DE577256C - Process for the preparation of unsaturated ketone alcohols - Google Patents
Process for the preparation of unsaturated ketone alcoholsInfo
- Publication number
- DE577256C DE577256C DEI41547D DEI0041547D DE577256C DE 577256 C DE577256 C DE 577256C DE I41547 D DEI41547 D DE I41547D DE I0041547 D DEI0041547 D DE I0041547D DE 577256 C DE577256 C DE 577256C
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated ketone
- ketone alcohols
- preparation
- alcohols
- dimethylolacetone
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von ungesättigten Ketonalkoholen Es wurde gefunden, daß man auf einfache Weise zu ungesättigten Ketonalkoholen gelangt, wenn man aus mindestens zwei Methylolgruppen im Mölekül enthaltenden Oxyketonen Wasser abspaltet.Process for the preparation of unsaturated ketone alcohols It has been found that unsaturated ketone alcohols can be obtained in a simple manner if from at least two methylol groups in the Mölekül containing oxyketones water splits off.
Geeignete Ausgangsstoffe sind z. B. die nach dem Verfahren des Patents 544 887 erhältlichen Oxyoxoverbindungen sowie die nach dem Verfahren des Patents 575 949 durch Kondensation von Ketonen mit Formaldehyd oder formaldehydabspaltenden Mitteln in neutraler Lösung bei erhöhter Temperatur erhältlichen Produkte.Suitable starting materials are, for. B. the process of the patent 544 887 oxyoxo compounds obtainable as well as those by the method of the patent 575 949 by condensation of ketones with formaldehyde or formaldehyde-releasing agents Agents available in neutral solution at elevated temperature.
Die Wasserabspaltung kann durch Erhitzen der Ausgangsstoffe unter vermindertem Druck in Gegenwart oder Abwesenheit von wasserabspaltenden Mitteln vorgenommen werden. Als wasserabspaltende Mittel kommen z. B. Oxyde, wie Aluminiumoxyd, Säuren, wie Phosphorsäure, oder Salze, wie Aluminiumphosphat, in Betracht. Man vermeidet jedoch zweckmäßig solche wasserabspaltende Verbindungen, die wie Natriummetaborat, Aluminiumchlorid u. dgl. polymerisierend wirken können.The elimination of water can be achieved by heating the starting materials below reduced pressure in the presence or absence of dehydrating agents be made. As dehydrating agents come z. B. Oxides, such as aluminum oxide, Acids, such as phosphoric acid, or salts, such as aluminum phosphate, are suitable. One avoids however, it is advisable to use those dehydrating compounds such as sodium metaborate, Aluminum chloride and the like can have a polymerizing effect.
Die erhaltenen ungesättigten Ketonalkohole können zu mannigfaltigen chemischen Umsetzungen sowie in Form ihrer Polymerisationsprodukte als Ausgangsstoffe in der Lack- und Kunststoffindustrie Verwendung finden. Beispiel r Dimethylolaceton-hergestellt gemäß dem Verfahren des Patents 544887 -, das pro Kilogramm mit 7 cm3 89°1oiger Phosphorsäure versetzt ist, wird im Vakuum bei 16 mm Druck destilliert. Es geht eine nahezu farblose, leicht bewegliche Flüssigkeit über, die der Hauptmenge nach aus 2-Oxymethyl-3-oxobuten-r, 2 von der Formel besteht. Beispiele Das durch Kondensation von Aceton mit Formaldehyd in neutraler Lösung erhältliche Dimethylolaceton liefert unter den im Beispiel z angegebenen Bedingungen ein aus ungesättigten Ketonalkoholen bestehendes Destillat in einer Ausbeute von über 7o % des Ausgangsmaterials.The unsaturated ketone alcohols obtained can be used in a wide variety of chemical reactions and in the form of their polymerization products as starting materials in the paint and plastics industries. Example r Dimethylolacetone, produced according to the process of patent 544887, to which 7 cm3 of 89 ° phosphoric acid per kilogram is added, is distilled in vacuo at 16 mm pressure. An almost colorless, easily mobile liquid passes over, the bulk of which is composed of 2-oxymethyl-3-oxobutene-r, 2 of the formula consists. EXAMPLES The dimethylolacetone obtainable by condensation of acetone with formaldehyde in neutral solution gives under the conditions given in example z a distillate consisting of unsaturated ketone alcohols in a yield of more than 70 % of the starting material.
