawless products. At the reaction temperature they are easily stirrable to kneadable paste-like masses. Your viscosity is up generally higher than that of the main patent tea products. at The products of the process are plastically deformable at room temperature to pulverizable-brittle masses of yellowish to white shade, which can be found in water in the cold or in Clearly dissolve with gentle warming. In terms of their surface-active properties, they correspond to the previously known products Verijindungsklasse.

An advancement of the method of the invention lies in that the products are free of common salt and by-products with which they are produced according to the previous manufacturing processes were inevitably afflicted.

The products of the process are particularly suitable as detergents, wetting agents, emulsifiers, dispersants, flotation agents, oil splitters and for other possible uses of surface-active substances. ^:

The following examples illustrate embodiments the invention.

909809/057 6 ^BAD original

"H93662

example 1

195 g of lauric acid amide (acid number 26) are melted in a 1 liter round-bottomed flask equipped with a stirrer, thermometer, gas inlet tube and descending condenser, and 150 g of dry, powdered material are added Na-2-oxyethane sulfonate and 7 g caustic soda powder - of which 3.7 g for Neutralize - to be consumed, introduces dry nitrogen into the mass while stirring and slowly heats up 190 to 200 ° C. After about 15 minutes the elimination of water begins} the temperature is increased to 210 °, whereby the elimination of water becomes stronger and the mass becomes more and more homogeneous. The temperature is now increased to 220 ° C. and stirring is continued for about 3 hours until the reaction mixture is a uniform, some foamy melt is present, which dissolves clearly in water with strong foaming. The aqueous solution reacts weakly alkaline and remains clear even after acidification.

Example 2

In the apparatus and according to the method of Example 1, 224 g of palm kernel fatty acid amide (acid number 11) and 150 g of Na-2-oxyethane sulfonate are added in the presence of 5.8 g of powdered caustic soda, of which 1.8 g serve to neutralize and obtain a very brittle, easily pulverizable cream-colored mass, which dissolves in water easily and clearly solves

example "}

According to the method of Example 1, 2Θ1 g of a technical Soya oil fatty acid amide, which is obtained by post-treatment of a soya oil fatty acid amide, acid number 44, with methylamine up to acid number 8 and consists of 220 g of soybean oil fatty acid amide, 50 g of soybean oil fatty acid methylamide and 11g of soybean oil fatty acid, with 150 g Na-2-Oxyäthaneulfonat in the presence of 5.5 g of powdered caustic soda, of which 1.5 g of sub leutralieieren are consumed to. Since the reaction product is a homogeneous, semi-solid yellow mass, which dissolves clearly in water and clears even after acidification remains soluble.

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909809/0 $ 76

Claims (1)

Process for the production of condensation products Based on 2-oxyethanesulfonic acid according to patent (F 41 284 IVb / 12 q) _f characterized in that, instead of the nitrogen-substituted carboxamides, those of the general formula R.CO.NHp are used. 909809/0576