DE2102476B2 - METHOD FOR PURIFYING O-HYDROXYDIPHENYL - Google Patents
METHOD FOR PURIFYING O-HYDROXYDIPHENYLInfo
- Publication number
- DE2102476B2 DE2102476B2 DE19712102476 DE2102476A DE2102476B2 DE 2102476 B2 DE2102476 B2 DE 2102476B2 DE 19712102476 DE19712102476 DE 19712102476 DE 2102476 A DE2102476 A DE 2102476A DE 2102476 B2 DE2102476 B2 DE 2102476B2
- Authority
- DE
- Germany
- Prior art keywords
- hydroxydiphenyl
- percent
- weight
- diphenyl
- pure
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
phenylgehalt auf unter 0,05 Gewichtsprozent und die diphenyl mit einer Reinheit von 99.9 Gewichtsprozent,phenyl content below 0.05 percent by weight and diphenyl with a purity of 99.9 percent by weight,
Anteile von Diphenylenoxid und o-Cyclohexylphenol das zur Verbesserung der Farbzahl nocheinmal destil-Portions of diphenylene oxide and o-cyclohexylphenol which are distilled again to improve the color number.
je unter 20 Gewichtsprozent abgefallen sind. Die liert wirdeach have fallen below 20 percent by weight. Which is lured
Mengen an Diphenylenoxid, o-Cyclohexylphenol undAmounts of diphenylene oxide, o-cyclohexylphenol and
an weiteren in kleinen Anteilen noch vorliegenden 5 ■on other 5 ■ still available in small proportions
Nebenprodukten sollten insgesamt nicht mehr als Beispiel!Total by-products should not be more than an example!
25 Gewichtsprozent betragen und der Gehalt an25 percent by weight and the content of
o-Hydroxydiphenyl im Sumpf nicht weniger als 75 Ge- An Hand des Fließschemas der Zeichnung läßt sicho-Hydroxydiphenyl in the sump no less than 75 times
wichtsprozent. ^as erfjncjungsgemäße Verfahren zur Reinigung desweight percentage. ^ as he fj nc proper method of cleaning the
Eine Kristallisation des durch Destillation vorge- io bei der Gasphasendehydrierung anfallenden o-Hydro-Crystallization of the o-hydro-
reinigten Rohproduktes kann auf verschiedene Weise xydiphenyl-Rohsemisches wie folgt ei läutern (Men-purified crude product can purify xydiphenyl crude mixture in various ways as follows (Men-
durchgeführt werden, z. B. durch Verwendung von genangaben in kg/h):be carried out, e.g. B. by using genes in kg / h):
aliphatischen und aromatischen Kohlenwasserstoffen Im Dehydrierungsreaktor 1 wird aus Dianon durchaliphatic and aromatic hydrocarbons In the dehydrogenation reactor 1 is made of dianon
als Lösungsmittel. katalytische Dehydrierung z. B. an einem Katalysator,as a solvent. catalytic dehydrogenation e.g. B. on a catalyst,
Besonders effektvoll und wirtschaftlich hat sich 15 der in der deutschen Offenlegungsschrift 2 049 80915 of the German Offenlegungsschrift 2,049,809 has proven to be particularly effective and economical
aber eine Kristallisation aus der Schmelze erwiesen. genannt ist, ein Gemisch erhalten, <5aß neben Wasser-but a crystallization from the melt has been proven. is called, a mixture is obtained, <5ass in addition to water
Eine technische Druchführung dieses Reinigungspro- stoff 0,5 kg leicht siedende Anteile wie Cyclohexan.A technical implementation of this cleaning substance 0.5 kg of low-boiling components such as cyclohexane.
zesses wird zweckmäßig in Rohrbündelkristallisations- Benzol, Cyclohexanon, Phenylcyclohexan u. a., 0,37 kgProcess is expediently in tube bundle crystallization benzene, cyclohexanone, phenylcyclohexane and others, 0.37 kg
apparaten durchgeführt, wobei vorteilhaft mehrere Phenol, 1,37 kg Diphenyl, 4,24 kg Diphenylenoxid.apparatus carried out, advantageously several phenol, 1.37 kg of diphenyl, 4.24 kg of diphenylene oxide.
Kristallisationsstufen hintereinandergeschaltet werden. 20 31,5 kg o-Hydroxydipher ·., 3,0 kg o-CyclohexylphenolCrystallization stages are connected in series. 20 31.5 kg of o-hydroxydipher, 3.0 kg of o-cyclohexylphenol
Dabei wird die Mutterlauge jeder Kristallisationsstufe sowie 0,4 kg an weiteren Nebenprodukten enthält. InThe mother liquor from each crystallization stage will contain 0.4 kg of other by-products. In
in die vorhergehende Stufe zurücKgeführt und das der Destillationsapparatur 3 destilliert man aus denreturned to the previous stage and the distillation apparatus 3 is distilled from the
Kristallisat der nächsten Stufe zugeführt. Gemischen der Dehydrierungsreaktoren 1 und 2 dieCrystals fed to the next stage. Mixtures of dehydrogenation reactors 1 and 2 die
Diese Art der Kristallisation aus der Schmelze kann leicht siedenden Anteile, Phenol, Diphenyl, einen TeilThis type of crystallization from the melt can have low-boiling fractions, phenol, diphenyl, some
auch in anderen Apparaten als Rohrbündelkristallisa- s„ des Diphenylenoxids und einen Teil weiterer in unter-also in other apparatus than tube bundle crystallization "of diphenylene oxide and some other in different
tionsapparaten durchgeführt werden. Die Anzahl der geordneter Menge vorliegender Nebenprodukte ab, sotion apparatus are carried out. The number of the ordered amount of existing by-products from, so
Kristallisationsstufen ist beliebig, sie wird in erster daß als Einsatz in die Kristallisationsstufe (Apparat 4)Crystallization stages are arbitrary, it is first used as an insert in the crystallization stage (apparatus 4)
Linie durch wirtschaftliche Überlegungen bestimmt. mit der Mutterlauge der 2. KristallisationsstufeLine determined by economic considerations. with the mother liquor from the 2nd crystallization stage
Prinzipiell läßt sich in einer Kristallisationsstufe reines (Apparat 5) 8,8 kg Diphenylenoxid, 88 kg o-Hydroxy-In principle, pure (apparatus 5) 8.8 kg of diphenylene oxide, 88 kg of o-hydroxy-
Produkt gewinnen, man erhält hierbei aber nur eine 30 diphenyl, 9,8 kg o-Cyclohexylphenol sowie 5,0 kg wei-Win product, but you only get 30 diphenyl, 9.8 kg o-cyclohexylphenol and 5.0 kg white
geringe Menge reines o-Hydroxydiphenyl. wenn man tere Nebenprodukte gelangen. In dem Rohrbündel-small amount of pure o-hydroxydiphenyl. if you get more by-products. In the tube bundle
von einem Rohprodukt mit etwa 75 Gewichtsprozent kristallisationsapparat 4 gewinnt man insgesamt 44,2 kgA total of 44.2 kg is obtained from a crude product with about 75 percent by weight of crystallization apparatus 4
Anteilen o-Hydroxyphenyl ausgeht. Mutterlauge mit 5,8 kg Diphenylenoxid, 28,6 kg o-Proportions of o-hydroxyphenyl goes out. Mother liquor with 5.8 kg diphenylene oxide, 28.6 kg o-
Auch durch Kristallisation in Gegenstromkristalli- Hydroxydiphenyl, 6,6 kg o-Cyclohexylphenol sowieAlso by crystallization in countercurrent crystalline hydroxydiphenyl, 6.6 kg of o-cyclohexylphenol and
sationsapparaten, wie sie z. B. in dem Buch »Frac- 35 3,2 kg weitere Nebenprodukte und insgesamt 67.4 kgsationsapparaten, as they are z. B. in the book »Frac- 35 3.2 kg of other by-products and a total of 67.4 kg
tionell Solidification«, 1. Auflage, 1967 von Zief und Kristallisat mit 3,0 kg Diphenylenoxid, 59,4 kgtionell Solidification ", 1st edition, 1967 by Zief and Kristallisat with 3.0 kg of diphenylene oxide, 59.4 kg
Wilcox im Kapitel »Column Crystallization«, S. 343, o-Hydroxydiphenyl, 3,2 kg o-Cyclorexylphenol sowieWilcox in the chapter "Column Crystallization", p. 343, o-Hydroxydiphenyl, 3.2 kg o-Cyclorexylphenol as well
beschrieben sind, läßt sich o-Hydruxydiphenyl ge- 1,8 kg an sonstigen Produkten. Während die Mutter-are described, o-Hydroxydiphenyl can be found in 1.8 kg of other products. While the mother
winn.n. Die Art und Weise der Kristallisation ist in lauge im Apparat 2 erneut dehydriert und der Destilla-winn.n. The way of crystallization is dehydrated again in caustic in apparatus 2 and the distiller
erster Linie von wirtschaftlichen Überlegungen ab- 40 tion 3 zugeführt wird, wird das Kristallisat zusammenFirst and foremost from economic considerations starting from 3, the crystallizate is brought together
hängig. Das im folgenden näher beschriebene Ver- mit der Mutterlauge der 3. Kristallisationsstufe impending. The process described in more detail below with the mother liquor of the 3rd crystallization stage in
fahren in Rohrbündelkristallisationsapparaten stellt Apparat 5 erneut aus der Schmelze kristallisiert. Dabeidriving in tube bundle crystallization apparatus sets apparatus 5 again crystallized from the melt. Included
eine besonders wirtschaftliche Ausführungsform dar. erhält man 33,8 kg Mutterlauge, bestehend aus 3,0 kga particularly economical embodiment. 33.8 kg of mother liquor consisting of 3.0 kg are obtained
Die Kristallisation in den Rohrbündelapparaten Diphenylenoxid, 25,6 kg o-Hydroxydiphenyl. 3,2 kg wird so ausgeführt, daß man das geschmolzene Sub- 45 o-Cyclohexylphenol sowie 2,0 kg weiteren Produkten, Stanzgemisch in den Rohrbündelapparat einfüllt und 81 kg Kristallisat, bestehend aus 1,6 kg Diphenylenvom Kristallisationspunkt der Schmelze langsam bis oxid, 77,5 kg o-Hydroxydiphenyl, 1,4 kg o-CycIowenige Grad Celsius über den eutektischen Punkt der hexylphenol sowie 0,5 kg weiteren Produkten und Schmelze abkühlt. Dann öffnet man das Ablaufventil, 10,6 kg o-Hydroxydiphenyl als Reinfraktion. Die wobei zunächst entektisches Gemisch abfließt. Beim 50 Kristallisatfraktion wird schließlich im Apparat 6 langsamen Aufheizen des Produktes fließt weiteres erneut gereinigt. Man gewinnt 57,8 kg Mutterlauge zunächst noch verunreinigtes Material aus dem Rohr- mit 1,6 kg Diphenylenoxid, 54,3kgo-Hydroxydiphenyl, bündelapparat ab, bis schließlich in den letzten Frak- 1,3 kg o-Cyclohexylphenol sovie 0,6 kg an weiteren tionen ein von Nebenprodukten freies o-Hydroxydi- Produkten und 23,2 kg Reinfraktion o-Hydroxydiphenyl abläuft. 55 phenyl. Die vereinigten Reinfraktionen aus den Kri-The crystallization in the tube bundle apparatus diphenylene oxide, 25.6 kg of o-hydroxydiphenyl. 3.2 kg is carried out in such a way that the melted sub- 45 o-cyclohexylphenol and 2.0 kg of other products, Punch mixture is poured into the tube bundle apparatus and 81 kg of crystals, consisting of 1.6 kg of diphenylene from Crystallization point of the melt slowly to oxide, 77.5 kg of o-hydroxydiphenyl, 1.4 kg of o-CycIowensige Degrees Celsius above the eutectic point of hexylphenol and 0.5 kg of other products and Melt cools. Then you open the drain valve, 10.6 kg of o-hydroxydiphenyl as a pure fraction. the initially entectic mixture flows off. When the 50 crystallizate fraction is finally in the apparatus 6 slow heating of the product flows further cleaned again. 57.8 kg of mother liquor are obtained initially still contaminated material from the pipe with 1.6 kg of diphenylene oxide, 54.3 kg of hydroxydiphenyl, bundling apparatus from until finally in the last fraction 1.3 kg of o-cyclohexylphenol asie 0.6 kg of more functions an o-hydroxydi-products free of by-products and 23.2 kg pure fraction o-hydroxydiphenyl expires. 55 phenyl. The combined pure fractions from the
In einer bei der Reinigung von c-Hydroxydiphenyl stallisationsapparaten 5 und 6 können abschließendIn one of the cleaning of c-Hydroxydiphenyl stallisationsapparaten 5 and 6 can finally
besonders zweckmäßigen Ausführungsform der Kri- zur Verbesserung der Farbzahl erneut destilliert wer-particularly expedient embodiment of the criterion to be redistilled to improve the color number
stallisation wird das Sumpfprodukt der fraktionierten den.
Destillation in Rohrbündelkristallisationsapparatenstallization becomes the bottom product of the fractionated den.
Distillation in tube bundle crystallization apparatus
in drei Stufen gereinigt. Dabei wird die Mutterlauge 60 B e i s ρ i e 1 2
jeder Kristallisationsstufe in die vorhergehende Stufecleaned in three stages. The mother liquor 60 B is ρ ie 1 2
each crystallization stage to the previous stage
zurückgeführt und das Kristallisat der nächsten Stufe a) Abtrennung von Diphenyl durch fraktionierterecycled and the crystals from the next stage a) separation of diphenyl by fractionated
zugeführt. Die Mutterlauge der 1. Kristallisationsstufe Destiliation aus dem Dehydrierungsgemisch
wird einer zweiten Dehydrierung unterworfen, umfed. The mother liquor of the 1st crystallization stage distillation from the dehydrogenation mixture
is subjected to a second dehydration in order to
Verbindungen wie o-CycIohexylphenol, o-Phenylcylco- 65 Einer Destillationskolonne mit 30 theoretischen hexanon, die in der Mutterlauge angereichert sind, Böden werden kontinuierlich 40,3 kg/h Dehydrierungsebenfalls in o-Hvdroxydiphenyl überzuführen. Man gemisch aus Dianon zugeführt. Das Dehydrierungserhält als Kristallisat der 2. und 3. Stufe o-Hydroxy- gemisch enthält durchschnittlich 74% o-Hydroxydi-Compounds such as o-CycIohexylphenol, o-Phenylcylco- 65 A distillation column with 30 theoretical hexanone, which are enriched in the mother liquor, soils are also continuously dehydrating 40.3 kg / h to be converted into o-hydroxydiphenyl. A mixture is fed from Dianon. That keeps dehydration as crystals of the 2nd and 3rd stage o-hydroxyl mixture contains an average of 74% o-hydroxydi-
phenyl, 20% Diphenylenoxid und o-CycIohexylphenol sowie 6% leichter siedende Anteile wie Diphenyl, Phenol, Phenylcyclohexan, Cyclohexanon und Cyclohexanol. Bei einem Rücklaufverhältnis von 1:30 liefert die Destillationskolonne ein Kopfprodukt, das die leichter siedenden Anteile des Dehydrierungsgemisches neben wenigen Prozenten Diphenylenoxid und o-Hydroxydipheny], insgesamt 2,6 kg/h, enthält. Als Sumpfprodukt, dessen Oehalt an Diphenyl weniger als 0,01 Gewichtsprozent beträgt, fallen 37,7 kg/h mit durchschnittlich 81 Gewichtsprozent o-Hydroxydiphenyl an.phenyl, 20% diphenylene oxide and o-cyclohexylphenol and 6% lower-boiling components such as diphenyl, phenol, phenylcyclohexane, cyclohexanone and cyclohexanol. With a reflux ratio of 1:30 it delivers the distillation column has an overhead product that contains the lower-boiling components of the dehydrogenation mixture in addition to a few percent of diphenylene oxide and o-hydroxydipheny], a total of 2.6 kg / h. as Bottom product whose diphenyl content is less than 0.01 percent by weight fall with 37.7 kg / h an average of 81 percent by weight of o-hydroxydiphenyl.
b) Reinigung des diphenylfreien, rohen o-Hydroxydiphenyls durch Kristallisationb) Purification of the diphenyl-free, crude o-hydroxydiphenyl by crystallization
Umlösen aus aliphatischen oder aromatischen Koh-S lenwasserstoffen: In einem 5-1-Rührkessel mit Doppelmantel und Ankerrührer werden 1 kg des 80 gewichtsprozentigen o-Hydroxydiphenyls in 400 ml Petroläther (Kp. 40 bis 600C) unter Erwärmen gelöst. Durch Abkühlen mit Wasser von 15° C unter sehr starkem ίο Rohren scheiden sich innerhalb einer Stunde 560 g/0,1 bis 0,3 mm lange Kristalle ab, deren Gehalt an o-Hydföxydiphenyl 99 Gewichtsprozent beträgt.Recrystallising from aliphatic or aromatic Koh-bons S: In a 5-1-stirred reactor with jacket and anchor stirrer, the 80 weight percent o-hydroxybiphenyl, 1 kg dissolved in 400 ml of petroleum ether (b.p. 40 to 60 0 C.) Under heating. By cooling with water at 15 ° C under very strong pipes, 560 g / 0.1 to 0.3 mm long crystals separate out within one hour, the o-hydroxydiphenyl content of 99% by weight.
Claims (1)
Cumolverfahren ersetzt wird, wurde zur Herstellung Damit ist gezeigt, daß sich auch durch mehrfache von o-Hydroxydiphenyl die Entwicklung eines neuen Umkristallisation selbst bei großen Ausbeuteverlusten Verfahrens mit neuen Reinigungsschritten erforderlich. kein reines o-Hydroxydiphenyl gewinnen läßt.The invention relates to a method for cleaning diphenyl content is 3.6 percent by weight. At von o-Hydrc ^ diphenyl. 30 repeated repetitions of the recrystallization obtained o-hydroxydiphenyl is of worldwide technical importance - one initially 258 g of crystallizate with a content of tung as a preservative for citrus fruits, as o-hydroxydiphenyl of 90 percent by weight and a carrier for dyes and al c - intermediate. Diphenyl of 3.7 percent by weight, then 206 g of crystal. So far, o-hydroxydipnenyl was obtained as a by-product with an o-hydroxydiphenyl content of 95.6 percent by weight in the pressure phenol synthesis from chlorobenzene and 3.4 percent by weight of diphenyl. To purify this technical weight percent further 190 g of crystals with an o-hydroxydiphenyl, the product is subjected to an o-hydroxydiphenyl content of 96.3 percent by weight Distillation. then 177 g of crystals with a content of Da now, for cost reasons, the pressure 40 o-hydroxydiphenyl of 96.8 percent by weight and of phenol synthesis through the phenol recovery after diphenyl of 3.1 percent by weight.
Cumene process is replaced, was used for production. It is thus shown that, even with multiple o-hydroxydiphenyl, the development of a new recrystallization process with new purification steps is necessary, even with large yield losses. no pure o-hydroxydiphenyl can be obtained.
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2102476A DE2102476C3 (en) | 1970-10-10 | 1971-01-20 | Process for the purification of o-hydroxydiphenyl |
AU34149/71A AU457367B2 (en) | 1970-10-10 | 1971-10-05 | Process for the manufacture of highly-purified 2-hydroxydiphenyl using a new catalyst |
CH1465171A CH563808A5 (en) | 1970-10-10 | 1971-10-07 | |
CH410275A CH566948A5 (en) | 1970-10-10 | 1971-10-07 | |
CA124,655A CA952538A (en) | 1970-10-10 | 1971-10-07 | Process for the manufacture of highly-purified 2-hydrozydiphenyl using a new catalyst |
BE773687A BE773687A (en) | 1971-01-20 | 1971-10-08 | Pure 2-hydroxydiphenyl prepn. - by fractional distillation followed by recrystallisation |
GB4696271A GB1340370A (en) | 1970-10-10 | 1971-10-08 | Process for the purification of o-hydroxydiphenyl |
ZA716764A ZA716764B (en) | 1971-01-20 | 1971-10-08 | Process for the purification of o-hydroxydiphenyl |
NL7113876.A NL166915C (en) | 1970-10-10 | 1971-10-08 | PROCESS FOR PREPARING VERY PURE 2-HYDROXYBIPHENYL BY HYDROGENATION OF WHOLE OR PARTI-HYDROGENATED 2-HYDROXYBIPHENYL USING A NEW CATALYST. |
FR7136350A FR2111179A5 (en) | 1970-10-10 | 1971-10-08 | |
GB4696171A GB1362284A (en) | 1970-10-10 | 1971-10-08 | Process for the production of a catalyst and its use in the produ ction of hydroxy-diphenyls |
FR7136351A FR2122841A5 (en) | 1970-10-10 | 1971-10-08 | |
IT53353/71A IT939518B (en) | 1971-01-20 | 1971-10-08 | PROCEDURE AND PLANT FOR PURIFYING OR HYDROXIDIFENYL |
ES395887A ES395887A1 (en) | 1971-01-20 | 1971-10-09 | Procedure for the purification of O-hydroxidiphenyl. (Machine-translation by Google Translate, not legally binding) |
JP8010771A JPS541699B1 (en) | 1970-10-10 | 1971-10-11 | |
GB4270572A GB1362285A (en) | 1970-10-10 | 1972-09-14 | Process for the production of a catalyst and its use in the produc tion of hydroxy-diphenyls |
US442156A US3923695A (en) | 1970-10-10 | 1974-02-13 | Catalyst for manufacturing highly purified 2-hydroxy-diphenyl catalyst and method of preparing catalyst |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2049809A DE2049809C3 (en) | 1970-10-10 | 1970-10-10 | Dehydrogenation catalyst |
DE2102476A DE2102476C3 (en) | 1970-10-10 | 1971-01-20 | Process for the purification of o-hydroxydiphenyl |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2102476A1 DE2102476A1 (en) | 1972-08-03 |
DE2102476B2 true DE2102476B2 (en) | 1973-08-02 |
DE2102476C3 DE2102476C3 (en) | 1974-02-28 |
Family
ID=25759865
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2102476A Expired DE2102476C3 (en) | 1970-10-10 | 1971-01-20 | Process for the purification of o-hydroxydiphenyl |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS541699B1 (en) |
AU (1) | AU457367B2 (en) |
CA (1) | CA952538A (en) |
CH (2) | CH566948A5 (en) |
DE (1) | DE2102476C3 (en) |
FR (2) | FR2111179A5 (en) |
GB (2) | GB1362284A (en) |
NL (1) | NL166915C (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5136445A (en) * | 1974-09-21 | 1976-03-27 | Sumitomo Chemical Co | Oo fuenirufuenooru no seiseiho |
DE2520893C2 (en) * | 1975-05-10 | 1982-03-11 | Bayer Ag, 5090 Leverkusen | Process for the production of diphenylamine |
JPS6129655U (en) * | 1984-07-28 | 1986-02-22 | 行雄 栗田 | Document display equipment |
CN102399135A (en) * | 2010-09-09 | 2012-04-04 | 东营远大化工有限公司 | O-phenylphenol preparation and separating and refining method |
CN103153456A (en) * | 2010-10-11 | 2013-06-12 | 埃克森美孚化学专利公司 | Process for producing phenol |
CN115745750B (en) * | 2022-09-28 | 2023-12-15 | 山东天隅新材料科技有限公司 | O-phenylphenol, preparation method and application thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1108221B (en) * | 1959-03-21 | 1961-06-08 | Bayer Ag | Method for controlling the mode of action of dehydrogenation catalysts for hydroaromatic compounds |
DE2049809C3 (en) * | 1970-10-10 | 1975-10-30 | Bayer Ag, 5090 Leverkusen | Dehydrogenation catalyst |
-
1971
- 1971-01-20 DE DE2102476A patent/DE2102476C3/en not_active Expired
- 1971-10-05 AU AU34149/71A patent/AU457367B2/en not_active Expired
- 1971-10-07 CH CH410275A patent/CH566948A5/xx not_active IP Right Cessation
- 1971-10-07 CA CA124,655A patent/CA952538A/en not_active Expired
- 1971-10-07 CH CH1465171A patent/CH563808A5/xx not_active IP Right Cessation
- 1971-10-08 NL NL7113876.A patent/NL166915C/en not_active IP Right Cessation
- 1971-10-08 GB GB4696171A patent/GB1362284A/en not_active Expired
- 1971-10-08 FR FR7136350A patent/FR2111179A5/fr not_active Expired
- 1971-10-08 GB GB4696271A patent/GB1340370A/en not_active Expired
- 1971-10-08 FR FR7136351A patent/FR2122841A5/fr not_active Expired
- 1971-10-11 JP JP8010771A patent/JPS541699B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
AU3414971A (en) | 1973-04-19 |
DE2102476A1 (en) | 1972-08-03 |
NL166915B (en) | 1981-05-15 |
CA952538A (en) | 1974-08-06 |
NL7113876A (en) | 1972-04-12 |
AU457367B2 (en) | 1975-01-30 |
GB1362284A (en) | 1974-08-07 |
CH566948A5 (en) | 1975-09-30 |
JPS541699B1 (en) | 1979-01-27 |
GB1340370A (en) | 1973-12-12 |
FR2122841A5 (en) | 1972-09-01 |
CH563808A5 (en) | 1975-07-15 |
FR2111179A5 (en) | 1972-06-02 |
DE2102476C3 (en) | 1974-02-28 |
NL166915C (en) | 1981-10-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
E77 | Valid patent as to the heymanns-index 1977 | ||
8339 | Ceased/non-payment of the annual fee |