CN109608324A - A kind of preparation process of 2,2-dimethylbutyric acid - Google Patents
A kind of preparation process of 2,2-dimethylbutyric acid Download PDFInfo
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- CN109608324A CN109608324A CN201910041256.XA CN201910041256A CN109608324A CN 109608324 A CN109608324 A CN 109608324A CN 201910041256 A CN201910041256 A CN 201910041256A CN 109608324 A CN109608324 A CN 109608324A
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- magnesium
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- acid dimethyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
Abstract
The preparation process of one kind 2,2- acid dimethyl is related to chemical reagent synthesis field.This 2, the preparation process of 2- acid dimethyl includes: that gained will be hydrolyzed after tertiary pentyl halogen magnesium grignard reagent and carbon dioxide addition reaction, it uses tertiary pentyl halogen magnesium grignard reagent and carbon dioxide to carry out carbonyl addition, preparation process is easy to operate, raw material is easy to get, yield is higher, finished product obtained is easily purified simultaneously, it can reach 99% or more after purification, with good application prospect.
Description
Technical field
This application involves chemical reagent to synthesize field, in particular to the preparation process of one kind 2,2- acid dimethyl.
Background technique
2,2- acid dimethyls are the intermediates of medicine and pesticide, are used to prepare Simvastatin, Envidor.Preparation at present
Technique is to be synthesized using tert-pentyl alcohol, sulfuric acid and formic acid, but finished product miscellaneous peak is more, and not only yield is very low (30% or so), is also difficult to
Purification, purity are generally 96%, and in actual use process, the demand of client is 99% or more.
Therefore, based on the above issues, the new preparation process of one kind 2,2- acid dimethyl is proposed.
Summary of the invention
The application provides the preparation process of one kind 2,2- acid dimethyl, to improve or alleviate existing 2,2- dimethyl butyrate
The lower status of purity and yield of acid.
According to the preparation process of 2,2- acid dimethyl provided by the embodiments of the present application comprising:
Gained will be hydrolyzed after tertiary pentyl halogen magnesium grignard reagent and carbon dioxide addition reaction.
According to the preparation process of 2, the 2- acid dimethyl of the offer of the embodiment of the present application, tried using tertiary pentyl halogen magnesium format
Agent and carbon dioxide carry out carbonyl addition, and preparation process is easy to operate, raw material is easy to get, yield is higher, at the same it is obtained at
Product are easily purified, and can reach 99% or more after purification, with good application prospect.
Wherein, tertiary pentyl halogen magnesium grignard reagent includes tert-amyl chloride magnesium grignard reagent and tert-amyl bromide magnesium grignard reagent.Example
Such as tertiary pentyl halogen magnesium grignard reagent be tert-amyl bromide magnesium grignard reagent or tert-amyl chloride magnesium grignard reagent, one shown in the application
In a little embodiments, tertiary pentyl halogen magnesium grignard reagent is tert-amyl chloride magnesium grignard reagent, is easier to prepare, reaction effect is good, together
When be convenient for sequential hydrolysis and purification.
Optionally, in order to improve the efficiency of hydrolysis, improve the yield of 2,2- acid dimethyl, under the acid condition of hydrolysis into
Row, such as be hydrolyzed in the aqueous solution existing for hydrochloric acid, hydrolysis is more thorough, effectively removes the magnesyl connected on oxygen atom
Group, while the yield of 2, the 2- acid dimethyl effectively improved.
In addition, also having following additional technology special according to the preparation process of 2, the 2- acid dimethyl of the embodiment of the present application
Sign:
In some embodiments shown in the application, the mass ratio of the additive amount of tert-amyl chloride magnesium grignard reagent and carbon dioxide
For (52-54): (43-45), such as the mass ratio of additive amount of tert-amyl chloride magnesium grignard reagent and carbon dioxide is 52:43,53:
43, any point in 53:45,54:42,54:44 or the value range between any two points.
Wherein, in order to guarantee that tert-amyl chloride magnesium grignard reagent reacts completely, the additive amount of carbon dioxide is slightly excessive, effectively
Reduce impurity content in subsequent 2,2-dimethylbutyric acid.
Wherein, carbon dioxide is dry carbon dioxide gas, in some other embodiment provided by the present application, two
Carbonoxide can also use dry ice.
In some embodiments shown in the application, addition reaction carries out under conditions of 35-45 DEG C, such as addition reaction exists
It is carried out within the temperature range of between any temperature or any two point value in 35 DEG C, 37 DEG C, 39 DEG C, 40 DEG C, 42 DEG C, 45 DEG C,
In the temperature range, stable reaction, yield is higher.
Optionally, further include keeping the temperature 0.5-2h after addition reaction, stablize addition reaction product, improve yield.
Since the crude product purity of 2, the 2- acid dimethyl obtained after hydrolysis is lower, it is unable to satisfy the demand of portions of client,
Therefore in some embodiments shown in the application, further include being refined after hydrolyzing, effectively improve 2,2- acid dimethyl
Purity, purification include:
The crude product that oily is obtained after hydrolysis is alkalized into water, to obtain the aqueous solution of 2,2- dimethyl butyrate hydrochlorate；
By the aqueous solution of 2,2- dimethyl butyrate hydrochlorate after acid displacement reaction, the sample of obtained oily is distilled, is collected
Product fraction.
It is easily purified using the crude product of 2,2- acid dimethyl made from the application, it can be effective by the refining methd
The purity of 2,2- acid dimethyl is improved to 99% or more, meets the market demand, while the market competitiveness is good.
It should be noted that effect of the alkalization into water are as follows: by obtained effective component with 2,2- dimethyl butyrate hydrochlorate
Form is dissolved in the water, and is convenient for subsequent displacement and distillation, while removing the organic matter in the crude product of oily, and it is recyclable should
Organic matter carries out next use, and then reduces production cost.Wherein, alkalization is such as using strong sodium hydroxide or potassium hydroxide
Alkali is completely dissolved in 2,2- dimethyl butyrate acid sodium-salt or sylvite obtained in water, and then replaces through acid, obtains 2,2- dimethyl
Butyric acid, to improve subsequent yield.
Optionally, when the sample of obtained oily being distilled, the product fraction of 94-95 DEG C/5mmHg is collected, is effectively removed
The interference of impurity, improve 2,2- acid dimethyl purity, such as collect 94 DEG C/5mmHg, 94.5 DEG C/5mmHg, 95 DEG C/
The product fraction of value range between any point 5mmHg or two o'clock.
In the application, tertiary pentyl halogen magnesium grignard reagent can directly be bought in market, can also voluntarily be prepared.Tert-amyl chloride
Magnesium grignard reagent can directly be bought in market, in some embodiments shown in the application, tert-amyl chloride magnesium grignard reagent
It can be voluntarily made by following methods:
In the presence of promotor, magnesium and tert-amyl chloride are carried out obtained by haptoreaction.Optionally, promotor is tetrahydro furan
At least one of mutter with 2- methyltetrahydrofuran, reaction effect is good, while highly-safe.Optionally, only depositing in promotor
Under, the addition mass ratio of tert-amyl chloride, magnesium and promotor is followed successively by 102-112:25-34:140-160.
Optionally, in some embodiments shown in the present invention, promotor is tetrahydrofuran, is recycled convenient for subsequent,
Cost of manufacture is reduced, while effectively avoiding the purity of promotor influence product.
Optionally, there is also solvent As when magnesium and tert-amyl chloride carry out haptoreaction, when there are solvent A, tert-amyl chloride,
The addition mass ratio of magnesium, promotor and solvent A is followed successively by 102-112:25-34:95-101:55-71, and solvent A is toluene, diformazan
At least one of benzene and hexamethylene.
By the addition of solvent A, the additive amount of promotor can be effectively reduced, and then reduce cost of manufacture, simultaneously for
The yield impact of tert-amyl chloride magnesium grignard reagent is smaller.
Specific for example, haptoreaction includes: after magnesium is heated to 50 DEG C, stopping is heated, and magnesium heat release to temperature is made to reach 60-70
DEG C, when part promotor and part tert-amyl chloride initiation reaction is added, and slowing down to temperature ascending temperature and tends to stop, drop
Add the mixed liquor of the promotor of surplus, the tert-amyl chloride of surplus and solvent A optionally.
Due to part promotor and part tert-amyl chloride initiation reaction being first added, until true in such a way that substep adds
Recognize and carry out second step after initiation reaction again, reaction can be made more complete, effectively improve the availability of raw material, improves tert-amyl chloride
The yield of magnesium grignard reagent, in other words, part promotor and part tert-amyl chloride are as initiation material.
Optionally, magnesium such as can spend at the magnesium of forms according to practical situation selection magnesium powder, magnesium chips, magnesium grain, magnesium, for increasing
Contact area improves reaction efficiency, but in actual use process, it is excessively violent in order to avoid reacting, such as magnesium powder etc.
Partial size is also unsuitable too small.
Judge whether to cause, following method can be used: generating a large amount of white smoke in reaction vessel, and temperature is rapid
Rise, illustrates that reaction has been initiated.And when slowing down to temperature ascending temperature and tending to stop, then the mixed liquor of surplus is added dropwise,
It can prevent security risk.
Optionally, it is maintained at 80-90 DEG C of dropwise addition mixed liquor, and keeps the temperature 1.5-2.5h, it should be noted that, dropwise addition refers to slowly
It is a small amount of to be added, it prevents from reacting and acutely causes security risk, be added dropwise simultaneously, keep the temperature the progress that reacts fully, and then improve and receive
Rate and purity.
Optionally, the mass ratio of the additive amount of part promotor and the promotor of surplus is 1:(52-53), such as part rush
Into the mass ratio of agent and the additive amount of the promotor of surplus be 1:52,1:52.5,1:53 in any point value or any two points it
Between value range.The mass ratio of the additive amount of part promotor and part tert-amyl chloride is (0.8-1.2): (0.8-1.2), such as
The mass ratio of the additive amount of part promotor and part tert-amyl chloride be any point in 1:1,0.8:1,1:1.2,1:0.8 etc. or
Value range between any two points.Within the scope of aforementioned proportion, it is ensured that the cooperation of part promotor and part tert-amyl chloride is imitated
Fruit is good, while the selection of the amount of part promotor and part tert-amyl chloride, the safety of initiation reaction can be effectively ensured, together
When avoid waste material.
The additional aspect and advantage of the application will be set forth in part in the description, and will partially become from the following description
It obtains obviously, or recognized by the practice of the application.
Specific embodiment
It, below will be in the embodiment of the present application to keep the purposes, technical schemes and advantages of the embodiment of the present application clearer
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, according to normal conditions or manufacturer builds
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
In this application, term " first ", " second ", " third " etc. are only used for distinguishing description, and should not be understood as indicating
Or imply relative importance.
Wherein, tert-amyl chloride can directly be bought in market, can also voluntarily be prepared.
In the application, a kind of method of tert-amyl chloride voluntarily prepared is provided, is based on reaction mechanism are as follows:The high income of tert-amyl chloride obtained, purity is high.
Specifically, the method for tert-amyl chloride voluntarily prepared includes:
After tert-pentyl alcohol, hydrochloric acid, zinc chloride are mixed, 6-8h is kept the temperature after being heated to 60-70 DEG C, is subsequently passed hydrogen chloride gas
To its saturation, cooling is dry through anhydrous magnesium sulfate by the oil reservoir after layering, to obtain tert-amyl chloride.
Wherein, for zinc chloride as catalyst, additive amount is the 3.5-4% of tert-pentyl alcohol quality, is effectively catalyzed tert-pentyl alcohol and becomes
For the reaction of tert-amyl chloride.
Optionally, the water layer after recycling layering can be used for next use, effectively containing zinc chloride and part hydrochloric acid
Raw material is saved, while reducing cost of manufacture.
Such as: be added into the four-hole bottle of 1000ml the tert-pentyl alcohol of 264g, the hydrochloric acid that 500g mass fraction is 30% and
10g zinc chloride is heated to 60 DEG C, 7h is then kept the temperature after 60-70 DEG C, is down to room temperature, by the oil reservoir of layering through anhydrous magnesium sulfate
It is dry, 287.5g tert-amyl chloride is obtained, in terms of tert-pentyl alcohol, yield is greater than 90%.
The feature of the application and performance are described in further detail with reference to embodiments.
Embodiment 1
The preparation process of one kind 2,2- acid dimethyl comprising:
(1) it uses's
Mechanism prepares tert-amyl chloride magnesium grignard reagent.
Specifically, 27g magnesium chips is added in the first dry reaction vessel, starts to stir and begin to warm up, be heated to 50
DEG C when stop heating, when the temperature in reaction vessel is flushed to 60-70 DEG C, be added 2g tetrahydrofuran and 2g tert-amyl chloride mixing
Object expects initiation reaction as causing, if generating a large amount of white smoke in reaction vessel, and temperature rises rapidly, then illustrates
Reaction has been initiated.When temperature rise process become it is slow and tend to stop when, be maintained at 80-90 DEG C be added dropwise by 104.5g
The mixed liquor of tert-amyl chloride, 100g tetrahydrofuran and 60g toluene composition, and protected after mixed liquor is added dropwise at 80-90 DEG C
Warm 2h obtains tert-amyl chloride magnesium grignard reagent.
Wherein, tert-amyl chloride is made using the method that present specification provides.
(2) 2,2-dimethylbutyric acid is prepared using following mechanism
Specifically, the tertiary pentyl halogen magnesium grignard reagent that step (1) obtains is cooled to 35 DEG C, is maintained at 35-45 DEG C of temperature
It is passed through 88g carbon dioxide in degree range, has led to heat preservation 1h, has kept tertiary pentyl halogen magnesium grignard reagent and the abundant addition of carbon dioxide anti-
It answers, obtains 2,2- dimethyl butyrate hydrochlorate reagent.
Then in the second reaction vessel, 150g hydrochloric acid and 300g water is added, stirs and cools down, a dropping step (2)
2, the 2- dimethyl butyrate hydrochlorate reagent arrived, is added dropwise, and temperature rising reflux 4h is cooled to room temperature, the first reagent being layered.It goes
Except the water layer of the first reagent, 500ml water, 60g piece alkali are added in the oil reservoir of the first reagent, stirs 30min, continues to be layered, obtain
To the second reagent, 2, the 2- acid dimethyl hydrolyzed at this time is by the water layer of alkali carries to the second reagent, the second reagent
Oil reservoir be mainly organic matter, can be recycled recycling.
Hydrochloric acid is added to be acidified to pH=1 the water layer of the second reagent, the third reagent being layered takes the oil reservoir of third reagent
Be evaporated under reduced pressure, collect 94-95 DEG C/5mmHg fraction to get.
2,2- acid dimethyl made from the present embodiment, is measured using gas chromatography, and purity is greater than 99%, and product is received
Rate is in terms of tert-pentyl alcohol, yield 72%.
Embodiment 2
The preparation process of one kind 2,2- acid dimethyl comprising:
(1) 28g magnesium chips is added in the first dry reaction vessel, starts to stir and begin to warm up, when being heated to 50 DEG C
Stop heating, when the temperature in reaction vessel is flushed to 60-70 DEG C, the mixture of 2g tetrahydrofuran and 2g tert-amyl chloride be added,
Initiation reaction is expected as causing, if generating a large amount of white smoke in reaction vessel, and temperature rises rapidly, then illustrates to react
It has been initiated.When temperature rise process become it is slow and tend to stop when, be maintained at 80-90 DEG C be added dropwise by uncle 104.5g penta
The mixed liquor of base chlorine, 150g tetrahydrofuran composition, and tertiary pentyl is obtained in 80-90 DEG C of heat preservation 2h after mixed liquor is added dropwise
Chlorine magnesium grignard reagent.
Wherein, tert-amyl chloride is made using the method that present specification provides.
(2) the tertiary pentyl halogen magnesium grignard reagent that step (1) obtains is cooled to 35 DEG C, is maintained at 35-45 DEG C of temperature model
It is passed through 89g carbon dioxide in enclosing, has led to heat preservation 1h, has made tertiary pentyl halogen magnesium grignard reagent and the abundant addition reaction of carbon dioxide, obtain
To 2,2-dimethylbutyric acid salt reagent.
(3) in the second reaction vessel, 150g hydrochloric acid and 300g water is added, stirs and cools down, a dropping step (2) obtains
2,2- dimethyl butyrate hydrochlorate reagent, be added dropwise, temperature rising reflux 4h is cooled to room temperature, the first reagent being layered.Removal
500ml water, 62g piece alkali is added in the water layer of first reagent in the oil reservoir of the first reagent, stirs 35min, continues to be layered, obtain
Second reagent, 2, the 2- acid dimethyl hydrolyzed at this time by the water layer of alkali carries to the second reagent, the second reagent
Oil reservoir is mainly organic matter, and recycling can be recycled.
Hydrochloric acid is added to be acidified to pH=1 the water layer of the second reagent, the third reagent being layered takes the oil reservoir of third reagent
Be evaporated under reduced pressure, collect 94-95 DEG C/5mmHg fraction to get.
2,2- acid dimethyl made from the present embodiment, is measured using gas chromatography, and purity is greater than 99%, and product is received
Rate is in terms of tert-pentyl alcohol, yield 71%.
Embodiment 3
The preparation process of one kind 2,2- acid dimethyl comprising:
(1) 90g dioxy is passed through within the temperature range of the temperature of 107g tert-amyl chloride magnesium grignard reagent being maintained at 35-45 DEG C
Change carbon, has led to heat preservation 1h, made tert-amyl chloride magnesium grignard reagent and the abundant addition reaction of carbon dioxide, obtain 2,2- acid dimethyl
Salt reagent.
(2) 160g hydrochloric acid and 310g water are stirred, are cooled to room temperature, 2, the 2- dimethyl that a dropping step (1) obtains
Butyrate reagent, is added dropwise, and temperature rising reflux 4h is cooled to room temperature, the first reagent being layered.Remove the water of the first reagent
500ml water, 60g piece alkali is added in layer in the oil reservoir of the first reagent, stirs 30min, continues to be layered, obtain the second reagent, at this time
Obtained 2,2- acid dimethyl is hydrolyzed by the water layer of alkali carries to the second reagent, the oil reservoir of the second reagent is predominantly organic
Recycling can be recycled in object.
Hydrochloric acid is added to be acidified to pH=1 the water layer of the second reagent, the third reagent being layered takes the oil reservoir of third reagent
Be evaporated under reduced pressure, collect 94-95 DEG C/5mmHg fraction to get.
Embodiment 4
The preparation process of one kind 2,2- acid dimethyl, and being different only in that for embodiment 1:
(1) 25g magnesium chips is added in the first dry reaction vessel, starts to stir and begin to warm up, when being heated to 50 DEG C
Stop heating, when the temperature in reaction vessel is flushed to 60-70 DEG C, the mixing of 1.5g tetrahydrofuran and 1.5g tert-amyl chloride is added
Object expects initiation reaction as causing, if generating a large amount of white smoke in reaction vessel, and temperature rises rapidly, then illustrates
Reaction has been initiated.When temperature rise process become it is slow and tend to stop when, be maintained at 80-90 DEG C be added dropwise by uncle 106g
The mixed liquor of amyl chloride, 98.5g tetrahydrofuran composition, and uncle penta is obtained in 80-90 DEG C of heat preservation 2h after mixed liquor is added dropwise
Base chlorine magnesium grignard reagent.
Embodiment 5
The preparation process of one kind 2,2- acid dimethyl is different only in that step (3) with embodiment 1.
In the present embodiment, (3) are added 150g hydrochloric acid and 300g water, stir and cool down in the second reaction vessel, are added dropwise
2, the 2- dimethyl butyrate hydrochlorate reagent that step (2) obtains, is added dropwise, and temperature rising reflux 4h is cooled to room temperature, be layered
One reagent.The oil reservoir of first reagent is evaporated under reduced pressure, collect 94-95 DEG C/5mmHg fraction to get.
2,2- acid dimethyl purity 96%, is decreased obviously compared to embodiment 1 made from the present embodiment.
To sum up, the preparation process of 2,2- acid dimethyl provided by the present application is effectively improved existing 2,2- dimethyl butyrate
The lower status of purity and yield of acid, at the same it is easy to operate, it is suitable for industrialized production.
The above is only preferred embodiment of the present application, are not intended to limit this application, for those skilled in the art
For member, various changes and changes are possible in this application.Within the spirit and principles of this application, it is made it is any modification,
Equivalent replacement, improvement etc., should be included within the scope of protection of this application.
Claims (10)
1. one kind 2, the preparation process of 2- acid dimethyl, characterized in that it comprises:
Gained will be hydrolyzed after tertiary pentyl halogen magnesium grignard reagent and carbon dioxide addition reaction；
The tertiary pentyl halogen magnesium grignard reagent includes tert-amyl chloride magnesium grignard reagent and tert-amyl bromide magnesium grignard reagent.
2. the preparation process of 2,2- acid dimethyl according to claim 1, which is characterized in that the tertiary pentyl halogen magnesium lattice
Formula reagent is tert-amyl chloride magnesium grignard reagent, the quality of the tert-amyl chloride magnesium grignard reagent and the additive amount of the carbon dioxide
Than for (52-54): (43-45).
3. the preparation process of 2,2- acid dimethyl according to claim 2, which is characterized in that the addition reaction exists
It is carried out under conditions of 35-45 DEG C；
It preferably, further include keeping the temperature 0.5-2h after the addition reaction.
4. the preparation process of 2,2- acid dimethyl according to claim 2, which is characterized in that further include in the hydrolysis
After refined, the purification includes:
The crude product that oily is obtained after hydrolysis is alkalized into water, to obtain the aqueous solution of 2,2- dimethyl butyrate hydrochlorate；
By the aqueous solution of 2, the 2- dimethyl butyrate hydrochlorate after acid displacement reaction, the sample of obtained oily is distilled, is collected
Product fraction.
5. the preparation process of 2,2- acid dimethyl according to claim 4, which is characterized in that 94-95 DEG C of collection/
The product fraction of 5mmHg.
6. the preparation process of 2,2- acid dimethyl according to claim 2, which is characterized in that the tert-amyl chloride magnesium lattice
Formula reagent is made by following methods:
In the presence of promotor, magnesium and tert-amyl chloride are carried out obtained by haptoreaction, the promotor is tetrahydrofuran and 2-
At least one of methyltetrahydrofuran；
Preferably, the addition mass ratio of the tert-amyl chloride, the magnesium and the promotor is followed successively by 102-112:25-34:
140-160。
7. the preparation process of 2,2- acid dimethyl according to claim 6, which is characterized in that magnesium and tert-amyl chloride carry out
There is also solvent A when haptoreaction, the tert-amyl chloride, the magnesium, the promotor and the solvent A addition mass ratio according to
Secondary is 102-112:25-34:95-101:55-71, and the solvent A is at least one of toluene, dimethylbenzene and hexamethylene.
8. the preparation process of 2,2- acid dimethyl according to claim 7, which is characterized in that the haptoreaction packet
It includes: after the magnesium is heated to 50 DEG C, stopping heating, make magnesium heat release to temperature up to 60-70 DEG C, part promotor and portion is added
When dividing tert-amyl chloride initiation reaction, and slowing down to temperature ascending temperature and tend to stop, the promotor, the surplus of surplus is added dropwise
The tert-amyl chloride and solvent A optionally mixed liquor.
9. the preparation process of 2,2- acid dimethyl according to claim 8, which is characterized in that be maintained at 80-90 DEG C of drop
Add the mixed liquor, and keeps the temperature 1.5-2.5h.
10. the preparation process of 2,2- acid dimethyl according to claim 8, which is characterized in that the part promotor
Mass ratio with the additive amount of the promotor of surplus is 1:(52-53), the part promotor and the part tertiary pentyl
The mass ratio of the additive amount of chlorine is (0.8-1.2): (0.8-1.2).
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| CN114057562A (en) * | 2021-12-07 | 2022-02-18 | 山东华安新材料有限公司 | Preparation method of 4,4, 4-trifluorobutyric acid |
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| CN114057565A (en) * | 2021-12-07 | 2022-02-18 | 山东华安新材料有限公司 | Preparation method of 3,3, 3-trifluoropropionic acid |
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