DE536277C - Process for the oxidation of phenols - Google Patents
Process for the oxidation of phenolsInfo
- Publication number
- DE536277C DE536277C DEI29931D DEI0029931D DE536277C DE 536277 C DE536277 C DE 536277C DE I29931 D DEI29931 D DE I29931D DE I0029931 D DEI0029931 D DE I0029931D DE 536277 C DE536277 C DE 536277C
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- phenols
- oxygen
- parts
- product
- 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
Links
- 230000003647 oxidation Effects 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 150000002989 phenols Chemical class 0.000 title claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910003439 heavy metal oxide Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
- 239000005751 Copper oxide Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910000431 copper oxide Inorganic materials 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Oxydation von Phenolen Es wurde gefunden, daß sich Phenole in wertvolle Oxydationsprodukte überführen lassen, wenn man sie in der Wärme, aber in flüssiger Form, also geschmolzen oder gelöst, in Gegenwart von geringen Mengen von Schwermetalloxyden oder deren Salzen bei 15o° nicht übersteigenden Temperaturen mit trockenem Sauerstoff oder trockenen sauerstoffhaltigen Gasen behandelt. Es findet dabei in erster Linie eine Verkettung zu mehrkernigen Polyphenolen statt.Process for the oxidation of phenols It has been found that phenols can be converted into valuable oxidation products if they are in the heat, but in liquid form, i.e. melted or dissolved, in the presence of small amounts of heavy metal oxides or their salts at temperatures not exceeding 150 ° treated with dry oxygen or dry oxygen-containing gases. It finds primarily a linkage to polynuclear polyphenols instead.
Im Gegensatz zu der bekannten Arbeitsweise, Dinaphthole aus Naphtholen durch Oxydation mittels mindestens äquivalenten Mengen eines festen Oxydationsmittels darzüstellen, geschieht hier die Oxydation durch gasförmigen Sauerstoff in Gegenwart der als Sauerstoffüberträger wirkenden Schwermetallverbindungen.In contrast to the known working method, dinaphthols from naphthols by oxidation using at least equivalent amounts of a solid oxidizing agent represent, the oxidation takes place here by gaseous oxygen in the presence the heavy metal compounds acting as oxygen carriers.
Es ist zwar bekannt, Kresole und Xylenole bei Temperaturen von i5o° bis 17o° unter Zusatz eines Katalysators mit feuchter Luft oder mit feuchtem Sauerstoff zu behandeln. Die so erhaltenen, dunkel gefärbten, harzartigen Kondensationsprodukte haben chinonähnliche Eigenschaften und eine außerordentlich schwache Affinität zur Faser, während die erfindungsgemäß erhaltenen fast farblosen Verbindungen leicht auf die pflanzliche Faser ziehen und mit basischen Farbstoffen Farblacke zu bilden vermögen.It is known to use cresols and xylenols at temperatures of 150 ° up to 17o ° with the addition of a catalyst with moist air or with moist oxygen to treat. The dark colored, resinous condensation products thus obtained have quinone-like properties and an extremely weak affinity for Fiber, while the almost colorless compounds obtained according to the invention easily pull on the vegetable fibers and form color lakes with basic dyes capital.
Beispiel i i88 Teile geschmolzenes Phenol werden unter Zusatz von 18 Teilen gefälltem Kupferoxyd bei 13o bis 1q.0° mit einem kräftigen trockenen Luftstrom behandelt, wobei sich unter Wasserabspaltung innerhalb 25 bis 30 Stunden die Reaktionsmischung gelbbraun färbt. Nach dem Abdestillieren des unveränderten Phenols erhält man 4o Teile eines dunklen Rückstandes, welcher zwecks Reinigung kurz mit Wasserdampf behandelt und dann in verdünnter Natronlauge gelöst wird. Die braune, vom Kupferoxyd abfiltrierte alkalische Lösung scheidet beim Neutralisieren mit schwefliger Säure das Oxydationsprodukt als weißgrauen amorphen Niederschlag ab.Example i 88 parts of molten phenol are treated with the addition of 18 parts of precipitated copper oxide at 130 to 10 ° with a vigorous stream of dry air, the reaction mixture turning yellow-brown in color within 25 to 30 hours with elimination of water. After the unchanged phenol has been distilled off, 40 parts of a dark residue are obtained which, for the purpose of cleaning, is treated briefly with steam and then dissolved in dilute sodium hydroxide solution. The brown alkaline solution filtered off from the copper oxide separates the oxidation product as a white-gray amorphous precipitate when neutralized with sulphurous acid.
Die Verbindung zeigt keinen scharfen Schmelzpunkt und sintert bei i2o bis 13o° zu einer braunen Masse.. Sie ist ziemlich schwer löslich in Benzol und in Natriumcarbonatlösung, leicht löslich in Alkoholaceton und in verdünnter Natronlauge.The compound does not show a sharp melting point and sinters at i2o to 13o ° to a brown mass. It is rather sparingly soluble in benzene and in sodium carbonate solution, easily soluble in alcohol acetone and in dilute Caustic soda.
Bei der Zinkstaubdestillation liefert sie Diphenyl.In zinc dust distillation, it yields diphenyl.
Aus schwach alkalischer, mit Natriumchlorid versetzter Lösung zieht die Verbindung farblos auf die pflärizliche Faser und vermag mit basischen Farbstoffen, ähnlich wie Tanriirr oder PhenöIschwefelkondensationsprodukte, Farblacke zu bilden.-.Draws from a weakly alkaline solution mixed with sodium chloride the connection colorless on the vegetable fiber and can with basic dyes, similar to tannins or phenolic sulfur condensation products, To form color lakes .--.
Als Nebenprodukt entsteht bei der Oxydation des Phenols in geringer Menge das gut kristallisierende 2, q.'-Dioxydiphenyl vom Schmelzpunkt 16o bis 161'. - -Beispiel2 Verwendet man statt der in Beispiel i angegehenen Mengen an Kupferoxyd Braunstein, so erhält man die gleiche Umsetzung. Der Braunstein läßt sich auch durch Bleidioxyd, Kupferchlorid, Chromoxyd, Eisenoxyd, Nickeloxyd und ähnliche ersetzen. Beispie13 Die Mischung aus 216 Teilen m-Kresol und 2o Teilen Kupferoxyd wird bei 13o bis 135' mit trockener Luft behandelt. Nach 25 bis 30 Stunden erhält man eine braune Reaktionsmasse; zwecks Aufarbeitung und- Reinigung des entstandenen Reaktionsproduktes wird wie in Beispiel i verfahren. Man erhält so q.o Teile eines grauen amorphen Produktes, welches bei ioo bis iio° zu einer braunen Masse zusammensintert. In seinen chemischen Eigenschaften verhält es sich ähnlich wie das aus Phenol erhaltene Produkt. ' Beispiel4 288 Teile ß-Naphthol werden geschmolzen und in 'Gegenwart von 2o Teilen gefällten Kupfeeoxyds bei 15o° mit einem trockenen Luftstrom behandelt. _ Nach 15 bis 2o Stunden wird die rotbraune Reaktionsmasse durch Behandeln mit überhitztem Wasserdampf vom unveränderten ß-Naphthol befreit, der 'Rückstand zur Entfernung geringer Mengen von Phthalsäure mit verdünnter Natriumcarbonatlösung ausgezogen und der Rest durch Umlosen aus verdünnter Natronlauge oder ' geeigneten Lösungsmitteln als reines 2, 2'-Dioxy- i, z'-Dinaphthyl gewonnen.As a by-product of the oxidation of the phenol, a small amount of the well crystallizing 2, q .'-Dioxydiphenyl with a melting point of 160 to 161 'is formed. Example 2 If, instead of the amounts of copper oxide used in example i, manganese dioxide is used, the same reaction is obtained. The manganese dioxide can also be replaced by lead dioxide, copper chloride, chromium oxide, iron oxide, nickel oxide and the like. Beispie13 The mixture of 216 parts of m-cresol and 20 parts of copper oxide is treated with dry air at 130 to 135 minutes. After 25 to 30 hours, a brown reaction mass is obtained; for the purpose of working up and purifying the reaction product formed, the procedure is as in Example i. This gives qo parts of a gray amorphous product which sinters together at 100 to 100 ° to form a brown mass. In its chemical properties, it behaves similarly to the product obtained from phenol. Example 4 288 parts of β-naphthol are melted and treated in the presence of 20 parts of precipitated copper oxide at 150 ° with a stream of dry air. _ After 15 to 20 hours, the red-brown reaction mass is freed from unchanged β-naphthol by treatment with superheated steam, the residue is extracted with dilute sodium carbonate solution to remove small amounts of phthalic acid and the remainder is converted into pure 2 by dissolving dilute sodium hydroxide solution or suitable solvents , 2'-Dioxy- i, z'-Dinaphthyl obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29931D DE536277C (en) | 1927-01-05 | 1927-01-05 | Process for the oxidation of phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29931D DE536277C (en) | 1927-01-05 | 1927-01-05 | Process for the oxidation of phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE536277C true DE536277C (en) | 1931-10-22 |
Family
ID=7187468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI29931D Expired DE536277C (en) | 1927-01-05 | 1927-01-05 | Process for the oxidation of phenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE536277C (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3247262A (en) * | 1961-11-17 | 1966-04-19 | Dow Chemical Co | Process for making polyphenols |
| US4096190A (en) * | 1976-11-26 | 1978-06-20 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal ammonia complexes |
| US4098830A (en) * | 1977-02-18 | 1978-07-04 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of dicarboxylic acid compounds |
| US4100204A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of a hydroxy- or keto-acid compound |
| US4100202A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by cupric complexes |
| US4100206A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of keto alcohol compounds |
| US4100203A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of an oxime of a keto or aldehyde compound |
| US4100205A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of aminoketo compounds |
| US4108908A (en) * | 1977-02-18 | 1978-08-22 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of thio-acid compounds |
| EP0015104A1 (en) * | 1979-02-15 | 1980-09-03 | Ici Americas Inc. | Preparation of biphenol by the oxidative coupling of alkylphenols |
| US4438284A (en) | 1981-03-09 | 1984-03-20 | The Dow Chemical Company | Catalysts for oxidative coupling of phenols |
| US4447656A (en) * | 1981-03-09 | 1984-05-08 | The Dow Chemical Company | Solvent system for oxidative coupling process |
-
1927
- 1927-01-05 DE DEI29931D patent/DE536277C/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3247262A (en) * | 1961-11-17 | 1966-04-19 | Dow Chemical Co | Process for making polyphenols |
| US4096190A (en) * | 1976-11-26 | 1978-06-20 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal ammonia complexes |
| US4098830A (en) * | 1977-02-18 | 1978-07-04 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of dicarboxylic acid compounds |
| US4100204A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of a hydroxy- or keto-acid compound |
| US4100202A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by cupric complexes |
| US4100206A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of keto alcohol compounds |
| US4100203A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of an oxime of a keto or aldehyde compound |
| US4100205A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of aminoketo compounds |
| US4108908A (en) * | 1977-02-18 | 1978-08-22 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of thio-acid compounds |
| EP0015104A1 (en) * | 1979-02-15 | 1980-09-03 | Ici Americas Inc. | Preparation of biphenol by the oxidative coupling of alkylphenols |
| US4438284A (en) | 1981-03-09 | 1984-03-20 | The Dow Chemical Company | Catalysts for oxidative coupling of phenols |
| US4447656A (en) * | 1981-03-09 | 1984-05-08 | The Dow Chemical Company | Solvent system for oxidative coupling process |
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