DE2606855C2 - Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid - Google Patents
Verfahren zur Herstellung von Propionsäure-3,4-dichloranilidInfo
- Publication number
- DE2606855C2 DE2606855C2 DE19762606855 DE2606855A DE2606855C2 DE 2606855 C2 DE2606855 C2 DE 2606855C2 DE 19762606855 DE19762606855 DE 19762606855 DE 2606855 A DE2606855 A DE 2606855A DE 2606855 C2 DE2606855 C2 DE 2606855C2
- Authority
- DE
- Germany
- Prior art keywords
- propionic acid
- reaction
- dichloroanilide
- addition
- temperatures
- 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 22
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 235000019260 propionic acid Nutrition 0.000 claims description 22
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 22
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- -1 aryl isocyanates Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical class ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- BSWHYOQBJHPZJM-UHFFFAOYSA-N n-(3,4-dichlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC=C(Cl)C(Cl)=C1 BSWHYOQBJHPZJM-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- TVOMAOCRYBISNK-UHFFFAOYSA-N propanoic acid;propanoyl chloride Chemical compound CCC(O)=O.CCC(Cl)=O TVOMAOCRYBISNK-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606855 DE2606855C2 (de) | 1976-02-20 | 1976-02-20 | Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid |
| GB6470/77A GB1500895A (en) | 1976-02-20 | 1977-02-16 | Process for the preparation of propionic acid 3,4-dichloroanilide |
| CH192477A CH625782A5 (en) | 1976-02-20 | 1977-02-16 | Process for the preparation of 3',4'-dichloro-propionanilide |
| RO7789422A RO73105A (ro) | 1976-02-20 | 1977-02-16 | Procedeu pentru obtinerea 3-4-dicloranilidei propionice |
| IL51478A IL51478A (en) | 1976-02-20 | 1977-02-17 | Process for the preparation of propionic acid 3,4 dichloroanilide |
| BR7701005A BR7701005A (pt) | 1976-02-20 | 1977-02-17 | Processo para a preparacao da 3,4-dicloroanilida de acido propionico |
| NL7701697A NL7701697A (nl) | 1976-02-20 | 1977-02-17 | Werkwijze voor de bereiding van propionzuur- -3.4-dichlooranilide. |
| TR1898177A TR18981A (tr) | 1976-02-20 | 1977-02-17 | Prapionik asid 3,4-dikloro anilid imaline mahsus usul |
| SU772452846A SU612623A3 (ru) | 1976-02-20 | 1977-02-17 | Способ получени 3,4-дихлоранилида пропионовой кислоты |
| ES456028A ES456028A1 (es) | 1976-02-20 | 1977-02-18 | Procedimiento para preparar 3,4-dicloroanilida de acido pro-pionico. |
| DK70977A DK147681C (da) | 1976-02-20 | 1977-02-18 | Fremgangsmaade til fremstilling af propionsyre-3,4-dichloranilid |
| BE175057A BE851583A (fr) | 1976-02-20 | 1977-02-18 | Procede de preparation de 3,4-dichloranilide d'acide propionique |
| IT2047277A IT1086209B (it) | 1976-02-20 | 1977-02-18 | Procedimento per la preparazione di 3,4-dicloro-anilide dell'acido propionico |
| FR7704760A FR2341560A1 (fr) | 1976-02-20 | 1977-02-18 | Procede de preparation de 3,4-dichloranilide d'acide propionique |
| HU77BA3508A HU174259B (hu) | 1976-02-20 | 1977-02-19 | Sposob poluchenija 3,4-dikhloroanilida propionnojj kisloty |
| JP1723277A JPS5943456B2 (ja) | 1976-02-20 | 1977-02-21 | プロピオン酸３，４−ジクロロアニリドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606855 DE2606855C2 (de) | 1976-02-20 | 1976-02-20 | Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2606855A1 DE2606855A1 (de) | 1977-08-25 |
| DE2606855C2 true DE2606855C2 (de) | 1982-12-02 |
Family
ID=5970413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762606855 Expired DE2606855C2 (de) | 1976-02-20 | 1976-02-20 | Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid |
Country Status (16)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643741A1 (de) * | 1968-01-17 | 1971-07-01 | Basf Ag | Verfahren zur Herstellung von Propionsaeure-3,4-dichloranilid |
| CH583529A5 (enrdf_load_stackoverflow) * | 1974-03-28 | 1977-01-14 | Hoechst Ag |
-
1976
- 1976-02-20 DE DE19762606855 patent/DE2606855C2/de not_active Expired
-
1977
- 1977-02-16 CH CH192477A patent/CH625782A5/de not_active IP Right Cessation
- 1977-02-16 RO RO7789422A patent/RO73105A/ro unknown
- 1977-02-16 GB GB6470/77A patent/GB1500895A/en not_active Expired
- 1977-02-17 TR TR1898177A patent/TR18981A/xx unknown
- 1977-02-17 SU SU772452846A patent/SU612623A3/ru active
- 1977-02-17 BR BR7701005A patent/BR7701005A/pt unknown
- 1977-02-17 IL IL51478A patent/IL51478A/xx unknown
- 1977-02-17 NL NL7701697A patent/NL7701697A/xx not_active Application Discontinuation
- 1977-02-18 DK DK70977A patent/DK147681C/da not_active IP Right Cessation
- 1977-02-18 BE BE175057A patent/BE851583A/xx unknown
- 1977-02-18 FR FR7704760A patent/FR2341560A1/fr active Granted
- 1977-02-18 ES ES456028A patent/ES456028A1/es not_active Expired
- 1977-02-18 IT IT2047277A patent/IT1086209B/it active
- 1977-02-19 HU HU77BA3508A patent/HU174259B/hu not_active IP Right Cessation
- 1977-02-21 JP JP1723277A patent/JPS5943456B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IL51478A (en) | 1979-12-30 |
| BR7701005A (pt) | 1977-11-01 |
| NL7701697A (nl) | 1977-08-23 |
| RO73105A (ro) | 1981-09-24 |
| GB1500895A (en) | 1978-02-15 |
| FR2341560A1 (fr) | 1977-09-16 |
| DK70977A (da) | 1977-08-21 |
| TR18981A (tr) | 1978-02-06 |
| IL51478A0 (en) | 1977-04-29 |
| FR2341560B1 (enrdf_load_stackoverflow) | 1981-04-30 |
| CH625782A5 (en) | 1981-10-15 |
| DK147681C (da) | 1985-05-28 |
| JPS52102233A (en) | 1977-08-27 |
| IT1086209B (it) | 1985-05-28 |
| SU612623A3 (ru) | 1978-06-25 |
| DK147681B (da) | 1984-11-12 |
| ES456028A1 (es) | 1978-02-01 |
| DE2606855A1 (de) | 1977-08-25 |
| HU174259B (hu) | 1979-12-28 |
| BE851583A (fr) | 1977-08-18 |
| JPS5943456B2 (ja) | 1984-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination |