DE2800324C2 - - Google Patents
Info
- Publication number
- DE2800324C2 DE2800324C2 DE2800324A DE2800324A DE2800324C2 DE 2800324 C2 DE2800324 C2 DE 2800324C2 DE 2800324 A DE2800324 A DE 2800324A DE 2800324 A DE2800324 A DE 2800324A DE 2800324 C2 DE2800324 C2 DE 2800324C2
- Authority
- DE
- Germany
- Prior art keywords
- copper
- weight
- parts
- dichlorophenol
- reaction
- 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.)
- Expired
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000001879 copper Chemical class 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 230000020477 pH reduction Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 6
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 claims description 4
- OVXVQBCRONSPDC-UHFFFAOYSA-N 2-bromo-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Br)=C1 OVXVQBCRONSPDC-UHFFFAOYSA-N 0.000 claims description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000047 product Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- HVNYYRLZCAOJQN-UHFFFAOYSA-N 1-bromo-3,6-dichlorocyclohexa-2,4-dien-1-ol Chemical compound OC1(Br)C=C(Cl)C=CC1Cl HVNYYRLZCAOJQN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ISHYFWKKWKXXPL-UHFFFAOYSA-N 1-bromo-2,4-dichlorobenzene Chemical compound ClC1=CC=C(Br)C(Cl)=C1 ISHYFWKKWKXXPL-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
- CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 1
- IJCCOEGCVILSMZ-UHFFFAOYSA-L copper;dichlorate Chemical compound [Cu+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O IJCCOEGCVILSMZ-UHFFFAOYSA-L 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- QDLOTAGCTPEFOF-UHFFFAOYSA-J copper;dipotassium;tetrachloride;dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cl-].[Cl-].[K+].[K+].[Cu+2] QDLOTAGCTPEFOF-UHFFFAOYSA-J 0.000 description 1
- RGZGHMSJVAQDQO-UHFFFAOYSA-L copper;selenate Chemical compound [Cu+2].[O-][Se]([O-])(=O)=O RGZGHMSJVAQDQO-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/757,527 US4094913A (en) | 1977-01-07 | 1977-01-07 | Process for the preparation of 2,5-dichlorophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2800324A1 DE2800324A1 (de) | 1978-07-13 |
| DE2800324C2 true DE2800324C2 (en, 2012) | 1988-09-15 |
Family
ID=25048154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782800324 Granted DE2800324A1 (de) | 1977-01-07 | 1978-01-04 | Verfahren zur herstellung von 2,5-dichlorphenol |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4094913A (en, 2012) |
| JP (1) | JPS5387328A (en, 2012) |
| AR (1) | AR213555A1 (en, 2012) |
| AT (1) | AT351508B (en, 2012) |
| AU (1) | AU513662B2 (en, 2012) |
| BE (1) | BE862463A (en, 2012) |
| CA (1) | CA1077520A (en, 2012) |
| CH (1) | CH631956A5 (en, 2012) |
| DE (1) | DE2800324A1 (en, 2012) |
| FR (1) | FR2376836A1 (en, 2012) |
| GB (1) | GB1563078A (en, 2012) |
| IL (1) | IL53587A (en, 2012) |
| MX (1) | MX5201E (en, 2012) |
| NL (1) | NL7800029A (en, 2012) |
| ZA (1) | ZA777328B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4262152A (en) * | 1979-05-02 | 1981-04-14 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
| US4259510A (en) * | 1979-05-02 | 1981-03-31 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
| CA1162571A (en) * | 1980-06-11 | 1984-02-21 | Velsicol Chemical Corporation | Process for preparing high assay dicamba |
| FR2609711B1 (fr) * | 1987-01-21 | 1989-06-16 | Rhone Poulenc Chimie | Procede de preparation d'hydroxybiphenyles |
| FR2610924B1 (fr) * | 1987-02-12 | 1990-05-04 | Rhone Poulenc Chimie | Procede de preparation d'hydroxybiphenyles |
| US4774368A (en) * | 1987-05-21 | 1988-09-27 | Ethyl Corporation | Process for making meta-alkyl phenols |
| US5227536A (en) * | 1991-09-20 | 1993-07-13 | The Dow Chemical Company | Process for preparing hydroxybenzocyclobutenes |
| CN1035324C (zh) * | 1995-02-16 | 1997-07-02 | 建湖县有机化工厂 | 由邻氯苯酚生产2.6－二氯苯酚的方法 |
| US9643909B2 (en) * | 2013-10-04 | 2017-05-09 | Basf Se | Process for hydrolyzing 1,2,4-trihalobenzene |
| WO2015049360A1 (en) | 2013-10-04 | 2015-04-09 | Basf Se | Selective hydrolysis and alcoholysis of chlorinated benzenes |
| US10087133B2 (en) | 2013-12-11 | 2018-10-02 | Basf Se | Process for providing dihalogen substituted salicylic acid derivatives |
| AR100506A1 (es) | 2014-05-19 | 2016-10-12 | Basf Se | Proceso de obtención del herbicida dicamba |
| CN105884582A (zh) * | 2016-04-29 | 2016-08-24 | 四川福思达生物技术开发有限责任公司 | 一种2,5-二氯苯酚的合成工艺 |
| CN105801334A (zh) * | 2016-05-03 | 2016-07-27 | 四川福思达生物技术开发有限责任公司 | 一种2,5-二氯苯酚的合成方法 |
| CN105968000B (zh) * | 2016-05-06 | 2019-03-05 | 四川福思达生物技术开发有限责任公司 | 一种制备麦草畏的方法 |
| CN105859508B (zh) * | 2016-05-06 | 2019-03-05 | 四川福思达生物技术开发有限责任公司 | 一种制备麦草畏的工艺 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE349794C (de) * | 1914-07-29 | 1922-03-09 | Anilin Fabrikation Ag | Verfahren zur Darstellung von Di- und Polyhalogensubstitutionsprodukten einwertiger Phenole |
| US2126648A (en) * | 1936-09-09 | 1938-08-09 | Pennsyivania Coal Products Com | Process of producing halogenated phenols |
| US2615923A (en) * | 1950-05-02 | 1952-10-28 | Olin Mathieson | Manufacture of sodium chlorophenate |
| US2778857A (en) * | 1954-04-26 | 1957-01-22 | Dow Chemical Co | Method for making 5-chloro-omicron-cresol and 4, 5-dichloro-omicron-cresol |
| US2950325A (en) * | 1958-06-06 | 1960-08-23 | Dow Chemical Co | Process for making fluorophenols |
| FR1216575A (fr) * | 1958-12-10 | 1960-04-26 | Olin Mathieson | Procédé de préparation du para-fluorophénol |
| US3412145A (en) * | 1964-07-07 | 1968-11-19 | Velsicol Chemical Corp | Separation of chlorinated phenol isomers |
| US3461174A (en) * | 1965-10-21 | 1969-08-12 | Velsicol Chemical Corp | Process for preparing 2,5-dichloro-4-bromophenol |
| BE691919A (en, 2012) * | 1966-12-28 | 1967-06-28 | ||
| FR2097495A5 (en) * | 1970-07-08 | 1972-03-03 | Centerchem Inc | 2,4,5-trichlorphenol - in high yield and high purity from 1,2,4,5-tet |
-
1977
- 1977-01-07 US US05/757,527 patent/US4094913A/en not_active Expired - Lifetime
- 1977-12-06 CA CA292,493A patent/CA1077520A/en not_active Expired
- 1977-12-08 ZA ZA00777328A patent/ZA777328B/xx unknown
- 1977-12-12 IL IL53587A patent/IL53587A/xx unknown
- 1977-12-21 AR AR270455A patent/AR213555A1/es active
- 1977-12-28 CH CH1615377A patent/CH631956A5/de not_active IP Right Cessation
- 1977-12-29 BE BE183961A patent/BE862463A/xx not_active IP Right Cessation
-
1978
- 1978-01-02 NL NL7800029A patent/NL7800029A/xx not_active Application Discontinuation
- 1978-01-04 DE DE19782800324 patent/DE2800324A1/de active Granted
- 1978-01-05 AT AT8478A patent/AT351508B/de not_active IP Right Cessation
- 1978-01-05 FR FR7800248A patent/FR2376836A1/fr active Granted
- 1978-01-06 AU AU32227/78A patent/AU513662B2/en not_active Expired
- 1978-01-06 MX MX786756U patent/MX5201E/es unknown
- 1978-01-06 GB GB438/78A patent/GB1563078A/en not_active Expired
- 1978-01-07 JP JP79178A patent/JPS5387328A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2800324A1 (de) | 1978-07-13 |
| IL53587A0 (en) | 1978-03-10 |
| US4094913A (en) | 1978-06-13 |
| AU513662B2 (en) | 1980-12-11 |
| FR2376836B1 (en, 2012) | 1984-06-08 |
| FR2376836A1 (fr) | 1978-08-04 |
| CA1077520A (en) | 1980-05-13 |
| ATA8478A (de) | 1979-01-15 |
| AU3222778A (en) | 1979-07-12 |
| MX5201E (es) | 1983-04-25 |
| JPS6121211B2 (en, 2012) | 1986-05-26 |
| AR213555A1 (es) | 1979-02-15 |
| CH631956A5 (de) | 1982-09-15 |
| NL7800029A (nl) | 1978-07-11 |
| AT351508B (de) | 1979-07-25 |
| JPS5387328A (en) | 1978-08-01 |
| BE862463A (fr) | 1978-04-14 |
| IL53587A (en) | 1981-07-31 |
| ZA777328B (en) | 1978-10-25 |
| GB1563078A (en) | 1980-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: PRINZ, E., DIPL.-ING. LEISER, G., DIPL.-ING., PAT. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |