DE254473C - - Google Patents
Info
- Publication number
- DE254473C DE254473C DENDAT254473D DE254473DA DE254473C DE 254473 C DE254473 C DE 254473C DE NDAT254473 D DENDAT254473 D DE NDAT254473D DE 254473D A DE254473D A DE 254473DA DE 254473 C DE254473 C DE 254473C
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydro compounds
- vapors
- monohalogen
- substitution products
- tetrahydro
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 hydrogenated benzene hydrocarbons Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 210000004940 Nucleus Anatomy 0.000 claims 1
- 230000003197 catalytic Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WDIHJSXYQDMJHN-UHFFFAOYSA-L Barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N Cyclohexyl chloride Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L Nickel(II) chloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000395 magnesium oxide 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000000926 separation method Methods 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
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- .M 254473 KLASSE 12 o. GRUPPE- .M 254473 CLASS 12 or GROUP
Patentiert im Deutschen Reiche vom 21. November 1911 ab.Patented in the German Empire on November 21, 1911.
Tetrahydroverbindungen der Benzolreihe sind bisher aus Monochlorsubstitutionsprodukten völlig hydrierter Benzolkohlenwasserstoffe durch Erhitzen mit alkoholischem Kali oder Chinolin erhalten worden (Markownikoff, Ann. 302, 27; Fortey, Journ. Chem. Soc. 73, 941).Tetrahydro compounds of the benzene series have so far been made from monochlorine substitution products fully hydrogenated benzene hydrocarbons by heating with alcoholic potash or quinoline (Markownikoff, Ann. 302, 27; Fortey, Journ. Chem. Soc. 73, 941).
Bei der Verwendung des ersteren ist ein unreines Tetrahydrobenzol erhalten worden, wie die Angaben über das spezifische Gewicht zeigen (vgl. Zelinsky und Zelikow, Ber. 34, 3252); das Verfahren weist den weiteren sehr erheblichen Nachteil auf, daß die Abtrennung des Alkohols von dem nahezu bei derselben Temperatur siedenden Tetrahydrobenzol umständlich und kostspielig ist. Nach den Angaben von Fortey (Journ. Chem. Soc. 73, 941) erhält man bei Verwendung von Chinolin die besten Ausbeuten an Tetrahydrobenzol. Dieses Verfahren ist aber wegen des hohen Preises von Chinolin nicht technisch.Using the former, an impure tetrahydrobenzene has been obtained, as the information on the specific weight shows (see Zelinsky and Zelikow, Ber. 34, 3252); the process has the further very significant disadvantage that the separation the alcohol from the tetrahydrobenzene, which boils at almost the same temperature, is cumbersome and is costly. According to Fortey (Journ. Chem. Soc. 73, 941) the best yields of tetrahydrobenzene are obtained when quinoline is used. This However, because of the high price of quinoline, the process is not technical.
Es wurde nun gefunden, daß man auf sehr einfache Weise reine Tetrahydroverbindungen der Benzolreihe in vorzüglicher Ausbeute erhält, wenn man die Dämpfe von Monohalogen-Substitutionsprodukten der völlig hydrierten Benzolkohlenwasserstoffe bei gewöhnlichem oder vermindertem Druck über halogenwasserstoffbindende oder katalytisch wirkende Substanzen bei Temperaturen leitet, bei denen eine erhebliche Spaltung der gebildeten Tetrahydroverbindungen unter Bildung von Diolefinen (gemäß dem Verfahren des Patents 252499) noch nicht stattfindet.It has now been found that pure tetrahydro compounds can be obtained in a very simple manner of the benzene series is obtained in excellent yield if the vapors of monohalogen substitution products are used of the fully hydrogenated benzene hydrocarbons with ordinary or reduced pressure via hydrogen halide binding or catalytically active substances conducts at temperatures at which a considerable cleavage of the tetrahydro compounds formed with the formation of diolefins (according to the method of patent 252499) not yet taking place.
Als katalytisch wirkende Substanzen können beispielsweise Verwendung finden: Bariumchlorid, Tonerde, Nickelchlorid usw.The following can be used as catalytically active substances, for example: barium chloride, Alumina, nickel chloride, etc.
Durch einen Reaktionsraum, der mit Ätzkalk gefüllt und auf etwa 350 bis 450° (Innentemperatur) erhitzt wird, leitet man die Dämpfe von Chlorcyclohexan bei einem Druck von 15 bis 20 mm. Die den Reaktionsraum verlassenden Gase werden durch starke Abkühlung kondensiert und das Produkt, wenn nötig, durch einmalige Destillation gereinigt. Analog verfährt man beim Arbeiten unter gewöhnlichem Druck und bei Verwendung anderer salzsäurebindender Mittel, z. B. Magnesiumoxyd, Natronkalk usw.Through a reaction chamber that is filled with quicklime and heated to around 350 to 450 ° (internal temperature) is heated, the vapors of chlorocyclohexane are passed at a pressure of 15 to 20 mm. The the reaction space Leaving gases are condensed by strong cooling and the product, if necessary, purified by a single distillation. One proceeds in the same way when working under the ordinary Pressure and when using other hydrochloric acid binding agents, e.g. B. Magnesium Oxide, Soda lime etc.
Durch einen mit trockenem Bariumchlorid gefüllten und auf etwa 300 bis 400° (Innentemperatur) erhitzten Reaktionsraum leitet man bei einem Druck von 15 bis 20 mm die Dämpfe von Chlorcyclohexan. Die den Reaktionsraum verlassenden Dämpfe werden durch starke Abkühlung kondensiert und zur Entfernung anhaftender Salzsäure mit Natronlauge gewaschen. Das Reaktionsprodukt liefert alsdann nach dem Trocknen und Destillieren Tetrahydrobenzol.Through a filled with dry barium chloride and heated to about 300 to 400 ° (internal temperature) The heated reaction space is passed at a pressure of 15 to 20 mm Chlorocyclohexane fumes. The vapors leaving the reaction space are through strong cooling condenses and to remove adhering hydrochloric acid with sodium hydroxide solution washed. The reaction product then yields after drying and distillation Tetrahydrobenzene.
Analog verfährt man bei Verwendung anderer Kontaktsubstanzen.The same procedure is used when using other contact substances.
In der gleichen Weise werden andere Monohalogensubstitutionsprodukte der völlig hydrierten Benzolkohlenwasserstoffe in dieIn the same way, other monohalogen substitution products become fully the hydrogenated benzene hydrocarbons into the
entsprechenden Tetrahydroverbindungen übergeführt. corresponding tetrahydro compounds converted.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE254473C true DE254473C (en) |
Family
ID=512659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT254473D Active DE254473C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE254473C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10160707B2 (en) | 2014-06-11 | 2018-12-25 | Bayer Cropscience Aktiengesellschaft | Process for preparing 3-chloro-2-vinylphenol |
-
0
- DE DENDAT254473D patent/DE254473C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10160707B2 (en) | 2014-06-11 | 2018-12-25 | Bayer Cropscience Aktiengesellschaft | Process for preparing 3-chloro-2-vinylphenol |
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