IL97658A - Process for the preparation of thin bromodiphenyl - alkane - Google Patents

Process for the preparation of thin bromodiphenyl - alkane

Info

Publication number: IL97658A
Authority: IL; Israel
Prior art keywords: diphenylalkane; bromine; liquid; product; reaction
Prior art date: 1990-06-04

Application number

IL9765891A

Other languages

English (en)

Hebrew (he)

Other versions

IL97658A0 (en

Original Assignee

Ethyl Corp

Priority date (The priority date 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 date listed.)

1990-06-04

Filing date

1991-03-22

Publication date

1994-07-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24123228&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL97658(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-03-22 Application filed by Ethyl Corp filed Critical Ethyl Corp

1992-06-21 Publication of IL97658A0 publication Critical patent/IL97658A0/xx

1994-07-31 Publication of IL97658A publication Critical patent/IL97658A/en

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)

IL9765891A 1990-06-04 1991-03-22 Process for the preparation of thin bromodiphenyl - alkane IL97658A (en)

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)

* Cited by examiner, † Cited by third party
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
US5364777A (en) *	1992-04-03	1994-11-15	American Air Liquide	Method of improving lipase activity using noble gases
WO1993019628A1 (en)	1992-04-03	1993-10-14	L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude	A method of controlling browning reactions using noble gases
US6342261B1 (en)	1992-04-03	2002-01-29	American Air Liquide	Method of preserving foods using noble gases
EP0571859A3 (en) *	1992-05-26	1994-11-02	Ethyl Corp	Product with preponderance of decabromodiphenylethane of improved whiteness.
US5324874A (en) *	1992-05-26	1994-06-28	Ethyl Corporation	Process for a decarbromodiphenylethane predominate product having enhanced whiteness
US5382525A (en) *	1992-11-27	1995-01-17	American Air Liquide	Method of effecting increased performance of diagnostic enzyme reaction systems using noble gases
US5328823A (en) *	1992-11-27	1994-07-12	American Air Liquide	Enzyme-based biosensors for detecting noble gases
CA2109458A1 (en)	1992-11-27	1994-05-28	Kevin C. Spencer	Method of improving processes using pectinase enzymes with noble gases
JPH08510208A (ja) *	1993-04-07	1996-10-29	グレート・レークス・ケミカル・コーポレーション	臭素化ジフェニルアルカン生成物および製法
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
WO1996008457A1 (en) *	1994-09-16	1996-03-21	Albemarle Corporation	Improved bromination process
US6117371A (en) *	1994-10-05	2000-09-12	Great Lakes Chemical Corporation	Continuous bromination process and products thereof
WO1996011227A1 (en) *	1994-10-05	1996-04-18	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
WO2003048251A1 (en) *	2001-12-05	2003-06-12	Isola Laminate Systems Corp.	Prepreg and composition of epoxy resin(s), sma copolymers(s) and bis-maleimide triazine resin(s)
ATE425209T1 (de) *	2001-12-05	2009-03-15	Isola Laminate Systems Corp	Wärmehärtende harzzusammensetzung für hochleistungslaminate
US7255927B2 (en) *	2001-12-05	2007-08-14	Isola Usa Corp.	Laminate composition
CN100448821C (zh) *	2001-12-21	2009-01-07	帕布服务公司	生产十溴二苯基烷烃的方法与装置
CN101511758A (zh) *	2006-08-29	2009-08-19	雅宝公司	十卤代二苯乙烷的制备
US20080058558A1 (en) *	2006-08-29	2008-03-06	Albemarle Corporation	Preparation of 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
WO2008057645A1 (en) *	2006-11-08	2008-05-15	Albemarle Corporation	Preparation of high assay decabromodiphenylalkane
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- 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 DE DE69105046T patent/DE69105046T2/de not_active Expired - Lifetime
- 1991-06-04 EP EP91305055A patent/EP0460922B1/en not_active Expired - Lifetime
- 1991-06-04 ES ES91305055T patent/ES2064043T3/es not_active Expired - Lifetime

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Publication number	Publication date
JP2902158B2 (ja)	1999-06-07
US5030778A (en)	1991-07-09
ES2064043T3 (es)	1995-01-16
EP0460922A1 (en)	1991-12-11
EP0460922B1 (en)	1994-11-09
DE69105046D1 (de)	1994-12-15
KR0175673B1 (ko)	1999-05-15
KR920000681A (ko)	1992-01-29
IL97658A0 (en)	1992-06-21
JPH04261128A (ja)	1992-09-17
DE69105046T2 (de)	1995-04-06

Legal Events

Date	Code	Title
1997-07-13	KB	Patent renewed
2001-07-24	KB	Patent renewed
2005-05-17	KB	Patent renewed
2009-09-15	KB	Patent renewed
2011-12-29	EXP	Patent expired

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US5302768A (en)	1994-04-12	Process for decarbromodiphenylalkane predominant product
EP0447152B1 (en)	1994-08-03	Decabromodiphenyl alkane process
US5401890A (en)	1995-03-28	Process and apparatus for heat treating halogenated compounds
US5324874A (en)	1994-06-28	Process for a decarbromodiphenylethane predominate product having enhanced whiteness
CA1321213C (en)	1993-08-10	Bromination process
US3833674A (en)	1974-09-03	Recovery of brominated biphenyl
US5124496A (en)	1992-06-23	Process for decabromodiphenylalkane predominant product
US5077334A (en)	1991-12-31	Flame-retarded formulations of thermoplastics and decabromodiphenylethane
EP0299270A1 (en)	1989-01-18	Bromination process
EP0571859A2 (en)	1993-12-01	A decabromodiphenylethane predominated product having enhanced whiteness
EP0265150A1 (en)	1988-04-27	Process for the preparation of decabromodiphenyl ether with improved thermal stability
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CA2094469C (en)	2005-09-20	Process for a decabromodiphenylethane predominate product having enhanced whiteness
JP5307314B2 (ja)	2013-10-02	モノ−およびポリ−ベンジル−１，２，３，４−テトラヒドロナフタレン組成物と、この組成物またはモノベンジル−１，２，３，４−テトラヒドロナフタレン異性体混合物の熱伝導流体としての使用
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KR20120036344A (ko)	2012-04-17	폐색된 유리 브롬 함량이 낮은 고순도 데카브로모디페닐알칸 생성물의 제조 방법
WO2000020363A1 (en)	2000-04-13	Novel bromine-containing 1,2-bis(phenyl) tetrafluoro ethanes and method of imparting flame retardancy to flammable materials