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United States Patent Office UNITED STATES PATENT OFFICE. GEORG EICHELBAUM, OF BERLIN, GERMANY, ASSIGNOB TO THE FIRM OF KALLE AND COMPANY, AKTIENGESELLSCHAFT', OF BIEBRICH-ON-THE-RHINE, GERMANY. MANUFACTURE OF ALUMINIUM-iACETATE COMPOUNDS. 1,132,709. speci?cation of Letters Patent. Patented Mar. 23, 1915. No Drawing. Application ?led June 25, 1913. Serial N 0. 775,769. To all whom it may concern : named formation of the compound hexa Be it known that I, Gnone EICHELBAUM, methyleneJtetramin-aluminium-aoetate and 55 doctor of philosophy and chemist, a subject the further combination of this product of the King of Prussia, and residing at with for instance heXamethylene-tetramin Augsburgerstrasse .8, Berlin, W. 50, Ger lactate, compounds are produced, which, many, have invented certain new and useful owing to the fact that they dissociate very 60 Improvements in the Manufacture of Alu readily, combine in an advantageous man minium-Acetate Compounds, of which the ner the ellicacious action both-of acetate of following is a speci?cation. aluminum and of the heXamethylene-te 10 When solutions of aluminium acetate are tramin which is also antiseptic. At the same heated or concentrated, insoluble basic salts time the ?avor is improved and rendered 65 of aluminium are precipitated. Attempts less sharp, which is of importance for in have been made (see German Patents 9790 ternal administration of the products. and 10488) to avoid this precipitation by The process is carried out by causing 15 the addition of certain acids. The residue aluminium acetate, one of the aforemen obtained after evaporation of such solutions tioned compounds which increase the solu 70 to dryness is however no longer an acetate bility of aluminium acetate, and‘ hexa of aluminium as the acetic acid is displaced methylene-tetramin, to react on each other by the acid added and evaporated, because either simultaneously or consecutively. The 20 of its easy volatility, an aluminium salt of hexamethylenetetramin is employed in the acid added (tartaric acid, lactic acid, such a quantity as to neutralize completely 75 etc.,) being left which no, longer possesses the acetic acid contained in the aluminium the special therapeutic action of the origi acetate titrable with sodium-hydroxid nal acetate, and only small traces of the (NaOH), as well as the second acid added. 25 acetic acid remaining. ‘ By titrating aluminium acetate with sodium This invention relates to a process, by hydroxid until phenolphthalein, added as 80 means of which it is possible to obtain com an indicator becomes red, the free acetic pounds which, without the acetate of alu acid as well as about one molecule of the minium being substantially affected, can be acetic acid combined in the al'iminium 30 evaporated to dryness and yet remain solu acetate is neutralized, as is well known. ble. This is elfected by combining the acetic The quantity of hexamethylene~tetramin 85 acid contained in the solution of acetate of used according to the present process should aluminium, whether it be combined with the be sullicient to combine with the acetic acid aluminium or in free state, with hexamethy determined in this way, as well as with the 35 lene-tetramin. In this way a double salt, second acid added, the hexamethylene-te namely hexamethylene-tetramin-aluminium tramin being calculated as a mono-acidic 90 acetate is obtained. The acetic acid is so to base, as above indicated. The solution thus say protected. At the same time there is obtained is then. evaporated to dryness. utilized the. well known property of cer preferably in a vacuum. 40 tain hvdroxyl compounds, such as mannite, Example 1: 1 kg. of ollicinal aluminium glycerin, or oxy-acids, such as citric acid, acetate solution (containing 0.085 gr. acetic 95 tartaric acid or their salts, of maintaining acid in l cbc. cm.) is mixed at the ordinary in solution compounds of aluminium (as temperature with 50 gr. citric acid and well as of iron). It is advisable in practice 300—310 gr. hexa-methylene-tetramin and 45 not to use the said oxy compounds in a free left standing for some time. The solution state, but combined or mixed with an equiv thus obtained is then evaporated to dryness 100 alent quantity of hexamethylene-tetramin. in a vacuum at about 60-70". IThe salt ob Hexamethylene~tetramin is a monoacidic tained in this manner, is a white crystalline base, the molee?lar weight of which is 140. mass of sweet taste, which can be easily re 60 Equivalent quantities of hexamethylene duced to powder. The well known harsh, tetramin and citric acid for instance are tart taste of soluble aluminium compounds 105 therefore 140 parts of the former to is no longer perceptible. The preparation 210/3270 parts of the latter (citric acid is easily soluble in water. The solution does being a tribasic acid). Owing to the above