DE817306C - Process for the preparation of 2, 7-dimethylocten- (2) -ol- (7) - Google Patents
Process for the preparation of 2, 7-dimethylocten- (2) -ol- (7)Info
- Publication number
- DE817306C DE817306C DEP39783A DE817306DA DE817306C DE 817306 C DE817306 C DE 817306C DE P39783 A DEP39783 A DE P39783A DE 817306D A DE817306D A DE 817306DA DE 817306 C DE817306 C DE 817306C
- Authority
- DE
- Germany
- Prior art keywords
- dimethylocten
- dimethyloctanediol
- preparation
- parts
- acid
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QSSBJNCYJWNXRU-UHFFFAOYSA-N CC(C(O)O)CCCCC(C)C Chemical compound CC(C(O)O)CCCCC(C)C QSSBJNCYJWNXRU-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XOAUNGGNONXOND-UHFFFAOYSA-N 2,7-dimethylocta-1,3-diene Chemical compound CC(C)CCC=CC(C)=C XOAUNGGNONXOND-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 2, 7-Dimethylocten-(2)-ol-(7) Es wurde gefunden, daß man 2, 7-Dimethylocten-(2)-01-(7) erhalten kann, wenn man 2, 7-Dimethyloctandiol-(2, 7) in der Wärme unter milden Bedingungen mit nicht flüchtigen Säuren behandelt. Das Ausgangsmaterial 2, 7-Dimethyloctandiol-(2, 7) kann man z. B. durch Kondensation von i Mol Acetylen mit i Mol Aceton zum 2-Methylbutin-(3)-01-(2) nach dem Verfahren der Merlingschfn Synthese, Oxydation von 2 Mol 2-Methylbutin-(3)-01-(2) zum 2, 7-Dimethyloctadiin-(3, 5)-diol-(2, 7) (vgl. Chem. Zentralblatt 1937, 1, 4783) oder durch Kondensation von i Mol Diacetylen mit 2 Mol Aceton (vgl. fianz. Patentschrift 890 423) gleichfalls zum 2, 7-Dimethyloctadiin-(3, 5)-diol-(2, 7) und Reduktion des nach dem einen oder anderen Verfahren gewonnenen Diindiols zum 2, 7-Dimethyloctandiol-(2, 7) erhalten.Process for the preparation of 2, 7-dimethylocten- (2) -ol- (7) It has been found that 2, 7-dimethylocten- (2) -01- (7) can be obtained by using 2, 7-dimethyloctanediol - (2, 7) treated warmly under mild conditions with non-volatile acids. The starting material 2, 7-Dimethyloctandiol- (2, 7) can be z. B. by condensation of 1 mole of acetylene with 1 mole of acetone to 2-methylbutyne- (3) -01- (2) according to the method of Merlingschfn synthesis, oxidation of 2 moles of 2-methylbutyne- (3) -01- (2) for 2, 7-dimethyloctadiyne- (3, 5) -diol- (2, 7) (see Chem. Zentralblatt 1937, 1, 4783) or by condensation of 1 mole of diacetylene with 2 moles of acetone (see fianz. Patent 890 423) also to 2,7-dimethyloctadiyne- (3,5) -diol- (2,7) and reduction of the diindiol obtained by one or the other method to 2,7-dimethyloctanediol- (2,7).
Bei der Behandlung des 2, 7-Dimethyloctandiol-(2, 7) in der Wärme unter milden Bedingungen mit nicht flüchtigen Säuren wird i Mol Wasser abgespalten, und man erhält in guter Ausbeute das durch einen angenehmen, blumenartigen Geruch ausgezeichnete 2, 7-Dimethylocten-(2)-01-(7), das z. B. zur Herstellung von Riechstoffmischungen oder als Zwischenprodukt zur Herstellung von Estern, Äthern und anderen Abwandlungsprodukten, die selbst vielfach ebenfalls angenehm riechende Verbindungen sind, verwendet werden kann.When treating the 2, 7-Dimethyloctanediol- (2, 7) in the heat under mild conditions with non-volatile acids, 1 mole of water is split off, and this is obtained in good yield by a pleasant, flower-like odor excellent 2, 7-Dimethylocten- (2) -01- (7), the z. B. for the production of fragrance mixtures or as an intermediate product for the production of esters, ethers and other modification products, which in many cases are also compounds with a pleasant smell themselves, can be used can.
