JPS6210035A - 溶液として得られた不完全臭素化生成物を過臭素化生成物の形で維持する方法 - Google Patents
溶液として得られた不完全臭素化生成物を過臭素化生成物の形で維持する方法Info
- Publication number
- JPS6210035A JPS6210035A JP61157144A JP15714486A JPS6210035A JP S6210035 A JPS6210035 A JP S6210035A JP 61157144 A JP61157144 A JP 61157144A JP 15714486 A JP15714486 A JP 15714486A JP S6210035 A JPS6210035 A JP S6210035A
- Authority
- JP
- Japan
- Prior art keywords
- product
- perbrominated
- incompletely
- brominated
- treated
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 239000000047 product Substances 0.000 claims description 33
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000005893 bromination reaction Methods 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 230000031709 bromination Effects 0.000 claims description 6
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical group BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 238000011403 purification operation Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000006228 supernatant Substances 0.000 claims description 3
- 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 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- -1 aluminum halide Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ORYGKUIDIMIRNN-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenoxy)benzene Chemical compound BrC1=C(Br)C(Br)=CC(OC=2C(=C(Br)C(Br)=C(Br)C=2)Br)=C1Br ORYGKUIDIMIRNN-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8510162 | 1985-07-03 | ||
| FR8510162A FR2584394B1 (fr) | 1985-07-03 | 1985-07-03 | Procede de valorisation sous-forme de produits perbromes de produits sous-bromes obtenus en solutions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6210035A true JPS6210035A (ja) | 1987-01-19 |
Family
ID=9320928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61157144A Pending JPS6210035A (ja) | 1985-07-03 | 1986-07-03 | 溶液として得られた不完全臭素化生成物を過臭素化生成物の形で維持する方法 |
Country Status (10)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL80391A (en) * | 1986-10-22 | 1992-03-29 | Bromine Compounds Ltd | Process for the preparation of decabromodiphenyl ether with improved thermal stability |
| IL80390A (en) * | 1986-10-22 | 1992-06-21 | Bromine Compounds Ltd | Process for the preparation of decabromodiphenyl ether |
| WO2008027779A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of decabromodiphenyl oxide |
| WO2008027778A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5239638A (en) * | 1975-08-25 | 1977-03-28 | Toyo Soda Mfg Co Ltd | Process for preparation of decabromobiphenylether |
| JPS59216843A (ja) * | 1983-05-19 | 1984-12-06 | エチル コ−ポレイシヨン | ジフエニルエ−テルからデカブロモジフエニルエ−テルを製造するブロム化方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3763248A (en) * | 1971-03-02 | 1973-10-02 | Ethyl Corp | Process for production of poly brominated aromatics |
| US3833674A (en) * | 1972-08-24 | 1974-09-03 | Ethyl Corp | Recovery of brominated biphenyl |
| GB1472383A (en) * | 1976-01-23 | 1977-05-04 | Isc Chem Ltd | Bromination of diphenyl oxide |
| DD137803A3 (de) * | 1976-12-13 | 1979-09-26 | Hans Baltz | Verfahren zur herstellung von hexabrombenzol |
| DD128749A1 (de) * | 1976-12-13 | 1977-12-07 | Wolfgang Baumann | Verfahren zur herstellung von hexabrombenzol |
-
1985
- 1985-07-03 FR FR8510162A patent/FR2584394B1/fr not_active Expired
-
1986
- 1986-06-24 NL NL8601648A patent/NL8601648A/nl not_active Application Discontinuation
- 1986-06-27 IT IT20961/86A patent/IT1190141B/it active
- 1986-06-30 IL IL79285A patent/IL79285A0/xx unknown
- 1986-07-02 BE BE0/216867A patent/BE905039A/fr not_active IP Right Cessation
- 1986-07-02 DE DE19863622235 patent/DE3622235A1/de active Granted
- 1986-07-02 GB GB8616122A patent/GB2177399B/en not_active Expired
- 1986-07-03 ES ES8600100A patent/ES2000304A6/es not_active Expired
- 1986-07-03 JP JP61157144A patent/JPS6210035A/ja active Pending
- 1986-07-03 CH CH2694/86A patent/CH666677A5/fr not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5239638A (en) * | 1975-08-25 | 1977-03-28 | Toyo Soda Mfg Co Ltd | Process for preparation of decabromobiphenylether |
| JPS59216843A (ja) * | 1983-05-19 | 1984-12-06 | エチル コ−ポレイシヨン | ジフエニルエ−テルからデカブロモジフエニルエ−テルを製造するブロム化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL79285A0 (en) | 1986-09-30 |
| GB2177399B (en) | 1989-07-19 |
| GB8616122D0 (en) | 1986-08-06 |
| CH666677A5 (fr) | 1988-08-15 |
| FR2584394B1 (fr) | 1987-09-25 |
| DE3622235A1 (de) | 1987-01-15 |
| FR2584394A1 (fr) | 1987-01-09 |
| IT1190141B (it) | 1988-02-10 |
| BE905039A (fr) | 1987-01-02 |
| ES2000304A6 (es) | 1988-02-16 |
| IT8620961A0 (it) | 1986-06-27 |
| GB2177399A (en) | 1987-01-21 |
| NL8601648A (nl) | 1987-02-02 |
| IT8620961A1 (it) | 1987-12-27 |
| DE3622235C2 (enrdf_load_stackoverflow) | 1989-10-19 |
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