CA1087211A - Procede de polybromuration de bisphenoxyalcanes - Google Patents

Procede de polybromuration de bisphenoxyalcanes

Info

Publication number: CA1087211A
Authority: CA; Canada
Prior art keywords: bromine; lewis acid; acid catalyst; product; organic solvent
Prior art date: 1976-03-08
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

Application number

CA270,158A

Other languages

English (en)

Inventor

Henry J. Barda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Vibrantz Corp

Original Assignee

Ferro 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.)

1976-03-08

Filing date

1977-01-21

Publication date

1980-10-07

1977-01-21 Application filed by Ferro Corp filed Critical Ferro Corp

1980-10-07 Application granted granted Critical

1980-10-07 Publication of CA1087211A publication Critical patent/CA1087211A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
230000008569 process Effects 0.000 title claims abstract description 45
150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 6
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims abstract description 41
239000011968 lewis acid catalyst Substances 0.000 claims abstract description 27
239000003960 organic solvent Substances 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 27
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
229910052794 bromium Inorganic materials 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
239000002841 Lewis acid Substances 0.000 claims description 9
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 9
229910001507 metal halide Inorganic materials 0.000 claims description 8
-1 metal halide Lewis acid Chemical class 0.000 claims description 8
238000003776 cleavage reaction Methods 0.000 claims description 7
230000007017 scission Effects 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
150000005309 metal halides Chemical group 0.000 claims description 6
229910052742 iron Inorganic materials 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
229910052787 antimony Inorganic materials 0.000 claims description 4
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 3
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 3
150000001649 bromium compounds Chemical class 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 2
YHMOQCYOOUHZSF-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[1-(2,3,4,5,6-pentabromophenoxy)ethoxy]benzene Chemical group BrC=1C(Br)=C(Br)C(Br)=C(Br)C=1OC(C)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br YHMOQCYOOUHZSF-UHFFFAOYSA-N 0.000 claims description 2
229910015845 BBr3 Inorganic materials 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
229910005258 GaBr3 Inorganic materials 0.000 claims description 2
229910021623 Tin(IV) bromide Inorganic materials 0.000 claims description 2
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 2
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
SRVXDMYFQIODQI-UHFFFAOYSA-K gallium(iii) bromide Chemical compound Br[Ga](Br)Br SRVXDMYFQIODQI-UHFFFAOYSA-K 0.000 claims description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 claims description 2
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 claims description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims 2
229910015844 BCl3 Inorganic materials 0.000 claims 1
229910015900 BF3 Inorganic materials 0.000 claims 1
229910005267 GaCl3 Inorganic materials 0.000 claims 1
229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
229910003074 TiCl4 Inorganic materials 0.000 claims 1
229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
229910007932 ZrCl4 Inorganic materials 0.000 claims 1
229910001627 beryllium chloride Inorganic materials 0.000 claims 1
LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 claims 1
JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 claims 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 1
UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 claims 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
LNBXMNQCXXEHFT-UHFFFAOYSA-N selenium tetrachloride Chemical compound Cl[Se](Cl)(Cl)Cl LNBXMNQCXXEHFT-UHFFFAOYSA-N 0.000 claims 1
235000011150 stannous chloride Nutrition 0.000 claims 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims 1
HPICRATUQFHULE-UHFFFAOYSA-J uranium(4+);tetrachloride Chemical compound Cl[U](Cl)(Cl)Cl HPICRATUQFHULE-UHFFFAOYSA-J 0.000 claims 1
239000011592 zinc chloride Substances 0.000 claims 1
235000005074 zinc chloride Nutrition 0.000 claims 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
239000000047 product Substances 0.000 description 24
239000000243 solution Substances 0.000 description 16
238000005893 bromination reaction Methods 0.000 description 15
229940060038 chlorine Drugs 0.000 description 15
235000017168 chlorine Nutrition 0.000 description 15
230000031709 bromination Effects 0.000 description 14
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
150000007517 lewis acids Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 5
229910000042 hydrogen bromide Inorganic materials 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000004821 distillation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
JJEPQBZQAGCZTH-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenoxy)ethoxy]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OCCOC1=C(Br)C(Br)=C(Br)C(Br)=C1Br JJEPQBZQAGCZTH-UHFFFAOYSA-N 0.000 description 2
229910015400 FeC13 Inorganic materials 0.000 description 2
229910008046 SnC14 Inorganic materials 0.000 description 2
229910010066 TiC14 Inorganic materials 0.000 description 2
229940075103 antimony Drugs 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003063 flame retardant Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 1
NVRASYUHTRQZKB-UHFFFAOYSA-N 1,1,2,2,2-pentabromoethoxybenzene Chemical compound BrC(Br)(Br)C(Br)(Br)OC1=CC=CC=C1 NVRASYUHTRQZKB-UHFFFAOYSA-N 0.000 description 1
KTHDEQBOHFRRBF-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-ethoxybenzene Chemical compound CCOC1=C(Br)C(Br)=C(Br)C(Br)=C1Br KTHDEQBOHFRRBF-UHFFFAOYSA-N 0.000 description 1
YVVYMSXDQGDASK-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-(2,3,4-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=C(Br)C(Br)=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br YVVYMSXDQGDASK-UHFFFAOYSA-N 0.000 description 1
VWCPKTUHLKRBQP-UHFFFAOYSA-N 1-methyl-2-[2-(2-methylphenoxy)ethoxy]benzene Chemical compound CC1=CC=CC=C1OCCOC1=CC=CC=C1C VWCPKTUHLKRBQP-UHFFFAOYSA-N 0.000 description 1
FRRIJIONUFQFSM-UHFFFAOYSA-N 1-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OC(C)OC1=CC=CC=C1 FRRIJIONUFQFSM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
229910008066 SnC12 Inorganic materials 0.000 description 1
230000002411 adverse Effects 0.000 description 1
RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000007336 electrophilic substitution reaction Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
HDDSHPAODJUKPD-UHFFFAOYSA-N fenbendazole Chemical class C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 HDDSHPAODJUKPD-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
238000013022 venting Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA270,158A 1976-03-08 1977-01-21 Procede de polybromuration de bisphenoxyalcanes Expired CA1087211A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66462876A	1976-03-08	1976-03-08
US664,628		1976-03-08

