CN108997271A - A kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume - Google Patents
A kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume Download PDFInfo
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- CN108997271A CN108997271A CN201810882278.4A CN201810882278A CN108997271A CN 108997271 A CN108997271 A CN 108997271A CN 201810882278 A CN201810882278 A CN 201810882278A CN 108997271 A CN108997271 A CN 108997271A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention belongs to fine chemistry industry production technical fields, and in particular to a kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume, comprising the following steps: (a) mixes raw material, obtains ingredients mixture；(b) blowing enters in preheater and preheats from octanol head tank；(c) octanol is driven into the higher boiling feed zone of reactive distillation column reaction zone, ingredients mixture is squeezed into the low boiling point feed zone of reactive distillation column reaction zone；(d) gamma-undecalactone crude product is isolated from the tower bottom of reactive distillation column；(e) octanol isolated in step (d) is transferred in preheater by product pump, continues to participate in reaction；(f) the further separating-purifying of gamma-undecalactone crude product that will be isolated in step (d)；The present invention uses reaction rectification technique, and the low boiling impurity that by-product water, the tert-butyl alcohol and side reaction are generated is separated from reaction system in time, shortens the reaction time, improves reaction speed, improves reaction efficiency.
Description
Technical field
The invention belongs to fine chemistry industry production technical fields, and in particular to a kind of reactive distillation synthesis gamma-undecalactone conjunction
At the production method of fragrance.
Background technique
Gamma-undecalactone is commonly called as third undecalactone, peach aldehyde, undecalactone, and No. CAS is 104-67-6, chemical name 5-
Heptyl dihydro -2 (3H)-furanone is naturally present in peach, apricot, sweet osmanthus, soy bean protein hydrolysate, cream, passion fruit and spends
In.297 DEG C of gamma-undecalactone atmospheric boiling point, it is dissolved in ethyl alcohol (1ml is dissolved in 60% ethyl alcohol of 5mL), benzylalcohol, Ergol, third
Glycol, lye, most of nonvolatile oils and mineral oil, it is several not dissolve in glycerol and water；For colorless and transparent to yellowish viscous fluid
Body has strong fruity fragrance, there is peach and amygdaloid fragrance.
Gamma-undecalactone is mostly important in lactone series synthetic perfume as one of most common fragrance, and is made
The maximum product of dosage is widely used in especially being needed in the edible essence containing peach perfume using fruity as keynote, and is suitable for
Using strong fruity, the fragrance of a flower as in the daily chemical essence of keynote.Gamma-undecalactone is used in daily chemical essence formula, mainly to deploy
The bouquet type compositions such as lilac, jasmine, violet and unreal flavor essence, in sweet osmanthus, the lily of the valley, flores aurantii, rose white, Acacia, purple
Rowland, etc. be often used in the fragrances of odor types, dosage is within 5%, and there is no limit regulations by IFRA.Meanwhile in γ-ten one
Ester also is used as food additives, is included in China GB2760 " food additives use standard ", and European Council is by γ-ten one
Lactone, which is included in, can be used in food without in the artificial flavour table that is detrimental to health, and providing its ADI is 1.25mg/
Kg, U.S. FEMA assert gamma-undecalactone be GRAS, number 3091, and through U.S.'s food and Drug Administration approval eat,
In flavor formulation, mainly to deploy the essence such as the types such as peach, apricot, plum, cherry, strawberry, milk and coconut, in mouth
Usage amount is 90mg/kg in fragrant sugar；11mg/kg in candy, 7.5mg/kg in cloth class D；7.1mg/kg in baked goods；Soft drink
4.4mg/kg in material；3.0mg/kg in cold drink.
Traditional synthesis gamma-undecalactone method is generally in the following ways:
1, inner molecular reaction directly synthesizes
Carboxylic acid, hydroxy ester and hydroxy-acid derivative can be converted into gamma lactone series using inner molecular reaction to produce
Product.Catalyst generally uses inorganic acid (such as hydrochloric acid, sulfuric acid), organic acid (such as p-methyl benzenesulfonic acid), due to raw material 4- hydroxyl ten
One acid, 4- hydroxyl undecylate and 4- hydroxyl undecanoic acid derivative are difficult to obtain, and thus synthetic route is converted into γ-ten one
The utilization of lactone has certain limitation.
2, it is lactonized under effect of sulfuric acid by beta, gamma-undecenoic acid obtained.Undecenoic acid generallys use union aldehyde and the third two
Acid reaction is made, and 80% sulfuric acid is stirred together with undecenoic acid, after the completion of lactonization reaction, reactant is washed with water,
It is neutralized, then through washing, grease is evaporated under reduced pressure up to gamma-undecalactone, this synthetic route is total with sodium carbonate liquor with oil reservoir
Body higher cost, and using sulfuric acid as catalyst, generates a large amount of three wastes in subsequent processing, with Green Chemistry carry on the back road and
It speeds.
3, make oxidant with the high prices such as cerium, vanadium acetate or manganese acetate, be synthesized by α-nonene with acetic acid reaction.With gold
Belong to or corresponding acetate is as oxidant, has the largely waste water generation containing heavy metal after reaction, from Green Chemistry, ring
Guarantor angularly considers that this synthetic route needs higher cost, is unfavorable for scale industrial production.
4, Reformatsky reaction Reformatsky reaction synthesis method
Aldehyde C-9 and β-halogen ester are condensed in the presence of zinc, beta-hydroxy acid esters is synthesized, is then dehydrated under acid catalysis
Generate corresponding gamma-undecalactone.Organic zinc reagent has been used in synthesis process, and must have been reacted in atent solvent, for reality
Now industrialization must also be for further study.
5, substituted epoxy ethane and malonate condensation method
Alkyl epoxy ethane and sodium are condensed for diethyl malonate, and decarboxylation generates gamma lactone.The synthetic route technique letter
Single, yield is higher.But raw materials used 1,2- ethylene oxide is difficult to produce, therefore promotes and applies and be restricted.
6, biological catalysis is produced
GDL enzyme has catalytic activity in nonaqueous phase, is widely used in organic synthesis, wherein being using most
Lipase, lipase can not only be catalyzed the hydrolysis of rouge, and energy catalytic esterification and ester exchange reaction in organic phase,
Lactone is formed including catalysis hydroxy fatty acid.And it is cyclized that these carboxylic acids are then extremely difficult, and yield is very low using conventional method, benefit
Complete that cyclization process is then much easier in organic media with enzyme process, this is without the mass market suspected of this kind of lactone spice
It provides a good way for, but the synthetic route is still at present in the research at initial stage.
7, free radical addition
Radical Addition is carried out in the presence of a free-radical initiator with acrylic acid or methyl acrylate using n-octyl alcohol
Gamma-undecalactone is produced, this is the gamma-undecalactone synthetic route for being capable of forming large-scale production at present.With n-octyl alcohol and third
Olefin(e) acid is starting material, and using di-t-butyl peroxide as initiator, reaction dissolvent is added, first by the way of " treating different things alike ",
Free radical addition synthesizes gamma-undecalactone crude product, is distilled to recover reaction dissolvent, is then prepared in γ-ten one by rectification and purification
Ester, in this technical process, by-product can not be separated from reaction system in time, and reaction yield is caused to decline, reaction
Time extends, and the bad breath of oil consumption of the grease smell, high-boiling-point impurity and isomers in product containing low boiling impurity, from
And influence the final products aroma quality of gamma-undecalactone.
Summary of the invention
It is an object of the invention to overcome the shortcomings of that existing gamma-undecalactone production process route is generally existing, one is provided
Kind raw material is easy to get, product yield is high, and process conditions are mild, and cost is relatively low, conducive to industrial-scale production is formed, and are easily achieved
The production method of the gamma-undecalactone synthetic perfume of product seriation.
To achieve the goals above, the present invention is achieved by the following scheme:
A kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume, comprising the following steps:
(a) by proportion scale respectively from octanol head tank, acrylic acid head tank and di-t-butyl peroxide head tank
Entered in ingredients pot by pipeline blowing and mixed, obtains ingredients mixture；
(b) entered in preheater from octanol head tank by pipeline blowing, preheater is warming up to 100~180 DEG C；
(c) octanol in preheater is driven into the higher boiling feed zone of reactive distillation column reaction zone by product pump, it will
Ingredients mixture in step (a) squeezes into the low boiling point feed zone of reactive distillation column reaction zone by the way that pump is added dropwise；
(d) the by-product tert-butyl alcohol and water are isolated from the tower top of the rectifying section of reactive distillation column, from the essence of reactive distillation column
It evaporates section side line and isolates the excessive octanol for having neither part nor lot in reaction, isolate gamma-undecalactone crude product from the tower bottom of reactive distillation column；
(e) octanol isolated in step (d) is transferred in preheater by product pump, continues to participate in reaction；
(f) the gamma-undecalactone crude product isolated in step (d) is transferred in rectifying column by product pump and is further divided
From purification, controlling rectifying column operating condition is 95~125 DEG C of tower top temperature, 3333~6667Pa of pressure condition, collects low boiling point
Impurity and the remaining octanol for having neither part nor lot in reaction terminate to collect low boiling impurity and pungent when tower top temperature decline or zero discharge
Alcohol；
(g) after step (f), control rectifying column operating condition is 105~145 DEG C of tower top temperature, pressure condition
1000~1333Pa, reflux ratio 1:1~1:12 collect gamma-undecalactone, when tower top temperature decline or zero discharge, terminate essence
It evaporates, cools down, pressure kettle is residual.
The present invention provides one kind using octanol, acrylic acid as raw material, and reactive distillation synthesizes the producer of gamma-undecalactone
Method, during free radical addition, using reaction rectification technique, by consersion unit and rectifying device be incorporated in same equipment into
Row, saves equipment investment；Meanwhile the low boiling impurity for generating by-product water, the tert-butyl alcohol and side reaction, in time from reactant
It is separated in system, improves reaction speed, improve reaction efficiency, is energy saving using reaction heat, reducing energy consumption；
Again through fragrance finishing technique, the indissociable impurity of common fractional method is removed, significant impact especially is generated to product fragrance
Gamma lactone isomers, finally obtain the soft flavorant grade gamma-undecalactone synthetic perfume of 99% or more, aroma of pure
Product.
Production method provided by the invention is with natural palm benevolence oil extract octanol cheap and easy to get and petrochemical material propylene
Acid is that starting material synthesizes gamma-undecalactone, and raw material is easy to get, and product yield is high, and process conditions are mild, and cost is relatively low, are to compare
A kind of ideal industrial process, conducive to industrial-scale production is formed, and is easily achieved product seriation.
Reaction principle of the invention is as follows:
(1) main reaction: addition reaction
(2) side reaction
Preferably, in step (a), the molar ratio of octanol, acrylic acid and di-t-butyl peroxide is (1~5): 1:
(0.1~1).
Preferably, in step (a), the molar ratio of octanol, acrylic acid and di-t-butyl peroxide is (1.1~1.8):
1:(0.1~0.2).
Preferably, in step (a), acrylic acid head tank and ingredients pot is all made of hot water or chilled brine is kept the temperature is protected
Temperature is 20 ± 5 DEG C.
Preferably, in step (b), the molar ratio of acrylic acid is (1~10) in the octanol and step (a): 1.
Preferably, in step (b), the molar ratio of acrylic acid is (3~5) in the octanol and step (a): 1.
Preferably, in step (f), 700 stainless steel ripple packing of CY is filled in rectifying tower.
Compared with prior art, the present invention has following technical effect that
1, production method provided by the invention just considers the requirement of environmental protection, comprehensive utilization of resources at the beginning of the design, is swimming
From in base addition process, using reaction rectification technique, consersion unit and rectifying device are incorporated in same equipment and carried out, pair
The low boiling impurity that product water, the tert-butyl alcohol and side reaction generate, is separated from reaction system in time, promotees separation with reaction,
Promote to react two-way progress with separation, shorten the reaction time, improves reaction speed, promote reaction efficiency, utilize reaction heat saving energy
Equipment investment is saved in source；
2, it in the process of synthesis gamma-undecalactone, due to the unstability of acrylic acid, is easy to happen polymerization reaction and is formed
Trimerization even heteropolymer, to influence the yield of product, therefore will reduce the polymerization reaction probability of acrylic acid in the reaction, need
Reaction dissolvent to be added in the reaction, organic solvent is substituted with excessive octanol during the reaction, it is excessive to have neither part nor lot in reaction
Octanol separated in the lateral line discharging mode of reactive distillation column, be returned directly in octanol preheater, direct circulation utilize, ginseng
With react, can substantially save because recycling distillation processing caused by energy consumption；
3, the recycling of octanol uses lateral line discharging, isolates excessive complete participation reaction from the side line of reactive distillation column
Octanol isolates gamma-undecalactone crude product from the tower bottom of reactive distillation column, and the reaction time was shortened to by original 45~60 hours
10~30 hours.Reaction time is reduced, and can be effectively controlled temperature and charging rate, inhibits the yield of side reaction and by-product,
Reaction selectivity is improved, to reduce production cost, it is ensured that product yield.
4, during acid alcohol carries out free radical addition reaction, side reaction, generated pair are inevitably had
Such as without recycling, the tert-butyl alcohol can enter Sewage Disposal in company with waste water, the load of sewage treatment is caused to rush product butanol/water
It hits, the serious collapse that will lead to Sewage Disposal biochemical treatment system.Meanwhile by-product further includes 2-ethyl hexyl acrylate, 2- nonyl
The impurity such as ketone, such as without recycling, can the product aroma quality of the product content to gamma-undecalactone and final mistake generate shadow
It rings, therefore, the bumper harvests, it can be achieved that economic benefit and environmental benefit is utilized to the comprehensive resources of by-product.After tert-butyl alcohol recycling
It can be used as the raw materials for production of di-t-butyl peroxide, it is next that methyl n-heptyl ketone and 2-ethyl hexyl acrylate itself can serve as a kind of fragrance
Use, methyl n-heptyl ketone is micro to be suitable for carnation or other spicies, new head perfume (or spice) note is formed in medicinal herbs odor type, with it is pungent it is fragrant,
Fruity class fragrance can be coordinated and cooperate, in edible essence, for Banana Type, coconut, cream, cheese fragrance edible essence,
2-ethyl hexyl acrylate can be widely applied to the fields such as fragrance, fuel adjunct, rubber chemicals, be used for santal product, fuel adjunct, rubber
Product auxiliary agent synthesizes defomaing agent and produces surfactant etc..
Specific embodiment
In order to be easy to understand the technical means, the creative features, the aims and the efficiencies achieved by the present invention, tie below
Specific embodiment is closed, the present invention is furture elucidated.
Embodiment 1
A kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume, comprising the following steps:
(a) it is pressed respectively from octanol head tank, acrylic acid head tank and di-t-butyl peroxide head tank using a high position
Octanol 1500kg, acrylic acid 750kg and di-t-butyl peroxide 150kg are added to ingredients pot by pipeline blowing by difference
In be uniformly mixed, obtain ingredients mixture；
(b) from octanol head tank using high-order pressure difference, by pipeline blowing, by 4500kg octanol blowing into preheater,
Preheater is warming up to 100~180 DEG C；
(c) octanol in preheater is driven into the higher boiling feed zone of reactive distillation column reaction zone by product pump, it will
(a) the low boiling point feed zone that the ingredients mixture in step is driven into reactive distillation column reaction zone by the way that pump is added dropwise；
(d) the by-product tert-butyl alcohol and water are isolated from the tower top of the rectifying section of reactive distillation column, from the essence of reactive distillation column
It evaporates section side line and isolates the excessive octanol for having neither part nor lot in reaction, isolate gamma-undecalactone crude product from the tower bottom of reactive distillation column.
(e) octanol that (d) step is isolated is transferred in preheater by product pump, continues to participate in reaction.
(f) the gamma-undecalactone crude product that (d) step is isolated further separation is transferred in rectifying column by product pump to mention
Pure, control rectifying column operating condition is 95~125 DEG C of tower top temperature, 3333~6667Pa of pressure condition, collects low boiling impurity
Terminate to collect low boiling impurity and octanol when tower top temperature decline or zero discharge with the remaining octanol for having neither part nor lot in reaction；
(g) after (f) the end of the step, control rectifying column operating condition is 105~145 DEG C of tower top temperature, pressure condition 1000
~1333Pa, reflux ratio 1:1~1:12 collect gamma-undecalactone, when tower top temperature decline or zero discharge, terminate rectifying, drop
Temperature, pressure kettle are residual.
In the present embodiment, the by-product tert-butyl alcohol and water 171kg are isolated from the tower top of the rectifying section of reactive distillation column；From anti-
The tower bottom of rectifying column is answered to isolate gamma-undecalactone crude product 1970kg；
Collect the octanol 148kg for having neither part nor lot in reaction of low boiling impurity, byproduct methyl n-heptyl ketone 25kg and remnants；
It in step (g), is fractionated under the conditions of reflux ratio 1:1~1:12, after collecting by-product 2-ethyl hexyl acrylate 13kg, is received
Collect gamma-undecalactone, obtains gamma-undecalactone product 1715kg.
The gamma-undecalactone product being prepared is colourless transparent liquid, the fragrance with fruity, peach sample, through gas phase
Chromatography product purity is 99.18%, and (20 DEG C) of refraction index of detection are 1.4502, and (25 DEG C) of relative density are 0.9433.
Embodiment 2
The present embodiment produces gamma-undecalactone synthetic perfume as described in Example 1, unlike, in step (a), respectively
The additional amount of material are as follows: octanol 1590kg, di-t-butyl peroxide 162kg, acrylic acid 800kg；
In step (b), the additional amount of octanol is 4337kg；Remaining method and step is consistent with the implementation method in embodiment 1.
In the present embodiment, the by-product tert-butyl alcohol and water 238kg are isolated from the tower top of the rectifying section of reactive distillation column；From anti-
The tower bottom of rectifying column is answered to isolate gamma-undecalactone crude product 1393kg；
Collect the octanol 106kg for having neither part nor lot in reaction of low boiling impurity, byproduct methyl n-heptyl ketone 35kg and remnants；
After collecting by-product 2-ethyl hexyl acrylate 15kg, gamma-undecalactone is collected, gamma-undecalactone product 1227kg is obtained.
Embodiment 3
The present embodiment produces gamma-undecalactone synthetic perfume as described in Example 1, unlike, in step (a), respectively
The additional amount of material are as follows: octanol 1887kg, di-t-butyl peroxidase 12 35kg, acrylic acid 580kg；
In step (b), the additional amount of octanol is 5240g；Remaining method and step is consistent with the implementation method in embodiment 1.
In the present embodiment, the by-product tert-butyl alcohol and water 306kg are isolated from the tower top of the rectifying section of reactive distillation column；From anti-
The tower bottom of rectifying column is answered to isolate gamma-undecalactone crude product 1049kg；
Collect the octanol 117kg for having neither part nor lot in reaction of low boiling impurity, byproduct methyl n-heptyl ketone 24kg and remnants；
After collecting by-product 2-ethyl hexyl acrylate 11kg, gamma-undecalactone is collected, gamma-undecalactone product 890kg is obtained.
Product testing GC condition are as follows: chromatographic column HP-5 (30m × 0.32mm × 0.25 μm)；Detector FID, 280 DEG C of temperature；
Sample introduction: sample volume about 0.2 μ l, split ratio 1:100,250 DEG C of injector temperature；Carrier gas: N2, flow velocity 20L/min presses before column
34.47kPa；Chromatograph oven temperature: for linear temperature program from 100 DEG C~190 DEG C, heating rate is 10 DEG C/min, retains 15min.
Basic principles and main features and the features of the present invention of the invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement is both fallen in the range of claimed invention.The scope of protection of present invention is by appended claims
And its equivalent thereof.
Claims (7)
1. a kind of production method of reactive distillation synthesis gamma-undecalactone synthetic perfume, it is characterised in that: the following steps are included:
(a) pass through from octanol head tank, acrylic acid head tank and di-t-butyl peroxide head tank respectively by proportion scale
Pipeline blowing, which enters in ingredients pot, to be mixed, and ingredients mixture is obtained；
(b) entered in preheater from octanol head tank by pipeline blowing, preheater is warming up to 100~180 DEG C；
(c) octanol in preheater is driven into the higher boiling feed zone of reactive distillation column reaction zone by product pump, by step
(a) ingredients mixture in squeezes into the low boiling point feed zone of reactive distillation column reaction zone by the way that pump is added dropwise；
(d) the by-product tert-butyl alcohol and water are isolated from the tower top of the rectifying section of reactive distillation column, from the rectifying section of reactive distillation column
Side line isolates the excessive octanol for having neither part nor lot in reaction, isolates gamma-undecalactone crude product from the tower bottom of reactive distillation column；
(e) octanol isolated in step (d) is transferred in preheater by product pump, continues to participate in reaction；
(f) the gamma-undecalactone crude product isolated in step (d) further separation is transferred in rectifying column by product pump to mention
Pure, control rectifying column operating condition is 95~125 DEG C of tower top temperature, 3333~6667Pa of pressure condition, collects low boiling impurity
Terminate to collect low boiling impurity and octanol when tower top temperature decline or zero discharge with the remaining octanol for having neither part nor lot in reaction；
(g) after step (f), control rectifying column operating condition is 105~145 DEG C of tower top temperature, pressure condition 1000~
1333Pa, reflux ratio 1:1~1:12 collect gamma-undecalactone, when tower top temperature decline or zero discharge, terminate rectifying, drop
Temperature, pressure kettle are residual.
2. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (a), the molar ratio of octanol, acrylic acid and di-t-butyl peroxide is (1~5): 1:(0.1~1).
3. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (a), the molar ratio of octanol, acrylic acid and di-t-butyl peroxide is (1.1~1.8): 1:(0.1~0.2).
4. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (a), acrylic acid head tank and ingredients pot is all made of hot water or chilled brine is kept the temperature, holding temperature is 20 ± 5
℃。
5. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (b), the molar ratio of acrylic acid is (1~10) in the octanol and step (a): 1.
6. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (b), the molar ratio of acrylic acid is (3~5) in the octanol and step (a): 1.
7. the production method of reactive distillation synthesis gamma-undecalactone synthetic perfume according to claim 1, feature exist
In: in step (f), 700 stainless steel ripple packing of CY is filled in rectifying tower.
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| CN113651697A (en) * | 2021-08-17 | 2021-11-16 | 山东石大胜华化工集团股份有限公司 | Process method for synthesizing diethyl phenylmalonate by reaction-rectification technology |
| CN114957011A (en) * | 2022-05-27 | 2022-08-30 | 安徽华业香料股份有限公司 | Method for comprehensively utilizing lactone byproduct resources |
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| 宋云飞，等人: "连续反应中γ-十一内酯合成宏观动力学研究", 《化学反应工程与工艺》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108997272A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of method of reactive distillation synthesis gamma-undecalactone synthetic perfume |
| CN113651697A (en) * | 2021-08-17 | 2021-11-16 | 山东石大胜华化工集团股份有限公司 | Process method for synthesizing diethyl phenylmalonate by reaction-rectification technology |
| CN114957011A (en) * | 2022-05-27 | 2022-08-30 | 安徽华业香料股份有限公司 | Method for comprehensively utilizing lactone byproduct resources |
| CN114957011B (en) * | 2022-05-27 | 2024-01-30 | 安徽华业香料股份有限公司 | Comprehensive utilization method of lactone byproduct resources |
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Application publication date: 20181214 |