DE290558C - - Google Patents
Info
- Publication number
- DE290558C DE290558C DENDAT290558D DE290558DA DE290558C DE 290558 C DE290558 C DE 290558C DE NDAT290558 D DENDAT290558 D DE NDAT290558D DE 290558D A DE290558D A DE 290558DA DE 290558 C DE290558 C DE 290558C
- Authority
- DE
- Germany
- Prior art keywords
- homologues
- solution
- water
- hydrocarbon
- ammoniacal
- 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.)
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- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 3
- BOFLDKIFLIFLJA-UHFFFAOYSA-N 2-methylbut-1-en-3-yne Chemical group CC(=C)C#C BOFLDKIFLIFLJA-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000005751 Copper oxide Substances 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- 229910000431 copper oxide Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- DKFHWNGVMWFBJE-UHFFFAOYSA-N 1-ethynylcyclohexene Chemical group C#CC1=CCCCC1 DKFHWNGVMWFBJE-UHFFFAOYSA-N 0.000 description 1
- DDCDEKHXBABHHI-UHFFFAOYSA-N C1(CCCCC1)O.C#C Chemical group C1(CCCCC1)O.C#C DDCDEKHXBABHHI-UHFFFAOYSA-N 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N Methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es wurde gefunden, daß das nach den Angaben des Patents 280226, Beispiel 1, und den Zusatzpatenten 284764 und 286920 erhältliche 3-Methylbutinol:It has been found that according to the information in Patent 280226, Example 1, and the Additional patents 284764 and 286920 available 3-methylbutynol:
CH3 CH 3
CH,CH,
-C-Ci-C-Ci
OHOH
XH,XH,
sowie die in analoger Weise erhältlichen Homologen und Analogen desselben durch Behandlung mit wasserabspaltenden Agenzien bei höheren Temperaturen in guter Ausbeute Isophenylacetylen und dessen Homologe und Analoge liefern, die als Ausgangsprodukte für therapeutisch oder technisch wertvolle Präparate Verwendung finden sollen. and the homologues and analogues thereof obtainable in an analogous manner by treatment with dehydrating agents at higher temperatures in good yield isophenylacetylene and its homologues and analogues which are used as starting products for therapeutically or technically valuable preparations are to be used.
Der Reaktionsverlauf war nicht vorauszu-The course of the reaction was not predictable.
ao sehen, weil 3-Methylbutmol beim Erhitzen in Aceton und Acetylen zerfällt und Körper mitao see because 3-methylbutmole when heated in Acetone and acetylene break down and body with
* dreifacher Bindung bei höherer Temperatur* triple bond at higher temperature
• überhaupt leicht zerfallen oder sich polymerisulfitlösung von etwaigen kleinen Mengen Aceton befreit. Nach dem Trocknen mit Chlorcalcium wird das so erhaltene Isopropenylacetylen destilliert. Es bildet eine farblose, leicht bewegliche Flüssigkeit von eigentümlich süßlichem Geruch; Siedepunkt 32 bis 32,5• Easily disintegrate at all or polymerisulphite solution from any small amounts of acetone freed. After drying with calcium chloride, the isopropenyl acetylene thus obtained becomes distilled. It forms a peculiar colorless, easily mobile liquid sweet smell; Boiling point 32 to 32.5
nD = 1,4158. Mit ammoniakalischer Silbersalzlösung erzeugt der Kohlenwasserstoff einen weißen, mit ammoniakalischer Kupferoxydullösung einen gelben Niederschlag.nD = 1.4158. With ammoniacal silver salt solution the hydrocarbon produces a white, with ammoniacal copper oxide solution a yellow precipitate.
500 Teile Methylpentinol werden langsam durch ein Rohr geschickt, in welchem eine etwa 80 cm lange Schicht Magnesiumsulfat auf 230 ° erwärmt ist. In der Vorlage sammelt sich das abgespaltene Wasser unter dem gebildeten Kohlenwasserstoff. Nach dem Abtrennen des Wassers wird er in der in Beispiel 1 beschriebenen Weise aufgearbeitet. Er ist eine500 parts of methylpentinol become slow sent through a pipe in which a layer of magnesium sulfate about 80 cm long 230 ° is heated. In the template, the separated water collects under the water that has formed Hydrocarbon. After the water has been separated off, it is used in the procedure described in Example 1 described way worked up. He is one
j leichtbewegliche, farblose, eigentümlich süßlichj easily mobile, colorless, peculiarly sweet
! riechende Flüssigkeit der Formel:! smelling liquid of the formula:
sieren.sate.
300 Teile 3-Methylbutinol läßt man langsam in ein Rohr tropfen, welches eine etwa 1 m lange, auf 250 ° erhitzte Schicht von entwässertem Magnesiumsulfat enthält. In einer mit Rückflußkühler versehenen, stark gekühlten Vorlage sammelt sich über dem abgespaltenen Wasser der neue* Kohlenwasserstoff. Er wird abgetrennt und durch Schütteln mit Bi-300 parts of 3-methylbutynol are allowed to slowly drip into a tube which is about 1 m contains long, heated to 250 ° layer of dehydrated magnesium sulfate. In a The strongly cooled receiver provided with a reflux condenser collects the new * hydrocarbon above the separated water. He is separated and shaken with bi
C H3 C H — C — C H3 CH 3 CH - C - CH 3
'■'·■'■.· c '■■'..''■ "Ζ
CH '■' · ■ '■. · C ' ■■ '..''■"Ζ
CH
vom Siedepunkt 67 bis 690; η D = 1,4332. Mit ammoniakalischer Silberlösung gibt sie eine weiße, mit ammoniakalischer Kupferoxydlösung eine gelbe Fällung.from the boiling point 67 to 69 0 ; η D = 1.4332. With ammoniacal silver solution it gives a white precipitate, with ammoniacal copper oxide solution it gives a yellow precipitate.
300 Teile Cyclohexanolacetylen werden in300 parts of cyclohexanol acetylene are in
ähnlicher Weise bei 220 ° durch ein Rohr getropft,' welches fein verteilte Tonerde enthält.similarly dripped through a tube at 220 °, which contains finely divided clay.
Es entsteht unter Wasserabspaltung Cyclohexenylacetylen Cyclohexenylacetylene is formed with elimination of water
CH3-CH2 CH 3 -CH 2
XCH2 — CH^ X CH 2 - CH ^
Die Aufarbeitung wird in der oben beschriebenen Weise vorgenommen. Der neue Kohlenwasserstoff siedet bei 148 bis 151 °. Er stellt eine petroleumähnlich riechende Flüssigkeit dar.Working up is carried out in the manner described above. The new hydrocarbon boils at 148 to 151 °. Created is a liquid that smells like petroleum.
20°20 °
η D = 1,4922. Mit ammoniakalischer Silberlösung gibt er einen weißen, mit ammoniakaao lischer Kupferoxydullösung einen grünlichen Niederschlag.η D = 1.4922. With ammoniacal silver solution he gives a white, with ammoniacal copper oxide solution a greenish one Precipitation.
An Stelle des in den Beispielen genannten Katalysators können natürlich auch andere Verwendung finden, wie Tonerde, Alaun usw.Instead of the catalyst mentioned in the examples, other catalysts can of course also be used Find uses such as clay, alum, etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE290558C true DE290558C (en) |
Family
ID=545514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT290558D Active DE290558C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE290558C (en) |
-
0
- DE DENDAT290558D patent/DE290558C/de active Active
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