IL97658A - Process for the preparation of thin bromodiphenyl - alkane - Google Patents
Process for the preparation of thin bromodiphenyl - alkaneInfo
- Publication number
- IL97658A IL97658A IL9765891A IL9765891A IL97658A IL 97658 A IL97658 A IL 97658A IL 9765891 A IL9765891 A IL 9765891A IL 9765891 A IL9765891 A IL 9765891A IL 97658 A IL97658 A IL 97658A
- Authority
- IL
- Israel
- Prior art keywords
- diphenylalkane
- bromine
- liquid
- product
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- -1 decabromodiphenyl alkane Chemical class 0.000 title description 18
- 238000002360 preparation method Methods 0.000 title description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 87
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 229910052794 bromium Inorganic materials 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 14
- 238000005893 bromination reaction Methods 0.000 claims description 14
- 230000031709 bromination Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910001868 water Inorganic materials 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical group C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 19
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 14
- 239000012535 impurity Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Chemical group 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001246 bromo group Chemical class Br* 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- KHELGZNRENAISC-UHFFFAOYSA-N (3-benzyl-2-methylpentyl)benzene Chemical compound C=1C=CC=CC=1CC(C)C(CC)CC1=CC=CC=C1 KHELGZNRENAISC-UHFFFAOYSA-N 0.000 description 1
- SSSBYZTYRWXPNJ-UHFFFAOYSA-N 10-phenyldecylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCCCCC1=CC=CC=C1 SSSBYZTYRWXPNJ-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- LWPGUKRRKCHRLZ-UHFFFAOYSA-N 4-phenylbutylbenzene;2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1.C=1C=CC=CC=1CCCCC1=CC=CC=C1 LWPGUKRRKCHRLZ-UHFFFAOYSA-N 0.000 description 1
- DVGPMIRVCZNXMD-UHFFFAOYSA-N 6-phenylhexylbenzene Chemical compound C=1C=CC=CC=1CCCCCCC1=CC=CC=C1 DVGPMIRVCZNXMD-UHFFFAOYSA-N 0.000 description 1
- WXQQXUQJVUAIDQ-UHFFFAOYSA-N 9-phenylnonylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCCCC1=CC=CC=C1 WXQQXUQJVUAIDQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910021478 group 5 element Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006025 oxidative dimerization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/532,800 US5030778A (en) | 1990-06-04 | 1990-06-04 | Decabromodiphenyl alkane process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97658A0 IL97658A0 (en) | 1992-06-21 |
| IL97658A true IL97658A (en) | 1994-07-31 |
Family
ID=24123228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9765891A IL97658A (en) | 1990-06-04 | 1991-03-22 | Process for the preparation of thin bromodiphenyl - alkane |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5030778A (ko) |
| EP (1) | EP0460922B1 (ko) |
| JP (1) | JP2902158B2 (ko) |
| KR (1) | KR0175673B1 (ko) |
| DE (1) | DE69105046T2 (ko) |
| ES (1) | ES2064043T3 (ko) |
| IL (1) | IL97658A (ko) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2047256C (en) * | 1990-07-30 | 2002-03-05 | Saadat Hussain | Process for decabromodiphenylalkane predominant product |
| TW284788B (ko) * | 1991-05-28 | 1996-09-01 | L Air Liquide Soliete And Nyme Dour L Expl Des Proce | |
| JP3193494B2 (ja) * | 1992-01-03 | 2001-07-30 | レール・リキード・ソシエテ・アノニム・プール・レテュード・エ・レクスプロワタシオン・デ・プロセデ・ジョルジュ・クロード | 希ガスを使用し、グルコースから高フルクトースコーンシロップを製造する方法 |
| US6342261B1 (en) | 1992-04-03 | 2002-01-29 | American Air Liquide | Method of preserving foods using noble gases |
| US5364777A (en) * | 1992-04-03 | 1994-11-15 | American Air Liquide | Method of improving lipase activity using noble gases |
| DE69311656T2 (de) | 1992-04-03 | 1998-01-29 | Air Liquide | Methode zur kontrolle des bräunungsverfahrens mittels edelgasen |
| US5324874A (en) * | 1992-05-26 | 1994-06-28 | Ethyl Corporation | Process for a decarbromodiphenylethane predominate product having enhanced whiteness |
| EP0571859A3 (en) * | 1992-05-26 | 1994-11-02 | Ethyl Corp | Product with preponderance of decabromodiphenylethane of improved whiteness. |
| US5328823A (en) * | 1992-11-27 | 1994-07-12 | American Air Liquide | Enzyme-based biosensors for detecting noble gases |
| US5382525A (en) * | 1992-11-27 | 1995-01-17 | American Air Liquide | Method of effecting increased performance of diagnostic enzyme reaction systems using noble gases |
| CA2109458A1 (en) | 1992-11-27 | 1994-05-28 | Kevin C. Spencer | Method of improving processes using pectinase enzymes with noble gases |
| DE69413217T2 (de) * | 1993-04-07 | 1999-02-18 | Great Lakes Chemical Corp., West Lafayette, Ind. | Bromierte diphenylalkane und verfahren |
| JP2596889B2 (ja) * | 1993-08-18 | 1997-04-02 | チッソ株式会社 | 樹脂組成物 |
| US6518468B1 (en) | 1994-09-16 | 2003-02-11 | Albemarle Corporation | Bromination process |
| DE69521708T2 (de) * | 1994-09-16 | 2001-10-25 | Albemarle Corp., Baton Rouge | Bromierungsverfahren |
| EP0784648B2 (en) * | 1994-10-05 | 2010-10-27 | Great Lakes Chemical Corporation | Continuous bromination process and products thereof |
| US6117371A (en) * | 1994-10-05 | 2000-09-12 | Great Lakes Chemical Corporation | Continuous bromination process and products thereof |
| DE19512407A1 (de) * | 1995-04-03 | 1996-10-10 | Basf Ag | Flammgeschützte thermoplastische Formmassen |
| US6743825B1 (en) | 2001-08-03 | 2004-06-01 | Albemarle Corporation | Poly(bromoaryl)alkane additives and methods for their preparation and use |
| US7255927B2 (en) * | 2001-12-05 | 2007-08-14 | Isola Usa Corp. | Laminate composition |
| AU2002365609A1 (en) * | 2001-12-05 | 2003-06-17 | Isola Laminate Systems Corp. | Prepreg and composition of epoxy resin(s), sma copolymers(s) and bis-maleimide triazine resin(s) |
| EP1461383B2 (en) * | 2001-12-05 | 2012-06-06 | Isola Laminate Systems, Corp. | Thermosetting resin composition for high performance laminates |
| AU2002361780A1 (en) * | 2001-12-21 | 2003-07-15 | Pabu Services, Inc. | Method and apparatus for producing decabromodiphenyl alkanes |
| US20080058558A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of decabromodiphenyl oxide |
| EP2057110A1 (en) * | 2006-08-29 | 2009-05-13 | Albermarle Corporation | Preparation of decahalodiphenyl ethane |
| WO2008026215A2 (en) * | 2006-08-31 | 2008-03-06 | Bromine Compounds Ltd. | A process for preparing polybrominated compounds |
| WO2008057645A1 (en) * | 2006-11-08 | 2008-05-15 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane |
| JP5537945B2 (ja) * | 2006-11-09 | 2014-07-02 | アルベマール・コーポレーシヨン | 吸蔵臭素を含有する固体臭素化芳香族有機化合物の処理 |
| WO2008066980A1 (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 |
| EP2132158B1 (en) * | 2007-03-16 | 2014-08-13 | Albemarle Corporation | Preparation and provision of high assay 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 |
| CN101643388B (zh) * | 2009-06-22 | 2012-06-27 | 泰州百力化学股份有限公司 | 十溴二苯乙烷的制备方法 |
| EP2459506B1 (en) * | 2009-07-27 | 2014-04-09 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane product with low occluded free bromine content |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1229815A (fr) * | 1959-03-10 | 1960-09-09 | Electro Chimie Soc D | Procédé de préparation de diphényle chloré et produits ainsi obtenus |
| FR2031649A5 (ko) * | 1969-02-03 | 1970-11-20 | Ugine Kuhlmann | |
| 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 |
| FR2236818B1 (ko) * | 1973-07-13 | 1976-04-30 | Ugine Kuhlmann | |
| CA1321213C (en) * | 1988-06-13 | 1993-08-10 | Saadat Hussain | Bromination process |
-
1990
- 1990-06-04 US US07/532,800 patent/US5030778A/en not_active Expired - Lifetime
-
1991
- 1991-03-22 IL IL9765891A patent/IL97658A/en not_active IP Right Cessation
- 1991-04-03 KR KR1019910005394A patent/KR0175673B1/ko not_active Expired - Lifetime
- 1991-05-28 JP JP3150854A patent/JP2902158B2/ja not_active Expired - Lifetime
- 1991-06-04 EP EP91305055A patent/EP0460922B1/en not_active Expired - Lifetime
- 1991-06-04 DE DE69105046T patent/DE69105046T2/de not_active Expired - Lifetime
- 1991-06-04 ES ES91305055T patent/ES2064043T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2064043T3 (es) | 1995-01-16 |
| EP0460922B1 (en) | 1994-11-09 |
| KR920000681A (ko) | 1992-01-29 |
| IL97658A0 (en) | 1992-06-21 |
| KR0175673B1 (ko) | 1999-05-15 |
| JP2902158B2 (ja) | 1999-06-07 |
| JPH04261128A (ja) | 1992-09-17 |
| DE69105046D1 (de) | 1994-12-15 |
| EP0460922A1 (en) | 1991-12-11 |
| DE69105046T2 (de) | 1995-04-06 |
| US5030778A (en) | 1991-07-09 |
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| EXP | Patent expired |