DE42053C - Process for purifying the crude anthracene - Google Patents
Process for purifying the crude anthraceneInfo
- Publication number
- DE42053C DE42053C DENDAT42053D DE42053DA DE42053C DE 42053 C DE42053 C DE 42053C DE NDAT42053 D DENDAT42053 D DE NDAT42053D DE 42053D A DE42053D A DE 42053DA DE 42053 C DE42053 C DE 42053C
- Authority
- DE
- Germany
- Prior art keywords
- anthracene
- bases
- purifying
- crude
- benzene
- 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 1
- -1 carbazole Chemical compound 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004821 distillation Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
-
- 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
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
Das Rohanthracen, wie es sich direct aus den hochsiedenden Antheilen der Theeröle in festen krystallinischen Massen ausscheidet, enthält noch eine grofse Zahl fremdartiger Kohlenstoffverbindungen, die der Verarbeitung desselben zu Alizarin und verwandten Farbstoffen mehr oder weniger hinderlich sind. Ein Theil derselben kann allerdings durch Umkrystallisiren aus Benzol, Benzin, Alkohol und ähnlichen Lösungsmitteln, denen sich kürzlich noch die durch Patent No. 38417 geschützte Oelsäure angeschlossen hat, entfernt werden, d. h. das Rohanthracen kann angereichert werden, insofern gewisse Begleiter des Anthracens in diesen Lösungsmitteln leichter löslich als das letztere sind.The crude anthracene, as it is obtained directly from the high-boiling portions of the tar-oils in solid crystalline masses, still contains a large number of strange carbon compounds, which are more or less a hindrance to the processing of the same into alizarin and related dyes. A part it can, however, be obtained by recrystallization from benzene, gasoline, alcohol, and the like Solvents which have recently been treated with the patent no. 38417 protected oleic acid connected, removed, d. H. the raw anthracene can be enriched insofar certain companions of anthracene are more readily soluble in these solvents than the latter are.
Dieser Weg der Anreicherung führt aber nur unter recht namhaften Verlusten zur Gewinnung sehr hochprocentigen Anthracens. Noch schlimmer ist, dafs in solchem Anthracen einer der lästigsten Begleiter des Anthracens, das Carbazol, verbleibt, weil dasselbe in all den genannten Körpern reichlich ebenso schwer, nach Versuchen von Becche sogar erheblich schwerer löslich ist als das Anthracen.However, this way of enrichment leads to extraction only with considerable losses very high percentage anthracene. Worse still is that in such anthracene one of the most troublesome companions of anthracene, the carbazole, remains because the same abundantly just as heavy in all the named bodies, According to Becche's experiments, it is even considerably more difficult to dissolve than anthracene.
Um das Carbazol zu entfernen, bedarf es daher eines besonderen Processes; der bekannteste ist die verlustreiche Destillation des Rohanthracens über Aetzkali, bei welcher das Carbazol, an letzteres gebunden, zurückbleibt.A special process is therefore required to remove the carbazole; the most famous is the lossy distillation of crude anthracene over caustic potash, in which the Carbazole, bound to the latter, remains.
Aus all diesen Gründen gelangen zur Zeit fast ausschliefslich nur Rohanthracene in den Handel, deren Reingehalt ca. 40 pCt. nicht übersteigt, oder aber aus diesen erhaltene sogenannte gewaschene Anthracene mit einem Reingehalt von in der Regel nicht über 50 pCt.For all these reasons, only crude anthracenes are currently used almost exclusively in the Trade, the purity of which is approx. 40 pCt. does not exceed, or so-called obtained from these washed anthracenes with a purity of generally not more than 50 pCt.
Unser Verfahren gründet sich nun auf die bis dahin unbekannte, von uns entdeckte Thatsache, dafs die sämmtlichen Begleiter des Anthracens , einschliefslich Carbazol, in den Pyridin-, Chinolin- und Anilinbasen erheblich leichter löslich sind, als das Anthracen selbst, so dafs es mittelst eines einzigen Löseprocesses gelingt, nicht nur das Anthracen sogleich sehr hochprocentig, sondern dasselbe auch nahezu oder ganz frei von Carbazol und dessen Homologen zu gewinnen.Our procedure is now based on the previously unknown fact discovered by us, that all the companions of anthracene, including carbazole, are in the Pyridine, quinoline and aniline bases are considerably more soluble than the anthracene itself, so that by means of a single dissolving process, not only the anthracene is immediately successful high percentage, but also almost or completely free of carbazole and its homologues to win.
Als besonders geeignetes Lösungsmittel dienen uns die Theerbasen (Pyridinbasen), wie sie in den leichten Oelen des Steinkohlentheers enthalten sind und daraus am bequemsten nach dem Verfahren der Patente No. 34947 und No. 36372 gewonnen werden können. Die Fähigkeit dieser basischen Substanzen, das Anthracen anzureichern, geht so weit, dafs sie sogar noch ziemlich stark mit Benzol oder ähnlich wirkenden Körpern versetzt werden können, ohne diese namhaft einzubüfsen.We use the tar bases (pyridine bases) as a particularly suitable solvent, as described in are contained in the light oils of the coal horse and are most conveniently based on them the process of patent no. 34947 and No. 36372 can be obtained. The ability of these basic substances to Enriching anthracene goes so far that it is still quite strong with benzene or bodies with a similar effect can be displaced without sacrificing them significantly.
Man benutzt das auf die eine oder andere Weise erhaltene annähernd entwässerte ■ und rectificirte Theerbasengemisch wie folgt:One uses the approximately dehydrated ■ and obtained in one way or another rectified the tar base mixture as follows:
In einen mit Rührwerk versehenen Kessel, der von aufsen im Wasser- oder Dampfbade erhitzt werden kann, werden 1 Theil Rohanthracen und ι '/2 bis 2 Theile dieser Basen eingetragen und unter Umrühren erwärmt, bis alles gelöst ist. Nach dem Abkühlen der Lösung wird das auskrystallisirte Anthracen von der Mutterlauge auf bekannte Weise (Absaugen, Pressen oder Schleudern) getrennt. 1 part crude anthracene and 1/2 to 2 parts of these bases are introduced into a kettle equipped with a stirrer, which can be heated from the outside in a water or steam bath, and heated with stirring until everything is dissolved. After the solution has cooled, the anthracene which has crystallized out is separated from the mother liquor in a known manner (suction, pressing or centrifuging).
In gleicher Weise verfährt man, wenn an Stelle der Pyridinbasen die höhersiedendenThe same procedure is followed if the higher-boiling bases are used instead of the pyridine bases
Anilin- und Ghinolinbasen zur Anwendung kommen, in welchem Falle es vorzuziehen ist, dieselben mit gleichen Theilen Benzol (Solventnaphta) zu versetzen.Aniline and ghinoline bases are used, in which case it is preferable the same with equal parts benzene (solvent naphtha) to move.
Ein Rohanthracen von ca. 33 pCt. Reingehalt gab auf diese Weise, .wenn aus reinen Pyridinbasen in dem Verhältnifs von 1 : 1,75 umkrystallisirt, ein Anthracen von 82,5 pCt. Reingehalt, dagegen aus einem Gemisch von gleichen Theilen Benzol und Pyridinbasen in dem Verhältnifs von 1 : 2 umkrystallisirt ein Anthracen von 80 pCt., und endlich aus einem Gemisch von gleichen Theilen Anilin und Benzol ebenfalls im Verhältnifs von 1 : 2 umkrystallisirt ein Anthracen von ca. 75 pCt., welche Zahlen je nach der Stärke des angewendeten Rohanthracens und der Menge und Zusammensetzung des Lösungsmittels in etwas variiren.A raw anthracene of approx. 33 pCt. Purity gave in this way, if from pure Pyridine bases recrystallized in the ratio of 1: 1.75, an anthracene of 82.5 pCt. Pure content, on the other hand from a mixture of equal parts benzene and pyridine bases in in a ratio of 1: 2, an anthracene of 80 per cent., and finally from one, crystallizes out Mixture of equal parts of aniline and benzene also recrystallized in a ratio of 1: 2 an anthracene of about 75 pCt., which figures depending on the strength of the applied Raw anthracene and the amount and composition of the solvent vary somewhat.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE42053C true DE42053C (en) |
Family
ID=317480
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT42053D Expired - Lifetime DE42053C (en) | Process for purifying the crude anthracene |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE42053C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1218451B (en) * | 1957-09-05 | 1966-06-08 | Union Rheinische Braunkohlen | Process for the separation and recovery of heterocyclic compounds from high-temperature coal tar fractions |
DE3040431A1 (en) * | 1979-10-25 | 1981-05-07 | Instytut Chemii Przemysłowej, Warszawa | METHOD FOR DETERMINING AND PURIFYING ANTHRACEN FROM ANTHRACENOIL |
-
0
- DE DENDAT42053D patent/DE42053C/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1218451B (en) * | 1957-09-05 | 1966-06-08 | Union Rheinische Braunkohlen | Process for the separation and recovery of heterocyclic compounds from high-temperature coal tar fractions |
DE3040431A1 (en) * | 1979-10-25 | 1981-05-07 | Instytut Chemii Przemysłowej, Warszawa | METHOD FOR DETERMINING AND PURIFYING ANTHRACEN FROM ANTHRACENOIL |
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