DE85490C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

CLASS 12: Chemical processes and apparatus.

Fatentirt in the German Empire from March 2, 1895.

That by W. Heintz (Pogg. Ann. 109,489), Fritsche (Journ. F. Pr. Chemie 19, 34; 20, 267) and from Saarbach (Journ.f.pr.Chemie 21,151) Phenoxyl or described. Naphthoxyacetic acids and their analogues also supply Phenols a new range of aromatic esters (phenoxy acetic acid phenyl ester and its Analogous), which are distinguished on the one hand by the fact that they are odorless and almost or entirely are tasteless and on the other hand split by alkalis with the formation of phenols - properties that make them suitable as antiseptics.

The application of these esters is likely to extend in particular to intestinal disinfection; they have ahead of the already known intestinal disinfectants the following benefits.

The poisonous benzoylguaiacol (Patent No. 55280) on the other hand, they are distinguished by their non-toxicity alone.

Often given, they caused neither local nor general symptoms of poisoning in dogs.

The oily creosote and guaiacol esters of oleic and stearic acid (Patent No. 70483) are in their application did not get beyond the experimental stage and not at all rightly in trade.

In addition, however, these esters of benzoic acid, oleic or stearic acid supply them Cleavage in the intestine in addition to 1 mol. Of the phenol ι mol. Of the inactive acid, while the new derivatives decompose with formation of 2 moles of the phenol from 1 mole of the ester.

Compared to Salol (Patent No. 38973) the Phenoxylessigsäurephenylester on different cleavage products than that, namely the strongly antiseptic phenols compared to those which are only of minor effectiveness as an antiseptic Salicylic acid. Proof that the new esters cannot be dissolved in 1 mole of phenoxy acetic acid and ι Mol. Phenol, but actually split into 2 Mol. Phenol and 1 Mol. Oxyacetic acid and are completely absorbed in the process, has been established by experiments on animals. Symptoms of poisoning have never been observed, while some of the phenoxy 1-acetic acids, z. B. the o-cresoxy acetic acid, cause poisoning with subsequent death.

Compared to the carbonates of the phenols (Patent No. 58129), with which they are the same Have a common effect, the phenoxy acetic acid phenyl ester show the advantage over hydrochloric acid - as it is already evident from the way they are represented - to be constant, while the carbonates of the phenols are attacked by hydrochloric acid. The new esters like the Salole pass the stomach completely undecomposed and only become in the alkaline intestinal canal broken down into their effective components. The direct experiment has also confirmed this. The acidic gastric juice was unable to break down even in a trace.

With regard to the effect on the intestine, it is also noted that a "thickening" of the Chair takes place. Existing diarrhea was eliminated by administration of the esters.

The antiseptic properties of the absorbed substances are shared during excretion through the kidneys also the urine and prevent its decomposition.

(2nd edition, issued on April 6th

Claims (1)

To prepare these new products, the general procedure is that the phenoxyacetic acids are mixed with the phenols in the presence of a suitable condensation agent, such as e.g. B. the chlorides of phosphorus heated. Not only the phenoxyl or phenoxyl mentioned at the outset serve as starting materials. Naphthoxyacetic acid, but its analogues, such as. B. the acids referred to as cresoxacetic acids in patent specification No. 79514, as well as the alkyloxyphenoxacetic acids and analogous derivatives can be used. They can all be prepared from the alkali compounds of the phenols in question, and monochloroacetic acid. It was thus of m-cresol the Oxyessigsäurederivat as a crystallizing from water to needles substance of mp. 102-103 ^0, of p-cresol in the crystallizing leaflets p-Kresoxylessigsäure mp. 154 ^0, from guaiacol OCH ο-methoxyphenoxyacetic acid in the form of 115 to ι 16 ° melting needles obtained. The representation of the alpha esters from these alphoxyl acetic acids - according to a suggestion Bam berger's (Ber. 27, 2583 note.) Alphyl is used to denote the radicals phenyl, tolyl, naphthyl etc. - is explained using the following example: o-methoxyphenoxy acetic acid guaiacyl ester
/ OCH ₃ > - O-CH ₂ -COO- 20 parts of ο-methoxyphenoxyacetic acid, 13.6 Part of guaiacol and 8.4 parts of phosphorus oxychloride are refluxed at 105 Heated to 10 ° in an oil bath until the evolution of hydrochloric acid ceases. The reaction runs according to the equation: OCH ₂ -COOH, OCH OCH OH POCl, = -0-CH ₂ -CO-OC ₆ Hi-OCH ₃ HPO ₃ + ι HCl The reaction mixture is used to liberate phosphoric acid and hydrochloric acid with water leached and the residue recrystallized from alcohol. The ο - methoxyphenoxylessigsäureguajacylester crystallizes in small, colorless needles, melts at 80 °, is insoluble in water, easily soluble in wood spirit, ethyl alcohol, acetone and Benzene, sparingly soluble in ligrom. It is odorless and almost tasteless. His analysis resulted in the following data: for C ₁₆
Ber. C, 66.66 pCt.
H 5.55 - β ^ 5 Found 66.50 pct.
5.80 - Instead of the free acids, their salts and instead of phosphorus oxychloride can also be used Phosphorus pentachloride or other dehydrating agents are used. When replacing the ο-methoxyphenoxyacetic acid through the analogous derivatives or of guaiacol through other phenols one arrives at the other aromatic compounds in an analogous manner Esters of alphoxy acetic acids. Also let yourself take the place of the alphoxy acetic acids use alphoxyl fatty acids derived from the higher homologues of acetic acid. The following are also mentioned as representatives of this new ester group: Phenoxyacetic acid phenyl ester crystallizes from gasoline in long transparent prisms from Mp. 59 to 60 °. Phenoxylessigsäureguajacylester forms whiteness leaflets, mp. 56-57 ^0th O-cresoxyl acetic acid o-cresyl ester crystallizes from aqueous alcohol in long needles with a melting point of 50 to 51 °. ο - Kresoxylessigsäureguajacylester crystallizes from gasoline in needles, mp 81 to 82 ^0th. So far, m - cresoxyl acetic acid - m - cresyl ester has been able to do just as little as m-cresoxy acetic acid guaiacyl ester for crystallization to be brought. ρ -Kresoxylessigsäureguajacylester crystallizes from gasoline in rosette-like grouped prisms of mp. 82-83 ^0th β -Naphtoxylessigsäure - m - cresyl ester crystallizes from gasoline in small needles of mp 91-92 ^0th. Pat ε nt-An SP rüch: Process for the preparation of Alphoxylessigsäurealphylestern and their higher homologues, consisting in using alphoxy acetic acids or their higher homologues Phenols condense in the presence of a dehydrating agent.