DE124150C - - Google Patents
Info
- Publication number
- DE124150C DE124150C DENDAT124150D DE124150DA DE124150C DE 124150 C DE124150 C DE 124150C DE NDAT124150 D DENDAT124150 D DE NDAT124150D DE 124150D A DE124150D A DE 124150DA DE 124150 C DE124150 C DE 124150C
- Authority
- DE
- Germany
- Prior art keywords
- fluorene
- anthracene
- potassium
- water
- compound
- 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.)
- Active
Links
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N Fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003112 potassium compounds Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 150000002220 fluorenes Chemical class 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- CWRYPZZKDGJXCA-UHFFFAOYSA-N Acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/1485—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds oxides; hydroxides; salts
-
- 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
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVIl24150 -KLASSE 12 o. - JVIl24150 - CLASS 12 o.
in BERLIN.in Berlin.
Verfahren zur Gewinnung von FluorenProcess for the production of fluorene
Patentirt im Deutschen Reiche vom 28. Juli 1900 ab.Patented in the German Empire on July 28, 1900.
Die im Rohanthracen vorkommenden niedrig schmelzenden Begleiter des Anthracene, das Acenaphten und Fluoren, sind neben Naphtalin und Phenanthren in .gröfster Menge-in dem Ausgufs enthalten, welcher gewonnen wird, wenn man nach dem' durch das Patent 111359 geschützten Verfahren zum Anreichern des Anthracens das geschmolzene Rohanthracen partiell erkalten läfst, zwecks Ausscheidung des Carbazols und Anthracene. Ein ähnliches fluorenhaltiges Gemisch ergiebt sich auch bei den Krystallisationen gewisser Schwerölfractionen. Durch oft wiederholte fractionirte Destillation konnten die in diesen Gemischen enthaltenen Stoffe zwar oberflächlich von einander getrennt . werden, ein einfaches Verfahren aber, das Fluoren für sich allein aus diesem Gemisch herauszunehmen, war bislang nicht bekannt.The low-melting companion of anthracene that occurs in raw anthracene, the Acenaphthene and fluorene, along with naphthalene and phenanthrene, are in the greatest quantity Include Ausgufs, which is obtained when looking for 'by patent 111359 Protected process for enriching the anthracene partially melted raw anthracene cools, for the purpose of excreting the carbazole and anthracene. A similar one containing fluorine Mixture also results from the crystallizations of certain heavy oil fractions. By often repeated fractionated distillation, those contained in these mixtures could be found Substances are superficially separated from each other. be a simple process but that It was not previously known to remove fluorene from this mixture on its own.
Es ist nun gelungen, ein solches Verfahren auszuarbeiten, unter Benutzung des bisher noch unbekannten Verhaltens des Fluorene, mit Kalihydrat verschmolzen eine Verbindung einzugehen. Aehnlich wie das Carbozol giebt nä'mlich auch das Fluoren, mit Aetzkali bei etwa 280 ° verschmolzen, nach der GleichungIt has now been possible to work out such a method, using what has been done so far unknown behavior of the fluorene, fused with potassium hydrate to form a compound. Similarly to carbozene, fluorene also gives, with caustic potash at about 280 ° merged, according to the equation
C13Zi10 + KOH = C13H9K+ H2O
eine feste Kaliumverbindung.C 13 Zi 10 + KOH = C 13 H 9 K + H 2 O
a solid potassium compound.
Im Grofsen verfährt man zweckmäfsig wie folgt: ' ·■■ - .In general one proceeds appropriately as follows: '· ■■ -.
1000 kg des oben erwähnten fluorenhaltigen Kohlenwasserstoffgemisches, wie man es beim Anreichern von Anthracen bezw. bei Krystallisationen des hochsiedenden Theeröls erhält, werden mit auf das vorhandene Fluoren abgestimmten Mengen Kalihydrat (in der Regel genügen davon 100 kg) in einem Kessel mit Rührwerk verschmolzen, worauf man die Temperatur der Schmelze langsam auf 2600 bis höchstens 3000 steigert. Es beginnt dann eine lebhafte Wasserabspaltung, welche bis zur Vollendung der Reaction anhält. Man läfst den Kesselinhalt ab und trennt die untere, in Form einer hellbraunen, schnell erstarrenden Schmelze entfallende Kaliumverbindung von der oberen, vorzugsweise aus'Acenaphten und Phenanthren bestehenden Kohlenwasserstoffschicht. Durch Eintragen der Kaliumverbindung in kaltes, noch besser heifses Wasser zersetzt sich dieselbe unter Rückbildung von Kalihydrat und Fluoren, welches letztere in Form eines krystallinisch erstarrenden braunen OeIs erhalten wird, das nunmehr nur noch einer Redestillation oder Um krystallisation aus Schwerbenzol bedarf, um sogleich rein zu sein.1000 kg of the above-mentioned fluorene-containing hydrocarbon mixture, as it is BEZW when enriching anthracene. obtained during crystallization of the high-boiling tar oil are fused with quantities of potassium hydrate (usually 100 kg are sufficient) in a kettle with a stirrer, matched to the fluorene present, whereupon the temperature of the melt is slowly increased to 260 0 to a maximum of 300 0 . A lively elimination of water then begins, which lasts until the reaction is complete. The contents of the kettle are drained off and the lower potassium compound, which is present in the form of a light brown, rapidly solidifying melt, is separated from the upper hydrocarbon layer, which preferably consists of acenaphthene and phenanthrene. When the potassium compound is introduced into cold, or even better hot, water, it decomposes with regression of potassium hydrate and fluorene, which the latter is obtained in the form of a crystalline solidifying brown oil, which now only requires redistillation or recrystallization from heavy benzene in order to immediately become pure be.
Das Fluoren soll zur Herstellung von Farbstoffen dienen.The fluorene is said to be used for the production of dyes.
Claims (1)
Verfahren zur Gewinnung von Fluoren aus fluorenhaltigen Kohlenwasserstoffgemischen, darin bestehend, dafs man die letzteren bei Temperaturen von etwa 260 bis 3000 mit Aetzkali verschmilzt, die entstandene Kaliumverbindung des Fluorene von der darauf schwimmenden Schicht von Kohlenwasserstoffen mechanisch trennt und alsdann durch Behandeln mit Wasser das Fluoren abscheidet.Patent claim: '
A process for recovering fluorene from fluorine-containing hydrocarbon mixtures, consisting of DAF, to the latter melts at temperatures of about 260 to 300 0 with potassium hydroxide, separating the resulting potassium compound of fluorenes of the floating thereon a layer of hydrocarbons mechanically and then by treating with water, the fluorene separates.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE124150C true DE124150C (en) |
Family
ID=392956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT124150D Active DE124150C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE124150C (en) |
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0
- DE DENDAT124150D patent/DE124150C/de active Active
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