DE553177C - Process for the preparation of acetals ª ‡ -ª ‰ -unsaturated aldehydes - Google Patents

Process for the preparation of acetals ª ‡ -ª ‰ -unsaturated aldehydes

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Publication number
DE553177C
DE553177C DESCH89234D DESC089234D DE553177C DE 553177 C DE553177 C DE 553177C DE SCH89234 D DESCH89234 D DE SCH89234D DE SC089234 D DESC089234 D DE SC089234D DE 553177 C DE553177 C DE 553177C
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DE
Germany
Prior art keywords
solvents
unsaturated aldehydes
acetals
preparation
hydroxyl
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
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DESCH89234D
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German (de)
Inventor
Dr Rudolf Schmidt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Schering Kahlbaum AG
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Schering Kahlbaum AG
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Publication date
Application filed by Schering Kahlbaum AG filed Critical Schering Kahlbaum AG
Priority to DESCH89234D priority Critical patent/DE553177C/en
Application granted granted Critical
Publication of DE553177C publication Critical patent/DE553177C/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Darstellung von Acetalen «4-ungesättigter Aldehyde Es ist bekannt, Acetale von gesättigten Aldehyden in der Weise herzustellen, daß man Orthoameisensäureester oder Formimidoäther bzw. deren Quecksilbersalze auf die entsprechenden Carbonylverbindungen bei Gegenwart eines Katalysators und eines hydroxylhaltigen Lösungsmittels einwirken läßt (Berichte 31, S. 101q.). Nach dieser Methode ist es bisher nicht gelungen, solche a-ß-ungesättigten Aldehyde in die zugehörigen Acetale überzuführen, die mit hy droxylhaltigen Lösungsmitteln Additionsverbindungen bilden.Process for the preparation of acetals «4-unsaturated aldehydes Es is known to produce acetals of saturated aldehydes in such a way that one Orthoformic acid esters or formimido ethers or their mercury salts to the corresponding Carbonyl compounds in the presence of a catalyst and a hydroxyl-containing one Lets the solvent act (Reports 31, p. 101q.). According to this method it is so far it has not been possible to convert such a-ß-unsaturated aldehydes into the associated acetals transfer, which form addition compounds with hy droxylhaltigen solvents.

Gemäß Erfindung können Acetale dieser Art jedoch gewonnen werden, wenn man bei dem Verfahren keine Lösungsmittel bzw. nur geringe, lediglich katalytisch wirkende Mengen hydroxylhaltiger Lösungsmittel anwendet oder die Reaktion nur in Gegenwart solcher Lösungsmittel ausführt, die keine Additionsprodukte mit ungesättigten Verbindungen geben können.According to the invention, however, acetals of this type can be obtained, if the process does not use any solvents or only minor ones, only catalytically Acting amounts of hydroxyl-containing solvents applies or the reaction only in The presence of such solvents does not have any addition products with unsaturated Connections can give.

Beispiel z Man läßt 73g Aerolein mit .24o g Orthoameisensäureäthylester, S ccm Alkohol und 4 g Salmiak 5 Tage stehen. Nach dem Abdestillieren des Ameisensäureesters erhält man das Acroleinacetal in sehr guter Ausbeute.Example z 73g of aerolein are mixed with .24o g of ethyl orthoformate, S ccm of alcohol and 4 g of salmiak stand for 5 days. After the formic acid ester has been distilled off the acrolein acetal is obtained in very good yield.

In analoger Weise verfährt man unter Anwendung von Formimidoäther, indem man zu dessen Zersetzung nur die theoretisch erforderlichen Mengen Alkohol bzw. nur einen geringen Überschuß verwendet.In an analogous way one proceeds with the application of formimidoether, by only using the theoretically required amounts of alcohol for its decomposition or only a small excess is used.

