CN102329255B - Process for synthesizing fomesafen through directional nitration - Google Patents
Process for synthesizing fomesafen through directional nitration Download PDFInfo
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- CN102329255B CN102329255B CN201110337238XA CN201110337238A CN102329255B CN 102329255 B CN102329255 B CN 102329255B CN 201110337238X A CN201110337238X A CN 201110337238XA CN 201110337238 A CN201110337238 A CN 201110337238A CN 102329255 B CN102329255 B CN 102329255B
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Abstract
The invention relates to a method for synthesizing weedicide fomesafen with high efficiency, low toxicity and low residue. The method comprises the following steps of: reacting 3-(2-chlorine-a,a,a-trifluoro para-tolyloxy)-benzoic acid serving as a raw material with mixed acid (nitric acid and sulfuric acid) under the conditions of a mixed solvent (methylbenzene and acetic ether) serving as a solvent and a novel directional catalyst (aluminum silicon complex) to obtain 5-(2-chlorine-2,2,2-trifluoro-para-tolyloxy)-2-nitrobenzoic acid; and synthesizing the fomesafen.
Description
Technical field
The present invention relates to the new synthesis technology of agricultural herbicide fomesafen.
Background technology
A kind of soybean, Peanut Fields herbicide after seedling with high selectivity of fomesafen, can effectively prevent and kill off soybean, Peanut Fields broadleaf weeds and Rhizoma Cyperi, gramineous weeds is also had certain preventive effect, have broad weed-killing spectrum, activity is high, miscibility is strong, toxicity is low, environmentally friendly, succession crop is waited safely characteristics.The operational path of report is mainly with 3-(2-chloro-a at present, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid is raw material and nitric acid reaction, synthetic 5-(2-chloro-2,2,2-, three fluoro-are to tolyloxy)-2-nitrobenzoic acid, then synthetic fomesafen, wherein nitrated yield, generally in the 75-78% left and right, needs further to improve.
Summary of the invention
The object of the invention is to invent a kind of process for synthesizing fomesafen through directional nitration that improves nitrated yield.
The technical solution used in the present invention is for this reason: the present invention is with 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid is raw material, react under the condition of mixed solvent and aluminium Si catalyst with nitration mixture, temperature is controlled at-5 ℃-0 ℃, and a reaction times 5-6 hour aftertreatment obtains 5-(2-chloro-2,2,2-three fluoro-are to tolyloxy)-the 2-nitrobenzoic acid, and then synthetic fomesafen.
In described aluminium Si catalyst, aluminium, silicon weight ratio are 1:4.
Described nitration mixture is nitric acid and sulfuric acid, 3-(2-chloro-a, a, a-trifluoro p-methoxyphenyl)-weight ratio of phenylformic acid and nitration mixture is 1:0.9.
The weight ratio of described nitric acid and sulfuric acid is 1:2.5-3.
Mixed solvent used is toluene or vinyl acetic monomer or both mixtures.
The weight ratio of described toluene and vinyl acetic monomer is 1:2.
The present invention is with 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid is raw material, adopt the synthetic 5-(2-chloro-2 of directional nitrification technology, 2,2-three fluoro-are to tolyloxy)-2-nitrobenzoic acid and fomesafen, the synthetic total recovery of nitrated yield and fomesafen is all increased, nitrated yield can bring up to 85% from 75%.
Embodiment:
Example 1:
One is equipped with in the 1000ml four-hole boiling flask of stirring, thermometer and device for absorbing tail gas and adds 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid 150 grams, aluminium Si catalyst 0.5 gram and mixed solvent (toluene and vinyl acetic monomer) 200 grams, wherein in the aluminium Si catalyst, aluminium silicon weight ratio is 1:4, and the weight ratio of toluene and vinyl acetic monomer is 1:2; Cooling keeps temperature-5 ℃, drips nitration mixture 135 grams, and the weight ratio of nitric acid and sulfuric acid is 1:3.Reacted 5 hours, and obtained 5-(2-chloro-2,2 after aftertreatment, 2-three fluoro-are to tolyloxy)-the 2-nitrobenzoic acid, then synthesize fomesafen, nitrated yield 85%.
Example 2:
One is equipped with in the 1000ml four-hole boiling flask of stirring, thermometer and device for absorbing tail gas and adds 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid 150 grams, mixed solvent (toluene and vinyl acetic monomer) 200 grams, cooling keeps ℃-0 ℃, temperature-5, drip nitration mixture 135 grams, reacted 5 hours, obtain 5-(2-chloro-2 after aftertreatment, 2,2-three fluoro-are to tolyloxy)-the 2-nitrobenzoic acid, then synthesize fomesafen, nitrated yield 55%-60%.
Example 3:
One is equipped with in the 1000ml four-hole boiling flask of stirring, thermometer and device for absorbing tail gas and adds 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid 150 grams, aluminium Si catalyst 0.5 gram and mixed solvent (toluene and vinyl acetic monomer) 200 grams, wherein in the aluminium Si catalyst, aluminium silicon weight ratio is 1:3.5, and the weight ratio of toluene and vinyl acetic monomer is 1:2.5; Cooling keeps 0 ℃ of temperature, drips nitration mixture 135 grams, and the weight ratio of nitric acid and sulfuric acid is 1:, 2.5, reacted 5 hours, obtain 5-(2-chloro-2,2 after aftertreatment, 2-three fluoro-are to tolyloxy)-the 2-nitrobenzoic acid, then synthesize fomesafen, nitrated yield 82%.
Example 4:
One is equipped with in the 1000ml four-hole boiling flask of stirring, thermometer and device for absorbing tail gas and adds 3-(2-chloro-a, a, the a-trifluoro p-methoxyphenyl)-phenylformic acid 150 grams, aluminium Si catalyst 0.5 gram and toluene 200 grams, cooling keeps ℃-0 ℃, temperature-5, drip nitration mixture 135 grams, reacted 5 hours, obtain 5-(2-chloro-2 after aftertreatment, 2,2-three fluoro-are to tolyloxy)-the 2-nitrobenzoic acid, then synthesize fomesafen, nitrated yield 70%-75%.
Claims (2)
1. process for synthesizing fomesafen through directional nitration, it is characterized in that, with 3-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-phenylformic acid is raw material, with the nitration mixture that is formed by nitric acid and sulfuric acid with toluene, react under the condition of the mixed solvent of vinyl acetic monomer and aluminium Si catalyst, temperature is controlled at-5 ℃-0 ℃, a reaction times 5-6 hour aftertreatment obtains 5-(2-chloro-α, α, α-three fluoro-is to tolyloxy)-the 2-nitrobenzoic acid, and then synthetic fomesafen, wherein: 3-(2-chloro-α, α, the weight ratio of α-trifluoro p-methoxyphenyl)-phenylformic acid and nitration mixture is 1:0.9, aluminium in the aluminium Si catalyst, the silicon weight ratio is 1:4, the weight ratio of toluene and vinyl acetic monomer is 1:2.
2. process for synthesizing fomesafen through directional nitration according to claim 1, is characterized in that, the weight ratio of described nitric acid and sulfuric acid is 1:2.5-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110337238XA CN102329255B (en) | 2011-10-31 | 2011-10-31 | Process for synthesizing fomesafen through directional nitration |
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| CN201110337238XA CN102329255B (en) | 2011-10-31 | 2011-10-31 | Process for synthesizing fomesafen through directional nitration |
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| CN102329255A CN102329255A (en) | 2012-01-25 |
| CN102329255B true CN102329255B (en) | 2013-11-13 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279790A (en) * | 2019-07-23 | 2021-01-29 | 佳木斯市恺乐农药有限公司 | Preparation method of fomesafen original drug |
| CN114887563B (en) * | 2022-06-08 | 2023-07-14 | 江苏长青农化南通有限公司 | Microchannel reactor for improving nitration yield and process thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046798A (en) * | 1973-02-12 | 1977-09-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers |
| GB9510166D0 (en) * | 1995-05-19 | 1995-07-12 | Zeneca Ltd | Catalytic nitration |
| US6028219A (en) * | 1995-09-13 | 2000-02-22 | Zeneca Limited | Process for the nitration of diphenylethers |
| US5946638A (en) * | 1997-08-22 | 1999-08-31 | Jayasuriya; Keerthi | Regioselective nitration of aromatic compounds and the reaction products thereof |
| GB9930369D0 (en) * | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Chemical process |
| CN100334063C (en) * | 2002-06-04 | 2007-08-29 | 高俊 | Aromatic compound nitration manufacturing process |
| CN100522922C (en) * | 2006-03-06 | 2009-08-05 | 北京夏一催化技术有限公司 | Method of preparing nitrobenzene from benzene by nitric acid nitrating |
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