CN102010305A - Method for preparing 2-methoxyl-4-vinyl phenol - Google Patents
Method for preparing 2-methoxyl-4-vinyl phenol Download PDFInfo
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- CN102010305A CN102010305A CN2010102728053A CN201010272805A CN102010305A CN 102010305 A CN102010305 A CN 102010305A CN 2010102728053 A CN2010102728053 A CN 2010102728053A CN 201010272805 A CN201010272805 A CN 201010272805A CN 102010305 A CN102010305 A CN 102010305A
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- methoxyl group
- extraction solvent
- vinylphenol
- distillation
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Abstract
The invention discloses a method for preparing 2-methoxyl-4-vinyl phenol. The method comprises the following steps of: reaction, distillation under reduced pressure, dissolution and water-washing distillation and high vacuum distillation. Therefore, the production process is simple; the method is convenient to operate; the product yield can be improved; the production cost can be reduced; the process conditions can be improved; and a high-purity product can be prepared. The 2-methoxyl-4-vinyl phenol particularly serves as a spice in industries of daily chemicals, medicaments, essence synthesis and the like.
Description
Technical field:
This invention relates to a kind of preparation method of spices, the preparation method of particularly a kind of 2-methoxyl group-4-vinylphenol.
Background technology:
2-methoxyl group-4-vinylphenol (2-Methoxy-4-vinylphenol) has another name called 4-vinyl guaiacol (4-Vinylguaiacol is called for short 4VG), molecular formula C
9H
10O
2, molecular weight 150, density 1.1 * 10
3Kg/m
3, 26 ℃～29 ℃ of fusing points, 100 ℃/667Pa of boiling point, it is colourless or the pale yellow oily liquid body, be fermentation fragrance, bake perfume (or spice), the nut flavor, fruital, and hot fragrant, sweet taste slightly, the breath of little band phenol is a main flavour ingredient of food taste such as decision drinks, soy sauce, tealeaves, coffee, cheese and quality, one of rare high-grade spices of industries such as still daily use chemicals, medicine, essence are synthetic simultaneously, its natural product mainly are present in the volatile matter of corn alcohol fermentation.
2-methoxyl group-4-vinylphenol is a high-grade spices relatively more commonly used at present, the wide mass-producing mass production that remains of market outlook, present domestic this product of manufacturer production that also do not have.
Summary of the invention:
Purpose of the present invention is exactly that a kind of preparation method who improves product yield, reduces production costs and improve the 2-methoxyl group-4-vinylphenol of processing condition, the highly purified product of preparation will be provided.
The object of the present invention is achieved like this: the preparation method of a kind of 2-methoxyl group-4-vinylphenol is characterized in that it has following steps to finish:
1) reaction: use 3-methoxyl group-4-hydroxy benzaldehyde and propanedioic acid under catalyst action, generation is reacted in heating in organic solvent, and Heating temperature is 50-120 ℃, and be 6.5-10 hour heat-up time; Its reaction equation is:
2), underpressure distillation: the soln using rotary film evaporator distillation of reaction is gone out solvent, obtain thick product;
3), dissolving washing distillation: thick product is dissolved with extraction solvent, transfer to then in the reaction washing still, add pickling between the PH=3-5, divide water-yielding stratum and extraction solvent layer, the extraction solvent layer is washed to PH=4-5 with saturated common salt, water layer extracts with extraction solvent, and water and saturated common salt are washed to PH=4-5 again after the merging; Merge two portions extraction solvent and add siccative, steam extraction solvent,, get smart thick product the extraction solvent evaporate to dryness with thin-film evaporator;
4), molecular distillation: the smart thick product that obtains is to distill under the 0.1-0.3mmHg post to obtain high purity product through the molecular distillation device at pressure.
3-methoxyl group of the present invention-4-hydroxy benzaldehyde: propanedioic acid: the mol ratio of catalyzer is: 1: 1.5-2: 0.3-1.
Catalyzer of the present invention is in triethylamine, diethylamine, piperidines, ammonia, carboxylate salt, the sodium hydroxide one or more.
Solvent of the present invention is one or more in benzene, toluene, piperidines, hexanaphthene, pyridine, mixed benzene, methylene dichloride, the trichloromethane.
Extraction solvent of the present invention is anhydrous diethyl ether, ethyl acetate, methylene dichloride, 1, a kind of in 2-ethylene dichloride, the hexanaphthene.
Acid of the present invention is a kind of in concentrated hydrochloric acid, sulfuric acid, phosphoric acid, the acetate.
Siccative of the present invention is a kind of in anhydrous magnesium sulfate, anhydrous sodium sulphate, the Calcium Chloride Powder Anhydrous.
The present invention compared with prior art has the following advantages:
Reaction, underpressure distillation, dissolving washing are distilled, the method for molecular distillation owing to adopted, thereby:
1, production technique is simple, and is easy to operate;
2, can improve product yield, reduce production costs and improve processing condition;
3, can prepare highly purified product.
Embodiment:
Embodiment 1:
In the reactor of 500L, add Vanillin 77Kg, propanedioic acid 131.6Kg, solvent 260L, under agitation add catalyzer 12Kg, heat, solvent is a toluene, and catalyzer is a triethylamine, at first keep warm in the reactor at 50 ℃, be 5.5 hours heat-up time, then the temperature in the reactor is raised to 120 ℃ of reactions 3.5 hours, and reaction finishes; Underpressure distillation utilizes the rotary film evaporator distillation to go out the 170L solvent, obtains thick product; Thick product dissolves with the 250L extraction solvent, and extraction solvent is an ethyl acetate, transfers in the reaction washing still, adds 1N hydrochloric acid and is washed till PH=3, divides water-yielding stratum and ethyl acetate layer; Ethyl acetate layer is washed to PH=4 with saturated common salt, and water layer carries out 4 extractions with ethyl acetate, merges back water and saturated common salt and is washed to PH=4; Merge two portions ethyl acetate and add anhydrous magnesium sulfate drying, ethyl acetate layer steams ethyl acetate with thin-film evaporator, with the ethyl acetate evaporate to dryness, get smart thick product 74Kg, under the 0.1mmHg post, obtain high purity product 53.33Kg, yield 70.19%, content 99.12% through molecular distillation.
Embodiment 2:
In the reactor of 500L, add Vanillin 77Kg, propanedioic acid 131.6Kg, solvent 260L, under agitation add catalyzer 12Kg, heat, solvent is benzene and pyridine mixtures, and catalyzer is a piperidines, at first keep warm in the reactor at 60 ℃, be 5 hours heat-up time, then the temperature in the reactor is raised to 115 ℃ of reactions 4 hours, and reaction finishes; Underpressure distillation utilizes the rotary film evaporator distillation to go out the 170L solvent, obtains thick product; Thick product dissolves with the 250L extraction solvent, and extraction solvent is an anhydrous diethyl ether, transfers in the reaction washing still, adds 1N hydrochloric acid and is washed till PH=4, divides water-yielding stratum and anhydrous diethyl ether layer; The anhydrous diethyl ether layer is washed to PH=4 with saturated common salt, and water layer carries out 4 extractions with anhydrous diethyl ether, merges back water and saturated common salt and is washed to PH=4; Merge two portions anhydrous diethyl ether and add anhydrous magnesium sulfate drying, the anhydrous diethyl ether layer steams anhydrous diethyl ether with thin-film evaporator, with the anhydrous diethyl ether evaporate to dryness, get smart thick product 74Kg, under the 0.2mmHg post, obtain high purity product 50.36Kg, yield 66.27%, content 99.11% through molecular distillation.
Embodiment 3:
In the reactor of 500L, add Vanillin 77Kg, propanedioic acid 131.6Kg, solvent 260L, under agitation add catalyzer 12Kg, heat, solvent is a pyridine, and catalyzer is the mixture of triethylamine and ammonia, at first keep warm in the reactor at 65 ℃, be 4.5 hours heat-up time, then the temperature in the reactor is raised to 110 ℃ of reactions 5 hours, and reaction finishes; Underpressure distillation utilizes the rotary film evaporator distillation to go out the 170L solvent, obtains thick product; Thick product dissolves with the 250L extraction solvent, and extraction solvent is 1, and the 2-ethylene dichloride is transferred in the reaction washing still, adds 1N acetate and is washed till PH=5, divides water-yielding stratum and 1,2-ethylene dichloride layer; 1,2-ethylene dichloride layer is washed to PH=5 with saturated common salt, and water layer is with 1, and the 2-ethylene dichloride carries out 4 extractions, merges back water and saturated common salt and is washed to PH=5; Merge two portions 1, the 2-ethylene dichloride adds the Calcium Chloride Powder Anhydrous drying, 1,2-ethylene dichloride layer steams 1 with thin-film evaporator, the 2-ethylene dichloride, with 1,2-ethylene dichloride evaporate to dryness gets smart thick product 74Kg, obtains high purity product 52.26Kg through molecular distillation under the 0.3mmHg post, yield 68.88%, content 99.31%.
Embodiment 4:
In the reactor of 500L, add Vanillin 77Kg, propanedioic acid 131.6Kg, solvent 260L, under agitation add catalyzer 12Kg, heat, solvent is methylene dichloride and pyridine mixtures, and catalyzer is sodium hydroxide and piperidines mixture, at first keep warm in the reactor at 75 ℃, be 3.5 hours heat-up time, then the temperature in the reactor is raised to 117 ℃ of reactions 4 hours, and reaction finishes; Underpressure distillation utilizes the rotary film evaporator distillation to go out the 170L solvent, obtains thick product; Thick product dissolves with the 250L extraction solvent, and extraction solvent is a methylene dichloride, transfers in the reaction washing still, adds 1N sulfuric acid and is washed till PH=4, divides water-yielding stratum and dichloromethane layer; Dichloromethane layer is washed to PH=4 with saturated common salt, and water layer carries out 4 extractions with methylene dichloride, merges back water and saturated common salt and is washed to PH=4; Merge two portions methylene dichloride and add anhydrous sodium sulfate drying, filter, dichloromethane layer steams methylene dichloride with thin-film evaporator, with the methylene dichloride evaporate to dryness, get smart thick product 74Kg, under the 0.1mmHg post, obtain high purity product 52.86Kg, yield 69.56%, content 99.28% through molecular distillation.
Embodiment 5:
In the reactor of 500L, add Vanillin 77Kg, propanedioic acid 131.6Kg, solvent 260L, under agitation add catalyzer 12Kg, heat, solvent is benzene, piperidines and pyridine mixtures, and catalyzer is a triethylamine, at first keep warm in the reactor at 50 ℃, be 5.5 hours heat-up time, then the temperature in the reactor is raised to 120 ℃ of reactions 3.5 hours, and reaction finishes; Underpressure distillation utilizes rotary film evaporator to distill out the 170L solvent, obtains thick product; Thick product dissolves with the 250L extraction solvent, and extraction solvent is an ethyl acetate, transfers in the reaction washing still, adds 1N hydrochloric acid and is washed till PH=3, divides water-yielding stratum and ethyl acetate layer; Ethyl acetate layer is washed to PH=4 with saturated common salt, and water layer carries out 4 extractions with ethyl acetate, merges back water and saturated common salt and is washed to PH=4; Merge two portions ethyl acetate and add anhydrous magnesium sulfate drying, ethyl acetate layer steams ethyl acetate with thin-film evaporator, with the ethyl acetate evaporate to dryness, get smart thick product 74Kg, under the 0.1mmHg post, obtain high purity product 53.33Kg, yield 70.19%, content 99.12% through molecular distillation.
Claims (7)
1. the preparation method of 2-methoxyl group-4-vinylphenol is characterized in that it has following steps to finish:
1) reaction: use 3-methoxyl group-4-hydroxy benzaldehyde and propanedioic acid under catalyst action, generation is reacted in heating in organic solvent, and Heating temperature is 50-120 ℃, and be 6.5-10 hour heat-up time; Its reaction equation is:
2), underpressure distillation: the soln using rotary film evaporator distillation of reaction is gone out solvent, obtain thick product;
3), dissolving washing distillation: thick product is dissolved with extraction solvent, transfer to then in the reaction washing still, add pickling between the PH=3-5, divide water-yielding stratum and extraction solvent layer, the extraction solvent layer is washed to PH=4-5 with saturated common salt, water layer extracts with extraction solvent, and water and saturated common salt are washed to PH=4-5 again after the merging; Merge two portions extraction solvent and add siccative, steam extraction solvent,, get smart thick product the extraction solvent evaporate to dryness with thin-film evaporator;
4), molecular distillation: the smart thick product that obtains is to distill under the 0.1-0.3mmHg post to obtain high purity product through the molecular distillation device at pressure.
2. the preparation method of 2-methoxyl group according to claim 1-4-vinylphenol, it is characterized in that described 3-methoxyl group-4-hydroxy benzaldehyde: propanedioic acid: the mol ratio of catalyzer is: 1: 1.5-2: 0.3-1.
3. 2-methoxyl group according to claim 1-4-vinylphenol is characterized in that described catalyzer is one or more in triethylamine, diethylamine, piperidines, ammonia, carboxylate salt, the sodium hydroxide.
4. 2-methoxyl group according to claim 1-4-vinylphenol is characterized in that described organic solvent is one or more in benzene, toluene, piperidines, hexanaphthene, pyridine, mixed benzene, methylene dichloride, the trichloromethane.
5. 2-methoxyl group according to claim 1-4-vinylphenol is characterized in that described extraction solvent is anhydrous diethyl ether, ethyl acetate, methylene dichloride, 1, a kind of in 2-ethylene dichloride, the hexanaphthene.
6. 2-methoxyl group according to claim 1-4-vinylphenol is characterized in that described acid is a kind of in concentrated hydrochloric acid, sulfuric acid, phosphoric acid, the acetate.
7. 2-methoxyl group according to claim 1-4-vinylphenol is characterized in that described siccative is a kind of in anhydrous magnesium sulfate, anhydrous sodium sulphate, the Calcium Chloride Powder Anhydrous.
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|---|---|---|---|
| CN2010102728053A CN102010305A (en) | 2010-09-02 | 2010-09-02 | Method for preparing 2-methoxyl-4-vinyl phenol |
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|---|---|---|---|
| CN2010102728053A CN102010305A (en) | 2010-09-02 | 2010-09-02 | Method for preparing 2-methoxyl-4-vinyl phenol |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110790640A (en) * | 2019-10-16 | 2020-02-14 | 安徽理工大学 | Preparation method of 2-methoxy-4-vinylphenol |
| CN111454133A (en) * | 2020-03-31 | 2020-07-28 | 江西恒诚天然香料油有限公司 | Synthesis method of eugenol |
| CN111454132A (en) * | 2020-03-31 | 2020-07-28 | 江西恒诚天然香料油有限公司 | Method for synthesizing eugenol |
| CN117625422A (en) * | 2024-01-26 | 2024-03-01 | 龙牌食品股份有限公司 | Pichia burton strain L9-1 and application thereof |
-
2010
- 2010-09-02 CN CN2010102728053A patent/CN102010305A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110790640A (en) * | 2019-10-16 | 2020-02-14 | 安徽理工大学 | Preparation method of 2-methoxy-4-vinylphenol |
| CN110790640B (en) * | 2019-10-16 | 2023-01-24 | 安徽理工大学 | Preparation method of 2-methoxy-4-vinylphenol |
| CN111454133A (en) * | 2020-03-31 | 2020-07-28 | 江西恒诚天然香料油有限公司 | Synthesis method of eugenol |
| CN111454132A (en) * | 2020-03-31 | 2020-07-28 | 江西恒诚天然香料油有限公司 | Method for synthesizing eugenol |
| CN117625422A (en) * | 2024-01-26 | 2024-03-01 | 龙牌食品股份有限公司 | Pichia burton strain L9-1 and application thereof |
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Application publication date: 20110413 |