DE205913C - - Google Patents
Info
- Publication number
- DE205913C DE205913C DE1907205913D DE205913DA DE205913C DE 205913 C DE205913 C DE 205913C DE 1907205913 D DE1907205913 D DE 1907205913D DE 205913D A DE205913D A DE 205913DA DE 205913 C DE205913 C DE 205913C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- potassium
- anthraquinone
- 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.)
- Expired - Lifetime
Links
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- -1 Halogen anthraquinones Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical class C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- YZHUMGUJCQRKBT-UHFFFAOYSA-M Sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 229940080281 sodium chlorate Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SROYVYGZVXMVOA-UHFFFAOYSA-L 9,10-dioxoanthracene-1,6-disulfonate Chemical compound O=C1C2=CC(S(=O)(=O)[O-])=CC=C2C(=O)C2=C1C=CC=C2S([O-])(=O)=O SROYVYGZVXMVOA-UHFFFAOYSA-L 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- BJZJPUSHTCPALE-UHFFFAOYSA-N 5-chloro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O BJZJPUSHTCPALE-UHFFFAOYSA-N 0.000 description 1
- OKONMFPEKSWGEU-UHFFFAOYSA-L 9,10-dioxoanthracene-2,7-disulfonate Chemical compound C1=C(S([O-])(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 OKONMFPEKSWGEU-UHFFFAOYSA-L 0.000 description 1
- YKUZYKBEGVZGEG-UHFFFAOYSA-N BrC1=CC=CC=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O Chemical compound BrC1=CC=CC=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O YKUZYKBEGVZGEG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/16—Quinones the quinoid structure being part of a condensed ring system containing three rings
- C07C50/18—Anthraquinones, i.e. C14H8O2
-
- 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
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 205913 KLASSE 12o. GRUPPE- M 205913 CLASS 12o. GROUP
Zusatz zum Patente 205195 vom 17. Mai 1907.Addendum to patent 205195 of May 17, 1907.
Patentiert im Deutschen Reiche vom 12. Juni 1907 ab. Längste Dauer: 16. Mai 1922.Patented in the German Empire on June 12, 1907. Longest duration: May 16, 1922.
Gemäß dem Verfahren des Hauptpatents kann man in Anthrachinondisulfosäuren die Sulfogruppen gegen Halogene austauschen.According to the method of the main patent, anthraquinone disulfonic acids can be used Replace sulfo groups with halogens.
Es wurde nun gefunden, daß diese Reaktion in zwei Phasen verläuft, indem nämlich zunächst nur eine Sulfogruppe gegen Halogen ausgetauscht wird und so Halogenanthrachinonsulfosäuren entstehen.It has now been found that this reaction takes place in two phases, namely initially only one sulfo group is exchanged for halogen and so halogenanthraquinone sulfonic acids develop.
10 Teile 1 · 5 - anthrachinondisulfosaures Natron werden in 400 Teilen Wasser und 50 Teilen Salzsäure von 190Be. gelöst und in die heiße Lösung 5 Teile Natriumchlorat in 50 Teilen Wasser gelöst langsam eingetragen. Die Einwirkung wird sofort unterbrochen, wenn wesentliche Mengen des Ausgangsmaterials nicht mehr nachweisbar sind. Man filtriert nun von etwa gebildetem 1 · 5 - Dichloranthrachinon ab und salzt mit Chlorkalium aus. Das so erhaltene Kaliumsalz - der 1 · 5 - Chloranthrachinonsulfosäure ist in Wasser wesentlich leichter löslich als das anthrachinon-l-5-disulfosaure Kalium. Es bildet schwach gelb gefärbte Nadeln, die sich in konzentrierter Schwefelsäure hellgelb lösen. . . ·10 parts of 1 · 5-anthraquinone disulphonate are dissolved in 400 parts of water and 50 parts of hydrochloric acid of 19 ° Be. dissolved and slowly introduced into the hot solution 5 parts of sodium chlorate dissolved in 50 parts of water. The action is immediately interrupted if substantial quantities of the starting material can no longer be detected. Any 1 · 5-dichloroanthraquinone formed is then filtered off and salted out with potassium chloride. The potassium salt obtained in this way - the 1 · 5 - chloranthraquinone sulfonic acid is much more soluble in water than the anthraquinone-1-5-disulfonic acid potassium. It forms pale yellow needles that dissolve in concentrated sulfuric acid pale yellow. . . ·
Io Teile 1 · 5 - anthrachinondisulfosaures Natron werden mit 8 bis 9 Teilen Brom und 40' bis 50 Teilen Wasser im Druckgefäß etwa 4 bis 5 Stunden auf 180 bis 190° erhitzt.Io parts 1 · 5-anthraquinone disulphonate are mixed with 8 to 9 parts of bromine and 40 'to 50 parts of water in the pressure vessel about Heated to 180 to 190 ° for 4 to 5 hours.
