DE436999C - Process for the production of chlorine derivatives of ethane - Google Patents
Process for the production of chlorine derivatives of ethaneInfo
- Publication number
- DE436999C DE436999C DEB99024D DEB0099024D DE436999C DE 436999 C DE436999 C DE 436999C DE B99024 D DEB99024 D DE B99024D DE B0099024 D DEB0099024 D DE B0099024D DE 436999 C DE436999 C DE 436999C
- Authority
- DE
- Germany
- Prior art keywords
- ethane
- chlorine
- production
- chlorine derivatives
- methane
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000001309 chloro group Chemical class Cl* 0.000 title 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 239000003610 charcoal Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000001804 chlorine Chemical class 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 13
- 238000005660 chlorination reaction Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
- 229960003750 ethyl chloride Drugs 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008542 thermal sensitivity Effects 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Chlorderivaten des Äthans. Es wurde gefunden, daß sich das Äthan in vorzüglicher Weise chlorieren läßt, wenn man Äthan oder äthanhaltige Gase in Gegenwart von Katalysatoren, zweckmäßig aktiver Kohle, mit Chlor behandelt. Man erhält dabei Äthylehlorid, i # i-Dichlor- und i - i - i-Trichloräthan in wechselnden Mengenverhältnissen; daneben treten bisweilen auch höher chlorierte Ätbanderivate in geringem Maße auf.Process for the production of chlorine derivatives of ethane. It was found that ethane can be chlorinated in an excellent way if ethane is used or ethane-containing gases in the presence of catalysts, expediently active charcoal, treated with chlorine. Ethyl chloride, i # i-dichloro- and i - i - i-trichloroethane are obtained in changing proportions; in addition, there are sometimes also more highly chlorinated ones Etbanderivate to a small extent.
Man hat bereits aus Äthan durch Behandlung mit Chlor bei 3oo bis 55o° ein im wesentlichen aus Äthylchlorid bestehendes Produkt gewonnen, doch ohne Katalysator und unter Anwendung eines beträchtlichen i,berschusses an Äthan. Die Chlorierung des Methans in Gegenwart eines Katalysators, z. B. aktiver Kohle oder aktiver Kieselsäure, erinöglicht es, ohne großen Lberschuß an Äthan und bei wesentlich niedrigeren Temperaturen zu arbeiten, ein Umstand, der nicht nur wegen der thermischen Empfindlichkeit des Äthans und seiner Chlorierungsprodukte, sondern besonders auch wegen der beim Arbeiten mit Chlor und gasförmiger Salzsäure vorhandenen Schwierigkeiten in der Materialfrage von großem Vorteil ist. Auch nach der Erfindung lmtin man bei Wahl geeigneter Arbeitsbedingungen in glatter Weise Produkte erhalten, die im wesentlichen aus Athylchlorid bestehen. Es ist bekannt, Chlorderivate des Methans durch Chlorierung von Methan in Gegenwart von Katalysatoren herzustellen. Es hat sich aber gezeigt, daß bei der Chlor ierung des Äthans wesentlich andere Bedingungen erfüllt werden müssen als bei der Chlorierung des Methans. Während für Methan Reaktionstemperaturen von- 33o bis 8oo° erforderlich sind, erfolgt die Chlorierung des Äthans nach dem neuen Verfahren bereits bei den überraschend niedrigen Temperaturen von ioo bis 300 °. Bei der Chlorierung des Methans muß ferner ein sehr großer Überschuß von Methan verwendet werden, falls man niedrig chlorierte Produkte erhalten will. Auch diese Maßnahme, die die Ausführung der Reaktion erschwert, ist bei dem vorliegenden Verfahren nicht in gleichem Umfange nötig.One has already made of ethane by treatment with chlorine at 300 to 55o ° a product consisting essentially of ethyl chloride obtained, but without a catalyst and using a considerable excess of ethane. The chlorination of methane in the presence of a catalyst, e.g. B. active charcoal or active silica, This is possible without a large excess of ethane and at much lower temperatures to work, a fact that is not only due to the thermal sensitivity of the Ethans and its chlorination products, but especially because of the work with chlorine and gaseous hydrochloric acid existing difficulties in the matter of materials is of great benefit. According to the invention, too, one works with the choice of suitable working conditions smoothly obtained products consisting essentially of ethyl chloride. It is known to produce chlorine derivatives of methane by chlorinating methane in the presence of catalysts. But it has been shown that at the chlorine ation the conditions of ethane have to be met that are significantly different from those of chlorination of methane. While for methane reaction temperatures of -33o to 8oo ° are required are, the chlorination of the ethane takes place according to the new process already with the surprisingly low temperatures of 100 to 300 °. In the chlorination of methane a very large excess of methane must also be used if one is low wants to receive chlorinated products. Also this measure that the execution of the reaction difficult, is not necessary to the same extent in the present method.
Liegt das Äthan, wie in vielen Fällen, so z. B. bei der Gewinnung aus Kohledestillationsgasen, im Gemisch mit Äthylen vor, so ist es zweckmäßig, das Äthylen zuvor in an sich bekannter Weise zu hydrieren und dann das äthylenfreie Gas in der angegebenen Weise mit Chlor zu behandeln. Beispiel i, Ein Gemisch gleicher Raumteile Ät'han und Chlor wird über auf etwa ioo bis 3oo° erhitzte aktive Kohle geleitet. =Ulan erhält etwa gleiche Mengen Äthylchlorid und i # i -Dichloräthan, daneben in geringerem Maße höhere Chlorierungsprodukte, unter diesen r # i - i-Trichloräthan. Die Produkte wer4n in bekannter Weise aus dem abgehenden Gase, das unangegriffenes Äthan und Chlorwasserstoff enthält, abgeschieden.Is the ethane, as in many cases, so z. B. in extraction from coal distillation gases, in a mixture with ethylene, it is expedient to use that To hydrogenate ethylene beforehand in a manner known per se and then the ethylene-free Treat the gas with chlorine in the manner indicated. Example i, a mixture of the same Parts of the volume of ethane and chlorine are mixed with active charcoal heated to about 100 to 300 degrees directed. = Ulan receives about equal amounts of ethyl chloride and i # i-Dichloroethane, besides, to a lesser extent, higher chlorination products, among these r # i - i-trichloroethane. The products are produced in a known manner from the outgoing Gases containing unaffected ethane and hydrogen chloride are separated.
. Beispiel 2.. Example 2.
Das aus einer mit Leuchtgas behandelten aktiven Kohle durch Austreiben gewonnene Gasgemisch, bestehend im wesentlichen aus 4thylen, weniger Äthan, deneben bisweilen auch noch anderen Gasen, wird mit einer dem Äthylengehalt entsprechenden Menge Wasserstoff hydriert. Das Gas wird unter Zugabe von einem Raumteil Chlor auf i1/2 Raumteile Äthan über erhitzte aktive Kohle geführt. Man erhält im wesentlichen Äthylchlorid, daneben weniger i - i-Dichloräthan und nur ganz geringe Mengen höherer Chlorierungsprodukte.That from an active carbon treated with coal gas by expelling it Gas mixture obtained, consisting essentially of 4thylen, less ethane, deneben sometimes also other gases, with a corresponding to the ethylene content Amount of hydrogen hydrogenated. The gas is increased with the addition of one part of the volume of chlorine i1 / 2 parts of the volume of ethane passed over heated active charcoal. Essentially, one obtains Ethyl chloride, next to it less i - i-dichloroethane and only very small amounts of higher Chlorination products.
Ähnlich lassen sich auch andere Katalysatoren, z. B. aktive Kieselsäure, verwenden.Other catalysts, e.g. B. active silica, use.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB99024D DE436999C (en) | 1921-03-30 | 1921-03-30 | Process for the production of chlorine derivatives of ethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB99024D DE436999C (en) | 1921-03-30 | 1921-03-30 | Process for the production of chlorine derivatives of ethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE436999C true DE436999C (en) | 1926-11-11 |
Family
ID=6989529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB99024D Expired DE436999C (en) | 1921-03-30 | 1921-03-30 | Process for the production of chlorine derivatives of ethane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE436999C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006104884A3 (en) * | 2005-03-28 | 2007-03-29 | Shell Oil Co | Conversion of alkylhalides into alcohol alkoxylates |
| US8115039B2 (en) | 2005-03-28 | 2012-02-14 | Shell Oil Company | Catalytic distillation process for primary haloalkanes |
-
1921
- 1921-03-30 DE DEB99024D patent/DE436999C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006104884A3 (en) * | 2005-03-28 | 2007-03-29 | Shell Oil Co | Conversion of alkylhalides into alcohol alkoxylates |
| US8115039B2 (en) | 2005-03-28 | 2012-02-14 | Shell Oil Company | Catalytic distillation process for primary haloalkanes |
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