DE268621C - - Google Patents
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- Publication number
- DE268621C DE268621C DENDAT268621D DE268621DA DE268621C DE 268621 C DE268621 C DE 268621C DE NDAT268621 D DENDAT268621 D DE NDAT268621D DE 268621D A DE268621D A DE 268621DA DE 268621 C DE268621 C DE 268621C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- alcohol
- carboxylic acids
- reaction
- mixture
- 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.)
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- -1 aromatic carboxylic acids Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 240000002268 Citrus limon Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229940103091 Potassium Benzoate Drugs 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M Potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 239000004300 potassium benzoate Substances 0.000 description 2
- 235000010235 potassium benzoate Nutrition 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- MLLAPOCBLWUFAP-UHFFFAOYSA-N 3-methylbutyl benzoate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1 MLLAPOCBLWUFAP-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N Rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drugs Quinolines Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Darstellung von Estern aromatischerThe appearance of esters more aromatic
Carbonsäuren durch Umsetzung der Salze aromatischer Carbonsäuren mit Halogeniden von Alkoholen ist in vielen Fällen mit Schwierigkeiten verknüpft.Carboxylic acids by reacting the salts of aromatic carboxylic acids with halides alcohol is associated with difficulties in many cases.
Es hat sich nun gezeigt, daß die Umsetzung carbonsaurer Salze mit Alkoholhalogeniden meist glatter verläuft, wenn man sie in Gegenwart organischer Basen ausführt. Als geeigneteIt has now been shown that the reaction of carboxylic acid salts with alcohol halides usually runs smoother when done in the presence of organic bases. As suitable
ίο Basen seien beispielsweise genannt Trialkylamine, Pyridin, Chinoline Piperidin, ferner Dimethylanilin, Anilin selbst usw. Es genügen schon sehr kleine Zusätze dieser Basen für die beschriebene Wirkung. Statt der Salze der Carbonsäuren können auch die freien Carbonsäuren oder innere Salze solcher (wie sie z. B. in manchen Phtaleinfarbstoffbasen vorliegen) unter Zusatz von basischen Mitteln benutzt werden.ίο Bases are, for example, trialkylamines, Pyridine, quinolines, piperidine, also dimethylaniline, Aniline itself, etc. Even very small additions of these bases are sufficient for the described effect. Instead of the salts The carboxylic acids can also be the free carboxylic acids or internal salts of such (such as she z. B. in some phthalein dye bases) with the addition of basic agents to be used.
Die so erhaltenen Ester können zur Darstellung von Farbstoffen und pharmazeutischen Präparaten verwendet werden.The esters thus obtained can be used for the preparation of dyes and pharmaceuticals Preparations are used.
N Beispiel I. N Example I.
100 Teile fein gepulvertes Kaliumbenzoat werden mit 120 Teilen Benzylchlorid und ι Teil Triäthylamin 30 Minuten auf 95 bis 100° erwärmt. Aus der durch fein verteiltes Chlorkalium getrübten Flüssigkeit kann das das Benzylbenzoat durch Aufnehmen in Äther, • Filtrieren und fraktionierte Destillation leicht gewonnen werden. Es siedet bei 316 bis 317 ° (vgl. Kohn und Trantom [Soc. 75, 1155]).100 parts of finely powdered potassium benzoate are mixed with 120 parts of benzyl chloride and ι part of triethylamine heated to 95 to 100 ° for 30 minutes. From the finely divided Potassium chlorinated liquid can destroy the benzyl benzoate by being absorbed in ether, • Filtration and fractional distillation are easily obtained. It boils at 316 to 317 ° (see Kohn and Trantom [Soc. 75, 1155]).
Beispiel II. 3gExample II. 3 g
Ein Gemisch von 160 Teilen Isoamylbromid, 100 Teilen benzoesaurem Kali und 1 Teil Pyridin wird 30 bis 40 Minuten auf 120 bis 125 ° erhitzt. Die Aufarbeitung des Reaktionsgemisches geschieht, wie in Beispiel I angegeben. Das so gewonnene Isoamylbenzoat besitzt die in der Literatur beschriebenen Eigenschaften.A mixture of 160 parts of isoamyl bromide, 100 parts of potassium benzoate and 1 part of pyridine is heated to 120 to 125 ° for 30 to 40 minutes. Working up the reaction mixture happens as indicated in Example I. The isoamyl benzoate obtained in this way has those described in the literature Properties.
