CN108003092B - Synthetic method of 2, 3-dichloropyridine - Google Patents
Synthetic method of 2, 3-dichloropyridine Download PDFInfo
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- CN108003092B CN108003092B CN201711388683.2A CN201711388683A CN108003092B CN 108003092 B CN108003092 B CN 108003092B CN 201711388683 A CN201711388683 A CN 201711388683A CN 108003092 B CN108003092 B CN 108003092B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
Abstract
The invention discloses a synthesis method of 2, 3-dichloropyridine, which comprises the steps of taking 2,3, 6-trichloropyridine as a raw material, hydrogen as a hydrogen source, tris (triphenylphosphine) rhodium chloride (I) or tris (triphenylphosphine) rhodium bromide (I) as a catalyst, adding an organic phosphine-containing auxiliary agent, and carrying out catalytic hydrogenation reaction at the pressure of 0.1-8 MPa and the temperature of 20-200 ℃ in the presence of a solvent and an acid-binding agent to obtain the 2, 3-dichloropyridine. According to the invention, by adding the cheap organic phosphine-containing auxiliary agent, under the condition of greatly reducing the dosage of the catalyst tris (triphenylphosphine) rhodium chloride (I) or tris (triphenylphosphine) rhodium bromide (I), good raw material 2,3, 6-trichloropyridine conversion rate and product 2, 3-dichloropyridine selectivity are obtained, the conversion rate of the 2,3, 6-trichloropyridine can reach 97%, the 2, 3-dichloropyridine selectivity is close to 90%, the manufacturing cost of the 2, 3-dichloropyridine is greatly reduced, and the industrial value is higher.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of 2, 3-dichloropyridine.
Background
2, 3-dichloropyridine is an important fine chemical intermediate and is a key intermediate for synthesizing a novel insecticide chlorantraniliprole.
JP1193246, CN103145609A and the like use 2,3, 6-trichloropyridine as a raw material, use one of palladium, platinum, ruthenium, Raney nickel or Raney copper as a catalyst, and reduce the 2,3, 6-trichloropyridine with a reducing agent such as hydrogen to obtain 2, 3-dichloropyridine, and have the problems that the single-pass conversion rate of the 2,3, 6-trichloropyridine and the selectivity of the 2, 3-dichloropyridine are not high, and the separation is difficult.
WO2017085476 uses 2,3, 6-trichloropyridine as a raw material and tris (triphenylphosphine) rhodium chloride (I) as a catalyst to carry out homogeneous catalytic hydrogenation reaction in the presence of an acid binding agent and a solvent to obtain the 2, 3-dichloropyridine. The method has high selectivity of 2, 3-dichloropyridine and overcomes the defect of adopting traditional palladium-carbon heterogeneous catalysts and the like. However, the catalyst amount in the system is large, the mass ratio of the catalyst to 2,3, 6-trichloropyridine is as high as 1:11, tris (triphenylphosphine) rhodium (I) chloride is an expensive catalyst, the 2, 3-dichloropyridine prepared by using the catalyst amount in the example of WO2017085476 is high in cost, and the industrial production value is not high. In view of the above, there is a need to improve the prior art, and to reduce the amount of catalyst used on the premise of ensuring the selectivity of 2, 3-dichloropyridine, thereby reducing the cost for preparing 2, 3-dichloropyridine.
Disclosure of Invention
The invention aims to provide a synthetic method of 2, 3-dichloropyridine aiming at the defects of the prior art. The purpose of the invention is realized by the following technical scheme:
a synthetic method of 2, 3-dichloropyridine comprises the steps of taking 2,3, 6-trichloropyridine as a raw material, hydrogen as a hydrogen source, tris (triphenylphosphine) rhodium chloride (I) or tris (triphenylphosphine) rhodium bromide (I) as a catalyst, adding an organic phosphine-containing auxiliary agent, and carrying out catalytic hydrogenation reaction under the reaction conditions of 0.1-8 MPa of pressure and 20-200 ℃ of temperature in the presence of a solvent and an acid-binding agent to obtain the 2, 3-dichloropyridine.
The molar ratio of the catalyst tris (triphenylphosphine) rhodium (I) chloride or tris (triphenylphosphine) rhodium (I) bromide to the 2,3, 6-trichloropyridine is at least 1:10000, and the increase of the using amount of the catalyst is helpful for improving the conversion rate and the selectivity of the 2, 3-dichloropyridine, but the cost is greatly increased due to excessive use; when the molar ratio is less than 1:10000, the reaction rate is very slow and the reaction hardly proceeds. In order to reduce the production cost of 2, 3-dichloropyridine and obtain satisfactory reaction effect, the molar ratio of the catalyst to the 2,3, 6-trichloropyridine is preferably 1:100 to 3000, and more preferably 1:200 to 2000.
The organic phosphine-containing auxiliary agent is one of triphenylphosphine, diphenyl (o-tolyl) phosphine, diphenyl (m-tolyl) phosphine, diphenyl (p-tolyl) phosphine (diphenyl-p-tolyl phosphine), bis (o-tolyl) phenylphosphine, bis (m-tolyl) phenylphosphine, bis (p-tolyl) phenylphosphine, tri (o-tolyl) phosphine, tri (m-tolyl) phosphine, tri (p-tolyl) phosphine, diphenylcyclohexylphosphine, dicyclohexylphenylphosphine, tricyclohexylphosphine, bis-diphenylphosphinomethane, 1, 2-bis (diphenylphosphino) ethane, 1, 3-bis (diphenylphosphino) propane and 1, 4-bis (diphenylphosphino) butane; triphenylphosphine is preferred. The addition of the organic phosphine-containing auxiliary agent can keep good raw material conversion rate and 2, 3-dichloropyridine selectivity under the condition of obviously reducing the dosage of the catalyst. The molar ratio of the organic phosphine-containing auxiliary agent to the catalyst is at least 1:1, when the molar ratio is more than 20:1, the effect on the reaction is equivalent to that achieved by 3-20: 1, and in order to avoid resource waste, the molar ratio of the organic phosphine-containing auxiliary agent to the catalyst is further preferably 5-15: 1.
The solvent is one or a mixture of at least two of aromatic hydrocarbons, alkanes, alcohols, ethers, esters or water; the aromatic hydrocarbon solvent is selected from toluene, benzene, xylene and pyridine; the alkane solvent is selected from normal hexane and cyclohexane; the alcohol solvent is selected from methanol, ethanol and isopropanol; the ether solvent is selected from tetrahydrofuran and diethyl ether; the ester solvent is selected from ethyl acetate, methyl acetate and butyl acetate.
Preferably, the solvent is one or a mixture of at least two of toluene, methanol, ethanol and isopropanol or a mixture of any one of methanol, ethanol and isopropanol and water.
The molar ratio of the acid-binding agent to the 2,3, 6-trichloropyridine is at least 1:1, and preferably 1.2-2: 1. The acid-binding agent is selected from organic alkali or inorganic alkali compounds. The organic alkali compound is selected from one of triethylamine, tetramethyl ethylene diamine, tetramethyl propylene diamine and pyridine; the inorganic alkali is selected from one of ammonia gas, alkali metal hydroxide or carbonate, bicarbonate and acetate; the alkali metal is sodium or potassium. Specifically, the inorganic base is selected from one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, and sodium acetate or potassium acetate.
Preferably, the organic base is triethylamine or pyridine, and the inorganic base is sodium acetate or sodium hydroxide.
Preferably, the reaction pressure is 0.4-3 MPa, and the temperature is 40-120 ℃.
Further preferably, the reaction pressure is 0.5-2.5 MPa, and the temperature is 75-110 ℃.
Compared with the prior art, the invention has the following beneficial effects:
compared with the technical scheme of the patent WO2017085476, the invention adds the cheap organic phosphine-containing auxiliary agent, and under the condition of greatly reducing the dosage of the catalyst tris (triphenylphosphine) rhodium chloride (I) or tris (triphenylphosphine) rhodium bromide (I), the good conversion rate of the raw material 2,3, 6-trichloropyridine and the selectivity of the product 2, 3-dichloropyridine are still obtained, the conversion rate of the 2,3, 6-trichloropyridine can reach 97 percent, and the selectivity of the 2, 3-dichloropyridine is close to 90 percent, so that the preparation cost of the 2, 3-dichloropyridine is greatly reduced, and the industrial value is higher. The product 2, 3-dichloropyridine prepared by the method can be separated by steam stripping, and the organic phosphine-containing auxiliary agent does not influence the purification treatment method.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 1
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine, 0.5g of tris (triphenylphosphine) rhodium (I) chloride and 1g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace air in the reaction kettle, hydrogen is introduced and the temperature is raised to 80 ℃ to carry out reaction after replacement is finished, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 20 hours, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 97%, the selectivity of the 2, 3-dichloropyridine is 89%, and the yield of the 2, 3-dichloropyridine is 86.3%.
Example 2
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine, 0.08g of tris (triphenylphosphine) rhodium (I) chloride and 0.2g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement, hydrogen is introduced and the temperature is raised to 83 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 26h, and the reaction is finished. Sampling and analyzing the conversion rate of the 2,3, 6-trichloropyridine to be 93 percent, the selectivity of the 2, 3-dichloropyridine to be 89 percent and the yield of the 2, 3-dichloropyridine to be 82.8 percent.
Example 3
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine, 0.08g of tris (triphenylphosphine) rhodium (I) chloride and 0.3g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement, hydrogen is introduced and the temperature is raised to 83 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 24 hours, and the reaction is finished. Sampling and analyzing the conversion rate of the 2,3, 6-trichloropyridine to be 95 percent, the selectivity of the 2, 3-dichloropyridine to be 90 percent and the yield of the 2, 3-dichloropyridine to be 85.5 percent.
Example 4
Adding 20g of 2,3, 6-trichloropyridine, 90g of isopropanol, 20g of triethylamine, 0.15g of tris (triphenylphosphine) rhodium (I) chloride and 0.4g of triphenylphosphine into a 250ml high-pressure reaction kettle, introducing nitrogen to replace air in the reaction kettle, introducing hydrogen, heating to 88 ℃ for reaction, gradually reducing the reaction pressure in the reaction process, adding hydrogen to maintain the reaction pressure between 1.0 and 1.2MPa, continuously reacting for 22h, and finishing the reaction. Sampling and analyzing the conversion rate of the 2,3, 6-trichloropyridine to be 95 percent, the selectivity of the 2, 3-dichloropyridine to be 88 percent and the yield of the 2, 3-dichloropyridine to be 83.6 percent.
Example 5
30g of 2,3, 6-trichloropyridine, 90g of methanol, 30g of triethylamine, 0.2g of tris (triphenylphosphine) rhodium (I) chloride and 0.4g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement, hydrogen is introduced and the temperature is raised to 75 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 2.0 and 2.2MPa, the reaction is continuously carried out for 18h, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 95%, the selectivity of the 2, 3-dichloropyridine is 87.8%, and the yield of the 2, 3-dichloropyridine is 83.4%.
Example 6
30g of 2,3, 6-trichloropyridine, 80g of ethanol, 10g of water, 30g of triethylamine, 0.2g of tris (triphenylphosphine) rhodium (I) chloride and 0.4g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 110 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.5 and 0.6MPa, the reaction is continuously carried out for 18 hours, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 95 percent, the selectivity of the 2, 3-dichloropyridine is 85.6 percent, and the yield of the 2, 3-dichloropyridine is 81.3 percent.
Example 7
30g of 2,3, 6-trichloropyridine, 90g of methanol, 20g of water, 10g of sodium hydroxide, 0.15g of tris (triphenylphosphine) rhodium (I) chloride and 0.4g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 83 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 16 hours, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 94 percent, the selectivity of the 2, 3-dichloropyridine is 85.1 percent, and the yield of the 2, 3-dichloropyridine is 80.0 percent.
Example 8
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine, 0.5g of tris (triphenylphosphine) rhodium (I) bromide and 1g of triphenylphosphine are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace air in the reaction kettle, hydrogen is introduced and the temperature is raised to 75 ℃ to carry out reaction after replacement, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 18h, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 96 percent, the selectivity of the 2, 3-dichloropyridine is 89.3 percent, and the yield of the 2, 3-dichloropyridine is 85.7 percent.
Comparative example 1
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine and 2.58g of tris (triphenylphosphine) rhodium (I) chloride are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 80 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 MPa and 1.0MPa, the reaction is continuously carried out for 20 hours, and the reaction is finished. Sampling and analyzing the conversion rate of 2,3, 6-trichloropyridine to be 99 percent, the selectivity of 2, 3-dichloropyridine to be 90 percent and the yield of 2, 3-dichloropyridine to be 89.1 percent.
Comparative example 2
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine and 0.5g of tris (triphenylphosphine) rhodium (I) chloride are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 80 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 20 hours, and the reaction is finished. Sampling analysis shows that the conversion rate of the 2,3, 6-trichloropyridine is 72 percent, the selectivity of the 2, 3-dichloropyridine is 82 percent, and the yield of the 2, 3-dichloropyridine is 59.0 percent.
Comparative example 3
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine and 0.08g of tris (triphenylphosphine) rhodium (I) chloride are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 83 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, and the reaction is continuously carried out for 24 hours, thus finishing the reaction. Sampling and analyzing: the conversion rate of 2,3, 6-trichloropyridine is 62%, the selectivity of 2, 3-dichloropyridine is 78%, and the yield of 2, 3-dichloropyridine is 48.3%.
Comparative example 4
30g of 2,3, 6-trichloropyridine, 90g of ethanol, 30g of triethylamine and 0.5g of tris (triphenylphosphine) rhodium bromide (I) are put into a 250ml high-pressure reaction kettle, nitrogen is introduced to replace the air in the reaction kettle, after replacement is finished, hydrogen is introduced and the temperature is raised to 75 ℃ for reaction, the reaction pressure is gradually reduced in the reaction process, hydrogen is added to maintain the reaction pressure between 0.8 and 1.0MPa, the reaction is continuously carried out for 18 hours, and the reaction is finished. Sampling and analyzing the conversion rate of the 2,3, 6-trichloropyridine to be 74 percent, the selectivity of the 2, 3-dichloropyridine to be 80 percent and the yield of the 2, 3-dichloropyridine to be 59.2 percent.
