CN103044223A - Method for continuously preparing pseudo ionone of vitamin A intermediate - Google Patents
Method for continuously preparing pseudo ionone of vitamin A intermediate Download PDFInfo
- Publication number
- CN103044223A CN103044223A CN2012105814350A CN201210581435A CN103044223A CN 103044223 A CN103044223 A CN 103044223A CN 2012105814350 A CN2012105814350 A CN 2012105814350A CN 201210581435 A CN201210581435 A CN 201210581435A CN 103044223 A CN103044223 A CN 103044223A
- Authority
- CN
- China
- Prior art keywords
- citral
- reaction
- acetone
- pseudo ionone
- pressure
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a method for continuously preparing pseudo ionone of a vitamin A intermediate. The method evenly mixes acetone, citral and catalyst under the continuous operation condition and introduces in a tubular reactor. The reaction mixture is continuously reacted for 1-120 minutes at the reaction temperature of 20-150 DEG C under the pressure of 0-10 MPa; reaction liquid is relieved pressure to enter a flash column; recovered acetone is obtained from the top of the column; tower bottoms are introduced in a layering machine for layering; after being neutralized, oil layers are relieved pressure and recovered to obtain pseudo ionone crude products, and are further distilled in high vacuum and separated out unreacted citral and pseudo ionone competitive products; and the recovered light-component by-products and the unreacted citral are mixed with the recovered acetone to enter the reactor again. The method has the advantages of low catalyst concentration, low corrosion to equipment, short reaction time and fewer side effects; and part by-products can be recycled.
Description
Technical field
The present invention relates to the field of chemical synthesis, be specifically related to the method that a kind of continuity prepares the vitamin A intermediate pseudo ionone.
Background technology
Pseudo ionone, chemical name 6,10-dimethyl-3,5,9-undecane triolefin-2-ketone, weak yellow liquid.Pseudo ionone is the important intermediate of synthetic jononeionone, is widely used in spices, medicine, foodstuff additive industry.A kind of rare spice with banksia rose type fragrance of jononeionone is one of maximum and of paramount importance spices of output in the perfume industry; Synthetic alpha, beta-lonone is the important intermediate of synthesise vitamins A and β-carotene simultaneously.
During Chinese scholars is continuing to carry out to the improvement of the synthesis technique of pseudo ionone research always for a long time.Its main synthetic method be the citral that separated by litsea cubeba oil under alkaline condition with acetone through Aldol condensation system to.
PL147748 has described and has a kind ofly prepared the method for pseudo ionone with alkaline ion exchanger at 56 ℃ of lower condensation citrals and acetone, and there is the shortcoming of low-down space-time yield in the method.
US Patent No. 4874900(1989) method for preparing pseudo ionone with hydrogen-oxygen lithium catalyzing and condensing citral and acetone has been described, the method under-20~240 ℃ of temperature intermittently or carry out continuously condensation reaction.The method need to leach excessive catalyzer when reaction is finished.There is long reaction time in the method, and side reaction is many, the shortcoming that the low and solid waste of yield is difficult etc.
Above-mentioned patent has been described the method for the synthetic pseudo ionone of a kind of serialization.The method is used excessive high density alkali metal hydroxide aqueous solution, and is very high to the equipment corrosion requirement, and causes a large amount of noxious waste pollutions.
Summary of the invention
The purpose of this invention is to provide a kind of method that under lower concentration catalyzer condition, catalyzes and synthesizes the pure pseudo ionone of fragrance.
For achieving the above object, the present invention adopts following technical scheme:
A kind of continuity prepares the method for vitamin A intermediate pseudo ionone, comprises the steps:
A) aqueous acetone and citral are mixed, after the preheater heating, mix in static mixer with the lower concentration alkali metal hydroxide aqueous solution, enter tubular reactor and carry out condensation reaction;
B) after reaction was finished, reaction solution entered flashing tower through decompression, is recycled acetone from cat head, and tower bottoms enters the quantizer layering after neutralization;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further rectifying separation goes out unreacted citral and pseudo ionone elaboration again, and the light constituent by product of recovery and unreacted citral mix with recovery acetone, again enter reactor.
Wherein, aqueous acetone and citral mix continuously with the mol ratio of 2:1~40:1 among the described step a; Aqueous acetone and citral mix continuously with the mol ratio of 15:1~30:1 among the preferred steps a, and wherein, the discharge rate of citral and aqueous acetone is respectively 120-150g/h and 1000-1500g/h; More preferably the mol ratio of acetone and citral is 20:1.Unreacted recover acetone is applied mechanically.
Wherein, the water content of acetone described in the step a is 2~20%, preferred 5~15%.The acetone moisture content can be regulated with the new acetone of part according to reclaiming acetone mixture moisture.
Continuity of the present invention prepares the method for vitamin A intermediate pseudo ionone, and the alkali metal hydroxide aqueous solution described in the step a is the aqueous solution of one or more mixtures in lithium hydroxide, sodium hydroxide or the potassium hydroxide.The mass concentration of described alkali metal hydroxide is 0.005~5%, preferred 0.01~2%.The special feature of catalyzer of the present invention is not need filtering catalyst after reaction finishes, and does not produce solid waste.
Continuity of the present invention prepares the method for vitamin A intermediate pseudo ionone, and the temperature of reaction of condensation reaction is 20~150 ℃ among the described step a; Reaction times is 1~120 minute, and reaction pressure is the pressure 0~10Mpa that is higher than saturated vapor pressure under the respective reaction temperature, and preferable reaction temperature is 80~120 ℃; Reaction times is 5~60 minutes, and reaction pressure is the pressure 6 ~ 10MPa that is higher than saturated vapor pressure under the respective reaction temperature.
Continuity of the present invention prepares the method for vitamin A intermediate pseudo ionone, is organic acid with the neutralizing agent that uses among the described step b, preferred acetic acid or citric acid.
Continuity of the present invention prepares the method for vitamin A intermediate pseudo ionone, and rectification under vacuum is adopted in rectifying among the described step c, and working pressure is for being lower than 200Pa.
More specifically, the continuity of the present invention method for preparing the vitamin A intermediate pseudo ionone comprises the steps:
A) be that 5~15% aqueous acetone and citral mix continuously with the mol ratio of 15:1~30:1 with water-content, wherein, the discharge rate of citral and aqueous acetone is respectively 120-150g/h and 1000-1500g/h; Mixed solution is forced into 6-10MPa through pump, be heated to 80-120 ℃ through preheater, being 0.005~5% alkali metal hydroxide aqueous solution with the mass concentration that is forced into uniform pressure mixes through static mixer with the discharge rate of 80-120g/h, enter tubular reactor and carry out condensation reaction, the reaction times is 5-60 minute;
B) reaction finish after, reaction solution enters flashing tower through decompression, is recycled acetone from cat head, in the tower bottoms and after enter the quantizer layering;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further rectifying separation goes out unreacted citral and pseudo ionone elaboration again, and the light constituent by product of recovery and unreacted citral mix with recovery acetone, again enter reactor.
After step b finished, tower bottoms entered the quantizer layering after neutralizing treatment, obtain oil reservoir and in and waste water layer, described oil reservoir namely comprises target product, light constituent by product and unreacted citral, in and waste water layer comprise part acetone and Pyranton.Mixture after the layering separates respectively or post-processing operation.Concrete separation and aftertreatment are those skilled in the art and grasp, and the present invention is not particularly limited this.
As preferred forms of the present invention, the method that preferred described continuity prepares the vitamin A intermediate pseudo ionone comprises the steps:
A) be that 10% aqueous acetone and citral mix continuously with the mol ratio of 20:1 with water-content, wherein, the discharge rate of citral and aqueous acetone is respectively 145g/h and 1200g/h; Be forced into 8MPa through pump, be heated to 100 ℃ through preheater, being 0.4% alkali metal hydroxide aqueous solution with the mass concentration that is forced into uniform pressure mixes through static mixer with the discharge rate of 100g/h, enters tubular reactor and carries out condensation reaction, and the reaction times is 10 minutes;
B) reaction finish after, reaction solution enters flashing tower through decompression, is recycled acetone from cat head, tower bottoms with in the citric acid with after enter the quantizer layering;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further rectifying separation goes out unreacted citral and pseudo ionone elaboration again, and the light constituent by product of recovery and unreacted citral mix with recovery acetone, again enter reactor.
The citral that the present invention purifies through high-vacuum fractionation take litsea cubeba oil is as raw material, method to the continuous production pseudo ionone is studied, it is characterized in that using the lower concentration alkali metal hydroxide aqueous solution to catalyze and synthesize the pure pseudo ionone of fragrance, and unreacted citral and part by product turned back in the reaction, make side reaction maintain a low level.In addition, the light constituent by product that vacuum reclaims among the present invention and unreacted citral with reclaim acetone and mix and turn back in the condensation reaction, with the generation of reduction by product.
Adopt technique scheme, the present invention is with the synthetic pseudo ionone of citral continuity, and it is low to have overcome space-time yield, has the shortcoming of noxious waste pollution, meets the idea of development of green chemical industry.In addition, the synthetic pseudo ionone yield of the present invention can reach more than 91%, and purity is a kind of desirable synthetic method promoted up to more than 94.0%.
Embodiment
Following examples are used for explanation the present invention, but are not used for limiting the scope of the invention.Without departing from the spirit and substance of the case in the present invention, modification or replacement to the inventive method, step or condition are done all belong to scope of the present invention.
If do not specialize, the conventional means that used technique means is well known to those skilled in the art among the embodiment.
Embodiment 1
Citral 145g/h(content 97.3%, purify through high-vacuum fractionation with litsea cubeba oil and to make) and the acetone 1200g/h of water content 10% mix, be forced into 8MPa through pump, enter preheater and be heated to 100 ℃, then mix through static mixer with 0.4% the NaOH aqueous solution 100g/h that is pressurized to uniform pressure, enter tubular reactor and carry out condensation reaction.Reaction time 10 minutes, the reaction solution gas chromatographic analysis, reaction solution enters flashing tower after being decompressed to normal pressure, obtain moisture 8% recovery acetone from cat head, tower bottoms with in an amount of citric acid and after enter the quantizer layering, oil reservoir obtains pseudo ionone crude product 202.6g/h through reclaim under reduced pressure, the gas-chromatography test analysis, crude product further high vacuum rectification is isolated unreacted light constituent and citral and pseudo ionone elaboration 171.2g/h, content is two kinds of content of isomer sums of 95.2%(), the citral transformation efficiency is 97.8%, selectivity is 98.68%, relatively and citral, the pseudo ionone yield is 93.3%.Fed with acetone is that fresh acetone adds the water mixing in the present embodiment, and water content is about 10%.Table 1 is the gas chromatographic analysis result:
Table 1
Embodiment 2
According to the method for embodiment 1, different is that citral is take 150g/h(content 97.3%) and the acetone 1000g/h of water content 15% mix (mol ratio of acetone and citral is 15:1), other conditions are constant.Obtain pseudo ionone elaboration 177.3g/h, content is two kinds of content of isomer sums of 94.9%(), the citral transformation efficiency is 96.41%, and selectivity is 98.9%, and relative and citral pseudo ionone yield is 91.23%.
Embodiment 3
According to the method for embodiment 1, different is that citral is take 120g/h(content 97.3%) and the acetone 1500g/h of water content 10% mix (mol ratio of acetone and citral is 30:1), other conditions are constant.Obtain pseudo ionone elaboration 142.2g/h, content is two kinds of content of isomer sums of 95.5%(), relative and citral pseudo ionone yield is 91.44%.
Embodiment 4 ~ 5
According to the method for embodiment 1, different is to carry out respectively citral condensation reaction (mol ratio of acetone and citral is 20:1) under 6MPa and 10MPa, and other conditions are constant.Test-results is as shown in table 2:
Table 2
Sequence number | Reaction pressure | Transformation efficiency/% | Selectivity/% | Yield/% |
Embodiment 4 | 6MPa | 97.43 | 98.55 | 92.36 |
Embodiment 5 | 10MPa | 98.97 | 97.28 | 91.88 |
Embodiment 6 ~ 8
Method according to embodiment 1, different is to carry out respectively citral condensation reaction (mol ratio of acetone and citral is 20:1) under differing temps, the citral transformation efficiency is the foundation of reaction end in the vapor-phase chromatography monitoring reaction mixed solution, and other conditions are constant.Test-results is as shown in table 3:
Table 3
Sequence number | Temperature of reaction | Reaction times | Transformation efficiency/% | Selectivity/% | Yield/% |
Embodiment 6 | 20℃ | 108min | 98.16 | 98.27 | 92.14 |
Embodiment 7 | 80℃ | 43min | 98.45 | 98.19 | 92.59 |
Embodiment 8 | 150℃ | 2min | 98.08 | 97.17 | 91.11 |
Embodiment 9 ~ 11
According to the method for embodiment 1, different is to carry out condensation reaction with the different acetone of water content, and other conditions are constant.Test-results is as shown in table 4:
Table 4
Sequence number | The acetone water content | Transformation efficiency/% | Selectivity/% | Yield/% |
Embodiment 9 | 2% | 97.34 | 98.05 | 91.22 |
Embodiment 10 | 5% | 98.12 | 98.61 | 92.45 |
Embodiment 11 | 20% | 97.98 | 98.37 | 91.59 |
Embodiment 12
Method according to embodiment 1, different is that citral is with 142g/h(content 97.3%) and the acetone 1200g/h of water content 10% mix, the acetone here is the mixture that reclaims acetone, rectifying light constituent and unreacted citral 2.4g fresh acetone, and other conditions are constant.Obtain pseudo ionone elaboration 168.1g/h, content is two kinds of content of isomer sums of 94.7%(), the citral transformation efficiency is 96.95%, and selectivity is 99.1%, and relative and citral pseudo ionone yield is 93.0%.Fed with acetone is for reclaiming the mixture of acetone, rectifying light constituent and unreacted citral fresh acetone in the present embodiment, and water content is about 10%.
Table 5 is the gas chromatographic analysis result:
Table 5
Embodiment 13 ~ 16
According to embodiment 1,12 method, different is take mass concentration as 0.3% the LiOH aqueous solution and 0.5% the KOH aqueous solution carry out catalyzed reaction with the throwing amount speed of 100g/h, other conditions are constant.Test-results is as shown in table 6:
Table 6
Above-mentioned test-results shows, the present invention carries out condensation reaction at the lower alkali metal hydroxide aqueous solution of working concentration as catalyzer and prepares pseudo ionone, side reaction is few, yield is high, there is not unnecessary solid waste, and continuous reaction conditional stability, the pseudo ionone fragrance of output is pure, is easy to realize suitability for industrialized production.
Although, above used general explanation, embodiment and test, the present invention is described in detail, on basis of the present invention, can make some modifications or improvements it, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. a continuity prepares the method for vitamin A intermediate pseudo ionone, it is characterized in that: comprise the steps:
A) aqueous acetone and citral are mixed, after the preheater heating, mix in static mixer with alkali metal hydroxide aqueous solution, enter tubular reactor and carry out condensation reaction;
B) after reaction was finished, reaction solution entered flashing tower through decompression, is recycled acetone from cat head, and tower bottoms enters the quantizer layering after neutralization;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further high vacuum rectification is isolated unreacted citral and pseudo ionone elaboration again; The light constituent by product that reclaims and unreacted citral mix with recovery acetone, again enter reactor;
2. method according to claim 1, it is characterized in that: aqueous acetone and citral mix continuously with the mol ratio of 2:1~40:1 among the described step a; Aqueous acetone and citral mix continuously with the mol ratio of 15:1~30:1 among the preferred steps a, and wherein, the discharge rate of citral and aqueous acetone is respectively 120-150g/h and 1000-1500g/h.
3. method according to claim 1 and 2, wherein acetone water content described in the step a is 2~20%, preferred 5~15%.
4. method according to claim 1, it is characterized in that: the alkali metal hydroxide aqueous solution described in the described step a is the aqueous solution of one or more mixtures in lithium hydroxide, sodium hydroxide or the potassium hydroxide.
5. according to claim 1 or 4 described methods, it is characterized in that: the alkali metal hydroxide mass concentration 0.005~5% that described step a uses, preferred 0.01~2%.
6. method according to claim 1, it is characterized in that: the temperature of reaction of condensation reaction is 20~150 ℃ among the described step a; Reaction times is 1~120 minute, and reaction pressure is the pressure 0~10Mpa that is higher than saturated vapor pressure under the respective reaction temperature; Preferable reaction temperature is 80~120 ℃; Reaction times is 5~60 minutes, and reaction pressure is the pressure 6 ~ 10MPa that is higher than saturated vapor pressure under the respective reaction temperature.
7. method according to claim 1 is characterized in that: be organic acid with the neutralizing agent that uses among the described step b, preferred acetic acid or citric acid.
8. method according to claim 1 is characterized in that: rectification under vacuum is adopted in rectifying among the described step c, and working pressure is for being lower than 200Pa.
9. method according to claim 1 is characterized in that: comprise the steps:
A) be that 5~15% aqueous acetone and citral mix continuously with the mol ratio of 15:1~30:1 with water-content, wherein, the discharge rate of citral and aqueous acetone is respectively 120-150g/h and 1000-1500g/h; Mixed solution is forced into 6-10MPa through pump, be heated to 80-120 ℃ through preheater, being 0.005~5% alkali metal hydroxide aqueous solution with the mass concentration that is forced into uniform pressure mixes through static mixer with the discharge rate of 80-120g/h, enter tubular reactor and carry out condensation reaction, the reaction times is 5-60 minute;
B) reaction finish after, reaction solution enters flashing tower through decompression, is recycled acetone from cat head, in the tower bottoms and after enter the quantizer layering;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further rectifying separation goes out unreacted citral and pseudo ionone elaboration again, and the light constituent by product of recovery and unreacted citral mix with recovery acetone, again enter reactor.
10. method according to claim 9 is characterized in that: comprise the steps:
A) be that 10% aqueous acetone and citral mix continuously with the mol ratio of 20:1 with water-content, wherein, the discharge rate of citral and aqueous acetone is respectively 145g/h and 1200g/h; Mixed solution is forced into 8MPa through pump, be heated to 100 ℃ through preheater, being 0.4% alkali metal hydroxide aqueous solution with the mass concentration that is forced into uniform pressure mixes through static mixer with the discharge rate of 100g/h, enters tubular reactor and carries out condensation reaction, and the reaction times is 10 minutes;
B) reaction finish after, reaction solution enters flashing tower through decompression, is recycled acetone from cat head, tower bottoms with in the citric acid with after enter the quantizer layering;
C) oil reservoir obtains the pseudo ionone crude product through reclaim under reduced pressure, and further rectifying separation goes out unreacted citral and pseudo ionone elaboration again, and the light constituent by product of recovery and unreacted citral mix with recovery acetone, again enter reactor.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210581435.0A CN103044223B (en) | 2012-12-28 | 2012-12-28 | Method for continuously preparing pseudo ionone of vitamin A intermediate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210581435.0A CN103044223B (en) | 2012-12-28 | 2012-12-28 | Method for continuously preparing pseudo ionone of vitamin A intermediate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103044223A true CN103044223A (en) | 2013-04-17 |
CN103044223B CN103044223B (en) | 2015-04-15 |
Family
ID=48057111
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210581435.0A Active CN103044223B (en) | 2012-12-28 | 2012-12-28 | Method for continuously preparing pseudo ionone of vitamin A intermediate |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103044223B (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103524317A (en) * | 2013-09-22 | 2014-01-22 | 上虞新和成生物化工有限公司 | Synthesis method of pseudoionone |
CN103694215B (en) * | 2013-12-10 | 2016-05-11 | 安徽丰原发酵技术工程研究有限公司 | A kind of continuity is prepared method and the device of DXPE |
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 |
CN111825538A (en) * | 2020-07-13 | 2020-10-27 | 万华化学集团股份有限公司 | Method for continuously producing pseudo ionone |
CN111978165A (en) * | 2020-08-06 | 2020-11-24 | 上海应用技术大学 | Method for improving acetone recovery rate in condensation process of producing pseudo ionone |
CN112638855A (en) * | 2020-11-18 | 2021-04-09 | 厦门金达威维生素有限公司 | Continuous synthesis method of pseudo ionone |
CN113548952A (en) * | 2021-07-28 | 2021-10-26 | 万华化学集团股份有限公司 | Preparation method of high-quality pseudo ionone |
CN113563168A (en) * | 2021-07-06 | 2021-10-29 | 万华化学集团股份有限公司 | Method for reducing waste water in production of pseudo ionone |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4431844A (en) * | 1981-04-08 | 1984-02-14 | Basf Aktiengesellschaft | Preparation of polyunsaturated ketones |
CN1711232A (en) * | 2002-11-07 | 2005-12-21 | 巴斯福股份公司 | Continuous process for producing pseudoionones and ionones |
-
2012
- 2012-12-28 CN CN201210581435.0A patent/CN103044223B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4431844A (en) * | 1981-04-08 | 1984-02-14 | Basf Aktiengesellschaft | Preparation of polyunsaturated ketones |
CN1711232A (en) * | 2002-11-07 | 2005-12-21 | 巴斯福股份公司 | Continuous process for producing pseudoionones and ionones |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103524317A (en) * | 2013-09-22 | 2014-01-22 | 上虞新和成生物化工有限公司 | Synthesis method of pseudoionone |
CN103524317B (en) * | 2013-09-22 | 2015-08-12 | 上虞新和成生物化工有限公司 | The synthetic method of pseudo ionone |
CN103694215B (en) * | 2013-12-10 | 2016-05-11 | 安徽丰原发酵技术工程研究有限公司 | A kind of continuity is prepared method and the device of DXPE |
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 |
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 |
CN111825538A (en) * | 2020-07-13 | 2020-10-27 | 万华化学集团股份有限公司 | Method for continuously producing pseudo ionone |
CN111825538B (en) * | 2020-07-13 | 2022-08-05 | 万华化学集团股份有限公司 | Method for continuously producing pseudo ionone |
CN111978165A (en) * | 2020-08-06 | 2020-11-24 | 上海应用技术大学 | Method for improving acetone recovery rate in condensation process of producing pseudo ionone |
CN112638855A (en) * | 2020-11-18 | 2021-04-09 | 厦门金达威维生素有限公司 | Continuous synthesis method of pseudo ionone |
WO2022104581A1 (en) * | 2020-11-18 | 2022-05-27 | 厦门金达威维生素有限公司 | Method for continuously synthesizing pseudoionone |
CN112638855B (en) * | 2020-11-18 | 2023-05-23 | 厦门金达威维生素有限公司 | Continuous synthesis method of pseudo ionone |
CN113563168A (en) * | 2021-07-06 | 2021-10-29 | 万华化学集团股份有限公司 | Method for reducing waste water in production of pseudo ionone |
CN113548952A (en) * | 2021-07-28 | 2021-10-26 | 万华化学集团股份有限公司 | Preparation method of high-quality pseudo ionone |
Also Published As
Publication number | Publication date |
---|---|
CN103044223B (en) | 2015-04-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103044223B (en) | Method for continuously preparing pseudo ionone of vitamin A intermediate | |
CN104649878A (en) | Continuous synthesis technology of beta-isophorone | |
CN107056596B (en) | Preparation method of 2,6,11, 15-tetramethyl-2, 4,6,8,10,12, 14-hexadecaheptadien dialdehyde | |
CN104387236B (en) | A kind of propilolic alcohol, 1,4-butynediols and methenamine three coproduction continuous producing method | |
CN106831315B (en) | Continuous production method of chloroethane | |
CN103992206A (en) | Method and system for preparing 3-methyl-2-buten-1-ol through ester exchange | |
CN103787854A (en) | Preparation process of perfluoro-2-methyl-3-pentanone | |
CN103467263B (en) | Preparation method of isophorone | |
CN109809970A (en) | A kind of method of catalysis of phenol and methanol production methyl phenyl ethers anisole | |
CN1310863C (en) | Continuous process for producing pseudoionones and ionones | |
CN104557564B (en) | Preparation method of phenylmethylamine | |
CN100334056C (en) | Production of unsaturated ketone | |
CN103274913A (en) | Method and device for producing methyl isobutyl ketone | |
CN105967978B (en) | Aqueous methyl butenol isomery is combined to prenol | |
CN105130741B (en) | A kind of reactive distillation prepares the method for isoprene | |
CN105439823B (en) | A kind of method for synthesizing the alcohol of 3 methyl, 3 butylene 1 | |
CN101412661A (en) | Solid-state cardanol and preparation thereof | |
CN103524317B (en) | The synthetic method of pseudo ionone | |
CN104710292B (en) | A kind of process for purification and process unit of anhydrous pure formaldehyde gas | |
CN103588622A (en) | Method for synthesizing 2-methallyl alcohol through continuous hydrolysis reaction | |
CN103319335B (en) | Preparation method of D-(-)-O-methyl mandelic acid chloride | |
CN102584552B (en) | Method for preparing benzalacetone under supercritical condition | |
CN102701920B (en) | Method for purifying vinyl isobutyl ether | |
CN104478683A (en) | Synthetic method of 2-heptanone | |
CN106365951A (en) | 2-bromopropane recycling and reuse process in preparation process of 2,2-Diisopropylpropionitrile |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant |