CN107501256B - Preparation method of high-purity thiamethoxam - Google Patents
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Abstract
The invention discloses a preparation method of high-purity thiamethoxam, which is of a structure shown in a formula (I), and the method comprises the following steps of mixing a compound with the structure shown in a formula (II) and a compound with the structure shown in a formula (III)A structural compound is shown, and reacts in a polar aprotic solvent in the presence of a catalyst and inorganic base, and a thiamethoxam product with the purity higher than 99% is obtained through filtration, decoloration, desolventization and crystallization, wherein the yield is 90%. The method has the advantages of short reaction time, low reaction temperature, easy operation and environmental protection, improves the purity and yield of the product, and is suitable for industrial production.
Description
Technical Field
The invention relates to a preparation method of high-purity thiamethoxam.
Background
Thiamethoxam, chemical name: 3- (2-chloro-5-thiazolylmethyl) -5-methyl-N-nitro-4H-1, 3, 5-tetrahydrooxadiazin-4-imine represented by the following structural formula (I):
thiamethoxam is a neonicotinoid insecticide developed by Nowa company in 1991, and can selectively inhibit nicotinic acetylcholine esterase receptors of central nervous systems of insects, so that normal conduction of the central nervous systems of the insects is blocked, and the insects are paralyzed and even die.
Thiamethoxam has high activity on coleoptera, diptera and lepidoptera pests, particularly homoptera pests, and can effectively control various pests such as aphids, leafhoppers, plant hoppers, potato beetles, nematodes, leaf miners and the like, and pests with resistance to other chemical pesticides. The thiamethoxam has the advantages of contact poisoning, stomach toxicity and systemic activity, higher activity, better safety, wider insecticidal spectrum, high action speed and long lasting period, and is a better variety for replacing organophosphorus, carbamate and organochlorine insecticides which have high toxicity, residue and environmental problems on mammals.
The thiamethoxam can be used for stem leaf treatment, seed treatment and soil treatment. Suitable crops are rice crops, beet, soybean, rape, potato, fruit trees, peanut, tobacco, orange and the like. The pesticide is safe and harmless to crops when used under the recommended dosage.
The classical method for synthesizing thiamethoxam at home and abroad comprises the following steps: the thiamethoxam is prepared from a compound 2-chloro-5-chloromethylthiazole and 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine.
The reaction formula is as follows:
the above methods are reported in patents PCT2002034734, 2006Mu00715, WO 0100623. The patent CN102372702, CN106188032A and C106496215A improve the preparation method, and although the yield is improved, a large amount of dichloroethane is required for extraction, so the productivity is lower; dichloroethane is a toxic and harmful solvent and is limited in industrial use.
In other domestic patent preparation methods, DMF is mostly used as a solvent, potassium carbonate is used as an acid-binding agent, and the mixture is stirred for 8 to 15 hours at the temperature of between 20 and 70 ℃. After the reaction is finished, adding water with 5-10 times volume to separate out the product, filtering and separating out a crude product, and recrystallizing by using methanol or crystallizing after dissolving and extracting by using dichloromethane and dichloroethane to obtain the thiamethoxam product with the content of 96-98%. A large amount of DMF and salt enter the wastewater, so that COD, ammonia nitrogen and salt in the wastewater are high, the environmental protection pressure is huge, and the wastewater is difficult to treat; and solvent recovery is difficult due to the introduction of mixed solvents. Thiamethoxam products are unstable under alkaline conditions, decompose faster at higher temperatures, and generate a large amount of tar. The higher the purity, the more stable the thiamethoxam product is. However, the synthesis reaction is carried out under alkaline conditions, which are unavoidable, and the higher the synthesis temperature, the faster the decomposition rate of the product. At present, no report is found on a preparation method for preparing high-purity (more than or equal to 99%) thiamethoxam with high yield, the product yield of the existing preparation method is low, and the obtained thiamethoxam product and the commercially available thiamethoxam have the highest content of only 98%.
Based on the above disadvantages of the prior art methods, it would be highly desirable to develop an improved method for the preparation of high purity (≧ 99%) thiamethoxam, which is suitable for industrial applications, simple, low cost, high yield and environmentally friendly, thereby overcoming the drawbacks of the prior art.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the defects of the prior art, the invention provides the thiamethoxam preparation method which is simple, effective, easy to operate, environment-friendly, capable of improving the product yield and purity, and suitable for industrial production, and has high purity (not less than 99%) and high yield.
The technical scheme is as follows: the invention relates to a preparation method of high-purity thiamethoxam, which comprises the following steps:
reacting 2-chloro-5-chloromethyl thiazole with a structural compound shown as a formula (II) and 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine with an acid-binding agent of an inorganic base in a polar aprotic solvent under the action of a catalyst at the reaction temperature of 20-35 ℃; the reaction time is 5-6 hours; after the reaction is finished, filtering to remove inorganic salt, adding a decoloring agent into the filtrate, and stirring at room temperature for decoloring; filtering again, concentrating the filtrate under reduced pressure, recovering the solvent, adding water into the remainder, heating to full solution, cooling, crystallizing, filtering, and drying to obtain a white thiamethoxam product with a purity of more than 99% and a structure shown in formula (I);
the catalyst is 4-dimethylaminopyridine and Me-DABCO;
furthermore, the molar ratio of the 2-chloro-5-chloromethylthiazole to the 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine to the inorganic base to the catalyst is 1:1.2 (0.5-2) to (0.001-1).
Furthermore, the molar ratio of the 2-chloro-5-chloromethylthiazole to the 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine to the inorganic base to the catalyst is 1:1.2 (1-1.5) to (0.005-0.2).
Furthermore, the weight ratio of the 2-chloro-5-chloromethylthiazole to the decolorizing agent to the polar aprotic solvent is 1: 0.01-0.5 (1-10).
Furthermore, the weight ratio of the 2-chloro-5-chloromethylthiazole to the decolorizing agent to the polar aprotic solvent is 1: 0.1-0.5 (5-10).
Further, the inorganic base is potassium carbonate.
Further, the polar aprotic solvent is an amide solvent or a ketone solvent.
Still further, the polar aprotic solvent is one or more of DMAA, MIBK, NMP.
Further, the decolorizing agent is any one of activated carbon, diatomite and adsorption resin.
The inventors of the present invention have found through intensive studies that the hydrolysis rates of thiamethoxam products with different contents under different PH conditions are as follows:
| properties of | Results |
| Hydrolysis rate (purity 99.0%) [14C-oxadiazin label] | pH9,25 deg.C, 30 days detection, T0.5 ═ 8.8 days |
| Hydrolysis rate (purity 99.3%) [14C-oxadiazin label] | pH9,60 deg.C, 5 days test, T0.5 ═ 8.0 days |
| Hydrolysis rate (purity 98.0%) [14C-oxadiazin label] | pH9,60 ℃,96 hours detection, T0.5 ═ 100 hours |
| Hydrolysis rate (purity 97.5%) [14C-oxadiazin label] | pH9,60 ℃,20 days detection, T0.5 ═ 80 hours |
| Hydrolysis rate (purity 95.4%) [14C-oxadiazin label] | Measured at pH9,60 ℃ for 30 days, and T0.5 is 56 hours |
According to experimental data, the higher the purity is, the more stable the thiamethoxam product is. However, the synthesis reaction is carried out under alkaline conditions, which are unavoidable, and the higher the synthesis temperature, the faster the decomposition rate of the product. At present, no report exists on a preparation method for preparing high-purity (more than or equal to 99%) thiamethoxam with high yield.
Has the advantages that: (1) the invention adopts 4-dimethylamino pyridine or Me-DABCO as a catalyst, takes alkali as an acid-binding agent, can react in a proper solvent at room temperature, and can thoroughly convert raw materials into products. Because the reaction and the post-treatment operation are carried out at low temperature, the hydrolysis of products in the prior art is effectively avoided, the side reaction is reduced, and the reaction yield is greatly improved.
(2) The preparation method has the advantages of mild reaction conditions, simple method, low cost, high yield, simple solvent recovery treatment and no corrosion to equipment. Because a large amount of salt and impurities generated by product hydrolysis are effectively prevented from entering the wastewater, a series of influences on the environment caused by post-treatment are reduced, and the method is suitable for industrial production.
(3) Compared with the thiamethoxam product sold in the market, the thiamethoxam product prepared by the method has higher purity and yield.
