AT62283B - Process for the preparation of chlorine derivatives of the amyl series. - Google Patents
Process for the preparation of chlorine derivatives of the amyl series.Info
- Publication number
- AT62283B AT62283B AT62283DA AT62283B AT 62283 B AT62283 B AT 62283B AT 62283D A AT62283D A AT 62283DA AT 62283 B AT62283 B AT 62283B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- amyl
- series
- chlorine
- chlorine derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 title claims description 3
- 125000001309 chloro group Chemical class Cl* 0.000 title 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- CZHLPWNZCJEPJB-UHFFFAOYSA-N 1-chloro-3-methylbutane Chemical group CC(C)CCCl CZHLPWNZCJEPJB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- TXTORVZCRUFBBO-UHFFFAOYSA-N 2,3-dichloro-2-methylbutane Chemical compound CC(Cl)C(C)(C)Cl TXTORVZCRUFBBO-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- NHZZUJIRMHDTKR-UHFFFAOYSA-N carbonic acid;toluene Chemical compound OC(O)=O.CC1=CC=CC=C1 NHZZUJIRMHDTKR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Chlorderivaten der Amylreihe.
Bei der Einwirkung von Chlor auf Trimethyläthy ! en findet nehen einer Chloraddition, welche zu Trunethyläthylenchlorid führt, vorwiegend Bildung von Chloramylenen statt.
Die dabei freiwerdende Salzsäure lagert sich an unverändertes Trimethyläthylen an, so dass auch noch tertiäres Isoamylchlorid gebildet wird. Chlorierungsgemische dieser Zusammensetzung eignen sich aber z. B. nicht zur Darstellung reinen Isoprens, denn bei der Behandlung mit Chlorwasserstoff abspaltenden Mitteln erhält man zufolge der Gegenwart des tertiären Isoamylchlorids ein mit viel Trimethyläthylen verunreinigtes Isopren.
Es wurde nun gefunden, dass sich bei der Einwirkung von Chlor auf Trimethyl- äthylen die Bildung ues tertiären Isoamylchlorids völlig vermeiden lässt, wenn man die Einwirkung unter vermindertem Druck vor sich gehen lässt. Das so entstehende Chlorierungs-
EMI1.1
äthylen, etwa im Verhältnis 2 : 3, einströmen, wobei man den Druck auf etwa 50 mm hält.
Ein Teil des Reaktionsproduktes verdichtet sich schon in dieser Schlange und wird in einer gekühlten Vorlage aufgefangen. Die aus dieser austretenden Dämpfe werden durch Waschen mit Kalkmilch von Salzsäure befreit und in einer mit Kohlensäuretoluolmiscbung gekühlten Vorlage verdichtet. Die Kondensate aus beiden Vorlagen werden vereinigt. Nach Abtrennung von etwa noch vorhandenem. unverandertem Trimethyläthylen besteht das Produkt aus Trimethyläthylenchlorid und Monochloram\ lenen. Dieses Gemisch kann, da diese beiden Verbindungen x. B. nach dem Verfahren des Patentes Nr. 56741) Isopren liefern, ohne weitere Reinigung auf dieses verarbeitet werden.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of chlorine derivatives of the amyl series.
With the action of chlorine on trimethylethy! After a chlorine addition, which leads to methyl ethylenechloride, predominantly formation of chloramylenes takes place.
The hydrochloric acid released in the process accumulates on unchanged trimethylethylene, so that tertiary isoamyl chloride is also formed. Chlorination mixtures of this composition are suitable, for. B. not for the preparation of pure isoprene, because treatment with agents that split off hydrogen chloride gives an isoprene contaminated with a lot of trimethylethylene due to the presence of tertiary isoamyl chloride.
It has now been found that in the action of chlorine on trimethylethylene the formation of tertiary isoamyl chloride can be completely avoided if the action is allowed to proceed under reduced pressure. The resulting chlorination
EMI1.1
Ethylene in a ratio of about 2: 3, keeping the pressure at about 50 mm.
Part of the reaction product is already condensed in this line and is collected in a cooled receiver. The vapors emerging from this are freed from hydrochloric acid by washing with milk of lime and compressed in a receiver cooled with carbonic acid toluene mixture. The condensates from both templates are combined. After separation of any still present. unchanged trimethylethylene, the product consists of trimethylethylene chloride and monochloroamines. This mixture can, since these two compounds x. B. by the method of patent no. 56741) isoprene, can be processed on this without further purification.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE258555T | 1912-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT62283B true AT62283B (en) | 1913-11-25 |
Family
ID=19749899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT62283D AT62283B (en) | 1912-05-30 | 1912-12-12 | Process for the preparation of chlorine derivatives of the amyl series. |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT62283B (en) |
| DE (1) | DE258555C (en) |
| NL (1) | NL372C (en) |
-
1912
- 1912-05-31 DE DE1912258555D patent/DE258555C/en not_active Expired
- 1912-12-12 AT AT62283D patent/AT62283B/en active
- 1912-12-27 NL NL1813A patent/NL372C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL372C (en) | 1914-11-16 |
| DE258555C (en) | 1913-04-12 |
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