CN109280008A - 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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- CN109280008A CN109280008A CN201710593534.3A CN201710593534A CN109280008A CN 109280008 A CN109280008 A CN 109280008A CN 201710593534 A CN201710593534 A CN 201710593534A CN 109280008 A CN109280008 A CN 109280008A
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- oxyfluorfen
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- fluorine
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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
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 of 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.
Most of synthesis of existing Oxyfluorfen is all double etherification technologies, wherein having the 3 of 1 molecule, bis- chlorobenzotrifluoride of 4-
Conversion is for the chloro- 4- trifloro methyl phenol of 2- (fluorine phenol).As by-product, most of factory is all used as dangerous waste to handle.Some reports
Acifluorfen can be synthesized, but difficulty is larger, it is more difficult to promote.
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 with energy saving, easy to operate, protection environmental quality the present invention provides a kind of
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 nitre
Base benzene or 2,4- dichloronitrobenzene are starting material, start first ethoxylation, then two generation ethoxy fluorine grass are reacted with fluorine phenol
Ether.
Preferably, in a kind of above-mentioned method using Oxyfluorfen by-product production Oxyfluorfen,
The fluoro- 1- nitrobenzene of 2- ethyoxyl -4- can be prepared by 2,4- difluoro nitrobenzene or directly purchase 2- ethyoxyl -4-
Fluoro- 1- nitrobenzene is starting 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.
Ethoxy fluorine is utilized with energy saving, easy to operate, protection environmental quality the embodiment of the invention discloses a kind of
The method of careless ether 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 with fluorine phenol
React two generation Oxyfluorfens；Reactional equation is as follows:
The present invention utilizes the chloro- 4- trifloro methyl phenol of Oxyfluorfen by-product 2- (fluorine phenol) synthesizing oxyfluorfen
New technology 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 20% sodium ethoxide is added dropwise
45 grams, 5 DEG C≤reaction temperature≤20 DEG C of process control are added dropwise.End of reaction detects 2,4- difluoro nitrobenzene conversion ratio >=99%
It is considered as reaction to complete.40% sulfuric acid is added dropwise and adjusts pH value to neutrality.Precipitation prolapse solvent, precipitation finish, and 80 grams of toluene, water is added
It washes.Twice of washing after dividing to fall lower water, after deviating from toluene, is added petroleum ether recrystallization, obtains 2- ethyoxyl-after vacuum drying
22.5 grams of the fluoro- 1- nitrobenzene crude product of 4-, 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 potassium hydroxide 6.5
Gram, then after putting into 19 grams of the fluoro- 1- nitrobenzene crude product of 2- ethyoxyl -4-, 90 DEG C are warming up to, after keeping the temperature 5h.Detect 2- ethyoxyl -4-
Fluoro- 1- 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.
Twice of washing after dividing to fall lower water, after deviating from toluene, is added dehydrated alcohol recrystallization, obtains Oxyfluorfen after vacuum drying
32.8 grams, 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 potassium carbonate 14.5
Gram, then after putting into 19 grams of the fluoro- 1- nitrobenzene crude product of 2- ethyoxyl -4-, 90 DEG C are warming up to, after keeping the temperature 5h.Detect 2- ethyoxyl -4-
Fluoro- 1- 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.
Twice of washing after dividing to fall lower water, after deviating from toluene, is added dehydrated alcohol recrystallization, obtains Oxyfluorfen after vacuum drying
30.5 grams, 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 throw
After entering 19 grams of the fluoro- 1- nitrobenzene crude product of 2- ethyoxyl -4-, 90 DEG C are warming up to, after keeping the temperature 5h.Detect the fluoro- 1- nitre of 2- ethyoxyl -4-
Base benzene conversion ratio >=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 33.2 grams of Oxyfluorfen after vacuum drying,
Internal standard content 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, start first ethoxylation, then two generation Oxyfluorfens are reacted with fluorine phenol.
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 |
|---|---|---|---|
| CN201710593534.3A CN109280008A (en) | 2017-07-19 | 2017-07-19 | A method of utilizing Oxyfluorfen by-product production Oxyfluorfen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710593534.3A CN109280008A (en) | 2017-07-19 | 2017-07-19 | A method of utilizing Oxyfluorfen by-product production Oxyfluorfen |
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| Publication Number | Publication Date |
|---|---|
| CN109280008A true CN109280008A (en) | 2019-01-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710593534.3A Pending CN109280008A (en) | 2017-07-19 | 2017-07-19 | 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
- 2017-07-19 CN CN201710593534.3A patent/CN109280008A/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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