Publications (1)

Publication Number	Publication Date
CA1087211A true CA1087211A (fr)	1980-10-07

Family

ID=24666767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA270,158A Expired CA1087211A (fr)	1976-03-08	1977-01-21	Procede de polybromuration de bisphenoxyalcanes

Country Status (13)

Country	Link
JP (1)	JPS6045168B2 (fr)
AT (1)	AT348506B (fr)
BE (1)	BE852043A (fr)
BR (1)	BR7701329A (fr)
CA (1)	CA1087211A (fr)
CH (1)	CH620665A5 (fr)
DE (1)	DE2710022C2 (fr)
FR (1)	FR2343711A1 (fr)
GB (1)	GB1519273A (fr)
IT (1)	IT1117280B (fr)
MX (1)	MX144927A (fr)
NL (1)	NL7700903A (fr)
SE (1)	SE441090B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2584395B1 (fr) *	1985-07-03	1987-09-25	Atochem	Procede de preparation de decabromodiphenylether
FR2584396B1 (fr) *	1985-07-03	1987-09-25	Atochem	Procede de preparation de derives bromes du diphenylether

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3449443A (en) *	1966-05-31	1969-06-10	Dow Chemical Co	Method for selectively brominating phenols
US3755444A (en) *	1969-04-24	1973-08-28	Dow Chemical Co	Bromination of organic compounds with a bromine chloride dioxane complex
US3845146A (en) *	1969-10-06	1974-10-29	Dow Chemical Co	Bromination with bromine chloride under pressure

