DE122466C - - Google Patents
Info
- Publication number
- DE122466C DE122466C DENDAT122466D DE122466DA DE122466C DE 122466 C DE122466 C DE 122466C DE NDAT122466 D DENDAT122466 D DE NDAT122466D DE 122466D A DE122466D A DE 122466DA DE 122466 C DE122466 C DE 122466C
- Authority
- DE
- Germany
- Prior art keywords
- citral
- alkali
- solution
- acetone
- pseudojonon
- 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
- 229940043350 citral Drugs 0.000 claims description 12
- 229930007907 citral Natural products 0.000 claims description 12
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 3
- SFEOKXHPFMOVRM-BQYQJAHWSA-N Ionone Chemical compound CC(=O)\C=C\C1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-BQYQJAHWSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000000341 volatile oil Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229930002839 ionones Natural products 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bei der Darstellung von Jonon gemäfs Patent 73089 ist die Darstellung des Zwischenproductes Pseudojonon in folgender Weise abgeändert worden.In the representation of Jonon according to patent 73089, the representation of the intermediate product is The pseudo-jonon has been modified in the following way.
Citral wird, wie F. Tiemann in den Ber. d. deutsch, ehem. Ges. Band 31, Seite 3315 gezeigt hat, beim Schütteln mit einer Lösung von Alkalisulfit vollständig in labile citralhydrosulfonsaure Alkalisalze umgewandelt, wenn man Sorge trägt, dafs das bei dieser Reaction frei werdende Alkalihydrat durch allmähliches Hinzufügen einer Säure oder Einleiten von Kohlensäure oder durch Zusatz eines sauren Salzes sofort gebunden wird. Wenn man die erhaltene noch schwach alkalisch reagirende Lösung von labilen citralhydrosulfonsauren Alkalisalzen mit Aceton versetzt und das Gemisch einige Zeit (4 bis 8 Stunden) erhitzt, so gehen die vorhandenen citralhydrosulfonsauren Alkalisalze in die entsprechenden pseudojononhydrosulfonsauren Alkalisalze über. Aus diesen wird das Pseudojonon durch überschüssiges Alkalihydrat beim Erwärmen in Freiheit gesetzt und kann entweder durch Abheben im Scheidetrichter oder Extraction der schnell abgekühlten Flüssigkeit mit einem Lösungsmittel (Aether, Ligroin u. s. f.) oder durch Destillation der mit einer Säure annähernd neutralisirten Flüssigkeit im Dampfstrom gewonnen werden. Es wird dann nach dem im Haupt-Patent beschriebenen Verfahren weiter in Jonon übergeführt. Citral is, as F. Tiemann in Ber. d. German, formerly Ges. Volume 31, page 3315 shown has, when shaken with a solution of alkali sulfite completely in labile citralhydrosulfonsaure Alkali salts are converted if care is taken that the alkali hydrate released in this reaction is gradually converted Adding an acid or introducing carbon dioxide or by adding an acidic one The salt is bound immediately. If the obtained still reacts weakly alkaline Solution of labile citralhydrosulfonic acid alkali salts are mixed with acetone and the mixture heated for some time (4 to 8 hours), the citralhydrosulfonic acids present go Alkali salts in the corresponding pseudojononhydrosulfonsauren alkali salts. From these the pseudojonon is set free by excess alkali hydrate when heated and can be cooled either by lifting off in the separating funnel or by extraction of the rapidly cooled Liquid with a solvent (ether, ligroin, etc.) or by distillation the liquid, which has been approximately neutralized with an acid, can be obtained in a stream of vapor. It is then further converted into ionon using the method described in the main patent.
ι kg Citral oder die entsprechende Menge irgend eines citralhaltigen Oeles, dessen Gehalt an Citral man vorher mittels einer der bekannten Methoden zur quantitativen Bestimmung des Citrals festgestellt hat, wird mit der Auflösung von 3,5 kg krystallisirten Natriumsulfitsι kg of citral or the corresponding amount of any citral-containing oil, its content to citral one beforehand using one of the known methods for quantitative determination of citral is found with the dissolution of 3.5 kg of crystallized sodium sulfite
(Na2 S O3 + 7 H2 O) (Na 2 S O 3 + 7 H 2 O)
und ι ,25 kg Natriumbicarbonats bezw. der entsprechenden Menge Natriumbisulfrts in 10 kg Wasser bis zur Umwandlung des Citrals in lösliche citralhydrosulfonsaure Natriumsalze geschüttelt. Die durch Abheben im Scheidetrichter von flüssigen Verunreinigungen des Citrals, bezw. von nicht aldehydischen Bestandtheilen der angewendeten citralhaltigen ätherischen OeIe getrennte, noch alkalisch reagirende Flüssigkeit wird mit 0,5 bis 1 kg Aceton, also einem Ueberschufs von Aceton, versetzt und zuerst gelinde, später etwas stärker erhitzt. Nach 6 bis 10 Stunden läfst man erkalten und fügt Natronlauge bis zur stark al-and ι, 25 kg sodium bicarbonate respectively. the corresponding Amount of sodium bisulfite in 10 kg of water until the citral is converted into soluble citralhydrosulfonic acid sodium salts shaken. The by lifting in the separating funnel of liquid impurities of citral, respectively. of non-aldehydic components of the citral-containing essential oils used, which are still alkaline Liquid is mixed with 0.5 to 1 kg of acetone, i.e. an excess of acetone, offset and heated gently at first, later a little more. Allow 6 to 10 hours to cool and adds caustic soda up to the strong al-
*) Früheres Zusatz-Patent 75120..*) Former additional patent 75120 ..
kaiischen Reaction hinzu. Bei gewöhnlicher Temperatur scheidet sich dabei im Wesentlichen nur unverändert gebliebenes Citral ab, welches im Scheidetrichter abgetrennt wird. Erwärmt man danach, so wird auch das Pseudojonon aus den gebildeten labilen pseudojononhydrosulfonsauren Natriumsalzen abgespalten und sammelt sich als Oelschicht über der Salzlösung. Man kühlt schnell ab und gewinnt das abgespaltene Pseudojonon entweder durch Abheben mittels eines Scheidetrichters, bezw. Extraction mit Aether, Ligroin u. s. f. oder indem man die Lösung mit irgend einer Säure annähernd neutralisirt und das Pseudojonon in einem starken Dampfstrom abdestillirt. kaiischen reaction added. At ordinary temperature, this essentially separates only unchanged citral from, which is separated in the separating funnel. If one then heats up, the pseudojonon is also formed from the labile pseudojononhydrosulfonic acids formed Sodium salts split off and collects as an oil layer over the salt solution. You cool off quickly and wins the split off pseudo-jonon either by lifting it off with a separating funnel, respectively Extraction with ether, ligroin, etc., or by treating the solution with any almost neutralized with an acid, and the pseudo-jonon is distilled off in a strong stream of steam.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE122466C true DE122466C (en) |
Family
ID=391383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT122466D Active DE122466C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE122466C (en) |
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0
- DE DENDAT122466D patent/DE122466C/de active Active
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