FR2513991A1 - Procede de chloration de metadihalogenobenzenes - Google Patents
Procede de chloration de metadihalogenobenzenes Download PDFInfo
- Publication number
- FR2513991A1 FR2513991A1 FR8118585A FR8118585A FR2513991A1 FR 2513991 A1 FR2513991 A1 FR 2513991A1 FR 8118585 A FR8118585 A FR 8118585A FR 8118585 A FR8118585 A FR 8118585A FR 2513991 A1 FR2513991 A1 FR 2513991A1
- Authority
- FR
- France
- Prior art keywords
- process according
- compound
- chr
- amide
- formula
- 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
- 238000000034 method Methods 0.000 title claims description 30
- 238000005660 chlorination reaction Methods 0.000 title claims description 18
- -1 alkali metal amide Chemical class 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000000536 complexating effect Effects 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 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 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003352 sequestering agent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000008139 complexing agent Substances 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 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 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001412 amines Chemical class 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 5
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 4
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 238000003822 preparative gas chromatography Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VLVCVSDHHLWKKT-UHFFFAOYSA-N 1,3-difluoronaphthalene Chemical compound C1=CC=CC2=CC(F)=CC(F)=C21 VLVCVSDHHLWKKT-UHFFFAOYSA-N 0.000 description 3
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 3
- NPXCSDPOOVOVDQ-UHFFFAOYSA-N 1,2-dichloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1Cl NPXCSDPOOVOVDQ-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- XPHNTJXRSWNSNF-UHFFFAOYSA-N 1,3-dichloro-2,4-difluorobenzene Chemical compound FC1=CC=C(Cl)C(F)=C1Cl XPHNTJXRSWNSNF-UHFFFAOYSA-N 0.000 description 1
- ZBNCSBMIRFHJEL-UHFFFAOYSA-N 1-chloro-2,3-difluorobenzene Chemical compound FC1=CC=CC(Cl)=C1F ZBNCSBMIRFHJEL-UHFFFAOYSA-N 0.000 description 1
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 1
- MPXDAIBTYWGBSL-UHFFFAOYSA-N 2,4-difluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1F MPXDAIBTYWGBSL-UHFFFAOYSA-N 0.000 description 1
- XZGIHWAIIZHXKX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-n,n-bis[2-(2-ethoxyethoxy)ethyl]ethanamine Chemical compound CCOCCOCCN(CCOCCOCC)CCOCCOCC XZGIHWAIIZHXKX-UHFFFAOYSA-N 0.000 description 1
- UTMXAQHUJBHEGB-UHFFFAOYSA-N 2-chloro-1,3-difluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(Cl)=C1F UTMXAQHUJBHEGB-UHFFFAOYSA-N 0.000 description 1
- OTZQYBFTOANOJO-UHFFFAOYSA-N 2-chloro-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Cl OTZQYBFTOANOJO-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000379208 Latris Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010668 complexation reaction Methods 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
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 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 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
- 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
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8118585A FR2513991A1 (fr) | 1981-10-02 | 1981-10-02 | Procede de chloration de metadihalogenobenzenes |
| EP82401695A EP0076718B1 (fr) | 1981-10-02 | 1982-09-20 | Procédé de chloration de métadihalogénobenzènes |
| DE8282401695T DE3260733D1 (en) | 1981-10-02 | 1982-09-20 | Process for the halogenation of metadihalogenobenzenes |
| AT82401695T ATE9320T1 (de) | 1981-10-02 | 1982-09-20 | Verfahren zur halogenierung von metadihalogenobenzolen. |
| JP57168676A JPS6049609B2 (ja) | 1981-10-02 | 1982-09-29 | ｍ−ジハロゲノベンゼン類の塩素化方法 |
| US06/428,451 US4417081A (en) | 1981-10-02 | 1982-09-30 | Selective 2-chlorination of meta-dihalobenzenes |
| BR8205729A BR8205729A (pt) | 1981-10-02 | 1982-09-30 | Processo de cloracao de metadi-halogenobenzenos |
| CA000412663A CA1182844A (fr) | 1981-10-02 | 1982-10-01 | Procede de chloration de metadihalogenobenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8118585A FR2513991A1 (fr) | 1981-10-02 | 1981-10-02 | Procede de chloration de metadihalogenobenzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2513991A1 true FR2513991A1 (fr) | 1983-04-08 |
| FR2513991B1 FR2513991B1 (enExample) | 1983-12-09 |
Family
ID=9262686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8118585A Granted FR2513991A1 (fr) | 1981-10-02 | 1981-10-02 | Procede de chloration de metadihalogenobenzenes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4417081A (enExample) |
| EP (1) | EP0076718B1 (enExample) |
| JP (1) | JPS6049609B2 (enExample) |
| AT (1) | ATE9320T1 (enExample) |
| BR (1) | BR8205729A (enExample) |
| CA (1) | CA1182844A (enExample) |
| DE (1) | DE3260733D1 (enExample) |
| FR (1) | FR2513991A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8716587D0 (en) * | 1987-07-14 | 1987-08-19 | Shell Int Research | Preparing thiophene derivatives |
| US5235020A (en) * | 1991-12-31 | 1993-08-10 | Amoco Corporation | Process for preparation of poly(aryl ether) polymers by acyclic catalysts |
| DE4445548A1 (de) * | 1994-12-20 | 1996-06-27 | Bayer Ag | Verfahren zur Herstellung von 3-Fluor-4,6-dichlortoluol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186153A (en) * | 1978-01-16 | 1980-01-29 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
| US4205014A (en) * | 1978-01-16 | 1980-05-27 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843637A (en) * | 1952-09-23 | 1958-07-15 | Ethyl Corp | Manufacture of tetrachlorobenzene |
-
1981
- 1981-10-02 FR FR8118585A patent/FR2513991A1/fr active Granted
-
1982
- 1982-09-20 DE DE8282401695T patent/DE3260733D1/de not_active Expired
- 1982-09-20 AT AT82401695T patent/ATE9320T1/de not_active IP Right Cessation
- 1982-09-20 EP EP82401695A patent/EP0076718B1/fr not_active Expired
- 1982-09-29 JP JP57168676A patent/JPS6049609B2/ja not_active Expired
- 1982-09-30 BR BR8205729A patent/BR8205729A/pt unknown
- 1982-09-30 US US06/428,451 patent/US4417081A/en not_active Expired - Fee Related
- 1982-10-01 CA CA000412663A patent/CA1182844A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186153A (en) * | 1978-01-16 | 1980-01-29 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
| US4205014A (en) * | 1978-01-16 | 1980-05-27 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5874625A (ja) | 1983-05-06 |
| EP0076718B1 (fr) | 1984-09-12 |
| JPS6049609B2 (ja) | 1985-11-02 |
| CA1182844A (fr) | 1985-02-19 |
| BR8205729A (pt) | 1983-09-06 |
| DE3260733D1 (en) | 1984-10-18 |
| FR2513991B1 (enExample) | 1983-12-09 |
| EP0076718A1 (fr) | 1983-04-13 |
| ATE9320T1 (de) | 1984-09-15 |
| US4417081A (en) | 1983-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0021868B1 (fr) | Procédé de préparation d'éthers diaryliques | |
| FR2662439A1 (fr) | Reactif et procede de perfluoroalkylation de substrats nucleophiles par les perfluoroalcanesulfinates de sodium en milieu oxydant. | |
| EP0021927B1 (fr) | Procédé de préparation d'éthers aryliques | |
| FR2513991A1 (fr) | Procede de chloration de metadihalogenobenzenes | |
| EP0049186B1 (fr) | Procédé de préparation de fluorobenzonitriles | |
| EP0043303B1 (fr) | Procédé d'isomérisation et/ou de réarrangement de polychlorobenzènes | |
| EP0060171B1 (fr) | Procédé de N-alkylation de composés organiques azotés | |
| EP0429331B1 (fr) | Synthèse des bromures de perfluoroalkyle | |
| EP0069001B1 (fr) | Procédé de préparation de dérivés de la tétrahydro-5,6,7,7a 4H-thiéno (3,2-C) pyridinone-2 | |
| EP0115985B1 (fr) | Procédé d'alkylation de dérives benzéniques halogènes et/ou trifluorométhyles | |
| EP0200657A1 (fr) | Procédé de préparation de trifluoroéthoxy ou trifluoroéthylthiobenzènes | |
| EP0435714B1 (fr) | Procédé de préparation de chlorures d'acides carboxyliques chlorés | |
| EP0267066B1 (fr) | Nouveaux organomagnésiens sous forme solide, leur procédé de préparation et leur utilisation | |
| EP0098783B1 (fr) | Procédé de préparation de halogéno anilines | |
| FR2643900A1 (fr) | Fonctionnalisation en position n + 1 de derives aryliques disubstitues en position n et n + 2 | |
| EP0822184B1 (fr) | Procédé de préparation de lactames N-substitués | |
| EP0117186B1 (fr) | Procédé de préparation de dérivés du cyclopropane | |
| FR2505327A1 (fr) | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues | |
| EP0052558B1 (fr) | Nouveaux bromopolyfluoroalkyl éthers aromatiques et leur procédé de préparation | |
| EP0035927B1 (fr) | Procédé de préparation de chloroalkoxybenzènes | |
| EP0338898B1 (fr) | Procédé de préparation d'un dérivé mono-bromé en ortho du phénol | |
| FR2540108A1 (fr) | Procede de preparation de perhalogenoalkylthioethers | |
| EP0102305A1 (fr) | Procédé de préparation d'anilines métachlorées | |
| EP0526281A1 (fr) | Procédé de synthèse de pyrazoles 1,4-disubstitués | |
| FR2505817A1 (fr) | Procede d'isomerisation et/ou de rearrangement de polychlorobenzenes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |