FR2486068A1 - Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes - Google Patents
Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes Download PDFInfo
- Publication number
- FR2486068A1 FR2486068A1 FR8014607A FR8014607A FR2486068A1 FR 2486068 A1 FR2486068 A1 FR 2486068A1 FR 8014607 A FR8014607 A FR 8014607A FR 8014607 A FR8014607 A FR 8014607A FR 2486068 A1 FR2486068 A1 FR 2486068A1
- Authority
- FR
- France
- Prior art keywords
- benzene
- formula
- alkali metal
- tetrachlorobenzene
- process according
- 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.)
- Granted
Links
- 229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 title claims description 19
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 title claims description 18
- 150000001340 alkali metals Chemical class 0.000 title claims description 4
- 239000002585 base Substances 0.000 title 1
- 239000008139 complexing agent Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 39
- -1 alkali metal amide Chemical class 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 28
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 claims abstract description 21
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical class ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 9
- 230000008707 rearrangement Effects 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 75
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 claims description 14
- 239000003352 sequestering agent Substances 0.000 claims description 14
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- XZGIHWAIIZHXKX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-n,n-bis[2-(2-ethoxyethoxy)ethyl]ethanamine Chemical compound CCOCCOCCN(CCOCCOCC)CCOCCOCC XZGIHWAIIZHXKX-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical group [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 1
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 abstract description 18
- 150000004816 dichlorobenzenes Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000000536 complexating effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 150000005671 trienes Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000007983 Tris buffer Substances 0.000 description 13
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QZYNWJQFTJXIRN-UHFFFAOYSA-N 1,2,3,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1 QZYNWJQFTJXIRN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 3
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FIIZQHKGJMRJIL-UHFFFAOYSA-N n,3-diphenylprop-2-enamide Chemical compound C=1C=CC=CC=1C=CC(=O)NC1=CC=CC=C1 FIIZQHKGJMRJIL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PZGBZOMSKOTXQX-UHFFFAOYSA-N 1,2,3,5-tetrachlorobenzene;1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1.ClC1=CC(Cl)=C(Cl)C=C1Cl PZGBZOMSKOTXQX-UHFFFAOYSA-N 0.000 description 1
- FWAJPSIPOULHHH-UHFFFAOYSA-N 1,2,4-tribromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1 FWAJPSIPOULHHH-UHFFFAOYSA-N 0.000 description 1
- FYQDQKAKGXUKOR-UHFFFAOYSA-N 1,2,4-trichlorobenzene;1,3,5-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1.ClC1=CC(Cl)=CC(Cl)=C1 FYQDQKAKGXUKOR-UHFFFAOYSA-N 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- ROJJKFAXAOCLKK-UHFFFAOYSA-N 1-bromo-4-chloro-2-iodobenzene Chemical compound ClC1=CC=C(Br)C(I)=C1 ROJJKFAXAOCLKK-UHFFFAOYSA-N 0.000 description 1
- RULYNRDLKTTWGC-UHFFFAOYSA-N 2-(2-butoxyethoxy)-n,n-bis[2-(2-butoxyethoxy)ethyl]ethanamine Chemical compound CCCCOCCOCCN(CCOCCOCCCC)CCOCCOCCCC RULYNRDLKTTWGC-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NNTVVQGNDMGJKT-UHFFFAOYSA-N ClC1=CC=C(Cl)C(Cl)=C1Cl.ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl.ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl NNTVVQGNDMGJKT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910013698 LiNH2 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical compound [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BVUAIIPVLGTEMU-UHFFFAOYSA-N sodium;2-ethoxyethanolate Chemical compound [Na+].CCOCC[O-] BVUAIIPVLGTEMU-UHFFFAOYSA-N 0.000 description 1
- UIICPZFWHBJNIG-UHFFFAOYSA-N sodium;2-methoxyethanolate Chemical compound [Na+].COCC[O-] UIICPZFWHBJNIG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014607A FR2486068A1 (fr) | 1980-07-01 | 1980-07-01 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
| DE8181400952T DE3160950D1 (en) | 1980-07-01 | 1981-06-16 | Process for the isomerization and/or rearrangement of polychlorobenzenes |
| AT81400952T ATE4699T1 (de) | 1980-07-01 | 1981-06-16 | Verfahren zur isomerisierung und/oder umlagerung von polychlorbenzolen. |
| EP81400952A EP0043303B1 (fr) | 1980-07-01 | 1981-06-16 | Procédé d'isomérisation et/ou de réarrangement de polychlorobenzènes |
| US06/276,481 US4629815A (en) | 1980-07-01 | 1981-06-23 | Isomerization/rearrangement of polychlorobenzenes |
| JP9983081A JPS6015604B2 (ja) | 1980-07-01 | 1981-06-29 | ポリクロルベンゼンの異性化及び転位方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014607A FR2486068A1 (fr) | 1980-07-01 | 1980-07-01 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2486068A1 true FR2486068A1 (fr) | 1982-01-08 |
| FR2486068B1 FR2486068B1 (show.php) | 1982-11-05 |
Family
ID=9243707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8014607A Granted FR2486068A1 (fr) | 1980-07-01 | 1980-07-01 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6015604B2 (show.php) |
| FR (1) | FR2486068A1 (show.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233035A1 (en) * | 1986-02-07 | 1987-08-19 | E.I. Du Pont De Nemours And Company | Catalytic transhalogenation of haloaromatics |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1061506A (fr) * | 1951-10-04 | 1954-04-13 | Union Carbide & Carbon Corp | Isomérisation des dichlorobenzènes |
| US2866829A (en) * | 1956-03-26 | 1958-12-30 | Woodruff Douglas | Isomerization of polychlorobenzenes |
-
1980
- 1980-07-01 FR FR8014607A patent/FR2486068A1/fr active Granted
-
1981
- 1981-06-29 JP JP9983081A patent/JPS6015604B2/ja not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1061506A (fr) * | 1951-10-04 | 1954-04-13 | Union Carbide & Carbon Corp | Isomérisation des dichlorobenzènes |
| US2866829A (en) * | 1956-03-26 | 1958-12-30 | Woodruff Douglas | Isomerization of polychlorobenzenes |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/71 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233035A1 (en) * | 1986-02-07 | 1987-08-19 | E.I. Du Pont De Nemours And Company | Catalytic transhalogenation of haloaromatics |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5770827A (en) | 1982-05-01 |
| JPS6015604B2 (ja) | 1985-04-20 |
| FR2486068B1 (show.php) | 1982-11-05 |
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