JP5058796B2 - 芳香族ポリハロゲン化ハロメチル化合物の合成 - Google Patents
芳香族ポリハロゲン化ハロメチル化合物の合成 Download PDFInfo
- Publication number
- JP5058796B2 JP5058796B2 JP2007522119A JP2007522119A JP5058796B2 JP 5058796 B2 JP5058796 B2 JP 5058796B2 JP 2007522119 A JP2007522119 A JP 2007522119A JP 2007522119 A JP2007522119 A JP 2007522119A JP 5058796 B2 JP5058796 B2 JP 5058796B2
- Authority
- JP
- Japan
- Prior art keywords
- pbb
- polystyrene
- bromine
- toluene
- flame retardant
- 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.)
- Expired - Fee Related
Links
- 125000003118 aryl group Chemical group 0.000 title description 9
- 125000004970 halomethyl group Polymers 0.000 title description 8
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- PYOIYKRKAHYOKO-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(bromomethyl)benzene Chemical compound BrCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br PYOIYKRKAHYOKO-UHFFFAOYSA-N 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 44
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- 238000004817 gas chromatography Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 230000031709 bromination Effects 0.000 claims description 12
- 238000005893 bromination reaction Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000005580 one pot reaction Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000013505 freshwater Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims 2
- 239000004793 Polystyrene Substances 0.000 description 49
- 239000003063 flame retardant Substances 0.000 description 38
- 229920002223 polystyrene Polymers 0.000 description 36
- 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 30
- 230000008569 process Effects 0.000 description 19
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 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 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- -1 flame retardant compound Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- ZHMURHNGRUXDMO-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-methylbenzene Chemical compound CC1=CC(Br)=C(Br)C(Br)=C1Br ZHMURHNGRUXDMO-UHFFFAOYSA-N 0.000 description 7
- HHPUADFPUXGYTC-UHFFFAOYSA-N 1,2,3-tribromo-5-methylbenzene;1,2,5-tribromo-3-methylbenzene;1,3,5-tribromo-2-methylbenzene Chemical compound CC1=CC(Br)=C(Br)C(Br)=C1.CC1=CC(Br)=CC(Br)=C1Br.CC1=C(Br)C=C(Br)C=C1Br HHPUADFPUXGYTC-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 5
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229940006460 bromide ion Drugs 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000004794 expanded polystyrene Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920005990 polystyrene resin Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000011968 lewis acid catalyst Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000002572 peristaltic effect Effects 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920006327 polystyrene foam Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 241000894007 species Species 0.000 description 3
- GRKDVZMVHOLESV-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl)methyl prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(COC(=O)C=C)C(Br)=C1Br GRKDVZMVHOLESV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WVFBDVFCOCLEFM-UHFFFAOYSA-N 1,1,2,4,4-pentachlorobuta-1,3-diene Chemical compound ClC(Cl)=CC(Cl)=C(Cl)Cl WVFBDVFCOCLEFM-UHFFFAOYSA-N 0.000 description 1
- UJJSQULCWJOFRO-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(chloromethyl)benzene Chemical compound ClCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br UJJSQULCWJOFRO-UHFFFAOYSA-N 0.000 description 1
- XDSDCTDECRVDTB-UHFFFAOYSA-N 2-bromo-2-methylpropanenitrile Chemical compound CC(C)(Br)C#N XDSDCTDECRVDTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 229920000426 Microplastic Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- PTMMCIFMVIXHBD-UHFFFAOYSA-N [4-(4-hydroxyphenyl)phenyl] phenyl hydrogen phosphate Chemical compound C1=CC(O)=CC=C1C(C=C1)=CC=C1OP(O)(=O)OC1=CC=CC=C1 PTMMCIFMVIXHBD-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000227 grinding Methods 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/02—Monocyclic halogenated hydrocarbons
- C07C23/10—Monocyclic halogenated hydrocarbons with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0019—Use of organic additives halogenated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
- C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
- C08J2325/06—Polystyrene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL163101 | 2004-07-19 | ||
| IL16310104 | 2004-07-19 | ||
| PCT/IL2005/000768 WO2006008738A1 (en) | 2004-07-19 | 2005-07-19 | Synthesis of aromatic polyhalogenated halomethyl compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008506769A JP2008506769A (ja) | 2008-03-06 |
| JP2008506769A5 JP2008506769A5 (enExample) | 2008-06-05 |
| JP5058796B2 true JP5058796B2 (ja) | 2012-10-24 |
Family
ID=35427728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522119A Expired - Fee Related JP5058796B2 (ja) | 2004-07-19 | 2005-07-19 | 芳香族ポリハロゲン化ハロメチル化合物の合成 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7601774B2 (enExample) |
| EP (1) | EP1773744B1 (enExample) |
| JP (1) | JP5058796B2 (enExample) |
| KR (1) | KR101197972B1 (enExample) |
| CN (1) | CN1989091A (enExample) |
| IL (1) | IL180424A (enExample) |
| WO (1) | WO2006008738A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006008738A1 (en) * | 2004-07-19 | 2006-01-26 | Bromine Compounds Ltd. | Synthesis of aromatic polyhalogenated halomethyl compounds |
| GB2435479A (en) * | 2006-02-23 | 2007-08-29 | Bromine Compounds Ltd | Formulations comprising pentabromobenzylbromide and their use as flame retardants |
| IL188983A (en) | 2008-01-23 | 2014-01-30 | Bromine Compounds Ltd | Delay in combustion in fabrics |
| US20080221239A1 (en) * | 2007-03-07 | 2008-09-11 | Falloon Stephen B | Flame retardant composition for use in styrenics |
| CN100545136C (zh) * | 2007-10-11 | 2009-09-30 | 同济大学 | 一种五溴苄基溴的制备方法 |
| US20120123007A1 (en) * | 2009-02-26 | 2012-05-17 | Smadar Hini | Styrenic polymer composition |
| EP2697272B1 (en) | 2011-04-14 | 2015-02-18 | Bromine Compounds Ltd. | Process for the preparation of the monomer pentabromobenzyl acrylate and polymerization thereof |
| CN102964210A (zh) * | 2012-12-22 | 2013-03-13 | 山东天一化学股份有限公司 | 一种白色五溴苄基溴的合成工艺 |
| WO2014106841A1 (en) | 2013-01-06 | 2014-07-10 | Bromine Compounds Ltd. | Preparation of bromine-containing aromatic compounds and their application as flame retardants |
| CN106715516B (zh) | 2014-07-08 | 2019-04-19 | 溴化合物有限公司 | 用作阻燃剂的含溴聚合物的制备 |
| JP6609614B2 (ja) | 2014-07-08 | 2019-11-20 | ブローミン コンパウンズ リミテッド | 臭素含有重合体の調製およびその難燃剤としての応用 |
| CN106083520A (zh) * | 2016-06-17 | 2016-11-09 | 潜江新亿宏有机化工有限公司 | 2（3）氯‑对甲基氯苄的生产方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2582452A (en) * | 1948-12-16 | 1952-01-15 | Diamond Alkali Co | Transparent, flame-resistant polystyrene |
| GB1107283A (en) | 1966-04-29 | 1968-03-27 | Berk Ltd | Expandable polystyrene compositions and expanded polystyrene formed therefrom |
| US3874155A (en) * | 1973-01-30 | 1975-04-01 | Fmc Corp | Flame-retardant fiber blend |
| DE2534210C3 (de) | 1975-07-31 | 1981-04-23 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Seitenkettenchlorierung von perhalogenierten Methylaromaten und einige 4,4'-Bis-(cholormethyl)-ar-octahalogendiphenyläther |
| DE3828059A1 (de) | 1988-08-18 | 1990-02-22 | Bayer Ag | Verfahren zur herstellung von seitenkettenhalogenierten alkylbenzolderivaten |
| DE19547249A1 (de) | 1995-12-18 | 1997-06-19 | Hoechst Ag | Verfahren zur Herstellung von aromatischen (Bromalkyl)-substituierten Kohlenwasserstoffverbindungen |
| US6028156A (en) * | 1996-01-16 | 2000-02-22 | Bromine Compounds, Ltd. | Process for the preparation of poly-(halobenzyl acrylate) |
| US5811470A (en) * | 1996-05-06 | 1998-09-22 | Albemarle Corporation | Flame retardant styrenic polymers |
| JPH11130708A (ja) * | 1997-10-30 | 1999-05-18 | Tosoh Corp | モノブロモメチル化芳香族化合物の製造方法 |
| JPH11279381A (ja) | 1998-03-31 | 1999-10-12 | Polyplastics Co | 難燃性ポリエステル樹脂組成物 |
| US6632870B2 (en) | 1998-06-11 | 2003-10-14 | Bromine Compounds Ltd. | Flame-retarted transparent plastics |
| EP1112308A1 (en) * | 1998-08-28 | 2001-07-04 | The Dow Chemical Company | Fire resistant styrene polymer foams with reduced brominated fire retardant |
| CN1135251C (zh) * | 1998-12-09 | 2004-01-21 | 巴斯福股份公司 | 发泡性聚苯乙烯粒子的制备工艺 |
| JP4266305B2 (ja) | 2000-12-22 | 2009-05-20 | 株式会社カネカ | スチレン系樹脂押出発泡体およびその製造方法 |
| US7091270B2 (en) * | 2002-01-31 | 2006-08-15 | Bromine Compounds Ltd. | Pentabromobenzyl alkyl ethers and their use as fire retardants |
| IL148326A (en) * | 2002-02-21 | 2008-04-13 | Bromine Compounds Ltd | Brominated esters, methods for their preparation and use thereof as flame retardants |
| US7585912B2 (en) * | 2004-07-19 | 2009-09-08 | Bromine Compounds Ltd. | Flame-retardant polystyrenes |
| WO2006008738A1 (en) * | 2004-07-19 | 2006-01-26 | Bromine Compounds Ltd. | Synthesis of aromatic polyhalogenated halomethyl compounds |
-
2005
- 2005-07-19 WO PCT/IL2005/000768 patent/WO2006008738A1/en not_active Ceased
- 2005-07-19 CN CNA2005800242550A patent/CN1989091A/zh active Pending
- 2005-07-19 JP JP2007522119A patent/JP5058796B2/ja not_active Expired - Fee Related
- 2005-07-19 US US11/632,788 patent/US7601774B2/en not_active Expired - Fee Related
- 2005-07-19 KR KR1020077003676A patent/KR101197972B1/ko not_active Expired - Fee Related
- 2005-07-19 EP EP05762121A patent/EP1773744B1/en not_active Expired - Lifetime
-
2006
- 2006-12-28 IL IL180424A patent/IL180424A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL180424A (en) | 2011-05-31 |
| EP1773744A1 (en) | 2007-04-18 |
| CN1989091A (zh) | 2007-06-27 |
| US20070205403A1 (en) | 2007-09-06 |
| WO2006008738A1 (en) | 2006-01-26 |
| US7601774B2 (en) | 2009-10-13 |
| IL180424A0 (en) | 2007-06-03 |
| JP2008506769A (ja) | 2008-03-06 |
| KR20070038551A (ko) | 2007-04-10 |
| EP1773744B1 (en) | 2013-01-16 |
| KR101197972B1 (ko) | 2012-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5058796B2 (ja) | 芳香族ポリハロゲン化ハロメチル化合物の合成 | |
| EP1032602B9 (en) | Process for the preparation of brominated polystyrene having improved color characteristics | |
| US4521633A (en) | Bromination process | |
| JPH04217931A (ja) | デカブロモジフエニルアルカンの製法 | |
| RU2442803C2 (ru) | Огнезащитные средства для применения в пеностиролах | |
| US20080200573A1 (en) | Flame Retarded Styrenic Foams and Foam Precursors | |
| RU2455324C2 (ru) | Антипиреновая композиция для применения в полистиролах | |
| JPS63188634A (ja) | ヘキサブロモシクロドデカンの製造法 | |
| KR101098281B1 (ko) | 브롬화 디페닐에탄 혼합물, 그 제조방법 및 이를 이용한 수지 조성물 | |
| US7605207B2 (en) | Flame retardant bromobenzyl systems | |
| CN101134711A (zh) | 一种五溴苄基溴的制备方法 | |
| JPH0499743A (ja) | 高品質テトラブロモビスフェノールａの製法 | |
| TWI422566B (zh) | 高含量十溴二苯基乙烷之製備與提供 | |
| JP4324984B2 (ja) | 臭素化ｐ−クミルフェノール誘導体、その製造法及びそれを配合してなる難燃性樹脂組成物 | |
| CN116004000B (zh) | 一种磷硅协效阻燃尼龙的制备方法 | |
| CN102639474B (zh) | 具有低封留游离溴含量的高指标成分的十溴二苯基烷烃产物的制备 | |
| JP2762718B2 (ja) | ブロモエチルポリブロモベンゼンの製造方法 | |
| JP2001523738A (ja) | 改善された色性を有する臭化ポリスチレンの製造方法 | |
| JP2005120207A (ja) | プラスチック用難燃剤組成物 | |
| JPS5913484B2 (ja) | 光に安定なブロム化ジフエニルエ−テルの製造方法 | |
| EP1119536A1 (en) | Novel bromine-containing 1,2-bis(phenyl) tetrafluoro ethanes and method of imparting flame retardancy to flammable materials | |
| JPH1180051A (ja) | １，３−ジメチル−３−フェニル−１−（２−メチル−２−フェニルプロピル）インダン臭素化物及びその製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080416 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080416 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110204 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110215 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110512 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110519 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110614 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110621 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110714 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111025 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120124 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120131 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120223 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120301 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120322 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120329 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120405 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120710 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120807 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120801 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120817 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: R3D02 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |