AT69806B - Process for the preparation of cyclic ketones. - Google Patents
Process for the preparation of cyclic ketones.Info
- Publication number
- AT69806B AT69806B AT69806DA AT69806B AT 69806 B AT69806 B AT 69806B AT 69806D A AT69806D A AT 69806DA AT 69806 B AT69806 B AT 69806B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- cyclic ketones
- parts
- acid
- adipic acid
- Prior art date
Links
- 150000003997 cyclic ketones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CMDSJFALAFKSRE-UHFFFAOYSA-N 2-(2-methylpropyl)hexanedioic acid Chemical compound CC(C)CC(C(O)=O)CCCC(O)=O CMDSJFALAFKSRE-UHFFFAOYSA-N 0.000 description 1
- WDBZEBXYXWWDPJ-UHFFFAOYSA-N 3-(2-methylphenoxy)propanoic acid Chemical compound CC1=CC=CC=C1OCCC(O)=O WDBZEBXYXWWDPJ-UHFFFAOYSA-N 0.000 description 1
- SYEOWUNSTUDKGM-YFKPBYRVSA-N 3-methyladipic acid Chemical compound OC(=O)C[C@@H](C)CCC(O)=O SYEOWUNSTUDKGM-YFKPBYRVSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Beispiel 3 : 500 Teile Adipinsäure, die mit 20 Teilen Ferrosulfat vermischt sind, werden erhitzt, wie dies im vorstehenden Beispiel angegeben ist. Aus dem Destillat, das in der bereits oben geschilderten Weise aufgearbeitet wird, lässt sich Zyklopentanon in einer Ausbeute von über 90% gewinnen.
B e i s p i e 1 4 : 500 Teile ss-Methyladipinsäure werden in einem Destillationsgefäss im Luftbad auf 290 bis 2950 und dann später auf 300 bis 3050 erhitzt, bis kein Destillat mehr übergeht. Nach dem Entfernen der Hauptmenge des Wassers wird das Destillat, am besten unter ver-
EMI2.1
Beispiel 5 : 1000 Teile -Methyladipinsäure werden mit 10 Teilen Zinkstaub in einem Destillierkessel auf 270 bis 280 (Temperatur der geschmolzenen Säure) erhitzt, unter Durchleiten eines schwachen Kohlensäurestroms. Nach Beendigung der Operation wird in der oben beschriebenen Weise das gebildete Methylzyklopentanon isoliert. Ausbeute 81%.
BeispieJO : 200 Teile Korksäure werden mit 10 Teilen Eisenmehl vermischt und in einem Destilliergefäss im Luitbad solange auf 320 bis 3250 erhitzt, his kein Destillat mehr übergeht.
Nach der Abscheidung des Wassers wird das erhaltene, rohe Keton der Rektifikation unterworfen.
Man gewinnt so in guter Ausbeute das bekannte Suberon (Zykloheptanon vom Siedepunkt 1790).
An Stelle der in den Beispielen erwähnten Säuren können natürlich auch in analoger Weise die höheren Homologen der Adipinsäure Verwendung finden, wie z. B. Isobutyladipinsäure.
Ebenso lässt sich diese Reaktion auf die Substitutionsprodukte dieser Säure und ihre höheren Homologen, wie auf die entsprechenden alkyl-, aryl-, aralkyl-substituierten Körper sowie auf die halogenierten Substanzen dieser Körperklasse ausdehnen.
PATENT-ANSPRÜCHE :
1. Verfahren zur Darstellung von zyklischen Ketonen durch Erhitzen von Adipinsäure oder ihren Homologen bzw. ihrer Substitutionsprodukte, darin bestehend, dass man die zyklischen Ketone direkt aus der Adipinsäure oder ihren Homologen bzw. ihren Subst1tutionsprodukten durch blosses Erhitzen auf höhere Temperaturen darstellt.
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Example 3: 500 parts of adipic acid mixed with 20 parts of ferrous sulfate are heated as indicated in the previous example. Cyclopentanone can be obtained in a yield of over 90% from the distillate, which is worked up in the manner already described above.
Example 1 4: 500 parts of β-methyladipic acid are heated in a distillation vessel in an air bath to 290 to 2950 and then later to 300 to 3050 until no more distillate passes over. After most of the water has been removed, the distillate is
EMI2.1
Example 5: 1000 parts of methyladipic acid are heated with 10 parts of zinc dust in a still to 270 to 280 (temperature of the molten acid) while a weak stream of carbonic acid is passed through. After the operation has ended, the methylcyclopentanone formed is isolated in the manner described above. Yield 81%.
Example: 200 parts of suberic acid are mixed with 10 parts of iron flour and heated to 320 to 3250 in a distillation vessel in a Luit bath until no more distillate passes over.
After the water has been separated off, the crude ketone obtained is subjected to rectification.
The well-known suberone (cycloheptanone boiling point 1790) is obtained in good yield.
Instead of the acids mentioned in the examples, the higher homologues of adipic acid can of course also be used in an analogous manner, such as. B. isobutyl adipic acid.
This reaction can also be extended to the substitution products of this acid and its higher homologues, such as the corresponding alkyl, aryl, aralkyl-substituted bodies and the halogenated substances of this body class.
PATENT CLAIMS:
1. A method for the preparation of cyclic ketones by heating adipic acid or its homologues or its substitution products, consisting in that the cyclic ketones are prepared directly from adipic acid or its homologues or its substitution products by simply heating to higher temperatures.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69806X | 1911-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT69806B true AT69806B (en) | 1915-09-10 |
Family
ID=5635177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT69806D AT69806B (en) | 1911-12-21 | 1912-12-14 | Process for the preparation of cyclic ketones. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT69806B (en) |
-
1912
- 1912-12-14 AT AT69806D patent/AT69806B/en active
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