CN110862310A - Synthesis method of cyclopropyl methyl ketone - Google Patents
Synthesis method of cyclopropyl methyl ketone Download PDFInfo
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- CN110862310A CN110862310A CN201911235730.9A CN201911235730A CN110862310A CN 110862310 A CN110862310 A CN 110862310A CN 201911235730 A CN201911235730 A CN 201911235730A CN 110862310 A CN110862310 A CN 110862310A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
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Abstract
The invention relates to a synthesis method of cyclopropyl methyl ketone, which comprises the following steps: 1) carrying out hydro-hydrolysis on 2-methylfuran by adopting a one-pot method in the presence of a hydrogenation catalyst, hydrogen and water to prepare acetyl-n-propanol; 2) performing hydrochloric acid chlorination reaction on the acetyl-n-propanol prepared in the step 1) to prepare 5-chloro-2-pentanone; 3) performing a ring closing reaction on the crude product of the 5-chloro-2-pentanone prepared in the step 2) under an alkaline condition to obtain the cyclopropyl methyl ketone. The synthesis method of the cyclopropyl methyl ketone takes 2-methylfuran as a raw material, and the cyclopropyl methyl ketone is prepared through one-pot hydrogenation hydrolysis, hydrochloric acid chlorination reaction and ring closing reaction, so that the process is simple and smooth, the reaction condition is mild, and the method is suitable for industrial amplification production; 2-methylfuran is adopted as a raw material, so that the atom economy is high, the environment is protected, and the raw material cost is low.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a synthetic method of cyclopropyl methyl ketone.
Background
Cyclopropyl methyl ketone is an important raw material of the bactericide cyproconazole, and the problems of complex process, high raw material cost, high difficulty in industrial amplification production and the like exist in the existing synthesis process. 5-chloro-2-pentanone or acetylbutyrolactone used as a raw material as reported in patents CN200610098154 and CN201210099170 has too high raw material cost and low economic benefit; CN201611008606 patent reports that 2-methylfuran obtained by hydrogenation is re-isomerized into cyclopropyl methyl ketone, catalyst is expensive, yield is too low, and raw material cost is high; and as reported in patent CN201511010127, acetyl butyrolactone is used as a raw material, and is cracked at high temperature to obtain cyclopropyl methyl ketone, and the raw material, solvent and catalyst have high cost and harsh conditions, and are not suitable for industrialization.
Therefore, the problem to be solved by the technical personnel in the field is to find a synthesis process of cyclopropyl methyl ketone, which has simple and smooth process, low cost and suitable industrialized scale-up production.
Disclosure of Invention
The invention provides a synthesis method of cyclopropyl methyl ketone, aiming at solving the problems of complex process, high raw material cost, high difficulty in industrial amplification production and the like in the existing synthesis process of cyclopropyl methyl ketone.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a synthesis method of cyclopropyl methyl ketone, which comprises the following steps:
(1) carrying out hydro-hydrolysis on 2-methylfuran by adopting a one-pot method in the presence of a hydrogenation catalyst, hydrogen and water to prepare acetyl-n-propanol;
(2) performing hydrochloric acid chlorination reaction on the acetyl-n-propanol prepared in the step (1) to prepare 5-chloro-2-pentanone;
(3) and (3) performing a ring closing reaction on the crude product of the 5-chloro-2-pentanone prepared in the step (2) under an alkaline condition to obtain cyclopropyl methyl ketone.
Further, in the step (1), the hydrogenation catalyst is a metal catalyst containing palladium, platinum or nickel.
Further preferably, the metal catalyst is a palladium carbon catalyst, wherein the mass percent of palladium is 1-50 wt%.
Further preferably, the mass percentage of palladium in the palladium on carbon catalyst is 5 to 10 wt%.
Further, in the step (1), the temperature of the hydrogenation hydrolysis is 0-50 ℃, the pressure is 0.01-0.4MPa, and the hydrogenation time is 1-5 h.
Further preferably, in the step (1), the temperature of the hydrogenation hydrolysis is 20-30 ℃, the pressure is 0.1-0.3MPa, and the hydrogenation time is 2-3 h.
Further, in the step (1), the mass ratio of the hydrogenation catalyst, the 2-methylfuran and the water is 1 (50-3000) to (50-3000).
Further preferably, the mass ratio of the hydrogenation catalyst, the 2-methylfuran and the water is 1 (50-1000) to (50-1000).
Further, the step (2) is specifically: and dropwise adding the obtained acetyl-n-propanol into heated hydrochloric acid, performing azeotropic distillation while dropwise adding to obtain a product 5-chloro-2-pentanone, and standing for layering to obtain a crude product 5-chloro-2-pentanone.
Further preferably, the solubility of the hydrochloric acid is 10% -30%, and the heating temperature is 80-100 ℃.
Further preferably, the solubility of the hydrochloric acid is 15% -20%, and the heating temperature is 90-95 ℃.
Further preferably, the molar ratio of the acetyl-n-propanol to the hydrochloric acid is 1: 1.5-4.0.
Further preferably, the molar ratio of the acetyl-n-propanol to the hydrochloric acid is 1: 2.0-3.0.
Further, in the step (3), the alkali used in the alkaline condition is sodium hydroxide, potassium hydroxide or calcium hydroxide, and the concentration of the alkali is 5-30%.
Further preferably, the concentration of the base is 15-20%.
Further preferably, the base is sodium hydroxide.
Further, in the step (3), the temperature of the ring closing reaction is 50-100 ℃, and the reaction time is 1-5 h; the molar ratio of the 5-chloro-2-pentanone to the base is 1: 1.01-3.0.
Further preferably, the temperature of the ring closing reaction is 70-80 ℃, and the reaction time is 2 h; the molar ratio of the 5-chloro-2-pentanone to the base is 1: 1.5-2.0.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the synthesis method of the cyclopropyl methyl ketone takes 2-methylfuran as a raw material, and the cyclopropyl methyl ketone is prepared through one-pot hydrogenation hydrolysis, hydrochloric acid chlorination reaction and ring closing reaction, so that the process is simple and smooth, the reaction condition is mild, and the method is suitable for industrial amplification production; 2-methylfuran is adopted as a raw material, so that the atom economy is high, the environment is protected, and the raw material cost is low.
Drawings
FIG. 1 is a scheme showing the synthesis of cyclopropyl methyl ketone according to the present invention.
Detailed Description
The present invention will be described in detail and specifically with reference to the following examples to facilitate better understanding of the present invention, but the following examples do not limit the scope of the present invention.
Example 1
Synthesis of cyclopropyl methyl ketone: adding 400g of 2-methylfuran, 100g of water and 2g of 5% palladium-carbon catalyst into a 1000ml hydrogenation kettle, replacing with hydrogen after nitrogen replacement, stirring to control the reaction temperature to be 28 ℃, continuously hydrogenating with a hydrogen balloon, finishing after 3 hours of reaction, filtering reaction liquid after nitrogen replacement, mechanically using the catalyst for the next batch, standing and layering the reaction liquid, and mechanically using a water layer for the next batch; the organic phase, i.e., n-propanol, was 448g, 95.3% pure.
340g of 20% hydrochloric acid was added to a 1000ml three-necked flask, and heated to 90 ℃ to add 100g of the above acetyl-n-propanol dropwise while collecting 5-chloro-2-pentanone and dilute acid water as an azeotrope by distillation. After the dropwise addition is finished, continuously distilling until no organic phase is evaporated, standing and layering to obtain 130g of crude 5-chloro-2-pentanone with the purity of 96.1% as an organic phase; the aqueous layer can be used for the next batch of chlorination reaction.
Adding 100g of the 5-chloro-2-pentanone and 318g of 20% sodium hydroxide into a 1000ml three-necked bottle, stirring and heating to 75 ℃, reacting for 2 hours, standing and layering to obtain 65g of cyclopropyl methyl ketone as an organic phase,1HNMR(400MHz,CDCl3) δ 2.08(s,3H),1.98(m,1H),0.81-0.56(m,4H), purity 97.5%.
Example 2
Synthesis of cyclopropyl methyl ketone: adding 400g of 2-methylfuran, 100g of water and 2g of 10% palladium-carbon catalyst into a 1000ml hydrogenation kettle, replacing with hydrogen after nitrogen replacement, stirring to control the reaction temperature to be 30 ℃, continuously hydrogenating with a hydrogen balloon, finishing the reaction after 2.5 hours, filtering the reaction solution after nitrogen replacement, mechanically using the catalyst for the next batch, standing and layering the reaction solution, and mechanically using the water layer for the next batch; the organic phase, i.e., n-propanol, 448g had a purity of 95.5%.
In a 1000ml three-necked flask, 340g of 15% hydrochloric acid was added, heated to 92 ℃ and 100g of the above acetyl-n-propanol was added dropwise while collecting 5-chloro-2-pentanone and dilute acid water as azeotropes by distillation. After the dropwise addition is finished, continuously distilling until no organic phase is evaporated, standing and layering to obtain 130g of 5-chloro-2-pentanone with the purity of 96.2% from the organic phase; the aqueous layer can be used for the next batch of chlorination reaction.
And (3) adding 100g of the 5-chloro-2-pentanone and 318g of 20% sodium hydroxide into a 1000ml three-necked bottle, stirring and heating to 70 ℃, reacting for 2 hours, and standing for layering to obtain 65g of cyclopropyl methyl ketone with the purity of 97.4% as an organic phase.
Example 3
Synthesis of cyclopropyl methyl ketone: adding 400g of 2-methylfuran, 100g of water and 2g of 10% palladium-carbon catalyst into a 1000ml hydrogenation kettle, replacing with hydrogen after nitrogen replacement, stirring to control the reaction temperature to be 25 ℃, continuously hydrogenating with a hydrogen balloon, finishing after 2 hours of reaction, filtering the reaction solution after nitrogen replacement, mechanically using the catalyst for the next batch, standing and layering the reaction solution, and mechanically using the water layer for the next batch; the organic phase, i.e., n-propanol, 448g had a purity of 95.2%.
In a 1000ml three-necked flask, 340g of 20% hydrochloric acid was added, heated to 95 ℃ and 100g of the above acetyl-n-propanol was added dropwise while collecting the azeotrope of 5-chloro-2-pentanone and dilute acid water by distillation. After the dropwise adding is finished, continuously distilling until no organic phase is distilled out, standing and layering to obtain 130g of 5-chloro-2-pentanone with the purity of 96%; the aqueous layer can be used for the next batch of chlorination reaction.
And (3) adding 100g of the 5-chloro-2-pentanone and 318g of 20% sodium hydroxide into a 1000ml three-necked bottle, stirring and heating to 80 ℃, reacting for 2 hours, and standing for layering to obtain 65g of cyclopropyl methyl ketone with the purity of 97.1% as an organic phase.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (18)
1. A synthesis method of cyclopropyl methyl ketone is characterized by comprising the following steps:
(1) carrying out hydro-hydrolysis on 2-methylfuran by adopting a one-pot method in the presence of a hydrogenation catalyst, hydrogen and water to prepare acetyl-n-propanol;
(2) performing hydrochloric acid chlorination reaction on the acetyl-n-propanol prepared in the step (1) to prepare 5-chloro-2-pentanone;
(3) and (3) performing a ring closing reaction on the crude product of the 5-chloro-2-pentanone prepared in the step (2) under an alkaline condition to obtain cyclopropyl methyl ketone.
2. The method for synthesizing cyclopropyl methyl ketone according to claim 1, wherein in step (1), the hydrogenation catalyst is a metal catalyst containing palladium, platinum or nickel.
3. The method for synthesizing cyclopropyl methyl ketone according to claim 2, wherein the metal catalyst is palladium carbon catalyst, wherein the mass percent of palladium is 1-50 wt%.
4. The method for synthesizing cyclopropyl methyl ketone according to claim 3, wherein the palladium on carbon catalyst is 5 to 10 wt% palladium.
5. The synthesis method of cyclopropyl methyl ketone according to claim 1, wherein in step (1), the temperature of the hydrogenation hydrolysis is 0-50 ℃, the pressure is 0.01-0.4MPa, and the hydrogenation time is 1-5 h.
6. The synthesis method of cyclopropyl methyl ketone according to claim 5, wherein in step (1), the temperature of the hydrogenation hydrolysis is 20-30 ℃, the pressure is 0.1-0.3MPa, and the hydrogenation time is 2-3 h.
7. The method for synthesizing cyclopropyl methyl ketone according to claim 1, wherein in step (1), the mass ratio of the hydrogenation catalyst, 2-methyl furan and water is 1 (50-3000) to (50-3000).
8. The synthesis method of cyclopropyl methyl ketone as claimed in claim 7, wherein the mass ratio of the hydrogenation catalyst, 2-methyl furan and water is 1 (50-1000) to (50-1000).
9. The synthesis method of cyclopropyl methyl ketone according to claim 1, wherein the step (2) is specifically: and dropwise adding the obtained acetyl-n-propanol into heated hydrochloric acid, performing azeotropic distillation while dropwise adding to obtain a product 5-chloro-2-pentanone, and standing for layering to obtain a crude product 5-chloro-2-pentanone.
10. The method for synthesizing cyclopropyl methyl ketone according to claim 9, wherein the solubility of hydrochloric acid is 10% to 30%, and the heating temperature is 80 to 100 ℃.
11. The method for synthesizing cyclopropyl methyl ketone according to claim 10, wherein the solubility of hydrochloric acid is 15% to 20%, and the heating temperature is 90 to 95 ℃.
12. The method for synthesizing cyclopropyl methyl ketone according to claim 9, wherein the molar ratio of acetyl n-propanol to hydrochloric acid is 1: 1.5-4.0.
13. The method for synthesizing cyclopropyl methyl ketone according to claim 12, wherein the molar ratio of acetyl n-propanol to hydrochloric acid is 1: 2.0-3.0.
14. The method for synthesizing cyclopropyl methyl ketone according to claim 1, wherein in step (3), the alkali used in the alkaline condition is sodium hydroxide, potassium hydroxide or calcium hydroxide, and the concentration thereof is 5-30%.
15. The method of claim 14, wherein the concentration of the base is 15-20%.
16. The method of claim 14, wherein the base is sodium hydroxide.
17. The synthesis method of cyclopropyl methyl ketone according to claims 1 and 14, wherein in step (3), the temperature of the ring closing reaction is 50-100 ℃, and the reaction time is 1-5 h; the molar ratio of the 5-chloro-2-pentanone to the base is 1: 1.01-3.0.
18. The synthesis method of cyclopropyl methyl ketone according to claim 17, wherein the temperature of the ring closing reaction is 70-80 ℃ and the reaction time is 2 h; the molar ratio of the 5-chloro-2-pentanone to the base is 1: 1.5-2.0.
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Cited By (5)
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CN112717988A (en) * | 2021-02-07 | 2021-04-30 | 郑州大学 | Efficient pollution-free catalyst for preparing acetyl-n-propanol and preparation method and use method thereof |
CN113072434A (en) * | 2021-04-01 | 2021-07-06 | 上海创诺医药集团有限公司 | Method for preparing cyclopropyl methyl ketone by one-step method |
CN113582824A (en) * | 2021-08-26 | 2021-11-02 | 江苏清泉化学股份有限公司 | Preparation method of high-purity cyclopropyl methyl ketone |
CN113816841A (en) * | 2021-10-12 | 2021-12-21 | 瑞孚信江苏药业股份有限公司 | Preparation method of cyclopropyl methyl ketone |
CN115850039A (en) * | 2022-12-01 | 2023-03-28 | 江苏中旗科技股份有限公司 | Method for synthesizing cyclopropyl methyl ketone through imine intermediate |
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CN113816841A (en) * | 2021-10-12 | 2021-12-21 | 瑞孚信江苏药业股份有限公司 | Preparation method of cyclopropyl methyl ketone |
CN115850039A (en) * | 2022-12-01 | 2023-03-28 | 江苏中旗科技股份有限公司 | Method for synthesizing cyclopropyl methyl ketone through imine intermediate |
CN115850039B (en) * | 2022-12-01 | 2024-01-02 | 江苏中旗科技股份有限公司 | Method for synthesizing cyclopropylmethyl ketone through imine intermediate |
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