US1402337A - Production of halogenated hydrocarbons - Google Patents
Production of halogenated hydrocarbons Download PDFInfo
- Publication number
- US1402337A US1402337A US295473A US29547319A US1402337A US 1402337 A US1402337 A US 1402337A US 295473 A US295473 A US 295473A US 29547319 A US29547319 A US 29547319A US 1402337 A US1402337 A US 1402337A
- Authority
- US
- United States
- Prior art keywords
- ethylene
- chlorine
- production
- pipe
- halogenated hydrocarbons
- 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 - Lifetime
Links
- 150000008282 halocarbons Chemical class 0.000 title description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 17
- 239000005977 Ethylene Substances 0.000 description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 241001289435 Astragalus brachycalyx Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000002917 Fraxinus ornus Nutrition 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Images
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
Definitions
- My invention relates particularly to a process of producinghalogenated hydrocarbons, but has reference especially to the production of ethylene dichloride.
- the figure is a diagrammatic representation partly in section of an apparatus which may be used in accordance with my invention. r Assuming that the process is to be carried out by the treatment of ethylene with chlorine tO L produce. ethylene dichlorlde, ethylene gas may be conveyed by means such as pipe 1 into a chamber such as 1s shown at 2, This is preferably formed by a co erplate 3, which is shown as secured to a cylin drical casing 4, in such a manner as to hold 1 between the cover plate 3 and the cylinder 4 a perforated plate 5, carrying in the same Specification of Letters Patent.
- Chlorine gas is preferably admitted to the chamber 2 by means such as a pipe 12 in the proportion of ten volumes of chlorine to eleven volumes of ethylene, these proportions being chosen so as to maintain at all times throughout the treatment an excess of ethylene present.
- the chlorine and ethylene after entering the chamber 2 pass downwardly through the tubes 6, where they become united to form ethylene dichloride, the temperature being kept low at all times by means of e. g., the current of water in the cylinder 4.
- the ethylene dichloride together with some chlorine dissolved therein, and some gaseous ethylene, pass out of the chamber 9 by means such as a pipe 13 and into a receiver 14, where the pipe 13 preferably terminates as near the bottom 'of the re
- the gaseous ethylene which descends in the pipe 13 will be bubbled through the liquid in the receiver 14, so as to combine with all the chlorine which is dissolved in the liquid, so that in this manner ethylene dichloride entirely free from any *uncombined chlorine is obtained, and may bev drawn ofi from time to time through a valved pipe 15 in the bottom of the receiver.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
. p gpsg'z I Patented Jan. 3, 19220 A. A. BACKHAUS.
PRODUCTION OF HALOGENATED HYDROCARBONS. APPLICATION FILED MAY 7, 1919.
cam "mm ARTHUR A. BACKHAUS OF BALTIMORE, MARYLAND, ASSIGNOR TO U. S. INDUSTBIAL' Parser cr tics.
ALCOHOL CO A CORPORATION OF WEST manna.
PRODUCTION OF HALOGENATED HYDBOCABBONS.
Application filed may 7,
' To all whom it may concern:
specification.
My invention relates particularly to a process of producinghalogenated hydrocarbons, but has reference especially to the production of ethylene dichloride.
The object of my invention is to provide a'process by means of which unsaturated hydrocarbons may be halogenated by addition rather than substitution, and especially by means of which process ethylene dichloride may be made from ethylene in an advantageous manner and with a high yield. Further objects of my invention are to provide a process of the above character which is operated with the exclusion of light, the maintenance of an excess of the unsaturated hydrocarbomsuch for example as ethylene, throughout the treatment, and the maintenance of a comparatively low temperature during the treatment.
Further objects of my invention will appear from the detailed description thereof the ends of a series of tubes 6. These are out of iron. The temperatureis' k set forth hereinafter.
While my invention is capable of being carried out in many different ways, for the purpose of illustration'I shall describe only certain ways of carrying out the same hereinafter, and while it is capable of being carried out in connection with many differenttypes of apparatus, -I have shown only one type of apparatus for use in connection therewith in the accompanying drawings, in which; 1
The figure is a diagrammatic representation partly in section of an apparatus which may be used in accordance with my invention. r Assuming that the process is to be carried out by the treatment of ethylene with chlorine tO L produce. ethylene dichlorlde, ethylene gas may be conveyed by means such as pipe 1 into a chamber such as 1s shown at 2, This is preferably formed by a co erplate 3, which is shown as secured to a cylin drical casing 4, in such a manner as to hold 1 between the cover plate 3 and the cylinder 4 a perforated plate 5, carrying in the same Specification of Letters Patent.
Patented Jan. 3, 1922.
1919. Serial No. 295,473.
. shown as held in place in a similar manner at their lower ends by means of a perforated plate 7, located between the cylinder 4 and a bottom plate 8, which form a chamber 9 atthe lower end of the apparatus. The cylinder 4 is kept cool by means such as a counter-current of water which is admitted by a pipe 10, and-which flows out of the cylinder 4 by means of a pipe 11. Chlorine gas is preferably admitted to the chamber 2 by means such as a pipe 12 in the proportion of ten volumes of chlorine to eleven volumes of ethylene, these proportions being chosen so as to maintain at all times throughout the treatment an excess of ethylene present. In this embodiment the chlorine and ethylene after entering the chamber 2 pass downwardly through the tubes 6, where they become united to form ethylene dichloride, the temperature being kept low at all times by means of e. g., the current of water in the cylinder 4. The ethylene dichloride together with some chlorine dissolved therein, and some gaseous ethylene, pass out of the chamber 9 by means such as a pipe 13 and into a receiver 14, where the pipe 13 preferably terminates as near the bottom 'of the re ceiver as possible, so as to form a liquid seal within the receiver. The liquid within the solved therein. As the process continues to 'be carried out, the gaseous ethylene which descends in the pipe 13 will be bubbled through the liquid in the receiver 14, so as to combine with all the chlorine which is dissolved in the liquid, so that in this manner ethylene dichloride entirely free from any *uncombined chlorine is obtained, and may bev drawn ofi from time to time through a valved pipe 15 in the bottom of the receiver.
In this embodiment the excess of the ethylene passes out of the receiver 14 by means such as a pipe 16, preferably which conductsthe ethylene back to the chamber 2, where the ethylene is thus again brought into contact with chlorine, so as to form. ethylene dichloride in the same manner as previously described. v 1
It will be understood that .all of the apparatus above described is ordinarily made of anopaque material of such a character as not to be acted upon by the substance prescut, and may for example be mad 4 "nighas ow as possible, and in any event "as low as 50 (3., as indicated by the temperature .in the materials flowing out of the chamber 9.- By
excluding the light and keeping the temperature as low as possible, very high yields are obtained, that is to say 96 and 97% of theethylene treated is changed to ethylene dichloride, inasmuch as in this manner substitution of hydrogen atoms by the halogen used is obviated. Furthermore, it will be understood that instead of ethylene other unsaturated hydrocarbons may be used, as for example butylene or amylene, and that instead of the chlorine the other halogens may be used. 1
.While I have described my invention above in,detail, I wish it to be understood that many changes may be made therein without departing from the spirit thereof.
I claim:
1. The process of forming pure olefine dihalide comprising passing a halogen and olefine through cooled tubes in av continuous olefine through .the dihalide formed, bubbling the halogen stream, collecting the dihalide, bubbling said stream 'therethrough, and continually returning the uncombined gas to the stream entering the tubes 2. The process of halide comprising passing the halogen and cooled tubes and collecting and olefine through the dihalide formed, and returning the uncombined'halogen-and olefine to the entrance of the tubes,
3. The process of forming pure ethylene dichloride comprising passing chlorine and ethylene through cooled tubes and collecting forming'pureolefine dithe ethylene dichloride formed, bubbling the chlorine and ethylene through said ethylene dichloride, and returning the 'uncombined ethylene and chlorine to theentrance of the tubes.
' In testimony that I claim the foregoing, I
have hereunto set my hand this 22n day of April, 1919. v i p ARTHUR A. BACKHAUS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US295473A US1402337A (en) | 1919-05-07 | 1919-05-07 | Production of halogenated hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US295473A US1402337A (en) | 1919-05-07 | 1919-05-07 | Production of halogenated hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1402337A true US1402337A (en) | 1922-01-03 |
Family
ID=23137869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US295473A Expired - Lifetime US1402337A (en) | 1919-05-07 | 1919-05-07 | Production of halogenated hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1402337A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788358A (en) * | 1979-06-01 | 1988-11-29 | Bayer Aktiengesellschaft | Process for the manufacture of 1,2-dichloroethane |
| US20070025889A1 (en) * | 2005-07-28 | 2007-02-01 | Pcbu Business Services, Inc. | Reactors, reactor assemblies and production processes |
-
1919
- 1919-05-07 US US295473A patent/US1402337A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788358A (en) * | 1979-06-01 | 1988-11-29 | Bayer Aktiengesellschaft | Process for the manufacture of 1,2-dichloroethane |
| US20070025889A1 (en) * | 2005-07-28 | 2007-02-01 | Pcbu Business Services, Inc. | Reactors, reactor assemblies and production processes |
| WO2007015827A3 (en) * | 2005-07-28 | 2007-12-21 | Great Lakes Chemical Corp | Reactors, reactor assemblies, and production processes |
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