Nach dem Erkalten vermischt man die Reaktionsmasse mit 200 Teilen Wasser, kocht auf und filtriert von dem etwa schon gebildeten ι · 5 - Dibromanthrachinon ab. Aus dem Filtrat wird die ι · 5 - Bromanthrachinonsulfosäure mit Chlorkalium ausgesalzen. Sie kristallisiert in gelben Nadeln, die sich in Wasser leichter lösen wie das ι · 5 - anthrachinondisulfosaure Kalium. Die Lösung in Schwefelsäure ist gelb.After cooling, the reaction mass is mixed with 200 parts of water and boiled on and filtered off from any ι · 5-dibromoanthraquinone that has already formed. From the filtrate the ι · 5 - bromoanthraquinone sulfonic acid is salted out with potassium chloride. It crystallizes in yellow needles that dissolve more easily in water like ι · 5 - anthraquinone disulfonic acid Potassium. The solution in sulfuric acid is yellow.
10 Teile 1 · 8 - anthrachinondisulfosaures Natron werden in 400 Teilen Wasser und 50 Teilen Salzsäure von 190 Be. gelöst und bei etwa 900 langsam eine ioprozentige Lösung von Natriumchlorat in Wasser zugegeben, bis keine wesentliche Mengen von Ausgangsmaterial mehr nachzuweisen sind. Man filtriert von etwa schon gebildetem 1 · 8 - Dichloranthrachinon ab und scheidet mit Chlorkalium die I'8-Chloranthrac'hinonsulfosäure als Kaliumsalz ab. Das Kaliumsalz löst sich leichter in Wasser als das ι ■ 8 - anthrachinondisulfosaure Kalium. Es kristallisiert in hellgelben Nadeln und löst sich gelb in Schwefelsäure.10 parts of 1 · 8-anthraquinone-disulphonated soda are dissolved in 400 parts of water and 50 parts of hydrochloric acid of 19 0 Be. dissolved and slowly added at about 90 0 an 10 percent solution of sodium chlorate in water until no significant amounts of starting material can be detected. Any 1 · 8-dichloroanthraquinone that has already formed is filtered off and the 8-chloroanthrac'hinonsulfonic acid is separated off as the potassium salt with potassium chloride. The potassium salt dissolves more easily in water than the ι ■ 8 - anthraquinone disulfonic acid potassium. It crystallizes in light yellow needles and dissolves yellow in sulfuric acid.
10 Teile 2 · 7 - anthrachinondisulfosaures Natron werden in 200 Teilen Wasser gelöst, 8 bis 10 Teile Natriumchlorat zugegeben und dann bei etwa 90 ° so lange in kleinen Portionen10 parts of 2 · 7-anthraquinone disulfonate are dissolved in 200 parts of water, 8 to 10 parts of sodium chlorate were added and then at about 90 ° for so long in small portions
Salzsäure zugegeben, bis keine wesentlichen Mengen von Ausgangsmaterial mehr nachweisbar sind. Nach Zusatz von Chlorkalium läßt man abkühlen, filtriert ab und kristallisiert das erhaltene 2 · 7 - chloranthrachinonsulfosaure Kalium um, wobei man von etwa schon gebildetem 2 · 7 - Dichloranthrachinon abfiltriert. Das 2 · 7 - chloranthrachinonsulfosaure Kalium ist in Wasser schwer löslich. Es kristallisiert in Blättchen und löst sich gelb in Schwefelsäure. Hydrochloric acid was added until no significant amounts of starting material were detectable are. After adding potassium chloride, the mixture is allowed to cool, filtered off and crystallized the obtained 2 · 7 - chloranthraquinonesulfosaure potassium to, whereby one of about already formed 2 · 7 - dichloroanthraquinone filtered off. Potassium 2 · 7-chloroanthraquinone sulfo acid is sparingly soluble in water. It crystallizes in flakes and dissolves yellow in sulfuric acid.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT41026D AT41026B (en) | 1907-06-11 | 1909-02-01 | Process for the preparation of haloanthraquinones. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE205913C true DE205913C (en) |
Family
ID=468132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907205913D Expired - Lifetime DE205913C (en) | 1907-06-11 | 1907-06-11 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE205913C (en) |
-
1907
- 1907-06-11 DE DE1907205913D patent/DE205913C/de not_active Expired - Lifetime
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