not coagulate when boiled, and does not 2 1,132,709 precipitate any. alumina. The salt is almost compounds of aluminium acetate which insoluble in ether. \Varm dilute alcohol dis comprises treating aluminium acetate solu 65 solves it almost completely, while it does tions with hexamethylene- tetramin and not completely dissolve in absolute alcohol. evaporating to dryness. It is-alsolargely soluble in benzol. The salt 3. The process of producing water soluble dissolves completely in warm diluted hydro compounds of aluminium acetate which chloric acid (5%) also in acetic vacid or comprises treating the same with hexa— 70 glacial acetic acid, and also in diluted sul methylene-tetramin in the presence of com furic acid but in the latter case a slight pounds increasing the solubility of alumin 10 opalescence is noticeable, (due to calcium ium compounds. ‘ acetate of the acetate of alumina). Dilute 4. The process of producing water soluble soda lye also dissolves it, and also in this compounds of aluminium acetate which 75 case only a little lime is left as a sediment comprises treating aluminium acetate solu at the bottom. Acetone dissolves it only tions with hexamethylene- tetramin and 15 partially. evaporating to dryness in the presence of Example2: 1 kg. aluminium acetate (com compounds increasing the solubility of pare Example 1) is mixed with 50 gr. tar- I aluminium compounds. ' 80 taric acid and about 285 gr. hexa-methylene 5. The» process of producing water soluble tetramin, and then treated in the same way compounds of‘ aluminium acetate which 20 as in the foregoing example. In this way comprises treating solutions of aluminium solid white transparent crystals are ob acetate with a solution of hexamethylene tained, the properties of which are the same tetramin, and evaporating to dryness. 85 as those of the salts obtained in the Ex 6. The process of producing water soluble ample 1. compounds of aluminium acetate which 25 Example 3: 1 kg. aluminium acetate (see comprises treating solutions of aluminium Example 1) is mixed with 50 gr. lactic acid acetate with a solution of hexam'ethylene and about 265 gr. heXa-methylene-tetramin tetramin, and evaporating. to dryness in the 90 and treated as stated in Example 1. This presence of compounds increasing the solu gives a white mass of very thick pasty con bility of aluminium compounds. 30 sistency which can be readily pressed in 7. The process of producing water soluble tubes. The properties correspondotherwise compounds of aluminium acetate which com to those of the product described in the Ex prises treatingsolutions of aluminium ace 95 ample 1. tate with a solution of hexamethylene-te In place of the solid heXamethylene-te-v tramin, and evaporating to dryness in a. 35 tramin, formaldehyde and ammonia can be vaczuum and at a temperature of about 60 used, these reagents combining to form to 0°. heXamethylene-tetramin.iu solution, as is 8. The process of producing water soluble well known. Accordingly the dry hexa compounds of aluminium acetate which methylene-tetramin and the formaldehyde comprises treating solutions of aluminium ammonia solutions which form hexamethyl acetate with a solution of hexamethylene ene-tetramin are equivalents for purposes of tetramin, and evaporating to dryness 1n the the present invention. The use of such presence of hydroxyl compounds increasing 105 formaldehyde-ammonia solutions is illus the solubility of aluminium compounds. trated by the following example.v 9. A new product comprising a water 45 Example 4: 1 kg. of solution of o?icinal soluble compound of aluminium acetate and aluminium acetate (compare Example 1) hexamethylene-tetramin. is mixed with 50 gr. citric acid, and the 10. A new product comprising a water 110 liquid evaporated after adding a mixture soluble compound of aluminium acetate and of formalin and ammonia in quantities cal heXamethylene-tetr'amin combined with a 50 culated for 300 gr. of hexa-methylene-te compound increasing the solubility of ' tramin. This mixture of formalin and aluminium compounds. ammonia‘ must be left standing 24 hours be 11. A new product comprising a water 115 fore use, until, after a slight heating, the soluble compound of aluminium acetate and ammonia smell has disappeared. The prop heXamethylene-tetramin combined with a 55 erties of the end product obtained in that hydroxyl compound increasing the solu- manner, correspond to those described in bility of aluminium compounds. Example 1. In testimony whereof I have signed my 120 I claim : name to this speci?cation in the presence of 1. Theprocess of producing water soluble two subscribing witnesses. 60 compounds of aluminium acetate which GEORG EICHELBAUM. comprises treating the latter with hexa Witnesses: meth' 1lene~tetramin. ' HENRY HAsPER, 2. ‘he process of producing water soluble ~WoLmsauln HAUPT. .
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