CN102558002A - Preparation method of essence with jasmine fragrance - Google Patents
Preparation method of essence with jasmine fragrance Download PDFInfo
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- CN102558002A CN102558002A CN2011104427233A CN201110442723A CN102558002A CN 102558002 A CN102558002 A CN 102558002A CN 2011104427233 A CN2011104427233 A CN 2011104427233A CN 201110442723 A CN201110442723 A CN 201110442723A CN 102558002 A CN102558002 A CN 102558002A
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- 235000010254 Jasminum officinale Nutrition 0.000 title claims abstract description 26
- 239000003205 fragrance Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 240000005385 Jasminum sambac Species 0.000 title description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 241000207840 Jasminum Species 0.000 claims abstract 9
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 claims description 15
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 claims description 15
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 238000013019 agitation Methods 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 125000005323 thioketone group Chemical group 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 241000468081 Citrus bergamia Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 244000024873 Mentha crispa Species 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 244000223072 Narcissus jonquilla Species 0.000 description 1
- 235000013862 Narcissus jonquilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000170793 Phalaris canariensis Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001387 apium graveolens Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
The invention relates to a preparation method of an essence with jasmine fragrance. The method comprises the following steps of: mixing jasmine with a Lawson reagent under condensing and stirring actions; performing microwave irradiation; and extracting and concentrating to obtain the essence with jasmine fragrance. The method is applied to a sulfur ketonization reaction under the action of microwave assistance, and jasmine is taken as a raw material, so that a jasmine essence with typical softer jasmine fragrance is synthesized. The essence contains high-concentration 3-methyl-2-(2-pentenyl)-2-cyclopentene-1-thioketone. The preparation method disclosed by the invention has the advantages of readily-available raw materials, low cost, hybrid reaction and easiness for operating.
Description
[technical field]
The invention belongs to the spices preparation field.More specifically, the present invention relates to a kind of preparation method with essence of jasmine fragrance, and the essence with jasmine fragrance that obtains according to said preparation method.
[background technology]
The thioketone that comprises carbonyl more and more receives publicity; Because of it has huge using value at biology and commercial party mask; Can be used as the precursor of many organic cpds when synthetic, for example the product after ketone, flavones, lactone, aminocompound and the ester class thiocarbonylization.Usually utilize the Sauerstoffatom on chemical oxygen-sulphur exchange process replacement carbonyl compound; Make solvent with aromatic hydrocarbon; Benzene,toluene,xylene etc. for example, but should reaction required time longer, also to add excessive thioated reagent usually; And follow a lot of side reactions, most of energy consumptions are big, long reaction time and output is lower.These conversion processes are helped realize by several kinds of reactants usually, the alkaline condition that for example has thiophosphoric anhydride to exist, the acidic conditions that hydrogen sulfide exists; Thioacetic acid etc.; But the most effectively thioketones reagent is 2,4-disulphide, promptly well-known lawesson reagent.Usually utilize sulphur atom to replace the excessive lawesson reagent (0.5-3 equivalent mole) of process need of Sauerstoffatom, long reaction time (2-25h), temperature is higher, and at aromatic hydrocarbon as carrying out under the solvent condition.Otherwise these reagent can produce a lot of side reactions.
With traditional heating reacting phase ratio, the organic synthesis under the microwave radiation has advantages such as speed of response is fast, productive rate is high, side reaction is few, easy purification of products, can also save energy.Discover that microwave helps the thioketones reaction.The applied microwave irradiation can help many organic syntheses, has become popular method at present, and most of compound experiment proves that microwave-assisted can improve productive rate greatly, and environmental pollution is little, and energy consumption is low, and the reaction times shortens.
The present invention utilizes microwave-assisted to be used for the thioketones reaction; ((Z)-3-methyl-2-(pentenyl)-2-cyclopentenes-1-ketone) is raw material with jasmone; Synthetic a kind of smell is softer; Jasmine class essence with typical Flower of Arabian Jasmine fragrance, it contains 3-methyl-2-(the pentenyl)-2-cyclopentenes-1-thioketones of high density.Said essence can be applicable to industries such as food, daily use chemicals.
[summary of the invention]
[technical problem that will solve]
The purpose of this invention is to provide a kind of preparation method with essence of jasmine fragrance.
Another object of the present invention provides the essence with jasmine fragrance for preparing according to said method.
[technical scheme]
The present invention realizes through following technical proposals.
The present invention relates to a kind of preparation method, may further comprise the steps with essence of jasmine fragrance:
(1) jasmone and lawesson reagent are added in Kjeldahl flask with mol ratio at 2: 1, be placed with the magnetic agitation pearl in the said flask, the flask mouth is connected to condensing surface, feeds water of condensation from said condensing surface, under 40-60 ℃, carries out magnetic agitation, the solution that obtains mixing;
(2) use the solution that step (1) is obtained to carry out microwave irradiation, exposure intensity is that 250-350w, irradiation time are 5-7min, leaves standstill 3-6h then, obtains the refrigerative reaction soln;
(3) in the refrigerative reaction soln that step (2) obtains, adding methylene dichloride extracts; Addition is 6-10 times with said refrigerative reaction soln volume; Extraction obtains organic phase, with said organic phase underpressure distillation, until the volume of organic phase be said jasmone volume 1.4-1.6 doubly; Described liquid concentrator separates with column chromatography again, obtains said essence with jasmine fragrance.
According to preferred embodiment a kind of, in the step (1), the rotating speed of magnetic agitation is 200-300rpm, and churning time is 5-60min.
Preferably, in the step (3), underpressure distillation is carried out under 0.8-0.9mpa, 40-50 ℃.
According to preferred embodiment a kind of, in the step (3), the eluant of column chromatography is that mass ratio is 6: 1 the normal hexane and the mixture of ETHYLE ACETATE.
The essence with jasmine fragrance for preparing according to the method for the invention contains 3-methyl-2-(pentenyl)-2-cyclopentenes-1-thioketones of 70-80%.
Below the present invention will be described in more detail.
The present invention relates to a kind of preparation method with essence of jasmine fragrance.Said method comprising the steps of:
(1) 2: 1 jasmone of mol ratio and lawesson reagent are joined in the Kjeldahl flask, be placed with the magnetic agitation pearl in the said flask, the flask mouth is connected to condensing surface; After flask was fixed with iron stand, condensing surface fed water of condensation, and flask is placed on the magnetic stirring apparatus; Open magnetic agitation and heating; Temperature is controlled at 40-60 ℃, and rotating speed is 200-300 rev/min, obtains the solution that mixes thus.
Jasmone is the crude substance that is present in Flower of Arabian Jasmine, pepper, spearmint, jonquil(le), Citrus bergamia, peppermint, tealeaves and multiple the spending.It can be widely used in the floral type daily chemical essence and for it brings a kind of natural floral note, also can be used in the multiple eating essence, like the food flavour of Jasmine tea, strawberry, pineapple and mint aroma.It has stability in application, can be applied on a large scale in perfume, cosmetic bath accessory and the household articles.
Jasmone (Z)-3-methyl-2-(pentenyl)-2-cyclopentenes-1-ketone, it is colourless to weak yellow liquid that outward appearance is, and has the good fragrance of a flower of diffustivity, natural jasmine style, celery seed appearance fragrance.The jasmone that uses among the present invention can be normally used in the art commercially available jasmone product, is for example contained the product of precious auspicious development in science and technology ltd production and sales by Wuhan.
Lawesson reagent (Lawesson reagent, LR) is a kind of oxygen sulphur exchange reagent, and its modal application is producing of organosulfur compound.Lawesson reagent can be bought acquisition, for example the lawesson reagent product of the good occasion chemical industry ltd in Shanghai sale.
The usage quantity of jasmone and lawesson reagent is mol ratio 2: 1.
The mixed Heating temperature of jasmone and lawesson reagent is extremely important, requires in the present invention to be controlled at 40-60 ℃, too high or too low for temperaturely is unfavorable for that all reaction carries out, too high can reaction product through a large amount of the scattering and disappearing of volatilizing, cross low then can the reaction needs plenty of time.
(2) microwave with intensity 250-350w shines 5-7min to the solution that mixes that step (1) obtains, and stops microwave irradiation then, continues reaction 3-6h again, stopped reaction then, and reaction soln leaves standstill cooling.
The present invention utilizes microwave-assisted to be used for the thioketones reaction.Between infrared and radiowave, wavelength is in the zone of 1mm-1m (frequency 300GHz-300MHz) in electromagnetic spectrum for microwave.And general stuck-at-2.2cm of the microwave wavelength that is used for heating technique (2.45GHz) or 33.3cm (900MHz).The microwave oven of commercial prodn generally adopts 12.2cm as fixed wave length.Microwave is very complicated to the effect of material, and the mechanism for microwave acceleration organic reaction does not have unified saying at present.It is the thermal effect of microwave to the heating of the selectivity of polar organic matter that traditional viewpoint is thought, it is dipole pilot polarization and interfacial polarization dielectric loss and the body internal heating that causes in microwave field that leans on medium.
In the present invention, microwave intensity is chosen in 250-350w, and the microwave oven of use is a commercially available microwave oven commonly used in the art, Glanz G80F20CN2L-B8 (SO) type product of for example being sold by Gome.
(3) in the cooled reaction solution that step (2) obtains, add extraction agent; Its addition is 6-10 a times of said cooled reaction solution volume; Extraction obtains organic phase, under pressure 0.8-0.9mpa, 40 ℃ of conditions of temperature, adopts underpressure distillation that organic phase is concentrated then, is concentrated into 1.5 times of jasmone volume; Described liquid concentrator separates with column chromatography again, obtains the essence with jasmine fragrance of the present invention.
The extraction agent that in this step, uses is the solvent that is selected from methylene dichloride, preferably uses methylene dichloride.The usage quantity of said extraction agent is 8 times of said cooled reaction solution volume.
In the present invention, the eluant of column chromatography is that mass ratio is 6: 1 the normal hexane and the mixture of ETHYLE ACETATE.The final product that obtains after the elution is the essence with jasmine fragrance of the present invention.
Utilize column chromatography that said final product is analyzed, the result shows the compound that wherein contains concentration 75%, and compound detects through NMR spectrum, and said compound is 3-methyl-2-(pentenyl)-2-cyclopentenes-1-thioketones.
[beneficial effect]
The present invention compared with prior art has the following advantages:
The present invention utilizes microwave-assisted to be used for the thioketones reaction, is raw material with the jasmone, and it is softer to have synthesized a kind of smell, has the jasmine class essence of typical Flower of Arabian Jasmine fragrance, and it contains 3-methyl-2-(the pentenyl)-2-cyclopentenes-1-thioketones of high density.
Preparing method of the present invention has that raw material is easy to get, cost is low, reaction mixes, advantage simple to operate.
[embodiment]
Through embodiment the present invention is further specified below.
