CA2195558A1 - Process and device for preparing 1,2-dichloroethane by direct chlorination with waste gas recirculation - Google Patents
Process and device for preparing 1,2-dichloroethane by direct chlorination with waste gas recirculationInfo
- Publication number
- CA2195558A1 CA2195558A1 CA002195558A CA2195558A CA2195558A1 CA 2195558 A1 CA2195558 A1 CA 2195558A1 CA 002195558 A CA002195558 A CA 002195558A CA 2195558 A CA2195558 A CA 2195558A CA 2195558 A1 CA2195558 A1 CA 2195558A1
- Authority
- CA
- Canada
- Prior art keywords
- edc
- reaction
- chloride
- ethylene
- pressure
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
- C07C19/043—Chloroethanes
- C07C19/045—Dichloroethanes
-
- 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)
Abstract
The invention concerns a process for preparing 1,2-dichloroethane (EDC) by feeding chlorine and ethylene into circulated EDC which contains a catalyst. A partial stream of the reaction mixture is fed to a flash vaporization system and the vaporized EDC is separated from its light volatile components which are returned to the reaction.
Description
2 ~ 9 5 5 5 8 t~ r~
WO 96/03361 ~E~T ~ ~ PCT/EP95/02787 Description Process and apparatus for preparing 1,2-dichloroethane by direct chlorination with o~-gas recycling The i~vention relates to a process for preparing 1,2-dichloroethane, termed "EDC" below, by ieeding chlorine and ethylene into circulated EDC which contains a cata-lyst system of iron(III) chloride and a halide o~ a metal of the first or second main group o~ the Periodic Table of the Elements and small amounts o~ oxygen, a part-stream of the reaction mixture being ~ed to ~lash evaporation, the vaporized EDC being separated o~i ~rom more readily volatile constituents and isolated, which comprises returning said more readily volatile constitu-ents to the reaction, the combination of the followingprocess features being excepted: the metal chloride in the catalyst system is sodium chloride, the molar ratio of sodium chloride to iron(III) chloride r ;n;n5 below 0.5 during the entire reaction, the ~lash evaporation proceeds in a vessel under reduced pressure and ethylene-containing oi~-gaa is recycled to the reaction by a compressor.
The process ~or preparing EDC by reaction o~ chlorine and ethylene is known under the term "direct chlorination~.
Thus, ~or example, DE-A 41 33 810 relates to such a process in which the enthalpy of reaction is utilized with the aid o~ flash evaporation. This known procesa is carried out at a temperature o~ about 75 to 200~C and a pressure o~ about 1 to 15 bar.
A procesa has also already been proposed ~or preparing EDC by reaction o~ ethylene with chlorine over a sodium chloride/iron(III) chloride catalyst a ~eature o~ which i8 that the molar ratio o~ sodium chloride to iron(III) chloride remains below 0.5 during the entire reaction.
This process is pre~erably carried out at 50 to 105~C and 2 1 9~558 at a pres~ure of up to 1 bar gauge pressure. In a further preferred embodiment, all or part o~ the EDC i9 paased into a vessel under reduced pressure, the product distilling off being sQparated off and the L-. i n; ng EDC
being recycled to the process. Aa an expedient design, it is further proposed, to decrease the ethylene losses, to recycle the ethylene-c~n~;n;ng o~f-gas from the flash vessel downstream o~ the vacuum pump (which is n~cess~ry to maintain the reduced pressure in the ~lash vessel~ to the reaction by means of a suitable compressor, prefer-ably a li~uid-jet compressor, which is expediently mounted on the bottom of the reactor, and to react the ethylene with chlorine again. In this case, a part-stream of the EDC circulated by pumping advantageously serves as motive jet for the preferred compre330r (German Patent Application P 43 18 609.2 of 04.06.1993).
The proce33 according to the invention is extraordinarily ver3atile: the reaction can proceed in a temperature range from about 50 to 200~C and at a pre3sure from about 1 to about 15 bar gauge pressure. The pressure in the fla3h vessel must be correspondingly lower and is in the range from 0.2 to 3.5 bar absolute. In one embodiment of the procesa, this pressure in the flash vessel i9 more than 0.7 bar absolute.
The metal halide in the catalyst system is preferably lithium chloride, potassium chloride or magnesium chlor-ide and in particular sodium chloride. The molar ratio o~
metal halide and iron(III) chloride can vary within certain limits and in the known proces3es is between 0.5 : 1 and 2 : 1 (N~-A 6901398, DE-A 41 03 281).
The chlorine used can be ~ed in the liquid or gaseous state. It is ~ot even necessary to use chlorine of the highest quality grade: as a result of a suitable choice of compressor, ~or example using the liquid-jet compressor mentioned in the proposed process, a te~n;~l grade chlorine which contains small amounts of oxygen can _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ . _ _ _ _ _ . . .
_ 3 _ 2 1 9 555 8 be uGed. Another possibility i9 the use of a compressor of a different type which is appropriately explosion-proof and resistant to pressure pulses.
If a liquid-jet compressor is selected, in the process 5- according to the invention a part-stream of the EDC
circulated by pumping also preferably serves as motive jet, in particular a part-stream of the EDC recycled to the reactor and preferably cooled.
The process according to the invention is advantageously carried out in an apparatus coLLe~v~ding to the Figure.
This apparatus contains a reactor (1), feed lines (2) and (3) ior ethylene and chlorine respec-tively and preferably (4) for an inert gas, a line (5) to the flash vessel (6) which is under reduced pressure and has a line (7) to conduct away the vaporized product and a line (8) for recycling the nonvaporized product, to which is preferably connected a dissolving vessel (9) and which preierably runs via a pump (10), a line (11) for recycling a product part-stream, which preferably runs via a pump (12) and a cooler or heat exchanger (13).
The line (7) for the EDC vapor expediently runs via a cooler (14) to the vacuum pump (15). From the cooler (14), the line (16~ runs to the receiving vessel (17) for the liquefied EDC.
The apparatus further contains a line (18) from the (pressure side of the) vacuum pump (15) via the com-pressor (19) to the reactor (1) for recycling residual amounts of unreacted ethylene. (20) and (21~ are lines for off-gas di~posal.
The invention is described in more detail in the example ~ _ 4 _ 2 1 95558 below.
Example For direct chlorination, a reactor (1) having a volume of 14.6 m3 was fed with 3000 m3 (S.T.P)/h of ethylene via the line (2). Via the line (3), the equivalent chlorine stream was fed in. The preasure was kept at 0.8 bar gauge pressure via the line (4) with nitrogen and the tempera-ture was kept at 90~C. ~iquid EDC having an iron(ITI) chloride content of 780 ppm served as reaction medium.
Via the dis~olving ves~el (9), sufficient sodium chloride was metered into the reaction medium until the desired concentration of about 170 ppm was reached and L~ ;no~
constant.
A product part-stream was conducted via the line (5) into the downstream fla~h vessel (6) at a pressure of 0.7 to 0.8 bar absolute. ~ere, 13.3 t of EDC were vaporized per hour and taken off via the line (7). This EDC was free of catalyst and had a purity of 99.92%.
The EDC not vaporized in the flash vessel (6) was recycled into the reactor (1) via the line (8) and the pump (10). The main product stream was fed into the line (8) via the line (11) and the pump (12) and recycled to the reactor (1) via the cooler (13).
A stream of 50 m3 (S.T.P.)/h having an ethylene content of 6% by volume were fed to co~bustion via the off-gas line (21). This corresponds to an ethylene loss of 3 m3 (S.T.P.)/h. The off-gas line (20) was closed.
In contrast, if via the off-gas line (21) a stream of 28 m3 (S.T.P.)/h having an ethylene content of 6~ by volume and via the off-gas line ~20) a stream of 26 m3 (S.T.P.)/h having an ethylene content of 16~ by volume is fed to combustion, that c~,,e~ds in total to an .. . . . . .
~ ~ f 9~558 ethylene 105s 0~ 5.9 m3 (S.T.P.)/h or 2.9 m3 (S.T.P.)~h more than by the procedure according to the inve~tio~.
The process according to the invention with closed o~-gas li~e (20) and recycling o~ the gas stream via the line (18) thus virtually halves the ethylene le88 to about 0.1% of the amou~t o~ ethylene used.
WO 96/03361 ~E~T ~ ~ PCT/EP95/02787 Description Process and apparatus for preparing 1,2-dichloroethane by direct chlorination with o~-gas recycling The i~vention relates to a process for preparing 1,2-dichloroethane, termed "EDC" below, by ieeding chlorine and ethylene into circulated EDC which contains a cata-lyst system of iron(III) chloride and a halide o~ a metal of the first or second main group o~ the Periodic Table of the Elements and small amounts o~ oxygen, a part-stream of the reaction mixture being ~ed to ~lash evaporation, the vaporized EDC being separated o~i ~rom more readily volatile constituents and isolated, which comprises returning said more readily volatile constitu-ents to the reaction, the combination of the followingprocess features being excepted: the metal chloride in the catalyst system is sodium chloride, the molar ratio of sodium chloride to iron(III) chloride r ;n;n5 below 0.5 during the entire reaction, the ~lash evaporation proceeds in a vessel under reduced pressure and ethylene-containing oi~-gaa is recycled to the reaction by a compressor.
