CN112430213A - Synthesis process of trifluoromethylthio pyrazole - Google Patents
Synthesis process of trifluoromethylthio pyrazole Download PDFInfo
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- CN112430213A CN112430213A CN202011405564.5A CN202011405564A CN112430213A CN 112430213 A CN112430213 A CN 112430213A CN 202011405564 A CN202011405564 A CN 202011405564A CN 112430213 A CN112430213 A CN 112430213A
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- Prior art keywords
- trifluoromethylthio
- synthesizing
- trifluoromethylthio pyrazole
- mixed solution
- pyrazole
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- MDLAHYBEAWGVRV-UHFFFAOYSA-N 5-(trifluoromethylsulfanyl)-1h-pyrazole Chemical compound FC(F)(F)SC=1C=CNN=1 MDLAHYBEAWGVRV-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 title abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title abstract description 10
- 239000011259 mixed solution Substances 0.000 claims abstract description 23
- 238000001035 drying Methods 0.000 claims abstract description 19
- 239000012074 organic phase Substances 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000000706 filtrate Substances 0.000 claims abstract description 16
- 239000012071 phase Substances 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 16
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000005191 phase separation Methods 0.000 claims abstract description 15
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
- 230000002194 synthesizing effect Effects 0.000 claims description 15
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003350 kerosene Substances 0.000 claims description 7
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- 238000001291 vacuum drying Methods 0.000 claims description 7
- 235000006408 oxalic acid Nutrition 0.000 claims description 6
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a synthesis process of trifluoromethylthio pyrazole, which comprises the following steps of raw materials of vicinal dipyrazole and trifluoromethyl bromide: A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide; B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use; C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product; D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate; E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
Description
Technical Field
The invention relates to the technical field of trifluoromethylthio pyrazole synthesis, and particularly relates to a process for synthesizing trifluoromethylthio pyrazole.
Background
The prior art has low yield of the trifluoromethylthio pyrazole synthesized by the prior art, and has more waste water and poor environmental protection performance in the synthesis process, so the improvement is necessary.
Disclosure of Invention
The invention aims to provide a process for synthesizing trifluoromethylthio pyrazole, which aims to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: a process for synthesizing trifluoromethylthio pyrazole (CTPMO) from raw materials including vicinal dipyrazole and trifluoromethyl bromide comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
Preferably, the reaction temperature in the step A is 45-55 ℃, and the reaction time is 15-25 min.
Preferably, in the step B, dilute hydrochloric acid and methyl isobutyl ketone are added into the mixed solution to perform phase separation treatment.
Preferably, the catalyst in the step B adopts tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride or dodecyltrimethylammonium chloride.
Preferably, the extractant in the step C is prepared from 30% of trioctylamine, 40% of n-octanol and 30% of sulfonated kerosene.
Preferably, the acid solution in the step D is oxalic acid or dilute hydrochloric acid.
Preferably, the drying in the step E adopts a vacuum drying mode, and the drying temperature is 80-90 ℃.
Compared with the prior art, the invention has the beneficial effects that: the synthesis process adopted by the invention is simple to operate, and the obtained trifluoromethylthio pyrazole has high purity; wherein, the catalyst and the extracting agent added into the organic phase can improve the single extraction efficiency and further improve the synthesis efficiency.
Drawings
FIG. 1 is a diagram of the synthesis process of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
referring to fig. 1, the present invention provides the following technical solutions: a process for synthesizing trifluoromethylthio pyrazole (CTPMO) from raw materials including vicinal dipyrazole and trifluoromethyl bromide comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
In this example, the reaction temperature in step A was 45 ℃ and the reaction time was 15 min.
In this embodiment, in step B, dilute hydrochloric acid and methyl isobutyl ketone are added to the mixed solution to perform phase separation treatment.
In this example, tetrabutylammonium hydrogen sulfate was used as the catalyst in step B.
In this example, the extractant in step C was made from 30% trioctylamine, 40% n-octanol, and 30% sulfonated kerosene.
In this embodiment, the acid solution in step D is oxalic acid.
In this example, the drying in step E was performed in a vacuum drying mode at a temperature of 80 ℃.
Example two:
a process for synthesizing trifluoromethylthio pyrazole comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
In this example, the reaction temperature in step A was 55 ℃ and the reaction time was 25 min.
In this embodiment, in step B, dilute hydrochloric acid and methyl isobutyl ketone are added to the mixed solution to perform phase separation treatment.
In this example, the catalyst used in step B was trioctylmethylammonium chloride.
In this example, the extractant in step C was made from 30% trioctylamine, 40% n-octanol, and 30% sulfonated kerosene.
In this embodiment, the acid solution in step D is diluted hydrochloric acid.
In this example, the drying in step E was performed in a vacuum drying mode at a drying temperature of 90 ℃.
Example three:
a process for synthesizing trifluoromethylthio pyrazole comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
In this example, the reaction temperature in step A was 48 ℃ and the reaction time was 18 min.
In this embodiment, in step B, dilute hydrochloric acid and methyl isobutyl ketone are added to the mixed solution to perform phase separation treatment.
In this example, dodecyl trimethyl ammonium chloride was used as the catalyst in step B.
In this example, the extractant in step C was made from 30% trioctylamine, 40% n-octanol, and 30% sulfonated kerosene.
In this embodiment, the acid solution in step D is oxalic acid.
In this example, the drying in step E was performed in a vacuum drying mode at a temperature of 82 ℃.
Example four:
a process for synthesizing trifluoromethylthio pyrazole comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
In this example, the reaction temperature in step A was 52 ℃ and the reaction time was 22 min.
In this embodiment, in step B, dilute hydrochloric acid and methyl isobutyl ketone are added to the mixed solution to perform phase separation treatment.
In this example, dodecyl trimethyl ammonium chloride was used as the catalyst in step B.
In this example, the extractant in step C was made from 30% trioctylamine, 40% n-octanol, and 30% sulfonated kerosene.
In this embodiment, the acid solution in step D is oxalic acid.
In this example, the drying in step E was performed in a vacuum drying mode at 88 ℃.
Example five:
a process for synthesizing trifluoromethylthio pyrazole comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
In this example, the reaction temperature in step A was 50 ℃ and the reaction time was 20 min.
In this embodiment, in step B, dilute hydrochloric acid and methyl isobutyl ketone are added to the mixed solution to perform phase separation treatment.
In this example, tetrabutylammonium hydrogen sulfate was used as the catalyst in step B.
In this example, the extractant in step C was made from 30% trioctylamine, 40% n-octanol, and 30% sulfonated kerosene.
In this embodiment, the acid solution in step D is oxalic acid.
In this example, the drying in step E was performed in a vacuum drying mode at a drying temperature of 85 ℃.
Experimental example:
the trifluoromethylthio pyrazole synthesized by the examples of the present invention was used for purity testing, and the data obtained are as follows:
| purity (%) | |
| Example one | 98.2 |
| Example two | 98.2 |
| EXAMPLE III | 98.6 |
| Example four | 98.4 |
| EXAMPLE five | 98.7 |
In conclusion, the synthesis process adopted by the invention is simple to operate, and the obtained trifluoromethylthio pyrazole has high purity; wherein, the catalyst and the extracting agent added into the organic phase can improve the single extraction efficiency and further improve the synthesis efficiency.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (7)
1. A process for synthesizing trifluoromethylthio pyrazole, which comprises raw materials of vicinal dipyrazole and trifluoromethyl bromide, and is characterized in that: the method comprises the following steps:
A. firstly, reacting the vicinal dipyrazole with trifluoromethyl bromide to generate a mixed solution of trifluoromethylthio pyrazole and sodium bromide;
B. b, carrying out phase separation treatment on the mixed solution obtained in the step A to obtain a water phase and an organic phase, and recovering the water phase for later use;
C. adding a catalyst and an extracting agent into the organic phase obtained in the step B for extraction reaction to obtain a product;
D. adding acid liquor into the product for neutralization, and filtering to obtain filtrate;
E. and finally, carrying out filter pressing and drying on the filtrate to obtain the trifluoromethylthio pyrazole.
2. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: in the step A, the reaction temperature is 45-55 ℃ and the reaction time is 15-25 min.
3. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: and in the step B, dilute hydrochloric acid and methyl isobutyl ketone are added into the mixed solution for phase separation treatment.
4. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: and the catalyst in the step B adopts tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride or dodecyl trimethyl ammonium chloride.
5. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: and the extracting agent in the step C is prepared from 30 percent of trioctylamine, 40 percent of n-octanol and 30 percent of sulfonated kerosene.
6. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: and D, adopting oxalic acid or dilute hydrochloric acid as the acid solution in the step D.
7. The process for synthesizing trifluoromethylthio pyrazole according to claim 1, wherein: and D, drying in the step E in a vacuum drying mode, wherein the drying temperature is 80-90 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202011405564.5A CN112430213A (en) | 2020-12-03 | 2020-12-03 | Synthesis process of trifluoromethylthio pyrazole |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011405564.5A CN112430213A (en) | 2020-12-03 | 2020-12-03 | Synthesis process of trifluoromethylthio pyrazole |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005023774A1 (en) * | 2003-09-11 | 2005-03-17 | Cheminova A/S | Process for the preparation of a trifluoromethylthioether |
| CN101445483A (en) * | 1999-10-22 | 2009-06-03 | 拜尔农科股份有限公司 | Process for preparing pesticides |
| CN101544607A (en) * | 2009-04-30 | 2009-09-30 | 宁波中化化学品有限公司 | Method for synthesizing 1-aryl pyrazole compound containing trifluoromethylsulfinyl |
-
2020
- 2020-12-03 CN CN202011405564.5A patent/CN112430213A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101445483A (en) * | 1999-10-22 | 2009-06-03 | 拜尔农科股份有限公司 | Process for preparing pesticides |
| WO2005023774A1 (en) * | 2003-09-11 | 2005-03-17 | Cheminova A/S | Process for the preparation of a trifluoromethylthioether |
| CN101544607A (en) * | 2009-04-30 | 2009-09-30 | 宁波中化化学品有限公司 | Method for synthesizing 1-aryl pyrazole compound containing trifluoromethylsulfinyl |
Non-Patent Citations (2)
| Title |
|---|
| RI-YUAN TANG等: "A convenient conversion of pyrazolyl disulfide to sulfides by sodium dithionite and synthesis of sulfoxides", 《JOURNAL OF FLUORINE CHEMISTRY》 * |
| 蒋富国等: "氟虫腈的催化氧化合成研究", 《上海化工》 * |
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Application publication date: 20210302 |