DE880586C - Process for the preparation of 1, 4-dichlorobutane and 4, 4'-dichlorodibutyl ether - Google Patents
Process for the preparation of 1, 4-dichlorobutane and 4, 4'-dichlorodibutyl etherInfo
- Publication number
- DE880586C DE880586C DEB6516D DEB0006516D DE880586C DE 880586 C DE880586 C DE 880586C DE B6516 D DEB6516 D DE B6516D DE B0006516 D DEB0006516 D DE B0006516D DE 880586 C DE880586 C DE 880586C
- Authority
- DE
- Germany
- Prior art keywords
- dichlorobutane
- preparation
- dichlorodibutyl
- ether
- dichlorodibutyl ether
- 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
- PVBMXMKIKMJQRK-UHFFFAOYSA-N 1-chloro-4-(4-chlorobutoxy)butane Chemical compound ClCCCCOCCCCCl PVBMXMKIKMJQRK-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 title description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- 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
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 1, 4-Dichlorbutan und. 4, 4'-Dichlordibutyläther Gegenstand des Patents 859 734 ist ein Verfahren zur Herstellung von i, 4-Dichlorbutan, bei dem man 2 Mol oder etwas mehr Chlorwasserstoff auf i Mol Tetrahydrofuran, gegebenenfalls in Gegenwart von Katalysatoren, unter erhöhtem Druck bei Temperaturen über 120° einwirken läßt. Als Nebenerzeugnis kann bei diesem Verfahren 4, 4'-Dichlordibutyläther gebildet werden.Process for the preparation of 1, 4-dichlorobutane and. 4,4'-dichlorodibutyl ether The subject of patent 859 734 is a process for the preparation of 1,4-dichlorobutane, in which 2 mol or a little more hydrogen chloride to 1 mol of tetrahydrofuran, optionally in the presence of catalysts, under increased pressure at temperatures above 120 ° can act. 4,4'-dichlorodibutyl ether can be formed as a by-product in this process.
Es wurde nun gefunden, daß man bei dieser Umsetzung höhere Ausbeuten an 4, 4'-Dichlordibutyläther erhält, wenn man auf i Mol Tetrahydrofuran weniger als 2 M01, zweckmäßig aber mehr als i Mol Chlorwasserstoff einwirken läßt. Die Bildung des 4, 4'-Dichlordibutyläthers wird besonders begünstigt, wenn man ohne Katalysator arbeitet und die für die Umsetzung erforderliche Chlorwasserstoffmenge in mehreren Anteilen oder in Form eines langsamen Gasstroms dem unter Druck stehenden heißen Tetrahydrofuran zuführt.It has now been found that this reaction gives higher yields of 4,4'-dichlorodibutyl ether is obtained if one mole of tetrahydrofuran less than 2 M01, but expediently allows more than 1 mol of hydrogen chloride to act. The education of 4, 4'-dichlorodibutyl ether is particularly favored if you do not use a catalyst works and the amount of hydrogen chloride required for the implementation in several Fraction or in the form of a slow gas stream to the pressurized hot Tetrahydrofuran feeds.
Die Ausbeute an 4, 4'-Dichlordibutyläther kann dadurch noch erhöht werden, daß man die Umsetzungstemperatui etwas niedriger als bei dem Verfahren des Hauptpatents, zweckmäßig zwischen 130 und i5o°, wählt; man kann sogar Temperaturen zwischen iop,,und i2o°@ anwenden, doch;.ent_5teht dann ein verhältnismäßighoher@röaeritsatz t-Chlor-4-oxybutan.The yield of 4,4'-dichlorodibutyl ether can thereby be increased still further be that the implementation temperature is slightly lower than in the process of Main patent, expediently between 130 and 150 °, chooses; you can even get temperatures between iop ,, and i2o ° @ use, but; .ent_5teht then a relatively high @ röaeritsatz t-chloro-4-oxybutane.
Beispiel r. .:. . _ In einem emaillierten Eisengefäß von 401 Inhalt, _ .das "innen dünn ausgemauert ist, erhitzt man ,jkg Tetr@h@drofuran auf 14o° und führt im Laufe von 8 Stunden 5 kg Chlorwasserstoff zu. Aus dem Umsetzungsgemisch erhält man durch fraktionierte Destillation 1,7 kg 4, 4'-Diclilordibutyläther, 2,5 kg i, 4-Dichlorbutan und 5,1 kg i-Chlor-4-oxybutan: Beispiel 2 In dem in Beispiel i beschriebenen Gefäß erhitzt man 7 kg Tetrahydrofuran auf 1i5° und führt im Laufe von 8 Stunden 5,5 kg Chlorwasserstoff zu. Aus dem Umsetzungsgemisch erhält man durch fraktionierte Destillation 1,65 kg 4, 4'-Dichlordibutyläther, 435 kg i, 4-Dichlorbutan und 5,3 kg r-Chlor-4-oxybütan. Als @ Vorlauf erhält man Tetrahydrofuran, das aus dem Z-Chlor-4-oxybutan während der Destillation entsteht.Example r. .:. . _ In an enamelled iron vessel with a capacity of 401, which is thinly lined on the inside, jkg Tetr @ h @ drofuran is heated to 140 ° and 5 kg of hydrogen chloride are added over the course of 8 hours. The reaction mixture is obtained by fractional distillation 1.7 kg 4,4'-diclilordibutylether, 2.5 kg i, 4-dichlorobutane and 5.1 kg i-chloro-4-oxybutane: Example 2 In the vessel described in example i, 7 kg tetrahydrofuran are heated to 15 ° and feeds 5.5 kg of hydrogen chloride in the course of 8 hours .. 1.65 kg of 4,4'-dichlorodibutyl ether, 435 kg of i, 4-dichlorobutane and 5.3 kg of r-chloro-4 are obtained from the reaction mixture by fractional distillation -oxybutane: Tetrahydrofuran is obtained as the forerun, which is formed from the Z-chloro-4-oxybutane during the distillation.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB6516D DE880586C (en) | 1939-07-20 | 1939-07-20 | Process for the preparation of 1, 4-dichlorobutane and 4, 4'-dichlorodibutyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB6516D DE880586C (en) | 1939-07-20 | 1939-07-20 | Process for the preparation of 1, 4-dichlorobutane and 4, 4'-dichlorodibutyl ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE880586C true DE880586C (en) | 1953-06-22 |
Family
ID=6954689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB6516D Expired DE880586C (en) | 1939-07-20 | 1939-07-20 | Process for the preparation of 1, 4-dichlorobutane and 4, 4'-dichlorodibutyl ether |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE880586C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113636909A (en) * | 2021-09-16 | 2021-11-12 | 中盐常州化工股份有限公司 | Method for continuously preparing 1, 4-dichlorobutane |
-
1939
- 1939-07-20 DE DEB6516D patent/DE880586C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113636909A (en) * | 2021-09-16 | 2021-11-12 | 中盐常州化工股份有限公司 | Method for continuously preparing 1, 4-dichlorobutane |
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