CN105001192A - Elpsilon-amyl propionate-elpsilon-caprolactone and preparation method thereof - Google Patents
Elpsilon-amyl propionate-elpsilon-caprolactone and preparation method thereof Download PDFInfo
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- CN105001192A CN105001192A CN201510351292.8A CN201510351292A CN105001192A CN 105001192 A CN105001192 A CN 105001192A CN 201510351292 A CN201510351292 A CN 201510351292A CN 105001192 A CN105001192 A CN 105001192A
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- compound
- caprolactone
- pentyl
- acid
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- -1 alcohol compound Chemical class 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000003377 acid catalyst Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 claims abstract description 4
- 230000032050 esterification Effects 0.000 claims abstract description 4
- 238000005886 esterification reaction Methods 0.000 claims abstract description 4
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical group OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 3
- 235000019800 disodium phosphate Nutrition 0.000 claims description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- IPVKBEOJURLVER-UHFFFAOYSA-N pentan-2-yl propanoate Chemical compound CCCC(C)OC(=O)CC IPVKBEOJURLVER-UHFFFAOYSA-N 0.000 claims 8
- 239000003205 fragrance Substances 0.000 abstract description 8
- 239000002304 perfume Substances 0.000 abstract description 7
- 235000009508 confectionery Nutrition 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 235000019991 rice wine Nutrition 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 description 12
- 235000019634 flavors Nutrition 0.000 description 12
- 150000002596 lactones Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000013599 spices Nutrition 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000422 delta-lactone group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- KTZNVZJECQAMBV-UHFFFAOYSA-N C(CC1)CN1C1=CCCCC1 Chemical compound C(CC1)CN1C1=CCCCC1 KTZNVZJECQAMBV-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Abstract
The invention discloses an elpsilon-lactone perfume compound with a structure as described in the specification. The invention also discloses a preparation method for the elpsilon-lactone perfume compound. The preparation method comprises the following steps: with an acid compound and an alcohol compound as raw materials, subjecting the raw materials to esterification in an organic solvent under the action of an acid catalyst so as to obtain an amyl propionate compound; and with the amyl propionate compound and an alkene compound as raw materials carrying out addition and Baeyer-Villiger oxidation reaction under the action of an alkali catalyst and an acid catalyst so as to eventually obtain an elpsilon-amyl propionate-elpsilon-caprolactone compound. The novel elpsilon-lactone perfume compound with characteristic bouquet and fragrance of mellow and sweet rice wine is a novel research achievement of domestic and overseas research on elpsilon-lactone perfume compounds with characteristic fragrance.
Description
Technical field
The invention belongs to chemical field, particularly relate to a kind of lactone type flavor compounds, a kind of ε specifically-n-pentyl propionate base-6-caprolactone and preparation method thereof.
Background technology
Lactone type flavor compounds is prevalent in occurring in nature, and most lactone type flavor compounds can obtain at occurring in nature, of many uses in the allotment of food flavor(ing) and daily chemical essence, and both can adjust as the main note of essence also can as batching.Most of lactone type flavor compounds threshold value is wherein low, in perfume formulation consumption save and also fragrance strong.Research both at home and abroad for lactone type flavor compounds generally exists: on gamma lactone type flavor compounds, delta-lactone type flavor compounds, macrolide type flavor compounds.Wherein gamma lactone type spices presents obvious fruital fragrance, delta-lactone type spices presents obvious milk fragrance, macrolide type spices presents obvious musky odor, the lactone type spices of this part uses natural sense that is stable, fragrance strong, and their major parts can obtain from occurring in nature, but cost is high, productive rate is low.But rarely have at present the research for ε-lactone type flavor compounds and preparation thereof both at home and abroad, ε-lactone type flavor compounds is at home and abroad studied and be all vacancy in preparing.
Summary of the invention
For technical problem of the prior art, the invention provides a kind of ε-n-pentyl propionate base-6-caprolactone and preparation method thereof, described this ε-n-pentyl propionate base-6-caprolactone and preparation method thereof solves in prior art prepares the technical problem that ε-lactone type flavor compounds is difficult, cost is high, productive rate is low.
The invention provides a kind of ε-n-pentyl propionate base-6-caprolactone, its structural formula is as follows:
。
Present invention also offers the preparation method of above-mentioned ε-n-pentyl propionate base-6-caprolactone, comprise the steps:
1) with acid compounds and alcohol compound for starting raw material, in the first organic solvent, by the first acid catalyst esterification, at the temperature of backflow, reaction 8-10h, prepares vinylformic acid n-pentyl ester compound;
2) vinylformic acid n-pentyl ester compound and vinyl compound are in a second organic solvent, by alkaline catalysts and the second acid catalysis
Agent addition, Baeyer-Villiger oxidation, in room temperature or lower than under reflux temperature, nitrogen protection, reaction 4-8h, prepares ε-n-pentyl propionate base-6-caprolactone compound.
Further, described acid compounds is vinylformic acid, and described alcohol compound is Pentyl alcohol, and described vinylformic acid and the mol ratio of Pentyl alcohol are 1.0:1.0 ~ 2.0.
Further, mole sum of described acid compounds and alcohol compound and the mol ratio of the first organic solvent are 1.0 ~ 1.5:1.0.
Further, the first described organic solvent is toluene.
Further, described acid compounds and alcohol compound: the mol ratio of the first acid catalyst is 10.0 ~ 15.0:1.0.
Further, described first acid catalyst is tosic acid.
Further, described vinylformic acid n-pentyl ester compound and the mol ratio of described vinyl compound are 1.5 ~ 2.5:1.0.
Further, described vinyl compound is 1-tetramethyleneimine-1-tetrahydrobenzene.
Further, the mol ratio of described vinylformic acid n-pentyl ester compound and vinyl compound and the second described organic solvent is 0.05 ~ 0.07:1.0.
Further, the second described organic solvent is methylene dichloride.
Further, described vinylformic acid n-pentyl ester and vinyl compound: the mol ratio of alkaline catalysts is 1.9 ~ 2.0:1.0.
Further, described alkaline catalysts is Sodium phosphate dibasic.
Further, described vinylformic acid n-pentyl ester and vinyl compound: the mol ratio of the second acid catalyst is 3.5 ~ 4.0:1.0.
Further, described second acid catalyst is metachloroperbenzoic acid.
The synthetic route of above-mentioned a kind of ε-n-pentyl propionate base-6-caprolactone compound is as follows:
Method of the present invention is for raw material with acid compounds and alcohol compound, by acid catalyst generation esterification in organic solvent, obtain vinylformic acid n-pentyl ester compound, gained vinylformic acid n-pentyl ester compound is raw material with vinyl compound again, in organic solvent by alkaline catalysts and acid catalyst generation addition and Baeyer-Villiger oxidizing reaction, finally obtain ε-n-pentyl propionate base-6-caprolactone compound.
The present invention compares with prior art, and its technical progress is significant.The invention provides a kind of ε-n-pentyl propionate base-6-caprolactone and synthetic method, being the compound of the aroma fragrance of the characteristic alcohol sweet wine of a kind of novel ε-lactone type band, is both at home and abroad for the newest research results of ε-lactone type with characteristic perfume compound.
Accompanying drawing explanation
Fig. 1 is the nucleus magnetic hydrogen spectrum analysis chart of the vinylformic acid n-pentyl ester of gained in embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum analysis chart of the ε-n-pentyl propionate base-6-caprolactone compound of gained in embodiment 2.
Fig. 3 is the nuclear-magnetism carbon spectrum analysis figure of the ε-n-pentyl propionate base-6-caprolactone compound of gained in embodiment 2.
Embodiment
Below by specific embodiment, the present invention is set forth further, but do not limit the present invention.
embodiment 1
A synthetic method for vinylformic acid n-pentyl ester compound, concrete steps are as follows:
In 100ml round-bottomed flask, add 17.32g(0.19mol) dry toluene, 4.9g(0.01mol) p-methyl benzenesulfonic acid, 7.245g(0.10mol) vinylformic acid, 11.02g (0.13mol) Pentyl alcohol stir at 110 DEG C of lower magnetic forces, reflux, react 8 hours; React complete, reaction solution is cooled to room temperature, in reaction solution, add saturated sodium bicarbonate aqueous solution, be extracted with ethyl acetate organic phase, organic phase saturated common salt water washing three times, anhydrous magnesium sulfate drying, revolve steaming except desolventizing with revolving steaming instrument, product utilization tlc obtains sterling, and eluent is PE:EA=8:1, collection sterling is final obtains clear colorless liquid 12.87ml, and productive rate is 94.2%.
The clear colorless liquid of above-mentioned gained carries out hydrogen spectrum by nuclear magnetic resonance apparatus (Bruker AVANCE III 500 MHz) and measures, data (as shown in Figure 1) as follows:
1H NMR (501 MHz, CDCl
3) δ 6.41 (d,
J= 17.3 Hz, 1H), 6.18 – 6.11 (m, 1H), 5.83 (d,
J= 10.4 Hz, 1H), 4.18 (s, 2H), 1.68 (d,
J= 7.0 Hz, 2H), 1.39 – 1.35 (m, 4H), 1.28 (t,
J= 7.1 Hz, 3H).
By the clear colorless liquid nuclear magnetic resonance spectrum data analysis of above-mentioned gained, result shows, the clear colorless liquid of above-mentioned gained is vinylformic acid n-pentyl ester.
embodiment 2
The synthetic method of above-mentioned a kind of ε-n-pentyl propionate base-6-caprolactone compound, concrete steps are as follows:
1.42g(0.01mol is added in 50ml there-necked flask) Sodium phosphate dibasic solid, nitrogen replacement three times, inject 13.25g (0.16mol) methylene dichloride, under magnetic agitation, inject 1.85g(0.013mol) vinylformic acid n-pentyl ester, 0.97g (0.0064mol) 1-tetramethyleneimine-1-tetrahydrobenzene, stir after 30 minutes, slow injection is dissolved in 0.86g (0.005mol) the metachloroperbenzoic acid solution of 13.25g (0.16mol) methylene dichloride, completed in 10 minutes, under magnetic agitation, reaction 4h, react complete, there-necked flask is put into frozen water cool, in reaction solution, add 15ml normal temperature saturated sodium bicarbonate aqueous solution wash one time, with 30ml saturated aqueous sodium thiosulfate washing twice, wash twice with 5% aqueous sodium hydroxide solution of 95ml, with 50ml distilled water wash twice, use dichloromethane extraction organic phase, organic phase is washed three times with 80ml saturated sodium-chloride water solution, finally use anhydrous magnesium sulfate drying organic phase, steaming removing organic phase is revolved with revolving steaming instrument, product utilization tlc obtains sterling, eluent is PE:EA=8:1, collection sterling is final obtains white solid 100mg, productive rate is 6.1%.
The white solid of above-mentioned gained carries out hydrogen spectrum by nuclear magnetic resonance apparatus (Bruker AVANCE III 500 MHz) and measures, data (as shown in Figure 2) as follows:
1H NMR (501 MHz, CDCl
3) δ 4.11 (dt,
J= 29.3, 6.7 Hz, 2H), 3.89 (t,
J= 5.6 Hz, 1H), 2.54 – 2.28 (m, 4H), 1.89 (d,
J= 4.3 Hz, 2H), 1.84 – 1.23 (m, 12H), 0.93 (t,
J= 6.6 Hz, 3H).
The white solid of above-mentioned gained carries out carbon spectrum by nuclear magnetic resonance apparatus (Bruker AVANCE III 500 MHz) and measures, data (as shown in Figure 3) as follows:
13C NMR (126 MHz, CDCl
3) δ 172.94 (s), 172.42 (s), 75.41 (s), 64.64 (s), 36.85 (d,
J= 7.3 Hz), 33.93 (s), 28.27 (d,
J= 3.4 Hz), 28.05 (d,
J= 3.8 Hz), 23.47 (s), 22.28 (s), 13.90 (s).
In sum, the invention provides the simple synthesis of a kind of ε-n-pentyl propionate base-6-caprolactone compound, being the novel and ε-lactone-type compound of aroma fragrance with characteristic alcohol sweet wine of a class, is both at home and abroad for the newest research results of ε-lactone type with characteristic perfume compound.
Above said content be only the present invention conceive under basic explanation, and according to any equivalent transformation that technical scheme of the present invention is done, all should protection scope of the present invention be belonged to.
Claims (10)
1. ε-n-pentyl propionate base-6-caprolactone, its structural formula is as follows:
。
2. the preparation method of a kind of ε according to claim 1-n-pentyl propionate base-6-caprolactone, is characterized in that comprising the steps:
With acid compounds and alcohol compound for starting raw material, in the first organic solvent, by the first acid catalyst esterification, at the temperature of backflow, reaction 8-10h, prepares vinylformic acid n-pentyl ester compound;
Vinylformic acid n-pentyl ester compound and vinyl compound are in a second organic solvent; be oxidized by alkaline catalysts and the second acid catalyst addition, Baeyer-Villiger; in room temperature or lower than under reflux temperature, nitrogen protection; reaction 4-8h, prepares ε-n-pentyl propionate base-6-caprolactone compound.
3. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, it is characterized in that: described acid compounds is vinylformic acid, described alcohol compound is Pentyl alcohol, and described vinylformic acid and the mol ratio of Pentyl alcohol are 1.0:1.0 ~ 2.0.
4. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, is characterized in that: mole sum of described acid compounds and alcohol compound and the mol ratio of the first organic solvent are 1.0 ~ 1.5:1.0.
5. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, is characterized in that: described acid compounds and alcohol compound: the mol ratio of the first acid catalyst is 10.0 ~ 15.0:1.0.
6. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, it is characterized in that: the first described organic solvent is toluene, described first acid catalyst is tosic acid.
7. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, it is characterized in that: described vinylformic acid n-pentyl ester compound and the mol ratio of described vinyl compound are 1.5 ~ 2.5:1.0, the mol ratio of described vinylformic acid n-pentyl ester compound and vinyl compound and the second described organic solvent is 0.05 ~ 0.07:1.0.
8. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, is characterized in that: the second described organic solvent is methylene dichloride, and described vinyl compound is 1-tetramethyleneimine-1-tetrahydrobenzene.
9. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, it is characterized in that: described vinylformic acid n-pentyl ester and vinyl compound: the mol ratio of alkaline catalysts is 1.9 ~ 2.0:1.0, described vinylformic acid n-pentyl ester and vinyl compound: the mol ratio of the second acid catalyst is 3.5 ~ 4.0:1.0.
10. the preparation method of a kind of ε as claimed in claim 2-n-pentyl propionate base-6-caprolactone, it is characterized in that: described second acid catalyst is metachloroperbenzoic acid, described alkaline catalysts is Sodium phosphate dibasic.
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| CN201510351292.8A CN105001192B (en) | 2015-06-23 | 2015-06-23 | ε n-pentyl propionate base ε caprolactones and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6431775A (en) * | 1987-07-28 | 1989-02-02 | Arakawa Chem Ind | Production of (r)-(+)-gamma-butyrolactone-gamma-3-propionic acid |
| JPS6463386A (en) * | 1987-09-01 | 1989-03-09 | Arakawa Chem Ind | Production of (r)-(+)-gamma-butyrolactone-gamma-3-propionic acid |
| CN103864601A (en) * | 2014-03-20 | 2014-06-18 | 广东广益科技实业有限公司 | Process for synthesizing milk lactone |
-
2015
- 2015-06-23 CN CN201510351292.8A patent/CN105001192B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6431775A (en) * | 1987-07-28 | 1989-02-02 | Arakawa Chem Ind | Production of (r)-(+)-gamma-butyrolactone-gamma-3-propionic acid |
| JPS6463386A (en) * | 1987-09-01 | 1989-03-09 | Arakawa Chem Ind | Production of (r)-(+)-gamma-butyrolactone-gamma-3-propionic acid |
| CN103864601A (en) * | 2014-03-20 | 2014-06-18 | 广东广益科技实业有限公司 | Process for synthesizing milk lactone |
Non-Patent Citations (1)
| Title |
|---|
| SERGIO PINHEIRO ET AL.: "Asymmetric Synthesis of 6-Carbomethoxyethyl-6-Methyl-ε-Caprolactone", 《J. BRAZ. CHEM. SOC.》 * |
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| CN105001192B (en) | 2017-05-31 |
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