Embodiment 1
(1) 0.2mol jasmone and 0.1mol lawesson reagent are joined in the Kjeldahl flask, be placed with the magnetic agitation pearl in the said flask, the flask mouth is connected to condensing surface; After flask was fixed with iron stand, condensing surface fed water of condensation, and flask is placed on the magnetic stirring apparatus; Open magnetic agitation and heating; Temperature is controlled at 40 ℃, and rotating speed is 300 rev/mins, obtains the solution that 65mL mixes thus;
(2) microwave with intensity 250w shines 7min to the 65ml solution that step (1) obtains, and stops microwave irradiation then, continues reaction 3h again, stopped reaction then, and reaction soln leaves standstill cooling;
(3) in the cooled reaction solution that step (2) obtains, add the 200ml methylene dichloride as extraction agent; Extraction obtains the 260ml organic phase, under pressure 0.9mpa, 40 ℃ of conditions of temperature, adopts underpressure distillation that organic phase is concentrated then, is concentrated into 98mL; Described liquid concentrator separates with column chromatography again; Eluant is 300mL normal hexane and 50mL ETHYLE ACETATE, obtains the 55mL extracting solution, is the essence with jasmine fragrance of the present invention.Utilize column chromatography that said final product is analyzed, the result shows the compound that wherein contains concentration 75%, and compound detects through NMR spectrum, and said compound is 3-methyl-2-(pentenyl)-2-cyclopentenes-1-thioketones.
Claims (5)
1. preparation method with essence of jasmine fragrance is characterized in that said method comprising the steps of:
(1) jasmone and lawesson reagent are added in Kjeldahl flask with mol ratio at 2: 1, be placed with the magnetic agitation pearl in the said flask, the flask mouth is connected to condensing surface, feeds water of condensation from said condensing surface, under 40-60 ℃, carries out magnetic agitation, the solution that obtains mixing;
(2) use the solution that step (1) is obtained to carry out microwave irradiation, exposure intensity is that 250-350w, irradiation time are 5-7min, leaves standstill 3-6h then, obtains the refrigerative reaction soln;
(3) in the refrigerative reaction soln that step (2) obtains, adding methylene dichloride extracts; Addition is 6-10 times with said refrigerative reaction soln volume; Extraction obtains organic phase, with said organic phase underpressure distillation, until the volume of organic phase be said jasmone volume 1.4-1.6 doubly; Described liquid concentrator separates with column chromatography again, obtains said essence with jasmine fragrance.
2. method according to claim 1 is characterized in that in the step (1), the rotating speed of magnetic agitation is 200-300rpm, and churning time is 5-60min.
3. method according to claim 1 is characterized in that in the step (3), and underpressure distillation is carried out under 0.8-0.9mpa, 40-50 ℃.
4. method according to claim 1 is characterized in that in the step (3), and the eluant of column chromatography is that mass ratio is 6: 1 the normal hexane and the mixture of ETHYLE ACETATE.
5. the essence with jasmine fragrance for preparing according to the described method of each claim among the claim 1-4 is characterized in that said essence contains 3-methyl-2-(pentenyl) of 70-80%-2-cyclopentenes-1-thioketones.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104427233A CN102558002A (en) | 2011-12-26 | 2011-12-26 | Preparation method of essence with jasmine fragrance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104427233A CN102558002A (en) | 2011-12-26 | 2011-12-26 | Preparation method of essence with jasmine fragrance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102558002A true CN102558002A (en) | 2012-07-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011104427233A Pending CN102558002A (en) | 2011-12-26 | 2011-12-26 | Preparation method of essence with jasmine fragrance |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102558002A (en) |
-
2011
- 2011-12-26 CN CN2011104427233A patent/CN102558002A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| 《Tetrahedron Letters》 20031231 Jean-Jacques Filippi et al. Solvent-free thionation of Upsilon-lactones under microwave irradiation 6647-6650 1-5 第44卷, * |
| ANNA PAWEŁCZYK ET AL.: "Synthesis of fragrant heterocyclic thioketo analogues of jasmone under microwave conditions", 《FLAVOUR AND FRAGRANCE JOURNAL》 * |
| JEAN-JACQUES FILIPPI ET AL.: "Solvent-free thionation of Υ-lactones under microwave irradiation", 《TETRAHEDRON LETTERS》 * |
| 陈坚: "一种新型的硫化试剂-Lawesson试剂", 《化学试剂》 * |
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Application publication date: 20120711 |