JPS6045168B2 - ビスフエノキシアルカンの多臭素化法 - Google Patents

ビスフエノキシアルカンの多臭素化法

Info

Publication number: JPS6045168B2
Authority: JP; Japan
Prior art keywords: lewis acid; bromine; acid catalyst; carbon; reaction
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

JP52022273A

Other languages

English (en)

Japanese (ja)

Other versions

JPS52108937A (en

Inventor

ヘンリ−・ジエイ・バ−ダ

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

1977-03-03

Publication date

1985-10-08

1977-03-03 Application filed by Ferro Corp filed Critical Ferro Corp

1977-09-12 Publication of JPS52108937A publication Critical patent/JPS52108937A/ja

1985-10-08 Publication of JPS6045168B2 publication Critical patent/JPS6045168B2/ja

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 45
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 39
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 25
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
239000011968 lewis acid catalyst Substances 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
239000003054 catalyst Substances 0.000 claims description 21
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 20
239000000460 chlorine 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
239000003960 organic solvent Substances 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
239000002841 Lewis acid Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910001507 metal halide Inorganic materials 0.000 claims description 8
150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
150000001875 compounds Chemical class 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
-1 pentabromophenoxy Chemical group 0.000 claims description 6
239000000126 substance Substances 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
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
230000015572 biosynthetic process Effects 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl 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
230000003197 catalytic effect Effects 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
125000002947 alkylene group Chemical group 0.000 claims description 2
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 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
229910052787 antimony Inorganic materials 0.000 claims 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 2
150000001649 bromium compounds Chemical group 0.000 claims 2
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 21
238000005893 bromination reaction Methods 0.000 description 19
230000031709 bromination Effects 0.000 description 18
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 11
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
150000007517 lewis acids Chemical class 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 4
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 4
238000003776 cleavage reaction Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229910000042 hydrogen bromide Inorganic materials 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
230000007017 scission Effects 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
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000376 reactant Substances 0.000 description 3
YHMOQCYOOUHZSF-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[1-(2,3,4,5,6-pentabromophenoxy)ethoxy]benzene Chemical compound 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 description 2
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
229910015844 BCl3 Inorganic materials 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
230000002411 adverse Effects 0.000 description 2
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical class Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 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
238000000354 decomposition reaction Methods 0.000 description 2
230000007423 decrease Effects 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
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
239000007791 liquid phase Substances 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
239000000843 powder Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
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
MBAGZNQGOWWINU-UHFFFAOYSA-N 1,2-dibromo-3-[2-(2,3-dibromophenoxy)ethoxy]benzene Chemical compound BrC1=CC=CC(OCCOC=2C(=C(Br)C=CC=2)Br)=C1Br MBAGZNQGOWWINU-UHFFFAOYSA-N 0.000 description 1
YATIGPZCMOYEGE-UHFFFAOYSA-N 1,3,5-tribromo-2-[2-(2,4,6-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=CC(Br)=CC(Br)=C1OCCOC1=C(Br)C=C(Br)C=C1Br YATIGPZCMOYEGE-UHFFFAOYSA-N 0.000 description 1
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 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910005258 GaBr3 Inorganic materials 0.000 description 1
229910005267 GaCl3 Inorganic materials 0.000 description 1
229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910001627 beryllium chloride Inorganic materials 0.000 description 1
LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000007336 electrophilic substitution reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
SRVXDMYFQIODQI-UHFFFAOYSA-K gallium(iii) bromide Chemical compound Br[Ga](Br)Br SRVXDMYFQIODQI-UHFFFAOYSA-K 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
150000002739 metals Chemical class 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
HPICRATUQFHULE-UHFFFAOYSA-J uranium(4+);tetrachloride Chemical compound Cl[U](Cl)(Cl)Cl HPICRATUQFHULE-UHFFFAOYSA-J 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)

JP52022273A 1976-03-08 1977-03-03 ビスフエノキシアルカンの多臭素化法 Expired JPS6045168B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66462876A	1976-03-08	1976-03-08
US664628		1976-03-08

Publications (2)

Publication Number	Publication Date
JPS52108937A JPS52108937A (en)	1977-09-12
JPS6045168B2 true JPS6045168B2 (ja)	1985-10-08

Family

ID=24666767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52022273A Expired JPS6045168B2 (ja)	1976-03-08	1977-03-03	ビスフエノキシアルカンの多臭素化法

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
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
CA1087211A (fr)	1980-10-07
ATA115777A (de)	1978-07-15
BR7701329A (pt)	1977-11-08
FR2343711A1 (fr)	1977-10-07

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JP4314321B2 (ja)	2009-08-12	Ｔｆｐｘジクロライドの製造方法
US4223169A (en)	1980-09-16	Process for polybrominating bisphenoxyalkanes
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
JPS6045168B2 (ja)	1985-10-08	ビスフエノキシアルカンの多臭素化法
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
US6087537A (en)	2000-07-11	Method of producing dialkyl- and trialkyl-substituted benzaldehydes
US6080892A (en)	2000-06-27	Method of producing substituted benzaldehydes with catalytic amounts of acid
US5041687A (en)	1991-08-20	Bromination process
JPS6121204B2 (fr)	1986-05-26
JPH0285275A (ja)	1990-03-26	クロメンの製造法および重合法並びにその生成物
US4183873A (en)	1980-01-15	Liquid phase fluorination process
US4098832A (en)	1978-07-04	Fluorination process catalysed by molybdenum pentachloride
US4130594A (en)	1978-12-19	Liquid phase fluorination process
KR100243453B1 (ko)	2000-02-01	메틸 방향족 화합물의 자유-라디칼 염소화 또는 브롬화 방법
KR100220259B1 (ko)	1999-09-15	히드로플루오로카본의 제조방법
JP3004113B2 (ja)	2000-01-31	デカブロモジフエニルアルカン方法
US4967026A (en)	1990-10-30	Process for the production of chloromethyl phenethyl bromide
US3914327A (en)	1975-10-21	Catalyzed halogen exchange process
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