CN105924423A - Decoloration reduction method of synthesis heliotropin - Google Patents
Decoloration reduction method of synthesis heliotropin Download PDFInfo
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- CN105924423A CN105924423A CN201610298134.5A CN201610298134A CN105924423A CN 105924423 A CN105924423 A CN 105924423A CN 201610298134 A CN201610298134 A CN 201610298134A CN 105924423 A CN105924423 A CN 105924423A
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- reduction
- piperonal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
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- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention relates to the field of fine chemical engineering, and provides a decoloration reduction method of synthesis heliotropin. The method is characterized in that 100 parts of a heliotropin oxidation crude product is taken, 40-250 parts of water is added, alkali is added and stirred till the PH value is regulated to be 8-11, the temperature is increased to 40-90 DEG C, 0.3-8 parts of an aqueous solution reduction decoloration agent thiourea dioxide is added, a reaction is performed for 1-5 h, the temperature is decreased to 30-50 DEG C after the reaction is finished, standing is performed for 1-3 h for layering, an organic phase on the lower layer is collected, and an aqueous phase on the upper layer is drained into a sewage treatment system; the reduction decoloration agent thiourea dioxide is reacted with a byproduct nitrocompound generated in an oxidation reaction to reduce nitro on benzene rings into nitrate ions, nitro drifts in water in the form of ions, and then reduction decoloration is achieved. The method is low in energy consumption, easy to implement, free of danger, more environmentally friendly and free of damage to the product, the nitrocompound is completely removed finally, and then the product is in a white crystal state without the yellow color.
Description
Technical field
The present invention relates to field of fine chemical, particularly to a kind of decolouring method of reducing synthesizing piperonal.
Background technology
Piperonal, has another name called 3,4-methylenedioxy benzene formaldehyde；Heliotropin；3,4-(methylene-dioxy) benzaldehyde；3,4-methylene two
Methoxybenzaldehyde；3,4-methylene dioxo group benzaldehyde；Piperonal；Heliotropine；It is widely used in perfume, spice, Fructus Pruni pseudocerasi with fragrant
The flavoring agent of grass taste.Can also be used for organic synthesis.
Synthesis piperonal oxidation uses nitric acid oxidation method mostly, because this method reaction gentleness, simple to operate, yield is higher.But meeting
Along with the generation of side reaction, and produce the nitro compound of trace, just the nitro compound of this trace can cause piperonal in
Yellow.And the nitro compound of trace cannot be removed by rectification, recrystallization.So for ensureing that product quality have to
By-product nitro compound is removed, makes nitro be free in water with the form of ion.
Summary of the invention
The purpose of the present invention is exactly to solve above-mentioned technical problem, it is provided that a kind of decolouring method of reducing synthesizing piperonal.
The technical problem of the present invention is mainly addressed by following technical proposals:
A kind of decolouring method of reducing synthesizing piperonal, it is characterised in that take piperonal oxidation crude product 100 parts, add 40～250
The water of part, adds alkali and stirs until pH value is adjusted to 8～11, be warming up to 40～90 DEG C, add the aqueous solution of 0.3～8 part also
Former decolorising agent thiourea dioxide, reacts 1～5 hour, and reaction is cooled to 35～50 DEG C after terminating, stratification 1～3 hours,
Collecting lower floor's organic facies, upper strata aqueous phase enters sewage disposal system, the pair that reduction-decolor agent thiourea dioxide produces with oxidation reaction
Product nitro compound reacts, and the nitro on phenyl ring is reduced into nitrate ion, and nitro is free in water with the form of ion,
Realize reduction-decolor.
Further, described organic facies, at-0.1MPa, collects fraction under the conditions of 140-145 DEG C, after gleanings is decolouring reduction
Piperonal.
Further, described alkali is sodium hydroxide and sodium carbonate.
The invention has the beneficial effects as follows: the present invention uses water-soluble reducing agent thiourea dioxide to be reduction-decolor agent.To Fructus Piperis formoxy-
Change crude product and carry out reduction treatment of decolouring.Because thiourea dioxide selectivity is high, will not react with product piperonal, only can be with
The by-product nitro compound reaction that oxidation reaction produces, is reduced into nitrate ion the nitro on phenyl ring, thus reaches decolouring
The purpose of reduction.Energy consumption of the present invention is low, simple to operate, without dangerous, more environmentally friendly, to product without destroying, finally realizes nitro
Compound is removed completely, makes product shows white lenticular, without yellow.
Detailed description of the invention
Below by embodiment, technical scheme is described in further detail.
Embodiment 1:
A kind of decolouring method of reducing synthesizing piperonal, takes piperonal oxidation crude product 100 parts, adds the water of 100 parts, add alkali
Stirring, until pH value is adjusted to 9, is warming up to 50 DEG C, adds the aqueous solution reduction-decolor agent thiourea dioxide of 2 parts, and reaction 3 is little
Time, reaction is cooled to 45 DEG C after terminating, and stratification 1.5 hours collects lower floor's organic facies, and upper strata aqueous phase enters sewage disposal
System, the by-product nitro compound that reduction-decolor agent thiourea dioxide and oxidation reaction produce reacts, the nitro on phenyl ring also
Former one-tenth nitrate ion, nitro is free in water with the form of ion, it is achieved reduction-decolor.
Described organic facies, at-0.1MPa, collects fraction under the conditions of 140-145 DEG C, gleanings is the piperonal after decolouring reduction.
Described alkali is sodium hydroxide and sodium carbonate.
Embodiment 2:
A kind of decolouring method of reducing synthesizing piperonal, takes piperonal oxidation crude product 100 parts, adds the water of 200 parts, add alkali
Stirring, until pH value is adjusted to 10, is warming up to 40～90 DEG C, adds the aqueous solution reduction-decolor agent thiourea dioxide of 5 parts, instead
Answering 4 hours, reaction is cooled to 40 DEG C after terminating, stratification 2 hours, collects lower floor's organic facies, and upper strata aqueous phase enters sewage
Processing system, the by-product nitro compound that reduction-decolor agent thiourea dioxide and oxidation reaction produce reacts, the nitre on phenyl ring
Base is reduced into nitrate ion, and nitro is free in water with the form of ion, it is achieved reduction-decolor.
Described organic facies, at-0.1MPa, collects fraction under the conditions of 140-145 DEG C, gleanings is the piperonal after decolouring reduction.
Described alkali is sodium carbonate.
Embodiment 3:
A kind of decolouring method of reducing synthesizing piperonal, takes piperonal oxidation crude product 100 parts, adds the water of 250 parts, add alkali
Stirring, until pH value is adjusted to 11, is warming up to 90 DEG C, adds the aqueous solution reduction-decolor agent thiourea dioxide of 8 parts, reacts 5
Hour, reaction is cooled to 50 DEG C after terminating, stratification 3 hours, collects lower floor's organic facies, and upper strata aqueous phase enters sewage disposal
System, the by-product nitro compound that reduction-decolor agent thiourea dioxide and oxidation reaction produce reacts, the nitro on phenyl ring also
Former one-tenth nitrate ion, nitro is free in water with the form of ion, it is achieved reduction-decolor.
Described organic facies, at-0.1MPa, collects fraction under the conditions of 140-145 DEG C, gleanings is the piperonal after decolouring reduction.
Described alkali is sodium hydroxide.
The present embodiment is the embodiment of example of the present invention, for those skilled in the art, the invention discloses
On the basis of application process and principle, it is easy to make various types of improvement or change, it is not limited solely to the present invention above-mentioned specifically
Formula described by embodiment and technique, the most previously described mode is preferred version, and the most restrictive meaning
Justice, every equivalence change made according to the present invention and amendment, all in the scope protection domain of claims of the present invention.
Claims (3)
1. the decolouring method of reducing synthesizing piperonal, it is characterised in that take piperonal oxidation crude product 100 parts, add 40～
The water of 250 parts, adds alkali and stirs until pH value is adjusted to 8～11, be warming up to 40～90 DEG C, add 0.3～8 part water-soluble
Liquid reduction-decolor agent thiourea dioxide, reacts 1～5 hour, and reaction is cooled to 35～50 DEG C after terminating, and stratification 1～3 is little
Time, collect lower floor's organic facies, upper strata aqueous phase enters sewage disposal system, and reduction-decolor agent thiourea dioxide produces with oxidation reaction
By-product nitro compound reaction, the nitro on phenyl ring is reduced into nitrate ion, nitro is free on water with the form of ion
In, it is achieved reduction-decolor.
A kind of decolouring method of reducing synthesizing piperonal the most according to claim 1, it is characterised in that described organic facies exists
Collecting fraction under the conditions of-0.1MPa, 140-145 DEG C, gleanings is the piperonal after decolouring reduction.
A kind of decolouring method of reducing synthesizing piperonal the most according to claim 1, it is characterised in that described alkali is hydrogen-oxygen
Change sodium and sodium carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610298134.5A CN105924423A (en) | 2016-05-06 | 2016-05-06 | Decoloration reduction method of synthesis heliotropin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610298134.5A CN105924423A (en) | 2016-05-06 | 2016-05-06 | Decoloration reduction method of synthesis heliotropin |
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| CN105924423A true CN105924423A (en) | 2016-09-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610298134.5A Pending CN105924423A (en) | 2016-05-06 | 2016-05-06 | Decoloration reduction method of synthesis heliotropin |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080028670A1 (en) * | 2006-08-02 | 2008-02-07 | General Electric Company | Silicone additives for compatalizing organic compounds with wax mixtures |
| CN101525311A (en) * | 2009-04-21 | 2009-09-09 | 福州大学 | Thiourea dioxide derivative-containing sulfonic acid group and preparation method thereof |
| CN102153537A (en) * | 2011-02-22 | 2011-08-17 | 重庆德馨香料植物开发有限公司 | Heliotropin decolorizer and preparation method of heliotropin |
-
2016
- 2016-05-06 CN CN201610298134.5A patent/CN105924423A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080028670A1 (en) * | 2006-08-02 | 2008-02-07 | General Electric Company | Silicone additives for compatalizing organic compounds with wax mixtures |
| CN101525311A (en) * | 2009-04-21 | 2009-09-09 | 福州大学 | Thiourea dioxide derivative-containing sulfonic acid group and preparation method thereof |
| CN102153537A (en) * | 2011-02-22 | 2011-08-17 | 重庆德馨香料植物开发有限公司 | Heliotropin decolorizer and preparation method of heliotropin |
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Application publication date: 20160907 |