1977
- 1977-01-21 CA CA270,158A patent/CA1087211A/fr not_active Expired
- 1977-01-27 GB GB3449/77A patent/GB1519273A/en not_active Expired
- 1977-01-28 NL NL7700903A patent/NL7700903A/xx not_active Application Discontinuation
- 1977-02-22 AT AT115777A patent/AT348506B/de not_active IP Right Cessation
- 1977-03-01 MX MX168203A patent/MX144927A/es unknown
- 1977-03-03 CH CH268077A patent/CH620665A5/fr not_active IP Right Cessation
- 1977-03-03 JP JP52022273A patent/JPS6045168B2/ja not_active Expired
- 1977-03-03 BE BE175437A patent/BE852043A/fr not_active IP Right Cessation
- 1977-03-04 BR BR7701329A patent/BR7701329A/pt unknown
- 1977-03-07 SE SE7702538A patent/SE441090B/xx not_active IP Right Cessation
- 1977-03-07 FR FR7706627A patent/FR2343711A1/fr active Granted
- 1977-03-08 IT IT46831/77A patent/IT1117280B/it active
- 1977-03-08 DE DE2710022A patent/DE2710022C2/de not_active Expired

Also Published As

Publication number	Publication date
FR2343711B1 (fr)	1983-10-28
DE2710022A1 (de)	1977-09-22
NL7700903A (nl)	1977-09-12
CH620665A5 (en)	1980-12-15
JPS6045168B2 (ja)	1985-10-08
DE2710022C2 (de)	1987-01-15
MX144927A (es)	1981-12-04
SE441090B (sv)	1985-09-09
AT348506B (de)	1979-02-26
GB1519273A (en)	1978-07-26
IT1117280B (it)	1986-02-17
BE852043A (fr)	1977-07-01
SE7702538L (sv)	1977-09-09
JPS52108937A (en)	1977-09-12
ATA115777A (de)	1978-07-15
BR7701329A (pt)	1977-11-08
FR2343711A1 (fr)	1977-10-07

Legal Events

Date	Code	Title	Description
1997-10-07	MKEX	Expiry

Publication	Publication Date	Title
EP0447152B1 (fr)	1994-08-03	Procédé pour la préparation de décabromodiphénylalcane
US4031142A (en)	1977-06-21	Process for the directed chlorination of alkylbenzenes
US4190609A (en)	1980-02-26	Process for the directed chlorination of xylenes
US4223169A (en)	1980-09-16	Process for polybrominating bisphenoxyalkanes
CA1087211A (fr)	1980-10-07	Procede de polybromuration de bisphenoxyalcanes
JP2593920B2 (ja)	1997-03-26	デカブロモジフエニルオキサイドの製造方法
US4600787A (en)	1986-07-15	Process for the preparation of aromatic compounds which contain perfluorinated side-chains bonded via a heteroatom
GB1576363A (en)	1980-10-08	Process for directed chlorination of alkylbenzenes
DE2800175C3 (de)	1981-12-17	Verfahren zur Herstellung von Mischungen aus p-Chlortoluol und o-Chlortoluol
JPH01268652A (ja)	1989-10-26	溶媒中で触媒を用いて４，４’―ジブロムビフェニルを製造する方法
US5041687A (en)	1991-08-20	Bromination process
CA1099286A (fr)	1981-04-14	Procede d'obtention d'halogenures d'acides organiques
CA1117139A (fr)	1982-01-26	Production de chlorure de monochloracetyle, et peut-etre d'acide monochloracetique, par hydratation du trichloroethylene
US4130594A (en)	1978-12-19	Liquid phase fluorination process
JPS6121204B2 (fr)	1986-05-26
US4098832A (en)	1978-07-04	Fluorination process catalysed by molybdenum pentachloride
KR900001285B1 (ko)	1990-03-05	브롬화 비페놀의 제조방법
KR100243453B1 (ko)	2000-02-01	메틸 방향족 화합물의 자유-라디칼 염소화 또는 브롬화 방법
JP3004113B2 (ja)	2000-01-31	デカブロモジフエニルアルカン方法
US4716251A (en)	1987-12-29	Diaryloxyalkane bromination process
US3914327A (en)	1975-10-21	Catalyzed halogen exchange process
CA1157884A (fr)	1983-11-29	Methode de preparation d'halogenures de trifluoromethylbenzoyle
US3405111A (en)	1968-10-08	Halogenation of organic compounds in halogenated acetonitrile solvents
JPS6147426A (ja)	1986-03-07	フツ素化環式炭化水素類の製法
US3372202A (en)	1968-03-05	Preparation of ar-halophenethyl alcohols