DE2137553C3 - Verfahren zur Herstellung von Tetrachlorphthalid - Google Patents
Verfahren zur Herstellung von TetrachlorphthalidInfo
- Publication number
- DE2137553C3 DE2137553C3 DE19712137553 DE2137553A DE2137553C3 DE 2137553 C3 DE2137553 C3 DE 2137553C3 DE 19712137553 DE19712137553 DE 19712137553 DE 2137553 A DE2137553 A DE 2137553A DE 2137553 C3 DE2137553 C3 DE 2137553C3
- Authority
- DE
- Germany
- Prior art keywords
- tetrachlorophthalide
- acid
- temperature
- production
- hydrochloric acid
- 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
- 238000000034 method Methods 0.000 title claims description 8
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- WKCSJCNUVUOSSG-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-(chloromethyl)benzoyl chloride Chemical compound ClCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(Cl)=O WKCSJCNUVUOSSG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OHSMSLWDTUCEIP-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-bis(dichloromethyl)benzene Chemical compound ClC(Cl)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(Cl)Cl OHSMSLWDTUCEIP-UHFFFAOYSA-N 0.000 description 1
- GGRDKCIFNAHARJ-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-(hydroxymethyl)benzoic acid Chemical class OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O GGRDKCIFNAHARJ-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 chlorocarbonyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004065 wastewater treatment 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712137553 DE2137553C3 (de) | 1971-07-27 | 1971-07-27 | Verfahren zur Herstellung von Tetrachlorphthalid |
| CH1108072A CH572479A5 (cg-RX-API-DMAC10.html) | 1971-07-27 | 1972-07-25 | |
| JP7422672A JPS563354B1 (cg-RX-API-DMAC10.html) | 1971-07-27 | 1972-07-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712137553 DE2137553C3 (de) | 1971-07-27 | 1971-07-27 | Verfahren zur Herstellung von Tetrachlorphthalid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2137553A1 DE2137553A1 (de) | 1973-02-01 |
| DE2137553B2 DE2137553B2 (de) | 1978-06-22 |
| DE2137553C3 true DE2137553C3 (de) | 1979-02-15 |
Family
ID=5814971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712137553 Expired DE2137553C3 (de) | 1971-07-27 | 1971-07-27 | Verfahren zur Herstellung von Tetrachlorphthalid |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS563354B1 (cg-RX-API-DMAC10.html) |
| CH (1) | CH572479A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2137553C3 (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2614449C3 (de) * | 1976-04-03 | 1979-04-26 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von 3-Chlorphthalid |
-
1971
- 1971-07-27 DE DE19712137553 patent/DE2137553C3/de not_active Expired
-
1972
- 1972-07-25 CH CH1108072A patent/CH572479A5/xx not_active IP Right Cessation
- 1972-07-26 JP JP7422672A patent/JPS563354B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH572479A5 (cg-RX-API-DMAC10.html) | 1976-02-13 |
| DE2137553B2 (de) | 1978-06-22 |
| DE2137553A1 (de) | 1973-02-01 |
| JPS563354B1 (cg-RX-API-DMAC10.html) | 1981-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |