CN101402628A - Synthesis of gamma-undecalactone - Google Patents
Synthesis of gamma-undecalactone Download PDFInfo
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- CN101402628A CN101402628A CNA2008101529534A CN200810152953A CN101402628A CN 101402628 A CN101402628 A CN 101402628A CN A2008101529534 A CNA2008101529534 A CN A2008101529534A CN 200810152953 A CN200810152953 A CN 200810152953A CN 101402628 A CN101402628 A CN 101402628A
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- octanol
- undecalactone
- gamma
- initiator
- reaction
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Abstract
The invention discloses a method for synthesizing gamma-undecalactone, which belongs to a synthesis technology of the gamma-undecalactone. The method takes n-octanol as a solvent, boric acid or zinc bromide as a catalyst, acrylic acid as a raw material and di-t-butyl peroxide or dibenzoyl peroxide as an initiator, and comprises the following steps: firstly, adding partial n-octanol and the catalyst into a reaction kettle to be mixed and heated; secondly, mixing the remaining n-octanol, the initiator and the acrylic acid and dipping the mixture into the reaction kettle; thirdly, making the mixture react for a period; and finally obtaining reaction liquid containing the gamma-undecalactone. The method has the advantages that the reaction is carried out at normal pressure, byproducts of tert-butyl alcohol are easy to discharge from a system during the reaction process, and simultaneously the equipment used by the method is simple, the synthesis cost is low and the yield of the gamma-undecalactone is high.
Description
Technical field
The present invention relates to a kind of synthetic method of γ-Shi Yineizhi, belong to the synthetic technology of γ-Shi Yineizhi.
Background technology
γ-Shi Yineizhi is called peach aldehyde again, has intensive peach fragrance, and natural being present in cream, sweet osmanthus, peach, apricot, Purple Granadilla, the hydrolytic soya bean protein is one of lactone spice of using always.
At present, the γ-Shi Yineizhi spices on the market is mainly derived from chemosynthesis.The chemosynthesis of γ-Shi Yineizhi has several different methods, and comparatively traditional method is that the raw material dehydration generates the synthetic γ-Shi Yineizhi of alkene with alcohol as using the synthetic γ-Shi Yineizhi of undecylenic acid isomerization in sulfuric acid, is the synthetic γ-Shi Yineizhi of raw material etc. with the furfural.
Relevant γ-Shi Yineizhi synthetic patent is also more.Patent US5665696 has reported with tetrahydrofuran (THF) through the synthetic γ-Shi Yineizhi of addition reaction.Patent US7129067 has reported with Viscotrol C and yeast extract through the synthetic γ-Shi Yineizhi that ferments.Japanese Patent JP51023256 and JP51095058 have reported with n-Octanol and acrylate and have synthesized γ-Shi Yineizhi through free radical reaction.On this basis, patent JP8231525 reported with n-Octanol and water-containing acrylic acid under high pressure (about 2atm) react synthetic γ-Shi Yineizhi.When this patent is synthesized γ-Shi Yineizhi with vinylformic acid (moisture) with n-Octanol, be to carry out under the condition of high pressure catalyst-free, to equipment requirement of withstand voltage height, and there is certain risk in pressure height in the preparation process.And relevantly under normal pressure catalyzer condition, do not appear in the newspapers as yet with the technology of the synthetic γ-Shi Yineizhi of vinylformic acid.
Summary of the invention
The synthetic method that the purpose of this invention is to provide a kind of γ-Shi Yineizhi.This method has the process characteristic of simple.
The present invention is realized by following technical proposals: a kind of synthetic method of γ-Shi Yineizhi, it is characterized in that comprising following process: be solvent with the n-Octanol, with boric acid or zinc bromide is catalyzer, with vinylformic acid is raw material, with di-t-butyl peroxide or dibenzoyl peroxide is initiator, and be 5～7: 1 by n-Octanol and acrylic acid mol ratio, vinylformic acid and initiating radical mol ratio are 8～13: 1, the mol ratio of vinylformic acid and catalyzer is 39: 1 preparation materials.At first 3/4 and catalyzer with the n-Octanol consumption joins reactor, stirs down Heating temperature to 160-190 ℃, and then will remaining n-Octanol and initiator and vinylformic acid be added drop-wise in the reactor after mixing.Rate of addition is 2.5～3mL/h, and return time is 3～5h.Obtain containing the reaction solution of γ-Shi Yineizhi.
The invention has the advantages that: be reflected under the normal pressure and carry out, trimethyl carbinol by product is easy to discharge from system in reaction process, helps the carrying out of positive reaction on the one hand, hinders side reaction; On the other hand, the separation that helps follow-up γ-Shi Yineizhi is purified.The equipment of Shi Yonging is simple simultaneously, and synthetic cost is low, γ-Shi Yineizhi productive rate height.
Embodiment
Embodiment one
The balance dropping funnel is being housed, thermometer, add the 75mL n-Octanol in the 250mL there-necked flask of prolong, taking by weighing 0.2g boric acid joins in the flask, with magnetic agitation electric mantle heated and stirred, rotating speed is 500r/min, behind the temperature-stable to 170 ℃, begin to drip the mixture of being made up of 25mL n-Octanol, 2.4mL di-t-butyl peroxide and 8.7mL vinylformic acid, dropping V-bar is 2.62mL/h.After dripping end, keep 170 ℃ of backflow 3h of temperature, finish reaction.Productive rate is 80.53%.
Embodiment two
The balance dropping funnel is being housed, and thermometer adds the 66mL n-Octanol in the 250mL there-necked flask of prolong
Taking by weighing the 0.46g zinc bromide joins in the flask, with magnetic agitation electric mantle heated and stirred, rotating speed is 400r/min, behind the temperature-stable to 170 ℃, begin to drip the mixture of being made up of 22mL n-Octanol, 1.82mL di-t-butyl peroxide and 5.47mL vinylformic acid, dropping V-bar is 2.7mL/h.After dripping end, keep 170 ℃ of backflow 5h of temperature.Finish reaction.Productive rate is 79.98%.
Embodiment three
The balance dropping funnel is being housed, thermometer, add the 100mL n-Octanol in the 500mL there-necked flask of prolong, taking by weighing the 0.7g zinc bromide joins in the flask, with magnetic agitation electric mantle heated and stirred, rotating speed is 350r/min, behind the temperature-stable to 180 ℃, begin to drip the mixture of being made up of 33mL n-Octanol, 2.1mL di-t-butyl peroxide and 8.9mL vinylformic acid, dropping V-bar is 2.91mL/h.After dripping end, keep 180 ℃ of backflow 4h of temperature.Finish reaction.Productive rate is 78.52%.
Embodiment four
The balance dropping funnel is being housed, thermometer, add the 70mL n-Octanol in the 500mL there-necked flask of prolong, taking by weighing 0.15g boric acid joins in the flask, with magnetic agitation electric mantle heated and stirred, rotating speed is 400r/min, behind the temperature-stable to 175 ℃, begin to drip the mixture of being made up of 24mL n-Octanol, 1.83mL di-t-butyl peroxide and 6.8mL vinylformic acid, dropping V-bar is 2.87mL/h.After dripping end, keep 175 ℃ of backflow 4h of temperature.Finish reaction.The γ-Shi Yineizhi productive rate is 79.62%.
Claims (1)
1. the synthetic method of a γ-Shi Yineizhi, it is characterized in that comprising following process: be solvent with the n-Octanol, with boric acid or zinc bromide is catalyzer, with vinylformic acid is raw material, with di-t-butyl peroxide or dibenzoyl peroxide is initiator, and be 5～7: 1 by n-Octanol and acrylic acid mol ratio, vinylformic acid and initiator mol ratio are 8～13: 1, the mol ratio of vinylformic acid and catalyzer is 39: 1 preparation materials, at first 3/4 and catalyzer with the consumption of n-Octanol joins reactor, Heating temperature is to 160-190 ℃ under stirring, and then will be added drop-wise in the reactor after remaining n-Octanol and initiator and the vinylformic acid mixing, rate of addition is 2.5-～3mL/ hour, and return time is 3～4 hours, obtains containing the reaction solution of γ-Shi Yineizhi.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101529534A CN101402628A (en) | 2008-11-12 | 2008-11-12 | Synthesis of gamma-undecalactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101529534A CN101402628A (en) | 2008-11-12 | 2008-11-12 | Synthesis of gamma-undecalactone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101402628A true CN101402628A (en) | 2009-04-08 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101529534A Pending CN101402628A (en) | 2008-11-12 | 2008-11-12 | Synthesis of gamma-undecalactone |
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| CN (1) | CN101402628A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757411A (en) * | 2012-06-29 | 2012-10-31 | 天津大学 | Device and method for preparing peach aldehyde |
| CN103030614A (en) * | 2011-09-29 | 2013-04-10 | 南昌洋浦天然香料香精有限公司 | Extracting method of synthetic peach aldehyde |
-
2008
- 2008-11-12 CN CNA2008101529534A patent/CN101402628A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103030614A (en) * | 2011-09-29 | 2013-04-10 | 南昌洋浦天然香料香精有限公司 | Extracting method of synthetic peach aldehyde |
| CN102757411A (en) * | 2012-06-29 | 2012-10-31 | 天津大学 | Device and method for preparing peach aldehyde |
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| PB01 | Publication | ||
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Open date: 20090408 |