FR2505817A1 - Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes - Google Patents
Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes Download PDFInfo
- Publication number
- FR2505817A1 FR2505817A1 FR8109392A FR8109392A FR2505817A1 FR 2505817 A1 FR2505817 A1 FR 2505817A1 FR 8109392 A FR8109392 A FR 8109392A FR 8109392 A FR8109392 A FR 8109392A FR 2505817 A1 FR2505817 A1 FR 2505817A1
- Authority
- FR
- France
- Prior art keywords
- benzene
- process according
- alkali metal
- tetrachlorobenzene
- trichloro
- 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 14
- 238000006243 chemical reaction Methods 0.000 title claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 title claims description 10
- 150000001340 alkali metals Chemical class 0.000 title description 2
- 239000002585 base Substances 0.000 title 1
- 239000008139 complexing agent Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 26
- 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 25
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 alkali metal amide Chemical class 0.000 claims abstract description 18
- 230000000536 complexating effect Effects 0.000 claims abstract description 11
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical class ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims abstract description 10
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 62
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229940066528 trichloroacetate Drugs 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 12
- 238000006317 isomerization reaction Methods 0.000 abstract description 8
- 230000008707 rearrangement Effects 0.000 abstract description 8
- 150000004816 dichlorobenzenes Chemical class 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 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
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QZYNWJQFTJXIRN-UHFFFAOYSA-N 1,2,3,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1 QZYNWJQFTJXIRN-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FWAJPSIPOULHHH-UHFFFAOYSA-N 1,2,4-tribromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1 FWAJPSIPOULHHH-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
- 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
- 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
- SKURLYPVXDWOTB-UHFFFAOYSA-N CC/C=[O]/CCN Chemical compound CC/C=[O]/CCN SKURLYPVXDWOTB-UHFFFAOYSA-N 0.000 description 1
- ZTLLLVIQLZNAGX-UHFFFAOYSA-N CCCOCC[O]1(CC2)=CCCN2CC1 Chemical compound CCCOCC[O]1(CC2)=CCCN2CC1 ZTLLLVIQLZNAGX-UHFFFAOYSA-N 0.000 description 1
- 241000906683 Nantis Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000000010 nanu Nutrition 0.000 description 1
- 244000082862 nanu Species 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8109392A FR2505817A1 (fr) | 1981-05-12 | 1981-05-12 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
| EP81400952A EP0043303B1 (fr) | 1980-07-01 | 1981-06-16 | Procédé d'isomérisation et/ou de réarrangement de polychlorobenzènes |
| AT81400952T ATE4699T1 (de) | 1980-07-01 | 1981-06-16 | Verfahren zur isomerisierung und/oder umlagerung von polychlorbenzolen. |
| DE8181400952T DE3160950D1 (en) | 1980-07-01 | 1981-06-16 | Process for the isomerization and/or rearrangement of polychlorobenzenes |
| US06/276,481 US4629815A (en) | 1980-07-01 | 1981-06-23 | Isomerization/rearrangement of polychlorobenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8109392A FR2505817A1 (fr) | 1981-05-12 | 1981-05-12 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2505817A1 true FR2505817A1 (fr) | 1982-11-19 |
| FR2505817B1 FR2505817B1 (enrdf_load_stackoverflow) | 1983-07-18 |
Family
ID=9258322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8109392A Granted FR2505817A1 (fr) | 1980-07-01 | 1981-05-12 | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2505817A1 (enrdf_load_stackoverflow) |
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 |
-
1981
- 1981-05-12 FR FR8109392A patent/FR2505817A1/fr active Granted
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 |
|---|---|
| FR2505817B1 (enrdf_load_stackoverflow) | 1983-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |