CN102964331B - Synthetic method of piperonylenepropanal - Google Patents
Synthetic method of piperonylenepropanal Download PDFInfo
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- CN102964331B CN102964331B CN201210531718.4A CN201210531718A CN102964331B CN 102964331 B CN102964331 B CN 102964331B CN 201210531718 A CN201210531718 A CN 201210531718A CN 102964331 B CN102964331 B CN 102964331B
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Abstract
The invention discloses a preparation method of a chemical spice and particularly relates to a synthetic method of piperonylenepropanal. The synthetic method of the piperonylenepropanal comprises the step of dissolving heliotropin, propionaldehyde and an alkaline reagent into a solvent methanol to react to prepare the piperonylenepropanal. According to the synthetic method of the piperonylenepropanal disclosed by the invention, by-products generated in a reaction of preparing the piperonylenepropanal by using the heliotropin and the propionaldehyde to react can be effectively reduced, so that the reaction conversion rate is improved and the yield is improved; and meanwhile, the synthetic method of the piperonylenepropanal disclosed by the invention can effectively solve the problem that the solvent is difficult to remove in a subsequent purification process, so that the solvent in a mother solution is easier to recycle.
Description
Technical field
The present invention relates to a kind of preparation method of chemical industry spices, be specifically related to a kind of synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Background technology
Piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, chemical name is 2-methyl-3-(3,4-methylenedioxyphenyl) propenal, it is material conventional in a kind of industrial chemicals, the intermediate that Chang Zuowei spices is synthetic, it is still for the synthesis of the medicine intermediate of antitumor drug simultaneously, and its structure is as follows:
The preparation of existing piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil is generally to make by prepare the intermediates that produce preparing piperonyl propionaldehyde process from piperonal.First piperonal carries out claisen-Si Mite condensation reaction with propionic aldehyde, generates intermediates piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oils, and gained piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil makes preparing piperonyl propionaldehyde after by shortening.Above-mentioned reaction process is as follows:
Because piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil is mainly to make by above-mentioned reaction, its existing synthetic method is generally to adopt under the alkaline environment of ethanolic soln, piperonal to be reacted with propionic aldehyde, thereby obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.The by product that the method for existing synthetic piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil produces in actual production is more, causes the yield of product lower; Meanwhile, due to this more difficult removing in subsequent processes of etoh solvent, therefore cause reaction rear mother liquid obtained comparatively difficult in solvent recuperation.
Summary of the invention
In view of this, the invention provides a kind of synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, it can effectively reduce existing piperonal and the propionic aldehyde of utilizing and prepare the by product producing in the reaction of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, thereby improves reaction conversion ratio, improves productive rate; Meanwhile, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention can also solve solvent more difficult problem of removing in subsequent purification process effectively, thereby it is comparatively easy to make from mother liquor, to reclaim solvent.
For solving above technical problem, technical scheme of the present invention is the synthetic method that adopts a kind of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, and the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil includes by making piperonal, propionic aldehyde, alkaline reagents react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol.
Preferably, the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil includes following steps:
A, alkaline reagents is dissolved in to the basic solution that makes methyl alcohol in solvent methanol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, building-up reactions obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Preferably, described methyl alcohol: the weight ratio of piperonal is 0.5-1.5:1.
Preferably, described methyl alcohol: the weight ratio of piperonal is 0.5-1.0:1.
Preferably, described alkaline reagents is inorganic alkaline agents.
Preferably, described inorganic alkaline agents is at least one is selected from potassium hydroxide, sodium hydroxide, salt of wormwood, sodium carbonate or cesium carbonate.
Preferably, described piperonal: propionic aldehyde: the weight ratio of alkaline reagents is 1:0.3-0.6:0.05-0.1.
Preferably, also include oxidation inhibitor in the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, described piperonal, propionic aldehyde, alkaline reagents and oxidation inhibitor react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol.
Preferably, described oxidation inhibitor is BHT.
Preferably, in described C step, the time for adding of propionic aldehyde is 2-10 hour, and synthesising reacting time is 30min-5 hour.
Compared with prior art, its principle is as follows in the present invention:
The synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention includes by making piperonal, propionic aldehyde, alkaline reagents react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol.
In the present invention, adopt the reaction solvent of methyl alcohol as piperonal, propionic aldehyde and alkaline reagents, its reacted reaction solution is by detecting, synthetic method of the present invention is more less as the by product in solvent gained reaction solution than existing use ethanol, thereby the reaction conversion ratio of products obtained therefrom piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil is higher.Existing use ethanol is general all in 80% left and right as the transformation efficiency in solvent gained reaction solution, and reaction conversion ratio after using methyl alcohol as solvent in the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention can be brought up to more than 90%.
Simultaneously, in the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention, the main methyl alcohol that adopts is as reaction solvent, and methyl alcohol is with respect to ethanol, and it is more easily removed in the last handling process of reaction solution, therefore from reaction solution, reclaim solvent methanol just more easy, the processing of reaction solution is comparatively simple.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil to include following steps:
A, alkaline reagents is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, building-up reactions obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
The present invention preferably adopts the step of above-mentioned synthetic piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil can further reduce the generation of by product, thereby improves reaction conversion ratio.The synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention is except adopting above-mentioned preparation process, can also adopt and first piperonal, alkaline reagents are all dissolved in to solvent methanol and make after mixed solution, again propionic aldehyde is slowly added to the mode in gained mixed solution or piperonal is dissolved in methyl alcohol, be added dropwise to the reactive mode of the basic solution of methyl alcohol with propionic aldehyde simultaneously, but adopt after preferred mode of the present invention, reaction conversion ratio is higher.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts described methyl alcohol: the weight ratio of piperonal is 0.5-1.5:1.The present invention adopts methyl alcohol as solvent, if its consumption is less than methyl alcohol: the ratio that the weight ratio of piperonal is 0.5:1, due to quantity of solvent very little, reaction carry out with regard to more difficult, thereby yield is lower; If the consumption of the present invention's methyl alcohol is higher than methyl alcohol: when ratio that the weight ratio of piperonal is 1.5:1,, because quantity of solvent is too many, reaction solution concentration is lower, can cause the reaction times long, and because methanol usage too much also can cause production cost higher.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts described methyl alcohol: the weight ratio of piperonal is 0.5-1.0:1.The present invention preferably adopts aforesaid way can further simplify the step of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil synthesis reaction solution of the present invention in aftertreatment.
Existing use ethanol is as the reaction solvent of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, because side reaction in its reaction system is more, therefore, and the existing ethanol that generally can add more amount with ethanol as solvent, thus the generation of by product reduced; Just can carry out the crystallisation step of product but the increase of ethanol just makes subsequent reactions liquid need to first carry out solvent distillation, therefore cause existing preparation method comparatively complicated.
After the present invention adopts methyl alcohol as reaction solvent, in the reaction system of methyl alcohol side reaction less, thereby the consumption of solvent can suitably reduce; Especially when adopting methyl alcohol: after the weight ratio of piperonal is 0.5-1.0:1, gained reaction solution does not need can carry out through the step of predistillation solvent methanol the crystallisation step of product, thereby more effectively make the preparation process of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil be simplified, greatly reduce artificial and power cost; Meanwhile, adopt the post-reacted transformation efficiency of aforesaid way still more than 90%.
Further, preferably to adopt described alkaline reagents be inorganic alkaline agents to the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention.Alkaline reagents of the present invention can comprise organic alkaline reagents as diisopropylethylamine, triethylamine, LDA, sodium methylate, sodium ethylate, sodium-acetate etc., can also include inorganic alkaline agents as hydrated barta, sodium sulphite, strontium hydroxide, lithium hydroxide, sodium hydroxide, potassium hydroxide, salt of wormwood, sodium carbonate, cesium carbonate, KF/Al
2o
3, magnesium oxide, Vanadium Pentoxide in FLAKES, NaH etc.Inorganic alkaline agents is compared organic basic reagent and is more easily removed in the process of reaction solution aftertreatment, thereby can further simplify the last handling process of building-up reactions of the present invention.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts described inorganic alkaline agents at least one is selected from potassium hydroxide, sodium hydroxide, salt of wormwood, sodium carbonate or cesium carbonate.It is inorganic alkaline agents that the present invention preferably adopts alkaline reagents, and more preferably inorganic alkaline agents is at least one is selected from potassium hydroxide, sodium hydroxide, salt of wormwood, sodium carbonate or cesium carbonate.No matter above-mentioned several inorganic alkaline agents that the present invention preferably adopts are on its alkaline degree of strength or all more excellent than remaining inorganic alkaline agents in the complexity of the aftertreatment of this reaction own.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts described piperonal: propionic aldehyde: the weight ratio of alkaline reagents is 1:0.3-0.6:0.05-0.1.In the time that alkaline reagents of the present invention is preferably at least one and is selected from potassium hydroxide, sodium hydroxide, salt of wormwood, sodium carbonate or cesium carbonate, described piperonal: propionic aldehyde: the weight ratio of alkaline reagents is 1:0.3-0.6:0.05-0.1.The present invention preferably adopts the part by weight between above-mentioned three kinds of materials can on the basis of not wasting reaction mass, further improve the transformation efficiency of the rear gained piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of reaction.
Further, the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts in the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil and also includes oxidation inhibitor, and described piperonal, propionic aldehyde, alkaline reagents and oxidation inhibitor react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol.The present invention preferably adopts to be increased more than the mode of oxidation inhibitor can improve the transformation efficiency to 92% of reaction better.Preferred, it is BHT that the present invention preferably adopts described oxidation inhibitor.BHT, chemical name is 2,6 di tert butyl 4 methyl phenol.
Further, it is 4-8 hour that the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention preferably adopts the time for adding of propionic aldehyde in described C step, and synthesising reacting time is 30min-2 hour.Because piperonal in the present invention and reacting of propionic aldehyde are claisen-Si Mite condensation reaction type; Therefore, in synthetic method of the present invention, the speed that adds of propionic aldehyde can have a certain impact to the transformation efficiency of this building-up reactions.It is 4-8 hour that the present invention preferably adopts the time for adding of above-mentioned control propionic aldehyde, and after synthesising reacting time is 30min-2 hour, the concrete real time adopting can be selected according to the consumption of reaction mass.The present invention preferably adopts aforesaid way can further improve the building-up reactions transformation efficiency of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil of the present invention.
Embodiment
In order to make those skilled in the art understand better technical scheme of the present invention, below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: potassium hydroxide is 0.5:1:0.3:0.05.
A, potassium hydroxide is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 2 hours; Building-up reactions 30min obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 1 is 95%.
This embodiment 1 in last handling process reaction solution through in weak acid and after can carry out crystallisation step without predistillation methyl alcohol, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 90.2%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Embodiment 2
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: sodium hydroxide is 1.5:1:0.6:0.1.
A, sodium hydroxide is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 2 hours, and building-up reactions 30min obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 2 is 95.6%.
This embodiment 2 in last handling process reaction solution after weak acid neutralization through predistillation methyl alcohol and crystallisation step, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 90.5%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Embodiment 3
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: salt of wormwood is 1.0:1:0.3:0.1.
A, salt of wormwood is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 4 hours, building-up reactions 2 hours piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 3 is 95.1%.
This embodiment 3 in last handling process reaction solution through in weak acid and after can carry out crystallisation step without predistillation methyl alcohol, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 90.4%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Embodiment 4
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: cesium carbonate is 1.5:1:0.6:0.05.
A, cesium carbonate is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 10 hours, building-up reactions 2 hours piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 4 is 95.9%.
This embodiment 4 in last handling process reaction solution after weak acid neutralization through predistillation methyl alcohol and crystallisation step, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 91.3%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Embodiment 5
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: sodium carbonate is 0.8:1:0.6:0.1.
A, sodium carbonate is dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 6 hours, building-up reactions 5 hours piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 5 is 95.3%.
This embodiment 5 in last handling process reaction solution through in weak acid and after can carry out crystallisation step without predistillation methyl alcohol, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 90.8%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Embodiment 6
Take each material according to following weight proportioning:
Methyl alcohol: piperonal: propionic aldehyde: potassium hydroxide is 1.0:1:0.3:0.1.
A, potassium hydroxide and antioxidant BHT are dissolved in to the basic solution that makes methyl alcohol in reaction solvent methyl alcohol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, temperature of reaction is 15-45 DEG C, and time for adding is 6 hours, building-up reactions 5 hours piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil.
Gained reaction solution after reaction is sampled and carries out LC/MS detection, and the reaction conversion ratio that draws this embodiment 6 is 97.0%.
This embodiment 6 in last handling process reaction solution through in weak acid and after can carry out crystallisation step without predistillation methyl alcohol, obtain product piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, product yield is 92.3%.After crystallization, mother liquor reclaims solvent methanol and reaction raw materials.
Below be only the preferred embodiment of the present invention, it should be pointed out that above-mentioned preferred implementation should not be considered as limitation of the present invention, protection scope of the present invention should be as the criterion with claim limited range.For those skilled in the art, without departing from the spirit and scope of the present invention, can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (3)
1. the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, is characterized in that: the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil includes by making piperonal, propionic aldehyde, alkaline reagents react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol; Described synthetic method includes following steps:
A, alkaline reagents is dissolved in to the basic solution that makes methyl alcohol in solvent methanol;
B, the basic solution that piperonal is dissolved in to methyl alcohol in A step make mixed solution;
C, propionic aldehyde is added dropwise in B in prepared mixed solution, building-up reactions obtains piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil;
Wherein, alkaline reagents is at least one is selected from potassium hydroxide, sodium hydroxide, salt of wormwood, sodium carbonate or cesium carbonate; Described methyl alcohol: the weight ratio of piperonal is 0.5-1.0:1; Described piperonal: propionic aldehyde: the weight ratio of alkaline reagents is 1:0.3-0.6:0.05-0.1; In C step, the time for adding of propionic aldehyde is 2-10 hour, and synthesising reacting time is 30min-5 hour.
2. the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil according to claim 1, it is characterized in that: in the synthetic method of described piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil, also include oxidation inhibitor, described piperonal, propionic aldehyde, alkaline reagents and oxidation inhibitor react and prepare piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil in solvent methanol.
3. the synthetic method of piperonylenepropanalfrom from Cinnamomum Petrophilum Leaves Oil according to claim 2, is characterized in that: described oxidation inhibitor is BHT.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1365962A (en) * | 2001-01-18 | 2002-08-28 | 杭州格林香料化学有限公司 | Process for preparing piperonyl propionaldehyde |
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| JP2004269376A (en) * | 2003-03-06 | 2004-09-30 | Ube Ind Ltd | Method for producing 1-formyl-3-(3,4-methylenedioxyphenyl)propene derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1365962A (en) * | 2001-01-18 | 2002-08-28 | 杭州格林香料化学有限公司 | Process for preparing piperonyl propionaldehyde |
Non-Patent Citations (5)
| Title |
|---|
| Iuliana Cota et al..The DBU-H2O complex as a new catalyst for aldol condensation reactions.《Catalysis Communications》.2008,第9卷2090-2094. * |
| JP特開2004-269376A 2004.09.30 * |
| Sònia Abelló et al..Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions.《C h e m . C o m m u n .》.2004,1096-1097. * |
| Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions;Sònia Abelló et al.;《C h e m . C o m m u n .》;20040401;1096-1097 * |
| The DBU-H2O complex as a new catalyst for aldol condensation reactions;Iuliana Cota et al.;《Catalysis Communications》;20080408;第9卷;2090-2094 * |
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