PL130576B2 - Process for manufacturing halogenated phenoxyalkanocarboxylic acids - Google Patents
Process for manufacturing halogenated phenoxyalkanocarboxylic acids Download PDFInfo
- Publication number
- PL130576B2 PL130576B2 PL1981234491A PL23449181A PL130576B2 PL 130576 B2 PL130576 B2 PL 130576B2 PL 1981234491 A PL1981234491 A PL 1981234491A PL 23449181 A PL23449181 A PL 23449181A PL 130576 B2 PL130576 B2 PL 130576B2
- Authority
- PL
- Poland
- Prior art keywords
- acid
- water
- suspension
- chlorine
- phenoxypropionic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 239000002253 acid Substances 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 3
- 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 48
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 239000000725 suspension Substances 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 20
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 claims description 19
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 16
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 14
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- YIGXGYDKDDWZLS-UHFFFAOYSA-N 2-(2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C YIGXGYDKDDWZLS-UHFFFAOYSA-N 0.000 claims description 9
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 9
- 229940106681 chloroacetic acid Drugs 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000005574 MCPA Substances 0.000 claims description 6
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 3
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 2
- -1 alkali metal salts Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003809 water extraction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 4
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 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 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing 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
- C07C51/347—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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| PL234491A2 PL234491A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-09-13 |
| PL130576B2 true PL130576B2 (en) | 1984-08-31 |
Family
ID=6120579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981234491A PL130576B2 (en) | 1980-12-31 | 1981-12-29 | Process for manufacturing halogenated phenoxyalkanocarboxylic acids |
Country Status (21)
Families Citing this family (7)
| 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) |
| 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
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 |
| 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 |
| DE3049541A1 (de) | 1982-07-29 |
| DE3161899D1 (en) | 1984-02-16 |
| IN155195B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-01-12 |
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