CS271148B1 - Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation - Google Patents

Abstract

The solution concerns dithioderivates of carbamoyl-4-butane sulfone acid and their derivates of the general formula R-(CH2)4S03<->Me<+>, where Me is natrium, potassium or hydrogen, and R is residuum of the general formula IIa or IIb, where R<1> is o-disubstituted aromatic nucleus with the number of carbon atoms 6 to 20 or heteroaromatic nucleus with the number of carbon atoms 3 to 10, sulphur, nitrogen or oxygen containing possibly halo-, nitro-, sulfo-, hydroxy-, amino- and/or mercapto groups or alkylene. R<2> and R<3> are the same or different alkyl residua with the number of carbon atoms 1 to 6 or hydrogen. 1, 4- butane sulfone in water and/or aliphatic alcohol affects dithioderivates. These new substances are used as a polishing mixture in copper baths and their advantage is the production of non-carcinogenic 1, 4- butane sulfone.<IMAGE>

Description

The present invention relates to a carbamoyl-4-butanesulfonic acid dithioderivative and a derivative thereof, and to a process for their preparation. New compounds of formula I have been found

R - (CH ₂ ) 2 SO 4 Me * (I), wherein Me is sodium, potassium or hydrogen and R is a radical of formula (IIa) or (IIb)

wherein R ¹ is an o-disubstituted aromatic nucleus having a carbon number of 6 to 20 or a heteroaromatic nucleus having a carbon number of 2 to 10, sulfur, nitrogen or oxygen, optionally containing halo-, sulfo-, hydroxy-, amino- and / or mercapto groups or an alkylene of from 3 to 10 carbon atoms of 2 to 20, R, R are the same or different alkyl radicals of 1 to 6 carbon atoms or hydrogen.

These substances have not been described in the literature yet. Only similar derivatives are known

4-hydroxypropanesulfonic acids whose synthesis requires the use of a highly carcinogenic one

1.3-propanesulfone, which is technically unacceptable. It has therefore been sought whether derivatives obtained from non-cancerogenic 1,4-butanesulfone have similar effects (polishing additive for acidic galvanic copper baths).

The process for the preparation of carbamoyl-4-butanesulfonic acid dithioderivatives and their derivatives according to the invention consists in treating dithioderivatives of the formula R- or RR, where R is a radical of the formula IIa or IIb in the presence of 1,4-butanesulfone base in water and / or an aliphatic alcohol having a carbon number of 1 to 6 at a temperature of 10 to 120 ° C for 0.05 to 5 hours.

These substances are solid, white compounds of amorphous character which can only be crystallized very poorly from ethanol. The acid cannot be isolated in its pure state, the salts can be isolated from the solution after evaporation and determined, for example, by infrared or NMR spectra. They are undetectable and not characterized by conventional methods.

Tetraalkylthiuram disulfide, dialkyldithiocarbamic acid or salts thereof may be used as starting materials, in the case of dialkyldithiocarbamic acid by reaction in an oxidizing medium, tetraalkylthiuram disulfide may be formed intermittently and react immediately. The dithiocarbamic acid derivative is also 2-mercaptobenzthiazole, which can react analogously. The reaction takes place in the presence of hydroxyl ions in an aqueous or aqueous-alcoholic medium. The product can either be isolated by careful evaporation or even directly used as a reaction solution as an additive to the galvanic copper acid bath.

EXAMPLE 1 1 g of tetramethylthiuram disulfide was mixed with 100 ml of ethanol, 2 l of water and sodium hydroxide and stirred at 40 DEG C. for 3 hours. Then was added successively 82 g _in

1,4-butanesulfone and heated to 100 ° C for one hour. The resulting sodium N, N-dimethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.

Example 2

100 g of 2-mercaptobenzthiazole are stirred with 1.5 l of water, 25 g of sodium hydroxide and stirred at 45 DEG C. for 2 hours. Subsequently, 82 g of 1,4-butanesulfone are added successively and heated to 90 ° C for 30 minutes. The resulting solution of sodium 2-mercaptobenzthiazolyl-4-butanesulfonate was evaporated to dryness in vacuo at 50 ° C and the residue was stirred with a little cold ethanol. After drying at 40 ° C, a white, non-determinable powder was obtained.

Example 3 · g Ν, Ν, Ν’Ν-tetraethylthioramide disulfide is mixed with 1000 ml ethanol and 30 g sodium hydroxide and stirred for 2.5 hours at 50 ° C. Then add 2 liters of water,

CS 271 148 B1 g of 1,4-butanesulfone and heated at 95 ° C for 2 hours. The resulting sodium N, N-diethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.

Example 4 Potassium Ν, Ν-diethyldithiocarbaminate (4 g) was mixed with 1.5 L of water and stirred at 25 ° C for half an hour. 83 g of 1,4-butanesulfone are then added and heated to 90 ° C with stirring for 1 hour. The resulting potassium N, N-diethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.

Claims (2)

Dithioderivatives of carbamoyl-4-butanesulfonic acid and their derivatives of the general formula I R- (CH ₂ ) ₄ SO Me ⁺ (I), wherein Me is sodium, potassium or hydrogen and R is a residue of the general formula IIa or IIb wherein R ¹ is o-disubstituted aromatic nucleus having a carbon number of 6 to 20 or a heteroaromatic nucleus having a carbon number of 3 to 10, sulfur, nitrogen or oxygen, optionally containing halo-, nitro-, sulfo-, hydroxy- and / or mercapto groups or alkylene The number of carbon atoms 2 to 20, R, R is the same or different alkyl radicals having a carbon number of 1 to 6 or hydrogen. A process for the preparation of carbamoyl-4-butanesulfonic acid dithioderivatives or derivatives thereof, characterized in that dithioderivatives of the general formula R or RR, where R is a radical of the general formula IIa or IIb, are treated with 1,4-butanone sulfone in water and / or an aliphatic alcohol having a carbon number of 1 to 6 at a temperature of 10 to 120 ° C.