DE268100C - - Google Patents
Info
- Publication number
- DE268100C DE268100C DENDAT268100D DE268100DA DE268100C DE 268100 C DE268100 C DE 268100C DE NDAT268100 D DENDAT268100 D DE NDAT268100D DE 268100D A DE268100D A DE 268100DA DE 268100 C DE268100 C DE 268100C
- Authority
- DE
- Germany
- Prior art keywords
- isoprene
- acid
- under reduced
- reduced pressure
- esters
- 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- -1 methylbutenol ester Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 230000003197 catalytic Effects 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- VBPSVYDSYVJIPX-UHFFFAOYSA-N pent-2-en-2-ol Chemical class CCC=C(C)O VBPSVYDSYVJIPX-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KJXYYEQKLYAHPZ-UHFFFAOYSA-M 2-methylbut-2-ene;bromide Chemical compound [Br-].CC=C(C)C KJXYYEQKLYAHPZ-UHFFFAOYSA-M 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L Barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L Nickel(II) chloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M Potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/213—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by splitting of esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JV^ 268100 -. KLASSE 12 o. GRUPPE- JV ^ 268100 -. CLASS 12 or GROUP
Verfahren zur Darstellung von Isopren.Process for the preparation of isoprene.
Zusatz zum Patent 255519.Addition to patent 255519.
Patentiert im Deutschen Reiche vom 9. August 1912 ab. Längste Dauer: 14. März 1926.Patented in the German Empire on August 9, 1912. Longest duration: March 14, 1926.
Das Patent 255519 betrifft ein Verfahren zur Darstellung von Diolefinen, welches u. a. darin besteht, daß man Halogenalkohole oder deren Ester bei höheren Temperaturen und zweckmäßig unter vermindertem Druck mit Substanzen behandelt, welche katalytisch Halogenwasserstoff und Säure abzuspalten vermögen. The 255519 patent relates to a process for the preparation of diolefins which, inter alia, contains. consists in that one halogen alcohols or their esters at higher temperatures and expediently treated under reduced pressure with substances which catalytically hydrogen halide and capable of splitting off acid.
Es wurde nun gefunden, daß sich auch die nach dem Patent 267553 erhältlichen Methylbutenolester vorteilhaft in Isopren überführen lassen, wenn man sie in Dampf form bei höherer Temperatur mit Mitteln behandelt, welche katalytisch Säure abzuspalten vermögen, nämlieh vor allem Tonerde, dann auch Baryumchlorid, Nickelchlorid usw. Auch hier ist es zweckmäßig, unter vermindertem Druck zu arbeiten.It has now been found that the methylbutenol esters obtainable according to the patent 267553 can advantageously be converted into isoprene if you can use them in vapor form at higher Temperature treated with agents which are able to split off acid catalytically, namely especially alumina, then also barium chloride, nickel chloride, etc. It is here too expedient to work under reduced pressure.
Es ist bekannt, daß aus Crotonylbromid durch Erhitzen mit Kaliumformiat auf 160 ° direkt Divinyl erhalten werden kann (Chem. Centralblatt 1899, II, S. 89). Hiervon unterscheidet sich das vorliegende Verfahren dadurch, daß hier als Ausgangsmaterial Methylbutenolester dienen, und daß die Abspaltung nnter Anwendung katalytisch wirkender Substanzen erfolgt. Beim Erhitzen für sich liefern diese Ester Isopren in nennenswerter Ausbeute nicht.It is known that from crotonyl bromide by heating with potassium formate to 160 ° Divinyl can be obtained directly (Chem. Centralblatt 1899, II, p. 89). This differs from this the present process is characterized by the fact that here methylbutenol ester as the starting material serve, and that the elimination with the use of catalytically active substances he follows. When heated by themselves, these esters provide isoprene in a significant yield not.
4040
Beispiel: Rohes Methylbutenolacetat (z.B. aus Trimethyläthylenbromid mittels Natriumacetat hergestellt) wird bei einem Druck von etwa 50 mm bei 4000 über Tonerde geleitet. Die den Kontaktraum verlassenden Dämpfe passieren einen Kühler, in dem sich die Hauptmenge 3S der gebildeten Essigsäure verdichtet; sie werden darauf in einer mit Lauge gefüllten Waschflasche völlig von Säure befreit und die Isoprendämpfe dann in einer auf 80 ° gekühlten Vorlage völlig verdichtet. Das in guter Ausbeute erhaltene Isopren ist sehr rein.Example: Raw Methylbutenolacetat (for example made of Trimethyläthylenbromid means sodium acetate) is mm at a pressure of about 50 passed over alumina at 400 0th The vapors leaving the contact space pass a cooler in which the bulk of the 3 S of the acetic acid formed is compressed; they are then completely freed from acid in a wash bottle filled with lye and the isoprene vapors are then completely compressed in a receiver cooled to 80 °. The isoprene obtained in good yield is very pure.
Entsprechend verfährt man, wenn man bei gewöhnlichem Druck arbeitet, wobei die Ausbeute etwas hinter der bei yermindertem Druck erhältlichen zurücksteht. Statt des Methyl- 4^ butenolacetats kann man auch andere Methylbutenolester, insbesondere solche aliphatisch^ Säuren, verwenden.The same procedure is followed when working under normal pressure, the yield being somewhat less than that obtainable under reduced pressure. Instead of methyl 4 ^ butenol acetate, it is also possible to use other methyl butenol esters, in particular such aliphatic acids.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE268100C true DE268100C (en) |
Family
ID=525100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT268100D Active DE268100C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE268100C (en) |
-
0
- DE DENDAT268100D patent/DE268100C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1244766B (en) | Process for the production of vinyl acetate | |
| DE541362C (en) | Process for the hydrogenation of polyoxy compounds | |
| DE68917099T2 (en) | Production of secondary aliphatic amines. | |
| DE268100C (en) | ||
| EP0118877B1 (en) | Process for the preparation of diacyloxybutenes | |
| DE838746C (en) | Process for the production of 2-AEthylhexanal- (1) or 2-AEthylhexanol- (1) | |
| DE625477C (en) | Process for the production of tetrahydrofurfural alcohol | |
| DE942990C (en) | Process for the preparation of pyridine and its homologues | |
| DE862016C (en) | Process for the preparation of tetrahydropyran derivatives | |
| DE712098C (en) | Process for the production of amines | |
| DE254473C (en) | ||
| AT209890B (en) | Process for the preparation of ω-aminonitriles | |
| DE1276032B (en) | Process for the preparation of cyclohexylamine | |
| DE890797C (en) | Process for the preparation of heterocyclic six-membered ring bonds containing a single nitrogen atom | |
| DE545849C (en) | Process for the production of butyl alcohol | |
| DE717062C (en) | Process for the production of aldehydes | |
| DE1468779A1 (en) | Process for the preparation of dicyclohexylamines from dicyclohexanols | |
| DE565160C (en) | Process for the production of unsaturated carbon compounds | |
| AT144989B (en) | Process for the preparation of hydrogenation products of the follicular hormone. | |
| DE1913198B2 (en) | ||
| DE894558C (en) | Process for the preparation of carbonic acid amides | |
| DE737640C (en) | Process for splitting hydrocarbon oils or for pressure hydrogenation of coal, tars and mineral oils | |
| DE734621C (en) | Process for the preparation of hydrogenation products of the follicular hormone | |
| AT218001B (en) | Process for the production of adiponitrile | |
| DE947303C (en) | Process for the refined hydrogenation of completely or partially saturated hydrocarbons |