AT60097B - Method for the preparation of homologues of pinacone. - Google Patents
Method for the preparation of homologues of pinacone.Info
- Publication number
- AT60097B AT60097B AT60097DA AT60097B AT 60097 B AT60097 B AT 60097B AT 60097D A AT60097D A AT 60097DA AT 60097 B AT60097 B AT 60097B
- Authority
- AT
- Austria
- Prior art keywords
- homologues
- parts
- pinacone
- preparation
- magnesium
- Prior art date
Links
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 150000002731 mercury compounds Chemical class 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 dimethyl diethyl glycol Chemical compound 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Manufacture And Refinement Of Metals (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Homologen des Pinakons.
Es wurde gefunden, dass sich mit Hilfe von Magnesium unter Zusatz von Quecksilberverbindungen aus den Homologen des Azetons die Homologen des Pinakons erhalten lassen. Während die Darstellung dieser Körper bisher mit Schwierigkeiten verbunden war, entstehen sie nach dieser neuen Darstellungsweise leicht in guter Ausbeute.
B e i s p i e 1 1 : Zn 360 Teilen Magnesiumspäne, die in einem, Rührkessel mit sehr gut wirkendem Rückflusskühler im Wasserbade gelinde erwärmt werden, wird eine Lösung
EMI1.1
dann weitere 1600 Teile Benzol nachgesetzt. Wenn nach einigen Stunden, während welcher Zeit zweckmässig gerührt wird, die Reaktion nachgelassen hat, lässt man die Masse erkalten. Alsdann zersetzt man sie mit 2000 Teilen Eiswasser. Das sich dabei ausscheidende Öl wird abgeschöpft, von der halbfesten Masse abgepresst und im Vakuum fraktioniert.
Das Dimethyldiäthylglykol von der Formel :
EMI1.2
siedet bei 3 mm bei 78 bis 790.
Bei s pie 1 2 : Zu 360 Teilen Magnesiumspäne, die m einem mit Rückflusskühler versehenen Rührkessel gelinde angewärmt werden, werden 40 Teile Kupferchlorür zugesetzt.
Dann wird eine Lösung von 200 Teilen Quecksilberchlorid in 4000 Teilen Methyläthyl- keton einlaufen gelassen. Nach Abklingen der Reaktion, deren Ende sich durch Dickwerden der Masse und Verschwinden des Magnesiums erkennen lässt. wird erkalten gelassen.
Die Aufarbeitung der Reaktionsmasse geschieht wie im Beispiel 1
Aus Diäthylketon entsteht das Tetra. äthylglykol der Formel :
EMI1.3
Es siedet bei 17 mm bei 116 bis 119 und hat nach Umkristallisieren aus Äther den Schmelzpunkt 27 bis 280.
Beispiel 3 : Zu 360 Teilen Magnesitinispäne, die in einem mit Rucknusskühler versehenen Rührkessel gelinde angewärmt sind. wird eine Lösung von 200 Teilen Queck-
EMI1.4
Benzol nachgesetzt. Die Aufarbeitung erfolgt nach Beendigung der Reaktion durch Zersetzen mit 2000 Teilen Eiswasser, wie in vorigen Beispielen angegeben 1st.
Das Dimethyldipropylglykol der Formel :
EMI1.5
siedet bei 15 ins bei 116 bis 1170. Schmelzpunkt 950.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Method for the preparation of homologues of pinacone.
It has been found that the homologues of pinacone can be obtained from the homologues of acetone with the aid of magnesium with the addition of mercury compounds. While the representation of these bodies has so far been associated with difficulties, according to this new representation, they are easily created in good yield.
B e i s p i e 1 1: Zn 360 parts of magnesium shavings, which are gently heated in a water bath in a stirred tank with a very effective reflux condenser, becomes a solution
EMI1.1
then another 1600 parts of benzene were added. When the reaction has subsided after a few hours, during which time it is advisable to stir, the mass is allowed to cool. They are then decomposed with 2000 parts of ice water. The oil that separates out is skimmed off, pressed from the semi-solid mass and fractionated in a vacuum.
The dimethyl diethyl glycol of the formula:
EMI1.2
boils at 3 mm at 78 to 790.
At pie 1 2: 40 parts of copper chloride are added to 360 parts of magnesium shavings, which are gently warmed in a stirred tank equipped with a reflux condenser.
A solution of 200 parts of mercury chloride in 4000 parts of methyl ethyl ketone is then run in. After the reaction has subsided, the end of which can be recognized by the thickening of the mass and the disappearance of the magnesium. is left to cool.
The reaction mass is worked up as in Example 1
Tetra is made from diethyl ketone. ethyl glycol of the formula:
EMI1.3
It boils at 116 to 119 at 17 mm and has a melting point of 27 to 280 after recrystallization from ether.
Example 3: To 360 parts of magnesite chips, which are gently warmed in a stirred tank equipped with a jerk nut cooler. a solution of 200 parts of mercury
EMI1.4
Benzene added. After the reaction has ended, work-up is carried out by decomposition with 2000 parts of ice water, as indicated in the previous examples.
The dimethyldipropylglycol of the formula:
EMI1.5
boils at 15 ins at 116 to 1170. Melting point 950.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE60096X | 1911-03-01 | ||
| DE60097X | 1911-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT60097B true AT60097B (en) | 1913-07-10 |
Family
ID=25749276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT60097D AT60097B (en) | 1911-03-01 | 1912-02-19 | Method for the preparation of homologues of pinacone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT60097B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016993A1 (en) * | 1979-03-14 | 1980-10-15 | Bayer Ag | Substituted tartaric-acid esters, process for their production and their use as polymerization initiators |
-
1912
- 1912-02-19 AT AT60097D patent/AT60097B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016993A1 (en) * | 1979-03-14 | 1980-10-15 | Bayer Ag | Substituted tartaric-acid esters, process for their production and their use as polymerization initiators |
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