CN115521235B - Synthesis method of heptenone - Google Patents
Synthesis method of heptenone Download PDFInfo
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- CN115521235B CN115521235B CN202110705085.3A CN202110705085A CN115521235B CN 115521235 B CN115521235 B CN 115521235B CN 202110705085 A CN202110705085 A CN 202110705085A CN 115521235 B CN115521235 B CN 115521235B
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- extraction
- heptenone
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- JHHZQADGLDKIPM-UHFFFAOYSA-N hept-3-en-2-one Chemical compound CCCC=CC(C)=O JHHZQADGLDKIPM-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 61
- 239000000243 solution Substances 0.000 claims abstract description 56
- 239000003054 catalyst Substances 0.000 claims abstract description 52
- -1 thioether aldehyde Chemical class 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 claims abstract description 32
- 239000007864 aqueous solution Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 abstract description 10
- 238000002156 mixing Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 230000002572 peristaltic effect Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of chemical industry, in particular to a method for synthesizing heptenone, which comprises the following steps: under the action of a catalyst, the aqueous solution of sodium acetoacetate and the thioether aldehyde solution react by a cross-flow extraction method to prepare the heptenone. In the invention, sodium salt aqueous solution enters from the upper part of the extraction tower, thioether aldehyde oil solution enters from the lower part of the tower, and the catalyst is used for maintaining the pH value of the reaction. The oil phase is continuous phase, flows from the bottom of the tower to the top of the tower slowly and continuously, flows out from the top of the tower, is mixed with sodium salt aqueous solution after adding the catalyst in the process, and the catalyst and sodium salt combination are transferred to the oil phase for reaction, so that the motor provides necessary mixing. The heptenone obtained by the synthesis method has higher yield.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a method for synthesizing heptenone.
Background
The heptenone is a core intermediate of a large-tonnage herbicide, the main synthesis technology is that sodium acetoacetate and thioether aldehyde are synthesized by reaction, and intermittent dropwise addition type reaction is adopted, and the process flow is shown in figure 1. FIG. 1 is a flow chart of a prior art heptenone synthesis process. Batch operation is mainly to match the number of kettles according to the capacity, for example, 3 kettles with capacity of 1000 tons/year, and 3 kettles with capacity of 3KL are connected in parallel. And adding the catalyst solvent and sodium salt into a reaction kettle respectively, maintaining the reaction temperature, then dropwise adding thioether aldehyde, preserving heat after the dropwise adding is finished, and discharging after the heat preservation is finished. The ①②③ stage kettle in figure 1 operates consistently. The disadvantages of this process are: the ratio of sodium acetoacetate to thioether aldehyde is 1.3:1, the yield of heptenone is lower, the intermittent operation of dropwise addition, the reaction time is required to be several hours, the production efficiency is low, the occupied area of equipment is large, the liquid holdup is large, the safety risk is high, and the quality is unstable.
Disclosure of Invention
In view of the above, the technical problem to be solved by the invention is to provide a method for synthesizing heptenone, which has higher yield.
The invention provides a method for synthesizing heptenone, which comprises the following steps:
Under the action of a catalyst, the aqueous solution of sodium acetoacetate and the thioether aldehyde solution react by a cross-flow extraction method to prepare the heptenone.
Preferably, the cross-flow extraction is performed in an extraction column.
Preferably, the cross-flow extraction is performed in an extraction column (1):
the lower part of the extraction tower (1) is provided with a thioether aldehyde solution inlet (2);
The upper part of the extraction tower (1) is provided with an aqueous solution inlet (3) of sodium acetoacetate;
A plurality of catalyst inlets (4) are arranged on the tower body of the extraction tower (1);
a water phase outlet (5) is arranged at the bottom of the extraction tower (1);
an oil phase outlet (6) and a gas phase outlet (7) are arranged at the top of the extraction tower (1);
The extraction tower (1) also comprises a motor (8) for realizing cross-flow extraction.
Preferably, the catalyst inlet (4) is arranged on the tower body between the thioether aldehyde solution inlet (2) and the sodium acetoacetate aqueous solution inlet (3);
The number of the catalyst inlets (4) is 3-8.
Preferably, the ratio of the feed flow rate of the thioether aldehyde solution to the feed flow rate of the aqueous solution of sodium acetoacetate is 1kg/hr:1.1 to 1.4kg/hr.
Preferably, the catalyst comprises a piperidine solution of an acid;
the concentration of the piperidine solution of the acid is 5-20wt%.
Preferably, the catalyst comprises a piperidine solution of acetic acid, a piperidine solution of hydrochloric acid or a piperidine solution of sulfuric acid.
Preferably, the concentration of the aqueous solution of sodium acetoacetate is 25-35 wt%;
The concentration of the thioether aldehyde solution is 20-50 wt%;
the solvent of the thioether aldehyde solution is toluene.
Preferably, the temperature of the reaction is not lower than 20 ℃;
the pH value of the reaction is 5.5-8;
The reaction is a continuous reaction.
Preferably, the temperature of the reaction is 20 to 40 ℃.
The invention provides a method for synthesizing heptenone, which comprises the following steps: under the action of a catalyst, the aqueous solution of sodium acetoacetate and the thioether aldehyde solution react by a cross-flow extraction method to prepare the heptenone. In the invention, sodium salt aqueous solution enters from the upper part of the extraction tower, thioether aldehyde oil solution enters from the lower part of the tower, and the catalyst is used for maintaining the pH value of the reaction. The oil phase is continuous phase, flows from the bottom of the tower to the top of the tower slowly and continuously, flows out from the top of the tower, is mixed with sodium salt water solution after the catalyst is added in the process, and the catalyst and sodium salt combination are transferred to the oil phase for reaction, so that the motor provides necessary mixing, and the clear oil-water interface is maintained at the bottom of the tower. The heptenone obtained by the synthesis method has higher yield.
Drawings
FIG. 1 is a flow chart of a prior art heptenone synthesis process;
Fig. 2 is a schematic structural diagram of an extraction column (1) according to an embodiment of the present invention.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a method for synthesizing heptenone, which comprises the following steps:
Under the action of a catalyst, the aqueous solution of sodium acetoacetate and the thioether aldehyde solution react by a cross-flow extraction method to prepare the heptenone.
In the invention, the heptenone has a structure shown in formula (1):
in certain embodiments of the invention, the catalyst comprises a piperidine solution of an acid. In certain embodiments of the invention, the acid piperidine solution has a concentration of 5wt% to 20wt%. In certain embodiments, the acid piperidine solution has a concentration of 13.38wt%. In certain embodiments of the invention, the catalyst comprises a piperidine solution of acetic acid, a piperidine solution of hydrochloric acid, or a piperidine solution of sulfuric acid.
In the invention, the sodium acetoacetate has a structure shown in a formula (2):
in certain embodiments of the invention, the concentration of the aqueous solution of sodium acetoacetate is 25wt% to 35wt%. In certain embodiments, the aqueous solution of sodium acetoacetate has a concentration of 31.9wt%.
In the present invention, the thioether aldehyde has a structure represented by the formula (3):
in certain embodiments of the invention, the concentration of the thioether aldehyde solution is from 20% to 50% by weight. In certain embodiments, the concentration of the thioether aldehyde solution is 37.3 weight percent. In certain embodiments of the invention, the solvent of the thioether aldehyde solution is toluene.
In certain embodiments of the invention, the cross-flow extraction is performed in an extraction column. In certain embodiments of the invention, the extraction column is a rotating disk extraction column, a turbine extraction column, or kuhni column. In certain embodiments of the invention, the extraction column is an EC-type extraction column, and may specifically be an EC100-17 model extraction column, available from Shanghai Zhihua extraction technology Co.
In certain embodiments of the invention, the cross-flow extraction is performed in an extraction column (1):
the lower part of the extraction tower (1) is provided with a thioether aldehyde solution inlet (2);
The upper part of the extraction tower (1) is provided with an aqueous solution inlet (3) of sodium acetoacetate;
A plurality of catalyst inlets (4) are arranged on the tower body of the extraction tower (1);
a water phase outlet (5) is arranged at the bottom of the extraction tower (1);
an oil phase outlet (6) and a gas phase outlet (7) are arranged at the top of the extraction tower (1);
The extraction tower (1) also comprises a motor (8) for realizing cross-flow extraction.
Fig. 2 is a schematic structural diagram of an extraction column (1) according to an embodiment of the present invention.
In certain embodiments of the invention, the extraction column (1) has a column diameter of 100mm, a column height of 2m and an effective reaction volume of 15.7L.
In certain embodiments of the invention, the catalyst inlet (4) is disposed in the column between the thioether aldehyde solution inlet (2) and the aqueous sodium acetoacetate inlet (3).
In certain embodiments of the invention, the number of catalyst inlets (4) is 1-8. In certain embodiments of the invention, the number of catalyst inlets (4) is 3 to 8. In certain embodiments of the invention, the number of catalyst inlets (4) is 3, including a first catalyst inlet (4-1), a second catalyst inlet (4-2), and a third catalyst inlet (4-3).
In certain embodiments of the invention, on a scale, two adjacent catalyst inlets are spaced apart from 0.5 to 1m in the vertical direction.
In certain embodiments of the invention, the feed flow ratio of the thioether aldehyde solution to the aqueous solution of sodium acetoacetate is 1kg/hr:1.1 to 1.4kg/hr. In certain embodiments, the feed flow ratio of the thioether aldehyde solution to the aqueous solution of sodium acetoacetate is 1kg/hr:1.25kg/hr or 1kg/hr:1.23kg/hr.
In certain embodiments of the invention, the ratio of the feed flow rate of the thioether aldehyde solution to the feed flow rate of the catalyst is 1kg/hr: 0.2-0.3 kg/hr. In certain embodiments, the feed flow ratio of the thioether aldehyde solution to the catalyst is 1kg/hr:0.25kg/hr.
In certain embodiments of the invention, the feeding of the thioether aldehyde solution is controlled by a first peristaltic pump. The type of the first peristaltic pump is not particularly limited in the present invention, and peristaltic pumps known to those skilled in the art may be used.
In certain embodiments of the invention, the feeding of the aqueous solution of sodium acetoacetate is controlled by a second peristaltic pump. The type of the second peristaltic pump is not particularly limited in the present invention, and peristaltic pumps known to those skilled in the art may be used.
In certain embodiments of the invention, the feeding of the catalyst is controlled by a third peristaltic pump. In certain embodiments of the invention, where multiple catalyst inlets are included, multiple third peristaltic pumps may be employed to separately control the feed of catalyst at each catalyst inlet. The type of the third peristaltic pump is not particularly limited, and peristaltic pumps known to those skilled in the art may be used.
In certain embodiments of the invention, the temperature of the reaction is no less than 20 ℃. In certain embodiments of the invention, the temperature of the reaction is no less than 25 ℃. In certain embodiments of the invention, the temperature of the reaction is 20 to 40 ℃ or 20 to 35 ℃. In certain embodiments of the invention, the temperature of each feedstock feed is controlled to be 20-25 ℃ and the temperature at the outlet is controlled to be 30-35 ℃.
The pH of the reaction is controlled by the amount of acid added to the catalyst, and in certain embodiments of the invention, the pH of the reaction is from 5.5 to 8. In certain embodiments, the pH of the reaction is from 5.5 to 7.5.
In certain embodiments of the invention, the reaction is a continuous reaction.
In certain embodiments of the invention, the reaction is adiabatic without heat exchange.
In certain embodiments of the invention, the residence time of the cross-flow extraction is from 3 to 5 hours. In certain embodiments, the residence time of the cross-flow extraction is 4 hours.
In certain embodiments of the invention, each feed, prior to entering the extraction column, further comprises:
Toluene is adopted as a continuous phase, a water phase is adopted as a disperse phase, the whole tower is filled, and after the flow in the tower is stable, raw materials start to enter.
The source of the raw materials used in the present invention is not particularly limited, and may be generally commercially available.
In the invention, sodium salt aqueous solution enters from the upper part of the extraction tower, thioether aldehyde oil solution enters from the lower part of the tower, and the catalyst is used for maintaining the pH value of the reaction. The oil phase is continuous phase, flows from the bottom of the tower to the top of the tower slowly and continuously, flows out from the top of the tower, is mixed with sodium salt water solution after the catalyst is added in the process, and the catalyst and sodium salt combination are transferred to the oil phase for reaction, so that the motor provides necessary mixing, and the clear oil-water interface is maintained at the bottom of the tower. The heptenone obtained by the synthesis method has higher yield.
The invention adopts a continuous reaction technology, can reduce back mixing, improve reaction efficiency, improve the difference of main reaction rate and side reaction rate, further improve selectivity, simultaneously reduce energy consumption, improve production efficiency, reduce equipment floor area, reduce safety risk and improve site environment.
In order to further illustrate the present invention, the following examples are provided to illustrate a method for synthesizing heptenone according to the present invention, but should not be construed as limiting the scope of the present invention.
Example 1
Adopting an extraction tower of EC100-17 model shown in figure 1, wherein the diameter of the tower is 100mm, the height of the tower is 2 meters, and the effective reaction volume is 15.7L;
the lower part of the extraction tower (1) is provided with a thioether aldehyde solution inlet (2);
The upper part of the extraction tower (1) is provided with an aqueous solution inlet (3) of sodium acetoacetate;
A plurality of catalyst inlets (4) are arranged on the tower body of the extraction tower (1);
a water phase outlet (5) is arranged at the bottom of the extraction tower (1);
an oil phase outlet (6) and a gas phase outlet (7) are arranged at the top of the extraction tower (1);
The extraction tower (1) also comprises a motor (8) for realizing cross-flow extraction;
The catalyst inlet (4) is arranged on the tower body between the thioether aldehyde solution inlet (2) and the sodium acetoacetate aqueous solution inlet (3); the number of the catalyst inlets (4) is 3, and the catalyst comprises a first catalyst inlet (4-1), a second catalyst inlet (4-2) and a third catalyst inlet (4-3); adjacent two catalyst inlets are spaced apart by 0.5m along the vertical direction;
The reaction materials are toluene solution of thioether aldehyde and aqueous solution of sodium acetoacetate; the catalyst is piperidine solution of acetic acid, and is used for controlling the pH value of the reaction to be 5.5-7.5;
Feeding by 5 peristaltic pumps respectively;
the concentration of the aqueous solution of sodium acetoacetate was 31.9wt% and the feed rate was 2.11kg/hr;
the concentration of the toluene solution of thioether aldehyde was 37.3% by weight, and the feed rate was 1.68kg/hr;
the concentration of the piperidine solution of acetic acid was 13.38wt% with a total flow of 0.43kg/hr;
The feeding temperature of each material is controlled between 20 and 25 ℃, and the outlet temperature is controlled between 30 and 35 ℃; the process is adiabatic reaction, and heat exchange is not needed;
the retention time of the cross-flow extraction is 4h;
before entering the extraction tower, the raw materials further comprise: toluene is adopted as a continuous phase, a water phase is adopted as a disperse phase, a full tower is filled, and after the flow in the tower is stable, the feeding is started according to the set material flow;
After stable feeding for 8 hours, sampling and detecting the content of heptenone in the oil phase, wherein the content is 41.6wt% -42.0wt% and the flow is 1.85-1.95 kg/hr;
Meanwhile, the content of the heptenone in the water phase is measured to be 0.2 to 0.3 weight percent, and the flow is 2.25 to 2.35kg/hr;
Calculating the yield of the heptenone according to the material balance, wherein the yield of the heptenone is about 96% calculated by thioether aldehyde; the yield of heptenone, calculated as sodium acetoacetate, was about 85%.
Example 2
Compared with example 1, the flow rate of the aqueous solution of sodium acetoacetate was reduced to 2.06kg/hr, the other flow rates were kept unchanged, and the rest of the steps were carried out in accordance with the procedure of example 1;
After stabilization, sampling and detecting the content of heptenone in the oil phase, wherein the content is 41.6wt% -42.0wt% and the flow is 1.85-1.95 kg/hr;
Meanwhile, the content of the heptenone in the water phase is measured to be 0.2 to 0.3 weight percent, and the flow is 2.15 to 2.25kg/hr;
the yield of heptenone, calculated as thioether aldehyde, was calculated from this mass balance, being about 96%; the yield of heptenone, calculated as sodium acetoacetate, was about 87%.
Comparative example 1
A1000 mL flask was used, 405g of a 31.9wt% aqueous solution of sodium acetoacetate was added at a temperature of about 25-30℃and stirring was started, then a portion (22 g) of a 13wt% piperidine acetate solution was added, stirring was continued for 2 minutes, then, 283g of a 37.3wt% thioether solution was added, then 53g of a 13wt% piperidine acetate solution was added dropwise, and the mixture was kept at a temperature for 1 hour.
After the reaction is finished, the oil phase is obtained by layering, the content of the heptenone is 40.5-41.5 wt%, and the content of the heptenone in the water phase is 410g, and the content of the heptenone is 0.2-0.3 wt%.
Calculating the yield of the heptenone according to the material balance, wherein the yield of the heptenone is about 96% calculated by thioether aldehyde; the yield of heptenone, calculated as sodium acetoacetate, was about 74%.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (5)
1. A method for synthesizing heptenone, which comprises the following steps:
Under the action of a catalyst, the aqueous solution of sodium acetoacetate and the thioether aldehyde solution react by a cross-flow extraction method to prepare heptenone;
The cross-flow extraction is carried out in an extraction column (1):
the lower part of the extraction tower (1) is provided with a thioether aldehyde solution inlet (2);
the upper part of the extraction tower (1) is provided with an aqueous solution inlet (3) of sodium acetoacetate;
a plurality of catalyst inlets (4) are arranged on the tower body of the extraction tower (1);
The feed flow rate ratio of the thioether aldehyde solution to the aqueous solution of sodium acetoacetate was 1kg/hr:1.1 to 1.4 kg/hr;
the concentration of the aqueous solution of sodium acetoacetate is 25 wt% -35 wt%; the concentration of the thioether aldehyde solution is 20 wt% -50 wt%;
the catalyst comprises a piperidine solution of an acid; the concentration of the piperidine solution of the acid is 5 wt% -20 wt%;
the reaction temperature is 20-40 ℃, and the pH value is 5.5-8;
The reaction is a continuous reaction.
2. The synthesis method according to claim 1, wherein,
A water phase outlet (5) is arranged at the bottom of the extraction tower (1);
An oil phase outlet (6) and a gas phase outlet (7) are arranged at the top of the extraction tower (1);
the extraction tower (1) also comprises a motor (8) for realizing cross-flow extraction.
3. The synthesis method according to claim 2, wherein the catalyst inlet (4) is arranged in the tower between the thioether aldehyde solution inlet (2) and the sodium acetoacetate aqueous solution inlet (3);
the number of the catalyst inlets (4) is 3-8.
4. The method of synthesis according to claim 1, wherein the catalyst comprises a piperidine solution of acetic acid, a piperidine solution of hydrochloric acid or a piperidine solution of sulfuric acid.
5. The synthesis method according to claim 1, wherein,
The solvent of the thioether aldehyde solution is toluene.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101318919A (en) * | 2007-06-06 | 2008-12-10 | 中国石油天然气集团公司 | Process for synthesizing 6-ethyl mercapto-3-heptylene-2-ketone |
| CN101724509A (en) * | 2009-11-03 | 2010-06-09 | 南京工业大学 | Method for continuously preparing fatty acid ester by using tower reactor |
| CN206381990U (en) * | 2016-12-11 | 2017-08-08 | 河北兰升生物科技有限公司 | A kind of intermediate synthesis reaction vessel agitator of clethodim triketone |
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- 2021-06-24 CN CN202110705085.3A patent/CN115521235B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101318919A (en) * | 2007-06-06 | 2008-12-10 | 中国石油天然气集团公司 | Process for synthesizing 6-ethyl mercapto-3-heptylene-2-ketone |
| CN101724509A (en) * | 2009-11-03 | 2010-06-09 | 南京工业大学 | Method for continuously preparing fatty acid ester by using tower reactor |
| CN206381990U (en) * | 2016-12-11 | 2017-08-08 | 河北兰升生物科技有限公司 | A kind of intermediate synthesis reaction vessel agitator of clethodim triketone |
Non-Patent Citations (1)
| Title |
|---|
| 农药、医药中间体6-乙硫基-3-庚烯-2-酮的制备;王海峰等;沈阳化工学院学报;第21卷(第3期);P167-P169 * |
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