DE2608465B2 - Verfahren zur herstellung von brom - Google Patents
Verfahren zur herstellung von bromInfo
- Publication number
- DE2608465B2 DE2608465B2 DE19762608465 DE2608465A DE2608465B2 DE 2608465 B2 DE2608465 B2 DE 2608465B2 DE 19762608465 DE19762608465 DE 19762608465 DE 2608465 A DE2608465 A DE 2608465A DE 2608465 B2 DE2608465 B2 DE 2608465B2
- Authority
- DE
- Germany
- Prior art keywords
- bromine
- chlorine
- aluminum
- reaction
- weight
- 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.)
- Withdrawn
Links
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims description 58
- 229910052794 bromium Inorganic materials 0.000 title claims description 57
- 238000000034 method Methods 0.000 title claims description 27
- 239000000460 chlorine Substances 0.000 claims description 65
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 63
- 229910052801 chlorine Inorganic materials 0.000 claims description 63
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 57
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 34
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 34
- 229910052782 aluminium Inorganic materials 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 15
- -1 aluminum halide Chemical class 0.000 claims description 13
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000004821 distillation Methods 0.000 description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 238000003822 preparative gas chromatography Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- LYFQYPSHMWBHFG-UHFFFAOYSA-N 1-bromo-2-chloroethene Chemical group ClC=CBr LYFQYPSHMWBHFG-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- YHFHMOBBPOUKRV-UHFFFAOYSA-N O=ClOCCOCl=O Chemical compound O=ClOCCOCl=O YHFHMOBBPOUKRV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical class BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- HRLHOWWCFUKTIY-UHFFFAOYSA-L dichloroalumanylium Chemical compound Cl[Al+]Cl HRLHOWWCFUKTIY-UHFFFAOYSA-L 0.000 description 1
- QYQIKTBQNRWCEW-UHFFFAOYSA-K dichlorosyloxyalumanyl chlorite Chemical compound [Al+3].[O-]Cl=O.[O-]Cl=O.[O-]Cl=O QYQIKTBQNRWCEW-UHFFFAOYSA-K 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/09—Bromine; Hydrogen bromide
- C01B7/096—Bromine
-
- 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/204—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being a halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/555,801 US3961033A (en) | 1975-03-06 | 1975-03-06 | Preparation of bromine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2608465A1 DE2608465A1 (de) | 1976-09-16 |
| DE2608465B2 true DE2608465B2 (de) | 1978-01-19 |
Family
ID=24218674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762608465 Withdrawn DE2608465B2 (de) | 1975-03-06 | 1976-03-01 | Verfahren zur herstellung von brom |
Country Status (8)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4044113A (en) * | 1976-02-17 | 1977-08-23 | Ethyl Corporation | Preparation of bromine |
| US4197262A (en) * | 1978-11-03 | 1980-04-08 | The Dow Chemical Company | Preparation of organic halides |
| JPS6456637A (en) * | 1987-08-25 | 1989-03-03 | Toso Yuki Kagaku Kk | Production of 3-bromobenzaldehyde |
| IL89362A0 (en) * | 1989-02-21 | 1989-09-10 | Bromine Compounds Ltd | Preparation of tetrabromotetralin |
| CN101506092B (zh) * | 2006-08-25 | 2013-01-02 | 雅宝公司 | 氧化溴化物制备溴的方法及其中使用的催化剂 |
| CN103253635B (zh) * | 2013-05-23 | 2015-08-12 | 孟宪锋 | 一种从噻菌灵废水中提取溴素的工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3370096A (en) * | 1965-09-23 | 1968-02-20 | Universal Oil Prod Co | Halogen exchange process |
| GB1103725A (en) * | 1965-11-18 | 1968-02-21 | Ici Ltd | Bromination process |
| DE2045644C3 (de) * | 1970-09-16 | 1975-07-03 | Kali Und Salz Ag, 3500 Kassel | Verfahren zur Herstellung von praktisch wasser- und rückstandsfreiem elementarem Brom |
-
1975
- 1975-03-06 US US05/555,801 patent/US3961033A/en not_active Expired - Lifetime
-
1976
- 1976-02-11 GB GB5430/76A patent/GB1533771A/en not_active Expired
- 1976-02-23 CA CA246,344A patent/CA1070087A/en not_active Expired
- 1976-02-26 NL NL7602009A patent/NL7602009A/xx not_active Application Discontinuation
- 1976-03-01 DE DE19762608465 patent/DE2608465B2/de not_active Withdrawn
- 1976-03-01 BE BE164756A patent/BE839070A/xx unknown
- 1976-03-02 FR FR7605913A patent/FR2302963A1/fr active Granted
- 1976-03-05 JP JP51023375A patent/JPS51112791A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US3961033A (en) | 1976-06-01 |
| FR2302963A1 (fr) | 1976-10-01 |
| NL7602009A (nl) | 1976-09-08 |
| JPS5636121B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-08-21 |
| DE2608465A1 (de) | 1976-09-16 |
| GB1533771A (en) | 1978-11-29 |
| BE839070A (fr) | 1976-09-01 |
| CA1070087A (en) | 1980-01-22 |
| JPS51112791A (en) | 1976-10-05 |
| FR2302963B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHN | Withdrawal |