CH208953A - Process for the production of a fluoranthene derivative. - Google Patents
Process for the production of a fluoranthene derivative.Info
- Publication number
- CH208953A CH208953A CH208953DA CH208953A CH 208953 A CH208953 A CH 208953A CH 208953D A CH208953D A CH 208953DA CH 208953 A CH208953 A CH 208953A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- fluoranthene derivative
- parts
- dihalofluoranthene
- amino
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 title 1
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002219 fluoranthenes Chemical class 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 2
- QNHFVQNXYCIMHA-UHFFFAOYSA-N fluoranthene-1,2-diamine Chemical compound C12=CC=CC=C2C2=C(N)C(N)=CC3=CC=CC1=C32 QNHFVQNXYCIMHA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NANMFPDQTLMPNX-UHFFFAOYSA-N 1,2-dibromofluoranthene Chemical compound C12=CC=CC=C2C2=C(Br)C(Br)=CC3=CC=CC1=C32 NANMFPDQTLMPNX-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Fluoranthenderivates. Es wurde gefunden"dass ein Fluoranthen- derivat hergestellt werden kann, wenn. man 1 Mol Dihalogenfluoranthen mit 2 Molen 1- Amino - 4 - benzoylaminoanthraohinon um setzt.
Das erhaltene Produkt ist ein grünlich- schwarzes, kristallines Pulver, das konzen trierte Schwefelsäure oliv färbt, bei 410' schmilzt und sehr schwer verküpt. Auf Grund der Analyse liegt :das Di-(4'-benzoyl- amino-1'-anthrachinonyl)-diaminofluoranthen vor. Es stellt ein wertvolles Zwischenprodukt zur Herstellung von güpenfarfstoffen dar.
Das dem Verfahren als Ausgangsstoff dienende Dihalogenfluoranthen kann durch. Halogennieren von Fluoranthen biss zum Ein tritt von 2 Halogenatomen, z. B. in Nitro- benzol, hergestellt werden..
Die Umsetzung des Dihalogenfluoranthens mit 1- Amino - 4 - benzoylaminoanthrachinon wird vorteilhaft durch Erhitzen .der Kompo nenten in Lösu ngs- oder Verdünnungsmitteln, wie z. B. Amylalkohol, Nitrtibenzol oder Naphthalin, und zweckmässig in. Anwesenheit von Katalysatoren, sowie von säurebindenden Mitteln durchgefürt.
<I>Beispiel:</I> 18 Teile entwässertes Natriumacetat und 18 Teile wasserfreies Natriumacetat werden mit 8:
80 Teilen Nitrobenzol oo lange im Sie den gehalten, bis 50 Teile Nitrobenzol ab destilliert sind. Nach dem Abkühlen auf 200' werden 21,6 Teile Dibromfluoranthen, erhalten durch Bromieren von Fluoranthen in Nitiobenzol, 46 Teile 1-Amino-4-benzoyl- amino-anthrachinon und 1;
6 Teile Kupfer ohlorür zugesetzt und 4'8 Stunden bei 195 bis <B>205'</B> gerührt. Nun wird heiss filtriert, mit Nitrobenzol sowie mit Benzol und Alko hol gewaschen und das erhaltene Produkt zur weiteren Reinigung mit verdünnter Salz- säure ausgekocht, abfiltriert, ,
gewaschen und getrocknet.
Process for the production of a fluoranthene derivative. It has been found that a fluoranthene derivative can be prepared if 1 mole of dihalofluoranthene is reacted with 2 moles of 1-amino-4-benzoylaminoanthraquinone.
The product obtained is a greenish-black, crystalline powder which gives concentrated sulfuric acid an olive color, melts at 410 'and vents with great difficulty. Based on the analysis: the di- (4'-benzoylamino-1'-anthraquinonyl) diaminofluoranthene is present. It is a valuable intermediate product for the production of güpenfarfstoffe.
The process as starting material used dihalofluoranthene can by. Halogen kidneys of fluoranthene up to a occurs from 2 halogen atoms, z. B. in nitrobenzene.
The reaction of the dihalofluoranthene with 1-amino-4-benzoylaminoanthraquinone is advantageous by heating the components in solvents or diluents, such as. B. amyl alcohol, nitrtibenzene or naphthalene, and expediently carried out in the presence of catalysts and acid-binding agents.
<I> Example: </I> 18 parts of dehydrated sodium acetate and 18 parts of anhydrous sodium acetate are mixed with 8:
80 parts of nitrobenzene are kept in the oven for a long time until 50 parts of nitrobenzene have distilled off. After cooling to 200 ', 21.6 parts of dibromofluoranthene, obtained by brominating fluoranthene in nitiobenzene, 46 parts of 1-amino-4-benzoylamino-anthraquinone and 1;
6 parts copper oxide added and stirred for 4'8 hours at 195 to <B> 205 '</B>. It is then filtered hot, washed with nitrobenzene and with benzene and alcohol and the product obtained is boiled for further purification with dilute hydrochloric acid, filtered off,,
washed and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208953T | 1937-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH208953A true CH208953A (en) | 1940-03-15 |
Family
ID=4446307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH208953D CH208953A (en) | 1937-09-14 | 1937-09-14 | Process for the production of a fluoranthene derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH208953A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4414693A1 (en) * | 1994-04-27 | 1995-11-09 | Basf Ag | Prepn. of anthra-quinone-imide(s), useful as vat dye or intermediate |
| US5525743A (en) * | 1993-10-21 | 1996-06-11 | Basf Aktiengesellschaft | Preparation of anthraquinone imide compounds |
-
1937
- 1937-09-14 CH CH208953D patent/CH208953A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5525743A (en) * | 1993-10-21 | 1996-06-11 | Basf Aktiengesellschaft | Preparation of anthraquinone imide compounds |
| DE4414693A1 (en) * | 1994-04-27 | 1995-11-09 | Basf Ag | Prepn. of anthra-quinone-imide(s), useful as vat dye or intermediate |
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