Drawings
FIG. 1 is a FT-IR spectrum of high purity thiamethoxam;
FIG. 2 shows the preparation of high purity thiamethoxam1H-NMR spectrum;
Detailed Description
The technical solution of the present invention is described in detail by the following specific examples, but the scope of the present invention is not limited to the examples.
In the embodiment of the invention, the purity of the thiamethoxam is measured by adopting a high performance liquid chromatography.
Example 1:
in a flask equipped with a condenser, 840g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylaminopyridine are sequentially added, stirring is started, the temperature is controlled to be about 25 ℃, and 169g (1mol) of 2-chloro-5-chloromethylthiazole are dropwise added. After the dropwise addition, stirring is carried out for 5 hours at room temperature, discharging materials, centrifuging to remove potassium salt, leaching a filter cake with DMAA, adding 20g of activated carbon into obtained filtrate, stirring for 30 minutes at room temperature, filtering to remove the activated carbon, carrying out pressure reduction desolventizing on the obtained filtrate, recovering the solvent, adding 220g of water into residues, heating to 70-80 ℃ for dissolution, cooling to 0 ℃ for suction filtration to obtain a white-like solid, and drying to obtain 267.1g of thiamethoxam finished product with the purity of 99.3% and the yield of 91%. (by HPLC)
IR：1600.85cm-1Nitro peak, 1266.21cm-1Peaks of unsaturated thioether bonds and thiamethoxam infrared characteristic peaks all appear. (see attached FIG. 1)
1HNMR(CDCl3500Hz) delta 7.49(s,1H),4.91(s,2H),4.88(s,2H),4.74(s,2H),2.93(s, 3H). (see attached FIG. 2)
Example 2
In a flask equipped with a condenser, 320g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 139g (1mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylaminopyridine are sequentially added, stirring is started, the temperature is controlled to be about 25 ℃, and 169g (1mol) of 2-chloro-5-chloromethylthiazole are dropwise added. After the dropwise addition, stirring is carried out for 5 hours at room temperature, discharging materials, centrifuging to remove sylvite, leaching a filter cake by DMAA, adding 10g of activated carbon into obtained filtrate, stirring for 30 minutes at room temperature, filtering to remove the activated carbon, carrying out decompression desolventizing on the obtained filtrate, recovering the solvent, adding 220g of water into residues, heating to 70-80 ℃ for dissolving, cooling to 0 ℃ for carrying out suction filtration to obtain a white-like solid, and drying to obtain 263.0g of thiamethoxam finished product with the purity of 99.4% and the yield of 89.6%. (by HPLC)
The analytical data were as in example 1.
Example 3
840g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 167g (1.2mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylamino pyridine are sequentially added into a flask provided with a condenser, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethyl thiazole is dropwise added, stirring is carried out for 5 hours at room temperature after dropwise addition is finished, discharging is carried out, potassium salt is centrifugally removed, filter cakes are rinsed by DMAA, 20g of kieselguhr is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, activated carbon is filtered and removed, the obtained filtrate is decompressed and desolventized, the solvent is recovered, 220g of water is added into residues, the residues are heated to 70-80 ℃ for dissolution, the temperature is reduced to 0 ℃ for suction filtration, a white-like solid is obtained, drying is carried out, 265, the purity was 99.4% and the yield was 90.3%. (by HPLC)
The analytical data were as in example 1.
Example 4
840g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 70g (0.5mol) of potassium carbonate and 23g (0.2mol) of Me-DABCO are sequentially added into a flask provided with a condenser, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethylthiazole is dropwise added, stirring is carried out for 5 hours at room temperature after dropwise addition is finished, discharging is carried out, potassium salt is centrifugally removed, filter cakes are rinsed by DMAA, 20g of activated carbon is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, the activated carbon is filtered and removed, the obtained filtrate is decompressed and desolventized, the solvent is recovered, 220g of water is added into residues, the residues are heated to 70-80 ℃ for dissolution, the temperature is reduced to 0 ℃ for suction filtration, a white-like solid is obtained, drying is carried out, 265.8g of, the yield thereof was found to be 90.4%. (by HPLC)
The analytical data were as in example 1.
Example 5
840g of MIBK, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 280g (2mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylamino pyridine are sequentially added into a flask provided with a condenser, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethyl thiazole are dropwise added, stirring is carried out for 5 hours at room temperature after dropwise addition is finished, potassium salt is removed by discharging centrifugation, a filter cake is rinsed with MIBK, 80g of adsorption resin is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, activated carbon is removed by filtration, obtained filtrate is decompressed and desolventized, solvent is recovered, 220g of water is added into remainder, the temperature is raised to 70-80 ℃ for dissolution, the temperature is lowered to 0 ℃ for suction filtration, white-like solid is obtained, and 267.0g of thiamethoxam finished product is, purity 99.4%, yield 91%. (by HPLC)
The analytical data were as in example 1.
Example 6
840g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 125g (1mol) of 4-dimethylamino pyridine are sequentially added into a flask provided with a condenser, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethyl thiazole is dropwise added, stirring is carried out for 5 hours at room temperature after the dropwise addition is finished, discharging is carried out, potassium salt is centrifugally removed, filter cakes are rinsed by DMAA, 2g of active carbon is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, the active carbon is removed by filtration, obtained filtrate is decompressed and desolventized, solvent is recovered, 220g of water is added into residues, the temperature is raised to 70-80 ℃ for dissolution, the temperature is lowered to 0 ℃ for suction filtration, white-like solids are obtained, drying is carried out, 268.5g, the purity was 99.4% and the yield was 91.5%. (by HPLC)
The analytical data were as in example 1.
Example 7
1600g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 0.2g (0.001mol) of 4-dimethylaminopyridine are sequentially added into a flask provided with a condenser, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethylthiazole is dropwise added, stirring is carried out for 5 hours at room temperature after dropwise addition is finished, discharging is carried out, potassium salt is removed through centrifugation, a filter cake is rinsed by DMAA, 20g of activated carbon is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, the activated carbon is removed through filtration, obtained filtrate is decompressed and desolventized, a solvent is recovered, 220g of water is added into remainder, the temperature is raised to 70-80 ℃ for dissolution, the temperature is reduced to 0 ℃ for suction filtration, a white-like solid is obtained, drying is carried out, the purity is 99.1 percent, and the yield is 90.8 percent. (by HPLC)
The analytical data were as in example 1.
Example 8
In a flask equipped with a condenser, 320g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 1g (0.005mol) of 4-dimethylaminopyridine are sequentially added, stirring is started, the temperature is controlled to be about 25 ℃, 169g (1mol) of 2-chloro-5-chloromethylthiazole is dropwise added, stirring is carried out for 5 hours at room temperature after dropwise addition is finished, discharging is carried out, potassium salt is centrifugally removed, filter cakes are rinsed by DMAA, 10g of activated carbon is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, the activated carbon is filtered and removed, the obtained filtrate is decompressed and desolventized, the solvent is recovered, 220g of water is added into residues, the residues are heated to 70-80 ℃ for dissolution, the temperature is reduced to 0 ℃ for suction filtration, a white-like solid is obtained, drying is carried out, the purity was 99.3% and the yield was 91.2%. (by HPLC)
The analytical data were as in example 1.
Example 9
In a flask equipped with a condenser, 320g of DMAA, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylaminopyridine are sequentially added, stirring is started, the temperature is controlled to be below 45 ℃, 169g (1mol) of 2-chloro-5-chloromethylthiazole is dropwise added, after dropwise adding is finished, stirring is controlled at the temperature for 3 hours, discharging is carried out, potassium salt is centrifugally removed, filter cakes are rinsed by DMAA, 10g of activated carbon is added into obtained filtrate, stirring is carried out for 30 minutes at room temperature, the activated carbon is removed by filtration, the obtained filtrate is decompressed and desolventized, the solvent is recovered, 220g of water is added into residues, the temperature is raised to 70-80 ℃ for dissolution, the temperature is reduced to 0 ℃ for suction filtration, a white-like solid is obtained, drying is carried out, 264., the purity was 99.2% and the yield was 89.9%. (by HPLC)
The analytical data were as in example 1.
Example 10
Adding 800g of NMP, 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 25g (0.2mol) of 4-dimethylaminopyridine into a flask provided with a condenser in sequence, starting stirring, controlling the temperature to be about 25 ℃, dropwise adding 169g (1mol) of 2-chloro-5-chloromethylthiazole, controlling stirring at room temperature for 6 hours after dropwise adding, discharging, centrifuging to remove potassium salt, leaching a filter cake by using NMP, adding 20g of activated carbon into obtained filtrate, stirring at room temperature for 30 minutes, filtering to remove the activated carbon, decompressing and desolventizing the obtained filtrate, recovering the solvent, adding 220g of water into the remainder, heating to 70-80 ℃ for dissolving, cooling to 0 ℃ for suction filtration to obtain a white-like solid, drying to obtain 266.3g of a thiamethoxam finished product, the purity is 99.3 percent, and the yield is 90.6 percent. (by HPLC)
The analytical data were as in example 1.
Comparative example:
sequentially adding 800g of DMF (dimethyl formamide), 196g (1.2mol) of 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine, 209g (1.5mol) of potassium carbonate and 45g (0.2mol) of triethylbenzylammonium chloride into a flask provided with a condenser, starting stirring, controlling the temperature to be about 65 ℃, dropwise adding 169g (1mol) of 2-chloro-5-chloromethylthiazole, controlling the stirring for 8 hours at the temperature after the dropwise adding is finished, discharging, centrifuging to remove potassium salt, leaching a filter cake by using DMF, adding 20g of activated carbon into the obtained filtrate, stirring for 30 minutes at room temperature, filtering to remove the activated carbon, decompressing and desolventizing the obtained filtrate, recovering the solvent, adding 220g of water into the remainder, heating to 70-80 ℃ for dissolving, cooling to 0 ℃ for suction filtration to obtain a white-like solid, drying to obtain 270.0g of a thiamethoxam finished product with the purity of 97.4%, the yield thereof was found to be 90.0%.
The thiamethoxam product produced by the method is further detected, and the detection indexes and results are as follows:
as can be seen from the table, the thiamethoxam prepared by the method has the lowest content of 99.1 percent and the highest content of 99.4 percent.
As noted above, while the present invention has been shown and described with reference to certain preferred embodiments, it is not to be construed as limited thereto. Various changes in form and detail may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (9)
1. A preparation method of high-purity thiamethoxam is characterized in that 2-chloro-5-chloromethyl thiazole shown in a formula (II) and 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine shown in a formula (III) are reacted in a polar aprotic solvent by taking inorganic base as an acid-binding agent under the action of a catalyst, wherein the reaction temperature is 20-35 ℃; the reaction time is 5-6 hours; after the reaction is finished, filtering to remove inorganic salt, adding a decoloring agent into the filtrate, and stirring at room temperature for decoloring; filtering again, concentrating the filtrate under reduced pressure, recovering the solvent, adding water into the remainder, heating to full solution, cooling, crystallizing, filtering, and drying to obtain a white thiamethoxam product with a purity of more than 99% and a structure shown in formula (I);
the catalyst is 4-dimethylaminopyridine and Me-DABCO;
2. the method for preparing high-purity thiamethoxam according to claim 1, comprising: the mol ratio of the 2-chloro-5-chloromethylthiazole to the 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine to the inorganic base to the catalyst is 1:1.2 (0.5-2) to 0.001-1.
3. The method for preparing high-purity thiamethoxam according to claim 2, comprising: the mol ratio of the 2-chloro-5-chloromethylthiazole to the 3-methyl-4-nitroiminotetrahydro-1, 3, 5-oxadiazine to the inorganic base to the catalyst is 1:1.2 (1-1.5) to (0.005-0.2).
4. The method for preparing high-purity thiamethoxam according to claim 1, comprising: the weight ratio of the 2-chloro-5-chloromethyl thiazole to the decolorizing agent to the polar aprotic solvent is 1: 0.01-0.5 (1-10).
5. The method for preparing high-purity thiamethoxam according to claim 4, comprising: the weight ratio of the 2-chloro-5-chloromethyl thiazole to the decolorizing agent to the polar aprotic solvent is 1: 0.1-0.5 (5-10).
6. The method for preparing high-purity thiamethoxam according to claim 1, wherein the inorganic base is potassium carbonate.
7. The method for preparing high-purity thiamethoxam according to claim 1, wherein the polar aprotic solvent is an amide solvent or a ketone solvent.
8. The method for preparing high-purity thiamethoxam according to claim 7, wherein the polar aprotic solvent is one or more of DMAA, MIBK and NMP.
9. The method for preparing high-purity thiamethoxam according to claim 1, wherein the decolorizing agent is any one of activated carbon, diatomite and adsorption resin.
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