NO133270B - - Google Patents
Download PDFInfo
- Publication number
- NO133270B NO133270B NO262/70A NO26270A NO133270B NO 133270 B NO133270 B NO 133270B NO 262/70 A NO262/70 A NO 262/70A NO 26270 A NO26270 A NO 26270A NO 133270 B NO133270 B NO 133270B
- Authority
- NO
- Norway
- Prior art keywords
- bromine
- hours
- added
- anhydrous
- reaction
- Prior art date
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 107
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 103
- 229910052794 bromium Inorganic materials 0.000 claims description 103
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 64
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 23
- 238000002844 melting Methods 0.000 claims description 16
- 230000008018 melting Effects 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 230000031709 bromination Effects 0.000 claims description 8
- 238000005893 bromination reaction Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 35
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 5
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 5
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 5
- IHTCQYOMBIVIBF-UHFFFAOYSA-N 1,2,3-tribromo-4,5,6-trichlorobenzene Chemical compound ClC1=C(Cl)C(Br)=C(Br)C(Br)=C1Cl IHTCQYOMBIVIBF-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- -1 alkyl terphenyls Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 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
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OZHJEQVYCBTHJT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-methylbenzene Chemical compound CC1=C(Br)C(Br)=C(Br)C(Br)=C1Br OZHJEQVYCBTHJT-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical class CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005944 trans-halogenation reaction Methods 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- BKIJOFDCKCFVQD-UHFFFAOYSA-N 1,2-dibromo-3,4,5-trichlorobenzene Chemical compound ClC1=CC(Br)=C(Br)C(Cl)=C1Cl BKIJOFDCKCFVQD-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 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 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000008423 fluorobenzenes Chemical class 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical class Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000004306 orthophenyl phenol Chemical class 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical class ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6902243A FR2031649A5 (hu) | 1969-02-03 | 1969-02-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133270B true NO133270B (hu) | 1975-12-29 |
| NO133270C NO133270C (hu) | 1976-04-07 |
Family
ID=9028508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO262/70A NO133270C (hu) | 1969-02-03 | 1970-01-23 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3752856A (hu) |
| BE (1) | BE739078A (hu) |
| BR (1) | BR6912782D0 (hu) |
| CA (1) | CA933948A (hu) |
| CH (1) | CH518887A (hu) |
| DE (1) | DE1950607A1 (hu) |
| FR (1) | FR2031649A5 (hu) |
| GB (1) | GB1278603A (hu) |
| IL (1) | IL33048A (hu) |
| LU (1) | LU59440A1 (hu) |
| NL (1) | NL6916819A (hu) |
| NO (1) | NO133270C (hu) |
| SE (1) | SE372513B (hu) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965197A (en) * | 1970-10-12 | 1976-06-22 | Michigan Chemical Corporation | Process for the complete bromination of non-fused ring aromatic compounds |
| USRE32606E (en) * | 1970-10-12 | 1988-02-16 | Great Lakes Chemical Corporation | Process for the complete bromination of non-fused ring aromatic compounds |
| FR2236818B1 (hu) * | 1973-07-13 | 1976-04-30 | Ugine Kuhlmann | |
| US4006195A (en) * | 1973-12-03 | 1977-02-01 | Hooker Chemicals & Plastics Corporation | Process for the catalytic production of dichlorotoluenes |
| US3970707A (en) * | 1974-04-11 | 1976-07-20 | Vasily Ivanovich Shvedov | Method for preparing 3,5,3',5'-tetrabromo-2,4,2',4'-tetraoxydiphenyl |
| US4327227A (en) * | 1980-02-20 | 1982-04-27 | Great Lakes Chemical Corporation | Process for producing purified brominated aromatic compounds |
| GB2081253B (en) * | 1980-07-23 | 1985-05-30 | Great Lakes Chemical Corp | Process for producing purified brominated aromatic compounds |
| EP0112722B1 (en) * | 1982-12-22 | 1987-05-13 | IHARA CHEMICAL INDUSTRY Co., Ltd. | Process for preparation of nuclear halides of monoalkylbenzenes |
| US4521633A (en) * | 1983-05-19 | 1985-06-04 | The Dow Chemical Company | Bromination process |
| US4716251A (en) * | 1986-02-07 | 1987-12-29 | Ethyl Corporation | Diaryloxyalkane bromination process |
| US4717776A (en) * | 1986-04-21 | 1988-01-05 | Ethyl Corporation | Bromination process |
| IL82503A0 (en) * | 1986-05-16 | 1987-11-30 | Dow Chemical Co | Process for the promination of biphenols |
| US4835322A (en) * | 1987-10-19 | 1989-05-30 | Great Lakes Chemical Corporation | Process for producing 4,4'-dibromodiphenyl ether |
| US5041687A (en) * | 1988-05-26 | 1991-08-20 | Ethyl Corporation | Bromination process |
| US5008477A (en) * | 1990-03-14 | 1991-04-16 | Ethyl Corporation | Decabromodiphenyl alkane process |
| US5030778A (en) * | 1990-06-04 | 1991-07-09 | Ethyl Corporation | Decabromodiphenyl alkane process |
| US5136107A (en) * | 1990-06-04 | 1992-08-04 | Ethyl Corporation | Process for halogenating aromatic compounds |
| US5055235A (en) * | 1990-12-12 | 1991-10-08 | Ethyl Corporation | Bromination process |
| US6518468B1 (en) | 1994-09-16 | 2003-02-11 | Albemarle Corporation | Bromination process |
| US6743825B1 (en) * | 2001-08-03 | 2004-06-01 | Albemarle Corporation | Poly(bromoaryl)alkane additives and methods for their preparation and use |
| US6841707B2 (en) | 2001-12-21 | 2005-01-11 | Pabu Services, Inc. | Method and apparatus for producing decabromodiphenyl alkanes |
| MX2008000281A (es) * | 2005-07-05 | 2008-04-04 | Albemarle Corp | Metodo para mejorar factores dielectricos y/o de disipacion de composiciones retardadoras de flama. |
| TW200813196A (en) * | 2006-07-11 | 2008-03-16 | Albemarle Corp | High assay decabromodiphenyl oxide |
| KR20090045304A (ko) * | 2006-08-29 | 2009-05-07 | 알베마를 코포레이션 | 데카할로디페닐 에탄의 제조방법 |
| US20080058555A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
| WO2008027776A2 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
| US20080058558A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of decabromodiphenyl oxide |
| US20080058557A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
| US20080058559A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
| CN101528654B (zh) * | 2006-08-31 | 2012-12-26 | 溴化合物有限公司 | 制备多溴化化合物的方法 |
| US20080108855A1 (en) * | 2006-11-08 | 2008-05-08 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane |
| EP2079673A1 (en) * | 2006-11-09 | 2009-07-22 | Albermarle Corporation | Processing of solid brominated aromatic organic compounds containing occluded bromine |
| US20080132743A1 (en) * | 2006-12-01 | 2008-06-05 | Albemarle Corporation | Production of high purity decabromodiphenylalkanes |
| US7408088B1 (en) | 2007-02-08 | 2008-08-05 | Albemarle Corporation | Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane |
| CN101636369B (zh) * | 2007-03-16 | 2014-07-30 | 雅宝公司 | 高测定含量十溴二苯基乙烷的制备和提供 |
| EP2132158B1 (en) * | 2007-03-16 | 2014-08-13 | Albemarle Corporation | Preparation and provision of high assay decabromodiphenylethane |
| US20100268003A1 (en) * | 2007-12-07 | 2010-10-21 | Albemarle Corporation | Process for increasing purity of solid brominated flame retardants during preparation |
| PL2459506T3 (pl) | 2009-07-27 | 2014-09-30 | Albemarle Corp | Wytwarzanie wysokiej próby produktu dekabromodifenyloalkanowego o niskiej zawartości zokludowanego wolnego bromu |
| CN109593027A (zh) * | 2018-12-11 | 2019-04-09 | 杭州纳尔森精细化工有限公司 | 一种有机阻燃剂十溴二苯醚的制备方法 |
| CN109369351A (zh) * | 2018-12-11 | 2019-02-22 | 杭州纳尔森精细化工有限公司 | 一种制备有机阻燃剂十溴二苯醚的溴化工艺 |
-
1969
- 1969-02-03 FR FR6902243A patent/FR2031649A5/fr not_active Expired
- 1969-08-20 GB GB41605/69A patent/GB1278603A/en not_active Expired
- 1969-09-12 LU LU59440D patent/LU59440A1/xx unknown
- 1969-09-19 BE BE739078D patent/BE739078A/xx unknown
- 1969-09-24 IL IL33048A patent/IL33048A/en unknown
- 1969-09-25 CH CH1446969A patent/CH518887A/fr not_active IP Right Cessation
- 1969-09-26 CA CA063310A patent/CA933948A/en not_active Expired
- 1969-09-26 BR BR212782/69A patent/BR6912782D0/pt unknown
- 1969-10-08 DE DE19691950607 patent/DE1950607A1/de active Pending
- 1969-11-07 NL NL6916819A patent/NL6916819A/xx unknown
- 1969-12-11 SE SE6917152A patent/SE372513B/xx unknown
-
1970
- 1970-01-23 NO NO262/70A patent/NO133270C/no unknown
- 1970-02-02 US US00007662A patent/US3752856A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL33048A0 (en) | 1969-11-30 |
| CA933948A (en) | 1973-09-18 |
| GB1278603A (en) | 1972-06-21 |
| BE739078A (hu) | 1970-03-02 |
| NL6916819A (hu) | 1970-08-05 |
| CH518887A (fr) | 1972-02-15 |
| BR6912782D0 (pt) | 1973-05-31 |
| DE1950607A1 (de) | 1970-08-06 |
| NO133270C (hu) | 1976-04-07 |
| IL33048A (en) | 1973-01-30 |
| LU59440A1 (hu) | 1970-01-08 |
| US3752856A (en) | 1973-08-14 |
| SE372513B (hu) | 1974-12-23 |
| FR2031649A5 (hu) | 1970-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO133270B (hu) | ||
| US3965197A (en) | Process for the complete bromination of non-fused ring aromatic compounds | |
| US3845146A (en) | Bromination with bromine chloride under pressure | |
| Cremlyn | Chlorosulfonic acid | |
| US3833674A (en) | Recovery of brominated biphenyl | |
| US3285965A (en) | Process for the production of bromine derivatives of aromatic compounds | |
| US3763248A (en) | Process for production of poly brominated aromatics | |
| JPS59216843A (ja) | 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 | |
| IL44080A (en) | Preparation of brominated aromatic compounds | |
| US3959387A (en) | Recovery of brominated biphenyl oxide | |
| BRPI0316844B1 (pt) | processo para preparar benzofenonas | |
| USRE32606E (en) | Process for the complete bromination of non-fused ring aromatic compounds | |
| US2948759A (en) | Process of nitrating aromatic hydrocarbons aided by an aromatic ion exchange resin | |
| US2471575A (en) | Process of preparing 2, 4-dichlorophenoxyacetic acid | |
| US4331613A (en) | Process for the preparation of trifluoromethylnaphthalenes | |
| US2902517A (en) | Preparation of mono- and diarylphosphines | |
| US2790786A (en) | Trichloromethyl halogen benzenes and process of making same | |
| BRPI0404626B1 (pt) | processo para a produção de 4-amino-3,5-diclorobenzotrifluoreto com obtenção de produtos em paralelo com alta pureza comercial | |
| US2308419A (en) | Method of making aralkyl iodides and corresponding alcohols | |
| US4482742A (en) | Process for preparing of 3,3'-diamino diphenylsulfones | |
| EP0009267B1 (en) | Process for the preparation of p-nitroso-diphenylhydroxylamines | |
| JPS6270326A (ja) | ジアリ−ルブタンの製造方法 | |
| Kodomari et al. | Direct Iodination of Aromatic Compounds with Iodine and Alumina-Supported Copper (II) Chloride or Sulfate. | |
| JP2549379B2 (ja) | ４−（ブロモまたはクロロ）メチル−３，５−ジハロ−２，６−ジ置換フエノ−ルの製造方法 | |
| US3952065A (en) | Method of producing chlorobenzenes from benzene sulphonyl chlorides |