CN103408406A - Preparation method of methyl eugenol - Google Patents
Preparation method of methyl eugenol Download PDFInfo
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- CN103408406A CN103408406A CN2013103389731A CN201310338973A CN103408406A CN 103408406 A CN103408406 A CN 103408406A CN 2013103389731 A CN2013103389731 A CN 2013103389731A CN 201310338973 A CN201310338973 A CN 201310338973A CN 103408406 A CN103408406 A CN 103408406A
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- eugenol
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- sulfate
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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 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229940116837 methyleugenol Drugs 0.000 title abstract description 5
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 title abstract description 5
- 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 37
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims abstract description 29
- 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 15
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims description 7
- 230000000630 rising effect Effects 0.000 claims description 6
- 150000005451 methyl sulfates Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 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
- 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
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 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
- 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
- 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
- 230000000881 depressing effect Effects 0.000 description 1
- 230000000694 effects Effects 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
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of organic synthesis and particularly relates to a preparation method of methyl eugenol. The preparation method of the methyl eugenol comprises the following steps: a, adding right amount of sodium hydroxide solution into a reaction kettle, and dripping right amount of eugenol under a stirring condition; b, keeping stirring, controlling the reaction temperature to be 20 to 30 DEG C, slowly dripping excess methyl sulfate; c, after dripping, stirring for 1 h reaction continuously, and increasing the temperature to be 40 DEG C to 50 DEG C for 1 h reaction for resolving the methyl sulfate; d, dividing liquid, carrying out underpressure distillation to organic phases so as to obtain a product. The preparation method provided by the invention solves the problems of incapability of considering the yield and the cost at the same time and low product purity in a conventional preparation method of the methyl eugenol, and has the advantages of high yield, high product purity and low cost.
Description
Technical field
The invention belongs to the preparation method in organic synthesis field, particularly a kind of eugenol methyl ether.
Background technology
Eugenol methyl ether has another name called methyl eugenol, and English name (Eugenol methyl ether), chemical name are 1,2-dimethoxy-4 '-(2-propenyl) benzene, and molecular formula is C11H14O2, and structural formula is:
Molecular weight is: 178.23, and boiling point: 244-245 ℃, relative density: 1.032-1.036, specific refractory power: 1.532-1.536, flash-point: 99 ℃.Colourless to micro-yellow liquid, water-soluble hardly, with 1: 2, be dissolved in 70% ethanol.Natural being present in the high mountain plants such as Rubus fruticocus, pepper, levisticum officinale, chervil, lemon balm.
Eugenol methyl ether has the hot fragrance of fresh and sweet cloves-fennel, and like the Dianthus caryophyllus L. breath, fragrance is more thoroughly sent out and lastingly, the hot fragrance of gentleness of tea sample arranged, and can be used as the promoting or transferring agent of cloves fragrance; In floral type or medicinal herbs odor type or east odor type, produce gentle inside information, can be on a small quantity for 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 and allows the food spices used, and is mainly used in preparing the mixed type spice, and ginger sample fragrance is provided; Because volatility is low, be applicable to bakery product and tobacco.In addition, eugenol methyl ether can also be as the attractive substance of multiple trypetid adult; Obvious antibechic arranged in medical science, eliminate the phlegm, calm, analgesic activity; Also can be used as the reaction raw materials of synthetic veratrole.
The preparation method of existing eugenol methyl ether has following several:
1. adopt salt of wormwood as acid binding agent, the back flow reaction in acetone by Eugenol and methyl iodide, what the method methylating reagent adopted is more expensive methyl iodide, and this long reaction time, so 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 need to be used a large amount of acetone and make solvent, is unfavorable for environmental protection, and 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, take Eugenol and methylcarbonate (DMC) to be raw material, under base catalysis, prepares eugenol methyl ether by adding the liquid and solid phase reaction of depressing.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 ℃), and the reaction times is longer, and larger to energy consumption, production cost is higher.
In the method for prior art, also exist the problem of a maximum to be exactly: the purity of the eugenol methyl ether made is on the low side, generally all lower than 99%, need to further purify.
Summary of the invention
Technical problem to be solved by this invention is: preparation method's yield and the cost of existing eugenol methyl ether 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 kind of preparation method of 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 is controlled at 20～30 ℃, slowly drips excessive methyl-sulfate;
C. after dripping off, after continuing stirring reaction 1h, after rising temperature to 40 ℃～50 ℃ of reaction 1h decompose methyl-sulfate;
D. separatory, the organic phase underpressure distillation namely obtains product.
Compared with prior art, the invention has the advantages that:
1. beat allly be, the product yield obtained by method of the present invention is higher than 90%, and in the situation that do not pass through any additional purification step, product purity is higher than 99%;
The present invention adopts sodium hydroxide to replace salt of wormwood, and more easily and the strong sodium salt of Eugenol reaction generation nucleophilicity, this sodium salt and methyl-sulfate more easily react sodium hydroxide, are conducive to the raising of yield;
Because methyl-sulfate during higher than 40 ℃, just is very easy to hydrolysis in temperature, temperature of reaction of the present invention is lower than 30 ℃, and the methyl-sulfate splashed into is facile hydrolysis not, has eliminated because of the impact of methyl-sulfate hydrolysis on yield, is 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, makes solvent with respect to acetone of the prior art, not only environmental protection but also can save production cost;
(2) without using expensive methyl iodide, and whole reaction carries out under low-temperature atmosphere-pressure, with respect to high-temperature high-voltage reaction of the prior art, can reduce energy consumption, cost-saving;
(3) the excessive methyl-sulfate of interpolation of the present invention, be mainly that the methyl-sulfate price is lower than Eugenol because a kind of excessive forward that is conducive to react in reactant carries out, by its excessive more be conducive to cost-saving.
As preferred version, the rate of addition of the methyl-sulfate in step b is so that temperature of reaction is no more than 30 ℃.
This is mainly because this reaction is thermopositive reaction, and the too fast meeting of methyl-sulfate rate of addition causes temperature of reaction to increase suddenly, is unfavorable for temperature control.
As preferred version, 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 completely the Eugenol sodium salt, 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.
As preferred version, 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 that the Eugenol sodium salt transforms, and is conducive to the raising of productive rate, and excessively can cause too much the waste of raw material and the raising of cost, and this ratio provided by the invention is optimum range.
As preferred version, the concentration of described sodium hydroxide solution is 8%-10%.
Prove by experiment, naoh concentration is too high, when reaction, easily has solid to separate out, and is unfavorable for the carrying out reacted, and concentration is too low, can cause the volume of the solution reacted excessive, and reaction density reduces, and is unfavorable for the carrying out reacted, and 8%-10% is optimal concentration.
The 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 kind of preparation method of eugenol methyl ether comprises the following steps:
A. 8.4g sodium hydroxide and 75g water be made into to the alkali lye of about 10% concentration and add in reactor, under stirring, splashing into the 24.6g Eugenol;
B. temperature of reaction is controlled at 20 ℃, under high degree of agitation, slowly drips the 22.8g methyl-sulfate, and about 1h drips off;
C. after dripping off, after continuing stirring reaction 1h, rising temperature to 40 a ℃ reaction 1h decomposes methyl-sulfate;
D. separatory, the organic phase underpressure distillation namely obtains product.
Product is colourless transparent liquid 24.87g, yield 93.0%, as shown in Figure 1, GC purity 99.53%.
Embodiment 2
A kind of preparation method of eugenol methyl ether comprises the following steps:
A. 9.6g sodium hydroxide and 90g water be made into to the alkali lye of about 10% concentration and add in reactor, under stirring, splashing into the 24.6g Eugenol;
B. temperature of reaction is controlled at 20 ℃, under high degree of agitation, slowly drips the 22.8g methyl-sulfate, and about 1h drips off;
C. after dripping off, after continuing stirring reaction 1h, rising temperature to 40 a ℃ reaction 1h decomposes methyl-sulfate;
D. separatory, the organic phase underpressure distillation namely obtains product.
Product is colourless transparent liquid 25.37g, yield 94.9%, as shown in Figure 2, GC purity 99.53%.
Embodiment 3
A kind of preparation method of eugenol methyl ether comprises the following steps:
A. 16.8g sodium hydroxide and 150g water be made into to the alkali lye of about 10% concentration and add in reactor, under stirring, splashing into the 49.2g Eugenol;
B. temperature of reaction is controlled at 20 ℃, under high degree of agitation, slowly drips the 45.6g methyl-sulfate, and about 1.5h drips off;
C. after dripping off, after continuing stirring reaction 1h, rising temperature to 50 a ℃ reaction 1h decomposes methyl-sulfate;
D. separatory, the organic phase underpressure distillation namely obtains product.
Product is colourless transparent liquid 49.1g, yield 91.8%, as shown in Figure 3, GC purity 99.45%.
Embodiment 4
A kind of preparation method of eugenol methyl ether comprises the following steps:
A. 8.4g sodium hydroxide and 75g water be made into to the alkali lye of about 10% concentration and add in reactor, under stirring, splashing into the 24.6g Eugenol;
B. temperature of reaction is controlled at 20 ℃, under high degree of agitation, slowly drips the 21.6g methyl-sulfate, and about 1h drips off;
C. after dripping off, after continuing stirring reaction 1h, rising temperature to 50 a ℃ reaction 1h decomposes methyl-sulfate;
D. separatory, the organic phase underpressure distillation namely obtains product.
Product is colourless transparent liquid 24.30g, yield 90.89%, as shown in Figure 4, GC purity 99.34%.
By above-mentioned experiment, can prove, the synthetic product of method of the present invention can have high yield, high purity and advantage cheaply simultaneously, and the method reaction conditions gentleness, 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 that does not break away from structure of the present invention; can also make some distortion and improvement; these also should be considered as protection scope of the present invention, and these can not affect effect of the invention process and practical applicability.
Claims (7)
1. the preparation method of an 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 is controlled at 20～30 ℃, slowly drips excessive methyl-sulfate;
C. after dripping off, after continuing stirring reaction 1h, rising temperature to 40 ℃～50 ℃ of reaction 1h decompose methyl-sulfates;
D. separatory, the organic phase underpressure distillation namely obtains product.
2. the preparation method of eugenol methyl ether as claimed in claim 1, 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, 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, is characterized in that, the methyl-sulfate rate of addition in step b is so that temperature of reaction is no more than 30 ℃.
5. the preparation method of eugenol methyl ether as claimed in claim 1, 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, 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, is characterized in that, the mol ratio of described methyl-sulfate and Eugenol is: 1.2～1.4:1.0.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109776282A (en) * | 2019-03-14 | 2019-05-21 | 南京林业大学 | A kind of synthetic method of methylisoeugenol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351663A (en) * | 2011-09-29 | 2012-02-15 | 南京林业大学 | Synthesis method of eugenol methyl ether |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
|---|
| A GUNASEKARAN ET AL: "syntheses of （±）-Deoxyschizandrin & the Lignan， 1,4-Bis（3,4-dimethoxyphenyl）-2,3-dimethylbutane", 《INDIAN JOURNAL OF CHEMISTRY》 * |
| TRAN THI DA ET AL: ""Synthesis and spectral characterization of some complexes of platinum(II) containing η2-methyleugenol", 《POLYHEDRON》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109776282A (en) * | 2019-03-14 | 2019-05-21 | 南京林业大学 | A kind of synthetic method of methylisoeugenol |
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Address after: 401220 No.2, Huanan No.1 Branch Road, Yanjia chemical industry park, Changshou District, Chongqing Patentee after: Chongqing Xinxin Xiangrong Fine Chemical Co.,Ltd. Address before: No.2, Huanan 1st branch road, Yanjia Chemical Industrial Park, Changshou District, Chongqing Patentee before: CHONGQING THRIVE CHEMICAL Co.,Ltd. |