DE952894C - Process for the production of ethers of 2-methylolbuten-1-ones- (3) - Google Patents

Process for the production of ethers of 2-methylolbuten-1-ones- (3)

Info

Publication number
DE952894C
DE952894C DER14032A DER0014032A DE952894C DE 952894 C DE952894 C DE 952894C DE R14032 A DER14032 A DE R14032A DE R0014032 A DER0014032 A DE R0014032A DE 952894 C DE952894 C DE 952894C
Authority
DE
Germany
Prior art keywords
methylolbuten
ones
ethers
production
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
Application number
DER14032A
Other languages
German (de)
Inventor
Dipl-Chem Dr Walter Grimme
Dipl-Chem Dr Johannes Woellner
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.)
Rheinpreussen AG fuer Bergbau und Chemie
Original Assignee
Rheinpreussen AG fuer Bergbau und Chemie
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rheinpreussen AG fuer Bergbau und Chemie filed Critical Rheinpreussen AG fuer Bergbau und Chemie
Priority to DER14032A priority Critical patent/DE952894C/en
Application granted granted Critical
Publication of DE952894C publication Critical patent/DE952894C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Äthern des 2-Methylolbuten-1-ons-(3) Es wurde gefunden, daß man Äther des 2-Methylolbuten-i-ons-(3) erhält, wenn man 2-Methylolbuteni-on unter Zugabe eines Überschusses an einem aliphatischen Alkohol und einer kleinen Menge einer starken Säure, wie Schwefelsäure, Phosphorsäure oder p-Toluolsulfonsäure, bei erhöhter Temperatur umsetzt. Bei dem konjugiert ungesättigten System des 2-Methylolbuten-i-ons=(3) war es überraschend, daß die Äther auf diese einfache Weise erhalten wurden.Process for the preparation of ethers of 2-methylolbuten-1-ones- (3) It has been found that ether of 2-methylolbuten-i-ones- (3) is obtained if 2-methylolbutenion with the addition of an excess of an aliphatic alcohol and a small amount of a strong acid such as sulfuric acid, phosphoric acid or p-toluenesulfonic acid, reacted at elevated temperature. The conjugated unsaturated one System des 2-Methylolbuten-i-one = (3) it was surprising that the ether on this easy way were obtained.

Die nach dem erfindungsgemäßen Verfahren hergestellten Äther des 2-Methylolbuten-i-ons-(3) dienen zur Herstellung glasklarer Polymerisationsprodukte, die sich auf Grund ihrer Festigkeit und Durchsichtigkeit einerseits als Kunststoffe oder Kunstgläser, wegen ihrer guten Löslichkeit in organischen Lösungsmitteln aber auch als Kunstharze eignen. Beispiel i Zoo g 2-Methylolbuten-(i)-on-(3) werden mit 26o g Methanol vermischt und als Katalysator o,6 g konzentrierte Schwefelsäure hinzugefügt. Die Reaktionsmischung läßt man 15 Stunden unter Rückfluß kochen. Die Innentemperatur der siedenden Reaktionsmischung steigt dabei um einige Grad. Nach beendeter Reaktion neutralisiert man die abgekühlte Mischung mit verdünnter Natronlauge und destilliert im Vakuum. Man erhält nach einem Vorlauf von Methanol den Methyläther des 2-Methylolbuten-(i)-ons-(3) als leicht bewegfiche Flüssigkeit bei 51 bis .52°/r2 nun Iig. D15 = o,959, KP75o= Z52°.The ethers of 2-methylolbuten-i-ones- (3) prepared by the process according to the invention are used for the production of crystal clear polymerization products, which are based on their Strength and transparency on the one hand as plastics or synthetic glasses, because of Their good solubility in organic solvents but also suitable as synthetic resins. Example i Zoo g of 2-methylolbutene- (i) -one- (3) are mixed with 26o g of methanol and 0.6 g of concentrated sulfuric acid was added as a catalyst. The reaction mixture is allowed to reflux for 15 hours. The internal temperature of the boiling reaction mixture increases by a few degrees. After the reaction has ended, the cooled one is neutralized Mixture with dilute sodium hydroxide solution and distilled in vacuo. You get after a First run of methanol the methyl ether of 2-methylolbuten- (i) -one- (3) as easy moveable Liquid at 51 to .52 ° / r2 now Iig. D15 = o.959, KP75o = Z52 °.

Beispiel 2 Zoo g 2-Methylolbuten-(Z)-on-(3) werden mit 26o g Äthanol vermischt und die Mischung mit 1,2 g Toluolsulfonsäure versetzt. Beim Kochen am Rückflut steigt die Temperatur der Mischung auf 84.,5°. Nach 15 Stunden wird abgekühlt und wie im Beispiel Z neutralisiert. Bei der anschließenden Vakuumdestillation erhält man den Äthyläther als Fraktion vom Siedepunkt- 54 bis 55° bei einem .absoluten Druck von 12 mm Hg. DieDichte desÄthers bei Z5° beträgt o,92.5.Example 2 Zoo g of 2-methylolbutene- (Z) -one- (3) are mixed with 260 g of ethanol, and 1.2 g of toluenesulfonic acid are added to the mixture. When boiling at reflux, the temperature of the mixture rises to 84.5 °. After 15 hours, the mixture is cooled and neutralized as in Example Z. In the subsequent vacuum distillation, the ethyl ether is obtained as a fraction with a boiling point of 54 to 55 ° at an absolute pressure of 12 mm Hg. The density of the ether at Z5 ° is 0.92.5.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Äthern des 2-Methylolbuten-Z-ons-(3), dadurch gekennzeichnet, daß man 2-Methylolbuten-Z-on-(3) unter Zugabe eines Überschusses an einem aliphatischen Alkohol und einer kleinen Menge einer starken Säure, wie Schwefelsäure, Phosphorsäure .oder p-Toluolsulfonsäure, bei erhöhter Temperatur umsetzt. Claim: Process for the preparation of ethers of 2-methylolbutene-Z-ones- (3), characterized in that 2-methylolbutene-Z-one- (3) with the addition of an excess of an aliphatic alcohol and a small amount of a strong one Acid, such as sulfuric acid, phosphoric acid or p-toluenesulfonic acid, is converted at an elevated temperature.
DER14032A 1954-04-18 1954-04-18 Process for the production of ethers of 2-methylolbuten-1-ones- (3) Expired DE952894C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER14032A DE952894C (en) 1954-04-18 1954-04-18 Process for the production of ethers of 2-methylolbuten-1-ones- (3)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER14032A DE952894C (en) 1954-04-18 1954-04-18 Process for the production of ethers of 2-methylolbuten-1-ones- (3)

Publications (1)

Publication Number Publication Date
DE952894C true DE952894C (en) 1956-11-22

Family

ID=7399182

Family Applications (1)

Application Number Title Priority Date Filing Date
DER14032A Expired DE952894C (en) 1954-04-18 1954-04-18 Process for the production of ethers of 2-methylolbuten-1-ones- (3)

Country Status (1)

Country Link
DE (1) DE952894C (en)

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