Beispiel 3 Eine Mischung von Dimethylolaceton mit 8 °/o Aluminiumoxyd ergibt bei der Vakuumdestillation unter 16 mm Druck ein aus ungesättigten Ketonalkoholen bestehendes Destillat in einer Ausbeute von 54 °1o des Ausgangsmaterials. Beispiel ¢ Durch Destillation von Dimethylolmethyläthylketon, das pro Kilogramm einen Zusatz von 84g Aluminiumoxyd erhält, bei Atmosphärendruck entsteht in einer Ausbeute von 70 0A des Ausgangsmaterials ein Gemisch von ungesättigten Ketonalkoholen.EXAMPLE 3 A mixture of dimethylolacetone with 8% aluminum oxide gives, in vacuum distillation under 16 mm pressure, a distillate consisting of unsaturated ketone alcohols in a yield of 54 ° 10 of the starting material. EXAMPLE • By distilling dimethylolmethylethyl ketone, which contains 84 g of aluminum oxide per kilogram, at atmospheric pressure, a mixture of unsaturated ketone alcohols is obtained in a yield of 70 ° of the starting material.
Beispiel 5 Man destilliert Dimethylolaceton, dem pro Kilogramm 5o g Aluminiumphosphat zugesetzt sind, bei 16 mm Druck und erhält den im Beispiel r beschriebenen ungesättigten Ketonalkohol in einer Ausbeute von 56 (Rohprodukt).Example 5 Dimethylolacetone is distilled, which is 5o per kilogram g aluminum phosphate are added, at 16 mm pressure and receives the in example r unsaturated ketone alcohol described in a yield of 56 (crude product).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41547D DE577256C (en) | 1931-05-16 | 1931-05-16 | Process for the preparation of unsaturated ketone alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41547D DE577256C (en) | 1931-05-16 | 1931-05-16 | Process for the preparation of unsaturated ketone alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE577256C true DE577256C (en) | 1933-06-01 |
Family
ID=7190570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI41547D Expired DE577256C (en) | 1931-05-16 | 1931-05-16 | Process for the preparation of unsaturated ketone alcohols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE577256C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE956272C (en) * | 1954-04-17 | 1957-01-17 | Rheinpreussen Ag | Process for the production of crystal clear polymerisation products |
| DE965402C (en) * | 1953-08-04 | 1957-06-06 | Rheinpreussen Ag | Process for the preparation of 2-methylol-3-ketobutene- (1,2) |
-
1931
- 1931-05-16 DE DEI41547D patent/DE577256C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE965402C (en) * | 1953-08-04 | 1957-06-06 | Rheinpreussen Ag | Process for the preparation of 2-methylol-3-ketobutene- (1,2) |
| DE956272C (en) * | 1954-04-17 | 1957-01-17 | Rheinpreussen Ag | Process for the production of crystal clear polymerisation products |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2158616C3 (en) | Process for the production of 3-methyl mercaptopropionaldehyde | |
| EP1567514B1 (en) | Method for producing an aliphatic dialdehyde monoacetal | |
| DE2407675C3 (en) | Process for the separation and recovery of 3-methyl-3-buten-l-ol | |
| DE577256C (en) | Process for the preparation of unsaturated ketone alcohols | |
| EP0040723A1 (en) | Process for a distillative separation of liquid mixtures containing aliphatic alcohols | |
| DE1152393B (en) | Process for the preparation of saturated aliphatic alcohols | |
| DE956948C (en) | Process for the preparation of condensation products from cycloaliphatic ketones and aliphatic aldehydes with at least 2 carbon atoms | |
| DE898895C (en) | Process for the preparation of ª-alkoxypropionaldehyde acetals or their ª-substituted homologues | |
| DE920072C (en) | Process for the rearrangement of cyclic ketoximes | |
| DE892440C (en) | Process for the preparation of substituted glutaraldehyde | |
| DE633595C (en) | Process for the preparation of condensation products of cyclopentanones with aldehydes | |
| DE684431C (en) | Process for the production of capillary-active substances | |
| DE909570C (en) | Process for the production of aldoles | |
| DE1150671B (en) | Process for the production of pure butenols | |
| DE1103031B (en) | Process for the production of polycondensation products from terminally hydroxyl-containing polyethylene glycol ethers and oxygen acids of phosphorus | |
| DE2609566C3 (en) | Process for the preparation of methylheptenone | |
| DE878201C (en) | Process for the production of higher molecular weight condensation products from secondary alcohols | |
| DE734724C (en) | Process for the production of ethers of butanol- (1) -one- (3) | |
| AT228232B (en) | Process for the separation of pure beryllium dialkyls from mixtures which also contain aluminum trialkyls | |
| DE545849C (en) | Process for the production of butyl alcohol | |
| DE2433634C2 (en) | Process for the preparation of 4,4-dimethyl-1,3-dioxane | |
| AT206880B (en) | Process for the production of maleic anhydride | |
| DE927332C (en) | Process for the production of unsaturated cyclic acetals and ketals | |
| DE924897C (en) | Process for the production of plastic masses from mixtures of dicarboxylic acid esters | |
| DE2514762A1 (en) | Utilizing high-boiling residues from isoprene mfr - by decomposition with water over alumina then calcium phosphate catalysts |