DE1068696B - Process for the preparation of /, δ-olefinically unsaturated ketones which are branched in the d-position - Google Patents
Process for the preparation of /, δ-olefinically unsaturated ketones which are branched in the d-positionInfo
- Publication number
- DE1068696B DE1068696B DENDAT1068696D DE1068696DB DE1068696B DE 1068696 B DE1068696 B DE 1068696B DE NDAT1068696 D DENDAT1068696 D DE NDAT1068696D DE 1068696D B DE1068696D B DE 1068696DB DE 1068696 B DE1068696 B DE 1068696B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- mixture
- ester
- acetoacetic
- methylbutenol
- 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.)
- Pending
Links
- 150000002576 ketones Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 23
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001298 alcohols Chemical class 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 4
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkyl acetoacetate Chemical compound 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930007744 linalool Natural products 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- VBPSVYDSYVJIPX-UHFFFAOYSA-N pent-2-en-2-ol Chemical compound CCC=C(C)O VBPSVYDSYVJIPX-UHFFFAOYSA-N 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N Pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- HEEAIHKOVDRAIC-AATRIKPKSA-N (E)-hex-2-en-2-ol Chemical compound CCC\C=C(/C)O HEEAIHKOVDRAIC-AATRIKPKSA-N 0.000 claims 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims 2
- LCZDCKMQSBGXAH-AWEZNQCLSA-N 3-[[3-[(2S)-2-amino-2-carboxyethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl]-5-phenylthiophene-2-carboxylic acid Chemical compound O=C1C(C)=CN(C[C@H](N)C(O)=O)C(=O)N1CC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 LCZDCKMQSBGXAH-AWEZNQCLSA-N 0.000 claims 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N 3-acetyl-6-methylpyran-2,4-dione Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims 1
- 239000004287 Dehydroacetic acid Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 235000019258 dehydroacetic acid Nutrition 0.000 claims 1
- 229940061632 dehydroacetic acid Drugs 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N oct-2-ene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000007659 semicarbazones Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FHSUFDYFOHSYHI-UHFFFAOYSA-M 3-oxopentanoate Chemical group CCC(=O)CC([O-])=O FHSUFDYFOHSYHI-UHFFFAOYSA-M 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N Crotyl alcohol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N Decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930008393 geraniol Natural products 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N hex-5-en-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N β-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es ist bekannt, ungesättigte Ketone, welche die Doppelbindung in γ, <5-Stellung enthalten, über die Acetessigester von/3, y-ungesättigten Alkoholen durch thermische Behandlung herzustellen.It is known that unsaturated ketones, which contain the double bond in the γ, <5-position, can be produced by thermal treatment via the acetoacetic esters of / 3, γ-unsaturated alcohols.
Diese Acetessigester wurden in der ersten Stufe des Verfahrens durch Umesterung des Acetessigsäuremethyl- oder -äthylesters mit den ß, y-ungesättigten Alkoholen oder durch Anlagerung derselben an Diketen gewonnen (J. Amer. Soc, Bd. 65, 1943, S. 1992 bis 1998).These acetoacetic esters were obtained in the first stage of the process by transesterification of the methyl or ethyl acetoacetate with the β, γ-unsaturated alcohols or by adding them to diketene (J. Amer. Soc, Vol. 65, 1943, pp. 1992 to 1998 ).
γ, (3-ungesättigte Ketone sind auch aus Acetessigsäureäthylester und höheren ungesättigten Alkoholen, z. B. Linalool und Geraniol, zugänglich, wenn man diese bei 200 bis 220° C längere Zeit erhitzt (Caroll, J. Chem. Soc, 1941, 507 bis 511). γ, (3-unsaturated ketones can also be obtained from ethyl acetoacetate and higher unsaturated alcohols, e.g. linalool and geraniol, if these are heated for a long time at 200 to 220 ° C (Caroll, J. Chem. Soc, 1941, 507 to 511).
Die niedrigen, olefinisch-ungesättigten Alkohole, deren Siedepunkt unter etwa 1600C liegt, konnten bisher nicht direkt mit Acetessigester zu ungesättigten Ketonen umgesetzt werden. Sie mußten in sehr schlechten Ausbeuten ■mach den beiden obengenannten umständlichen Methoden gewonnen werden.The lower, olefinically unsaturated alcohols, whose boiling point is below about 160 ° C., could not previously be converted directly with acetoacetic ester to form unsaturated ketones. They had to be obtained in very poor yields using the two cumbersome methods mentioned above.