The process ~or preparing EDC by reaction o~ chlorine and ethylene is known under the term "direct chlorination~.
Thus, ~or example, DE-A 41 33 810 relates to such a process in which the enthalpy of reaction is utilized with the aid o~ flash evaporation. This known procesa is carried out at a temperature o~ about 75 to 200~C and a pressure o~ about 1 to 15 bar.
A procesa has also already been proposed ~or preparing EDC by reaction o~ ethylene with chlorine over a sodium chloride/iron(III) chloride catalyst a ~eature o~ which i8 that the molar ratio o~ sodium chloride to iron(III) chloride remains below 0.5 during the entire reaction.
This process is pre~erably carried out at 50 to 105~C and 2 1 9~558 at a pres~ure of up to 1 bar gauge pressure. In a further preferred embodiment, all or part o~ the EDC i9 paased into a vessel under reduced pressure, the product distilling off being sQparated off and the L-. i n; ng EDC
being recycled to the process. Aa an expedient design, it is further proposed, to decrease the ethylene losses, to recycle the ethylene-c~n~;n;ng o~f-gas from the flash vessel downstream o~ the vacuum pump (which is n~cess~ry to maintain the reduced pressure in the ~lash vessel~ to the reaction by means of a suitable compressor, prefer-ably a li~uid-jet compressor, which is expediently mounted on the bottom of the reactor, and to react the ethylene with chlorine again. In this case, a part-stream of the EDC circulated by pumping advantageously serves as motive jet for the preferred compre330r (German Patent Application P 43 18 609.2 of 04.06.1993).
The proce33 according to the invention is extraordinarily ver3atile: the reaction can proceed in a temperature range from about 50 to 200~C and at a pre3sure from about 1 to about 15 bar gauge pressure. The pressure in the fla3h vessel must be correspondingly lower and is in the range from 0.2 to 3.5 bar absolute. In one embodiment of the procesa, this pressure in the flash vessel i9 more than 0.7 bar absolute.
The metal halide in the catalyst system is preferably lithium chloride, potassium chloride or magnesium chlor-ide and in particular sodium chloride. The molar ratio o~
metal halide and iron(III) chloride can vary within certain limits and in the known proces3es is between 0.5 : 1 and 2 : 1 (N~-A 6901398, DE-A 41 03 281).
The chlorine used can be ~ed in the liquid or gaseous state. It is ~ot even necessary to use chlorine of the highest quality grade: as a result of a suitable choice of compressor, ~or example using the liquid-jet compressor mentioned in the proposed process, a te~n;~l grade chlorine which contains small amounts of oxygen can _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ . _ _ _ _ _ . . .
_ 3 _ 2 1 9 555 8 be uGed. Another possibility i9 the use of a compressor of a different type which is appropriately explosion-proof and resistant to pressure pulses.
If a liquid-jet compressor is selected, in the process 5- according to the invention a part-stream of the EDC
circulated by pumping also preferably serves as motive jet, in particular a part-stream of the EDC recycled to the reactor and preferably cooled.
The process according to the invention is advantageously carried out in an apparatus coLLe~v~ding to the Figure.
This apparatus contains a reactor (1), feed lines (2) and (3) ior ethylene and chlorine respec-tively and preferably (4) for an inert gas, a line (5) to the flash vessel (6) which is under reduced pressure and has a line (7) to conduct away the vaporized product and a line (8) for recycling the nonvaporized product, to which is preferably connected a dissolving vessel (9) and which preierably runs via a pump (10), a line (11) for recycling a product part-stream, which preferably runs via a pump (12) and a cooler or heat exchanger (13).
The line (7) for the EDC vapor expediently runs via a cooler (14) to the vacuum pump (15). From the cooler (14), the line (16~ runs to the receiving vessel (17) for the liquefied EDC.
The apparatus further contains a line (18) from the (pressure side of the) vacuum pump (15) via the com-pressor (19) to the reactor (1) for recycling residual amounts of unreacted ethylene. (20) and (21~ are lines for off-gas di~posal.
The invention is described in more detail in the example ~ _ 4 _ 2 1 95558 below.
