CH204239A - Process for the production of a dichlorochrysen. - Google Patents
Process for the production of a dichlorochrysen.Info
- Publication number
- CH204239A CH204239A CH204239DA CH204239A CH 204239 A CH204239 A CH 204239A CH 204239D A CH204239D A CH 204239DA CH 204239 A CH204239 A CH 204239A
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- melting point
- chrysene
- sulfur
- production
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims 4
- SPNXNIHLIKOOFV-UHFFFAOYSA-N 1,2-dichlorochrysene Chemical compound ClC1=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C=C1)Cl SPNXNIHLIKOOFV-UHFFFAOYSA-N 0.000 title claims 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- UGUZUUUNTAPFCG-UHFFFAOYSA-N 2,8-dichlorochrysene Chemical compound C1=CC(Cl)=CC2=CC=C3C4=CC=C(Cl)C=C4C=CC3=C21 UGUZUUUNTAPFCG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- -1 iodine, antimony halides Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Dieblorebrysens. Es wurde gefunden, dass ein Dichlor- chrysen hergestellt werden kann, wenn man auf Chrysen eine zur Dichlorierung ausrei chende Menge von chlorabgebenden Verbin dungen des Schwefels in Gegenwart von Halogenüberträgern einwirken lässt.
Das erhaltene Produkt ist 2,8-Dichlor- chrysen, besitzt einen Schmelzpunkt von <B>263-267'</B> und kann durch Umkristallisieren aus Nitrobenzol in weisse Nadeln vom Schmelz punkt 271 übergeführt werden. Es stellt ein wertvolles Zwischenprodukt für die Herstel lung von Farbstoffen dar.
Als chlorabgebende Verbindung des Schwe fels kommt beispielsweise Sulfuryloblorid in Betracht. Geeignete Halogenüberträger sind zum Beispiel Jod, Antimonhalogenide und Eisenchlorid. Die Einwirkung der chlorabge benden Verbindungen kann bei höherer Tem peratur, vorteilhaft in Gegenwart von Ver teilungsmitteln (Verdünnungs- und Lösungs mitteln erfolgen; solche Verteilungsmittel sind zum Beispiel Benzol, Chlorbenzol, Dichlor- benzol, Trichlorbenzol, Nitrobenzol, Chlor naphthalin und Tetrachloräthan.
<I>Beispiel:</I> 22,8 Teile Chrysen vom Schmelzpunkt <B>251'</B> werden in 200 Teilen Nitrobenzol ver teilt, 0,05 Teile Jod zugefügt und bei 15-25 in 3 Stunden 30 Teile Sulfurylohlorid zu tropfen lassen. Nun wird die Temperatur stufenweise erhöht, indem zuerst 4 Stunden bei 35-40', dann 16 Stunden bei<B>50-60'</B> gerührt wird. Nach dem Erkalten filtriert man das in guter Ausbeute erhaltene 2,8- Dichlorchrysen ab.
Method of manufacturing a dieblorebrysen. It has been found that a dichlorochrysenic can be produced if a sufficient amount of chlorine-releasing compounds of sulfur is allowed to act on chrysene in the presence of halogen carriers for dichlorination.
The product obtained is 2,8-dichlorochrysenic, has a melting point of 263-267 'and can be converted into white needles with a melting point of 271 by recrystallization from nitrobenzene. It is a valuable intermediate for the manufacture of dyes.
Sulfurylobloride, for example, can be used as the chlorine-releasing compound of the sulfur. Suitable halogen carriers are, for example, iodine, antimony halides and iron chloride. The chlorine-releasing compounds can act at a higher temperature, advantageously in the presence of distributing agents (diluents and solvents; such distributing agents are, for example, benzene, chlorobenzene, dichlorobenzene, trichlorobenzene, nitrobenzene, chloronaphthalene and tetrachloroethane.
<I> Example: </I> 22.8 parts of chrysene with a melting point of <B> 251 '</B> are divided into 200 parts of nitrobenzene, 0.05 parts of iodine are added and 30 parts of sulfurylochloride are added at 15-25 hours in 3 hours to drip. The temperature is now increased in stages by first stirring for 4 hours at 35-40 ', then 16 hours at <B> 50-60' </B>. After cooling, the 2,8-dichlorochrysene obtained in good yield is filtered off.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204239T | 1938-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204239A true CH204239A (en) | 1939-04-30 |
Family
ID=4444059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204239D CH204239A (en) | 1938-01-13 | 1938-01-13 | Process for the production of a dichlorochrysen. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204239A (en) |
-
1938
- 1938-01-13 CH CH204239D patent/CH204239A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT203485B (en) | Process for the production of new dinitrophenyl methacrylates | |
| DE920790C (en) | Process for the preparation of salicylic acid arylamides | |
| DE2250106A1 (en) | PROCESS FOR THE PRODUCTION OF 1,1'DIANTHRAQUINONYLENE | |
| DE1232944B (en) | Process for the preparation of meso-2,3-dibromosuccinic acid | |
| DE607539C (en) | Process for the preparation of aminoanthraquinones | |
| DE648088C (en) | Process for the preparation of secondary alkyl amines | |
| DE610319C (en) | Process for the preparation of 2 ', 5'-dichloro- or -dibromo-4'-alkyldiphenylmethane-2-carbonic acids | |
| DE3209426C2 (en) | ||
| DE560352C (en) | Process for the preparation of chlorine-containing derivatives of 4-methylbenzophenone-2'-carboxylic acid and anthraquinone-3-carboxylic acid | |
| CH639054A5 (en) | Process for the preparation of 4-bromo-2,5-dichlorophenol | |
| DE1768444C (en) | Process for the preparation of bromo derivatives of bis (hydroxyphenyO-dialkylmethanes | |
| DE639378C (en) | Process for the preparation of haloamino-1, 9-anthrapyrimidines | |
| DE2648944C3 (en) | Process for the preparation of N-phenyl-5-chloro-2-nitroaniline | |
| AT116717B (en) | Process for the preparation of nitriles of the perylene series. | |
| AT219616B (en) | Process for the production of dibenzyltin dichloride or dibenzyltin dichlorides substituted in the benzene nucleus | |
| DE506281C (en) | Process for the preparation of cyan derivatives of the perylene series | |
| AT273966B (en) | Process for the preparation of new 1- (polyhaloalkylthio) indazoles | |
| AT302306B (en) | Process for the preparation of new benzodiazepine derivatives | |
| DE873839C (en) | Process for the production of ª ‡, ª ‡ -dicyanaethyl ester | |
| CH170935A (en) | Process for the preparation of a vat dye of the anthraquinone series. | |
| DE1911305A1 (en) | Process for the preparation of chloroquinazoline derivatives | |
| CH211421A (en) | Process for the production of a chrysene derivative. | |
| CH347824A (en) | Process for the preparation of carboxamides | |
| CH207717A (en) | Process for the preparation of dibromofluoranthene. | |
| CH211431A (en) | Process for the production of a chrysene derivative. |