CH174079A - Process for the production of phthalonitrile. - Google Patents
Process for the production of phthalonitrile.Info
- Publication number
- CH174079A CH174079A CH174079DA CH174079A CH 174079 A CH174079 A CH 174079A CH 174079D A CH174079D A CH 174079DA CH 174079 A CH174079 A CH 174079A
- Authority
- CH
- Switzerland
- Prior art keywords
- phthalimide
- phthalonitrile
- ammonia
- production
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 title claims description 5
- 229920006391 phthalonitrile polymer Polymers 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 gate earth Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung von Phthalonitril. Es wurde gefunden, dass Phthalonitril in guter Ausbeute erhalten werden kann, wenn man Phthalimid mit Ammoniakgas in Gegen wart eines dehydratisierenden Katalysators auf 300-3500 C erhitzt, welcher bei der angewandten Temperatur fest bleibt und nicht leicht mit Ammoniak oder andern vorhan denen Verbindungen eine permanente Kom bination eingeht. Solche Katalysatoren sind z. B. Kieselerde, Thorerde, Tonerde und der gleichen. Gallertartige Kieselerde ist beson ders geeignet. Das Phthalimid kann z. B.
geschmolzen, zusammen mit dem Ammoniak gas, über den erhitzten Katalyten geleitet werden. Es ist jedoch vorteilhafter ein Ge misch von Ammoniakgas und Phthalimid- dampf zu verwenden. Das Phthalimid kann in situ in der Katalysatorkammer aus Phthal- säureanhydrid und Ammoniakgas hergestellt werden.
<I>Beispiel:</I> 25 Gewichtsteile Phthalimid werden er hitzt und der sich entwickelnde Dampf wird während einer Stunde über 288 Gewichts teile auf 360 0 C gehaltener, gallertartiger Kieselerde geleitet. Ein Ammoniakstrom wird mit dem Phthalimiddampf in einem solchen Verhältnis mitgeführt, dass in dem Gas stets reichlich Ammoniak vorhanden ist. Die flüs sigen und gasförmigen Reaktionsprodukte werden in einem grossen, gekühlten Behälter kondensiert.
Das feste Kondensat wird dann gepulvert und mit wässerigem Ätznatron um gerührt, um unverändertes Phthalimid und alkalilösliche Nebenprodukte zu entfernen und alles Phthalimid in Ammoniak und alkali- lösliche Produkte umzuwandeln.
Nach dem Filtern und Waschen verbleibt beinahe reines Phthalonitril mit einem Schmelzpunkt von 138-140 0 C. Die Ausbeute ist 75 % der theoretischen, auf das Phthalimid berechneten.
Das Endprodukt des vorliegenden Verfah rens ist bereits bekannt.
Process for the production of phthalonitrile. It has been found that phthalonitrile can be obtained in good yield if phthalimide is heated with ammonia gas in the presence of a dehydrating catalyst to 300-3500 C, which remains solid at the temperature used and does not easily become permanent with ammonia or other compounds Combination. Such catalysts are e.g. B. silica, gate earth, clay and the like. Gelatinous silica is particularly suitable. The phthalimide can e.g. B.
melted, together with the ammonia gas, are passed over the heated catalyst. However, it is more advantageous to use a mixture of ammonia gas and phthalimide vapor. The phthalimide can be produced in situ in the catalyst chamber from phthalic anhydride and ammonia gas.
<I> Example: </I> 25 parts by weight of phthalimide are heated and the vapor that develops is passed over 288 parts by weight of gelatinous silica held at 360 ° C. for one hour. A stream of ammonia is entrained with the phthalimide vapor in such a ratio that there is always ample ammonia in the gas. The liquid and gaseous reaction products are condensed in a large, cooled container.
The solid condensate is then powdered and stirred with aqueous caustic soda to remove unchanged phthalimide and alkali-soluble by-products and to convert all phthalimide into ammonia and alkali-soluble products.
After filtering and washing, almost pure phthalonitrile with a melting point of 138-140 ° C. remains. The yield is 75% of the theoretical calculated on the phthalimide.
The end product of the present process is already known.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB174079X | 1933-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH174079A true CH174079A (en) | 1934-12-31 |
Family
ID=10094660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH174079D CH174079A (en) | 1933-01-13 | 1934-01-12 | Process for the production of phthalonitrile. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH174079A (en) |
-
1934
- 1934-01-12 CH CH174079D patent/CH174079A/en unknown
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