DE639625C - Process for the production of water-soluble, higher molecular weight, unsaturated fatty alcohol sulfuric acid esters - Google Patents

Description

GERMAN EMPIRE

ISSUED ON ΙΟ. DECEMBER 1936

. REICH PATENT OFFICE

PATENT LETTERING

CLASS 12o GROUP 2302

Böhme Fettchemie-Gesellschaft m. B. H. in Chemnitz *)

Fatty alcohol sulfuric acid esters

Patented in the German Empire on May 28, 1935

The usual sulfonation of unsaturated fatty alcohols using sulfuric acid, Oleum, chlorosulfonic acid and the like as sulfonating agents generally add Products in which the sulfuric acid residue is partly to the hydroxyl group, partly to the double bond occurs. The quantitative ratio of those with the hydroxyl group or the double bond reacting sulfonating agent depends on the reaction temperature, by lowering the temperature predominantly the double bond, with a higher one the hydroxyl group reacts. Through certain additives to the sulfonating agents, lind in particular of Ethyl ether and tertiary bases, especially pyridine, have already been used with some Success tries to direct the reaction so that, the double bond to the larger Part remains free and the OH group is almost completely esterified by sulfuric acid will. Apart from the fact that the success here remains very incomplete, these older processes also have the disadvantages that the additives used are sometimes extraordinary are flammable, like the ethyl ether, partly with a strong odor nuisance bring, like pyridine, in any case a very extraordinary increase in price and complication of the sulfonation process due to the solvents required and bring with them their recovery. So up to now there has not been a satisfactory one Process for the production of unsaturated fatty alcohol sulfonates, which as a result of certain Properties, especially the lower freezing point, from consumers may be requested for specific purposes.

It has now been found that sulfonation products of unsaturated character can be obtained easily and simply from unsaturated, higher molecular weight fatty alcohols, by using freshly prepared mixtures or mixtures that have been stored for a long time as a sulfonating agent of chlorosulfonic acid or fluorosulfonic acid with common salt or another alkali halide used. Bringing these components together evolves. Hydrogen halide forming a pulpy mass that may be the monosodium salt of Pyrosulfuric acid monochloride

Cl-SO ₂ -O-SO ₃ -ONa

contains. If you bring an unsaturated fatty alcohol, such as. B-. · Oleyl alcohol. or Octadeoen-9-diol-i, 12, zur Reaction, sulfonates are obtained in which the hydroxyl group is practically complete sulfonated, the double bond, however, has remained practically completely free and the as a wetting and cleaning agent and as a di-

*) The patent seeker stated as the inventor:

Dr. Albert Metzger in Chemnitz.

dispersing agents, especially in cosmetic preparations, ointments, creams, etc., as well as are valuable for dispersing essential oils in water and similar purposes ..:, The method can for example follow £ jii are carried out in such a way: ..-: '«.;

Example ι

250 parts by weight of oleyl alcohol are allowed to act on 275 parts by weight of a sulfonating agent prepared from molecular amounts of chlorosulfonic acid and pure common salt by exposure for 24 hours. It ensures that the reaction temperature does not exceed 20 ⁰ increases. After solubility in water has been achieved, the acidic sulfonate is diluted with 700 parts by weight of water and neutralized with sodium hydroxide solution of 36% by weight. A paste with about 15% fatty alcohol content is obtained in this way. This is stirred with about 200 to 250 parts by weight of saline to stand at about 40 to 50 ⁰ until the salt water is separated. The paste that settles here has a fatty alcohol content of around 50% and represents a marketable product without further purification. If desired, the product can also be subjected to bleaching, expediently with sodium chloride solution, which is preferably done after the paste has been salted out. The sulphonate is thereby significantly lightened, and the lime resistance also increases significantly.

At least the same weight amounts of sulfonating agent, calculated on the fatty alcohols, are used for the sulfonation. An excess of sulfonating agent can be useful. The reaction temperature is best maintained between about 10 and _(5o °; at lower temperatures, the reaction proceeds sluggishly, at higher temperatures tends to occur a discoloration of the final product.

Example 2

150 parts by weight of potassium chloride are reacted with 240 parts by weight of chlorosulfonic acid and, after the hydrogen chloride has escaped, the mixture is left with the exclusion of moisture. 6 days. 100 parts by weight of octadeo-9-diol-i, 12 are then added to 200 parts by weight of the sulfonating agent obtained in this way, the mixture is stirred well and left to stand until solubility in water has occurred. Then it is diluted with 400 parts by weight of water and neutralized with sodium hydroxide solution of 36 percent by weight. Initially, the entire reaction mixture solidifies to form a gelatinous mass which, however, as described in Example 1, can be broken down by salting out. By treatment with chlorine- ;; _; The brownish colored sulfonate can be lightened in the eyes.

; * 'v * ij * The iodine number of the fatty alcohol after the ab- • Cleavage from the sulfonate by means of acid in the investigation of the Turkish red oils and the like Oleyl alcohol about 70 to 80, in the case of the conventional method using sulfuric acid or Chlorosulfonic acid obtained from oleyl alcohol products, however, only 20 to 40. Da the theoretical iodine number of oleyl alcohol is 95, according to the new method a product is achieved in which the double bond has remained almost completely unaffected and that accordingly has extremely valuable technical properties.

In an analogous manner, unsaturated ones other than those described in the examples can be used Fatty alcohols, such as. B. undecylene alcohol or erucyl alcohol, in unsaturated fatty alcohol sulfonates be transferred.

The products can be very beneficial for washing and cleaning, especially at low temperatures, for dispersing water-insoluble and sparingly soluble Substances, as wetting agents in hard water, serve briefly everywhere where capillary active Means are needed and it has a low freezing point, good dispersibility and great resistance to lime and magnesia salts.

Claims (2)

Patent claims: ι. Process for the preparation of water-soluble higher molecular weight unsaturated fatty alcohol sulfuric acid esters by treatment of unsaturated fatty alcohols with sulfonating agents, characterized in that that one unsaturated higher molecular fatty alcohols with action products, which in the implementation of Alkali halides, especially of common salt, with halosulfonic acids in approximately molecular weight Amounts obtained are esterified and at ordinary or moderately elevated temperature "Ίηΐΐ sulfuric acid then optionally neutralizing and salting out the ester product. 2. The method according to claim 1, characterized in that. the products Subsequently subjected to bleaching, in particular by the action of chlorine lye will.