CN108821957A - A kind of method for continuously synthesizing of cinnamic acid - Google Patents
A kind of method for continuously synthesizing of cinnamic acid Download PDFInfo
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- CN108821957A CN108821957A CN201810561295.8A CN201810561295A CN108821957A CN 108821957 A CN108821957 A CN 108821957A CN 201810561295 A CN201810561295 A CN 201810561295A CN 108821957 A CN108821957 A CN 108821957A
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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
- C07C45/61—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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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Abstract
The invention discloses a kind of method for continuously synthesizing of cinnamic acid, and benzaldehyde, acetaldehyde are mixed with non-polar organic solvent, and using strong alkali aqueous solution as catalyst, the mode in extraction tower by countercurrent reaction extraction obtains cinnamic acid.The present invention improves conversion ratio, selectivity and the yield of aldol reaction by the way that non-polar organic solvent is added in aldol reaction, and makes aldol reaction that continuous production may be implemented in extraction equipment.It can directly be applied after the strong alkali aqueous solution dehydration of end of reaction, achieve the purpose that reduce discharge of wastewater.
Description
Technical field
The present invention relates to Fine Organic Chemicals to synthesize field, and in particular to a kind of conjunction of fine-chemical intermediate cinnamic acid
At.
Background technique
Cinnamic acid (3- phenyl -2- methacrylaldehyde) English name：Cinnamaldehyde is in one kind important chemical industry and medicine
Mesosome, application range are extremely extensive.In organic synthesis field for synthesizing a- bromo cinnamaldehyde, cinnamyl alcohol, cinnamic acid, cortex cinnamomi
A series of products such as nitrile.It is used as in flavors and fragrances industry and is used with perfume material, make main fragrance aroma more faint scent.Because of its boiling point score
Other similar organic matters of minor structure are high, thus are commonly used for fixastive.In fields such as food, feed, preservatives, cinnamic acid also has
It is widely applied.The chemosynthesis reaction of cinnamic acid is as follows：
Common synthetic method is to put into benzaldehyde, acetaldehyde, highly basic, solvent (alcohols) in reaction kettle, reacting kettle jacketing
It is passed through hot water to be heated, acetaldehyde and benzaldehyde occur aldol reaction and form cinnamic acid under the catalytic action of highly basic.
Extractant is added in end of reaction, successively uses diluted acid water, deionized water washing reaction liquid.Reaction solution after washing
Cinnamic acid crude product is obtained after recycling design, the cinnamic acid that crude product rectifying in rectifying column is conformed to quality requirements.
It is urged in common synthetic method using catalyst of the highly basic as aldol reaction, highly basic such as solid NaOH, KOH
The principle of change is that acetaldehyde is made to ionize out α-carbanion in the presence of alkali, and parent occurs for the carbonyl of the α-carbanion and benzaldehyde
Then core addition reaction occurs elimination reaction and forms cinnamic acid.The generation of the strong easy initiation reaction of the alkalinity of catalyst, but it is too strong
Alkalinity can cause excessive α-carbanion, accelerate the aldol condensation side reaction of acetaldehyde itself, too strong alkalinity can also promote
Disproportionated reaction occurs into benzaldehyde itself and forms benzyl alcohol, benzoic acid and some other side reaction.
Main side reaction is as described below：
1, the aldol condensation side reaction of acetaldehyde itself：
2, the disproportionated reaction of benzaldehyde：
3, other more complicated chemical reactions：
The condensation reaction of benzaldehyde and polymolecular acetaldehyde condensation object is also occurred that in addition to above-mentioned 1,2 main side reaction, more
The self-condensation side reaction of multiple acetaldehyde, polymerization side reactions of olefine aldehydr etc..
So being the mixing of cinnamic acid and a series of by-products as described above obtained in the synthetic reaction of cinnamic acid
Object.Patent CN105152891A improves using solid super base as catalyst using fixation above-mentioned conventional synthesis process
Bed reactive mode synthesizes cinnamic acid.The process program can be omitted diluted acid water washing technique compared with common process, reduce
The generation of waste water has certain environment-friendly advantage.But industrialization zoom comparison of the fixed bed reactors in gas-solid phase reaction is held
Easily, and liquid and solid phase reaction because of back mixing the reason of, be difficult to realize industrialization amplification.Patent CN1260194C is used in no base catalysis
The aldol contracting of (200-300 DEG C, 10-20MPa) progress cinnamic acid synthesis under agent, organic solvent-free, large scale water, near critical state
Reaction is closed, which reduces the concentration that acetaldehyde forms carbanion, and selectivity is promoted.Because there is no basic catalyst
Catalytic action conversion ratio it is extremely low, yield highest only has 16.6%, it is difficult to realize industrialized production.
In short, there are following defects for above-mentioned conventional cinnamic acid synthetic method：
1, the conversion ratio of main material benzaldehyde is low, poor selectivity；
2, by-product is more, and post-processing is difficult；
3, wastewater flow rate is big, and cost for wastewater treatment is high；
4, interval metaplasia produces, and utilization rate of equipment and installations is low, and production capacity is low.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the problems of the above-mentioned prior art, it is anti-to improve cinnamic acid synthesis
The conversion ratio answered, selectivity improve cinnamic acid quality, reduce three wastes quantity, and the production of unit equipment is improved using serialization technology
Energy.
In order to solve the above technical problems, the present invention adopts the following technical scheme that：
A kind of method for continuously synthesizing of cinnamic acid, includes the following steps：Benzaldehyde, acetaldehyde and nonpolarity have in extraction tower
The mixture of solvent synthesizes cinnamic acid by continuous aldol reaction with strong alkali aqueous solution.
Preferably, the highly basic mass concentration of the strong alkali aqueous solution is 1~20%.
Preferably, the mass ratio that feeds intake of the benzaldehyde and strong alkali aqueous solution is 1:0.5~15.0.
Preferably, density≤0.95g/cm of the non-polar organic solvent3。
It is further preferred that the boiling spread of the non-polar organic solvent is：The boiling of 40 DEG C≤non-polar organic solvent
Point≤150 DEG C.
Still further preferably, the non-polar organic solvent includes hexamethylene, n-hexane, normal heptane, petroleum ether, vapour
At least one of oil, benzene,toluene,xylene.
Preferably, the mass ratio that feeds intake of the benzaldehyde and non-polar organic solvent is 1:0.5~15.0.
Preferably, the extraction tower includes that there is inner coil pipe or outer jacketed rotating disc column, reciprocating plate column, pulse to fill out
Expect tower.
Cardinal principle of the invention：
Firstly, the present invention improves the conversion ratio and selectivity of reaction by the way of two phase reaction, by main material benzaldehyde,
Acetaldehyde, which is dissolved into non-polar organic solvent, carries out two phase reaction with strong alkali aqueous solution, and this mode avoids benzaldehyde for a long time
Strong alkali aqueous solution is contacted, the side reaction that benzaldehyde is contacted with highly basic is reduced.Raw material acetaldehyde has certain in organic phase, water phase
Solvability reduces it in the concentration of water phase by way of non-polar organic solvent is added, reduces acetaldehyde and highly basic water
The time of contact of solution reduces a series of side reactions that acetaldehyde itself occurs under highly basic effect；Secondly, anti-that can control
It answers in the extraction tower of temperature, two-phase mixtures speed and carries out the aldol reaction.Make to dissolve benzene using external energy in extraction section
Formaldehyde, acetaldehyde non-polar organic solvent phase be mutually sufficiently mixed and controlled with strong alkali aqueous solution and carried out near optimum temperature
Reaction is separated using the density contrast of two-phase standing settling section, realizes continuous reaction, improve the production capacity of equipment；
Finally, strong alkali aqueous solution realization is continuously applied, reduce discharge of wastewater.A small amount of acetaldehyde in strong alkali aqueous solution can repeat benefit
With reducing the loss of acetaldehyde.
Using 1~20% strong alkali aqueous solution as catalysts, the too high side reaction of the concentration of highly basic can increase the present invention
It is more；Concentration too low reaction speed is slow, it is difficult to continuous operation is realized in extraction tower.Comprehensively consider selectivity, conversion ratio, receipts
Rate, production capacity can obtain ideal reaction effect using 1~20% catalyst concn.
The effect of reaction dissolvent is mainly to provide the medium of a two phase reaction, to have enough for benzaldehyde, acetaldehyde
Big solubility reduces the concentration of benzaldehyde, acetaldehyde in strong alkali aqueous solution.The density of solvent is smaller than water, is conducive to react
Finish the layering of organic phase and water phase.The present invention uses density≤0.95g/cm3Non-polar organic solvent can be good at and
Strong alkali aqueous solution layering, and viscosity is small, chemical property is stable, loss is small.Need further exist for considering is exactly the boiling point of solvent
Suitable, the too low loss in reaction and separation process of boiling point is big, the rate of recovery is low；Boiling point is too high, in the solvent recovery of post-processing
It will cause a small amount of product in the process and bring solvent system, processing trouble into, the present invention uses：40 DEG C≤non-polar organic solvent boiling point
The solvent of≤150 DEG C of boiling spreads can achieve the effect that satisfied.Further consider price, the ready availability, stability of solvent
Etc. at least one of factors hexamethylene, n-hexane, normal heptane, petroleum ether, gasoline, benzene,toluene,xylene be optimal choosing
It selects.
The inventory of solvent needs to guarantee that the organic phase of end of reaction mutually has enough density contrasts with strong alkali aqueous solution, this
Sample, which carries out entering after successive reaction in extraction tower, stands settling section, it is not easy to emulsion occurs, can fast hierarchical, be convenient for
Continuous operation is realized in extraction tower.Non-polar organic solvent, which reacts continuous extraction with the ingredient proportion of strong alkali aqueous solution, to be set
Standby design is most important, for multi-stage counter current extraction tower, when the flow of extractant and material liquid relatively when tower top
Relatively with the clear layer volume of tower bottom, be conducive to the design and manufacture of equipment in this way.
The invention has the advantages that：
1, aldol reaction is carried out in two-phase fluid, can reduce benzaldehyde, acetaldehyde, product cinnamic acid in highly basic water
Concentration in solution improves the key technical index such as conversion ratio, selectivity, the yield of reaction；
2, continuous extraction reaction is carried out in extraction tower, equipment capacity is big；
3, strong alkali aqueous solution reduces three wastes quantity by directly applying after the water of simple distillation part.
Detailed description of the invention：
Fig. 1 is a kind of device figure of the method for continuously synthesizing of cinnamic acid of the present invention.
Specific embodiment
The present invention is specifically described below by embodiment, the present invention but be not limited to these embodiments, embodiment is adopted
Rotating disc column device parameter is (implementing device is shown in attached drawing) as described below.
Rotating disc column device parameter
Embodiment 1
Stock：
Benzaldehyde 200g is respectively put into two 2000ml raw material configurations bottle (a, b) with thermometer, agitating paddle
(98.8%, 1.8642mol), acetaldehyde solution 220g (40.2%, 2.0100mol), n-hexane 800g, reaction flask outer wall water
Bath heating, sets water-bath hot water temperature as 50 DEG C, spare.
The two of them in bottle (a, b, c) are prepared in three 2000ml strong alkali aqueous solutions with thermometer, agitating paddle respectively to throw
Enter sodium hydrate aqueous solution 1500g (mass concentration 5%), reaction flask outer wall is heated with water-bath, sets water-bath hot water temperature
It is 70 DEG C, it is spare.
Reaction：
Rotating disc column collet hot water is opened, rotating disc column is preheated with 60~70 DEG C of hot water.Rotating disc column stirring is opened, setting is stirred
Mixing revolving speed is 200r/min.The stirring of Kaiyuan material configuration bottle a, sets speed of agitator 800r/min.It successively opens raw material and configures bottle
A, the cock on the discharge nozzle of strong alkali aqueous solution configuration bottle a, Kaiyuan expect feed pump, strong alkali aqueous solution feed pump, set raw material flow
Amount is 30ml/min, and strong alkali aqueous solution flow is 30ml/min.Raw material and strong alkali aqueous solution enter rotating disc column and carry out counter-current extraction
Reaction, the conversion ratio and selectivity of benzaldehyde are determined by cinnamic aldehyde content in testing product receiving flask.Pass through control raw material
Feed rate adjusts the conversion ratio of residence time control reaction of the raw material in rotating disc column.By adjusting raw material and catalyst into
The selectivity of material ratio control reaction.Ensure the two-phase mixtures effect of process conditions lower rotary table tower by adjusting rotating disc column revolving speed.
The a bottle charging that raw material prepares bottle, strong alkali aqueous solution preparation bottle finishes b bottles of switching, stocks up again for a bottles when being switched to b bottles, product
Receiving flask also carries out similar switching, repeatedly, carries out successive reaction.
Post-processing：
Material in product receiving flask is transferred in separatory funnel in batches, with 0.1 times of volume of material in separatory funnel
5% aqueous sulfuric acid wash 1 time, then washed 3 times with 0.1 times of volume of material in separatory funnel of deionized water every time.
Washing finishes, and the material washed is in batches transferred to 1000ml with thermometer, agitating paddle, recycling condenser
In three-necked flask, solvent is recovered under reduced pressure, and recycling finishes in 80 DEG C of hot water heatings of there-necked flask outer wall at vacuum degree >=0.08MPa
Obtain cinnamic acid crude product.The rectifying in rectifying column of cinnamic acid crude product obtains 98% or more cinnamic acid finished product.According to total feed
The cinnamic acid yield about 90~92% calculated with benzaldehyde.
Catalyst treatment：
When strong alkali aqueous solution, which prepares bottle a or b or c, to be filled, switches another strong alkali aqueous solution and prepare bottle, it is strong by what is filled
Aqueous alkali prepares bottled in device is recovered under reduced pressure, less than 60 DEG C decompression dehydrations of interior temperature more than vacuum degree 0.08MPa, dehydration
Amount is 10% or so of total amount, and after control dehydration then the alkali concentration of aqueous alkali carries out strong alkali aqueous solution set 5% or so
With.The n-hexane extraction acetaldehyde therein that the water distilled out is recycled out with distillation crude product, the waste water of raffinate can prepare 5% dilute sulphur
Acid uses.
Embodiment 2
Stock：
Benzaldehyde 200g is respectively put into two 2000ml raw material configurations bottle (a, b) with thermometer, agitating paddle
(98.8%, 1.8642mol), acetaldehyde solution 220g (40.2%, 2.0100mol), toluene 800g, reaction flask outer wall water-bath
Pot heating, sets water-bath hot water temperature as 50 DEG C, spare.
The two of them in bottle (a, b, c) are prepared in three 2000ml strong alkali aqueous solutions with thermometer, agitating paddle respectively to throw
Enter sodium hydrate aqueous solution 1500g (mass concentration 5%), reaction flask outer wall is heated with water-bath, sets water-bath hot water temperature
It is 70 DEG C, it is spare.
Reaction：
Rotating disc column collet hot water is opened, rotating disc column is preheated with 60~70 DEG C of hot water.Rotating disc column stirring is opened, setting is stirred
Mixing revolving speed is 150r/min.The stirring of Kaiyuan material configuration bottle a, sets speed of agitator 800r/min.It successively opens raw material and configures bottle
A, the cock on the discharge nozzle of strong alkali aqueous solution configuration bottle a, Kaiyuan expect feed pump, strong alkali aqueous solution feed pump, set raw material flow
Amount is 30ml/min, and strong alkali aqueous solution flow is 30ml/min.Raw material and strong alkali aqueous solution enter rotating disc column and carry out counter-current extraction
Reaction, the conversion ratio and selectivity of benzaldehyde are determined by cinnamic aldehyde content in testing product receiving flask.Pass through control raw material
Feed rate adjusts the conversion ratio of residence time control reaction of the raw material in rotating disc column.By adjusting raw material and catalyst into
The selectivity of material ratio control reaction.Ensure the two-phase mixtures effect of process conditions lower rotary table tower by adjusting rotating disc column revolving speed.
The a bottle charging that raw material prepares bottle, strong alkali aqueous solution preparation bottle finishes b bottles of switching, stocks up again for a bottles when being switched to b bottles, product
Receiving flask also carries out similar switching, repeatedly, carries out successive reaction.
Post-processing：
Material in product receiving flask is transferred in separatory funnel in batches, with 0.1 times of volume of material in separatory funnel
5% aqueous sulfuric acid wash 1 time, then washed 3 times with 0.1 times of volume of material in separatory funnel of deionized water every time.
Washing finishes, and the material washed is in batches transferred to 1000ml with thermometer, agitating paddle, recycling condenser
In three-necked flask, solvent is recovered under reduced pressure, and recycling finishes in 80 DEG C of hot water heatings of there-necked flask outer wall at vacuum degree >=0.08MPa
Obtain cinnamic acid crude product.The rectifying in rectifying column of cinnamic acid crude product obtains 98% or more cinnamic acid finished product.According to total feed
The cinnamic acid yield about 85~88% calculated with benzaldehyde.
Catalyst treatment：
When strong alkali aqueous solution, which prepares bottle a or b or c, to be filled, switches another strong alkali aqueous solution and prepare bottle, it is strong by what is filled
Aqueous alkali prepares bottled in device is recovered under reduced pressure, less than 60 DEG C decompression dehydrations of interior temperature more than vacuum degree 0.08MPa, dehydration
Amount is 10% or so of total amount, and after control dehydration then the alkali concentration of aqueous alkali carries out strong alkali aqueous solution set 5% or so
With.The n-hexane extraction acetaldehyde therein that the water distilled out is recycled out with distillation crude product, the waste water of raffinate can prepare 5% dilute sulphur
Acid uses.
Embodiment 3
Stock：
Benzaldehyde 200g is respectively put into two 2000ml raw material configurations bottle (a, b) with thermometer, agitating paddle
(98.8%, 1.8642mol), acetaldehyde solution 220g (40.2%, 2.0100mol), n-hexane 800g, reaction flask outer wall water
Bath heating, sets water-bath hot water temperature as 50 DEG C, spare.
The two of them in bottle (a, b, c) are prepared in three 2000ml strong alkali aqueous solutions with thermometer, agitating paddle respectively to throw
Enter sodium hydrate aqueous solution 1500g (mass concentration 5%), reaction flask outer wall is heated with water-bath, sets water-bath hot water temperature
It is 70 DEG C, it is spare.
Reaction：
Rotating disc column collet hot water is opened, rotating disc column is preheated with 60~70 DEG C of hot water.Rotating disc column stirring is opened, setting is stirred
Mixing revolving speed is 200r/min.The stirring of Kaiyuan material configuration bottle a, sets speed of agitator 800r/min.It successively opens raw material and configures bottle
A, the cock on the discharge nozzle of strong alkali aqueous solution configuration bottle a, Kaiyuan expect feed pump, strong alkali aqueous solution feed pump, set raw material flow
Amount is 50ml/min, and strong alkali aqueous solution flow is 50ml/min.Raw material and strong alkali aqueous solution enter rotating disc column and carry out counter-current extraction
Reaction, the conversion ratio and selectivity of benzaldehyde are determined by cinnamic aldehyde content in testing product receiving flask.Pass through control raw material
Feed rate adjusts the conversion ratio of residence time control reaction of the raw material in rotating disc column.By adjusting raw material and catalyst into
The selectivity of material ratio control reaction.Ensure the two-phase mixtures effect of process conditions lower rotary table tower by adjusting rotating disc column revolving speed.
The a bottle charging that raw material prepares bottle, strong alkali aqueous solution preparation bottle finishes b bottles of switching, stocks up again for a bottles when being switched to b bottles, product
Receiving flask also carries out similar switching, repeatedly, carries out successive reaction.
Post-processing：
Material in product receiving bottle is transferred in separatory funnel in batches, with 0.1 times of volume of material in separatory funnel
5% aqueous sulfuric acid wash 1 time, then washed 3 times with 0.1 times of volume of material in separatory funnel of deionized water every time.
Washing finishes, and the material washed is in batches transferred to 1000ml with thermometer, agitating paddle, recycling condenser
In three-necked flask, solvent is recovered under reduced pressure, and recycling finishes in 80 DEG C of hot water heatings of there-necked flask outer wall at vacuum degree >=0.08MPa
Obtain cinnamic acid crude product.The rectifying in rectifying column of cinnamic acid crude product obtains 98% or more cinnamic acid finished product.According to total feed
The cinnamic acid yield about 78~81% calculated with benzaldehyde.
Catalyst treatment：
When strong alkali aqueous solution, which prepares bottle a or b or c, to be filled, switches another strong alkali aqueous solution and prepare bottle, it is strong by what is filled
Aqueous alkali prepares bottled in device is recovered under reduced pressure, less than 60 DEG C decompression dehydrations of interior temperature more than vacuum degree 0.08MPa, dehydration
Amount is 10% or so of total amount, and after control dehydration then the alkali concentration of aqueous alkali carries out strong alkali aqueous solution set 5% or so
With.The n-hexane extraction acetaldehyde therein that the water distilled out is recycled out with distillation crude product, the waste water of raffinate can prepare 5% dilute sulphur
Acid uses.
Claims (8)
1. a kind of method for continuously synthesizing of cinnamic acid, which is characterized in that benzaldehyde, acetaldehyde and nonpolarity are organic molten in extraction tower
The mixture of agent synthesizes cinnamic acid by continuous aldol reaction with strong alkali aqueous solution.
2. a kind of method for continuously synthesizing of cinnamic acid according to claim 1, which is characterized in that the strong alkali aqueous solution
Highly basic mass concentration be 1~20%.
3. a kind of method for continuously synthesizing of cinnamic acid according to claim 1 or 2, which is characterized in that benzaldehyde and highly basic
The mass ratio that feeds intake of aqueous solution is 1:0.5~15.0.
4. a kind of method for continuously synthesizing of cinnamic acid according to claim 1, which is characterized in that non-polar organic solvent
Density≤0.95g/cm3。
5. a kind of method for continuously synthesizing of cinnamic acid according to claim 1 or 4, which is characterized in that nonpolarity is organic molten
The boiling spread of agent is：40 DEG C≤non-polar organic solvent boiling point≤150 DEG C.
6. a kind of method for continuously synthesizing of cinnamic acid according to claim 1 or 5, which is characterized in that the nonpolarity
Organic solvent preferably includes at least one of hexamethylene, n-hexane, normal heptane, petroleum ether, gasoline, benzene,toluene,xylene.
7. a kind of method for continuously synthesizing of cinnamic acid according to claim 1, which is characterized in that benzaldehyde has with nonpolarity
The mass ratio that feeds intake of solvent is 1:0.5~15.0.
8. a kind of method for continuously synthesizing of cinnamic acid according to claim 1, which is characterized in that the extraction tower includes
With inner coil pipe or outer jacketed rotating disc column, reciprocating plate column, pulsed packed tower.
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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 |
-
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 (2)
| Title |
|---|
| 刘雪梅: "肉桂醛的制备", 《曲阜师范大学学报》 * |
| 金真等: "《应用化学综合实验》", 30 September 2017, 中山大学出版社 * |
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Granted publication date: 20210723 Effective date of abandoning: 20210916 |