CA1189057A - Catalyst mixture and process for making 1,2- dichloroethane - Google Patents
Catalyst mixture and process for making 1,2- dichloroethaneInfo
- Publication number
- CA1189057A CA1189057A CA000415709A CA415709A CA1189057A CA 1189057 A CA1189057 A CA 1189057A CA 000415709 A CA000415709 A CA 000415709A CA 415709 A CA415709 A CA 415709A CA 1189057 A CA1189057 A CA 1189057A
- Authority
- CA
- Canada
- Prior art keywords
- dichloroethane
- chloride
- iii
- reaction
- salt
- 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000003054 catalyst Substances 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 19
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005977 Ethylene Substances 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- -1 alicyclic amine Chemical group 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229920000768 polyamine Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 230000036647 reaction Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910015400 FeC13 Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813148450 DE3148450A1 (de) | 1981-12-08 | 1981-12-08 | Katalysatorgemisch und verfahren zur herstellung von 1,2-dichlorethan |
| DEP3148450.6 | 1981-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1189057A true CA1189057A (en) | 1985-06-18 |
Family
ID=6148127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000415709A Expired CA1189057A (en) | 1981-12-08 | 1982-11-17 | Catalyst mixture and process for making 1,2- dichloroethane |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4747914A (en) * | 1985-05-29 | 1988-05-31 | Hoechst Aktiengesellschaft | Process for the purification of 1,2-dichloroethane |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247988A1 (de) * | 1982-12-24 | 1984-06-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 1,2-dichlorethan |
| DE3347153A1 (de) * | 1983-12-27 | 1985-07-04 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 1,2-dichlorethan |
| EP0835857A1 (en) * | 1996-03-13 | 1998-04-15 | Caprolactam Joint-Stock Company | Method of obtaining 1,2-dichloroethane |
| DE10050315C2 (de) | 2000-10-10 | 2003-08-21 | Uhde Gmbh | Verfahren zur Auflösung von Salzen in 1,2-Dichlorethan mittels Ultraschall und Vorrichtung zur Durchführung des Verfahrens |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486379A (en) * | 1946-07-22 | 1949-11-01 | Dow Chemical Co | Manufacture of nuclear halogenated alkenyl-benzene compounds |
| US3723543A (en) * | 1970-12-21 | 1973-03-27 | Olin Corp | Process for preparing 2,4,4,4-tetrachlorobutanol |
| US4058574A (en) * | 1972-07-11 | 1977-11-15 | Rhone-Progil | Process for the oxychlorination of hydrocarbons with ammonium chloride |
| GB1422303A (en) * | 1973-06-11 | 1976-01-28 | Stauffer Chemical Co | Production of ethylene dichloride |
| DE2540291C3 (de) * | 1975-09-10 | 1984-02-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung von 1,2-Dichloräthan und Katalysatorbehälter als Bestandteil einer Vorrichtung zur Durchführung des genannten Verfahrens |
| AU529847B2 (en) * | 1979-01-10 | 1983-06-23 | Akzo N.V. | Combined chlorinated hydrocarbon-sodium bicarbonate productio |
| US4282165A (en) * | 1980-03-24 | 1981-08-04 | Argus Chemical Corporation | Preparation of trimethyltin chloride from dimethyltin dichloride |
-
1981
- 1981-12-08 DE DE19813148450 patent/DE3148450A1/de not_active Withdrawn
-
1982
- 1982-11-16 ES ES517410A patent/ES8307529A1/es not_active Expired
- 1982-11-17 CA CA000415709A patent/CA1189057A/en not_active Expired
- 1982-11-25 EP EP82110897A patent/EP0082342B1/de not_active Expired
- 1982-11-25 DE DE8282110897T patent/DE3276154D1/de not_active Expired
- 1982-12-06 SU SU823520355A patent/SU1250165A3/ru active
- 1982-12-06 DD DD82245614A patent/DD208604A5/de not_active IP Right Cessation
- 1982-12-06 JP JP57212830A patent/JPS58104636A/ja active Granted
- 1982-12-07 NO NO824108A patent/NO158621C/no unknown
- 1982-12-07 AU AU91615/82A patent/AU553255B2/en not_active Ceased
- 1982-12-07 HU HU823918A patent/HU193155B/hu not_active IP Right Cessation
- 1982-12-07 BR BR8207099A patent/BR8207099A/pt not_active IP Right Cessation
- 1982-12-07 ZA ZA828976A patent/ZA828976B/xx unknown
- 1982-12-08 CS CS828902A patent/CS235975B2/cs unknown
- 1982-12-08 IN IN1426/CAL/82A patent/IN156063B/en unknown
- 1982-12-08 MX MX195509A patent/MX162900B/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4747914A (en) * | 1985-05-29 | 1988-05-31 | Hoechst Aktiengesellschaft | Process for the purification of 1,2-dichloroethane |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3148450A1 (de) | 1983-06-16 |
| NO824108L (no) | 1983-06-09 |
| DE3276154D1 (en) | 1987-06-04 |
| BR8207099A (pt) | 1983-10-11 |
| NO158621C (no) | 1988-10-12 |
| AU9161582A (en) | 1983-06-16 |
| ES517410A0 (es) | 1983-08-16 |
| SU1250165A3 (ru) | 1986-08-07 |
| EP0082342A2 (de) | 1983-06-29 |
| MX162900B (es) | 1991-07-08 |
| AU553255B2 (en) | 1986-07-10 |
| CS235975B2 (en) | 1985-05-15 |
| EP0082342A3 (en) | 1985-09-18 |
| IN156063B (enrdf_load_stackoverflow) | 1985-05-04 |
| JPH0230298B2 (enrdf_load_stackoverflow) | 1990-07-05 |
| EP0082342B1 (de) | 1987-04-29 |
| JPS58104636A (ja) | 1983-06-22 |
| ZA828976B (en) | 1983-10-26 |
| ES8307529A1 (es) | 1983-08-16 |
| NO158621B (no) | 1988-07-04 |
| DD208604A5 (de) | 1984-04-04 |
| HU193155B (en) | 1987-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |