CN106673980A - Device and method for continuously producing beta-ionone by using microchannel - Google Patents
Device and method for continuously producing beta-ionone by using microchannel Download PDFInfo
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- CN106673980A CN106673980A CN201611213334.2A CN201611213334A CN106673980A CN 106673980 A CN106673980 A CN 106673980A CN 201611213334 A CN201611213334 A CN 201611213334A CN 106673980 A CN106673980 A CN 106673980A
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- beta
- lonone
- micro passage
- passage reaction
- alpha
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- 238000000034 method Methods 0.000 title claims abstract description 27
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 title abstract 14
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 title abstract 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 26
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 56
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 claims description 39
- 239000001117 sulphuric acid Substances 0.000 claims description 11
- 235000011149 sulphuric acid Nutrition 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000003860 storage Methods 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000005292 vacuum distillation Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000001816 cooling Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 235000019155 vitamin A Nutrition 0.000 description 3
- 239000011719 vitamin A Substances 0.000 description 3
- 229940045997 vitamin a Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- -1 Hydroxyl -4- octyloxybenzophenone class compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00873—Heat exchange
Abstract
The invention discloses a device and method for continuously producing beta-ionone by using microchannel. The method comprises the following steps: preparing a pseudoionone organic solvent into a pseudoionone solution in volume percentage of 30-70%, adding the pseudoionone solution and concentrated sulfuric acid into a microchannel reactor respectively through two inlets of the microchannel reactor, reacting at a temperature of 25-30 DEG C, enabling reactant to flow out of the microchannel reactor, carrying out phase splitting treatment on the reactant by using a phase splitter to obtain a water phase and an oil phase containing beta-ionone, and treating the oil phase containing beta-ionone to obtain beta-ionone oily liquid. The method is convenient to operate and easily controllable in condition; the produced beta-ionone is high in yield and high in purity; the large-scale industrial production is facilitated; the microchannel reactor has extremely high heat exchange efficiency and is capable of preventing local temperature from excessively high, eliminating hot-spot temperature and improving the purity of the product which is beta-ionone; the continuous product is achieved; the production efficiency is improved; the copious cooling condition is avoided; the energy consumption is reduced; the cost is reduced.
Description
Technical field
The present invention relates to the apparatus and method that one kind microchannel continuously produces β-ionoionone.
Background technology
Β-ionoionone is a kind of important synthetic perfume, is also the important centre of synthetic vitamin A on medical industry
Body, it can be generated after pseudo ionone by citral and condensation of acetone, and cyclisation in acid condition is formed.According to ionoionone
Position of double bond it is different, there are α, three kinds of isomers of beta, gamma.The product of Cyclization be typically α-, the mixing of β-ionoionone
Thing.And in the synthesis of medical industry vitamin A, the purity of β-ionoionone affects very big on product, therefore, it is possible to simple
And high-purity beta-ionoionone is prepared in large quantity, it is the key point of β-ionoionone preparation technology development.
The at present synthesis of ionoionone mainly around the content for how improving β-ionoionone in cyclisation product, with full
Sufficient medical industry, especially vitamin A production needs.Chinese patent CN 1109462A are described and 2- are added in cyclization
Hydroxyl -4- octyloxybenzophenone class compounds are used as indexable preventing agent, but phase transfer catalyst used and indexable preventing agent valency
Lattice are expensive, it is impossible to reclaim, be unfavorable for industrialization.Reaction temperature affects very big to the selectivity of β-ionoionone, with reaction temperature
The rising of degree, the selectivity of β-ionoionone declines；With regard to the production of β-ionoionone, cyclization very exothermic, acid and
Pseudo ionone is two phase reaction, and difficult control of temperature makes yield low, α-content of isomer higher (3-5%).For
This deficiency, high mixing efficiency and heat exchange efficiency are the keys of process modification.German patent DE .3328440 proposes one kind and exists
By pseudo ionone and sulphuric acid by instantaneous touch, the method for producing β-ionoionone under room temperature, but this method needs special setting
Standby, condition control is difficult, therefore is not widely adopted.Chinese patent CN1129209A to be described and complete ring under a kind of ul-trasonic irradiation
The method for changing reaction, but Vltrasonic device energy consumption is larger, realizes that industrialized production has larger difficulty.Chinese patent
In CN02155069.7, dry ice is dividedly in some parts in cyclization, prevents hot-spot, but treating capacity is less, production efficiency
It is not high.Therefore, exploitation can have mix homogeneously, and heat transfer efficiency is high, effective control reaction temperature, realize simple, economical, efficient
The technique of continuous production β-ionoionone is this area in the urgent need to.
The content of the invention
The purpose of the present invention is to overcome the shortcomings of that prior art is present, there is provided one kind is simple, economical, efficiently use microchannel
The device of continuous production β-ionoionone.
Second object of the present invention is to provide a kind of method that micro passage reaction continuously produces alpha, beta-lonone.
Technical scheme is summarized as follows：
A kind of micro passage reaction continuously produces the device of alpha, beta-lonone, including the false He of violet solution reservoir 1
Sulfuric acid storage tank 2, also including micro passage reaction 3 and phase separator 4, the violet solution reservoir 1 and sulfuric acid storage tank 2 pass through respectively
Pipeline is connected with the two entrances of micro passage reaction 3, and the outlet of micro passage reaction 3 is connected by pipeline with the phase separator 4
Connect.
A kind of method that micro passage reaction continuously produces alpha, beta-lonone, comprises the steps：
(1) device of alpha, beta-lonone is continuously produced using a kind of above-mentioned micro passage reaction；
(2) pseudo ionone organic solvent is made into into the pseudo ionone solution that volume fraction is 30-70%, institute
State pseudo ionone solution and concentrated sulphuric acid is passed through in micro passage reaction respectively by the two entrances of micro passage reaction,
25-30 DEG C of reaction, product is flowed out after micro passage reaction, split-phase process is carried out with phase separator and obtains water phase and containing β-purple sieve
The oil phase of blue ketone, the oil phase containing alpha, beta-lonone obtains alpha, beta-lonone oil-based liquid through post processing.
The oil phase post processing of alpha, beta-lonone is preferably：Oil phase containing alpha, beta-lonone is used successively water, mass concentration
Aqueous sodium carbonate and water washing for 2%, vacuum distillation to be removed and obtain alpha, beta-lonone oil-based liquid after organic solvent.
The organic solvent is at least one in acetone, dichloromethane, chloroform, carbon tetrachloride and 1,2- dichloroethanes.
Flow-rate ratio of the concentrated sulphuric acid with volume fraction for the pseudo ionone solution of 30-70% is preferably 1~4:1.
Advantages of the present invention：
The method of the present invention is easy to operate, condition is easily-controllable, yield is high, purity is good, beneficial to industrialization large-scale production.Can be with
The Quick uniform in micro passage reaction mixes and reacts with concentrated sulphuric acid to make pseudo ionone solution, it is ensured that the two fully connects
Touch, while micro passage reaction has very high heat exchange efficiency, prevent local temperature too high, eliminate hot(test)-spot temperature, improve product
Alpha, beta-lonone purity.Answered by microchannel plate, realize continuous production, improve production efficiency.Cryogenic Conditions are avoided, energy is saved
Consumption, saves operating cost.
Description of the drawings
Fig. 1 is apparatus of the present invention schematic diagram.
Fig. 2 is method of the present invention process flow diagram.
Wherein：False violet solution reservoir --- 1；Sulfuric acid storage tank --- 2；Micro passage reaction --- 3；Split-phase
Device --- 4.
Specific embodiment
With reference to specific embodiment, the present invention is further illustrated.
A kind of micro passage reaction continuously produces the device of alpha, beta-lonone, sees Fig. 1, including the storage of false violet solution
Tank 1 and sulfuric acid storage tank 2, also including micro passage reaction 3 and phase separator 4,2 points of the violet solution reservoir 1 and sulfuric acid storage tank
Not Tong Guo pipeline be connected with the two entrances of micro passage reaction 3, the outlet of micro passage reaction 3 is by pipeline and the split-phase
Device 4 connects.Cooling water inlet pipe and outlet pipe are provided with micro passage reaction 3, water are provided with phase separator and are mutually managed and oil phase
Pipe.Embodiment 1
A kind of method that micro passage reaction continuously produces alpha, beta-lonone, is shown in Fig. 2, comprises the steps：
(1) device of alpha, beta-lonone is continuously produced using a kind of above-mentioned micro passage reaction；
(2) pseudo ionone acetone is made into into the pseudo ionone solution that volume fraction is 50% and (is stored in vacation
In property violet solution reservoir 1), pseudo ionone solution and concentrated sulphuric acid (concentrated sulphuric acid is stored in sulfuric acid storage tank 2) lead to respectively
The two entrances for crossing micro passage reaction 3 are passed through in micro passage reaction, and the flow of pseudo ionone solution is 9L/h, dense sulfur
The flow of acid is 18L/h, and 30 DEG C of reactions (cooling is passed through micro passage reaction with 10 DEG C of water), product flows out microchannel plate should
After device, split-phase carried out with phase separator 4 process to obtain water and mutually recycle, obtain the oil phase containing alpha, beta-lonone successively with water,
Mass concentration is 2% aqueous sodium carbonate and water washing, and vacuum distillation to be removed and obtain alpha, beta-lonone oil-based liquid after acetone.
In product, alpha, beta-lonone content is 96.8%, and α-ionone content is 0.7%.
Embodiment 2
A kind of method that micro passage reaction continuously produces alpha, beta-lonone, comprises the steps：
(1) device of alpha, beta-lonone is continuously produced using a kind of above-mentioned micro passage reaction；
(2) pseudo ionone dichloromethane is made into into the pseudo ionone solution that volume fraction is 70%, it is false
Ionoionone solution and concentrated sulphuric acid are passed through in micro passage reaction respectively by the two entrances of micro passage reaction, false purple sieve
The flow of blue ketone solution is 9L/h, and the flow of concentrated sulphuric acid is 36L/h, and in 25 DEG C of reactions, (5 DEG C of water of cooling are passed through microchannel plate should
Device), product is flowed out after micro passage reaction, split-phase is carried out with phase separator (4) processes to obtain water and mutually recycle, and is contained
The oil phase of alpha, beta-lonone is successively with the aqueous sodium carbonate and water washing that water, mass concentration are 2%, vacuum distillation removing dichloro
Alpha, beta-lonone oil-based liquid is obtained after methane.
In product, alpha, beta-lonone content is 98.2%, and α-ionone content is 0.6%.
Embodiment 3
A kind of method that micro passage reaction continuously produces alpha, beta-lonone, comprises the steps：
(1) device of alpha, beta-lonone is continuously produced using a kind of above-mentioned micro passage reaction；
(2) pseudo ionone mixed solvent is made into into the pseudo ionone solution (mixing that volume fraction is 30%
It is 1 that solvent is volume ratio:1:1 chloroform, carbon tetrachloride and 1,2- dichloroethanes composition), pseudo ionone solution and dense sulfur
Acid is passed through in micro passage reaction respectively by the two entrances of micro passage reaction (3), the flow of pseudo ionone solution
For 9L/h, the flow of concentrated sulphuric acid is 9L/h, and 28 DEG C of reactions (cooling is passed through micro passage reaction with 8 DEG C of water), product flows out
After micro passage reaction, split-phase is carried out with phase separator (4) process to obtain water and mutually recycle, obtain the oil containing alpha, beta-lonone
Mutually obtain β-purple after vacuum distillation removing mixed solvent with the aqueous sodium carbonate and water washing that water, mass concentration are 2% successively
Rowland ketone oil-based liquid.
In product, alpha, beta-lonone content is 96.3%, and α-ionone content is 1.1%.
Claims (5)
1. a kind of micro passage reaction continuously produces the device of alpha, beta-lonone, including false violet solution reservoir (1) and
Sulfuric acid storage tank (2), is characterized in that also including micro passage reaction (3) and phase separator (4), the violet solution reservoir 1 and sulfur
Acid storage tank (2) is connected respectively by pipeline with the two entrances of micro passage reaction (3), and the outlet of micro passage reaction (3) is led to
Piping is connected with the phase separator (4).
2. a kind of method that micro passage reaction continuously produces alpha, beta-lonone, is characterized in that comprising the steps：
(1) usage right requires a kind of 1 device that alpha, beta-lonone is continuously produced with micro passage reaction；
(2) pseudo ionone organic solvent is made into into the pseudo ionone solution that volume fraction is 30-70%, the vacation
Property ionoionone solution and concentrated sulphuric acid are passed through in micro passage reaction respectively by the two entrances of micro passage reaction, in 25-
30 DEG C of reactions, product is flowed out after micro passage reaction, split-phase process is carried out with phase separator and obtains water phase and containing β-violet
The oil phase of ketone, the oil phase containing alpha, beta-lonone obtains alpha, beta-lonone oil-based liquid through post processing.
3. the method that a kind of micro passage reaction according to claim 2 continuously produces alpha, beta-lonone, its feature exists
It is in the oil phase post processing of alpha, beta-lonone：By the oil phase containing alpha, beta-lonone successively with the carbonic acid that water, mass concentration are 2%
Sodium water solution and water washing, vacuum distillation to be removed and obtain alpha, beta-lonone oil-based liquid after organic solvent.
4. a kind of method for continuously producing alpha, beta-lonone with micro passage reaction according to Claims 2 or 3, its feature
It is that the organic solvent is at least one in acetone, dichloromethane, chloroform, carbon tetrachloride and 1,2- dichloroethanes.
5. the method that a kind of micro passage reaction according to claim 2 continuously produces alpha, beta-lonone, its feature exists
For the flow-rate ratio of the pseudo ionone solution of 30-70% it is 1~4 in concentrated sulphuric acid and volume fraction:1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611213334.2A CN106673980A (en) | 2016-12-24 | 2016-12-24 | Device and method for continuously producing beta-ionone by using microchannel |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611213334.2A CN106673980A (en) | 2016-12-24 | 2016-12-24 | Device and method for continuously producing beta-ionone by using microchannel |
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| CN106673980A true CN106673980A (en) | 2017-05-17 |
Family
ID=58870576
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| CN201611213334.2A Pending CN106673980A (en) | 2016-12-24 | 2016-12-24 | Device and method for continuously producing beta-ionone by using microchannel |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110304990A (en) * | 2019-05-29 | 2019-10-08 | 南京瑞鼎生物医药有限公司 | It is a kind of to produce vinyl β-ionol friendly process |
| CN110711524A (en) * | 2019-11-29 | 2020-01-21 | 福州大学 | Micro-fluidic device for measuring liquid-liquid phase balance |
| CN111285757A (en) * | 2018-12-10 | 2020-06-16 | 上虞新和成生物化工有限公司 | Method for cyclizing pseudo ionone |
| CN113372210A (en) * | 2021-06-08 | 2021-09-10 | 万华化学集团股份有限公司 | Preparation method of beta-ionone |
| CN113603577A (en) * | 2021-07-30 | 2021-11-05 | 万华化学集团股份有限公司 | Fragrance-controllable beta-ionone and preparation method thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285757A (en) * | 2018-12-10 | 2020-06-16 | 上虞新和成生物化工有限公司 | Method for cyclizing pseudo ionone |
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| CN110304990A (en) * | 2019-05-29 | 2019-10-08 | 南京瑞鼎生物医药有限公司 | It is a kind of to produce vinyl β-ionol friendly process |
| CN110304990B (en) * | 2019-05-29 | 2022-10-25 | 南京瑞鼎生物医药有限公司 | Green process for producing vinyl beta-ionol |
| CN110711524A (en) * | 2019-11-29 | 2020-01-21 | 福州大学 | Micro-fluidic device for measuring liquid-liquid phase balance |
| CN113372210A (en) * | 2021-06-08 | 2021-09-10 | 万华化学集团股份有限公司 | Preparation method of beta-ionone |
| CN113372210B (en) * | 2021-06-08 | 2022-04-19 | 万华化学集团股份有限公司 | Preparation method of beta-ionone |
| CN113603577A (en) * | 2021-07-30 | 2021-11-05 | 万华化学集团股份有限公司 | Fragrance-controllable beta-ionone and preparation method thereof |
| CN113603577B (en) * | 2021-07-30 | 2022-09-20 | 万华化学集团股份有限公司 | Fragrance-controllable beta-ionone and preparation method thereof |
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