CN1426991A - Synthesis of heptanone-3 - Google Patents
Synthesis of heptanone-3 Download PDFInfo
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- CN1426991A CN1426991A CN 01142695 CN01142695A CN1426991A CN 1426991 A CN1426991 A CN 1426991A CN 01142695 CN01142695 CN 01142695 CN 01142695 A CN01142695 A CN 01142695A CN 1426991 A CN1426991 A CN 1426991A
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- heptanone
- synthesis technique
- oxidation
- hydrolysis
- condensation
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Abstract
A process for synthesizing heptanone-3 from butanal as raw material includes such steps as alkaline condensating, oxidizing with peroxyacetic acid, and finally hydrolyzing under the acidic condition. Its advantage is little environmental pollution.
Description
Technical field
The present invention relates to a kind of processing method of synthetic heptanone-3, relating in particular to a kind of is raw material with the butyraldehyde, the processing method of synthetic heptanone-3.
Technical background
Heptanone-the 3rd, a kind of important perfume material, it has sweet blue or green fragrant, fruital, and similar apple and with fresh pericarp fragrance in the natural aroma component that is present in apple, can be widely used in food and the daily chemical essence.
Usually the preparation method of heptanone-3 has following two kinds: a kind of is that another kind of method then is with valeraldehyde and C with heptyne-2 hydration
2H
5MgBr takes place to use the lead tetraacetate oxidation with the sodium dichromate 99 oxidation or with the butyl ethyl propanedioic acid in benzene and pyridine solution again behind the grignard reaction.Above-mentioned two methods all exist the raw material sources difficulty, the defective that three-waste pollution is serious.
Summary of the invention
The processing method of the synthetic heptanone-3 that the object of the present invention is to provide a kind of raw material to be easy to get, operating procedure is easy, environmental pollution is very low.
The processing method of synthetic heptanone-3 of the present invention is to be raw material with the butyraldehyde, carry out alkaline condensation with sodium hydroxide, temperature is controlled at 30 ℃～40 ℃, uses the Peracetic Acid oxidation in the presence of acetic acid or sodium-acetate, oxidizing temperature is 15 ℃～30 ℃, hydrolysis obtains heptanone-3 under the acidic conditions that acid such as sulfuric acid exist, and its reaction formula is as follows:
Prepared heptanone-3 of the present invention, raw material is easy to get, and technological operation is simple, and is with low cost, and environmental pollution is very low.
Embodiment
Embodiment 1
1. the preparation of 2-ethyl-2-hexenoic aldehyde:
Be equipped with in the three-necked flask of agitator, thermometer and dropping funnel one, add 1% NaOH aqueous solution 1000g, under agitation splash into the 425g butyraldehyde, dropwise the back and about 30 ℃, reacted 5 hours.Be neutralized to neutrality with Glacial acetic acid, divide water-yielding stratum, oil-reservoir water is washed till neutrality, and vacuum fractionation is collected 108～112 ℃/0.02MPa cut, gets 2-ethyl-2-hexenoic aldehyde 317g, content 98%.
2. the preparation of the formic acid enol ester of heptanone-3:
Be equipped with in the three-necked flask of agitator, thermometer, dropping funnel one, add 2-ethyl-2-hexenoic aldehyde 104g, Glacial acetic acid 200g, sodium acetate, anhydrous 60g under the ice bath cooling, drips 20% Peracetic Acid 300g, about 40 minutes of dropping time.After dropwising, allow the interior temperature of reactant rise to 25 ℃ gradually, control this temperature and continue reaction 5 hours.After reaction finishes, add 1500ml water, fully stir the back standing demix, divide oil-yielding stratum, water layer extracts with ethylene dichloride, and combining extraction liquid is used 1%Na
2S
2O
3Behind the solution washing, reclaim solvent and get concentrated solution 85g.The gas chromatographic analysis product consists of: heptanone-3 58.4%, and heptanone-3 formic acid enol ester 27.7%, 2-ethyl-2-hexenoic aldehyde 11.7%, other is 2.2% years old.Crude product is directly used in hydrolysis.
3. enol ester hydrolysis system heptanone-3:
Be equipped with in the three-necked flask of agitator, thermometer and reflux condensing tube one, add the sulfuric acid 100g of above-mentioned steps 2 prepared oxidation material 85g and 5%, be heated to 100 ℃ of stirrings 6 hours that reflux.Water-yielding stratum is divided in the cooling back, and oil-reservoir water is washed till neutrality, and vacuum fractionation is collected 81～82 ℃/0.01MPa fraction, gets product 46g (content is more than 99%).
Embodiment 2
1. the preparation of 2-ethyl-2-hexenoic aldehyde:
Be equipped with in the three-necked flask of agitator, thermometer and dropping funnel one, add 1% NaOH aqueous solution 1000g, under agitation splash into the 425g butyraldehyde, dropwise the back and about 35 ℃, reacted 4 hours.Be neutralized to neutrality with Glacial acetic acid, divide water-yielding stratum, oil-reservoir water is washed till neutrality, and vacuum fractionation is collected 108～112 ℃/0.02MPa cut, gets 2-ethyl-2-hexenoic aldehyde 317g, content 98%.
2. the preparation of the formic acid enol ester of heptanone-3:
Be equipped with in the three-necked flask of agitator, thermometer, dropping funnel one, add 2-ethyl-2-hexenoic aldehyde 104g, Glacial acetic acid 150g under the ice bath cooling, drips 20% Peracetic Acid 300g, about 40 minutes of dropping time.After dropwising, allow the interior temperature of reactant rise to 20 ℃ gradually, control this temperature and continue reaction 6 hours.After reaction finishes, add 1500ml water, fully stir the back standing demix, divide oil-yielding stratum, water layer extracts with ethylene dichloride, and combining extraction liquid is used 1%Na
2S
2O
3Behind the solution washing, reclaim solvent and get concentrated solution 86g.The gas chromatographic analysis product consists of: heptanone-3 68.4%, and heptanone-3 formic acid enol ester 4.6%, 2-ethyl-2-hexenoic aldehyde 15.8%, other is 1.2% years old.Crude product is directly used in hydrolysis.
3. enol ester hydrolysis system heptanone-3:
Be equipped with in the three-necked flask of agitator, thermometer and reflux condensing tube one, add the sulfuric acid 100g of above-mentioned steps 2 prepared oxidation material 86g and 5%, be heated to 100 ℃ of stirrings 6 hours that reflux.Water-yielding stratum is divided in the cooling back, and oil-reservoir water is washed till neutrality, and vacuum fractionation is collected 81～82 ℃/0.01MPa fraction, gets product 42g (content is more than 99%).
Claims (5)
1. the synthesis technique of a heptanone-3 is characterized in that, is raw material with the butyraldehyde, through parlkaline condensation, oxidation, hydrolysis obtains heptanone-3 under acidic conditions at last.
2. according to heptanone-3 synthesis technique of claim 1, it is characterized in that: described alkaline condensation is meant the sodium hydroxide condensation with 1%.
3. according to heptanone-3 synthesis technique of claim 1, it is characterized in that: described oxidation is meant uses the Peracetic Acid oxidation in the presence of acetic acid or sodium-acetate.
4. according to heptanone-3 synthesis technique of claim 1, it is characterized in that: described acidic conditions hydrolysis is to use sulphuric acid hydrolysis.
5. according to heptanone-3 synthesis technique of claim 1, it is characterized in that 30 ℃～40 ℃ of the temperature of alkaline condensation, oxidizing temperature are 15 ℃～30 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01142695 CN1216025C (en) | 2001-12-18 | 2001-12-18 | Synthesis of heptanone-3 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01142695 CN1216025C (en) | 2001-12-18 | 2001-12-18 | Synthesis of heptanone-3 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1426991A true CN1426991A (en) | 2003-07-02 |
| CN1216025C CN1216025C (en) | 2005-08-24 |
Family
ID=4676924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01142695 Expired - Lifetime CN1216025C (en) | 2001-12-18 | 2001-12-18 | Synthesis of heptanone-3 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1216025C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101811948A (en) * | 2010-03-22 | 2010-08-25 | 滕州市悟通香料有限责任公司 | Method for synthesizing pentanone-2 through Bayer-Vlieger oxidation reaction |
| CN106431932A (en) * | 2015-08-04 | 2017-02-22 | 江苏圣奥化学科技有限公司 | Synthesis method of N-2-ethylhexyl-N'-phenyl p-phenylenediamine |
-
2001
- 2001-12-18 CN CN 01142695 patent/CN1216025C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101811948A (en) * | 2010-03-22 | 2010-08-25 | 滕州市悟通香料有限责任公司 | Method for synthesizing pentanone-2 through Bayer-Vlieger oxidation reaction |
| CN106431932A (en) * | 2015-08-04 | 2017-02-22 | 江苏圣奥化学科技有限公司 | Synthesis method of N-2-ethylhexyl-N'-phenyl p-phenylenediamine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1216025C (en) | 2005-08-24 |
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Granted publication date: 20050824 |