DE902494C - Process for the production of ª ‡, ª ‰ -dichlorinated ethers - Google Patents

Process for the production of ª ‡, ª ‰ -dichlorinated ethers

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Publication number
DE902494C
DE902494C DEF2772D DEF0002772D DE902494C DE 902494 C DE902494 C DE 902494C DE F2772 D DEF2772 D DE F2772D DE F0002772 D DEF0002772 D DE F0002772D DE 902494 C DE902494 C DE 902494C
Authority
DE
Germany
Prior art keywords
dichlorinated
ethers
production
mixture
weight
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
DEF2772D
Other languages
German (de)
Inventor
Dr Julius Soell
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to DEF2772D priority Critical patent/DE902494C/en
Application granted granted Critical
Publication of DE902494C publication Critical patent/DE902494C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen

Landscapes

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

Description

Verfahren zur Herstellung von a, ß-dichlorierten Äthern Nach dem Verfahren des Patents 896 342 werden a, ß-dichlorierte Äther dadurch gewonnen, daß man ein Gemisch von Acetaldehyd bzw. Paraldehyd und aliphatischen Alkoholen der Chlorierung unterwirft. Die Reaktion verläuft beispielsweise nach der Gleichung CH, - CHO+CH30H+C12 =CH,Cl-CHC1-O-CH3+H20. An Stelle eines Gemisches der genannten Verbindungen können auch die daraus entstehenden HalbacetaIe benutzt werden. Es wurde nun gefunden, daß sich auf analoge Weise aus anderen Aldehyden die entsprechenden Chlorverbindungen erhalten lassen.Process for the production of α, β-dichlorinated ethers According to the process of patent 896 342, α, β-dichlorinated ethers are obtained by subjecting a mixture of acetaldehyde or paraldehyde and aliphatic alcohols to the chlorination. The reaction proceeds, for example, according to the equation CH, - CHO + CH30H + C12 = CH, Cl-CHC1-O-CH3 + H20. Instead of a mixture of the compounds mentioned, it is also possible to use the hemiacetals formed therefrom. It has now been found that the corresponding chlorine compounds can be obtained in an analogous manner from other aldehydes.

Beispiel i a, ß-Dichlorpropylmethyläther CH3-CHCI-CHCI-O-CH3 In ein Gemisch von 348 Gewichtsteilen Propionaldehyd und 192 Gewichtsteilen Methanol werden in einem Rührgefäß unter Kühlung im Lauf von il/, bis 2 Stunden bei -' 20° 425 g Chlor eingeleitet. Nach dem Abtrennen der wäßrigen Schicht wurde im Vakuum fraktioniert. Physikalische Konstanten: Kpis = 36 bis 38°, Dzo = i,182.Example ia, β-dichloropropyl methyl ether CH3-CHCI-CHCI-O-CH3 In a mixture of 348 parts by weight of propionaldehyde and 192 parts by weight of methanol, 425 g of chlorine are passed in a stirred vessel with cooling in the course of 1 1/2 hours at -20 ° . After the aqueous layer had been separated off, fractionation was carried out in vacuo. Physical constants: Kpis = 36 to 38 °, Dzo = i, 182.

Beispiel 2 a, ß-Dichlorbutylmethyläther CH, -CH2-CHCl-CHC1-O-CH3 In ein Gemisch von 36o Gewichtsteilen Butylaldehyd und 16o g Methanol wurden in einem Rührgefäß unter Kühlung im Lauf von 11,12 bis 2 Stunden bei + Z5 bis 25' 355 g Chlor eingeleitet. Nach dem Abtrennen der wäßrigen Schicht wurde im Vakuum fraktioniert. Physikalische Konstanten: Kp" = 51 bis 53°, Dzo - 1,143. Beispiel 3 a, ß-Dichlorcrotylmethyläther CH3-CH=CCI-CHCI-O-CH3 In ein Gemisch von 28o Gewichtsteilen Crotonaldehyd und z28 Gewichtsteilen Methanol wurden nach Verdünnen mit 200 ccm Methyienchlorid unter Kühlung im Lauf von 1i/2 bis 2 Stunden 284 g Chlor eingeleitet. Gekühlt wurde mit Trockeneis-Aceton auf - 30°. Es entstehen keine zwei Schichten. Das Produkt wurde im Vakuum fraktioniert, wobei das Wasser in den Vorlauf ging. Physikalische Konstanten: K% = 82 bis 84°, Deo = 1,253.Example 2 a, ß-Dichlorobutyl methyl ether CH, -CH2-CHCl-CHC1-O-CH3 In a mixture of 36o parts by weight of butylaldehyde and 160 g of methanol were in a stirred vessel with cooling in the course of 11.12 to 2 hours at + Z5 to 25 '355 g of chlorine initiated. After the aqueous layer had been separated off, fractionation was carried out in vacuo. Physical constants. Kp "= 51 to 53 °, dzo - 1.143 Example 3 a, ß-Dichlorcrotylmethyläther CH3-CH = CCI-CHCl-O-CH3 were after dilution in a mixture of 28o parts by weight of crotonaldehyde and z28 parts by weight of methanol with 200 cc 284 g of chlorine were passed in with cooling in the course of 1½ to 2 hours with methylene chloride. The mixture was cooled to -30 ° with dry ice-acetone. No two layers were formed. The product was fractionated in vacuo, the water going into the flow. Physical Constants: K% = 82 to 84 °, Deo = 1.253.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von a, ß-dichlorierten Äthern nach Patent 896 342, dadurch gekennzeichnet, da.ß an Stelle von Acetaldehyd andere Aldehyde verwendet werden. PATENT CLAIM: Process for the production of α, β-dichlorinated ethers according to patent 896 342, characterized in that other aldehydes are used in place of acetaldehyde.
DEF2772D 1942-11-26 1942-11-26 Process for the production of ª ‡, ª ‰ -dichlorinated ethers Expired DE902494C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF2772D DE902494C (en) 1942-11-26 1942-11-26 Process for the production of ª ‡, ª ‰ -dichlorinated ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF2772D DE902494C (en) 1942-11-26 1942-11-26 Process for the production of ª ‡, ª ‰ -dichlorinated ethers

Publications (1)

Publication Number Publication Date
DE902494C true DE902494C (en) 1954-01-25

Family

ID=7083460

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF2772D Expired DE902494C (en) 1942-11-26 1942-11-26 Process for the production of ª ‡, ª ‰ -dichlorinated ethers

Country Status (1)

Country Link
DE (1) DE902494C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5189227A (en) * 1989-02-02 1993-02-23 Ciba-Geigy Corporation 1,2,4-trihalobutyl ethers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5189227A (en) * 1989-02-02 1993-02-23 Ciba-Geigy Corporation 1,2,4-trihalobutyl ethers

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