DE172930C - - Google Patents
Info
- Publication number
- DE172930C DE172930C DENDAT172930D DE172930DA DE172930C DE 172930 C DE172930 C DE 172930C DE NDAT172930 D DENDAT172930 D DE NDAT172930D DE 172930D A DE172930D A DE 172930DA DE 172930 C DE172930 C DE 172930C
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- sulfuric acid
- aldehydes
- anthranol
- aromatic
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 1
- AUKRYONWZHRJRE-UHFFFAOYSA-N 9-anthrol Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=CC2=C1 AUKRYONWZHRJRE-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 150000004961 triphenylmethanes Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical class C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- JXACCPPRKJLNCJ-UHFFFAOYSA-N 4H-benzo[g]chromen-2-ol Chemical compound C1=CC=C2C=C(OC(O)=CC3)C3=CC2=C1 JXACCPPRKJLNCJ-UHFFFAOYSA-N 0.000 description 1
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N Paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es ist bekannt, daß hydroxylierte aromatische Verbindungen (Phenol, Resorcin usw.) sich mit Aldehyden unter Bildung von hydroxylierten Di- und Triphenylmethanderivaten kondensieren.It is known that hydroxylated aromatic compounds (phenol, resorcinol, etc.) deal with aldehydes to form hydroxylated di- and triphenylmethane derivatives condense.
Es wurde nun die Beobachtung gemacht, daß die sauerstoffhaltigen Reduktionsprodukte des Anthrachinons (Anthranole, Oxanthranole) sowie der Homologen und der SulfosäurenIt has now been observed that the oxygen-containing reduction products of anthraquinone (anthranols, oxanthranols) as well as homologues and sulfonic acids
ίο dieser Körper mit den Aldehyden der aromatischen Reihe sowohl wie mit denen der aliphatischen Reihe in anderer Weise reagieren, indem hierbei eigenartige, bisher nicht bekannte Derivate entstehen, welche keine Oxy-, di- bezw. -triphenylmethanderivate sind. Es ergibt sich dies u. a. daraus, daß sie in Alkalien unlöslich sind.ίο this body with the aldehydes of the aromatic Series as well as reacting with those of the aliphatic series in a different way, in that peculiar, hitherto unknown Derivatives are formed which do not contain any oxy, di- or. triphenylmethane derivatives are. It this results inter alia. from the fact that they are insoluble in alkalis.
10 kg Anthranol werden in 300 kg Schwefelsäure von 62 ° Be. eingetragen und mit 15 kg Benzaldehyd versetzt; schon nach kurzer Zeit und bei einer Temperatur von 30 bis 35° färbt sich die Mischung intensiv rot. Nach etwa 24 stündigem Stehen bei dieser Temperatur wird die Reaktionsmasse in Wasser gegossen und mit Äther ausgeschüttelt. Der Äther wird abdestilliert und der Rückstand mittels Wasserdampf vom unveränderten Benzaldehyd befreit. Es bleibt ein öliger Rückstand, der nach kurzer Zeit erstarrt und dann aus Alkohol umkristallisiert werden kann. Es werden auf diese Weise hellgelbe Kristallnadeln vom Schmelzpunkt 112 bis 1140 C. erhalten. Der Körper verhält sich indifferent gegen verdünnte Säuren und Alkalien; in konzentrierter Schwefelsäure löst er sich mit fuchsinroter Farbe.10 kg of anthranol are dissolved in 300 kg of sulfuric acid of 62 ° Be. registered and mixed with 15 kg of benzaldehyde; After a short time and at a temperature of 30 to 35 °, the mixture turns an intense red color. After standing for about 24 hours at this temperature, the reaction mass is poured into water and extracted with ether. The ether is distilled off and the residue is freed from unchanged benzaldehyde by means of steam. An oily residue remains, which solidifies after a short time and can then be recrystallized from alcohol. In this way, light yellow crystal needles with a melting point of 112 to 114 ° C. are obtained. The body is indifferent to dilute acids and alkalis; in concentrated sulfuric acid it dissolves with a fuchsin red color.
An Stelle des Anthranols kann mit demselben Erfolg Oxanthranol verwendet werden.In place of the anthranol, oxanthranol can be used with the same success.
10 kg Anthranol werden in 300 kg Schwefelsäure voiT 62 ° Be. eingetragen und versetzt mit 10 kg Paraldehyd; die Mischung färbt sich nach kurzer Zeit rotbraun. Nach 24stündigem Stehen bei einer Temperatur von 30 bis 450 C. wird die Reaktionsmasse in Wasser gegossen, wobei sich das gebildete Kondensationsprodukt in Form brauner Flocken ausscheidet. Es wird abfiltriert, gewaschen und bei gelinder Wärme getrocknet.10 kg of anthranol are dissolved in 300 kg of sulfuric acid from 62 ° Be. registered and mixed with 10 kg of paraldehyde; the mixture turns reddish brown after a short time. After standing for 24 hours at a temperature of 30 to 45 ° C., the reaction mass is poured into water, the condensation product formed separating out in the form of brown flakes. It is filtered off, washed and dried under mild heat.
Das rohe Produkt bildet ein gelbolives Pulver; gegen verdünnte Säuren und Alkalien verhält es sich indifferent; in den meisten organischen Lösungsmitteln ist es leicht löslich; die Lösung in konzentrierter Schwefelsäure ist rotbraun und fluoresziert.The raw product forms a yellow olive powder; against diluted acids and alkalis if it behaves indifferently; it is easily soluble in most organic solvents; the solution in concentrated sulfuric acid is red-brown and fluorescent.
In analoger Weise lassen sich andere Aldehyde sowohl der aromatischen als auch der aliphatischen Reihe bezw. deren Substitutionsprodukte mit Anthranol und Oxanthranolen des Anthrachinons oder seiner Derivate, insbesondere der Homologen oder Sulfosäuren des Anthrachinons, kondensieren.In an analogous manner, other aldehydes, both the aromatic and the aliphatic series respectively. their substitution products with anthranol and oxanthranols of the anthraquinone or its derivatives, in particular the homologues or sulfonic acids of the anthraquinone, condense.
Die im vorhergehenden beschriebenenThe ones described above
Kondensationsprodukte sollen zur Darstellung von Farbstoffen Verwendung finden.Condensation products should be used to represent dyes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE172930C true DE172930C (en) |
Family
ID=437780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT172930D Active DE172930C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE172930C (en) |
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0
- DE DENDAT172930D patent/DE172930C/de active Active
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