Bei den tertiären Alkoholen, deren Siedepunkt unter 14O0C liegt, versagt auch die Methode der Umesterung. Zum Beispiel kann man eine Mischung von Acetessigester mit 2-Methylbuten-(3)-ol-(2) mehrere Tage unter Rückfluß kochen, ohne daß die gewünschte Umsetzung eintritt.The tertiary alcohols whose boiling point is below 14O 0 C, failed and the method of transesterification. For example, a mixture of acetoacetic ester with 2-methylbutene- (3) -ol- (2) can be refluxed for several days without the desired reaction occurring.
Kürzlich ist bekanntgeworden, daß auch niedere ungesättigte Alkohole, wie z. B. Allyl- oder Crotylalkohol, direkt mit Acetessigester in die entsprechenden ungesättigten Ketone, wie Allylaceton und 3-Methylhexen-(l)-oii-(5), überführbar sind, wenn man sie nach der britischen Patentschrift 695 313 auf Temperaturen von 300 bis 600° C erhitzt.It has recently become known that lower unsaturated alcohols, such as. B. allyl or crotyl alcohol, directly with acetoacetic ester into the corresponding unsaturated ketones, such as allylacetone and 3-methylhexen- (l) -oii- (5), are transferrable if they according to British patent specification 695 313 to temperatures of Heated between 300 and 600 ° C.
Dieser Reaktion sind indessen nur primäre und sekundäre ß, y-ungesättigte Alkohole zugänglich, da die tertiären ß, y-ungesättigten Alkohole bei diesen Bedingungen weitgehend unter Wasserabspaltung in Diolefine übergeführt werden. Zum Beispiel entsteht aus 2-Methylbuten-(3)-ol-(2) unter diesen Bedingungen Isopren und Wasser.However, only primary and secondary β, γ-unsaturated alcohols are accessible to this reaction, since the tertiary β, γ-unsaturated alcohols are largely converted into diolefins with elimination of water under these conditions. For example, isoprene and water are formed from 2-methylbutene- (3) -ol- (2) under these conditions.
Es wurde nun ein Verfahren zur Herstellung von in <5-Stellung verzweigten y, ö-olefinisch-ungesättigten Ketonen durch Umsetzung von tertiären ß, y-olefinisch-ungesättigten Alkoholen mit Alkylestem der Acetessigsäure bei 160 bis 25O0C in flüssiger Phase gefunden. Dieses Verfahren besteht darin, daß man unter 14O0C siedende, verzweigte tertiäre ß, y-olefinisch-ungesättigte Alkohole in Acetessigsäurealkylester oder in ein Gemisch von Acetessigsäureaikylester mit einem Lösungsmittel oder ein Gemisch des Alkohols mit Acetessigsäurealkylester in ein Lösungsmittel einführt, wobei das jeweilige Reaktionsmedium auf die Reaktionstemperatur vorgewärmt ist. It has now been found in the liquid phase, a method for preparing branched at <5 position y, ö-olefinically-unsaturated ketones by reacting tertiary ß, y-olefinically unsaturated alcohols with alkyl esters of acetoacetic acid at from 160 to 25O 0 C. This method consists in that one tertiary ß under 14O 0 C boiling, branched, y-olefinically unsaturated alcohols in alkyl acetoacetate or a mixture of Acetessigsäureaikylester with a solvent or a mixture of the alcohol with alkyl acetoacetate in a solvent is introduced, the respective reaction medium is preheated to the reaction temperature.
Geeignete Alkylester der Acetessigsäure sind insbesondere solche, die sich von Alkoholen mit 1 bis 5 Kohlen-Verfahren zur HerstellungSuitable alkyl esters of acetoacetic acid are, in particular, those which differ from alcohols with 1 to 5 carbons for the production
von in <5-Stellung verzweigten,of branched in <5-position,
γ, ö-olefinisch-ungesättigten Ketonen γ, δ-olefinically unsaturated ketones
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktienges ellschaft,Stock corporation,
Ludwigshafen/RheinLudwigshafen / Rhine
Dr. Heinrich Pasedach. und Dr. Matthias Seefelder,Dr. Heinrich Pasedach. and Dr. Matthias Seefelder,
Ludwigshafen/Rhein,
sind als Erfinder genannt wordenLudwigshafen / Rhine,
have been named as inventors
stoffatomen, vor allem von Methanol und Äthanol, ableiten.derive material atoms, especially from methanol and ethanol.
Man führt den ungesättigten Alkohol in flüssigen, auf 170 bis 180° C erhitzten Acetessigester oder in eine Lösung von Acetessigester in einem inerten Lösungsmittel ein, die ebenfalls auf 170 bis 1900C erhitzt ist, und destilliert laufend die niedrigsiedenden Komponenten ab. Dieses sind Äthylalkohol im Falle des Acetessigsäureäthylesters und der nicht in Reaktion getretene niedrigsiedende Alkohol. Die Reaktionstemperatur soll 160° C nicht unterschreiten. It leads to the unsaturated alcohol in the liquid, heated to 170 to 180 ° C or acetoacetic ester in a solution of acetoacetic ester in an inert solvent, which is also heated to 170 to 190 0 C, and distilled continuously from the low-boiling components. These are ethyl alcohol in the case of ethyl acetoacetate and the low-boiling alcohol that has not reacted. The reaction temperature should not fall below 160 ° C.
Als inerte Lösungsmittel sind z. B. Tetrahydronaphthalin, Dekahydronaphthalin, Naphthalin, Diphenyläther geeignet. Zweckmäßig verwendet man ein Lösungsmittel, das sich von dem entstehenden ungesättigten Keton leicht durch Destillation trennen läßt.As inert solvents are, for. B. tetrahydronaphthalene, decahydronaphthalene, naphthalene, diphenyl ether suitable. A solvent is expediently used which is different from the unsaturated ketone formed can easily be separated by distillation.
Man kann auch so verfahren, daß man ein auf die genannte Temperatur erhitztes hochsiedendes inertes Lösungsmittel vorlegt und ein Gemisch von Acetessigester und ungesättigtem Alkohol einführt. Auch in diesem Fall werden alle niedrigsiedenden Anteile laufend abdestilliert. One can also proceed in such a way that a high-boiling inert material heated to the temperature mentioned is used Submit solvent and introduce a mixture of acetoacetic ester and unsaturated alcohol. Also in this In case, all low-boiling components are continuously distilled off.
Zur Erreichung guter Ausbeuten ist es zweckmäßig, den ungesättigten Alkohol im Überschuß anzuwenden, z. B. im Molverhältnis 2:1.To achieve good yields, it is advisable to use the unsaturated alcohol in excess, e.g. B. in a molar ratio of 2: 1.
Das ungesättigte Keton gewinnt man nach beendeter Reaktion, was man am Aufhören der Gasentwicklung erkennt, durch fraktionierte Destillation.The unsaturated ketone is obtained after the reaction has ended, which is reflected in the cessation of gas evolution recognizes by fractional distillation.
Nach diesem Verfahren, das man auch unter erhöhtem Druck durchführen kann, sind die ungesättigten Ketone in einfacher Weise in einer Reaktionsstufe mit guten Ausbeuten herzustellen.This process, which can also be carried out under increased pressure, is used to create the unsaturated ketones to be prepared in a simple manner in one reaction stage with good yields.
909 648/419909 648/419
Claims (1)
wiegend Äthylalkohol und Methylbutenol enthält.Obtained distillate of bp 75 to 90 ° C, which vor- 45 methylhepten ^ -one-o.
contains mainly ethyl alcohol and methylbutenol.
werden im Laufe von 3 Stunden 516 Teile 2-Methylbuten-Acetoacetic ester added all at once. In this mixture is warm.
are in the course of 3 hours 516 parts of 2-methylbutene
Publications (1)
Publication Number | Publication Date |
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DE1068696B true DE1068696B (en) | 1959-11-12 |
Family
ID=593986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT1068696D Pending DE1068696B (en) | Process for the preparation of /, δ-olefinically unsaturated ketones which are branched in the d-position |
Country Status (1)
Country | Link |
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DE (1) | DE1068696B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2371411A1 (en) * | 1976-11-20 | 1978-06-16 | Basf Ag | 2-METHYL-2-HEPTENE-6-ONE PREPARATION PROCESS |
EP0022955A1 (en) * | 1979-07-18 | 1981-01-28 | BASF Aktiengesellschaft | Process for the production of higher unsaturated ketones |
US5874635A (en) * | 1996-11-14 | 1999-02-23 | Basf Aktiengesellschaft | Preparation of γ, δ-unsaturated ketones by the carroll reaction in cyclic carbonates or γ-lactones |
US6828468B2 (en) | 2001-05-11 | 2004-12-07 | Basf Aktiengesellschaft | Preparation of higher α, β-unsaturated alcohols |
-
0
- DE DENDAT1068696D patent/DE1068696B/en active Pending
Non-Patent Citations (1)
Title |
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None * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2371411A1 (en) * | 1976-11-20 | 1978-06-16 | Basf Ag | 2-METHYL-2-HEPTENE-6-ONE PREPARATION PROCESS |
EP0022955A1 (en) * | 1979-07-18 | 1981-01-28 | BASF Aktiengesellschaft | Process for the production of higher unsaturated ketones |
US5874635A (en) * | 1996-11-14 | 1999-02-23 | Basf Aktiengesellschaft | Preparation of γ, δ-unsaturated ketones by the carroll reaction in cyclic carbonates or γ-lactones |
US6828468B2 (en) | 2001-05-11 | 2004-12-07 | Basf Aktiengesellschaft | Preparation of higher α, β-unsaturated alcohols |
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