DE1013290B - Verfahren zur Herstellung von Insektiziden - Google Patents
Verfahren zur Herstellung von InsektizidenInfo
- Publication number
- DE1013290B DE1013290B DER18257A DER0018257A DE1013290B DE 1013290 B DE1013290 B DE 1013290B DE R18257 A DER18257 A DE R18257A DE R0018257 A DER0018257 A DE R0018257A DE 1013290 B DE1013290 B DE 1013290B
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- endomethylene
- chlorination
- fluorine
- tetrahydrophthalan
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000002917 insecticide Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000460 chlorine Substances 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 238000005660 chlorination reaction Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000406799 Deto Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- LRWHHSXTGZSMSN-UHFFFAOYSA-N Isobenzan Chemical compound ClC1=C(Cl)C2(Cl)C3C(Cl)OC(Cl)C3C1(Cl)C2(Cl)Cl LRWHHSXTGZSMSN-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL213642D NL213642A (enrdf_load_html_response) | 1956-02-04 | ||
| BE554641D BE554641A (enrdf_load_html_response) | 1956-02-04 | ||
| NL93222D NL93222C (enrdf_load_html_response) | 1956-02-04 | ||
| DER18257A DE1013290B (de) | 1956-02-04 | 1956-02-04 | Verfahren zur Herstellung von Insektiziden |
| CH349994D CH349994A (de) | 1956-02-04 | 1956-12-20 | Verfahren zur Herstellung von Insektiziden |
| GB69157A GB847244A (en) | 1956-02-04 | 1957-01-08 | Octahalogeno-endomethylene-tetrahydrophthalans and a process for their production |
| FR1175427D FR1175427A (fr) | 1956-02-04 | 1957-01-09 | Procédé de préparation d'insecticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER18257A DE1013290B (de) | 1956-02-04 | 1956-02-04 | Verfahren zur Herstellung von Insektiziden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1013290B true DE1013290B (de) | 1957-08-08 |
Family
ID=7400168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER18257A Pending DE1013290B (de) | 1956-02-04 | 1956-02-04 | Verfahren zur Herstellung von Insektiziden |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE554641A (enrdf_load_html_response) |
| CH (1) | CH349994A (enrdf_load_html_response) |
| DE (1) | DE1013290B (enrdf_load_html_response) |
| FR (1) | FR1175427A (enrdf_load_html_response) |
| GB (1) | GB847244A (enrdf_load_html_response) |
| NL (2) | NL93222C (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1060869B (de) * | 1958-05-22 | 1959-07-09 | Ruhrchemie Ag | Verfahren zur Herstellung von Derivaten der 4, 5, 6, 7, 10, 10-Hexahalogen-4, 7-endomethylen-4, 7, 8, 9-tetra-hydrophthalane |
| DE1493826B1 (de) * | 1963-12-02 | 1970-07-23 | Hooker Chemical Corp | Verfahren zur Herstellung von halogenierten 4,7-Endomethylen-4,7,8,9-tetrahydrophthalan-5-onen |
-
0
- NL NL213642D patent/NL213642A/xx unknown
- NL NL93222D patent/NL93222C/xx active
- BE BE554641D patent/BE554641A/xx unknown
-
1956
- 1956-02-04 DE DER18257A patent/DE1013290B/de active Pending
- 1956-12-20 CH CH349994D patent/CH349994A/de unknown
-
1957
- 1957-01-08 GB GB69157A patent/GB847244A/en not_active Expired
- 1957-01-09 FR FR1175427D patent/FR1175427A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1060869B (de) * | 1958-05-22 | 1959-07-09 | Ruhrchemie Ag | Verfahren zur Herstellung von Derivaten der 4, 5, 6, 7, 10, 10-Hexahalogen-4, 7-endomethylen-4, 7, 8, 9-tetra-hydrophthalane |
| DE1493826B1 (de) * | 1963-12-02 | 1970-07-23 | Hooker Chemical Corp | Verfahren zur Herstellung von halogenierten 4,7-Endomethylen-4,7,8,9-tetrahydrophthalan-5-onen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL213642A (enrdf_load_html_response) | |
| NL93222C (enrdf_load_html_response) | |
| GB847244A (en) | 1960-09-07 |
| BE554641A (enrdf_load_html_response) | |
| CH349994A (de) | 1960-11-15 |
| FR1175427A (fr) | 1959-03-26 |
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