CN109970567A - A method of utilizing Oxyfluorfen by-product production Oxyfluorfen - Google Patents
A method of utilizing Oxyfluorfen by-product production Oxyfluorfen Download PDFInfo
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- CN109970567A CN109970567A CN201711452481.XA CN201711452481A CN109970567A CN 109970567 A CN109970567 A CN 109970567A CN 201711452481 A CN201711452481 A CN 201711452481A CN 109970567 A CN109970567 A CN 109970567A
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- Prior art keywords
- oxyfluorfen
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- fluorine
- phenol
- nitrobenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Abstract
The invention discloses a kind of methods using Oxyfluorfen by-product production Oxyfluorfen, it is characterized in that, using 2,4- difluoro nitrobenzene or 2,4- dichloronitrobenzene as starting material, start first ethoxylation, then two generation Oxyfluorfens are reacted with fluorine phenol.The present invention is the new technology route using the chloro- 4- trifloro methyl phenol of Oxyfluorfen by-product 2- (fluorine phenol) synthesizing oxyfluorfen, has not only solved the Utilizing question of fluorine phenol, but also solve the registration problem for being made into other products；Compared with prior art, it has the characteristics that energy saving, easy to operate, protection environment.
Description
Technical field
The present invention relates to Oxyfluorfen technical fields, more particularly to a kind of to utilize Oxyfluorfen by-product
The method for producing Oxyfluorfen.
Background technique
Oxyfluorfen is the fluorine-containing benzene ether-derivative herbicides succeeded in developing by Rhom and Hass, the U.S. in 1975, weeding
Activity improves 5 ~ 10 times than corresponding nitrofen, is 16.32 times of benthiocarb.Use scope is wide, and broad weed-killing spectrum, the lasting period is long,
Mu dosage is few, and activity is high, can use with a variety of mixture of herbicides, expands degrass spectrum, and raising drug effect is easy to use, both can be before bud
Processing, but can bud post-processing, toxicity is low.
Oxyfluorfen is the fluorine-containing benzene ether-derivative herbicides succeeded in developing by Rhom and Hass, the U.S. in 1975, weeding
Activity improves 5 ~ 10 times than corresponding nitrofen, is 16.32 times of benthiocarb.Use scope is wide, and broad weed-killing spectrum, the lasting period is long,
Mu dosage is few, and activity is high, can use with a variety of mixture of herbicides, expands degrass spectrum, and raising drug effect is easy to use, both can be before bud
Processing, but can bud post-processing, toxicity is low.
Therefore, how a kind of utilization Oxyfluorfen pair that is not only energy saving, easy to operate but also protecting environment is provided
The problem of method that product produces Oxyfluorfen is those skilled in the art's urgent need to resolve.
Summary of the invention
In view of this, utilizing ethoxy the present invention provides a kind of not only energy saving, easy to operate but also protection environment
The method of fluofazone by-product production Oxyfluorfen.
To achieve the above object, the invention provides the following technical scheme:
A method of utilizing Oxyfluorfen by-product production Oxyfluorfen, which is characterized in that with 2,4- difluoro nitrobenzene
Or 2,4- dichloronitrobenzene is starting material, starts first ethoxylation, then two generation Oxyfluorfens are reacted with fluorine phenol.
Preferably, in a kind of above-mentioned method using Oxyfluorfen by-product production Oxyfluorfen, can pass through
2, the fluoro- 1- nitrobenzene of 4- difluoro nitrobenzene preparation 2- ethyoxyl -4- or the directly buying fluoro- 1- nitrobenzene of 2- ethyoxyl -4- are
Beginning raw material and fluorine phenol one-step synthesis Oxyfluorfen.
It can be seen via above technical scheme that compared with prior art, utilizing ethoxy fluorine the present disclosure provides a kind of
The method of careless ether by-product production Oxyfluorfen, which is characterized in that with 2,4- difluoro nitrobenzene or 2,4- dichloronitrobenzene
For starting material, start first ethoxylation, then reacts two generation Oxyfluorfens with fluorine phenol.The present invention is to utilize ethoxy fluorine grass
The new technology route of the chloro- 4- trifloro methyl phenol of ether by-product 2- (fluorine phenol) synthesizing oxyfluorfen；Compared with prior art, it
Has the characteristics that energy saving, easy to operate, protection environment.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical scheme in the embodiment of the invention is clearly and completely described,
Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based in the present invention
Embodiment, every other embodiment obtained by those of ordinary skill in the art without making creative efforts, all
Belong to the scope of protection of the invention.
The embodiment of the invention discloses a kind of utilization second with energy saving, easy to operate protection environmental quality
The method of oxygen fluofazone by-product production Oxyfluorfen.
A kind of method using Oxyfluorfen by-product production Oxyfluorfen disclosed by the invention is please referred to, it is specific to wrap
It includes:
Using 2,4- difluoro nitrobenzene or 2,4- dichloronitrobenzene as starting material, start first ethoxylation, then react with fluorine phenol
Two generation Oxyfluorfens；Reactional equation is as follows:
The present invention is the new work using the chloro- 4- trifloro methyl phenol of Oxyfluorfen by-product 2- (fluorine phenol) synthesizing oxyfluorfen
Skill route；Compared with prior art, it has the characteristics that energy saving, easy to operate, protection environment.
In order to further optimize the above technical scheme, specific embodiment 1 are as follows:
2,20 grams of 4- difluoro nitrobenzene are put into the there-necked flask of 250ml, then put into 60 grams of toluene, and 45 grams of 20% sodium ethoxide is added dropwise,
5 DEG C≤reaction temperature≤20 DEG C of process control are added dropwise.End of reaction, detection 2,4- difluoro nitrobenzene conversion ratio >=99% are considered as instead
It should complete.40% sulfuric acid is added dropwise and adjusts pH value to neutrality.Precipitation prolapse solvent, precipitation finish, and 80 grams of toluene are added, washing.Washing
Twice, after dividing to fall lower water, after deviating from toluene, petroleum ether recrystallization is added, obtains the fluoro- 1- of 2- ethyoxyl -4- after vacuum drying
22.5 grams of nitrobenzene crude product, chromatographic content 95%, yield 91.85%.
In order to further optimize the above technical scheme, specific embodiment 2 are as follows:
20 grams of fluorine phenol are put into the there-necked flask of 250ml, then put into 70 grams of dimethyl sulfoxide, then put into 6.5 grams of potassium hydroxide, then
After fluoro- 19 grams of 1- nitrobenzene crude product of 2- ethyoxyl -4- of investment, 90 DEG C are warming up to, after keeping the temperature 5h.Detect the fluoro- 1- of 2- ethyoxyl -4-
Nitrobenzene conversion rate >=99%, which is considered as reaction, to be completed.Precipitation prolapse solvent, precipitation finish, and 80 grams of toluene are added, washing.Washing two
Time, after dividing to fall lower water, after deviating from toluene, dehydrated alcohol recrystallization is added, obtains 32.8 grams of Oxyfluorfen after vacuum drying,
Internal standard content 95.5%, yield 89.24%.
In order to further optimize the above technical scheme, specific embodiment 3 are as follows:
20 grams of fluorine phenol are put into the there-necked flask of 250ml, then put into 70 grams of dimethyl sulfoxide, then put into 14.5 grams of potassium carbonate, then
After fluoro- 19 grams of 1- nitrobenzene crude product of 2- ethyoxyl -4- of investment, 90 DEG C are warming up to, after keeping the temperature 5h.Detect the fluoro- 1- of 2- ethyoxyl -4-
Nitrobenzene conversion rate >=99%, which is considered as reaction, to be completed.Precipitation prolapse solvent, precipitation finish, and 80 grams of toluene are added, washing.Washing two
Time, after dividing to fall lower water, after deviating from toluene, dehydrated alcohol recrystallization is added, obtains 30.5 grams of Oxyfluorfen after vacuum drying,
Internal standard content 93.6%, yield 81.33%.
In order to further optimize the above technical scheme, specific embodiment 4 are as follows:
20 grams of fluorine phenol are put into the there-necked flask of 250ml, then put into DMF70 grams, then put into 6.5 grams of potassium hydroxide, then put into 2-
After 19 grams of the fluoro- 1- nitrobenzene crude product of ethyoxyl -4-, 90 DEG C are warming up to, after keeping the temperature 5h.Detect the fluoro- 1- nitrobenzene of 2- ethyoxyl -4-
Conversion ratio >=99%, which is considered as reaction, to be completed.Precipitation prolapse solvent, precipitation finish, and 80 grams of toluene are added, washing.Twice of washing divides to fall
After lower water, after deviating from toluene, dehydrated alcohol recrystallization is added, obtains 33.2 grams of Oxyfluorfen after vacuum drying, internal standard contains
Amount 95.7%, yield 90.52%.
Each embodiment in this specification is described in a progressive manner, the highlights of each of the examples are with other
The difference of embodiment, the same or similar parts in each embodiment may refer to each other.For device disclosed in embodiment
For, since it is corresponded to the methods disclosed in the examples, so being described relatively simple, related place is said referring to method part
It is bright.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest scope of cause.
Claims (2)
1. a kind of method using Oxyfluorfen by-product production Oxyfluorfen, which is characterized in that with 2,4- difluoro nitro
Benzene or 2,4- dichloronitrobenzene are starting material, by first ethoxylation, then react two steps with fluorine phenol and generate ethoxy fluorine
Careless ether.
2. a kind of method using Oxyfluorfen by-product production Oxyfluorfen according to claim 1, feature
It is, the fluoro- 1- nitrobenzene of 2- ethyoxyl -4- can be prepared by 2,4- difluoro nitrobenzene or directly buying 2- ethyoxyl -4- is fluoro-
1- nitrobenzene is starting material and fluorine phenol one-step synthesis Oxyfluorfen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711452481.XA CN109970567A (en) | 2017-12-28 | 2017-12-28 | A method of utilizing Oxyfluorfen by-product production Oxyfluorfen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711452481.XA CN109970567A (en) | 2017-12-28 | 2017-12-28 | A method of utilizing Oxyfluorfen by-product production Oxyfluorfen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109970567A true CN109970567A (en) | 2019-07-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711452481.XA Pending CN109970567A (en) | 2017-12-28 | 2017-12-28 | A method of utilizing Oxyfluorfen by-product production Oxyfluorfen |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019388A1 (en) * | 1979-05-02 | 1980-11-26 | Rohm And Haas Company | Preparation of trifluoromethyl-substituted phenols and phenates and the preparation, from these phenols and phenates, of nitro- and trifluoromethyl-substituted diphenyl ethers |
-
2017
- 2017-12-28 CN CN201711452481.XA patent/CN109970567A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019388A1 (en) * | 1979-05-02 | 1980-11-26 | Rohm And Haas Company | Preparation of trifluoromethyl-substituted phenols and phenates and the preparation, from these phenols and phenates, of nitro- and trifluoromethyl-substituted diphenyl ethers |
Non-Patent Citations (1)
| Title |
|---|
| MICHAEL D. WENDT等: "Ortho-selectivity in SNAr substitutions of 2,4-dihaloaromatic compounds. Reactions with anionic nucleophiles", 《TETRAHEDRON LETTERS》 * |
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Effective date of registration: 20201223 Address after: 256600 south side of xinyongxin Road, Binbei office, Bincheng District, Binzhou City, Shandong Province Applicant after: Shoujian Technology Co.,Ltd. Address before: 256600 south side of xinyongxin Road, Binbei office, Bincheng District, Binzhou City, Shandong Province Applicant before: SHANDONG QIAOCHANG CHEMICAL Co.,Ltd. |
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Application publication date: 20190705 |
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