FR2475535A1 - Procede de preparation de chlorures d'aryle - Google Patents
Procede de preparation de chlorures d'aryle Download PDFInfo
- Publication number
- FR2475535A1 FR2475535A1 FR8002652A FR8002652A FR2475535A1 FR 2475535 A1 FR2475535 A1 FR 2475535A1 FR 8002652 A FR8002652 A FR 8002652A FR 8002652 A FR8002652 A FR 8002652A FR 2475535 A1 FR2475535 A1 FR 2475535A1
- Authority
- FR
- France
- Prior art keywords
- sep
- iron
- ferrous
- salt
- chloride
- 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
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 35
- 229910021591 Copper(I) chloride Inorganic materials 0.000 title claims abstract description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 23
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 title claims abstract description 23
- 229940045803 cuprous chloride Drugs 0.000 title claims abstract description 22
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 10
- 150000001500 aryl chlorides Chemical class 0.000 title claims abstract description 7
- 150000004982 aromatic amines Chemical class 0.000 title 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012954 diazonium Substances 0.000 claims description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- 150000001989 diazonium salts Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 21
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 claims description 18
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 claims description 18
- 229960002089 ferrous chloride Drugs 0.000 claims description 14
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 14
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 9
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- -1 aromatic primary amine Chemical class 0.000 claims description 4
- 150000002505 iron Chemical class 0.000 claims description 4
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical class [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 claims description 3
- 239000004277 Ferrous carbonate Substances 0.000 claims description 2
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- MCDLETWIOVSGJT-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O MCDLETWIOVSGJT-UHFFFAOYSA-N 0.000 claims description 2
- 229940046149 ferrous bromide Drugs 0.000 claims description 2
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 claims description 2
- 229960004652 ferrous carbonate Drugs 0.000 claims description 2
- 235000019268 ferrous carbonate Nutrition 0.000 claims description 2
- 239000011790 ferrous sulphate Substances 0.000 claims description 2
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 2
- 229910000015 iron(II) carbonate Inorganic materials 0.000 claims description 2
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 229940062993 ferrous oxalate Drugs 0.000 claims 1
- OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 claims 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 15
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 238000010908 decantation Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- AVFLHUZZTDDBBS-UHFFFAOYSA-N 5-chloro-5-methoxycyclohexa-1,3-diene Chemical compound COC1(Cl)CC=CC=C1 AVFLHUZZTDDBBS-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002652A FR2475535A1 (fr) | 1980-02-07 | 1980-02-07 | Procede de preparation de chlorures d'aryle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002652A FR2475535A1 (fr) | 1980-02-07 | 1980-02-07 | Procede de preparation de chlorures d'aryle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475535A1 true FR2475535A1 (fr) | 1981-08-14 |
| FR2475535B1 FR2475535B1 (enExample) | 1983-08-05 |
Family
ID=9238307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8002652A Granted FR2475535A1 (fr) | 1980-02-07 | 1980-02-07 | Procede de preparation de chlorures d'aryle |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2475535A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010102761A1 (de) | 2009-03-12 | 2010-09-16 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von chlor- und bromaromaten |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1141768A (fr) * | 1955-02-24 | 1957-09-09 | Hoechst Ag | Procédé de préparation de 2-chloro-méta-xylène |
-
1980
- 1980-02-07 FR FR8002652A patent/FR2475535A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1141768A (fr) * | 1955-02-24 | 1957-09-09 | Hoechst Ag | Procédé de préparation de 2-chloro-méta-xylène |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010102761A1 (de) | 2009-03-12 | 2010-09-16 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von chlor- und bromaromaten |
| CN102395546A (zh) * | 2009-03-12 | 2012-03-28 | 拜耳作物科学公司 | 制备氯代和溴代芳烃的方法 |
| JP2012520243A (ja) * | 2009-03-12 | 2012-09-06 | バイエル・クロップサイエンス・アーゲー | クロロ芳香族化合物及びブロモ芳香族化合物を調整する方法 |
| US8334417B2 (en) | 2009-03-12 | 2012-12-18 | Bayer Cropscience Ag | Process for preparing chloro- and bromoaromatics |
| CN102395546B (zh) * | 2009-03-12 | 2014-03-12 | 拜耳作物科学公司 | 制备氯代和溴代芳烃的方法 |
| TWI465414B (zh) * | 2009-03-12 | 2014-12-21 | Bayer Cropscience Ag | 製備氯基－及溴基芳族化合物之方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2475535B1 (enExample) | 1983-08-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0532610A (ja) | １，２−ナフトキノンジアジド−５−スルホニルクロリドの製造方法 | |
| FR2475535A1 (fr) | Procede de preparation de chlorures d'aryle | |
| EA001630B1 (ru) | Способ получения n-замещенных 3-гидроксипиразолов | |
| JPS63101339A (ja) | トリフルオロメチルヨージドの製法 | |
| FR2541677A1 (fr) | Procede de preparation du chlorure de 4-chlorobenzene sulfonyle | |
| BE1005256A3 (fr) | Synthese des perfluoroalkyl-2 ethanethiols. | |
| US2821549A (en) | Production of nuclear sulfonated vinyl aromatic compounds | |
| CN105189447B (zh) | 制造硝基苯化合物的方法 | |
| CA2355358C (fr) | Procede de preparation de para-trifluoromethylanilines polyhalogenees | |
| JPS6340184B2 (enExample) | ||
| EP0020281B1 (fr) | Préparation de benzoxazolone | |
| FR2745286A1 (fr) | Synthese de composes organiques iodo-fluores | |
| EP1175393A1 (en) | Process for the preparation of phenylhydrazines | |
| SU1128836A3 (ru) | Способ получени сахарина | |
| EP0004247A1 (fr) | Procédé d'obtention de sels d'aryldiazonium à partir de vapeurs nitreuses riches en oxyde azotique, solutions aqueuses de ces sels et leur utilisation pour l'obtention de composés amino-azo-aromatiques | |
| KR100294117B1 (ko) | 4-니트로소디페닐아민또는그의염의제조방법 | |
| EP0168296B1 (fr) | Procédé de préparation de l'amino-3 triazole-1,2,4 | |
| PT85211B (pt) | Processo para a preparacao de n-amino-3-aza-biciclo 3,3,0 octano | |
| JPH0139A (ja) | ２，４−ジクロル−３−メチル−６−タ−シャリ−ブチルフェノ−ルの製造方法 | |
| US4293720A (en) | Process for preparation of hydroperoxides | |
| US3985759A (en) | Process for preparing 2-amino-5-chloropyridine | |
| EP0118971A1 (en) | Process for the preparation of cyanotetrachlorobenzenes | |
| WO2000021922A2 (en) | Chemical processes | |
| FR2540108A1 (fr) | Procede de preparation de perhalogenoalkylthioethers | |
| EP0018931B1 (fr) | Préparation de benzoxazolone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |