CN108821957B - Continuous synthesis method of cinnamaldehyde - Google Patents
Continuous synthesis method of cinnamaldehyde Download PDFInfo
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Abstract
The invention discloses a continuous synthesis method of cinnamaldehyde, which comprises the steps of mixing benzaldehyde and acetaldehyde with a nonpolar organic solvent, taking a strong alkali aqueous solution as a catalyst, and carrying out countercurrent reaction extraction in an extraction tower to obtain the cinnamaldehyde. The invention improves the conversion rate, selectivity and yield of the aldol condensation reaction by adding the nonpolar organic solvent in the aldol condensation reaction, and enables the aldol condensation reaction to realize continuous production in the extraction equipment. After the reaction is finished, the strong alkali aqueous solution can be directly used after dehydration, thereby achieving the purpose of reducing the discharge of waste water.
Description
Technical Field
The invention relates to the field of fine organic chemical synthesis, in particular to synthesis of a fine chemical intermediate cinnamaldehyde.
Background
Cinnamaldehyde (3-phenyl-2-propenal) english name: the Cinnamdehyde is an important chemical and medical intermediate, and has an extremely wide application range. The method is used for synthesizing a series of products such as a-bromo cinnamaldehyde, cinnamyl alcohol, cinnamic acid, cinnamonitrile and the like in the field of organic synthesis. The product can be used as flavoring material in essence and spice industry to make main spice fragrant. They are often used as fixatives because they have a higher boiling point than other organic materials with similar molecular structures. In the fields of food, feed, preservative and the like, the cinnamaldehyde also has wide application. The chemical synthesis reaction of cinnamaldehyde is as follows:
the common synthesis method is that benzaldehyde, acetaldehyde, strong base and solvent (alcohol) are put into a reaction kettle, hot water is introduced into a jacket of the reaction kettle for heating, and acetaldehyde and benzaldehyde undergo aldol condensation reaction under the catalytic action of the strong base to form cinnamaldehyde.
After the reaction, adding an extraction solvent, and washing the reaction solution by dilute acid water and deionized water in sequence. And recovering the solvent from the washed reaction solution to obtain a cinnamaldehyde crude product, and rectifying the crude product in a rectifying tower to obtain the cinnamaldehyde meeting the quality requirement.
In the general synthesis method, strong bases such as solid NaOH and KOH are used as catalysts for aldol condensation reaction, the principle of strong base catalysis is that acetaldehyde is ionized to generate alpha-carbanion under the action of alkali, the alpha-carbanion and carbonyl of benzaldehyde undergo nucleophilic addition reaction, and then undergo elimination reaction to form cinnamaldehyde. The strong alkalinity of the catalyst is easy to initiate reaction, but too strong alkalinity can initiate excessive alpha-carbanions to accelerate the aldol condensation side reaction of acetaldehyde, and too strong alkalinity can also promote the disproportionation reaction of benzaldehyde to form benzyl alcohol, benzoic acid and other side reactions.
The main side reactions are as follows:
1. aldol condensation side reactions of acetaldehyde itself:
2. disproportionation of benzaldehyde:
3. other more complex chemical reactions:
in addition to the main side reactions of the above 1, 2, condensation reaction of benzaldehyde with a multi-molecular acetaldehyde condensate, self-condensation side reaction of more acetaldehyde, polymerization side reaction of enal, and the like may occur.
Therefore, a mixture of cinnamaldehyde and a series of by-products as described above is obtained in the synthesis reaction of cinnamaldehyde. Patent CN105152891A improves the conventional synthesis method and adopts solid superbase as catalyst to synthesize cinnamaldehyde by fixed bed reaction. Compared with the conventional process, the process scheme can omit the dilute acid water washing process, reduce the generation of waste water and has certain environmental protection advantage. However, the fixed bed reactor is easy to be industrially scaled up in the gas-solid reaction, and the liquid-solid reaction is difficult to be industrially scaled up due to back mixing. The patent CN1260194C adopts aldol condensation reaction for synthesizing cinnamaldehyde under the near-critical state (200 ℃ and 300 ℃ and 10-20MPa) without an alkaline catalyst, an organic solvent and a large proportion of water, and the synthesis method reduces the concentration of carbanions formed by acetaldehyde and improves the selectivity. Because the conversion rate is extremely low without the catalytic action of the alkaline catalyst, the yield is only 16.6 percent at most, and the industrial production is difficult to realize.
In summary, the above conventional cinnamic aldehyde synthesis method has the following disadvantages:
1. the conversion rate of the main raw material benzaldehyde is low, and the selectivity is poor;
2. the byproducts are many, and the post-treatment is difficult;
3. the wastewater amount is large, and the wastewater treatment cost is high;
4. intermittent production, low equipment utilization rate and low productivity.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects in the prior art, improve the conversion rate and selectivity of the cinnamaldehyde synthesis reaction, improve the quality of cinnamaldehyde, reduce the quantity of three wastes and improve the productivity of unit equipment by adopting a continuous technology.
In order to solve the technical problems, the invention adopts the following technical scheme:
a continuous synthesis method of cinnamaldehyde comprises the following steps: in the extraction tower, the mixture of benzaldehyde, acetaldehyde and non-polar organic solvent and strong alkali water solution are subjected to continuous aldol condensation reaction to synthesize cinnamaldehyde.
Preferably, the mass concentration of the strong base in the strong base water solution is 1-20%.
Preferably, the feeding mass ratio of the benzaldehyde to the strong alkali aqueous solution is 1: 0.5-15.0.
Preferably, the density of the nonpolar organic solvent is less than or equal to 0.95g/cm3。
Further preferably, the boiling point range of the nonpolar organic solvent is: the boiling point of the nonpolar organic solvent is more than or equal to 40 ℃ and less than or equal to 150 ℃.
Still further preferably, the nonpolar organic solvent includes at least one of cyclohexane, n-hexane, n-heptane, petroleum ether, gasoline, benzene, toluene, and xylene.
Preferably, the mass ratio of the benzaldehyde to the non-polar organic solvent is 1: 0.5-15.0.
Preferably, the extraction tower comprises a rotating disc tower with an internal coil or an external sleeve, a reciprocating sieve plate tower and a pulse packed tower.
The main principle of the invention is as follows:
firstly, the invention adopts a two-phase reaction mode to improve the conversion rate and selectivity of the reaction, and the main raw materials of benzaldehyde and acetaldehyde are dissolved in a non-polar organic solvent to carry out two-phase reaction with a strong alkali aqueous solution, so that the mode avoids the benzaldehyde contacting the strong alkali aqueous solution for a long time, and reduces the side reaction of the benzaldehyde contacting with the strong alkali. The raw material acetaldehyde has certain dissolving capacity in an organic phase and a water phase, the concentration of the raw material acetaldehyde in the water phase is reduced by adding a non-polar organic solvent, the contact time of the acetaldehyde and a strong alkali aqueous solution is reduced, and a series of side reactions of the acetaldehyde under the action of strong alkali are reduced; secondly, the aldol condensation reaction is carried out in an extraction column capable of controlling the reaction temperature and the mixing speed of the two phases. The nonpolar organic solvent phase for dissolving benzaldehyde and acetaldehyde is fully mixed with the strong alkali water solution phase by using external energy in the extraction section, the mixture is controlled to react near the optimal temperature, and the density difference of the two phases is used for separation in the standing clarification section, so that the continuous reaction is realized, and the capacity of equipment is improved; finally, the strong alkali aqueous solution is continuously applied, and the wastewater discharge is reduced. A small amount of acetaldehyde in the strong alkali aqueous solution can be recycled, so that the loss of the acetaldehyde is reduced.
According to the invention, 1-20% of strong alkali aqueous solution is used as a reaction catalyst, and side reactions are increased when the concentration of strong alkali is too high; if the concentration is too low, the reaction rate is slow, and it is difficult to achieve continuous operation in the extraction column. The selectivity, the conversion rate, the yield and the productivity are comprehensively considered, and an ideal reaction effect can be obtained by adopting the catalyst concentration of 1-20%.
The reaction solvent mainly has the function of providing a two-phase reaction medium, and the two-phase reaction medium has enough solubility for benzaldehyde and acetaldehyde, and the concentration of benzaldehyde and acetaldehyde in the strong alkali aqueous solution is reduced. The density of the solvent is less than that of water, which is beneficial to the layering of an organic phase and a water phase after the reaction is finished. The density adopted by the invention is less than or equal to 0.95g/cm3The non-polar organic solvent can be well layered with a strong alkaline aqueous solution, and has the advantages of low viscosity, stable chemical property and low loss. Further consideration is given to the fact that the boiling point of the solvent is appropriate, and the boiling point is too low, so that the loss is large and the recovery rate is low in the reaction and separation processes; too high a boiling point causes less work-up in the solvent recovery processThe mass product is brought into a solvent system, the treatment is troublesome, and the invention adopts the following steps: the solvent with the boiling point range of the nonpolar organic solvent being more than or equal to 40 ℃ and less than or equal to 150 ℃ can achieve satisfactory effect. Further considering the factors of solvent price, availability, stability and the like, at least one of cyclohexane, normal hexane, normal heptane, petroleum ether, gasoline, benzene, toluene and xylene is the best choice.
The feeding amount of the solvent needs to ensure that the reacted organic phase and the strong base aqueous solution phase have enough density difference, so that the organic phase and the strong base aqueous solution phase enter a standing clarification section after continuous reaction in the extraction tower, the emulsification phenomenon is not easy to occur, the layering can be carried out quickly, and the continuous operation in the extraction tower is convenient to realize. The feeding proportion of the non-polar organic solvent and the strong base aqueous solution is important for the design of continuous extraction reaction equipment, and for a multi-stage countercurrent extraction tower, when the flow rates of an extracting agent and a raw material liquid are relatively close, the volumes of clarification layers at the top and the bottom of the tower are relatively close, so that the design and the manufacture of the equipment are facilitated.
The invention has the following advantages:
1. the aldol condensation reaction is carried out in the two-phase fluid, the concentration of benzaldehyde, acetaldehyde and product cinnamaldehyde in a strong alkali aqueous solution can be reduced, and key technical indexes such as the conversion rate, the selectivity, the yield and the like of the reaction are improved;
2. continuous extraction reaction is carried out in the extraction tower, so that the equipment capacity is high;
3. the strong alkali aqueous solution is directly used after part of water is simply distilled, so that the quantity of three wastes is reduced.
Description of the drawings:
FIG. 1 is a diagram of an apparatus for a continuous synthesis method of cinnamaldehyde in the present invention.
Detailed Description
The present invention will be described in detail below by way of examples, but is not limited to these examples, and the parameters of the turret apparatus used in the examples are as follows (see the attached drawings for the implementation apparatus).
Turret equipment parameters
Example 1
Preparing materials:
200g (98.8 percent, 1.8642mol) of benzaldehyde, 220g (40.2 percent, 2.0100mol) of acetaldehyde aqueous solution and 800g of normal hexane are respectively put into two 2000ml raw material configuration bottles (a and b) with thermometers and stirring paddles, the outer wall of the reaction bottle is heated by a water bath kettle, the hot water temperature of the water bath kettle is set to be 50 ℃ for standby.
1500g (mass concentration of 5%) of sodium hydroxide aqueous solution is respectively put into two of 2000ml strong alkaline aqueous solution preparation bottles (a, b and c) with a thermometer and a stirring paddle, the outer wall of the reaction bottle is heated by a water bath kettle, and the hot water temperature of the water bath kettle is set to be 70 ℃ for standby.
Reaction:
and (3) starting hot water of a jacket of the rotating disc tower, and preheating the rotating disc tower by using the hot water at the temperature of 60-70 ℃. The rotating disc tower is started to stir, and the stirring rotating speed is set to be 200 r/min. And (5) starting stirring of the raw material preparation bottle a, and setting the stirring rotating speed to be 800 r/min. And sequentially opening the faucets on the discharge pipes of the raw material configuration bottle a and the strong alkaline aqueous solution configuration bottle a, opening a raw material feed pump and a strong alkaline aqueous solution feed pump, and setting the flow rate of the raw material to be 30ml/min and the flow rate of the strong alkaline aqueous solution to be 30 ml/min. The raw materials and the strong alkali aqueous solution enter a rotating disc tower to carry out countercurrent extraction reaction, and the conversion rate and the selectivity of benzaldehyde are determined by detecting the content of cinnamaldehyde in a product receiving bottle. The conversion rate of the reaction is controlled by controlling the feed flow rate of the raw materials and adjusting the residence time of the raw materials in the rotary disc tower. The selectivity of the reaction is controlled by adjusting the feed ratio of the feedstock to the catalyst. The two-phase mixing effect of the rotating disc tower under the process condition is ensured by adjusting the rotating speed of the rotating disc tower. The bottle a that raw materials were joined in marriage the bottle, strong aqueous alkali prepares the bottle a bottle feeding and finishes switching the b bottle, and a bottle prepares material again when switching into the b bottle, and similar switching is also carried out to the product accepting bottle, so relapse, carries out continuous reaction.
And (3) post-treatment:
the contents of the product receiving bottle were transferred in batches to a separatory funnel, washed 1 time with a 5% aqueous solution of sulfuric acid in an amount 0.1 times the volume of the contents of the separatory funnel, and then washed 3 times with deionized water in an amount 0.1 times the volume of the contents of the separatory funnel each time.
And transferring the washed materials into a 1000ml three-neck flask with a thermometer, a stirring paddle and a recovery condenser in batches after washing is finished, heating the outer wall of the three-neck flask by using hot water at the temperature of 80 ℃, and recovering the solvent under the vacuum degree of more than or equal to 0.08MPa under reduced pressure to obtain a crude product of the cinnamaldehyde after recovery is finished. And rectifying the cinnamaldehyde crude product in a rectifying tower to obtain a cinnamaldehyde finished product with the purity of more than 98%. The cinnamaldehyde yield is about 90-92% calculated by benzaldehyde according to the total amount of the feed.
Catalyst treatment:
when the strong alkali aqueous solution preparation bottle a or b or c is full, switching another strong alkali aqueous solution preparation bottle, placing the full strong alkali aqueous solution preparation bottle in a reduced pressure recovery device, carrying out reduced pressure dehydration at the internal temperature of more than 0.08MPa and less than 60 ℃ under the condition that the dehydration amount is about 10 percent of the total amount, controlling the alkali concentration of the dehydrated alkali aqueous solution to be about 5 percent, and then carrying out strong alkali aqueous solution application. The distilled water is used for extracting acetaldehyde from the n-hexane recovered from the distilled crude product, and the residual wastewater can be used for preparing 5% dilute sulfuric acid.
Example 2
Preparing materials:
200g (98.8 percent, 1.8642mol) of benzaldehyde, 220g (40.2 percent, 2.0100mol) of acetaldehyde aqueous solution and 800g of toluene are respectively put into two 2000ml raw material configuration bottles (a and b) with thermometers and stirring paddles, the outer wall of the reaction bottle is heated by a water bath kettle, the hot water temperature of the water bath kettle is set to be 50 ℃ for standby.
1500g (mass concentration of 5%) of sodium hydroxide aqueous solution is respectively put into two of 2000ml strong alkaline aqueous solution preparation bottles (a, b and c) with a thermometer and a stirring paddle, the outer wall of the reaction bottle is heated by a water bath kettle, and the hot water temperature of the water bath kettle is set to be 70 ℃ for standby.
Reaction:
and (3) starting hot water of a jacket of the rotating disc tower, and preheating the rotating disc tower by using the hot water at the temperature of 60-70 ℃. The rotating disc tower is started to stir, and the stirring speed is set to be 150 r/min. And (5) starting stirring of the raw material preparation bottle a, and setting the stirring rotating speed to be 800 r/min. And sequentially opening the faucets on the discharge pipes of the raw material configuration bottle a and the strong alkaline aqueous solution configuration bottle a, opening a raw material feed pump and a strong alkaline aqueous solution feed pump, and setting the flow rate of the raw material to be 30ml/min and the flow rate of the strong alkaline aqueous solution to be 30 ml/min. The raw materials and the strong alkali aqueous solution enter a rotating disc tower to carry out countercurrent extraction reaction, and the conversion rate and the selectivity of benzaldehyde are determined by detecting the content of cinnamaldehyde in a product receiving bottle. The conversion rate of the reaction is controlled by controlling the feed flow rate of the raw materials and adjusting the residence time of the raw materials in the rotary disc tower. The selectivity of the reaction is controlled by adjusting the feed ratio of the feedstock to the catalyst. The two-phase mixing effect of the rotating disc tower under the process condition is ensured by adjusting the rotating speed of the rotating disc tower. The bottle a that raw materials were joined in marriage the bottle, strong aqueous alkali prepares the bottle a bottle feeding and finishes switching the b bottle, and a bottle prepares material again when switching into the b bottle, and similar switching is also carried out to the product accepting bottle, so relapse, carries out continuous reaction.
And (3) post-treatment:
the contents of the product receiving bottle were transferred in batches to a separatory funnel, washed 1 time with a 5% aqueous solution of sulfuric acid in an amount 0.1 times the volume of the contents of the separatory funnel, and then washed 3 times with deionized water in an amount 0.1 times the volume of the contents of the separatory funnel each time.
And transferring the washed materials into a 1000ml three-neck flask with a thermometer, a stirring paddle and a recovery condenser in batches after washing is finished, heating the outer wall of the three-neck flask by using hot water at the temperature of 80 ℃, and recovering the solvent under the vacuum degree of more than or equal to 0.08MPa under reduced pressure to obtain a crude product of the cinnamaldehyde after recovery is finished. And rectifying the cinnamaldehyde crude product in a rectifying tower to obtain a cinnamaldehyde finished product with the purity of more than 98%. The cinnamaldehyde yield is about 85-88% calculated by benzaldehyde according to the total amount of the feed.
Catalyst treatment:
when the strong alkali aqueous solution preparation bottle a or b or c is full, switching another strong alkali aqueous solution preparation bottle, placing the full strong alkali aqueous solution preparation bottle in a reduced pressure recovery device, carrying out reduced pressure dehydration at the internal temperature of more than 0.08MPa and less than 60 ℃ under the condition that the dehydration amount is about 10 percent of the total amount, controlling the alkali concentration of the dehydrated alkali aqueous solution to be about 5 percent, and then carrying out strong alkali aqueous solution application. The distilled water is used for extracting acetaldehyde from the n-hexane recovered from the distilled crude product, and the residual wastewater can be used for preparing 5% dilute sulfuric acid.
Example 3
Preparing materials:
200g (98.8 percent, 1.8642mol) of benzaldehyde, 220g (40.2 percent, 2.0100mol) of acetaldehyde aqueous solution and 800g of normal hexane are respectively put into two 2000ml raw material configuration bottles (a and b) with thermometers and stirring paddles, the outer wall of the reaction bottle is heated by a water bath kettle, the hot water temperature of the water bath kettle is set to be 50 ℃ for standby.
1500g (mass concentration of 5%) of sodium hydroxide aqueous solution is respectively put into two of 2000ml strong alkaline aqueous solution preparation bottles (a, b and c) with a thermometer and a stirring paddle, the outer wall of the reaction bottle is heated by a water bath kettle, and the hot water temperature of the water bath kettle is set to be 70 ℃ for standby.
Reaction:
and (3) starting hot water of a jacket of the rotating disc tower, and preheating the rotating disc tower by using the hot water at the temperature of 60-70 ℃. The rotating disc tower is started to stir, and the stirring rotating speed is set to be 200 r/min. And (5) starting stirring of the raw material preparation bottle a, and setting the stirring rotating speed to be 800 r/min. And sequentially opening the faucets on the discharge pipes of the raw material configuration bottle a and the strong alkaline aqueous solution configuration bottle a, opening a raw material feed pump and a strong alkaline aqueous solution feed pump, and setting the flow rate of the raw material to be 50ml/min and the flow rate of the strong alkaline aqueous solution to be 50 ml/min. The raw materials and the strong alkali aqueous solution enter a rotating disc tower to carry out countercurrent extraction reaction, and the conversion rate and the selectivity of benzaldehyde are determined by detecting the content of cinnamaldehyde in a product receiving bottle. The conversion rate of the reaction is controlled by controlling the feed flow rate of the raw materials and adjusting the residence time of the raw materials in the rotary disc tower. The selectivity of the reaction is controlled by adjusting the feed ratio of the feedstock to the catalyst. The two-phase mixing effect of the rotating disc tower under the process condition is ensured by adjusting the rotating speed of the rotating disc tower. The bottle a that raw materials were joined in marriage the bottle, strong aqueous alkali prepares the bottle a bottle feeding and finishes switching the b bottle, and a bottle prepares material again when switching into the b bottle, and similar switching is also carried out to the product accepting bottle, so relapse, carries out continuous reaction.
And (3) post-treatment:
the contents of the product receiving bottle were transferred in batches to a separatory funnel, washed 1 time with a 5% aqueous solution of sulfuric acid in an amount 0.1 times the volume of the contents of the separatory funnel, and then washed 3 times with deionized water in an amount 0.1 times the volume of the contents of the separatory funnel each time.
And transferring the washed materials into a 1000ml three-neck flask with a thermometer, a stirring paddle and a recovery condenser in batches after washing is finished, heating the outer wall of the three-neck flask by using hot water at the temperature of 80 ℃, and recovering the solvent under the vacuum degree of more than or equal to 0.08MPa under reduced pressure to obtain a crude product of the cinnamaldehyde after recovery is finished. And rectifying the cinnamaldehyde crude product in a rectifying tower to obtain a cinnamaldehyde finished product with the purity of more than 98%. The cinnamaldehyde yield is about 78-81% calculated by benzaldehyde according to the total amount of the feed.
Catalyst treatment:
when the strong alkali aqueous solution preparation bottle a or b or c is full, switching another strong alkali aqueous solution preparation bottle, placing the full strong alkali aqueous solution preparation bottle in a reduced pressure recovery device, carrying out reduced pressure dehydration at the internal temperature of more than 0.08MPa and less than 60 ℃ under the condition that the dehydration amount is about 10 percent of the total amount, controlling the alkali concentration of the dehydrated alkali aqueous solution to be about 5 percent, and then carrying out strong alkali aqueous solution application. The distilled water is used for extracting acetaldehyde from the n-hexane recovered from the distilled crude product, and the residual wastewater can be used for preparing 5% dilute sulfuric acid.
Claims (2)
1. A continuous synthesis method of cinnamaldehyde is characterized in that a mixture of benzaldehyde, acetaldehyde and a non-polar organic solvent and a strong alkali aqueous solution are subjected to continuous aldol condensation reaction in an extraction tower to synthesize cinnamaldehyde; the mass concentration of strong base in the strong base aqueous solution is 1-20%; the feeding mass ratio of the benzaldehyde to the strong alkali aqueous solution is 1: 0.5-15.0; the nonpolar organic solvent is at least one of cyclohexane, normal hexane, normal heptane, petroleum ether, gasoline, benzene, toluene and xylene; the mass ratio of the benzaldehyde to the non-polar organic solvent is 1: 0.5-15.0.
2. The continuous synthesis method of cinnamaldehyde according to claim 1, wherein the extraction column is a rotating disc column with an internal coil or an external jacket, a reciprocating sieve plate column, or a pulsed packed column.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1104129A1 (en) * | 1982-12-31 | 1984-07-23 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Method of obtaining cinnamic aldehude |
| CN103159602A (en) * | 2013-04-15 | 2013-06-19 | 湖北远成药业有限公司 | After-treatment method of cinnamic aldehyde industrial synthesis |
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2018
- 2018-06-04 CN CN201810561295.8A patent/CN108821957B/en not_active Withdrawn - After Issue
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1104129A1 (en) * | 1982-12-31 | 1984-07-23 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Method of obtaining cinnamic aldehude |
| CN103159602A (en) * | 2013-04-15 | 2013-06-19 | 湖北远成药业有限公司 | After-treatment method of cinnamic aldehyde industrial synthesis |
Non-Patent Citations (1)
| Title |
|---|
| 肉桂醛的制备;刘雪梅;《曲阜师范大学学报》;20050430;第31卷(第2期);96-98 * |
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