DE3206006A1 - Verfahren zur herstellung von dihalogen-vinyl-cyclopropancarbonsaeuren - Google Patents
Verfahren zur herstellung von dihalogen-vinyl-cyclopropancarbonsaeurenInfo
- Publication number
- DE3206006A1 DE3206006A1 DE19823206006 DE3206006A DE3206006A1 DE 3206006 A1 DE3206006 A1 DE 3206006A1 DE 19823206006 DE19823206006 DE 19823206006 DE 3206006 A DE3206006 A DE 3206006A DE 3206006 A1 DE3206006 A1 DE 3206006A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- acid ester
- hydrolysis
- phase
- weight
- 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
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 238000006460 hydrolysis reaction Methods 0.000 claims description 22
- 230000007062 hydrolysis Effects 0.000 claims description 21
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 13
- 239000012071 phase Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000001256 steam distillation Methods 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000010956 selective crystallization Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000012875 nonionic emulsifier Substances 0.000 claims 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000002728 pyrethroid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- -1 cyclopropanecarboxylic acid ester Chemical class 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 240000005265 Lupinus mutabilis Species 0.000 description 1
- 235000008755 Lupinus mutabilis Nutrition 0.000 description 1
- 235000019095 Sechium edule Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- QPTWKDNRYCGMJM-UHFFFAOYSA-N ethyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)Cl)C1(C)C QPTWKDNRYCGMJM-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU81411A HU185030B (en) | 1981-02-20 | 1981-02-20 | Process for producing isomere mixtures of pure dichloro-vinyl-cyclopropane-carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3206006A1 true DE3206006A1 (de) | 1982-09-16 |
| DE3206006C2 DE3206006C2 (en, 2012) | 1987-12-03 |
Family
ID=10949493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823206006 Granted DE3206006A1 (de) | 1981-02-20 | 1982-02-19 | Verfahren zur herstellung von dihalogen-vinyl-cyclopropancarbonsaeuren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4419524A (en, 2012) |
| JP (1) | JPS57150635A (en, 2012) |
| CH (1) | CH655300A5 (en, 2012) |
| DE (1) | DE3206006A1 (en, 2012) |
| FR (1) | FR2500443B1 (en, 2012) |
| GB (1) | GB2095234B (en, 2012) |
| HU (1) | HU185030B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047581A (en) * | 1989-08-25 | 1991-09-10 | Fmc Corporation | Isolation of cis-isomers from isomeric mixtures of cis/transcyclopropanecarboxylates |
| ATE115536T1 (de) * | 1990-06-14 | 1994-12-15 | Lonza Ag | Verfahren zur racematspaltung von 2,2- dimethylcyclopropancarbonsäure. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| JPS5623975B2 (en, 2012) * | 1972-11-08 | 1981-06-03 | ||
| JPS533386B2 (en, 2012) * | 1972-11-13 | 1978-02-06 | ||
| DE2713538A1 (de) * | 1977-03-26 | 1978-09-28 | Bayer Ag | Verfahren zur trennung stereoisomerer cyclischer carbonsaeuren |
| DE2965745D1 (en) * | 1978-10-27 | 1983-07-28 | Ici Plc | Process of separating cis and trans isomers of cyclopropane carboxylic acids |
| FR2455024A1 (fr) * | 1979-04-03 | 1980-11-21 | Roussel Uclaf | Nouveau procede de dedoublement des acides d,l-cis 2,2-dimethyl 3-(2',2'-dihalovinyl) cyclopropane-1-carboxylique |
| IT1120780B (it) * | 1979-06-06 | 1986-03-26 | Montedison Spa | Procedimento per la preparazione di alcool 3,3-dimetil-allilico |
| JPS565435A (en) * | 1979-06-26 | 1981-01-20 | Nissan Chem Ind Ltd | Trans-2,2-dimethyl-3- p-substituted phenyl -cyclopropane- carboxylic acid and its preparation |
| US4288610A (en) * | 1980-02-25 | 1981-09-08 | Stauffer Chemical Company | Purification of pyrethroid intermediate compounds by selective partial saponification |
-
1981
- 1981-02-20 HU HU81411A patent/HU185030B/hu not_active IP Right Cessation
-
1982
- 1982-02-19 FR FR8202774A patent/FR2500443B1/fr not_active Expired
- 1982-02-19 US US06/350,424 patent/US4419524A/en not_active Expired - Lifetime
- 1982-02-19 CH CH1053/82A patent/CH655300A5/de not_active IP Right Cessation
- 1982-02-19 GB GB8204885A patent/GB2095234B/en not_active Expired
- 1982-02-19 JP JP57024636A patent/JPS57150635A/ja active Granted
- 1982-02-19 DE DE19823206006 patent/DE3206006A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH655300A5 (de) | 1986-04-15 |
| US4419524A (en) | 1983-12-06 |
| GB2095234A (en) | 1982-09-29 |
| JPH0521904B2 (en, 2012) | 1993-03-25 |
| FR2500443B1 (fr) | 1986-05-02 |
| FR2500443A1 (fr) | 1982-08-27 |
| GB2095234B (en) | 1984-12-05 |
| HU185030B (en) | 1984-11-28 |
| JPS57150635A (en) | 1982-09-17 |
| DE3206006C2 (en, 2012) | 1987-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: LOTTERHOS, H., DIPL.-ING. DR.-ING. BARTSCH, E., DIPL.-CHEM. DR.RER.NAT., PAT.-ANWAELTE, 6000 FRANKFURT |
|
| 8339 | Ceased/non-payment of the annual fee |