CN101811948A - Method for synthesizing pentanone-2 through Bayer-Vlieger oxidation reaction - Google Patents
Method for synthesizing pentanone-2 through Bayer-Vlieger oxidation reaction Download PDFInfo
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Abstract
The invention relates to a method for synthesizing pentanone-2 through a Bayer-Vlieger oxidation reaction. The pentanone-2 is prepared by using propionaldehyde as a raw material, performing alkaline condensation and the Bayer-Vlieger oxidation reaction on the propionaldehyde, and finally performing hydrolysis under an acid condition. The method comprises the following process steps of: (1) condensing the propionaldehyde at the temperature of 30 to 40 DEG C under the action of solution of NaOH to obtain 2-methyl-2-pentenal; (2) preparing buffer solution of acetic acid and sodium acetate from the product obtained in the step (1) by taking the acetic acid as solvent in the presence of the sodium acetate, controlling the pH of a reaction system to be between 3.7 and 6, and at the temperature of 10 to 30 DEG C, using peroxyacetic acid to perform B-V oxidation so as to obtain formic acid-2-amylene-2-alcohol ester; and (3) using H2SO4 aqueous solution to reflux and hydrolyze the product obtained in the step (2) under an acidic condition to prepare the pentanone-2. The quality of the pentanone-2 meets the requirements of preparing a flavoring essence and an essence for household and personal care chemicals. The method has the advantages of readily available raw materials, simple process, high yield, single product component, easy refining, high product quality, low cost and suitability for industrial production.
Description
Technical field
The invention belongs to the spices technical field of organic synthesis, relate to a kind of method of synthetic pentanone-2, relating in particular to a kind of is the novel method of the synthetic pentanone-2 of Bayer-Wei Lie reaction grid (Baeyer-villiger is called for short the B-V reaction) of oxygenant with peroxide reagent.
Background technology
Pentanone-the 2nd, a kind of important perfume material, it has pure and fresh elegant ether perfume (or spice), and is fragrant and sweet, the fragrance of leavened cheese and similar banana fruit sample.Can be widely used in also can being used for various fruit flavour type daily chemical essences in cheddar cheese, milk, banana, Fructus Artocarpi Heterophylli and other fruit flavour type food flavours.
Producing of pentanone-2, the useful lime acetate of bibliographical information and Calcium Butyrate destructive distillation (Annalen, 108,124,1858) method is produced, and also available n-caproic acid sodium or n-caproic acid are produced with hydrogen peroxide oxidation, but the finished product complicated component that these methods are produced, product are difficult to purify.
The B-V reaction is a kind of chemical reaction of classics, and it is in the presence of peroxide reagent, the reaction of oxidized generation ester of aldehyde and ketone or lactone, and its reaction formula is as follows:
Ketone is taking place can both to generate ester or lactone smoothly when B-V reacts, and when the B-V reaction took place aldehydes, because the easily oxidizable matter of aldehyde radical, primary product was that aldehyde radical is oxidized to carboxylic acid, and the yield that oxidation generation manthanoate takes place is very low.Aldehydes with two keys also can be difficult to the B-V oxidation products (Hu Yuefei, woods Guoqiang: " modern organic reaction " Vol.1-50, Chemical Industry Press, 2008,12, Beijing) that obtains expecting with side reactions such as generation epoxide when the B-V reaction takes place
Summary of the invention
The purpose of this invention is to provide a kind of is the Bayer-Wei Lie reaction grid of oxygenant with peroxide reagent, will have α, and the propenal of beta substitution is through the novel method of oxidation and the synthetic pentanone-2 of hydrolysis reaction.
For achieving the above object, the technical solution used in the present invention is:
A kind of method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction is characterized in that: with the propionic aldehyde raw material, and through the parlkaline condensation, Bayer-Wei Liege oxidation, hydrolysis obtains pentanone-2 under acidic conditions at last, and its processing step is as follows:
(1) propionic aldehyde is under the effect of the NaOH aqueous solution, and condensation makes 2-methyl-2-pentenals under 30～40 ℃ of temperature;
(2) product that step (1) is obtained is made solvent with acetic acid, in the presence of pH value conditioning agent sodium-acetate, form acetic acid-sodium acetate buffer solution, control reactive system pH=3.7～6, under 10～30 ℃ of temperature, carry out Bayer-Wei Liege oxidation with Peracetic Acid, obtain formic acid-2-amylene-2-alcohol ester;
(3) product that step (2) is obtained is used H under acidic conditions
2SO
4Aqueous solution back hydrolysis makes pentanone-2.
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: in the described step (1), propionic aldehyde makes 2-methyl-2-pentenals 30 ℃ of following condensations under 1% NaOH aqueous solution effect.
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: in the described step (2), Peracetic Acid with 20% carries out Bayer-Wei Liege oxidation, must be in the buffered soln of acetic acid sodium-acetate, the control reactive system is that 3.7～6 scope is carried out in the pH value, obtains formic acid-2-amylene-2-alcohol ester.
According to described method, it is characterized in that: in the described step (3), use 10%H with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction
2SO
4Aqueous solution back hydrolysis makes pentanone-2.
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: the Peracetic Acid that uses in the described step (2) is the Peracetic Acid of 20%～40% concentration.
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: the reaction times is 4～6 hours in the described step (2).
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: the consumption of Peracetic Acid is 0.9～1.1 for the mol ratio of it and 2-methyl-2-pentenals in the described step (2); Solvent acetic acid and 2-methyl-2-pentenals weight ratio is: 1.5～2: 1; The weight ratio of solvent acetic acid and sodium-acetate is 1～3: 1.
According to described method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction, it is characterized in that: the concentration of Peracetic Acid is 20% in the described step (2), and its consumption is 1: 1 for the mol ratio of it and 2-methyl-2-pentenals; The weight ratio of solvent acetic acid and sodium-acetate is 2.5: 1.
According to described method, it is characterized in that its concrete processing step is as follows with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction:
(1) preparation 2-methyl-2-pentenals
Be equipped with in the three-necked flask of agitator, thermometer and dropping funnel one, the NaOH aqueous solution 1000 grams of adding 1% stir Dropwise 35 0 gram propionic aldehyde down, react 5 hours under 30 ℃ of left and right sides temperature after dropwising again, be neutralized to neutrality with Glacial acetic acid again, static layering is divided water-yielding stratum, and water layer is extraction liquid and oil reservoir merging after extracting, be washed to neutrality, underpressure distillation behind the recovery solvent is collected to such an extent that 2-methyl-2-pentenals 250 restrains yield 85%;
(2) Bayer of 2-methyl-2-pentenals-Wei Liege oxidation gets 2-methyl-2-pentenol manthanoate
One agitator is housed, in 1 liter the three-necked flask of thermometer and dropping funnel, add 2-methyl-2-pentenals 90 grams, acetic acid 150 grams, sodium acetate, anhydrous 60 grams, Peracetic Acid 330 grams of dropping 20% under 10～20 ℃ temperature, are warming up to 25 ℃ and continue reaction 4 hours at about 1 hour of dropping time after dropwising, after reaction finishes, material is poured in the 1000ml water, after fully stirring, behind the static minute oil-yielding stratum, after water layer extracts with methyl tertiary butyl ether, merge washing, obtain product 82 grams behind the recovery solvent, gas chromatographic analysis shows, unoxidized 2-methyl-2-pentenals is 10.2%, oxidation yield 70%;
(3) enol ester hydrolysis system pentanone-2
In the three-necked flask that thermometer, reflux exchanger and agitator are housed, adding 2-methyl-2-amylene alcohol ester 82 grams of above-mentioned preparation and 5% sulfuric acid 120 grams under agitation refluxed 6 hours, oil-yielding stratum is divided in the cooling back, water layer is after extraction, extraction liquid and oil reservoir merge, the washing fractionation gets product 2 pentanone 58 grams, and the hydrolysis yield is 96%, product content 99%.
Beneficial effect of the present invention: technological process of the present invention is to be raw material with the propionic aldehyde, make 2-methyl-2-pentenals through alkaline aldol condensation, it is under the condition of control pH=3.7～6, using 20% Peracetic Acid carries out Bayer-Wei Liege oxidation and obtains behind the formic acid enol ester method that hydrolysis again generates pentanone-2, product is analyzed content through GC and is reached 99%, quality satisfies the requirement of allotment food flavour and daily chemical essence, this raw materials technology is easy to get, technological process is simple, the yield height, and product is formed single, be easy to make with extra care, good product quality, cost is low, is fit to suitability for industrialized production.
Embodiment
The invention will be further described below in conjunction with specific embodiment:
The present invention relates to a kind of is the Bayer-Wei Lie reaction grid (Baeyer-villiger of oxygenant with peroxide reagent, be called for short the B-V reaction), to have α, the propenal of beta substitution, make the novel method of ketone compounds through oxidation and hydrolysis reaction, and successfully prepared pentanone-2 with 2-methyl-2-pentenals.
To having α, discovering of B-V reaction takes place in the propenal compounds of beta substitution based on us, and when reaction medium acidity when strong (pH＜3.7), aldehydes mainly is oxidized to carboxylic acid and seldom generates the formic acid enol ester.Easy initial ring oxidizing reaction when medium is alkalescence (pH＞8) generates epoxy compounds on two keys, reactions such as polymerization also can take place simultaneously.When carrying out in B-V is reflected at the scope of pH=3.7～6, above-mentioned side reaction all is suppressed, and reaction product has mainly generated the formic acid enol ester, obtains ketone compounds through hydrolysis again, and this result is document report not in the past.The result has determined the novel method of synthetic pentanone-2 in view of the above.
Technological process of the present invention is to be raw material with the propionic aldehyde, make 2-methyl-2-pentenals through alkaline aldol condensation, it is under the condition of control pH=3.7～6, using 20% Peracetic Acid carries out Bayer-Wei Liege oxidation and obtains behind the formic acid enol ester method that hydrolysis again generates pentanone-2, product is analyzed content through GC and is reached 99%, quality satisfies the requirement of allotment food flavour and daily chemical essence, this raw materials technology is easy to get, technological process is simple, the yield height, and product is formed single, be easy to make with extra care, good product quality, cost is low, is fit to suitability for industrialized production.
The present invention is raw material stepwise synthesis pentanone-2 with the propionic aldehyde, and its technology is as follows:
Technical scheme of the present invention:
(1) with the propionic aldehyde is raw material, aldol condensation takes place 30～40 ℃ the time, obtain 2-methyl-2-pentenals with the aqueous sodium hydroxide solution of 1% concentration.
(2) product that (1) is obtained is made solvent with acetic acid, in the presence of pH value conditioning agent sodium-acetate, form acetic acid-sodium acetate buffer solution, control reactive system pH=3.7～6, under 10～30 ℃ of temperature, carry out the B-V oxidation with 20% Peracetic Acid, the reaction times is 4～6 hours, obtains formic acid 2-amylene-2 alcohol ester.
It is the key of technology success that above-mentioned reaction pH value is regulated, and pH=3.7～5.6 of acetic acid-sodium acetate buffer system are fit to the requirement of technology.
Above-mentioned peroxidation agent is: organic peroxy reagent such as Peracetic Acid, benzoyl hydroperoxide, metachloroperbenzoic acid.Peroxide reagent adopts the Peracetic Acid of 20%～40% concentration, and preferably concentration is 20%～25%.Peracetic Acid with 20% in this technology is good, and it easily prepares cheap, and is safe in utilization.
The consumption of 20% Peracetic Acid is 0.9～1.1 to be advisable with the mol ratio of it and 2-methyl-2-pentenals; Best: 1: 1.
Solvent acetic acid and 2-methyl-2-pentenals weight ratio is: 1.5～2: 1;
The weight ratio of solvent acetic acid and sodium-acetate is 1～3: 1.Best: 2.5: 1
Above-mentioned reactant must be to have α, the propenal of beta substitution, and 2-methyl-2-pentenals is exactly a kind of.
The temperature of the Peracetic Acid of above-mentioned dropping 20% is 10～30 ℃, and optimum temps is 10～20 ℃ of products that (3) obtain (2), and back hydrolysis in 10% aqueous sulfuric acid makes pentanone-2.Alkaline hydrolysis is easy to cause side reactions such as aldol condensation.
The invention has the advantages that technology is simple, cost is low, and product is easy to make with extra care, and the yield of pentanone-2 can reach 56%.
Embodiment
1, preparation 2-methyl-2-pentenals
Be equipped with in the three-necked flask of agitator, thermometer and dropping funnel one, the NaOH aqueous solution 1000 grams of adding 1% stir Dropwise 35 0 gram propionic aldehyde down, react 5 hours under 30 ℃ of left and right sides temperature after dropwising again, be neutralized to neutrality with Glacial acetic acid again, static layering is divided water-yielding stratum, and water layer is extraction liquid and oil reservoir merging after extracting, be washed to neutrality, underpressure distillation behind the recovery solvent is collected to such an extent that 2-methyl-2-pentenals 250 restrains yield 85%.
2, the B-V oxidation of 2-methyl-2-pentenals gets 2-methyl-2-pentenol manthanoate.
One agitator is housed, in 1 liter the three-necked flask of thermometer and dropping funnel, add 2-methyl-2-pentenals 90 grams, acetic acid 150 grams, sodium acetate, anhydrous 60 grams, Peracetic Acid 330 grams of dropping 20% under 10～20 ℃ temperature, are warming up to 25 ℃ and continue reaction 4 hours at about 1 hour of dropping time after dropwising, after reaction finishes, material is poured in the 1000ml water, after fully stirring, behind the static minute oil-yielding stratum, after water layer extracts with methyl tertiary butyl ether, merge washing, obtain product 82 grams behind the recovery solvent, gas chromatographic analysis shows, unoxidized 2-methyl-2-pentenals is 10.2%, oxidation yield 70%.
3. enol ester hydrolysis system pentanone-2
In the three-necked flask that thermometer, reflux exchanger and agitator are housed, adding 2-methyl-2-amylene alcohol ester 82 grams of above-mentioned preparation and 5% sulfuric acid 120 grams under agitation refluxed 6 hours, oil-yielding stratum is divided in the cooling back, water layer is after extraction, extraction liquid and oil reservoir merge, the washing fractionation gets product 2 pentanone 58 grams, and the hydrolysis yield is 96%, product content 99%.
Embodiment recited above is described preferred implementation of the present invention; be not that design of the present invention and protection domain are limited; under the prerequisite that does not break away from design concept of the present invention; common engineering technical personnel make technical scheme of the present invention in this area various modification and improvement all should fall into protection scope of the present invention.
Claims (9)
1. method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction is characterized in that: with the propionic aldehyde raw material, and through the parlkaline condensation, Bayer-Wei Liege oxidation, hydrolysis obtains pentanone-2 under acidic conditions at last, and its processing step is as follows:
(1) propionic aldehyde is under the effect of the NaOH aqueous solution, and condensation makes 2-methyl-2-pentenals under 30～40 ℃ of temperature;
(2) product that step (1) is obtained is made solvent with acetic acid, in the presence of pH value conditioning agent sodium-acetate, form acetic acid-sodium acetate buffer solution, control reactive system pH=3.7～6, under 10～30 ℃ of temperature, carry out Bayer-Wei Liege oxidation with Peracetic Acid, obtain formic acid-2-amylene-2-alcohol ester;
(3) product that step (2) is obtained is used H under acidic conditions
2SO
4Aqueous solution back hydrolysis makes pentanone-2.
2. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1, it is characterized in that: in the described step (1), propionic aldehyde makes 2-methyl-2-pentenals 30 ℃ of following condensations under 1% NaOH aqueous solution effect.
3. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1, it is characterized in that: in the described step (2), Peracetic Acid with 20% carries out Bayer-Wei Liege oxidation, must be in the buffered soln of acetic acid sodium-acetate, the control reactive system is that 3.7～6 scope is carried out in the pH value, obtains formic acid-2-amylene-2-alcohol ester.
4. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that: in the described step (3), use 10% H
2SO
4Aqueous solution back hydrolysis makes pentanone-2.
5. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that: the Peracetic Acid that uses in the described step (2) is the Peracetic Acid of 20%～40% concentration.
6. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that: the reaction times is 4～6 hours in the described step (2).
7. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that: the consumption of Peracetic Acid is 0.9～1.1 for the mol ratio of it and 2-methyl-2-pentenals in the described step (2); Solvent acetic acid and 2-methyl-2-pentenals weight ratio is: 1.5～2: 1; The weight ratio of solvent acetic acid and sodium-acetate is 1～3: 1.
8. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that: the concentration of Peracetic Acid is 20% in the described step (2), and its consumption is 1: 1 for the mol ratio of it and 2-methyl-2-pentenals; The weight ratio of solvent acetic acid and sodium-acetate is 2.5: 1.
9. the method with the synthetic pentanone-2 of Bayer-Wei Liege oxidizing reaction according to claim 1 is characterized in that its concrete processing step is as follows:
(1) preparation 2-methyl-2-pentenals
Be equipped with in the three-necked flask of agitator, thermometer and dropping funnel one, the NaOH aqueous solution 1000 grams of adding 1% stir Dropwise 35 0 gram propionic aldehyde down, react 5 hours under 30 ℃ of left and right sides temperature after dropwising again, be neutralized to neutrality with Glacial acetic acid again, static layering is divided water-yielding stratum, and water layer is extraction liquid and oil reservoir merging after extracting, be washed to neutrality, underpressure distillation behind the recovery solvent is collected to such an extent that 2-methyl-2-pentenals 250 restrains yield 85%;
(2) Bayer of 2-methyl-2-pentenals-Wei Liege oxidation gets 2-methyl-2-pentenol manthanoate
One agitator is housed, in 1 liter the three-necked flask of thermometer and dropping funnel, add 2-methyl-2-pentenals 90 grams, acetic acid 150 grams, sodium acetate, anhydrous 60 grams, Peracetic Acid 330 grams of dropping 20% under 10～20 ℃ temperature, are warming up to 25 ℃ and continue reaction 4 hours at about 1 hour of dropping time after dropwising, after reaction finishes, material is poured in the 1000ml water, after fully stirring, behind the static minute oil-yielding stratum, after water layer extracts with methyl tertiary butyl ether, merge washing, obtain product 82 grams behind the recovery solvent, gas chromatographic analysis shows, unoxidized 2-methyl-2-pentenals is 10.2%, oxidation yield 70%;
(3) enol ester hydrolysis system pentanone-2
In the three-necked flask that thermometer, reflux exchanger and agitator are housed, adding 2-methyl-2-amylene alcohol ester 82 grams of above-mentioned preparation and 5% sulfuric acid 120 grams under agitation refluxed 6 hours, oil-yielding stratum is divided in the cooling back, water layer is after extraction, extraction liquid and oil reservoir merge, the washing fractionation gets product 2 pentanone 58 grams, and the hydrolysis yield is 96%, product content 99%.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102100230A (en) * | 2010-12-29 | 2011-06-22 | 华南农业大学 | New use of 2-methyl-2-pentenal serving as bactericide |
| CN102653510A (en) * | 2011-03-04 | 2012-09-05 | 上海爱普植物科技有限公司 | Production method of 2-methyl-2-pentenoic acid |
| CN103641711A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Preparation method of 3-oxo-carboxylic acid ester derivative |
| CN104447255A (en) * | 2014-12-11 | 2015-03-25 | 派尔科化工材料（启东）有限公司 | Method for preparing 2-pentanone from 2-amylene |
| CN106554359A (en) * | 2015-09-25 | 2017-04-05 | 南京理工大学 | Application of the sulfonated graphene resin type catalyst in Baeyer-Villiger oxidation reactions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1426991A (en) * | 2001-12-18 | 2003-07-02 | 上海家化（集团）有限公司 | Synthesis of heptanone-3 |
-
2010
- 2010-03-22 CN CN 201010133749 patent/CN101811948A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1426991A (en) * | 2001-12-18 | 2003-07-02 | 上海家化（集团）有限公司 | Synthesis of heptanone-3 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102100230A (en) * | 2010-12-29 | 2011-06-22 | 华南农业大学 | New use of 2-methyl-2-pentenal serving as bactericide |
| CN102653510A (en) * | 2011-03-04 | 2012-09-05 | 上海爱普植物科技有限公司 | Production method of 2-methyl-2-pentenoic acid |
| CN103641711A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Preparation method of 3-oxo-carboxylic acid ester derivative |
| CN103641711B (en) * | 2013-12-18 | 2015-07-01 | 福建省永安市智源生化有限公司 | Preparation method of 3-oxo-carboxylic acid ester derivative |
| CN104447255A (en) * | 2014-12-11 | 2015-03-25 | 派尔科化工材料（启东）有限公司 | Method for preparing 2-pentanone from 2-amylene |
| CN106554359A (en) * | 2015-09-25 | 2017-04-05 | 南京理工大学 | Application of the sulfonated graphene resin type catalyst in Baeyer-Villiger oxidation reactions |
| CN106554359B (en) * | 2015-09-25 | 2018-08-10 | 南京理工大学 | Application of the sulfonated graphene resin type catalyst in Baeyer-Villiger oxidation reactions |
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Application publication date: 20100825 |