CN104072360A - Synthetic method for natural cinnamic acid - Google Patents
Synthetic method for natural cinnamic acid Download PDFInfo
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- CN104072360A CN104072360A CN201310097036.1A CN201310097036A CN104072360A CN 104072360 A CN104072360 A CN 104072360A CN 201310097036 A CN201310097036 A CN 201310097036A CN 104072360 A CN104072360 A CN 104072360A
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- natural
- styracin
- synthesis
- cinnamic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
Abstract
The invention discloses a synthetic method for natural cinnamic acid. The method comprises the following steps: (1) selection of raw materials: a step of selecting cinnamaldehyde considerably and separately separated from cassia oil as a raw material and dissolving cinnamaldehyde in a sodium dihydrogen phosphate buffer solution; and (2) synthesis of cinnamic acid: a step of adding a hydrogen peroxide reagent and a phase-transfer catalyst in the cinnamaldehyde solution prepared in the step (1), then adding glacial acetic acid drop by drop to adjust a pH value to 4, then slowly adding a cooled aqueous chlorite solution drop by drop with stirring at room temperature, carrying out stirring for 4 to 5 h after completion of addition, then carrying out cooling to less than -10 DEG C until a reaction is completed, then carrying out pumping filtration, carrying out recrystallization with ethanol and finally, carrying out drying so as to obtain the natural cinnamic acid with a melting point of 132 to 132.5 DEG C. The raw material cinnamaldehyde used in the method is easily available, and the method has the advantages of a few reaction steps, safe operation, high product purity and applicability to large-scale production.
Description
Technical field
The present invention relates to a kind of synthetic method of flavouring agent styracin, the method for synthetic cinnamic acid, belongs to chemical technology field.
Background technology
For a long time, styracin synthetic is all taking phenyl aldehyde and aceticanhydride as raw material, synthesize by chemical reaction, the styracin that this kind of synthetic method obtains cannot reach the requirement of current food to natural green, and natural meat cinnamic acid occurring in nature only trace be present in Oleum Cinnamomi, be difficult to the demand that extensive supply market constantly expands.
Another mode, be taking Oleum Cinnamomi the inside a large amount of single phenylacroleins from out as raw material, by being that phenyl cinnamic aldehyde is oxidized synthesizing cinnamic acid to phenylacrolein, this kind of mode has similar report at US-3162682, but this kind of mode, need to be taking expensive Silver Nitrate as oxygenant, and oxidation unit complexity, complex process, aftertreatment difficulty, be therefore difficult to generate natural level product.
Summary of the invention
In order to overcome the deficiencies in the prior art, the object of the present invention is to provide that a kind of raw material is easy to get, synthesis step is simple and there is the method for the synthesis of natural styracin of high yield.
The present invention is achieved through the following technical solutions:
A method for synthesis of natural styracin, is characterized in that, comprises the following steps:
(1) choose starting material: first choosing a large amount of lists in Oleum Cinnamomi the inside is raw material from phenylacrolein out, and is dissolved in sodium dihydrogen phosphate buffer;
(2) synthesizing cinnamic acid: add hydrogen peroxide reagent and phase-transfer catalyst in phenylacrolein solution step (1) Suo Shu, then dripping Glacial acetic acid adjusting pH value is 4, then under the condition of room temperature, slowly splash into while stirring the cooled chlorite aqueous solution, after being added dropwise to complete, stir again 4～5 hours, to reacting completely, then cool to below-10 DEG C, suction filtration, use again ethyl alcohol recrystallization, after oven dry fusing point is the natural meat cinnamic acid of 132 °～132.5 °, its chemical equation is:
Above-mentioned phase-transfer catalyst is quaternary ammonium salt, and described quaternary ammonium salt can be tri-n-octyl methyl ammonium chloride.
The mol ratio of above-mentioned styracin and chlorite oxygenant is: 1: 2～3.
Above-mentioned styracin and the mol ratio of hydrogen peroxide are: 1: 2～2.8.
The concentration of above-mentioned hydrogen peroxide is 30%.
The invention has the beneficial effects as follows: the raw meat cinnamic aldehyde that the present invention uses easily obtains, and whole reactions steps is short, operational safety, product purity are high, can be used for extensive generation.
Embodiment
Below in conjunction with specific embodiment, describe the present invention in detail:
A method for synthesis of natural styracin, comprises the following steps:
(1) choose starting material: first choosing a large amount of lists in Oleum Cinnamomi the inside is raw material from phenylacrolein out, and is dissolved in sodium dihydrogen phosphate buffer;
(2) synthesizing cinnamic acid: add hydrogen peroxide reagent and phase-transfer catalyst in phenylacrolein solution step (1) Suo Shu, then dripping Glacial acetic acid adjusting pH value is 4, then under the condition of room temperature, slowly splash into while stirring the cooled chlorite aqueous solution, after being added dropwise to complete, stir again 4～5 hours, to reacting completely, then cool to below-10 DEG C, suction filtration, use again ethyl alcohol recrystallization, after oven dry fusing point is the natural meat cinnamic acid of 132 °～132.5 °, its chemical equation is:
Wherein phase-transfer catalyst is quaternary ammonium salt, and in the present embodiment, quaternary ammonium salt is tri-n-octyl methyl ammonium chloride.
And the mol ratio of above-mentioned styracin and chlorite oxygenant is: 1: 2～3, the mol ratio of styracin and hydrogen peroxide is: 1: 2～2.8, and the concentration of above-mentioned hydrogen peroxide is 30%.
Specific embodiment is as follows:
Embodiment 1:
In 250ml four-hole boiling flask, add 50ml water, then add 0.05mol (6.6g) phenylacrolein to be dissolved, add again 0.001g tri-n-octyl methyl ammonium chloride, 15ml30% hydrogen peroxide and 2g SODIUM PHOSPHATE, MONOBASIC, the ph value that adds again several Glacial acetic acid regulator solutions is 4, then under the condition of room temperature, splash into the 14g sodium chlorite solution who is dissolved in 90ml water, after dripping off, stir again 4～5 hours, after completion of the reaction, cool to-10 DEG C, suction filtration, dry with ethyl alcohol recrystallization again, obtain fusing point at 132 DEG C to 132.5 DEG C sterlings, productive rate 85%.
Embodiment 2:
In 250ml four-hole boiling flask, add 50ml water, then add 0.05mol (6.6g) phenylacrolein to be dissolved, add again 0.001g tri-n-octyl methyl ammonium chloride, 18ml30% hydrogen peroxide and 2g SODIUM PHOSPHATE, MONOBASIC, the ph value that adds again several Glacial acetic acid regulator solutions is 4, then splash at ambient temperature the 15g sodium chlorite solution who is dissolved in 100ml water, after dripping off, stir again 4～5 hours, after completion of the reaction, cool to-10 DEG C, suction filtration, dry with ethyl alcohol recrystallization again, obtain fusing point at 132 DEG C to 132.5 DEG C sterlings, productive rate 75%.
Below disclose the present invention with preferred embodiment, so it is not intended to limiting the invention, and all employings are equal to replaces or the technical scheme that obtains of equivalent transformation mode, within all dropping on protection scope of the present invention.
Claims (6)
1. a method for synthesis of natural styracin, is characterized in that, comprises the following steps:
(1) choose starting material: first choosing a large amount of lists in Oleum Cinnamomi the inside is raw material from phenylacrolein out, and is dissolved in sodium dihydrogen phosphate buffer;
(2) synthesizing cinnamic acid: add hydrogen peroxide reagent and phase-transfer catalyst in phenylacrolein solution step (1) Suo Shu, then dripping Glacial acetic acid adjusting pH value is 4, then under the condition of room temperature, slowly splash into while stirring the cooled chlorite aqueous solution, after being added dropwise to complete, stir again 4～5 hours, to reacting completely, then cool to below-10 DEG C, suction filtration, use again ethyl alcohol recrystallization, after oven dry fusing point is the natural meat cinnamic acid of 132 °～132.5 °, its chemical equation is:
2. the method for synthesis of natural styracin according to claim 1, is characterized in that, described phase-transfer catalyst is quaternary ammonium salt.
3. the method for synthesis of natural styracin according to claim 2, is characterized in that, described quaternary ammonium salt is tri-n-octyl methyl ammonium chloride.
4. the method for synthesis of natural styracin according to claim 1, is characterized in that, the mol ratio of described styracin and chlorite oxygenant is: 1: 2～3.
5. the method for synthesis of natural styracin according to claim 1, is characterized in that, described styracin and the mol ratio of hydrogen peroxide are: 1: 2～2.8.
6. the method for synthesis of natural styracin according to claim 1, is characterized in that, the concentration of described hydrogen peroxide is 30%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310097036.1A CN104072360A (en) | 2013-03-25 | 2013-03-25 | Synthetic method for natural cinnamic acid |
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| CN201310097036.1A CN104072360A (en) | 2013-03-25 | 2013-03-25 | Synthetic method for natural cinnamic acid |
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| CN201310097036.1A Pending CN104072360A (en) | 2013-03-25 | 2013-03-25 | Synthetic method for natural cinnamic acid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104402701A (en) * | 2014-11-21 | 2015-03-11 | 华侨大学 | New process for synthetizing strawberry acid |
| CN106748680A (en) * | 2016-11-22 | 2017-05-31 | 盐城市春竹香料有限公司 | A kind of preparation method of phenylacetaldehyde |
| CN110128262A (en) * | 2019-03-28 | 2019-08-16 | 新昌县泰如科技有限公司 | A kind of processing method synthesizing cinnamic acid condensation reaction waste water |
-
2013
- 2013-03-25 CN CN201310097036.1A patent/CN104072360A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 姜志猛: "亚氯酸钠体系选择性氧化制备布洛芬及其它羧酸", 《中国医药工业杂志》 * |
| 李艳 等: "综合性化学实验:从肉桂皮中提取肉桂醛的研究", 《咸宁学院学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104402701A (en) * | 2014-11-21 | 2015-03-11 | 华侨大学 | New process for synthetizing strawberry acid |
| CN104402701B (en) * | 2014-11-21 | 2016-04-13 | 华侨大学 | A kind of strawberriff new synthetic process |
| CN106748680A (en) * | 2016-11-22 | 2017-05-31 | 盐城市春竹香料有限公司 | A kind of preparation method of phenylacetaldehyde |
| CN106748680B (en) * | 2016-11-22 | 2018-05-01 | 盐城市春竹香料有限公司 | A kind of preparation method of phenylacetaldehyde |
| CN110128262A (en) * | 2019-03-28 | 2019-08-16 | 新昌县泰如科技有限公司 | A kind of processing method synthesizing cinnamic acid condensation reaction waste water |
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Application publication date: 20141001 |