DE124408C - - Google Patents
Info
- Publication number
- DE124408C DE124408C DENDAT124408D DE124408DA DE124408C DE 124408 C DE124408 C DE 124408C DE NDAT124408 D DENDAT124408 D DE NDAT124408D DE 124408D A DE124408D A DE 124408DA DE 124408 C DE124408 C DE 124408C
- Authority
- DE
- Germany
- Prior art keywords
- pyrogallol
- acetic anhydride
- triacetate
- parts
- mineral acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 229940079877 Pyrogallol Drugs 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- AQGLTPNHAAVOKN-UHFFFAOYSA-N (2,3-diacetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(OC(C)=O)=C1OC(C)=O AQGLTPNHAAVOKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 3
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 229960002217 Eugenol Drugs 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- XIROXSOOOAZHLL-UHFFFAOYSA-N Gallacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1O XIROXSOOOAZHLL-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-M triacetate(1-) Chemical compound CC(=O)CC(=O)CC([O-])=O ILJSQTXMGCGYMG-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- -1 zinc chloride Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVr 124408 -KLASSE \2q. - JVr 124408 - CLASS \ 2q.
Patentirt im Deutschen Reiche vom ig. August 1899 ab.Patented in the German Empire by ig. August 1899.
Während die Acetylirung des Pyrogallols mittels Acetylchlorid nur unter gewissen Vorsichtsmafsregeln in einfachem Sinne verläuft, da durch die freiwerdende Salzsäure allzuleicht secundäre Reactionen hervorgerufen werden, und die Anwendung von Essigsäureanhydrid nur bei höherer Temperatur zum Ziele führt, erfolgt die Acetylirung des Pyrogallols durch Essigsäureanhydrid in glattester Weise und ohne Wärmezufuhr in analoger Weise wie die in der Patentschrift 10358.1 beschriebene Acetylirung des Eugenols bei Gegenwart einer Mineralsäure, wobei ein durchaus einheitliches Product in vorzüglicher Reinheit, nämlich das Pyrogalloltriacetat, entsteht. Dieser Verlauf der Reaction ist um so bemerkenswerther, als nach den Angaben der Patentschrift 105240 bei Anwesenheit von Mineralsäure, ja sogar bei Gegenwart eines Salzes, wie Chlorzink, neben schmierigen Producten stets beträchtlicheMengen Gallacetophenon oder Derivate desselben sich bilden. Die Wirkung des Essigsäureanhydrids auf Pyrogallol bei Gegenwart einer Mineralsäure ist demnach je nach der Temperatur eine verschiedenartige. While the acetylation of pyrogallol with acetyl chloride only proceeds in a simple sense under certain precautionary measures, since secondary reactions are all too easily caused by the hydrochloric acid released, and the use of acetic anhydride only leads to the goal at higher temperatures, the pyrogallol is acetylated by acetic anhydride in the most smooth manner and without Supply of heat in a manner analogous to the acetylation described in patent specification 10358.1 of eugenol in the presence of a mineral acid, with a thoroughly uniform product in excellent purity, namely pyrogallol triacetate, is produced. This course of the Reaction is all the more remarkable as according to the data in patent specification 105240 Presence of mineral acid, even in the presence of a salt such as zinc chloride, alongside greasy products always contain considerable amounts of gallacetophenone or derivatives thereof form. The effect of acetic anhydride on pyrogallol in the presence of a mineral acid is therefore different depending on the temperature.
i. 200 Theile Pyrogallol werden mit 500 Theilen Essigsäureanhydrid und 1 Theil concentrirter Schwefelsäure zusammengebracht, wobei unter lebhafter Wärmeentwickelung Lösung stattfindet. Innerhalb kurzer Zeit beginnt die Abscheidung des Triacetates in Krystallen. Nach vollzogener Einwirkung wird das Reactionsgemenge mit Wasser versetzt. Nach Entfernung der Lauge und Auswaschen mit Wasser hinterbleibt das Pyrogallolacetat als weifses Krystallmehl.i. 200 parts of pyrogallol are made with 500 parts of acetic anhydride and 1 part concentrated sulfuric acid, with vigorous development of heat Solution takes place. The triacetate begins to separate in a short time Crystals. After the reaction has taken effect, water is added to the reaction mixture. After removing the alkali and washing it out with water, the pyrogallol acetate remains as white crystal flour.
2. Zu der Mischung von 80 Theilen Pyrogallol und 200 Theilen Essigsäureanhydrid wird ι Theil wässerige Salzsäure zugefügt. Unter beträchtlicher Erwärmung geht das Pyrogallol in Lösung. Nach mehrstündigem Stehen krystallisirt das Pyrogalloltriacetat aus und wird nach beendeter Abscheidung in bekannter Weise isolirt.2. To the mixture of 80 parts pyrogallol and 200 parts acetic anhydride is added Partly aqueous hydrochloric acid was added. The pyrogallol goes under considerable warming in solution. After standing for several hours, the pyrogallol triacetate crystallizes out and becomes isolated in a known manner after the deposition has ended.
Der gleiche. Vorgang vollzieht sich, wenn an Stelle der Salzsäure als Condensationsmittel wässerige Phosphorsäure verwendet wird.The same. The process takes place when hydrochloric acid is used as a condensation agent aqueous phosphoric acid is used.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE124408C true DE124408C (en) |
Family
ID=393204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT124408D Active DE124408C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE124408C (en) |
-
0
- DE DENDAT124408D patent/DE124408C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE124408C (en) | ||
| DE148875C (en) | ||
| DE49060C (en) | Process for the preparation of meta-amidophenols | |
| DE50534C (en) | Process for the isolation of a dye of the indulin series | |
| DE116922C (en) | ||
| DE58955C (en) | Process for the preparation of tetraalkyldiamidodioxydiphenylmethanes | |
| DE200601C (en) | ||
| DE102894C (en) | ||
| DE200115C (en) | ||
| DE515540C (en) | Process for the preparation of diacidyl derivatives of meta-xylene | |
| DE40747C (en) | Process for the preparation of ketonic acid esters and ketoketones by the action of two acid esters on one another or of acid esters on ketones in the presence of sodium alkoxides | |
| DE120016C (en) | ||
| DE58614C (en) | A method for preparing an amidonaphthoxyacetic acid and a sulfonic acid thereof | |
| DE630021C (en) | Process for the preparation of 4,5-alkyl-substituted 2-aminodiaryl ketones | |
| DE514505C (en) | Process for the preparation of 1-methyl-5-chlorobenzene-2-carboxamide-3-thioglycolic acid | |
| DE73860C (en) | Process for the preparation of nitrooxyanthraquinone | |
| DE141893C (en) | ||
| DE890647C (en) | Process for the production of Ni-acyherren Aminoarylsulfonamiden | |
| DE273809C (en) | ||
| DE121686C (en) | ||
| DE501083C (en) | Process for the preparation of benzanthrone derivatives | |
| DE112175C (en) | ||
| DE189179C (en) | ||
| DE200145C (en) | ||
| DE267523C (en) |