DE3049541A1 - Verfahren zur herstellung von 2,4-dichlor- bzw. 2-methyl-4-chlorphenoxyessigsaeure - Google Patents
Verfahren zur herstellung von 2,4-dichlor- bzw. 2-methyl-4-chlorphenoxyessigsaeureInfo
- Publication number
- DE3049541A1 DE3049541A1 DE19803049541 DE3049541A DE3049541A1 DE 3049541 A1 DE3049541 A1 DE 3049541A1 DE 19803049541 DE19803049541 DE 19803049541 DE 3049541 A DE3049541 A DE 3049541A DE 3049541 A1 DE3049541 A1 DE 3049541A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- methylphenoxyacetic
- phenoxyacetic
- suspension
- 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.)
- Withdrawn
Links
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 6
- 229940106681 chloroacetic acid Drugs 0.000 claims description 6
- 239000005574 MCPA Substances 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 3
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003054 catalyst 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803049541 DE3049541A1 (de) | 1980-12-31 | 1980-12-31 | Verfahren zur herstellung von 2,4-dichlor- bzw. 2-methyl-4-chlorphenoxyessigsaeure |
| AT81108843T ATE5812T1 (de) | 1980-12-31 | 1981-10-24 | Verfahren zur herstellung von chlorierten phenoxyalkansaeuren. |
| DE8181108843T DE3161899D1 (en) | 1980-12-31 | 1981-10-24 | Process for the preparation of chlorinated phenoxyalkanoic acids |
| EP81108843A EP0055357B1 (de) | 1980-12-31 | 1981-10-24 | Verfahren zur Herstellung von chlorierten Phenoxyalkansäuren |
| GR66410A GR75381B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-12-31 | 1981-11-03 | |
| IL64475A IL64475A (en) | 1980-12-31 | 1981-12-07 | Preparation of chlorinated phenoxyalkanoic acids |
| IN1392/CAL/81A IN155195B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-12-31 | 1981-12-07 | |
| CA000391845A CA1182473A (en) | 1980-12-31 | 1981-12-09 | Preparation of chlorinated phenoxyalkanoic acids |
| JP56201748A JPS57123139A (en) | 1980-12-31 | 1981-12-16 | Manufacture of chlorinated phenoxyalkanoic acid |
| US06/331,457 US4515985A (en) | 1980-12-31 | 1981-12-16 | Preparation of chlorinated phenoxyalkanoic acids |
| DD81235898A DD201772A5 (de) | 1980-12-31 | 1981-12-17 | Verfahren zur herstellung von chlorierten phenoxyalkansaeuren |
| NZ199356A NZ199356A (en) | 1980-12-31 | 1981-12-22 | Preparing phenoxyacetic acid or alpha-phenoxypropionic acid derivatives |
| CS819668A CS241493B2 (en) | 1980-12-31 | 1981-12-22 | Substituted 4-chlor-phenoxycarboxyl acid production method |
| DK569681A DK157672C (da) | 1980-12-31 | 1981-12-22 | Fremgangsmaade til fremstilling af 2,4-dichlor- eller 2-methyl-4-chlorphenoxyeddikesyre og alfa-2,4-dichlor- eller alfa-2-methyl-4-chlorphenoxypropionsyre |
| AR287982A AR228633A1 (es) | 1980-12-31 | 1981-12-29 | Procedimiento para la obtencion de acidos fenoxial-canoicos clorados |
| HU813987A HU188736B (en) | 1980-12-31 | 1981-12-29 | Process for producing chlorinated phenoxy-alkane-carboxylic acids |
| PL1981234491A PL130576B2 (en) | 1980-12-31 | 1981-12-29 | Process for manufacturing halogenated phenoxyalkanocarboxylic acids |
| IE3088/81A IE52009B1 (en) | 1980-12-31 | 1981-12-30 | Preparation of chlorinated phenoxyalkanoic acids |
| AU79066/81A AU539818B2 (en) | 1980-12-31 | 1981-12-30 | Chlorinated phenoxyalkanoic acids |
| ZA819006A ZA819006B (en) | 1980-12-31 | 1981-12-30 | Preparation of chlorinated phenoxyalkanoic acids |
| BR8108547A BR8108547A (pt) | 1980-12-31 | 1981-12-30 | Processo para obtencao de acidos fenoxialcanoicos clorados |
| ES508452A ES8304911A1 (es) | 1980-12-31 | 1981-12-30 | Procedimiento para la obtencion de acidos fenoxialcanoicos clorados. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803049541 DE3049541A1 (de) | 1980-12-31 | 1980-12-31 | Verfahren zur herstellung von 2,4-dichlor- bzw. 2-methyl-4-chlorphenoxyessigsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3049541A1 true DE3049541A1 (de) | 1982-07-29 |
Family
ID=6120579
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803049541 Withdrawn DE3049541A1 (de) | 1980-12-31 | 1980-12-31 | Verfahren zur herstellung von 2,4-dichlor- bzw. 2-methyl-4-chlorphenoxyessigsaeure |
| DE8181108843T Expired DE3161899D1 (en) | 1980-12-31 | 1981-10-24 | Process for the preparation of chlorinated phenoxyalkanoic acids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181108843T Expired DE3161899D1 (en) | 1980-12-31 | 1981-10-24 | Process for the preparation of chlorinated phenoxyalkanoic acids |
Country Status (21)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2315034C1 (ru) * | 2006-03-15 | 2008-01-20 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством" (НИТИГ) | Способ получения сложных эфиров хлорзамещенных феноксиуксусных кислот (варианты) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101955425B (zh) * | 2009-07-21 | 2012-12-05 | 常明 | 一种无废水生产2.4-d酸的工艺方法 |
| CN102285890A (zh) * | 2011-05-19 | 2011-12-21 | 江苏健谷化工有限公司 | 2-甲基-4-氯苯氧乙酸二甲胺盐的制备工艺 |
| CN104402707A (zh) * | 2014-12-15 | 2015-03-11 | 常熟市新腾化工有限公司 | 一种2,4-二氯苯氧乙酸的制备方法 |
| CN117645540A (zh) | 2018-03-19 | 2024-03-05 | 山东润博生物科技有限公司 | 一种氯代苯氧羧酸酯的制备方法 |
| CN108727196A (zh) * | 2018-07-23 | 2018-11-02 | 安徽华星化工有限公司 | 一种生产2-甲基-4-氯苯氧乙酸的酯类的方法 |
| CN114478314A (zh) * | 2021-12-27 | 2022-05-13 | 江苏长青农化股份有限公司 | 一种稻瘟酰胺的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB688659A (en) * | 1950-09-29 | 1953-03-11 | Danske Gasvaerkers Tjaere Komp | Chlorinated phenoxyacetic acids |
| US2717907A (en) * | 1952-11-12 | 1955-09-13 | Fmc Corp | Preparation of 2, 4, 5-trichlorophenoxy acetic acid |
| FR1116266A (fr) * | 1954-12-10 | 1956-05-07 | Procédé de préparation de l'acide 2-méthyl 4-chloro phénoxy acétique pur | |
| DE1027680B (de) * | 1955-07-13 | 1958-04-10 | Schering Ag | Verfahren zur Herstellung von 2-Methyl-4-chlorphenoxyessigsaeure und ihren Salzen |
| GB855504A (en) * | 1958-03-27 | 1960-11-30 | British Schering Ltd | Preparation of 2-methyl-4-chloro-phenoxy alkanoic acids |
-
1980
- 1980-12-31 DE DE19803049541 patent/DE3049541A1/de not_active Withdrawn
-
1981
- 1981-10-24 EP EP81108843A patent/EP0055357B1/de not_active Expired
- 1981-10-24 DE DE8181108843T patent/DE3161899D1/de not_active Expired
- 1981-10-24 AT AT81108843T patent/ATE5812T1/de not_active IP Right Cessation
- 1981-11-03 GR GR66410A patent/GR75381B/el unknown
- 1981-12-07 IN IN1392/CAL/81A patent/IN155195B/en unknown
- 1981-12-07 IL IL64475A patent/IL64475A/xx not_active IP Right Cessation
- 1981-12-09 CA CA000391845A patent/CA1182473A/en not_active Expired
- 1981-12-16 JP JP56201748A patent/JPS57123139A/ja active Pending
- 1981-12-16 US US06/331,457 patent/US4515985A/en not_active Expired - Lifetime
- 1981-12-17 DD DD81235898A patent/DD201772A5/de not_active IP Right Cessation
- 1981-12-22 DK DK569681A patent/DK157672C/da not_active IP Right Cessation
- 1981-12-22 NZ NZ199356A patent/NZ199356A/en unknown
- 1981-12-22 CS CS819668A patent/CS241493B2/cs unknown
- 1981-12-29 HU HU813987A patent/HU188736B/hu unknown
- 1981-12-29 AR AR287982A patent/AR228633A1/es active
- 1981-12-29 PL PL1981234491A patent/PL130576B2/pl unknown
- 1981-12-30 IE IE3088/81A patent/IE52009B1/en unknown
- 1981-12-30 AU AU79066/81A patent/AU539818B2/en not_active Ceased
- 1981-12-30 ES ES508452A patent/ES8304911A1/es not_active Expired
- 1981-12-30 ZA ZA819006A patent/ZA819006B/xx unknown
- 1981-12-30 BR BR8108547A patent/BR8108547A/pt unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2315034C1 (ru) * | 2006-03-15 | 2008-01-20 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством" (НИТИГ) | Способ получения сложных эфиров хлорзамещенных феноксиуксусных кислот (варианты) |
Also Published As
| Publication number | Publication date |
|---|---|
| GR75381B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-13 |
| DK569681A (da) | 1982-07-01 |
| JPS57123139A (en) | 1982-07-31 |
| AU7906681A (en) | 1982-07-08 |
| CS241493B2 (en) | 1986-03-13 |
| ZA819006B (en) | 1982-12-29 |
| ES508452A0 (es) | 1983-03-16 |
| HU188736B (en) | 1986-05-28 |
| PL130576B2 (en) | 1984-08-31 |
| IE813088L (en) | 1982-06-30 |
| EP0055357B1 (de) | 1984-01-11 |
| AU539818B2 (en) | 1984-10-18 |
| IL64475A (en) | 1986-02-28 |
| NZ199356A (en) | 1984-03-30 |
| PL234491A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-09-13 |
| EP0055357A1 (de) | 1982-07-07 |
| IL64475A0 (en) | 1982-03-31 |
| AR228633A1 (es) | 1983-03-30 |
| ES8304911A1 (es) | 1983-03-16 |
| DK157672B (da) | 1990-02-05 |
| BR8108547A (pt) | 1982-10-19 |
| DK157672C (da) | 1990-07-16 |
| CS966881A2 (en) | 1985-07-16 |
| IE52009B1 (en) | 1987-05-13 |
| US4515985A (en) | 1985-05-07 |
| CA1182473A (en) | 1985-02-12 |
| ATE5812T1 (de) | 1984-01-15 |
| DD201772A5 (de) | 1983-08-10 |
| DE3161899D1 (en) | 1984-02-16 |
| IN155195B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |