CN106831382A - A kind of preparation method for improving αisomer yield in irisone product - Google Patents
A kind of preparation method for improving αisomer yield in irisone product Download PDFInfo
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- CN106831382A CN106831382A CN201611214298.1A CN201611214298A CN106831382A CN 106831382 A CN106831382 A CN 106831382A CN 201611214298 A CN201611214298 A CN 201611214298A CN 106831382 A CN106831382 A CN 106831382A
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- 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
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Abstract
The invention discloses a kind of preparation method for improving αisomer yield in irisone product.The method comprises the following steps：First, the irisone tails product of pseudo ionone product and beta isomer content more than 35% is prepared；2nd, the acid solution and organic solvent for accounting for total catalyst acid solution half are added in a reservoir, then irisone tails is added, and are stirred, it is warming up to 35 80 DEG C, pseudo ionone is added dropwise, remaining acid solution is added into completion after completion of dropping, continue keeping temperature and stir 14 hours；3rd, after reaction finishes standing, the sticky acid solution of lower floor is isolated, upper organic phase is washed to neutrality, and rectification under vacuum is carried out after having reclaimed solvent, obtains the high content first position irisone product that αisomer content is more than 86%.The present invention effectively increases the yield of αisomer in irisone product, and preparation method is simple, economic, practical, is suitable for the industrial continuous production of high content first position irisone.
Description
Technical field
The invention belongs to flavor chemistry field, alpha-isomer yield in specifically a kind of raising irisone product
Preparation method.
Background technology
Irisone, its chemical name is：4- (2,6,6- trimethyl-2- cyclo-octene-1- bases)-3- butene-2 -one, leads to
Normal product be α-, γ-, the mixture of β-tri- kind isomers, commodity irisone typically refers to α bodies and (is also first
Position) content 68-72%, β-body（Also second position is cried）The mixture of content 18-23%.Irisone is light yellow clear liquid.α bodies have
There are splendid and abundant violet, fragrance of a flower fragrance, a little warm wood sample iris note of band；146~147 DEG C of boiling point（28 millimeters of mercury
Post）, the grams per cubic centimter of density 0.9298（21℃）；Irisone is widely used in various types of blending essence, particularly can be with
For irisone, rose, Citrus compound perfume, but also for berries food flavor.Purple sieve in first position of high content
Blue ketone is also occurred frequently in the formula of various perfume odor types.High content first position irisone typically refers to α body content 88-92%,
The first position irisone product of β-body content 1-5%, it is prior in addition to for preparing luxury food or daily chemical essence purposes
Purposes is as preparing senior perfume material first position damascone（Or damascenone）, Damascenone, Megastigmatrienone（Or huge pillar three
Ketenes）Initiation material.β bodies have similar pine fragrant, and the violet fragrance of a flower is similar to during dilution；140 DEG C of boiling point（18 millimetress of mercury）,
Relative density 0.9462（20/4 ℃）；In addition to for preparing all kinds essence, prior purposes is application to β irisones
In the production of vitamin A.Its structural formula is as follows：
Existing irisone synthetic route is following two steps：First it is condensed in the basic conditions with citral and acetone, is obtained
Primary pseudo ionone, after rectifying obtains pseudo ionone product, then directly with acid with organic solvent carry out acidifying cyclisation,
Irisone product generally 60-70% containing alpha-isomer obtained by reaction, β-isomers 16 ~ 25%, γ-isomers 1-5%.As used
Strong acid, such as concentrated sulfuric acid and under solvent diluting condition, are cyclized compared with drastic conditions, then thermodynamic product alpha, beta-lonone.
Under current production specifications, the B position violet ketone requirement content more than 97% required for vitamin A production, first
The existing more implementation method of product within the content 1% of position, such as Chinese patent CN200810199197.0, CN1218455A;It is beautiful
State patent US5453546.But the synthetic technology method of high content first position irisone lacks enough research and implementation methods.
Common high content first position irisone product is the irisone mixture based on α bodies as obtained by weak acid is cyclized（α-
Isomers 63-72%, β-isomers 16 ~ 22%, γ-isomers 1-5%）Careful rectifying is carried out with the rectifying column of theoretical cam curve high
Segmentation and obtain, or separate to realize again after being complexed with chemical method.However, which kind of method, B position violet ketone is total
It is to be difficult to thoroughly be separated with first position, this production for allowing for high content first position irisone can produce not good purple sieve of a large amount of fragrance
Blue ketone tails（Commonly referred to lonone for soap, alpha-isomer 45-53%, β-isomers 32 ~ 40%）, whole violet can be made
The benefit of ketone series of products is not embodied most preferably.As the demand of high content first position irisone rises continuously and healthily,
The increase of lonone for soap needs to suppress.
Synthesis, pseudo ionone about pseudo ionone are converted into irisone master under strong acid, mild acid conditions
The reaction equation of isomers is wanted to be shown below；
The content of the invention
Present invention aim to address above-mentioned technical problem, there is provided one kind can be effectively improved in irisone production
Alpha-isomer quantum of output, using economic, practical, is suitable for the system of the industrial continuous production of high content first position irisone product
Preparation Method.
The technical scheme is that：
The preparation method for improving alpha-isomer yield in irisone product of the present invention, comprises the following steps：
（One）, prepare pseudo ionone product（Raw material）Irisone tails with β-content of isomer more than 35% is produced
Product, it is standby；
（Two）, carry out with irisone tails the acidifying cyclization of suppression β-isomers generation：In container（Such as reactor or
Flask）It is middle to add the acid solution and organic solvent for accounting for total catalyst acid solution 1/2nd, then by above-mentioned β-content of isomer
A certain amount of irisone tails more than 35% is added and stirred into container, is warming up to 35-80 DEG C, then starts to be added dropwise
Pseudo ionone, time for adding 1-3 hours, completion is added after completion of dropping by remaining 1/2nd acid solution, is continued
Keeping temperature is stirred 1-4 hours；
（Three）, reaction finish standing after, slowly isolate the sticky acid solution of lower floor, upper organic phase adds soda ash water, salt water washing
To neutral, rectification under vacuum is carried out after having reclaimed solvent, collect 121-123 DEG C/1.3kpa cuts, obtain alpha-isomer content 88%
The above, the high content first of β-content of isomer 1 ~ 5%, γ-content of isomer 2-5% position irisone product；
Wherein, the acid solution is 85% phosphoric acid, 60-65% sulfuric acid, aqueous phosphatic or the lewis acid aqueous solution；Preferred acid is molten
Liquid is 85% phosphoric acid.
Above-mentioned pseudo ionone：Organic solvent：Acid solution：The irisone tails more than 35% of β-content of isomer
Weight proportion be 1：0.5-1.5：0.2-1：0.1-0.6.Optimum ratio is：Pseudo ionone：Organic solvent：Acid solution：
The weight proportion of β-content of isomer irisone tails more than 35% is 1：1：0.25-0.5：0.3-0.4.
Above-mentioned steps（One）Preparation method be using existing conventional method prepare, such as by citral and acetone in alkaline bar
Condensation and rectifying under part, obtain pseudo ionone (referred to as vacation ketone) product, then carry out acidifying cyclisation instead with acid and organic solvent
Should（Existing conventional method）Synthesis irisone, alpha-isomer content 60 ~ 72% in this irisone product, β-content of isomer
16 ~ 18%, γ-isomers 2-5%；And 123-125 DEG C/1.3kpa irisone tails is collected when synthesizing after rectifying（α-isomery
Body content 45-55%, β-content of isomer 35-45%, γ-content of isomer 1-4%）.
The organic solvent is benzene, toluene, dichloromethane, dichloroethanes.
Above-mentioned steps（Three）In reaction finish be with chromatogram tracking reaction process to pseudo ionone material content≤
On the basis of 2%, then stop stirring, then stand.
The present invention is that β-content of isomer is high（More than 35%）Irisone tails add reaction system in advance,
β bodies are cyclized into suppress the new pseudo ionone for adding reaction system, so that more cyclisation turns into alpha-isomer, to reach
To the overall purpose for improving alpha-isomer quantum of output.
Compared with prior art, the technical scheme that the present invention is provided, with following technological merit：
1st, the technical scheme that the present invention is provided, generally improves the quantum of output of alpha-isomer in irisone product, preparation side
Method is simple, economic, practical, is suitable for the industrial continuous production of high content first position irisone product.Overcome prior art
The drawbacks of production high content first position irisone by-product more amount fragrance not good lonone for soap product.There is provided one kind even
During continuous property production irisone product, the reliable method of first position isomer quantum of output can be effectively improved, continuity batch is more, first
The raising of position isomer quantum of output is more obvious.
2nd, conventional method and the present invention simple contrast such as following table：
3rd, the quantum of output of first position isomer is effectively increased due to the technical scheme that the present invention is provided, can be by choosing suitable trays
Several rectifying stills carries out rectifying several times, and need not choose the too high rectifying still of the number of plates carries out single rectifying, is conducive to height to contain
The increased quality of amount first position irisone product, ensures that high content first position irisone reaches higher quality standard：α-isomery
Body content is up to more than 90%, β-content of isomer 1 ~ 3%, γ-content of isomer 2-5%.Avoid too high theoretical cam curve simultaneously
The drawbacks of energy consumption that rectifying still is caused is significantly increased and the product fragrance of a flower is not enough.
4th, recycled, drop by the acid solution that the technical scheme that the present invention is provided is isolated is after a small amount of fresh acid solution of supplement
Low production cost, be more that of avoiding a large amount of spent acid post processing is difficult and ambient influnence.
Specific embodiment
The preparation method for improving alpha-isomer yield in irisone product of the present invention, comprises the following steps：
（One）, prepare the irisone tails product of pseudo ionone product and β-content of isomer more than 35%, it is standby
With；
（Two）, carry out with irisone tails the acidifying cyclization of suppression β-isomers generation：In container（Reactor or burning
Bottle）It is middle to add the acid solution and organic solvent for accounting for total catalyst acid solution 1/2nd, then above-mentioned β-content of isomer is existed
More than 35% a certain amount of irisone tails is added and stirred into container, is warming up to 35-80 DEG C, then starts that vacation is added dropwise
Property irisone, time for adding 1-3 hours, remaining 1/2nd acid solution is added into completion after completion of dropping, continue to protect
Temperature is held to stir 1-4 hours；
（Three）, reaction finish standing after, slowly isolate the sticky acid solution of lower floor, upper organic phase adds soda ash water, salt water washing
To neutral, rectification under vacuum is carried out after having reclaimed solvent, collect 121-123 DEG C/1.3kpa cuts, obtain alpha-isomer content 88%
The above, the high content first of β-content of isomer 1 ~ 5%, γ-content of isomer 2-5% position irisone product；
Wherein, the acid solution is 85% phosphoric acid, 60-65% sulfuric acid, aqueous phosphatic or the lewis acid aqueous solution.Preferred acid is molten
Liquid is 85% phosphoric acid.
Above-mentioned pseudo ionone：Organic solvent：Acid solution：The irisone tails more than 35% of β-content of isomer
Weight proportion be 1：0.5-1.5：0.2-1：0.1-0.6.Optimum ratio is：Pseudo ionone：Organic solvent：Acid solution：
The weight proportion of β-content of isomer irisone tails more than 35% is 1：1：0.25-0.5：0.3-0.4.
Above-mentioned steps（One）Preparation method be using existing conventional method prepare, such as by citral and acetone in alkaline bar
Condensation and rectifying under part, obtain pseudo ionone (referred to as false ketone) product, then carry out acidifying ring with acid solution and organic solvent
Change reaction（Existing conventional method）Synthesis irisone, alpha-isomer content 60 ~ 72% in this irisone product, β-isomers
Content 16 ~ 18%, γ-isomers 2-5%；And 123-125 DEG C/1.3kpa irisone tails is collected when synthesizing after rectifying（α-
Content of isomer 45-55%, β-content of isomer 35-45%, γ-content of isomer 1-4%）.
The organic solvent is benzene, toluene, dichloromethane, dichloroethanes.
On the basis of chromatogram tracking reaction process to pseudo ionone material content≤2%, then it is that above-mentioned reaction is finished
Stop stirring, then stand.
The present invention is further illustrated below by the mode of embodiment, but does not constitute any limitation of the invention, appointed
The modification of the limited number of time that who is made in scope of the presently claimed invention is still in scope of the presently claimed invention.
Specific embodiment
According to prior art manner, the primary pseudo ionone of preparation is condensed by citral and acetone in the basic conditions,
And rectifying obtains pseudo ionone product（Abbreviation PI, content 95%）It is standby.It is again that a part of pseudo ionone product is direct
Acidifying cyclization is carried out with acid solution and organic solvent（Existing conventional method）Synthesis irisone, and in the course of reaction
Rectifying after collect 123-125 DEG C/1.3kpa irisone tails（Alpha-isomer content 45-55%, β-content of isomer 35-
45%, γ-content of isomer 1-4%）, it is standby.
Embodiment 1
By in the 50g phosphoric acid addition 2000ml there-necked flasks of 400g benzene, mass concentration 85%, stir, then heat to 35-
50 DEG C, add 160g irisone tails（Alpha-isomer content 50%, β-content of isomer 35%）, then start that 400g is added dropwise
Pseudo ionone, control time for adding 1.5-3 hours, after pseudo ionone completion of dropping, adds remaining 50g phosphoric acid；
Then heat to 50 ~ 55 DEG C and keep reaction 2-3 hours, with chromatogram tracking reaction process to PI content≤2%, stop stirring, stand
Layering.Slowly the sticky acid solution of lower floor is isolated after standing（Acid solution is weighed, and can be followed after lower batch of supplement is fresh to enough on a small quantity
Ring set is used）.Upper organic phase adds soda ash water, salt water washing to neutrality, and rectification under vacuum is carried out after having reclaimed benzene, collects 121-123
DEG C/1.3kpa cuts, and alpha-isomer content 87.6% is obtained, β-content of isomer 5.2%, the height of γ-content of isomer 3.8% contains
Amount first irisone product 243g.
123-125 DEG C/1.3kpa cuts are collected, lonone for soap product 222g is obtained（Alpha-isomer content 53.2%,
β-content of isomer 34.6%, γ-content of isomer 1.3%）.
Embodiment 2
By in the 100g phosphoric acid addition 2000ml there-necked flasks of 400g toluene, mass concentration 85%, stir, then heat to
35-50 DEG C, add the lonone for soap that example is obtained on 160g（Alpha-isomer content 53%, β-content of isomer about 35%）, so
After start that 400g pseudo ionones are added dropwise, control time for adding 1.5-3 hours after pseudo ionone completion of dropping, is added
Remaining 100g phosphoric acid；Then heat to 45 ~ 55 DEG C keep reaction 2-3 hours, with chromatogram tracking reaction process to PI contents≤
2%, stop stirring, stratification.Slowly the sticky acid solution of lower floor is isolated after standing（Acid solution is weighed, and treats down that batch supplement is a small amount of
It is recyclable after fresh to enough to apply mechanically）.Upper organic phase adds soda ash water, salt water washing to neutrality, is carried out very after having reclaimed toluene
Empty rectifying, collects 121-123 DEG C/1.3kpa cuts, obtains alpha-isomer content 88.8%, β-content of isomer 4.3%, γ-different
The high content first irisone product 238g of structure body content 3.3%；123-125 DEG C/1.3kpa cuts are collected, soap is obtained purple
Rowland ketone product 221g（Alpha-isomer content 51.8%, β-content of isomer 35.6%, γ-content of isomer 1.6%）.
Embodiment 3
By in the 75g sulfuric acid aqueous addition 2000ml there-necked flasks of 400g toluene, mass concentration 62%, stir, then heat up
To 35-45 DEG C, the lonone for soap that example is obtained on 160g is added（Alpha-isomer content 51.8%, β-content of isomer
35.6%）, then start that 400g pseudo ionones are added dropwise, control time for adding 1.5-3 hours, pseudo ionone is dripped
Bi Hou, adds remaining 75g62% sulfuric acid aqueous；Then 45 ~ 50 DEG C of keeping temperature is reacted 2-3 hours, with chromatogram tracking react into
Journey stops stirring, stratification to PI content≤2%.Slowly the sticky acid solution of lower floor is isolated after standing（Acid solution is weighed, and is treated
Lower batch of a small amount of fresh to enough rear being recycled of supplement is applied mechanically）.Upper organic phase adds soda ash water, salt water washing to neutrality, has reclaimed
Rectification under vacuum is carried out after toluene, 121-123 DEG C/1.3kpa cuts are collected, alpha-isomer content 86.3% is obtained, β-isomers contains
Measure the high content first irisone product 196g of 8.4%, γ-content of isomer 3.0%.
123-125 DEG C/1.3kpa cuts are collected, lonone for soap product 241g is obtained（Alpha-isomer content 49.6%,
β-content of isomer 37.5%, γ-content of isomer 1.3%）.
Embodiment 4
By in the 75g phosphoric acid addition 2000ml there-necked flasks of 400g benzene, mass concentration 85%, stir, then heat to 38-
50 DEG C, add the lonone for soap that example is obtained on 140g（Alpha-isomer content 49.6%, β-content of isomer 37.5%）, then
Start that 400g pseudo ionones are added dropwise, control time for adding 1.5-3 hours after pseudo ionone completion of dropping, is added surplus
Remaining 75g phosphoric acid；Then 40-55 DEG C of keeping temperature is reacted 2-3 hours, with chromatogram tracking reaction process to PI content≤2%, is stopped
Only stir, stratification.Slowly the sticky acid solution of lower floor is isolated after standing（Acid solution is weighed, can be according to lower batch of demand consumption
Recycled）.Upper organic phase adds soda ash water, salt water washing to neutrality, and the Choice Theory number of plates is at 30 pieces after having reclaimed benzene
Rectifying column carries out rectification under vacuum, collects 121-123 DEG C/1.3kpa cuts, obtains alpha-isomer content 91.6%, and β-isomers contains
Measure the high content first irisone product 205g of 2.3%, γ-content of isomer 3.1%.
123-125 DEG C/1.3kpa cuts are collected, lonone for soap product 236g is obtained（The % of alpha-isomer content 52.1,
β-content of isomer 35.3%, γ-content of isomer 1.4%）.
Embodiment 5
By in the 100g sulfuric acid aqueous addition 2000ml there-necked flasks of 400g dichloromethane, mass concentration 62%, stir, so
After be warming up to 50-60 DEG C, add the lonone for soap that example is obtained on 160g（Alpha-isomer content 52%, β-content of isomer
35%）, then start that 400g pseudo ionones, control time for adding 1.5-3 hours, pseudo ionone completion of dropping is added dropwise
Afterwards, remaining 100g62% sulfuric acid aqueous are added；Then 50-70 DEG C of keeping temperature is reacted 1-3 hours, with chromatogram tracking react into
Journey stops stirring, stratification to PI content≤2%.Slowly lower organic layer, and upper strata acid solution are isolated after standing（Acid is molten
Liquid is weighed, can be according to lower batch of demand consumption recycled）.The organic addition soda ash water of lower floor, salt water washing have reclaimed two to neutrality
Rectification under vacuum is carried out after chloromethanes, 121-123 DEG C/1.3kpa cuts are collected, alpha-isomer content 86.1%, β-isomers is obtained
Content 7.7%, the high content first irisone product 188g of γ-content of isomer 2.7%.
123-125 DEG C/1.3kpa cuts are collected, lonone for soap product 249g is obtained（Alpha-isomer content 48.9%,
β-content of isomer 37.9%, γ-content of isomer 1.2%）.
Claims (7)
1. it is a kind of improve irisone product in alpha-isomer yield preparation method, it is characterised in that comprise the following steps：
（One）, prepare the irisone tails product of pseudo ionone product and β-content of isomer more than 35%, it is standby
With；
（Two）, carry out with irisone tails the acidifying cyclization of suppression β-isomers generation：Add in a reservoir and account for total
The acid solution and organic solvent of catalyst acid solution 1/2nd, it is then that above-mentioned β-content of isomer is certain more than 35%
Amount irisone tails is added and stirred into container, is warming up to 35-80 DEG C, then starts that pseudo ionone, drop is added dropwise
1-3 hours between the added-time, remaining 1/2nd acid solution is added into completion after completion of dropping, continue keeping temperature stirring 1-4
Hour；
（Three）, reaction finish standing after, slowly isolate the sticky acid solution of lower floor, upper organic phase adds soda ash water, salt water washing
To neutral, rectification under vacuum is carried out after having reclaimed solvent, collect 121-123 DEG C/1.3kpa cuts, obtaining alpha-isomer content is
More than 86%, the high content first position irisone product of β-content of isomer 1 ~ 5%, γ-content of isomer 2-5%；
Wherein, the acid solution is 85% phosphoric acid, 60-65% sulfuric acid, aqueous phosphatic or the lewis acid aqueous solution；
The pseudo ionone：Organic solvent：Acid solution：The weight of β-content of isomer irisone tails more than 35%
Amount proportioning is 1：0.5-1.5：0.2-1：0.1-0.6.
2. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：On
State pseudo ionone：Organic solvent：Acid solution：The weight proportion of β-content of isomer irisone tails more than 35%
It is 1：1：0.25-0.5：0.3-0.4.
3. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：On
Organic solvent is stated for benzene, toluene, dichloromethane or dichloroethanes.
4. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：On
It is 38-55 DEG C to state the reaction temperature in container.
5. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：
Above-mentioned steps（One）In, be condensed in the basic conditions with citral and acetone, rectifying, obtain pseudo ionone product；Again
A part of pseudo ionone product is carried out into acidifying cyclization synthesis irisone, this purple sieve with acid solution and organic solvent
Alpha-isomer content 60 ~ 72% in blue ketone product, β-content of isomer 16 ~ 18%, γ-isomers 2-5%；And in synthetic reaction mistake
123-125 DEG C/1.3kpa irisone tails, the alpha-isomer content of the irisone tails are collected after rectifying in journey
45-55%, β-content of isomer 35-45%, γ-content of isomer 1-4%.
6. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：Will
Step（Three）Irisone tails obtained by middle rectifying continues to be proportionally added into the acidifying cyclization of next group irisone.
7. the preparation method of alpha-isomer yield in irisone product is improved according to claim 1, it is characterised in that：Will
Step（Three）In separate a small amount of fresh acid solution of lower floor acid solution supplement after can be recycled.
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| CN108329200A (en) * | 2018-03-21 | 2018-07-27 | 万华化学集团股份有限公司 | A method of preparing alpha, beta-lonone by raw material of pseudoionone |
| CN109665977A (en) * | 2018-12-21 | 2019-04-23 | 广州百花香料股份有限公司 | The production method of efficient irisone-α hydroxyl sulfoacid sodium addition product |
| CN110002983A (en) * | 2019-04-25 | 2019-07-12 | 上海应用技术大学 | A kind of method for making alpha, beta-lonone reduce isomerization in distillation process |
| CN110002981A (en) * | 2019-04-19 | 2019-07-12 | 万华化学集团股份有限公司 | A method of preparing pseudo 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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329200A (en) * | 2018-03-21 | 2018-07-27 | 万华化学集团股份有限公司 | A method of preparing alpha, beta-lonone by raw material of pseudoionone |
| CN108329200B (en) * | 2018-03-21 | 2021-03-09 | 万华化学集团股份有限公司 | Method for preparing beta-ionone by using pseudoionone as raw material |
| CN109665977A (en) * | 2018-12-21 | 2019-04-23 | 广州百花香料股份有限公司 | The production method of efficient irisone-α hydroxyl sulfoacid sodium addition product |
| CN110002981A (en) * | 2019-04-19 | 2019-07-12 | 万华化学集团股份有限公司 | A method of preparing pseudo ionone |
| CN110002981B (en) * | 2019-04-19 | 2022-01-07 | 万华化学集团股份有限公司 | Method for preparing pseudo ionone |
| CN110002983A (en) * | 2019-04-25 | 2019-07-12 | 上海应用技术大学 | A kind of method for making alpha, beta-lonone reduce isomerization in distillation process |
| 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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Application publication date: 20170613 |