Example For direct chlorination, a reactor (1) having a volume of 14.6 m3 was fed with 3000 m3 (S.T.P)/h of ethylene via the line (2). Via the line (3), the equivalent chlorine stream was fed in. The preasure was kept at 0.8 bar gauge pressure via the line (4) with nitrogen and the tempera-ture was kept at 90~C. ~iquid EDC having an iron(ITI) chloride content of 780 ppm served as reaction medium.
Via the dis~olving ves~el (9), sufficient sodium chloride was metered into the reaction medium until the desired concentration of about 170 ppm was reached and L~ ;no~
constant.
A product part-stream was conducted via the line (5) into the downstream fla~h vessel (6) at a pressure of 0.7 to 0.8 bar absolute. ~ere, 13.3 t of EDC were vaporized per hour and taken off via the line (7). This EDC was free of catalyst and had a purity of 99.92%.
The EDC not vaporized in the flash vessel (6) was recycled into the reactor (1) via the line (8) and the pump (10). The main product stream was fed into the line (8) via the line (11) and the pump (12) and recycled to the reactor (1) via the cooler (13).
A stream of 50 m3 (S.T.P.)/h having an ethylene content of 6% by volume were fed to co~bustion via the off-gas line (21). This corresponds to an ethylene loss of 3 m3 (S.T.P.)/h. The off-gas line (20) was closed.
In contrast, if via the off-gas line (21) a stream of 28 m3 (S.T.P.)/h having an ethylene content of 6~ by volume and via the off-gas line ~20) a stream of 26 m3 (S.T.P.)/h having an ethylene content of 16~ by volume is fed to combustion, that c~,,e~ds in total to an .. . . . . .
~ ~ f 9~558 ethylene 105s 0~ 5.9 m3 (S.T.P.)/h or 2.9 m3 (S.T.P.)~h more than by the procedure according to the inve~tio~.
The process according to the invention with closed o~-gas li~e (20) and recycling o~ the gas stream via the line (18) thus virtually halves the ethylene le88 to about 0.1% of the amou~t o~ ethylene used.
Claims (3)
1. A process for preparing 1,2-dichloroethane (EDC) by feeding chlorine and ethylene into circulated EDC
which contains a catalyst system of iron(III) chloride and a halide of a metal of the first or second main group of the Periodic Table of the Elements and small amounts of oxygen, a part-stream of the reaction mixture being fed to flash evaporation, the vaporized EDC being separated off from more readily volatile constituents and isolated, which comprises returning said more readily volatile constituents to the reaction, the combination of the following process features being excepted: the metal chloride in the catalyst system is sodium chloride, the molar ratio of sodium chloride to iron(III) chloride remaining below 0.5 during the entire reaction, the flash evaporation proceeds in a vessel under reduced pressure and ethylene-containing off-gas is recycled to the reaction by a compressor.
which contains a catalyst system of iron(III) chloride and a halide of a metal of the first or second main group of the Periodic Table of the Elements and small amounts of oxygen, a part-stream of the reaction mixture being fed to flash evaporation, the vaporized EDC being separated off from more readily volatile constituents and isolated, which comprises returning said more readily volatile constituents to the reaction, the combination of the following process features being excepted: the metal chloride in the catalyst system is sodium chloride, the molar ratio of sodium chloride to iron(III) chloride remaining below 0.5 during the entire reaction, the flash evaporation proceeds in a vessel under reduced pressure and ethylene-containing off-gas is recycled to the reaction by a compressor.
2. The process as claimed in claim 1, wherein the reaction proceeds at a temperature of about 50 to 200°C and at a pressure of about 1 to about 15 bar gauge pressure.
3. The process as claimed in claim 2, wherein the flash evaporation proceeds at a pressure of 0.2 to 3.5 bar absolute.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4425872.0 | 1994-07-21 | ||
| DE4425872A DE4425872A1 (en) | 1994-07-21 | 1994-07-21 | Process and device for producing 1,2-dichloroethane by direct chlorination with exhaust gas recirculation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2195558A1 true CA2195558A1 (en) | 1996-02-08 |
Family
ID=6523805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002195558A Abandoned CA2195558A1 (en) | 1994-07-21 | 1995-07-15 | Process and device for preparing 1,2-dichloroethane by direct chlorination with waste gas recirculation |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0772576B1 (en) |
| JP (1) | JPH10502932A (en) |
| KR (1) | KR970704650A (en) |
| CN (1) | CN1152903A (en) |
| AU (1) | AU693583B2 (en) |
| BG (1) | BG101140A (en) |
| BR (1) | BR9508311A (en) |
| CA (1) | CA2195558A1 (en) |
| CZ (1) | CZ11297A3 (en) |
| DE (2) | DE4425872A1 (en) |
| FI (1) | FI970216A (en) |
| HU (1) | HUT77001A (en) |
| MX (1) | MX9700531A (en) |
| MY (1) | MY131780A (en) |
| NO (1) | NO970237D0 (en) |
| PL (1) | PL318316A1 (en) |
| SK (1) | SK6297A3 (en) |
| WO (1) | WO1996003361A1 (en) |
| ZA (1) | ZA956058B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW442449B (en) | 1996-07-04 | 2001-06-23 | Hoechst Ag | Process for preparing 1,2-dichloroethane by direct chlorination |
| DE10050315C2 (en) | 2000-10-10 | 2003-08-21 | Uhde Gmbh | Process for dissolving salts in 1,2-dichloroethane by means of ultrasound and device for carrying out the process |
| JP2006335665A (en) * | 2005-05-31 | 2006-12-14 | Tokuyama Corp | Method for producing 1,2-dichloroethane |
| CN104209128A (en) * | 2013-05-29 | 2014-12-17 | 上海氯碱化工股份有限公司 | Composite catalyst for direct chlorination reaction to prepare dichloroethane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075742B1 (en) * | 1981-09-21 | 1984-11-07 | Hoechst Aktiengesellschaft | Process for the preparation of 1,2-dichloroethane |
| DE4318609A1 (en) * | 1993-01-27 | 1994-07-28 | Hoechst Ag | Process and device for producing 1,2-dichloroethane by direct chlorination |
-
1994
- 1994-07-21 DE DE4425872A patent/DE4425872A1/en not_active Withdrawn
-
1995
- 1995-07-15 CN CN95194121A patent/CN1152903A/en active Pending
- 1995-07-15 DE DE59504920T patent/DE59504920D1/en not_active Expired - Fee Related
- 1995-07-15 SK SK62-97A patent/SK6297A3/en unknown
- 1995-07-15 CA CA002195558A patent/CA2195558A1/en not_active Abandoned
- 1995-07-15 JP JP8505420A patent/JPH10502932A/en active Pending
- 1995-07-15 EP EP95926901A patent/EP0772576B1/en not_active Expired - Lifetime
- 1995-07-15 KR KR1019970700384A patent/KR970704650A/en not_active Application Discontinuation
- 1995-07-15 PL PL95318316A patent/PL318316A1/en unknown
- 1995-07-15 BR BR9508311A patent/BR9508311A/en not_active Application Discontinuation
- 1995-07-15 CZ CZ97112A patent/CZ11297A3/en unknown
- 1995-07-15 MX MX9700531A patent/MX9700531A/en not_active Application Discontinuation
- 1995-07-15 WO PCT/EP1995/002787 patent/WO1996003361A1/en not_active Application Discontinuation
- 1995-07-15 AU AU31118/95A patent/AU693583B2/en not_active Expired - Fee Related
- 1995-07-15 HU HU9700155A patent/HUT77001A/en unknown
- 1995-07-20 ZA ZA956058A patent/ZA956058B/en unknown
- 1995-07-21 MY MYPI95002097A patent/MY131780A/en unknown
-
1997
- 1997-01-16 BG BG101140A patent/BG101140A/en unknown
- 1997-01-17 FI FI970216A patent/FI970216A/en not_active Application Discontinuation
- 1997-01-20 NO NO970237A patent/NO970237D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SK6297A3 (en) | 1997-06-04 |
| AU693583B2 (en) | 1998-07-02 |
| KR970704650A (en) | 1997-09-06 |
| CN1152903A (en) | 1997-06-25 |
| DE4425872A1 (en) | 1996-01-25 |
| BR9508311A (en) | 1997-12-23 |
| FI970216A0 (en) | 1997-01-17 |
| BG101140A (en) | 1997-08-29 |
| AU3111895A (en) | 1996-02-22 |
| PL318316A1 (en) | 1997-06-09 |
| MX9700531A (en) | 1997-04-30 |
| MY131780A (en) | 2007-08-30 |
| DE59504920D1 (en) | 1999-03-04 |
| ZA956058B (en) | 1996-02-27 |
| HUT77001A (en) | 1998-01-28 |
| NO970237L (en) | 1997-01-20 |
| CZ11297A3 (en) | 1997-05-14 |
| EP0772576A1 (en) | 1997-05-14 |
| JPH10502932A (en) | 1998-03-17 |
| WO1996003361A1 (en) | 1996-02-08 |
| FI970216A (en) | 1997-01-17 |
| NO970237D0 (en) | 1997-01-20 |
| EP0772576B1 (en) | 1999-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |