CH139635A - Process for the preparation of diethyl allylomethylacetonitrile. - Google Patents
Process for the preparation of diethyl allylomethylacetonitrile.Info
- Publication number
- CH139635A CH139635A CH139635DA CH139635A CH 139635 A CH139635 A CH 139635A CH 139635D A CH139635D A CH 139635DA CH 139635 A CH139635 A CH 139635A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- diethyl
- preparation
- allylomethylacetonitrile
- boiling point
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 3
- 238000009835 boiling Methods 0.000 claims description 5
- QARLTYSAFQGMMB-UHFFFAOYSA-N 2-ethylbutanenitrile Chemical compound CCC(CC)C#N QARLTYSAFQGMMB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 diethyl allylacetonitrile Chemical compound 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von I)iäthyl-allylometliylacetonitril. In dem Schweizer Patent Nr. 122356 ist die Herstellung von Diäthylallylacetonitril durch Einwirkung von Allylierungsmitteln a.uf eine Alkaliverbirnd#-.ung des Diäthyl- acetonitrils beschrieben worden.
Gegenstand der vorliegenden Erfindung ist ein Verfä'hren zur Herstellung von Di- äthylallylomethylacetonitril, indem man ana log zu der in dem Schweizer Patent -'r.122356 beschriebenen Arbeitsweise auf eine Alkaliverbindung des Diäthylaceto- nitrils ein Allylmethylh!alo@geni,d einwirken lässt. Das Diäthyla.llylomethyl.acetonitril ist eine farblose Flüssigkeit mit dem Kochpunkt l06-107 C bei 2.6. mm Druck.
Durch Ver- seifung kann es in @d'as entsprechende Säure amid übergeführt werden.
<I>Beispiel:</I> In 200 gr Diäthylacetonitril werden 23 gr Natriumdraht in zwei Portionen unter Rüh ren eingetragen und die Reaktionstempera tur so geregelt, dass sie 3-5 nicht übersteigt. Nachdem alles Natrium umgesetzt ,ist, wer den 100 cm' wasserfreies Benzol und unter Kühlung 90 -r Allylomethylchlorid in 100 cm' trockenem Benzol zugegeben:.
Nach fünfstündigem Erhitzen unter Rüekfluss wird nach dem .Erkalten mit Wasser ver setzt und die Benzollösung mit Kochsalz lösung so lauge gewaschen, bis sie neutral reagiert. Durch fraktionierte Destillation wird Glas Diäthylallylomethylacetonitril vom Kochpunkt 106-107 bei 26 mm Druck er halten. ,Statt .des Chlorides kann man auch ein .anderes Allylomethylhalogenk anwen den.
Durch Verseifung mit propylalkoholi- schem Kali kann das entsprechende .Säure- amid erhalten werden, dessen Kochpunkt bei 125-130' bei 2,5. mm Druck, und dessen Schmelzpunkt bei 42 liegt.
Das Säuream.id kristallisiert in Form von Nadeln und ist leicht löslich in Ä.th.er, Alkohol, Benzol und Hexahydrobenzol, schwerer löslich in Petrol- äther und-, sehr schwer löslich in Wüsser.
Process for the preparation of I) ethyl-allylomethyl-acetonitrile. The Swiss patent No. 122356 describes the preparation of diethyl allylacetonitrile by the action of allylating agents on an alkali compound of diethyl acetonitrile.
The present invention relates to a process for the production of diethylallylomethylacetonitrile by allowing an allylmethylhalo @ geni, d to act on an alkali compound of diethylacetonitrile in a manner analogous to the procedure described in Swiss Patent No. 122356 . The diethyla.llylomethyl.acetonitrile is a colorless liquid with a boiling point of 106-107 C at 2.6. mm pressure.
It can be converted into the corresponding acid amide by saponification.
<I> Example: </I> 23 g of sodium wire are added in two portions to 200 g of diethyl acetonitrile while stirring and the reaction temperature is regulated so that it does not exceed 3-5. After all the sodium has reacted, whoever added 100 cm 'of anhydrous benzene and, while cooling, 90 -r allylomethyl chloride in 100 cm' of dry benzene :.
After heating under reflux for five hours, water is added after cooling and the benzene solution is washed with sodium chloride solution until it has a neutral reaction. By fractional distillation, glass diethylallylomethylacetonitrile of boiling point 106-107 at 26 mm pressure is kept. Instead of the chloride, another allylomethyl halogen can also be used.
The corresponding acid amide can be obtained by saponification with propyl alcoholic potash, the boiling point of which is at 125-130 'at 2.5. mm of pressure, and its melting point is 42.
The acid amide crystallizes in the form of needles and is easily soluble in ether, alcohol, benzene and hexahydrobenzene, less soluble in petroleum ether and - very poorly soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH122356T | 1928-09-20 | ||
| CH139635T | 1928-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139635A true CH139635A (en) | 1930-04-30 |
Family
ID=25709890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139635D CH139635A (en) | 1928-09-20 | 1928-09-20 | Process for the preparation of diethyl allylomethylacetonitrile. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139635A (en) |
-
1928
- 1928-09-20 CH CH139635D patent/CH139635A/en unknown
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