Beispiel III.Example III.
Ein Gemenge von 10 Teilen Diäthylrhodamin (Base), 6 Teilen Kaliumcarbonat, 30 Teilen Benzylchlorid und 0,2 Teilen Triäthylamin wird unter Rühren eine Stunde lang auf 115 bis 120° erhitzt. Man destilliert dann das überschüssige Benzylchlorid mit Wasserdampf ab und kocht den Rückstand mit schwacher Salzsäure wiederholt aus. Durch Fällen der salzsauren Lösung mit Kochsalz erhält man das Chlorhydrat des Diäthylrhodaminbenzylesters als metallisch glänzende Masse. Es löst sich leicht in Wasser und Alkohol mit blauroter Farbe und lebhafter grüngelber Fluoreszenz; die Lösung in konzentrierter Schwefelsäure ist zitronengelb. Aus der wässerigen Lösung fällen Alkalien den freien Benzylester in ziegelroten Flocken.A mixture of 10 parts of diethyl rhodamine (base), 6 parts of potassium carbonate, 30 parts Benzyl chloride and 0.2 part of triethylamine are stirred for one hour at 115 heated to 120 °. The excess benzyl chloride is then distilled with steam and the residue is repeatedly boiled with weak hydrochloric acid. By felling the Hydrochloric acid solution with common salt gives the hydrochloride of diethyl rhodamine benzyl ester as a shiny metallic mass. It dissolves easily in water and alcohol with a blue-red color and a more vivid green-yellow color Fluorescence; the solution in concentrated sulfuric acid is lemon yellow. From the watery Solution, alkalis precipitate the free benzyl ester in brick-red flakes.
Man erhitzt ein Gemisch von 100 Teilen anthrachinon-a-carbonsaurem Kali, 150 TeilenA mixture of 100 parts of anthraquinone-a-carboxylic acid potash, 150 parts, is heated
Chloressigsäureäthylester und 2 Teilen Triäthylamin 15 Minuten auf 140 bis 145°. Die Reaktionsmasse
wird mit Alkohol verdünnt und die Lösung heiß vom ausgeschiedenen Chlorkalium
abfiltriert. Beim Erkalten kristallisiert reiner 2 - Anthrachinonylcarbonylglykolsäureätjiylester.
Er ist unlöslich in Wasser, verdünnten Säuren und Alkalien, ziemlich leicht löslich
in heißem Alkohol, Eisessig und Benzol, aus 10,denen er beim Abkühlen in feinen, schwach
: ' gelblichen Nädelchen vom Schmelzpunkt 13g
bis/1400 kristallisiert. Seine Lösung in konzentrierter
Schwefelsäure ist zitronengelb.
f Läßt man in vorstehenden Beispielen den J 15 Zusatz der organischen Basen weg, so tritt
/auch bei langem Kochen keine oder höchstens ./.' spurenweise Bildung der Ester ein.Ethyl chloroacetate and 2 parts of triethylamine at 140 ° to 145 ° for 15 minutes. The reaction mass is diluted with alcohol and the solution is filtered off hot from the precipitated potassium chloride. On cooling, pure ethyl 2-anthraquinonylcarbonylglycolate crystallizes. It is insoluble in water, dilute acids and alkalis, rather easily soluble in hot alcohol, glacial acetic acid and benzene, in Figure 10, where it during cooling in fine, weak: crystallized 'yellow needles of melting point 13g to / 140 0th Its solution in concentrated sulfuric acid is lemon yellow.
f is allowed to in the above examples 15 J addition of the organic bases away so enters / even after long cooking no or at most ./. ' trace formation of the ester.
■'/ ■ Beispiel V.■ '/ ■ Example V.