Compared with the example 1, the method has the advantages that the conversion rate of the raw materials and the selectivity of the target product can be obviously improved by adding the organic phosphine-containing auxiliary agent triphenylphosphine under the condition of greatly reducing the using amount of the catalyst, and the effect which is basically equivalent to that of the comparative example 1 is basically obtained; the use amount of expensive tris (triphenylphosphine) rhodium chloride (I) catalyst can be greatly reduced, and the production cost of the 2, 3-dichloropyridine is greatly reduced. Comparing the comparative example 2 with the example 1, comparing the comparative example 3 with the examples 2 and 3, and comparing the comparative example 4 with the example 8, it can be known that the conversion rate of the raw material 2,3, 6-trichloropyridine and the selectivity and the yield of the target product 2, 3-dichloropyridine can be obviously improved by adding the organic phosphine-containing auxiliary triphenylphosphine; within the dosage range of the invention, with the increase of the dosage of the organic phosphine-containing auxiliary agent, the conversion rate of the raw material 2,3, 6-trichloropyridine and the yield of the target product 2, 3-dichloropyridine are also increased.
Claims (9)
1. A synthetic method of 2, 3-dichloropyridine is characterized in that in the presence of a solvent and an acid-binding agent, 2,3, 6-trichloropyridine is used as a raw material, hydrogen is used as a hydrogen source, tris (triphenylphosphine) rhodium chloride (I) or tris (triphenylphosphine) rhodium bromide (I) is used as a catalyst, and an organic phosphine-containing auxiliary agent is added to perform a catalytic hydrogenation reaction under the reaction conditions of 0.1-8 MPa of pressure and 20-200 ℃ to obtain 2, 3-dichloropyridine; wherein the organic phosphine-containing auxiliary agent is one of triphenylphosphine, diphenyl (o-tolyl) phosphine, diphenyl (m-tolyl) phosphine, diphenyl (p-tolyl) phosphine, bis (o-tolyl) phenylphosphine, bis (m-tolyl) phenylphosphine, bis (p-tolyl) phenylphosphine, tri (o-tolyl) phosphine, tri (m-tolyl) phosphine and tri (p-tolyl) phosphine; the molar ratio of the catalyst to the 2,3, 6-trichloropyridine is 1: 100-3000; the molar ratio of the organic phosphine-containing auxiliary agent to the catalyst is 3-20: 1.
2. The method of synthesizing 2, 3-dichloropyridine according to claim 1, wherein; the molar ratio of the acid-binding agent to the 2,3, 6-trichloropyridine is 1.2-2: 1.
3. The method for synthesizing 2, 3-dichloropyridine according to claim 1, wherein the molar ratio of the catalyst to the 2,3, 6-trichloropyridine is 1: 200-2000; the molar ratio of the organic phosphine-containing auxiliary agent to the catalyst is 5-15: 1.
4. The method of claim 1, wherein the organic phosphine promoter is triphenylphosphine.
5. The method for synthesizing 2, 3-dichloropyridine according to claim 1, wherein the solvent is selected from one or a mixture of at least two of aromatic hydrocarbons, alkanes, alcohols, ethers, esters and water;
the aromatic hydrocarbon solvent is selected from toluene, benzene, xylene and pyridine;
the alkane solvent is selected from normal hexane and cyclohexane; the alcohol solvent is selected from methanol, ethanol and isopropanol; the ether solvent is selected from tetrahydrofuran and diethyl ether;
the ester solvent is selected from ethyl acetate, methyl acetate and butyl acetate.
6. The method for synthesizing 2, 3-dichloropyridine according to claim 5, wherein the solvent is one or a mixture of at least two of toluene, methanol, ethanol and isopropanol or a mixture of any one of methanol, ethanol and isopropanol and water.
7. The method for synthesizing 2, 3-dichloropyridine according to claim 1, wherein the acid-binding agent is selected from organic base or inorganic base compound;
the organic alkali compound is selected from one of triethylamine, tetramethyl ethylene diamine, tetramethyl propylene diamine and pyridine;
the inorganic alkali is selected from one of ammonia gas, alkali metal hydroxide or carbonate, bicarbonate and acetate; the alkali metal is sodium or potassium.
8. The method for synthesizing 2, 3-dichloropyridine according to claim 7, wherein the acid-binding agent is selected from triethylamine or pyridine, sodium acetate or sodium hydroxide.
9. The method for synthesizing 2, 3-dichloropyridine according to claim 1, wherein the reaction pressure is 0.4-3 MPa and the temperature is 40-120 ℃.
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