AT98817B - Process for the oxidation of naphthalene. - Google Patents
Process for the oxidation of naphthalene.Info
- Publication number
- AT98817B AT98817B AT98817DA AT98817B AT 98817 B AT98817 B AT 98817B AT 98817D A AT98817D A AT 98817DA AT 98817 B AT98817 B AT 98817B
- Authority
- AT
- Austria
- Prior art keywords
- naphthalene
- oxidation
- phthalic anhydride
- catalyst
- reaction
- Prior art date
Links
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 22
- 230000003647 oxidation Effects 0.000 title description 7
- 238000007254 oxidation reaction Methods 0.000 title description 7
- 238000000034 method Methods 0.000 title description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Oxydation von Naphthalin.
Es ist bereits ein Verfahren zur Oxydation vonNaphthalin bekannt, bei welchen das in Dampfform ÜbergefiihrteNaphtha1inmitsauerstoffenthaltenden Gasgemischen, wie z. B. Luft. vermengt über Kontaktmassen strömt, die ein Metalloxyd enthalten. Als Katalysatoren wurden gewöhnlich Kohle oder Torf verwendet, denen Eisenoxyd zugesetzt wurde. Die angewendete Temperatur schwankt zwischen 150 und 200 . Die nach diesem Verfahren gewonnenen Endprodukte wurden jedoch in einer Form erhalten. welche ihre Trennung und Reinigung sehr erschweren.
Gemäss der vorliegenden Erfindung wird ah Katalysator Molybdänoxyd bei Temperaturen zwischen 2500 und 650 , am besten aber bei 5000. verwendet, wobei in der Hauptsache Phtalsäureanhydrid. u. zw. in ziemlich beträchtlicher Menge und in verhältnismässig reinem Zustande, erhalten wird.
Die Verwendung von Molybdänoxyd als Katalysator ist wohl schon bei der Oxydation von Anthrazen zu Anthrachinon zur Beschleunigung der Reaktion vorgeschlagen worden. Die Reaktion wird aber nicht in Gasform, wie im vorliegenden Falle, und weiters bei verhält nismässig niederer Temperatur durchgeführt. Es war daher nicht vorauszusehen, dass dem Molybdänoxyd als Katalysator bei der Oxydation von Naphtalin gerade bei hoher Temperatur eine für die Herstellung von Phtalsäureanhydrid ausschlaggebende Bedeutung zukommt.
Beispiel : Naphthalin in Dampfform wird mit Luft im Verhältnis von 18 Teilen Luft auf 1 Teil Naphthalin gemischt und in einem geeigneten Behälter bei einer Temperatur von 600 in innige Berührung
EMI1.1
gesammelt. Sie bestehen hauptsächlich aus Phtalsäureanhydrid, ferner aus Wasser, Kohlensäure, Kohlenmonoxyd, Benzoesäure, Naphtochinon und unveränderten Naphthalin. Die Ausbeute an Phtalsäureanhydrid bezogen auf das verwendete Naphthalin beträgt bei günstig eingestellten Bedingungen ungefähr 75%.
Wird die Reaktion nur bei etwa 2500 durchgefÜhrt, so ist die Ausbeute an Phtalsäureanhydrid eine verschwindend geringe, der grösste Teil desNaphthalins passiert den Katalysator ohne jede Einwirkung desselben. Es findet nur eine leichte Oxydation zu Oxydationsprodukten, wie z. B. Naphthochinon, statt.
Bei Temperaturen von etwa 550 und darüber nimmt die Ausbeute an Phtalsäureanhydrid ebenfalls ab, das erhaltene Produkt ist aber freier von Verunreinigungen, wie unverändertem Naphthalin und Naphthochinon. Offenbar ist dies darauf zurückzuführen, dass bei der höheren Temperatur die Reaktion viel kräftiger vor sich geht und eine vollständige Aufschliessung des reagierenden Materials stattfindet.
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**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
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Process for the oxidation of naphthalene.
A process for the oxidation of naphthalene is already known in which the naphthalene, which is converted into vapor form, is mixed with oxygen-containing gas mixtures, such as e.g. B. Air. mixed with contact masses that contain a metal oxide. The catalysts used were usually coal or peat, to which iron oxide was added. The temperature used varies between 150 and 200. However, the end products obtained by this process were obtained in a mold. which make their separation and purification very difficult.
According to the present invention, molybdenum oxide is used as the catalyst at temperatures between 2500 and 650, but best at 5000, with phthalic anhydride in the main. u. between in a fairly considerable amount and in a comparatively pure state.
The use of molybdenum oxide as a catalyst has probably already been proposed to accelerate the reaction in the oxidation of anthracene to anthraquinone. However, the reaction is not carried out in gaseous form, as in the present case, and furthermore at a relatively low temperature. It could therefore not be foreseen that molybdenum oxide as a catalyst in the oxidation of naphthalene would be of decisive importance for the production of phthalic anhydride, especially at high temperatures.
Example: Naphthalene in vapor form is mixed with air in the ratio of 18 parts of air to 1 part of naphthalene and in a suitable container at a temperature of 600 in intimate contact
EMI1.1
collected. They consist mainly of phthalic anhydride, as well as water, carbonic acid, carbon monoxide, benzoic acid, naphthoquinone and unchanged naphthalene. The yield of phthalic anhydride based on the naphthalene used is approximately 75% under favorable conditions.
If the reaction is only carried out at around 2500, the yield of phthalic anhydride is negligibly small, and most of the naphthalene passes through the catalyst without any influence from it. There is only a slight oxidation to oxidation products, such as. B. naphthoquinone instead.
At temperatures of about 550 and above, the yield of phthalic anhydride also decreases, but the product obtained is free of impurities such as unchanged naphthalene and naphthoquinone. Apparently this is due to the fact that at the higher temperature the reaction is much more powerful and the reacting material is completely broken down.
EMI1.2
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98817XA | 1917-05-12 | 1917-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT98817B true AT98817B (en) | 1924-12-27 |
Family
ID=21740265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT98817D AT98817B (en) | 1917-05-12 | 1920-04-03 | Process for the oxidation of naphthalene. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT98817B (en) |
-
1920
- 1920-04-03 AT AT98817D patent/AT98817B/en active
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