Zur Wasserabspaltung erhitzt man das 2, 7-Dimethyloctandiol-(2, 7) in Gegenwart oder Abwesenheit von Lösungs- oder Verdünnungsmitteln, wie Alkoholen oder Wasser, mit einer nicht flüchtigen Säure, z. B. Schwefelsäure, Phosphorsäure, Benzolsulfonsäure, Toluolsulfonsäure, Phthalsäure, in Mengen bis zu etwa 5% vom eingesetzten 2, 7-Dimethyloctandiol-(2, 7) auf Temperaturen bis zu etwa ioo °. Man vermeidet zu energische Bedingungen, da sonst die Bildung von Nebenprodukten, z. B. des 2, 7-Dimethyloctadien-(2, 6), in den Vordergrund gerückt werden kann.To split off water, the 2, 7-dimethyloctanediol (2, 7) is heated in the presence or absence of solvents or diluents such as alcohols or water, with a non-volatile acid, e.g. B. sulfuric acid, phosphoric acid, Benzenesulfonic acid, toluenesulfonic acid, phthalic acid, in amounts up to about 5% from 2, 7-Dimethyloctanediol- (2, 7) used to temperatures up to about 100 °. Man avoids too energetic conditions, otherwise the Formation of by-products, z. B. des 2, 7-Dimethyloctadien- (2, 6), can be moved to the fore.
Beispiel i Man erhitzt unter Rühren 8 Stunden lang eine Mischung aus ioo Teilen 2. 7-Dimethyloctandiol-(2, 7) und i5o Teilen i°/oiger wäBriger Schwefelsäure auf etwa ioo °. Es scheidet sich ein 01 ab, das bei der Aufarbeitung durch Destillation 6 Teile 2, 7-Dimethyloctadien-(2, 6) vom Kpr45 . 16o°, das einen terpenartigen Geruch besitzt, sowie 72 Teile 2, 7-Dimethylocten-(2)-01-(7) vom Kpi45 . 196' liefert. Beispiel 2 Eine Lösung von i Teil 2, 7-Dimethyloctandiol-(2, 7) in 3 Teilen Butanol, wie sie bei der katalytischen Hydrierung von 2, 7-Dimethyloctadiin-(3, 5)-diol-(2, 7) in Gegenwart von Raney-Nickel erhalten wird, läßt man unter Rühren in einer Menge von 400 g/h zu 5oo g 2°/oiger wäBriger Schwefelsäure zulaufen. Gleichzeitig wird in das Reaktionsgemisch Wasserdampf eingeblasen, der laufend Butanol und das entstandene 2, 7-Dimethylocten-(2)-01-(7) abführt. Das Kondensat der Wasserdampfdestillation trennt sich in zwei Schichten, die untere besteht aus mit Butanol gesättigtem Wasser, aus der oberen Schicht wird nach dem Abdestillieren des Butanols 2, 7-Dimethylocten-(2)-01-(7) in einer Ausbeute von 85°/o gewonnen. Als Nebenprodukt hat sich etwas 2, 7-Dimethyloctadien-(2, 6) gebildet.Example i A mixture of 100 parts of 2,7-dimethyloctanediol (2,7) and 150 parts of 10% aqueous sulfuric acid is heated to about 100 ° for 8 hours while stirring. It separates from an 01 , which in the work-up by distillation 6 parts of 2, 7-dimethyloctadiene (2, 6) from the Kpr45. 16o °, which has a terpene-like odor, and 72 parts 2, 7-Dimethylocten- (2) -01- (7) from the Kpi45. 196 'returns. Example 2 A solution of i part 2, 7-dimethyloctanediol- (2, 7) in 3 parts of butanol, as used in the catalytic hydrogenation of 2, 7-dimethyloctadiyne- (3, 5) -diol- (2, 7) in Is obtained in the presence of Raney nickel, is allowed to run in with stirring in an amount of 400 g / h to 500 g of 2% aqueous sulfuric acid. At the same time, steam is blown into the reaction mixture, which continuously removes butanol and the 2,7-dimethylocten- (2) -01- (7) formed. The condensate of the steam distillation separates into two layers, the lower consists of water saturated with butanol, from the upper layer, after the butanol is distilled off, 2,7-dimethylocten- (2) -01- (7) is produced in a yield of 85 ° / o won. Some 2,7-dimethyloctadiene- (2,6) has formed as a by-product.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE817306T | 1949-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE817306C true DE817306C (en) | 1951-10-18 |
Family
ID=578758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP39783A Expired DE817306C (en) | 1949-04-14 | 1949-04-14 | Process for the preparation of 2, 7-dimethylocten- (2) -ol- (7) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE817306C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1101401B (en) * | 1955-12-13 | 1961-03-09 | Derives Resiniques Terpenique | Process for the production of primary and secondary citronellols |
-
1949
- 1949-04-14 DE DEP39783A patent/DE817306C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1101401B (en) * | 1955-12-13 | 1961-03-09 | Derives Resiniques Terpenique | Process for the production of primary and secondary citronellols |
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