Man erwärmt 100 Teile i-chloranthrachinon-2-carbonsaures Kali mit 120 Teilen Benzylchlorid und 2 Teilen Pyridin auf 95 bis 100 ° und rührt die Mischung 30 Minuten bei dieser Temperatur. Nach dem Abdestillieren des unverbrauchten Benzylchlorids im Vakuum oder mit Dampf hinterbleibt der i-Chloranthrachinon-2-carbonsäurebenzylester als gelblich gefärbtes Kristallpulver in nahezu chemisch reinem Zustand. Ganz rein erhält man ihn durch Umkristallisieren aus Eisessig oder Alkohol unter Zusatz von Tierkohle. Er bildet schwach gelblich gefärbte Nadeln vom Schmelzpunkt 135 bis 136 °. Er ist unlöslich in Wasser, verdünnten Säuren und Alkalien, schwer löslich in kaltem Alkohol, Äther, Eisessig, leicht in kochendem Eisessig und höher siedenden Lösungsmitteln.' In konzentrierter Schwefelsäure löst er sich mit gelber Farbe unter Verseifung.100 parts of i-chloroanthraquinone-2-carboxylic acid are heated Potash with 120 parts of benzyl chloride and 2 parts of pyridine to 95 to 100 ° and stir the mixture for 30 minutes at this temperature. After distilling off the benzyl i-chloranthraquinone-2-carboxylate remains behind unused benzyl chloride in vacuo or with steam as a yellowish colored crystal powder in an almost chemically pure state. You can get it completely pure by recrystallization from glacial acetic acid or alcohol with the addition of animal charcoal. He educates pale yellowish colored needles with a melting point of 135 to 136 °. He is insoluble in Water, diluted acids and alkalis, sparingly soluble in cold alcohol, ether, glacial acetic acid, easily in boiling glacial acetic acid and higher boiling solvents. ' In concentrated Sulfuric acid, it dissolves with a yellow color with saponification.
Man kann die Reaktion auch in Gegenwart von Verdünnungsmitteln, wie Nitrobenzol, Chlorbenzol usw., ausführen; das Pyridin kann durch Chinolin, Triäthylamin, Piperidin, Dimethylanilin usw. ersetzt werden.The reaction can also be carried out in the presence of diluents such as nitrobenzene or chlorobenzene etc., execute; the pyridine can be replaced by quinoline, triethylamine, piperidine, dimethylaniline etc. to be replaced.
Führt man dagegen die Reaktion in Ab-Wesenheit einer organischen Base aus, so ist mehrstündiges Kochen des Gemisches nötig, um eine quantitative Umsetzung zu erzielen.If, on the other hand, the reaction is carried out in the absence of an organic base, then is several hours of cooking the mixture necessary to achieve quantitative conversion.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE268621C true DE268621C (en) |
Family
ID=525574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT268621D Active DE268621C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE268621C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183055A (en) * | 1991-12-27 | 1993-02-02 | Seager Stephen W J | Device for obtaining testicular or penile size and volume measurements |
| US5336232A (en) * | 1991-03-14 | 1994-08-09 | United States Surgical Corporation | Approximating apparatus for surgical jaw structure and method of using the same |
| US5358506A (en) * | 1991-03-14 | 1994-10-25 | United States Surgical Corporation | Approximating apparatus for surgical jaw structure |
| US5666964A (en) * | 1995-06-06 | 1997-09-16 | Meilus; Algis A. | Muscle treatment devices |
| US5749893A (en) * | 1993-04-30 | 1998-05-12 | United States Surgical Corporation | Surgical instrument having an articulated jaw structure and a detachable knife |
| US6716232B1 (en) | 1993-04-30 | 2004-04-06 | United States Surgical Corporation | Surgical instrument having an articulated jaw structure and a detachable knife |
-
0
- DE DENDAT268621D patent/DE268621C/de active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336232A (en) * | 1991-03-14 | 1994-08-09 | United States Surgical Corporation | Approximating apparatus for surgical jaw structure and method of using the same |
| US5358506A (en) * | 1991-03-14 | 1994-10-25 | United States Surgical Corporation | Approximating apparatus for surgical jaw structure |
| US5183055A (en) * | 1991-12-27 | 1993-02-02 | Seager Stephen W J | Device for obtaining testicular or penile size and volume measurements |
| US5749893A (en) * | 1993-04-30 | 1998-05-12 | United States Surgical Corporation | Surgical instrument having an articulated jaw structure and a detachable knife |
| US6716232B1 (en) | 1993-04-30 | 2004-04-06 | United States Surgical Corporation | Surgical instrument having an articulated jaw structure and a detachable knife |
| US5666964A (en) * | 1995-06-06 | 1997-09-16 | Meilus; Algis A. | Muscle treatment devices |
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