CN117946040A - Method for preparing propiolactone by photochemical fluid reaction equipment - Google Patents
Method for preparing propiolactone by photochemical fluid reaction equipment Download PDFInfo
- Publication number
- CN117946040A CN117946040A CN202311823089.7A CN202311823089A CN117946040A CN 117946040 A CN117946040 A CN 117946040A CN 202311823089 A CN202311823089 A CN 202311823089A CN 117946040 A CN117946040 A CN 117946040A
- Authority
- CN
- China
- Prior art keywords
- propiolactone
- reaction
- preparing
- photochemical fluid
- acrylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 43
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229960000380 propiolactone Drugs 0.000 title claims abstract description 42
- 239000012530 fluid Substances 0.000 title claims abstract description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011941 photocatalyst Substances 0.000 claims abstract description 16
- -1 acrylic ester Chemical class 0.000 claims abstract description 11
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 6
- 150000003254 radicals Chemical class 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 239000003999 initiator Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000002978 peroxides Chemical class 0.000 abstract description 2
- 235000013599 spices Nutrition 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 125000000422 delta-lactone group Chemical group 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- MVOSYKNQRRHGKX-UHFFFAOYSA-N 11-Undecanolactone Chemical compound O=C1CCCCCCCCCCO1 MVOSYKNQRRHGKX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 244000242564 Osmanthus fragrans Species 0.000 description 1
- 235000019083 Osmanthus fragrans Nutrition 0.000 description 1
- 244000288157 Passiflora edulis Species 0.000 description 1
- 235000000370 Passiflora edulis Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention provides a method for preparing propiolactone by photochemical fluid reaction equipment, and relates to the technical field of spice preparation. The method for preparing the propiolactone by using the photochemical fluid reaction equipment adopts acrylic acid or acrylic ester and n-alkyl alcohol as raw materials, and the raw materials react under the irradiation of visible light to generate the propiolactone in the presence of a photocatalyst and an auxiliary agent, and the pure product of the propiolactone is obtained by rectification after the reaction is finished. Wherein the photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN), and the catalyst auxiliary agent is quinuclidine. The method has the advantages of short synthetic route, simple operation, higher yield of the preparation method, contribution to improving productivity, and high yield of 82%, avoids the mass production of waste acid and waste water compared with the traditional process, avoids the heating and high-temperature reaction conditions of the free radical initiator peroxide in the traditional process, and is safe and controllable compared with the traditional process.
Description
Technical Field
The invention relates to the technical field of spice preparation, in particular to a method for preparing propiolactone by photochemical fluid reaction equipment.
Background
Lactones are important organic compounds and intermediates, and have wide application and development prospects in the fields of perfume and essence and drug synthesis, such as the application of the gamma and delta lactones in advanced cosmetics, foods, tobacco industry and the like. Compared with the delta lactone, the delta lactone has obvious advantages in the aspects of fragrance quality and market prospect. Among them, the undecalactone at the position of the propylene is a typical representative compound in lactone type fragrances, and the production process conditions thereof are important subjects of the study of fragrance chemistry.
The undecalactone is colorless to pale yellow viscous liquid, has strong peach fragrance, is commercially called peach aldehyde or tetradecaldehyde, and naturally exists in cream, osmanthus fragrans, peach, apricot, passion fruit and hydrolyzed soybean protein. It is almost insoluble in water, soluble in ethanol and most common organic solvents, and can be widely used in daily use essence and edible essence.
The main synthesis processes of the propiolactone are divided into two types, wherein the first type is to prepare the propiolactone by heating under the catalysis of concentrated sulfuric acid by using olefine acid. The second category is the preparation of propiolactone by free radical addition using acrylic acid or acrylic acid esters and n-alkyl alcohols. Currently, the industrial production mainly adopts two processes according to raw materials.
The propiolactone process is generally poor in yield and very severe in pollution. The first kind of technology needs to use concentrated sulfuric acid to catalyze reaction at 80-100 ℃, and the yield is only about 45%, a large amount of waste acid water is produced, pollution is serious, and the yield is not high. The second type of process has the yield reaching 80%, but the optimal temperature of the reaction is 180 ℃, the molar ratio of the n-alkyl alcohol to the acrylic acid or acrylic ester in the reaction is 6-9, a large amount of n-alkyl alcohol is required to be recovered, and the energy consumption is high.
Visible light catalysis is a research field which is rapidly developed in the last ten years, and compared with the free radical reaction initiated by the traditional free radical initiator, the visible light catalysis has the advantages of mild reaction conditions, good functional group compatibility, no need of using toxic initiator and the like. Therefore, the method for preparing the propiolactone through visible light catalysis has the advantages of convenient operation, high yield and important significance in green and high-efficiency preparation of the propiolactone.
Accordingly, one skilled in the art would be able to provide a method for preparing propiolactone using a photochemical fluid reaction apparatus to solve the above-mentioned problems.
Disclosure of Invention
(One) solving the technical problems
Aiming at the defects of the prior art, the invention provides a method for preparing propiolactone by using photochemical fluid reaction equipment, which takes acrylic acid or acrylic ester and n-alkyl alcohol as raw materials and prepares propiolactone by using a visible light irradiation method under the condition of a photocatalyst. Solves the problems of low yield, high temperature requirement, large environmental pollution and the like in the prior art.
(II)
In order to achieve the above purpose, the invention is realized by the following technical scheme:
a method for preparing propiolactone by photochemical fluid reaction equipment, which takes acrylic acid or acrylic ester and n-alkyl alcohol as raw materials, reacts under the participation of a photocatalyst and an auxiliary agent to generate propiolactone under the irradiation of visible light, and rectifies after the reaction is finished to obtain pure propiolactone. The reaction formula is shown as follows:
wherein the photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN), and the structure is shown as formula (I). The catalyst auxiliary agent is quinuclidine, and the structure is shown as a formula (II).
Formula (I)/> Formula (II)
Preferably, in the reaction, the photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN).
Preferably, in the reaction, the organic solvent is selected from the group consisting of: acetone, acetonitrile, dimethyl sulfoxide, benzotrifluoride, methylene chloride, ethyl acetate, or a combination thereof; acetonitrile is preferred.
Preferably, in the reaction, the molar ratio of the acrylic acid or the acrylic acid ester to the n-alkyl alcohol is 1:1-5.
Preferably, in the reaction, the molar ratio of the photocatalyst to acrylic acid or acrylic ester is 0.005-0.01:1.
Preferably, in the reaction, the molar ratio of the auxiliary quinuclidine to the acrylic acid or the acrylic ester is 0.005-0.025:1.
Preferably, in the reaction, the reaction temperature is 25 ℃.
Preferably, in the reaction, the light source of the reaction is blue light with the wavelength of 440-445 nm.
Preferably, in the reaction, the reaction flow rate is 2-10ml/min.
Preferably, in the reaction, the optofluidic residence time is 30-60min.
(III) beneficial effects
The invention provides a method for preparing propiolactone by photochemical fluid reaction equipment. The beneficial effects are as follows:
1. The method for preparing the propiolactone by using the photochemical fluid reaction equipment has the advantages of short synthetic route, simple operation, higher yield of the preparation method and the like, is beneficial to improving the productivity by 82 percent at most, and avoids a large amount of waste acid and waste water compared with the traditional process.
2. Compared with the traditional method, the method for preparing the propiolactone by using the photochemical fluid reaction equipment has higher specific yield, is beneficial to the industrialization to improve the productivity, and can maximally reach 82 percent.
3. The method for preparing the propiolactone by using the photochemical fluid reaction equipment provided by the invention avoids the addition of free radical initiator peroxide in the traditional process and requires heating and high-temperature reaction conditions, and is safer and more controllable than the traditional process.
4. Compared with the traditional process, the method for preparing the propiolactone by using the photochemical fluid reaction equipment provided by the invention has the advantages that the visible light reaction is carried out under the high-temperature condition, the reaction is milder, and the energy consumption is lower.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. The experimental methods, in which specific conditions are not noted in the following examples, are generally conducted under conventional conditions or under conditions recommended by the manufacturer. Percentages and parts are by weight unless otherwise indicated.
The embodiment of the invention provides a method for preparing propiolactone by photochemical fluid reaction equipment, which takes acrylic acid or acrylic ester and n-alkyl alcohol as raw materials, and under the participation of a photocatalyst and an auxiliary agent, the acrylic acid or acrylic ester and n-alkyl alcohol react under the irradiation of visible light to generate propiolactone, and after the reaction is finished, the propiolactone is rectified to obtain a pure product of the propiolactone. The reaction formula is shown as follows:
wherein the photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN), and the structure is shown as formula (I). The catalyst auxiliary agent is quinuclidine, and the structure is shown as a formula (II).
Formula (I)/>Formula (II)
In another preferred embodiment, the R substituent in the formula is selected from H, CH 3、C2H5、CH2C6H5、t-C4H9.
In another preferred embodiment, the conditions in the reaction formula are selected from any one of 2,3, 4, 5,6, 7, 8.
In another preferred example, the photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN).
In another preferred embodiment, the photocatalyst aid is quinuclidine, i.e., 1-azabicyclo [2.2.2] octane.
In another preferred embodiment, the organic solvent is selected from the group consisting of: acetone, acetonitrile, dimethyl sulfoxide, benzotrifluoride, methylene chloride, ethyl acetate, or a combination thereof; acetonitrile is preferred.
In another preferred embodiment, the molar ratio of acrylic acid or acrylic acid ester to n-alkyl alcohol in the reaction is 1:1-5.
In another preferred embodiment, the molar ratio of photocatalyst to acrylic acid or acrylate is 0.005-0.01:1.
In another preferred embodiment, the molar ratio of the auxiliary quinuclidine to acrylic acid or acrylate is from 0.005 to 0.025:1.
In another preferred embodiment, the reaction temperature is 25 ℃.
In another preferred embodiment, the light source of the reaction is in the blue light, wavelength range 440-445 nm.
In another preferred embodiment, the reaction flow rate is 2-10ml/min.
In another preferred embodiment, the optofluidic residence time is 30-60 minutes.
In another preferred embodiment, the method further comprises: and after the reaction is finished, obtaining a pure product through rectification.
The invention provides another option for replacing the traditional process by adopting photocatalysis to prepare the propiolactone, and the process directly realizes the free radical addition to prepare the lactone by adding a photocatalyst and an auxiliary agent into a system and utilizing visible light illumination.
Examples
A method for preparing propiolactone by an optofluidic reaction apparatus, comprising the steps of:
4CzIPN (3.4 g, 2 mmol), quinuclidine (43.8 g, 0.04 mol), n-octanol 1a (62.9 mL, 0.4 mol) and methyl acrylate (18.1 mL, 0.2 mol) were dissolved in dry acetonitrile (1L) and passed through an optofluidic reactor of a blue LED at a wavelength of 440nm at a flow rate of 2ml/min for a photoreaction time of 30min;
After the completion of the reaction, the product 3 (30.2 g, yield 82%) was obtained by distillation. The reaction formula is shown as follows:
Wherein equiv represents equivalent and mol represents mol.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (10)
1. A method for preparing propiolactone by photochemical fluid reaction equipment is characterized in that acrylic acid or acrylic ester and n-alkyl alcohol are used as raw materials, the raw materials react under the irradiation of visible light under the participation of a photocatalyst and an auxiliary agent to generate the propiolactone, and the pure product of the propiolactone is obtained after the reaction is finished by rectification.
2. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in said reaction, said photocatalyst is 2,4,5, 6-tetra (9-carbazolyl) -isophthalonitrile (4 CzIPN).
3. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in the reaction, the organic solvent is selected from the group consisting of: acetone, acetonitrile, dimethyl sulfoxide, benzotrifluoride, methylene chloride, ethyl acetate, or a combination thereof; acetonitrile is preferred.
4. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in the reaction, the molar ratio of acrylic acid or acrylic acid ester to n-alkyl alcohol is 1:1-5.
5. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in the reaction, the molar ratio of the photocatalyst to acrylic acid or acrylic acid ester is 0.005-0.01:1.
6. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in said reaction, the molar ratio of said auxiliary quinuclidine to acrylic acid or acrylic ester is 0.005-0.025:1.
7. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in said reaction, said reaction temperature is 25 ℃.
8. The method for preparing propiolactone by photochemical fluid reaction equipment as claimed in claim 1, wherein in the reaction, the light source of the reaction is blue light with a wavelength of 440-445 nm.
9. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in the reaction, the reaction flow rate is 2-10ml/min.
10. The method for preparing propiolactone by photochemical fluid reaction apparatus as claimed in claim 1, wherein in said reaction, said optofluidic residence time is 30-60min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311823089.7A CN117946040A (en) | 2023-12-27 | 2023-12-27 | Method for preparing propiolactone by photochemical fluid reaction equipment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311823089.7A CN117946040A (en) | 2023-12-27 | 2023-12-27 | Method for preparing propiolactone by photochemical fluid reaction equipment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117946040A true CN117946040A (en) | 2024-04-30 |
Family
ID=90801019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311823089.7A Pending CN117946040A (en) | 2023-12-27 | 2023-12-27 | Method for preparing propiolactone by photochemical fluid reaction equipment |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117946040A (en) |
-
2023
- 2023-12-27 CN CN202311823089.7A patent/CN117946040A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107652170B (en) | Method for preparing glutaraldehyde by catalyzing cyclopentene to oxidize through organic-inorganic heteropolyacid salt | |
| CN111215138B (en) | Catalyst, preparation method and application of catalyst in preparation of beta-isophorone | |
| CN111269115A (en) | Preparation method of cinnamate in eutectic solvent | |
| CN114057578A (en) | Derivative of 2-trifluoromethyl cyclopentanone and preparation method thereof | |
| CN114230539B (en) | Synthesis process of ascorbyl tetraisopalmitate | |
| CN107778175A (en) | The synthesis technique of the tricaprylate of Isosorbide-5-Nitrae cyclohexanedimethanol two | |
| CN111875493A (en) | Method for synthesizing borneol by using imidazole acidic ionic liquid | |
| CN117946040A (en) | Method for preparing propiolactone by photochemical fluid reaction equipment | |
| CN109305912B (en) | Method for preparing 2,2, 4-trimethyl-1, 3-pentanediol monoisobutyrate by condensing isobutyraldehyde | |
| CN108003096B (en) | Method for preparing ethoxyquinoline through WO3/AC/SO3H concerted catalysis | |
| CN106977974B (en) | A kind of quinone dyestuff and preparation method thereof | |
| CN111229312B (en) | Solvent-free catalyst and preparation method and application thereof | |
| CN1043890C (en) | Method for the production of oxazole derivatives | |
| CN111116339B (en) | Method for artificially synthesizing curcumin and derivatives thereof | |
| CN108794432B (en) | Method for preparing gamma lactone by photosensitization catalysis | |
| CN113603580A (en) | Method for synthesizing methacrylic acid by decarboxylation of itaconic acid | |
| CN105399899B (en) | A kind of Preparation method and use of the molecularly imprinted polymer of the fat of catalyzing glycerol three hydrolysis | |
| CN107628919B (en) | Method for synthesizing beta-halogenated formate compound | |
| CN104151283A (en) | Method for catalytically synthesizing 12-aryl-8,9,10,12-tetrahydrobenzo[alpha]xanthenes-11-one derivative | |
| CN110590550A (en) | Synthesis method of allyl isovalerate | |
| CN110590522A (en) | Synthesis method of megastigmatrienone | |
| CN115677456B (en) | Preparation method of cannabidiol | |
| CN111718245B (en) | Method for preparing deuterated chemicals through photocatalytic decarboxylation conversion | |
| CN114478446B (en) | Method for preparing chromogen III by converting D-acetamido glucose | |
| CN115850225B (en) | Application of hesperidin and method for semisynthesis preparation of chrysin by using hesperidin derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination |