DE3447631A1 - Verfahren zur herstellung von hexabromcyclododecan - Google Patents
Verfahren zur herstellung von hexabromcyclododecanInfo
- Publication number
- DE3447631A1 DE3447631A1 DE19843447631 DE3447631A DE3447631A1 DE 3447631 A1 DE3447631 A1 DE 3447631A1 DE 19843447631 DE19843447631 DE 19843447631 DE 3447631 A DE3447631 A DE 3447631A DE 3447631 A1 DE3447631 A1 DE 3447631A1
- Authority
- DE
- Germany
- Prior art keywords
- hexabromocyclododecane
- cyclododecatriene
- chlorine
- hydrogen bromide
- reaction
- 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.)
- Granted
Links
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 19
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000002798 polar solvent Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- XRLIZCVYAYNXIF-UHFFFAOYSA-N cyclododeca-1,3,5-triene Chemical compound C1CCCC=CC=CC=CCC1 XRLIZCVYAYNXIF-UHFFFAOYSA-N 0.000 claims 1
- -1 Aliphatic alcohols Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000005893 bromination reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YWIBETYWGSNTAE-UHFFFAOYSA-N [Br].Br Chemical compound [Br].Br YWIBETYWGSNTAE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920006327 polystyrene foam Polymers 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843447631 DE3447631A1 (de) | 1984-12-28 | 1984-12-28 | Verfahren zur herstellung von hexabromcyclododecan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843447631 DE3447631A1 (de) | 1984-12-28 | 1984-12-28 | Verfahren zur herstellung von hexabromcyclododecan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3447631A1 true DE3447631A1 (de) | 1986-07-10 |
| DE3447631C2 DE3447631C2 (enrdf_load_stackoverflow) | 1989-07-20 |
Family
ID=6254023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843447631 Granted DE3447631A1 (de) | 1984-12-28 | 1984-12-28 | Verfahren zur herstellung von hexabromcyclododecan |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3447631A1 (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0276859A1 (en) * | 1987-01-29 | 1988-08-03 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Preparation of hexabromocyclododecane |
| FR2616429A1 (fr) * | 1987-06-11 | 1988-12-16 | Bromine Compounds Ltd | Procede de preparation du 1,2,5,6,9,10-hexabromocyclododecane |
| US5004847A (en) * | 1989-12-27 | 1991-04-02 | Ethyl Corporation | Recovery of hexabromocyclododecane particles |
| US5043492A (en) * | 1990-08-20 | 1991-08-27 | Ethyl Corporation | Method for producing hexabromocyclododecane |
| US5091057A (en) * | 1990-07-20 | 1992-02-25 | Ethyl Corporation | Stripping process for water removal from alcohol |
| US5593619A (en) * | 1992-10-22 | 1997-01-14 | Albemarle Corporation | Granulated flame retardant products |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290543B (de) * | 1967-05-12 | 1969-03-13 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Hexabromcyclododecan |
| DE2049055B2 (de) * | 1969-10-08 | 1978-10-05 | Nippon Chemical Ind | Verfahren zur Herstellung von 4-Brom-23-dichlorphenol |
| DE3013002C2 (de) * | 1980-04-03 | 1983-06-01 | Chemische Fabrik Kalk GmbH, 5000 Köln | Verfahren zur Herstellung von Hexabromcyclododecan gleichbleibender Qualität |
-
1984
- 1984-12-28 DE DE19843447631 patent/DE3447631A1/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290543B (de) * | 1967-05-12 | 1969-03-13 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Hexabromcyclododecan |
| DE2049055B2 (de) * | 1969-10-08 | 1978-10-05 | Nippon Chemical Ind | Verfahren zur Herstellung von 4-Brom-23-dichlorphenol |
| DE3013002C2 (de) * | 1980-04-03 | 1983-06-01 | Chemische Fabrik Kalk GmbH, 5000 Köln | Verfahren zur Herstellung von Hexabromcyclododecan gleichbleibender Qualität |
Non-Patent Citations (3)
| Title |
|---|
| HOUBEN-WEYL, Methoden der organischen Chemie, 4. Aufl., Bd. V/IV, 1960, S.15, 16 * |
| Organikum, 12.Aufl., Berlin 1974, S.187 * |
| RÖMPP: Chemie-Lexikon, 8.Aufl., S.521 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0276859A1 (en) * | 1987-01-29 | 1988-08-03 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Preparation of hexabromocyclododecane |
| FR2616429A1 (fr) * | 1987-06-11 | 1988-12-16 | Bromine Compounds Ltd | Procede de preparation du 1,2,5,6,9,10-hexabromocyclododecane |
| US4918253A (en) * | 1987-06-11 | 1990-04-17 | Bromine Compounds Limited | Process for the preparation of 1,2,5,6,9,10-hexabromocyclododecane |
| US5004847A (en) * | 1989-12-27 | 1991-04-02 | Ethyl Corporation | Recovery of hexabromocyclododecane particles |
| US5091057A (en) * | 1990-07-20 | 1992-02-25 | Ethyl Corporation | Stripping process for water removal from alcohol |
| US5043492A (en) * | 1990-08-20 | 1991-08-27 | Ethyl Corporation | Method for producing hexabromocyclododecane |
| US5593619A (en) * | 1992-10-22 | 1997-01-14 | Albemarle Corporation | Granulated flame retardant products |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3447631C2 (enrdf_load_stackoverflow) | 1989-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |