CN103408406B - A kind of preparation method of eugenol methyl ether - Google Patents
A kind of preparation method of eugenol methyl ether Download PDFInfo
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- ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 51
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims abstract description 26
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000005770 Eugenol Substances 0.000 claims abstract description 23
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229960002217 eugenol Drugs 0.000 claims abstract description 23
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- 150000005451 methyl sulfates Chemical class 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 240000006497 Dianthus caryophyllus Species 0.000 description 2
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 Eugenol sodium salt Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 240000002022 Anthriscus cerefolium Species 0.000 description 1
- 235000007258 Anthriscus cerefolium Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000111489 Gardenia augusta Species 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000212322 Levisticum officinale Species 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 244000014047 Polianthes tuberosa Species 0.000 description 1
- 235000016067 Polianthes tuberosa Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241001092459 Rubus Species 0.000 description 1
- 235000017276 Salvia Nutrition 0.000 description 1
- 240000007164 Salvia officinalis Species 0.000 description 1
- 241000775848 Syringa oblata Species 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000001645 levisticum officinale Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940116837 methyleugenol Drugs 0.000 description 1
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention belongs to organic synthesis field, particularly a kind of preparation method of eugenol methyl ether, comprise the following steps: appropriate sodium hydroxide solution adds in reactor by a., under the condition stirred, drip appropriate Eugenol; B. keep stirring, temperature of reaction controls at 20 ~ 30 DEG C, slowly drips excessive methyl-sulfate; C., after dripping off, after continuing stirring reaction 1h, raised temperature to 40 DEG C ~ 50 DEG C of reaction 1h decompose methyl-sulfates; D. separatory, namely organic phase underpressure distillation obtains product; The present invention can solve preparation method's yield of existing eugenol methyl ether and cost can not be taken into account, and the problem that product purity is lower, has the advantage that yield is high, product purity is high and cost is low.
Description
Technical field
The invention belongs to organic synthesis field, particularly a kind of preparation method of eugenol methyl ether.
Background technology
Eugenol methyl ether has another name called methyl eugenol, English name (Eugenol methyl ether), and chemical name is 1,2-dimethoxy-4 '-(2-propenyl) benzene, and molecular formula is C11H14O2, and structural formula is:
Molecular weight is: 178.23, boiling point: 244-245 DEG C, relative density: 1.032-1.036, specific refractory power: 1.532-1.536, flash-point: 99 DEG C.Colourless to micro-yellow liquid, water-soluble hardly, be dissolved in 70% ethanol with 1: 2.Naturally to be present in the alpine plants such as Rubus fruticocus, pepper, levisticum officinale, chervil, lemon balm.
Eugenol methyl ether has the fresh and sweet pungent fragrance of cloves-fennel, and like Dianthus caryophyllus L. breath, fragrance is more thoroughly sent out and lastingly, has the pungent fragrance of the gentleness of tea sample, can be used as the promoting or transferring agent of cloves fragrance; Gentle inside information is produced in floral type or medicinal herbs odor type or east odor type, can on a small quantity in the odor types such as rose, Dianthus caryophyllus L., Yilan, Syringa oblata Lindl., cape jasmine, jacinthe, white orchid, Acacia, Tuberose, Salvia Sclare L., lavandula angustifolia, the bright nurse of bay, men's Gu Long.China GB 2760-96 is defined as the food spices allowing to use, and is mainly used in preparation mixed type spice, provides ginger sample fragrance; Because volatility is low, be applicable to bakery product and tobacco.In addition, eugenol methyl ether can also as the attractive substance of multiple trypetid adult; In medical science, have obvious antibechic, eliminate the phlegm, calm, analgesic activity; Also can as the reaction raw materials of synthesis veratrole.
The preparation method of existing eugenol methyl ether has following several:
1. adopt salt of wormwood as acid binding agent, by Eugenol and methyl iodide back flow reaction in acetone, the employing of the method methylating reagent be methyl iodide costly, and this long reaction time, therefore production cost is higher;
2. adopt methyl-sulfate as methylating reagent (Indian Journal of Chemistry, Section B:Organic Chemistry Including Medicinal Chemistry, 27 (4), 308-310,1988), Eugenol, methyl-sulfate, salt of wormwood are reacted in acetone, the method needs to use a large amount of acetone and makees solvent, and be unfavorable for environmental protection, the salt of wormwood price of employing is also higher, and yield is lower, only have 76%;
3. Chinese patent (CN 102351663 A) discloses a kind of synthetic method of eugenol methyl ether, with Eugenol and methylcarbonate (DMC) for raw material, under base catalysis, prepares eugenol methyl ether by the liquid and solid phase reaction adding pressure.Although the yield of this synthetic method increases, generally higher than 90%, its reaction must be carried out under High Temperature High Pressure (0.2-0.3MPa, 120-240 DEG C), and the reaction times is longer, and comparatively large to energy consumption, production cost is higher.
In the prior art method, the problem that also existence one is maximum is exactly: the purity of obtained eugenol methyl ether is on the low side, generally all lower than 99%, needs to purify further.
Summary of the invention
Technical problem to be solved by this invention is: preparation method's yield of existing eugenol methyl ether and cost can not be taken into account, and product purity is lower, and in production process in a large number with an organic solvent.
In order to solve the problems of the technologies described above, the invention provides following technical scheme:
A preparation method for eugenol methyl ether, comprises the following steps:
A. appropriate sodium hydroxide solution is added in reactor, under the condition stirred, drip appropriate Eugenol;
B. keep stirring, temperature of reaction controls at 20 ~ 30 DEG C, slowly drips excessive methyl-sulfate;
C. after dripping off, after continuing stirring reaction 1h, after raised temperature to 40 DEG C ~ 50 DEG C of reaction 1h decompose methyl-sulfates;
D. separatory, namely organic phase underpressure distillation obtains product.
Compared with prior art, the invention has the advantages that:
1. surprisingly, the product yield obtained by method of the present invention is higher than 90%, and when without any further purification step, product purity is higher than 99%;
The present invention adopts sodium hydroxide to replace salt of wormwood, the sodium salt that sodium hydroxide is easier and Eugenol reaction generation nucleophilicity is strong, and this sodium salt and methyl-sulfate more easily react, and are conducive to the raising of yield;
Because methyl-sulfate is when temperature is higher than 40 DEG C, be just very easy to hydrolysis, temperature of reaction of the present invention is lower than 30 DEG C, and the methyl-sulfate not facile hydrolysis of instillation, eliminates because dimethyl sulfate Ester hydrolysis is on the impact of yield, be conducive to the raising of yield;
2. adopt preparation method of the present invention to save production cost:
(1) the present invention only needs the water in sodium hydroxide solution to do reaction solvent, relative to acetone as solvent of the prior art, and not only environmental protection but also can save production cost;
(2) without the need to using expensive methyl iodide, and whole reaction is carried out under low-temperature atmosphere-pressure, relative to high-temperature high-voltage reaction of the prior art, can reduce energy consumption, cost-saving;
(3) methyl-sulfate that interpolation of the present invention is excessive, mainly because reactant in a kind of excessive be conducive to react forward carry out, methyl-sulfate price lower than Eugenol, by its excessive be more conducive to cost-saving.
Preferably, the rate of addition of the methyl-sulfate in step b is no more than 30 DEG C to make temperature of reaction.
This is mainly thermopositive reaction due to this reaction, and the too fast meeting of methyl-sulfate rate of addition causes temperature of reaction to increase suddenly, is unfavorable for that temperature controls.
Preferably, the mol ratio of described sodium hydroxide and Eugenol is: 1.0 ~ 2.0:1.0.
Further, the mol ratio of described alkali and Eugenol is: 1.2 ~ 1.4:1.0.
Excessive sodium hydroxide can make Eugenol change into Eugenol sodium salt completely, is conducive to the raising of productive rate.
Further, the mol ratio of described methyl-sulfate and Eugenol is: 1.2 ~ 1.4:1.0.
Preferably, the mol ratio of described methyl-sulfate and Eugenol is: 1.0 ~ 2.0:1.0.
It is more complete that excessive methyl-sulfate can make Eugenol sodium salt transform, and is conducive to the raising of productive rate, and excessively can cause the waste of raw material and the raising of cost too much, and this ratio provided by the invention is optimum range.
Preferably, the concentration of described sodium hydroxide solution is 8%-10%.
Prove by experiment, naoh concentration is too high, when reacting, easily has solid to separate out, and be unfavorable for the carrying out reacted, concentration is too low, and the volume of the solution reacted can be caused excessive, and reaction density reduces, and be unfavorable for the carrying out reacted, 8%-10% is optimal concentration.
Accompanying drawing explanation
Fig. 1 is the gas phase spectrogram of the product of enforcement 1 of the present invention;
Fig. 2 is the gas phase spectrogram of the product of enforcement 2 of the present invention;
Fig. 3 is the gas phase spectrogram of the product of enforcement 3 of the present invention;
Fig. 4 is the gas phase spectrogram of the product of enforcement 4 of the present invention.
Embodiment
embodiment 1
A preparation method for eugenol methyl ether, comprises the following steps:
A. 8.4g sodium hydroxide and 75g water be made into the alkali lye of about 10% concentration and add in reactor, stirring lower instillation 24.6g Eugenol;
B. temperature of reaction controls at 20 DEG C, and slowly drip 22.8g methyl-sulfate under high degree of agitation, about 1h drips off;
C., after dripping off, after continuing stirring reaction 1h, raised temperature to a 40 DEG C reaction 1h decomposes methyl-sulfate;
D. separatory, namely organic phase underpressure distillation obtains product.
Product is colourless transparent liquid 24.87g, yield 93.0%, as shown in Figure 1, and GC purity 99.53%.
embodiment 2
A preparation method for eugenol methyl ether, comprises the following steps:
A. 9.6g sodium hydroxide and 90g water be made into the alkali lye of about 10% concentration and add in reactor, stirring lower instillation 24.6g Eugenol;
B. temperature of reaction controls at 20 DEG C, and slowly drip 22.8g methyl-sulfate under high degree of agitation, about 1h drips off;
C., after dripping off, after continuing stirring reaction 1h, raised temperature to a 40 DEG C reaction 1h decomposes methyl-sulfate;
D. separatory, namely organic phase underpressure distillation obtains product.
Product is colourless transparent liquid 25.37g, yield 94.9%, as shown in Figure 2, and GC purity 99.53%.
embodiment 3
A preparation method for eugenol methyl ether, comprises the following steps:
A. 16.8g sodium hydroxide and 150g water be made into the alkali lye of about 10% concentration and add in reactor, stirring lower instillation 49.2g Eugenol;
B. temperature of reaction controls at 20 DEG C, and slowly drip 45.6g methyl-sulfate under high degree of agitation, about 1.5h drips off;
C., after dripping off, after continuing stirring reaction 1h, raised temperature to a 50 DEG C reaction 1h decomposes methyl-sulfate;
D. separatory, namely organic phase underpressure distillation obtains product.
Product is colourless transparent liquid 49.1g, yield 91.8%, as shown in Figure 3, and GC purity 99.45%.
embodiment 4
A preparation method for eugenol methyl ether, comprises the following steps:
A. 8.4g sodium hydroxide and 75g water be made into the alkali lye of about 10% concentration and add in reactor, stirring lower instillation 24.6g Eugenol;
B. temperature of reaction controls at 20 DEG C, and slowly drip 21.6g methyl-sulfate under high degree of agitation, about 1h drips off;
C., after dripping off, after continuing stirring reaction 1h, raised temperature to a 50 DEG C reaction 1h decomposes methyl-sulfate;
D. separatory, namely organic phase underpressure distillation obtains product.
Product is colourless transparent liquid 24.30g, yield 90.89%, as shown in Figure 4, and GC purity 99.34%.
Can be proved by above-mentioned experiment, the product of method synthesis of the present invention can have the advantage of high yield, high purity and low cost simultaneously, and the method reaction conditions is gentle, is more suitable for industrial production.
Above-described is only the preferred embodiment of the present invention; should be understood that; for a person skilled in the art; under the prerequisite not departing from structure of the present invention; some distortion and improvement can also be made; these also should be considered as protection scope of the present invention, and these all can not affect effect of the invention process and practical applicability.
Claims (7)
1. a preparation method for eugenol methyl ether, is characterized in that, comprises the following steps:
A. appropriate sodium hydroxide solution is added in reactor, under the condition stirred, drip appropriate Eugenol;
B. keep stirring, temperature of reaction controls at 20 ~ 30 DEG C, slowly drips excessive methyl-sulfate;
C., after dripping off, after continuing stirring reaction 1h, raised temperature to 40 DEG C ~ 50 DEG C of reaction 1h decompose methyl-sulfates;
D. separatory, namely organic phase underpressure distillation obtains product.
2. the preparation method of eugenol methyl ether as claimed in claim 1, it is characterized in that, the mol ratio of described alkali and Eugenol is: 1.0 ~ 2.0:1.0.
3. the preparation method of eugenol methyl ether as claimed in claim 1, it is characterized in that, the mol ratio of described methyl-sulfate and Eugenol is: 1.0 ~ 2.0:1.0.
4. the preparation method of eugenol methyl ether as claimed in claim 1, it is characterized in that, the methyl-sulfate rate of addition in step b is no more than 30 DEG C to make temperature of reaction.
5. the preparation method of eugenol methyl ether as claimed in claim 1, it is characterized in that, the concentration of described sodium hydroxide solution is 8%-10%.
6. the preparation method of eugenol methyl ether as claimed in claim 2, it is characterized in that, the mol ratio of described alkali and Eugenol is: 1.2 ~ 1.4:1.0.
7. the preparation method of eugenol methyl ether as claimed in claim 3, it is characterized in that, the mol ratio of described methyl-sulfate and Eugenol is: 1.2 ~ 1.4:1.0.
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Citations (1)
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|---|---|---|---|---|
| CN102351663A (en) * | 2011-09-29 | 2012-02-15 | 南京林业大学 | Synthesis method of eugenol methyl ether |
Non-Patent Citations (2)
| Title |
|---|
| "Synthesis and spectral characterization of some complexes of platinum(II) containing η2-methyleugenol;Tran Thi Da et al;《Polyhedron》;20070321;第26卷;第3271–3276页 * |
| A GUNASEKARAN et al.syntheses of (±)-Deoxyschizandrin the Lignan, 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane.《Indian Journal of Chemistry》.1988,第27B卷(第4期),第308-310页. * |
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