AT96799B - Process for the preparation of 3-10 perylene quinone. - Google Patents
Process for the preparation of 3-10 perylene quinone.Info
- Publication number
- AT96799B AT96799B AT96799DA AT96799B AT 96799 B AT96799 B AT 96799B AT 96799D A AT96799D A AT 96799DA AT 96799 B AT96799 B AT 96799B
- Authority
- AT
- Austria
- Prior art keywords
- quinone
- preparation
- perylene
- perylene quinone
- anhydrous
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- IYYMDGDZPDXTGT-UHFFFAOYSA-N perylene-1,2-dione Chemical compound C1=CC(C2=C3C(=CC(C2=O)=O)C=CC=C32)=C3C2=CC=CC3=C1 IYYMDGDZPDXTGT-UHFFFAOYSA-N 0.000 title description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von 3-10 Perylenchinon.
EMI1.1
für sich oder unter Zusatz wasserfreier Alkalien wie Natriumkarbonat 1, 12-Dioxyperylen erhalten. Das durch Reduktion mit Zinkstaub in das Perylen und dieses durch Oxydation mit Chromsäure in das in der Literatur bekannte 3-10-Chinon übergeführt werden kann. Es wurde nun gefunden, dass man dieses
EMI1.2
Derivate mit wasserfreiem Aluminiumchlorid zu 3, 10-Dioxyperylen kondensiert und dieses der Luftoxydation aussetzt, wobei es in das entsprechende 3,10-Chinon übergeht. Dieses Chinon färbt aus kirschroter Küpe Baumwolle in hellgelben Tönen.
Ausführungsbeispiel : 1 Teil 4, 4'-Dioxy-l, 1'-Dinaphtyl wird mit 3 Teilen wasserfreiem Aluminiumchlorid innig verrieben und das Gemenge unter Feuchtigkeitsabschluss ein bis zwei Stunden auf 150 C erhitzt. Zur Isolierung des 3-10-Perylenchinons behandelt man das Rohprodukt mit verdünnter Natronlauge unter Zusatz von Natriumhydrosulfit, filtriert die entstehende Küpe ab und füllt das Chinon durch Einblasen von Luft aus. Dieses Chinon kann durch Umkristallisieren aus Nitrobenzol gereinigt werden. Jn seinen Eigenschaften stimmt es mit dem in der Literatur (Monatshefte für Chemie, 40. Band, S. 407) beschriebenen Chinon überein.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of 3-10 perylene quinone.
EMI1.1
obtained by itself or with the addition of anhydrous alkalis such as sodium carbonate 1, 12-dioxyperylene. Which can be converted into perylene by reduction with zinc dust and this can be converted into the 3-10-quinone known in the literature by oxidation with chromic acid. It has now been found that you can do this
EMI1.2
Derivatives are condensed with anhydrous aluminum chloride to give 3, 10-dioxyperylene and this is exposed to air oxidation, whereupon it changes into the corresponding 3,10-quinone. This quinone dyes cotton in light yellow tones from a cherry red vat.
Exemplary embodiment: 1 part of 4, 4'-dioxy-l, 1'-dinaphthyl is thoroughly triturated with 3 parts of anhydrous aluminum chloride and the mixture is heated to 150 ° C. for one to two hours in the absence of moisture. To isolate the 3-10 perylene quinone, the crude product is treated with dilute sodium hydroxide solution with the addition of sodium hydrosulfite, the vat formed is filtered off and the quinone is filled out by blowing in air. This quinone can be purified by recrystallization from nitrobenzene. In its properties it agrees with the quinone described in the literature (monthshefte fur Chemie, 40th volume, p. 407).
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT96799T | 1922-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT96799B true AT96799B (en) | 1924-04-25 |
Family
ID=3616312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT96799D AT96799B (en) | 1922-10-28 | 1922-10-28 | Process for the preparation of 3-10 perylene quinone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT96799B (en) |
-
1922
- 1922-10-28 AT AT96799D patent/AT96799B/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT96799B (en) | Process for the preparation of 3-10 perylene quinone. | |
| DE504646C (en) | Process for the preparation of anthraquinone and its offshoots | |
| DE611112C (en) | Process for the preparation of 1íñ4-dihaloanthraquinone-2-carboxylic acids | |
| DE462798C (en) | Process for the production of woolen dyes | |
| DE469911C (en) | Process for the preparation of thioethers of the anthraquinone series | |
| AT24655B (en) | Process for the preparation of 1,5- and 1,8-nitroanthraquinone sulfonic acid. | |
| DE412827C (en) | Process for the preparation of perylene dyes | |
| DE952896C (en) | Process for the preparation of diaminonaphthophenazines | |
| DE353221C (en) | Process for the preparation of a green pigment | |
| DE465506C (en) | Process for the preparation of a condensation product from Bz-1-nitro-2-methylbenzanthrone | |
| AT110530B (en) | Process for influencing aluminum chloride melts. | |
| DE715085C (en) | Process for the production of anthraquinone pellets | |
| CH216330A (en) | Process for the production of a sulfur dye. | |
| CH264198A (en) | Process for the production of a vat dye. | |
| CH210203A (en) | Process for the preparation of an anthraquinone vat dye. | |
| CH137955A (en) | Process for the preparation of a condensation product of the pyrenequinone series. | |
| CH132905A (en) | Procedure for the representation of 1. 2-Benzanthraquinone-peri-dicarboxylic acid anhydride. | |
| CH100395A (en) | Process for the preparation of a dye. | |
| CH224881A (en) | Process for the production of a vat dye. | |
| CH216593A (en) | Process for the preparation of a nitrogen-containing condensation product of fluoranthene. | |
| CH108856A (en) | Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. | |
| CH298031A (en) | Process for the preparation of an anthraquinone compound. | |
| DE1061933B (en) | Process for the production of nitrogenous compounds of the anthrone series | |
| CH140417A (en) | Process for the preparation of a nitrogenous compound of the anthanthrone series. | |
| CH148996A (en) | Process for the production of an etch-resistant dye of the gallocyanin series. |