Beispiel e 2o9 g Crotonaldehyd werden mit 50o g Orthoameisensäureäthylester und z,5 g KHSOQ einige Tage stehengelassen. Der Katalysator wird durch K2CO3 unwirksam gemacht. Durch fraktionierte Destillation werden 420g Crotonaldehyddiäthylacetal erhalten. Die Ausbeute beträgt 9704 der Theorie.Example e 209 g of crotonaldehyde are left to stand for a few days with 50o g of ethyl orthoformate and about 5 g of KHSOQ. The catalyst is rendered ineffective by K2CO3. 420 g of crotonaldehyde diethyl acetal are obtained by fractional distillation. The yield is 9704 of theory.

Beispiel 3 29o g Crotonaldehyd werden mit 50o g Orthoameisensäureäthylester, 200 g Benzol und 1,5 g Kaliumbisulfat einige Tage stehengelassen. Nach Beendigung der Reaktion wird der Katalysator durch Kaliumcarbonat unwirksam gemacht und die Reaktionsmasse durch fraktionierte Destillation getrennt. Man erhält 420 g Acetal.Example 3 29o g of crotonaldehyde are left to stand for a few days with 50o g of ethyl orthoformate, 200 g of benzene and 1.5 g of potassium bisulfate. After the reaction has ended, the catalyst is rendered ineffective by potassium carbonate and the reaction mass is separated by fractional distillation. 420 g of acetal are obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Aceta--Ien a-ß-ungesättigter Aldehyde durch Einwirkung von Orthoameisensäureestern oder Formimidoäthern bzw. deren Quecksilbersalzen in Gegenwart eines geeigneten Katalysators, dadurch gekennzeichnet, daß man bei solchen a-ß-ungesättigten Aldehyden, die in Gegenwart von Säuren oder Salzen hydroxylhaltige Lösungsmittel addieren, die Reaktion ohne Anwendung von Lösungsmitteln bzw. in Gegenwart nur geringer Mengen hydroxylhaltiger Lösungsmittel ausführt oder daß man Lösungsmittel benutzt, die keine Additionsprodukte mit diesen Verbindungen geben.PATENT CLAIM: Process for the preparation of Aceta - Ien a-ß-unsaturated Aldehydes due to the action of orthoformic acid esters or formimido ethers or their mercury salts in the presence of a suitable catalyst, characterized in that that one with such a-ß-unsaturated aldehydes in the presence of acids or Add salts containing hydroxyl-containing solvents, the reaction without the use of solvents or in the presence of only small amounts of hydroxyl-containing solvents or that one uses solvents which do not have any addition products with these compounds give.
DESCH89234D 1929-02-03 1929-02-03 Process for the preparation of acetals ª ‡ -ª ‰ -unsaturated aldehydes Expired DE553177C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH89234D DE553177C (en) 1929-02-03 1929-02-03 Process for the preparation of acetals ª ‡ -ª ‰ -unsaturated aldehydes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH89234D DE553177C (en) 1929-02-03 1929-02-03 Process for the preparation of acetals ª ‡ -ª ‰ -unsaturated aldehydes

Publications (1)

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DE553177C true DE553177C (en) 1932-06-22

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2465586A (en) * 1939-02-04 1949-03-29 Chromogen Inc Process for producing aldehydes and derivatives thereof
US2626283A (en) * 1953-01-20 Preparation of acrolein acetal
US2678950A (en) * 1954-05-18 Process of producing acrolein
US2691049A (en) * 1954-10-05 Process fob the production of
US2700059A (en) * 1950-02-11 1955-01-18 Distillers Co Yeast Ltd Propene polyethers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2626283A (en) * 1953-01-20 Preparation of acrolein acetal
US2678950A (en) * 1954-05-18 Process of producing acrolein
US2691049A (en) * 1954-10-05 Process fob the production of
US2465586A (en) * 1939-02-04 1949-03-29 Chromogen Inc Process for producing aldehydes and derivatives thereof
US2700059A (en) * 1950-02-11 1955-01-18 Distillers Co Yeast Ltd Propene polyethers

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